US 20130251730A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0251730 A1 Ley et al. (43) Pub. Date: Sep. 26, 2013

(54) COMPOUNDS AND MIXTURES USPC ...... 424/158.1:562/463: 514/568; 549/399; INFLUENCING INFLAMMATORY STATES 514/456; 549/403; 424/93.4: 514/171; 514/150; 514/249; 514/263.2: 514/635 (71) Applicant: SYMRISE AG, Holzminden (DE) (57) ABSTRACT (72) Inventors: Jakob Ley, Holzminden (DE); Suggested is a compound of the formula (X) Katharina Reichelt, Holzminden (DE); Marcus Götz, Oberweser (DE); Maria Blings, Holzminden (DE); Veronika (X) Somoza, Weidling (AT); Jessica Walker, Vienna (AT); Joel Michael Walker, Vienna (AT) (73) Assignee: Symrise AG, Holzminden (DE) (21) Appl. No.: 13/782,391 (22) Filed: Mar. 1, 2013 or any salt of a compound of the formula (X) or any mixture (30) Foreign Application Priority Data containing or consisting of two or more different compounds of the formula (X), two or more different salts of compounds Mar. 2, 2012 (EP). ... 12157903.1 of the formula (X) or one or more different compounds of the Feb. 5, 2013 (EP) ...... 13154O23.9 formula (X) and one or more different salts of compounds of the formula (X), wherein for R1,R2 and R3 independently of one another in every com Publication Classification pound of the formula (X) the following applies: R1 means hydrogen or methyl, (51) Int. Cl. R2 means an organic residue with 5 carbon atoms and one A6 IK3I/92 (2006.01) oxygen atom or none and CO7D 3II/58 (2006.01) R3 means an organic residue with 10 carbonatoms and one or A2.3L I/30 (2006.01) more OXygen atoms, CO7D 3II/32 (2006.01) O A6 IK 45/06 (2006.01) R1 and R2 together with the carbon atoms in positions 4 and CD7C 65/40 (2006.01) 5 and the oxygenatom bound to the carbonatom in position A6 IK3I/353 (2006.01) 4 form a ring and comprise 5 carbonatoms and one oxygen (52) U.S. Cl. atom or none, and CPC ...... A6IK3I/192 (2013.01); C07C 65/40 R3 means an organic residue with 10 carbonatoms and one or (2013.01); C07D 31 1/58 (2013.01); A61 K more OXygen atoms, 31/353 (2013.01); C07D 311/32 (2013.01); for use in a method for the prophylaxis and/or treatment of A61K 45/06 (2013.01); A23L 1/3002 (2013.01) inflammation. Patent Application Publication Sep. 26, 2013 Sheet 1 of 7 US 2013/0251730 A1

Intens. x 104 8 MM=574 C22H5OO6 S. MM=408 C22H32O7 MM=358 C22H5OO4

Intens. x 105 homoeriodicytol 2.O 1.5 hesperetin

1.O eriodicytol O.5

O 2 4 6 8 10 12 14 16 18 Time min Patent Application Publication Sep. 26, 2013 Sheet 2 of 7 US 2013/0251730 A1

L1 beto 1OO X, TNF alpha 2 L6 NL8 PGE2 2 soproston

NNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN *************************** `NNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN - `NNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN ZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZ |u/677OG

FIG. 20.

L1 beta 3 TNF alpha 2 L6 N L8 PGE2 2 soprostan

NNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN -E+SCHT RINNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN -E+SCHT H&NNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN zzzzZZZZZZZZZZZZZZZZZ????????????????? -E+SCHT -E+SCHT |u/67| |u/6??Ol. ||u/67'OO

FIG. 2b Patent Application Publication Sep. 26, 2013 Sheet 3 of 7 US 2013/0251730 A1

10 ug/ml PG-LPS + 0.1 uM HED in HS 10 ug/ml PG-LPS + 1 uM HED in HS 10 ug/ml PG-LPS + 10 uM HED in HS 10 ug/ml PG-LPS + 1% EtOH Patent Application Publication Sep. 26, 2013 Sheet 4 of 7 US 2013/0251730 A1

10 ug/ml PG-LPS + 0.1 uM HED in FF 350 10 ug/ml PG-LPS + 1 uM HED in FF 10 ug/ml PG-LPS + 10 uM HED in FF 10 ug/ml PG-LPS + 1% EtOH 2 5 O

2 O O

150 -39-44-4-3 sk kakk -55-61 - 4.5 100

50

L-6 L-8 L-6

FIG. 3b Patent Application Publication Sep. 26, 2013 Sheet 5 of 7 US 2013/0251730 A1

4OO 10 ug/ml PG-LPS + 1 ug/ml EF 350 10 ug/ml PG-LPS + 10 ug/ml. EF 10 ug/ml PG-LPS + 100 lug/ml. EF 500 10 ug/ml PG-LPS + 1%. EtOH

2-50 -61-53-58

L-6 L-8 L-6 L-8 Patent Application Publication Sep. 26, 2013 Sheet 6 of 7 US 2013/0251730 A1

10 ug/ml PG-LPS + 1 ug/ml ESB 10 ug/ml PG-LPS + 10 ug/ml ESB 10 ug/ml PG-LPS + 100 ug/ml ESB 10 ug/ml PG-LPS + 1% EtOH

6h 9. Patent Application Publication Sep. 26, 2013 Sheet 7 of 7 US 2013/0251730 A1

400 10 ug/ml PG-LPS + 1 ug/ml ESC 35O 10 ug/ml PG-LPS + 10 ug/ml ESC 10 ug/ml PG-LPS + 100 ug/ml ESC 3OO 10 ug/ml PG-LPS + 1%. EtOH

150

100 -61-61 50 % -92 %2 YaYaNY L-8 L-6 L-8

FIG. 3e US 2013/025 1730 A1 Sep. 26, 2013

COMPOUNDS AND MIXTURES for irritant Substances, and also hyper-reactive, intolerant and INFLUENCING INFLAMMATORY STATES also atopic skin. In the case of people with sensitive or easily damaged skin, the so-called “stinging (Engl. "to BACKGROUND OF THE INVENTION sting-burn, stab, be painful) can be observed. Typical symp 0001 1. Field of Invention toms which are associated with “stinging” or “sensitive skin' 0002 The present invention belongs to the area pharma in general are skin reddening, tingling, feelings oftension and ceutical and cosmetic compositions and refers to novel com burning of the skin and pruritus. They can be triggered by pounds, mixtures and preparations comprising new com certain ambient influences, e.g. massage, influence of Surfac pounds with excellent anti-inflammatory properties. tants, weather (heat, cold, dryness or high atmospheric 0003 2. State of the Art humidity), thermal or UV radiation (e.g. emanating from the 0004. There is a constant need to provide inflammation Sun) or even by psychological stress. inhibiting substances for the protection of cells or tissues (of 0014 Sensitive scalp is also characterized by skin redden people and animals), in particular of the skin, above all for use ing, tingling, burning and stinging. Triggers are for example in cosmetic preparations, pharmaceutical preparations, food Soap, shampoos or other hair care products, Surfactants, water stuffs or semi-luxury products. In particular there is a con with a high calcium carbonate content and/or (mechanical) stant need to find new Substances with anti-inflammatory stress. Erythema and hyperseborrhoea (excessive sebaceous activity, which Support the natural defence mechanisms secretion) of the scalp and dandruffare often accompanied by against inflammation in physiological systems (of people and the said symptoms. animals). In this respect, there is particularly great interest in 00.15 Atopy (atopic syndrome) is observed (with a rising substances from natural extracts. Particularly attractive for trend) in ca. 10-20% of the population in industrialized coun use in foods are plants or parts or extracts of plants, which tries. This is a hypersensitivity of the skin to substances from have a long history of edible consumption. the environment with an increased tendency to development 0005. In the context of the present text, the term “skin' of hypersensitivity reactions of the immediate type (allergies) comprises not only the (human or animal) skin in the usual towards Substances from the natural environment. It is sense, but rather cell layers in general which cover internal believed that atopy has genetic causes. Atopy can appear as and/or external Surfaces on/in the human or animal body. atopic dermatitis. In this case, the skin barrier is damaged, and Accordingly, in the context of the present text, the term “skin' the skin is often inflamed and itches. comprises Surface and glandular epithelia, i.e. in particular 0016 Periodontitis (as an example of an inflammatory also mucous membranes, e.g. the oral mucosa, the gastric reaction of the gums or the oral mucosa) is an inflammation of mucosa and the intestinal mucosa. As barrier organs of the the periodontium (dental periosteum), i.e. the tissue which (human) body, the mucous membranes are exposed to exter Surrounds and Supports the teeth. The periodontium consists nal influences to a particular extent. They line the various of various tissues: gingival epithelium (gingiva, gum), con body cavities which are either in contact with the external nective tissue of the gingiva, dental periosteum (periodon environment (e.g. mouth and throat) or the internal organs of tium, desmodontium), dental cement and Surrounding alveo a body (e.g. intestinal lumen). lar bone. The dental periosteum lies between the surface of 0006. Many intrinsic factors (e.g. genetic predisposition) the root and the alveolar bone and is a cell-rich connective and extrinsic factors (e.g. damage to the skin barrier, influ tissue which holds the teeth in the osseous tooth socket, the ence of UV light, skin-irritant or allergy-triggering Sub alveolus. 53 to 74% of the periodontal gap consists of col stances) can lead to skin irritation or dysfunctions of the skin. lagen and oxytalan fibre bundles. Periodontal fibres which are 0007. In the context of the present text “skin irritation” is present in the dental cement and in the alveolar bone hold the understood to mean any change in the skin, which triggers tooth in the alveolar bone. The main characteristics of peri indisposition (“sensorial malaise'), and/or is characterized odontitis comprise inflammation of the gum, loss of stability, by symptoms of dry, reddened and/or inflamed skin. The term formation of pockets in the dental periosteum and degrada “sensorial malaise also includes states which are associated tion of the alveolar bone. with pruritus or pains. 0017. The main cause of periodontitis is plaque. This con 0008 Skin irritation can include the following skin con sists of certain components of the saliva, food residues and ditions: sensitive skin, for example sensitive Scalp, easily bacteria and degradation products thereof. This specific form damaged skin, atopic skin (atopy) and irritated or inflamed of infectious disease is in most cases caused by Porphyromo skin, which can appear in the form of skin reddening nas gingivalis, Bacteroides forsythus and Actinobacillus acti (erythema). nomycetemcomitans. The continuous release of bacterial tox 0009 Skin irritation can in particular also concern or com ins, in particular lipopolysaccharide (LPS), leads to a non prise specific immune defence reaction. LPS-stimulated 0010 irritation of the mucous membranes in the oral macrophages release prostaglandin E2 (PGE2) and pro-in cavity, for example periodontitis and gingivitis (as flammatory mediators, such as for example interleukins (e.g. described in detail below), IL-1 beta) and TNF-alpha, in the affected tissue of the patient. 0011 irritation and infections of the airways, for The pro-inflammatory mediators trigger the release of further example rhinosinusitis (common cold), sinusitis and PGE2s and matrix-destroying metalloproteinases (matrix pharyngitis/tonsillitis, and metalloproteinases, MMPs) from the invasive fibroblasts, 0012) irritation of the gastrointestinal tract. which destroy the extracellular matrix of the surrounding 0013 The problem of sensitive skin affects a growing connective tissue. This in turn allows bacteria which are actu number of adults and children. It is believed that a proportion ally in contact with the exposed gum to penetrate deeper into of up to 50% of the population have sensitive skin (see L. the underlying connective tissue and there to drive the inflam Misery et al., Ann. Dermatol. Venereol. 2005, 132, 425-429). matory process further, so that eventually the junction Sensitive skin describes skin which has a decreased threshold between the top layer of the epithelium and the root is lost. As US 2013/025 1730 A1 Sep. 26, 2013 a result a pocket in the gum is formed. The body's reaction to 0.031 liquid forms (such as for example solutions, sus this is an inflammation of the gum and the dental periosteum pensions, emulsions, syrups (colloquially cough syrup), with damage to the alveolar bone. In the final stage of peri mouthwashes, gargle solutions, throat sprays or nasal odontitis, the person affected is at risk of tooth loss. sprays, nasal drops, nasal rinse solutions, nasal powders, 0.018. However, in addition to bacteria, chemical or nasal ointments or ear drops, ear sprays, ear rinse solu mechanical damage can also cause irritation or inflammatory tions, ear powders and aural tampons), reactions of the gum or the oral mucosa. Pro-inflammatory 0.032 semisolid forms (such as for example hydropho mediators, in particular interleukins such as IL-1 alpha and bic ointments including for example: hydrocarbon gels, PGE2, are released in this process. lipogels, silicone gels, oleogels and water-absorbing 0019. Irritation and infections of the airways affect the ointments including for example absorption bases, respiratory tract (of people or animals). The respiratory tract hydrophilic ointments, hydrophilic gels (hydrogels) or is subdivided into three sections: pastes, 0020 (i) the upper airways, incl. nose and paranasal 0033. Inhalants (such as for example compressed gas sinuses and pharynx, dispenser inhalers, powder inhalers, inhalers with atom 0021 (ii) the lower airways with larynx and trachea and isers, and inhalation concentrates for inhalation), and 0022 (iii) the lungs with bronchi, bronchioles, pulmonary 0034) active substance-containing plasters or other alveoli, etc. therapeutic systems. 0023 “Irritation and infections of the upper airways' des 0035. The gastrointestinal tract (also called digestive ignate in particular an acute infection, which affects the upper tract) is the system of internal organs which take up and digest airways, nose, sinus, pharynx and/or larynx. In the United the food, in order to absorb nutrient substances therefrom, to States of America, ca. one billion acute diseases of the upper obtain energy and to excrete the food components remaining. airways are recorded each year. Irritation and infections of the Accordingly, the main functions of the digestive tract are food upper airways include rhinosinusitis (common cold), sinusi uptake, digestion, absorption and excretion. tis, pharyngitis/tonsillitis, laryngitis and sometimes bronchi 0036. The upper digestive tract consists of the mouth, tis. The symptoms of these infections often include Swelling pharynx, oesophagus and stomach. The mouth contains the of the nasal mucosae, cough, nasal catarrh, Sore throat, fever, oral mucosae, which contain the openings of the saliva Sneezing and pressure sensation. The symptoms as a rule start glands, the tongue and the teeth. Behind the mouth lies the 1 to 3 days after contact with pathogenic germs, mostly pharynx, which leads to a hollow muscular tube, the oesopha viruses. The symptoms typically cease in 7 to 10 days, but can gus, which in turn leads into the stomach. The small intestine also persist for longer. is joined to the stomach. The lower digestive tract consists of 0024. A commonly occurring (airway) infection is phar the intestines and the anus. The intestines consist of the intes yngitis. Pharyngitis is in most cases a painful inflammation of tine, the Small intestine, which consists of three parts, duode the pharynx and is thus commonly also described as Sore num, jejunum and ileum, the large intestine, which also con throat. Inflammation of the tonsils, tonsil inflammation or sists of three sections, caecum with Vermiform appendix tonsillitis can arise at the same time. (blind gut), the colon (rising colon, transverse colon and 0025. For infections of the upper airways there are essen descending colon) and the rectum. tially three therapeutic approaches: symptomatic, remedial 0037. The commonest inflammatory conditions of the and preventive. Symptomatic therapy aims to alleviate symp digestive tracts include gastro-oesophageal reflux diseases, toms and pain. Remedial therapies are intended to treat the heartburn and gastric ulcers. The therapy usually includes pharyngitis by preventing its spreading and accelerate the firstly reduction of the symptoms and reduction of the inflam healing process. Preventive therapy is intended to prevent the mation in the tissue and secondly longer-term therapies in outbreak of an infection. order to prevent reappearance of the symptoms. 0026 Remedial therapies are most effective against bac 0038. Other inflammatory diseases of the digestive sys terial infections, e.g. Streptococci. Many preventive therapies tem, inter alia, are milder inflammatory diseases such as are also remedial. irritable bowel syndrome (IBS) and inflammatory diseases of 0027. With viral infections, the recovery from a pharyn unknown aetiology and chronic inflammatory intestinal dis geal inflammation as a rule occurs spontaneously within a few eases (IBD), such as for example chronic colitis (ulcerative days. Hence the favourite method is symptomatic therapy. colitis). 0028. Various non-antibiotic therapies for throat inflam 0039. There is a particularly great need for suitable appli mation have been tested in controlled studies. Analgesic cations for the prevention or treatment of chronic inflamma therapies are among the most effective here. tory intestinal diseases, in particular chronic colitis (ulcer 0029. The symptomatic therapies for infections of the ative colitis). upper airways include: formulations whose purpose is to act 0040 Chronic inflammation can appear as a cause of vari remedially or symptomatically and which can present in the ous diseases and living conditions. It can be associated with following forms: the most diverse conditions such as arthritis, some types of 0030 solid galenical forms (such as for example tablets cancer, colitis, diabetes mellitus, coronary heart disease, obe (with and without coating, with and without modified sity, Alzheimer's disease and immune dysfunction. release), Sugar-coated tablets (with and without coating, 0041. There are essentially two enzymatic pathways for with and without modified release), capsules (soft or regulating inflammation. The lipoxygenase pathway hard gelatine capsules with and without modified (5-LOX) results in the production of leukotrienes, which have release), granules (with and without modified release), a pro-inflammatory action. The second pathway is the powders (with and without modified release), Supposi cyclooxygenase pathway (COX-1 and COX-2). A high level tories (with and without coating, with and without modi of COX-2 indicates inflammation. Further inflammation fied release), lozenges and chewing gums), markers are tumour necrosis factor (TNF-C.), nuclear factor US 2013/025 1730 A1 Sep. 26, 2013

KB (NF-kB), interleukin-6 (IL-6), interleukin-17 (IL-17) and 0048 One such recognition receptor for bacterial motifs is interleukin-1-B (IL1B). The enzymes, cytokines and metabo the so-called NOD2/CARD15 protein. NOD2/CARD15 is a lites thereof increase the production of prostaglandins and member of the NBS-LRR protein family (for nucleotide leukotrienes, which function as intercellular mediators, and binding site and leucine-rich repeat), the members whereof are connected with the inflammatory process. Regulation of all play a part in the intracellular recognition of microbes and the enzymes LOX-5 and COX-2 in particular can have a components thereof and which also include for example positive effect in the development/suppression of inflamma Apaf-1 and CARD4/NOD1, which possibly also can play a tion. part in certain patients. When bacterial components bind to 0042. A diet which is based on much sugar and starch, and NOD2/CARD15, this normally leads to activation of the pro fat and trans fatty acids, has a direct connection with chronic inflammatory transcription factor NF-kB. inflammation. Oxidation of multiply unsaturated fats and 0049 Adherent E. coli strains have been found in ulcer fatty acids in vitro and in vivo leads to the formation of ations in patients with Crohn's disease. In general, in patients reactive oxygen species (radicals), and to the formation of nitrogen oxides. These compounds can initiate and/or pro with IBD or IBS, considerably more bacteria are directly mote the first phase of an inflammatory process. Damage to adjacent to the intestinal epithelial cells than in the normal the DNA can result from this. mucosa, which is protected from contact with bacteria by a mucus layer. This observation supports the hypothesis of the 0043. Over its whole length, particularly in the region of the intestine, the gastrointestinal tractis Susceptible to inflam importance of bacterial translocation in the pathogenesis of mation, hence it is very important to inhibit corresponding IBD. processes and to prevent inflammation. Without treatment, 0050. The currently available therapies for the treatment harmful processes can lead to irritation, acute and chronic of Crohn's disease and ulcerative colitis can alleviate, but not inflammation, and onwards to cancer. cure, the disease symptoms. Most therapies end with a resis 0044 Chronic inflammatory diseases of the digestive tract tance to the antibiotic and Surgical intervention. mucosa represent a considerable health political problem. Younger people in particular are falling ill, whose whole 0051. In Biosci. BioTech. Biochem Japan, 67(9) S. 2038 lifestyle is severely affected thereby, and who have to rely on 2041 (2003) Makabeet al. showed that compound from Myrs medical care throughout their life. The aetiology/pathogen ine sequinii, in particularly myrSonic acids have some anti esis of the chronic inflammatory diseases of the digestive tract inflammatory properties. However, performance differed is not completely clear. However, it is believed to be a cause seriously between the various species and the document is of the onset of a disorder of the intestinal barrier. silent with respect to the activity of the compounds in view of 0.045 Ulcerative colitis and Crohn's disease are inflam the broad range of different inflammation parameters. mations of the intestine, which exhibit characteristic accom 0052 JP 2007/077122describes the use of plant proantho panying symptoms such as diarrhoea, blood in stools, cyanidins, for example from apple, pear, apricot, grape, abdominal pains and cramps, and weight loss. At the same guava, hops, barley or adzuki bean for the prevention of time, the intestinal mucosa appears red and Swollen and often intestinal inflammation, especially in the case of ulcerative bleeds on the slightest touch. colitis. The recommended daily intake is 100 to 2500 mg 0046. The epithelial cells of the mucosa represent the cell apple extract or corresponding quantities of apple proantho layer closest to the surface. The intestinal epithelial cells cyanidins. The effect of the apple proanthocyanidins was constitute the greatest contact area of the body with the out confirmed in mice with acute ulcerative colitis caused by side world. They absorb food and at the same time prevent the penetration of pathogenic organisms. The latter is promoted dextran sulphate (DSS, 2.5%) over a period of 20 days. by chronic physiological inflammation. This is Subject to a 0053 Models of the DSS-induced colitis (acute or range of control and regulatory mechanisms in order to avoid chronic) are rapid, simple to perform, well reproducible and on one hand the penetration of pathogenic germs and on the inexpensive. They enable the real-time study of the inflam other hand damage due to the inflammatory mediators them matory process from onset up to remission and are thus very selves. For this, the epithelial cells interact with the cells of suitable for studies of epithelial regeneration and wound heal the mucosa-associated immune system. ing and for drug screening. 0047 Intestinal epithelial cells possibly have an important role in the pathogenesis of chronic inflammatory intestinal 0054) The S3 Guideline “Diagnosis and Therapy of diseases. The main model for the onset of chronic inflamma Crohn's disease summarizes the results (on the treatment of tory intestinal diseases describes the following scenario: a the aforesaid diseases) of an evidence-based consensus con defect in the structural integrity of the intestinal epithelium ference of the German Society for Digestive and Metabolic leads to an invasion of antigens from the intestinal lumen. In Diseases with the competence field Chronic inflammatory genetically predisposed patients, this process can trigger a intestinal diseases (Z. Gastroenterol 2008; 46: 1094-1146). chronic inflammation through activation of the mucosa-asso For the therapy of Such diseases, inter alia budesonide, sys ciatedlymphatic tissue. A disorder of the cell-cell contact due temically active steroids, Sulfasalazine, azathioprine/6-mer to genetic modification of the N-adherin or keratin 8 triggers captopurine, methotrexate and anti-TNF-alpha antibodies a chronic intestinal inflammation. Epithelial cells possess a have until now been used. large number of receptors for signal uptake. These in particu lar include receptors for the recognition of bacterial motifs, 0055. Overall, however, there is still a need for suitable so-called pattern recognition receptors. uses for the prophylaxis and/or treatment of inflammation. US 2013/025 1730 A1 Sep. 26, 2013

SUMMARY OF THE INVENTION BRIEF DESCRIPTION OF THE DRAWINGS 0056. Object of the present invention is a compound of the 0073. The present invention will be explained in greater formula (X) detail with reference to the accompanying drawings in which 0074 FIGS.1a and 1b are chromatograms of the invention according to Example 4, (X) 0075 FIG.2a is a graph showing test results of the inven tion according to Example 1, 0076 FIG.2b is a graph showing test results of the inven tion according to Example 4, 0077 FIG.3a is a graph showing test results of the inven tion according to Example 1, 0078 FIGS. 3b and 3c are graphs showing test results of the invention according to Example 4. 007.9 FIG. 3d is a graph showing test results of the inven tion according to Example 2, and 0080 FIG. 3e is a graph showing test results of the inven or any salt of a compound of the formula (X) or any mixture tion according to Example 3. containing or consisting of two or more different compounds of the formula (X), two or more different salts of compounds DESCRIPTION OF THE PREFERRED of the formula (X) or one or more different compounds of the EMBODIMENTS formula (X) and one or more different salts of compounds of I0081 Preferably the method for the prophylaxis and/or the formula (X), wherein for treatment of inflammation is 0057 R1, R2 and R3 independently of one another in I0082 (a) a method for the prophylaxis and/or treatment of every compound of the formula (X) the following applies: chronic inflammatory diseases, in particular intestinal dis 0058. R1 means hydrogen or methyl, eases, 0059 R2 means an organic residue with 5 carbon atoms and/or and one oxygen atom or none and I0083) (b) a method for strengthening damaged or undam 0060 R3 means an organic residue with 10 carbon atoms aged skin, in particular mucosa, and one or more oxygen atoms, and/or 0061 or 0084 (c) a method for reducing tissue damage, in particu 0062 R1 and R2 together with the carbon atoms in posi lar tissue damage in the intestine, tions 4 and 5 and the oxygen atom bound to the carbon and/or atom in position 4 form a ring and comprise 5 carbonatoms I0085 (d) a method for recreating a normal cellular com and one oxygen atom or none, and position in the intestine, 0063 R3 means an organic residue with 10 carbon atoms and/or and one or more oxygen atoms, I0086 (e) a method for recreating or stabilizing the func for use in a method for the prophylaxis and/or treatment of tion of skin, in particular of mucosa. inflammation, in particular of inflammation of the (human or animal) skin, in particular in a method Preferred Compounds of Formula X 0064 for reducing the release of TNF-alpha, and/or I0087 Particularly advantageous and therefore preferred 0065 for reducing the release of an interleukin, prefer according to the invention is a use as described above, ably of IL-1, IL-6 and/or IL-8, and/or wherein for the groups R1,R2 and R3 in the compound of the 0.066 for reducing the release of a prostaglandin, pref formula (X) or independently of one another in one, several or erably of PGE2, and/or all, preferably all, compound(s) of the formula (X) the fol 0067 for reducing the release of interferon-gamma and/ lowing applies: or NF-kB, 0088 R3 means particularly preferably in a method

0068 for reducing the release of TNF-alpha, and/or 0069 for reducing the release of an interleukin, prefer ably of IL-1, IL-6 and/or IL-8, and/or 0070 for reducing the release of a prostaglandin, pref erably of PGE2. 0071 Essentially therefore, the present invention relates to the aforementioned compounds, salts or mixtures thereof wherein the dotted line which links the carbonatoms des as anti-inflammatory active substances. ignated as B and C means that a single bond or a double 0072 For the term “skin', the aforesaid respectively bond is present between these carbon atoms, and applies. The skin to be treated according to the invention is the dotted line which links the carbon atoms designated as thus preferably human or animal external skin (in the conven E and G means an individual double bond, which is posi tional sense) and/or a mucous membrane, in particular the tioned either between the carbonatoms designated as F and oral mucosa, the gastric mucosa and/or the intestinal mucosa, G or between the carbon atoms designated as E and F. in particular for the prophylaxis and/or treatment of one or I0089 R7, for the case where the double bond is positioned more of the diseases or symptoms described above. between the carbon atoms designated as E and F, means a US 2013/025 1730 A1 Sep. 26, 2013

hydroxy group or, for the case where the double bond is -continued positioned between the carbon atoms designated as F and Erionic acid C (3) G, is absent, 0090 R5 and R6 mean a hydrogen atom and a hydroxy group or together mean an oxygen atom, the dashed line marks the bond which links R3 with the carbon atom in position 3; 0091 R1 means hydrogen or methyl and 0092 R2 means Erionic acid D (4)

wherein R4 means hydrogen or a hydroxy group and the dashed line marks the bond which links R2 with the carbon atom in position 5 or 0093 R1 and R2 together mean

Erionic acid E (5)

wherein the dashed line (a) marks the bond which links the tertiary carbon atom with the oxygen atom bound to the carbonatom in position 4 and the dashed line (b) marks the bond which links the secondary carbon atom with the car bon atom in position 5. 0094 Particularly preferable is a use according to the invention (as described above), wherein one, several or all compound(s) of the formula (X) is selected or are each Eriolic acid A (7) selected independently of one another from the group con sisting of the following compounds (1) to (10):

Erionic acid A (1)

Erionic acid B (2)

Eriolic acid C (9) US 2013/025 1730 A1 Sep. 26, 2013

-continued Santa to be used according to the invention are particularly Eriolic acid D (10) well Suited for use as anti-inflammatory active Substances. 0108. Herba Santa (also Yerba Santa, mountain balm) in general designates Eriodictyon ssp., in particular Eriodictyon Californicum (H. & A.) Torr and Eriodictyon angustifolium (from the Hydrophyllaceae family). Herba Santa foliage has already long been used as a medicinal plant on account of its medicinal action. Traditionally, the plants, which were origi nally found in Mexico and the west of the USA, were used by American indigenous inhabitants and later by Spanish settlers (Heinsen, 1972: Munz, 1973; Barrett and Gifford, 1933; 0095 Erionic acid A corresponds to: 4-hydroxy-3-((E)-7- Immel, 2006). The antibacterial action of extracts from Eri hydroxy-3,7-dimethyl-4-oxo-oct-5-enyl)-5-((E)-4-hy Odictyon Californicum was described by Salle et al. in 1951 droxy-3-methyl-but-2-enyl)-benzoic acid (1) (Arch. Biochem. Biophys. 1951, 32, 121-123). The main 0096 Erionic acid B corresponds to: 3-hydroxy-8-((E)-7- Substances contained in Eriodictyon sp. include various fla hydroxy-3,7-dimethyl-4-oxo-oct-5-enyl)-2,2-dimethyl Vanones, inter alia homo-eriodictyol. hesperetin, Sterubin, chroman-6-carboxylic acid (2) chrysoeriol and luteolin (Hadleyy and Gisvold, 1942: Ley et 0097. Erionic acid C corresponds to: 3-(3,7-dimethyl-4- al., J. Agric. Food Chem., 2005). The different biological oxo-oct-6-enyl)-4-hydroxy-5-(E)-4-hydroxy-3-methyl actions of Herba Santa were previously mainly attributed to but-2-enyl)-benzoic acid (3) the flavanones contained, the composition and structures 0098 Erionic acid D corresponds to: 8-((E)-3,7-dimethyl whereofhad already been studied. Scarcely anything is so far 4-oxo-oct-5-enyl)-3-hydroxy-2,2-dimethyl-chroman-6- known in the literature concerning the properties of the com carboxylic acid (4) ponents from Herba Santa which do not have a flavanoid 0099 Erionic acid E corresponds to: 4-hydroxy-3-((E)-7- structure. In particular, nothing is known concerning an anti hydroxy-3,7-dimethyl-4-oxo-oct-5-enyl)-5-(3-methyl inflammatory action of the compounds to be used according but-2-enyl)-benzoic acid (5) to the invention. The compounds (1) to (10) also occurring in 0100 Erionic acid F corresponds to: 3-(3,7-dimethyl-4- various Eriodictyon sp. were only recently described for the oxo-oct-6-enyl)-4-hydroxy-5-(3-methyl-but-2-enyl)-ben first time. Their capabilities as antioxidants are presented in Zoic acid (6) DE 10 2009 020729 A1. However, nothing was hitherto 0101 Eriolic acid A corresponds to: 3-((E)-4-hydroxy-3, known concerning (additional) anti-inflammatory properties. 7-dimethyl-octa-2,6-dienyl)-5-((E)-4-hydroxy-3-methyl but-2-enyl)-4-methoxy-benzoic acid (7) Hydroxyflavones 0102 Eriolic acid B corresponds to: 4-hydroxy-3-((E)-4- 0109 Particularly preferable according to the invention is hydroxy-3,7-dimethyl-octa-2,6-dienyl)-5-(3-methyl-but a mixture for use in a method for the prophylaxis and/or 2-enyl)-benzoic acid (8) treatment of inflammation (as described above), comprising a 0103 Eriolic acid C corresponds to: 4-hydroxy-3-((E)-4- compound of the formula (X), a salt of the formula (X) or a hydroxy-3,7-dimethyl-octa-2,6-dienyl)-5-((E)-4-hy mixture thereof (as respectively described above) and addi droxy-3-methyl-but-2-enyl)-benzoic acid (9) and tionally 0104 Eriolic acid D corresponds to: 3-((E)-4-hydroxy-3, 0110 a hydroxyflavone of the formula (Y) 7-dimethyl-octa-2,6-dienyl)-4-methoxy-5-(3-methyl-but 2-enyl)-benzoic acid (10).

0105. The benzoic acids of the formula (X) to be used (Y) according to the invention can contain one or more asymmet ric carbon atoms. These can each be present in the (R) or (S) configuration. These stereoisomers can be present as enanti omers, diastereomers or epimers, in particular as (R), (S), (R,R), (R.S.). (S,R) or (S,S)-configured compounds or as any mixture of these compounds, for example as a racemate, or also as any mixture of the corresponding diastereomers. 0106 Particularly preferable according to the invention is a mixture (as described above), containing or consisting of two or more different compounds of the formula (X), prefer ably of two, three, four, five, six, seven, eight, nine or ten different compounds of the formula (X), preferably selected 0.111 or a salt of a hydroxyflavone of the formula (Y) from the group consisting of the compounds (1) to (10). 0112 or a mixture containing or consisting of two or more different hydroxyflavones of the formula (Y), two Herba Santa or more different salts of hydroxyflavones of the formula 0107 The aforementioned compounds (7) and (9) are two (Y) or one or more different hydroxyflavones of the commercially available compounds (for example Supplied by formula (Y) and one or more different salts of hydroxy the firm Ambinter) identified in Herba Santa. However no flavones of the formula (Y), references to an anti-inflammatory action of these com wherein for Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8 and Q9 inde pounds are known in the State of the art. It was particularly pendently of one another in each hydroxyflavone of the for surprising that the compounds of the formula (X) from Herba mula (Y) the following applies: US 2013/025 1730 A1 Sep. 26, 2013

Q1 to Q9 independently of one another mean hydrogen -continued atoms, hydroxy groups, methyl, ethyl, 1-propyl, methoxy, (12) ethoxy, 1-propyloxy or 2-propyloxy groups, with the proviso OH that at least one of the residues Q1 to Q9 represents a hydroxy grOup, HO and wherein preferably the following applies: OH Q2, Q4, Q5, Q8 and Q9 represent hydrogen atoms, Q1, Q3 and Q6 independently of one another mean hydrogen coOH O atoms, hydroxy or methoxy groups, with the proviso that at least one of the residues Q1 and Q3 represents a hydroxy Eriodictyol grOup, (13) OH and Q7 represents a hydroxy group. 19 OH 0113. The hydroxyflavones of the formula (Y) can be present as mono- or (in the case of several hydroxy groups) multivalent anions, wherein as counter-cations the singly positively charged cations of the first main and transition OH O group, the ammonium ion, a trialkylammonium ion, the Eriodictyol-7-methyl ether divalently charged cations of the second main and transition (14) group, and the trivalent cations of the 3" main and transition OH group, preferably, Na', K", NH, Ca", Al" and Zn", are used. HO 0114. The hydroxyflavones of the formula (Y) can be o1 present as (2S) or (2R) enantiomers or as a mixture of both. Preferably the hydroxyflavones of the formula (Y) are present as the (2S) enantiomer or as a mixture enriched in (2S) enan tiomer. OH O Homoeriodictyol 0115 Without thereby limiting the invention, the follow ing compounds may be mentioned by way of example: 2-(4- (15) hydroxyphenyl)-5,7-dihydroxychroman-4-one (naringenin), OH 2-(3,4-dihydroxyphenyl)-5,7-di hydroxychroman-4-one (eriodictyol), 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-meth HO O O oxychroman-4-one (eriodictyol 7-methyl ether), 2-(3,4-dihy OH droxyphenyl)-7-hydroxy-5-methoxychroman-4-one (eriod ictyol 5-methyl ether), 2-(4-hydroxy-3-methoxyphenyl)-5,7- dihydroxychroman-4-one (homoeriodictyol) and 2-(3- O hydroxy-4-methoxyphenyl)-5,7-dihydroxychroman-4-one C (hesperetin), (2S) or (2R) enantiomers thereof or mixtures Eriodictyol-5-methyl ether thereof, and mono- or multivalent phenolate salts thereof with Na', K", NH, Ca, Mg" or Al" as counter-cations. (16) 0116. The structures of preferred examples of hydroxyfla vones of the formula (Y) are shown below (see compounds (11) to (16)): HO OH

(11) OH coOH O HO O Hesperetin

0117 Particularly preferable is a mixture (as described OH O above) comprising one, several or all compounds of the for Naringenin mula (Y) selected from the group consisting of homoeriod ictyol. Sterubin, eriodictyol. hesperetin, chrysoeriol and luteolin. US 2013/025 1730 A1 Sep. 26, 2013

0118 Particularly preferably, such a mixture contains at Preparations least homoeriodictyol as a compound of the formula (Y). 0.126 The present invention also relates to preparations, in particular preparations used for food or enjoyment, pharma Mixtures ceutical preparations, cosmetic preparations or dermatologi 0119. According to a preferable embodiment of the cal preparations for use in a method for the prophylaxis and/or present invention, a mixture (as described above) is provided treatment of inflammation, comprising a compound, a salt or for the use, wherein a mixture as defined above, for use in a method for the pro I0120 the proportion of the total quantity of compounds phylaxis and/or treatment of inflammation. of the formula (X) and salts of compounds of the formula I0127 Preferably these are preparations for the prophy (X) in the mixture, based on the total weight of the laxis and/or treatment of inflammation of the skin (as mixture, is 1 to 99 wt.%, preferably 10 to 99 wt.%, described above), in particular in a method particularly preferably 20 to 80 wt.%, and/or 0.128 for reducing the release of TNF-alpha, and/or I0121 the proportion of the total quantity of compounds 0.129 for reducing the release of an interleukin, prefer of the formula (Y) and salts of compounds of the formula ably of IL-1, IL-6 and/or IL-8, and/or (Y) in the mixture, based on the total weight of the 0.130 for reducing the release of a prostaglandin, pref mixture, is 1 to 99 wt.%, preferably 10 to 99 wt.%, erably of PGE2, and/or particularly preferably 20 to 80 wt.%. 0131 for reducing the release of interferon-gamma and/ wherein preferably the proportion of the total quantity of or NF-kB, compounds of the formula (X), compounds of the formula particularly preferably in a method (Y), salts of compounds of the formula (X) and salts of compounds of the formula (Y) in the mixture, based on the 0.132 for reducing the release of TNF-alpha, and/or total weight of the mixture, is 0.0001 to 100 wt.%, preferably 0.133 for reducing the release of an interleukin, prefer 0.001 to 100 wt.%, particularly preferably 0.1 to 90 wt.%, ably of IL-1, IL-6 and/or IL-8, and/or more preferably 1 to 90 wt.%. According to an especially 0.134 for reducing the release of a prostaglandin, pref preferred embodiment, the proportion is 10 to 90 wt.%, in erably of PGE2. particular 25 to 90 wt.% (preferably up to 100 wt.%), more I0135 Preferably here this is also preferably 45 to 90 wt.% (preferably up to 100 wt.%). 0.136 (a) a method for the prophylaxis and/or treatment of 0122) Surprisingly, in our own studies it was found that chronic inflammatory diseases, in particular intestinal dis certain extracts prepared from Herba Santa foliage or frac eases, and/or tions therefrom are particularly suitable for treating inflam 0.137 (b) a method for strengthening damaged or undam matory processes, for example with inflammation in the gas aged skin, in particular mucosa, and/or trointestinal tract or gingivitis, and/or preventing these. 0.138 (c) a method for reducing tissue damage, in particu Hence, according to a further aspect of the present invention, lar tissue damage in the intestine, and/or a mixture is stated for the use described according to the 0.139 (d) a method for recreating a normal cellular com invention, wherein the mixture comprises a plant extract or position in the intestine, and/or consists thereof, preferably an extract from Eriodictyon ssp., 0140 (e) a method for recreating or stabilizing the func particularly preferably an extract from Eriodictyon Californi tion of skin, in particular of mucosa. cum and/or Eriodictyon angustifolium, wherein the propor 0141 Moreover, the aforesaid also respectively applies, in tion of the total quantity of compounds of the formula (X) and particular as regards the contained compounds of the formula salts of compounds of the formula (X) in the mixture, based (X) or salts thereof and the optionally contained compounds on the total weight of the mixture, is preferably 0.1 to 100 wt. of the formula (Y) or salts thereof. %, more preferably 1 to 100 wt.%, particularly preferably 10 0.142 Preferably a preparation described above contains a to 100 wt.%, and more preferably from 10 to 90 wt.%. mixture preferred according to the invention (as described 0123 Particularly preferably, the ratio of the total quantity of compounds of the formula (X) and salts of compounds of above). the formula (X) to the total quantity of compounds of the Preparation of the Mixtures formula (Y) and salts of compounds of the formula (Y) in a mixture described herein usable according to the invention 0.143 A mixture according to the invention or a mixture lies in the range from 0.00001:1 to 1:0.00001, in particular in usable according to the invention, preferably a mixture the range from 0.0001:1 to 1:0.0001, preferably in the range described above as preferable, is preferably producible by a from 0.001:1 to 1:0.001, preferably in the range from 0.01:1 method with the following steps: to 1:0.01, particularly preferably in the range from 0.1:1 to 0144 (a) Extraction of plant material from Eriodictyon 1:0.1, and more preferably in the range from 0.5:1 to 1:0.5, ssp., preferably from Eriodictyon Californicum and/or Eri each based on the weight. Odictyon angustifolium, so that a mixture is formed which 0.124. According to a preferable embodiment of the contains compounds of the formula (X), optionally com present invention, a mixture described herein comprises as pounds of the formula (Y) and other extracted compounds, compounds of the formula (Y) homoeriodictyol and sterubin and or salt(s) thereof. Here, as regards preferable quantity data 0145 (b) Concentration of extracted compounds of the and ratios, the aforesaid respectively applies. formula (X) and/or salts of the extracted compounds of the 0.125. In a preferable embodiment of such a mixture, the formula (X) and optionally compounds of the formula (Y) mixture contains a total quantity of homoeriodictyol and and/or salts of the extracted compounds of the formula (Y) sterubin (and/or salts thereof) which is greater than the total in the mixture by partial or complete removal of other quantity of compounds of the formula (X) (and optionally extracted compounds and optionally removal of extract salts thereof). ants and/or solvents, US 2013/025 1730 A1 Sep. 26, 2013 preferably so that the proportion of the total quantity of com erionic acid fraction from Eriodictyon angustifolium extract; pounds of the formula (X) and salts of compounds of the each after fractionation over Sephadex LH-20). formula (X) in the mixture based on the total weight of the 0160. In the light of the above explanations, a preparation mixture is 0.1 to 100 wt.%, more preferably 1 to 100 wt.%, according to the invention or a mixture according to the particularly preferably 10 to 100 wt.%, more preferably from invention (as respectively described above) preferably com 10 to 90 wit. 96. prises or consists of (i) Herba Santa foliage, (ii) an optionally 0146 Preferably the plant material here is selected from concentrated extract prepared therefrom or (iii) a fraction the group consisting of thereof. 0147 Eriodictyon altissimum P. V. Wells—Indian Knob mountain balm Additives for the Mixtures 0148 Eriodictyon angustifolium Nutt. Narrow leaved Yerba Santa 0.161. In the mixtures or preparations according to the 0149 Eriodictyon Californicum (Hook. & Arm.) invention, as well as the components described above, one or Torr.—California Yerba Santa more further substances can be contained. Preferably one or more (further) substances which are suitable for influencing 0150 Eriodictyon capitatum Eastw.—Lompoc Yerba inflammatory states of the skin, in particular for prophylactic Santa and/or therapeutic uses as described above, are contained. 0151 Eriodictyon crassifolium Benth. Thick-Leaved Furthermore, one or more substances for the treatment of a Yerba Santa deficiency phenomenon arising during inflammation of the 0152 Eriodictyon tomentosum Benth skin (in particular a deficiency of potassium, Sodium, iron, 0153 Eriodictyon traskiae and calcium, Vitamin D and/or folic acid) can be contained. 0154 Eriodictyon trichocalyx (Syn.: Eriodictyon lana 0162. In the mixtures or preparations according to the tum (Brand) Abrams)—Hairy Yerba Santa invention, one or more further components selected from the 0155 According to a preferable aspect of the present following group are preferably (also) contained: probiotic invention, a mixture described herein or a preparation bacteria (e.g. lactobacilli, bifidobacteria and enterococci), described herein comprises or consists of an appropriately prebiotics (e.g. inulin and fructooligosaccharides), Synbiotics concentrated extract from Herba Santa, preferably from plant (pro- and prebiotics), ballast Substances (e.g. cellulose, material as described above. starch, resistant starch and fibres, such as for example apple 0156. In the context of the present invention, an extract fibres), whey proteins, soya proteins, minerals (in particular from fresh or dried Herba Santa plants or plant parts is pref Ca, Mg, with a combination of Ca, Mg and inulin being erable, particularly preferably from plants or plant parts with particularly preferable), tocopherols (e.g. vitamin E. Vitamin a solids content of 90 wt.% or more. Particularly preferably, Eacetate), Vanilla, Vanilla extracts, omega-3 fatty acids (pref the extract is from above-ground plant parts, in particular erably fish oil), citrus, apple, grape seed, green tea, rosemary, from leaves, buds, stems, bark, flowers and/or fruit of E. tarragon, thyme, horseradish and mace extracts, tannins, angustifolium or E. Californicum. tomato, melon and rose hip extracts (in particular lycopene 0157 Extracts from Herba Santa foliage (as described containing extracts), betacarotene; aubergines, rhubarb, red above) can be obtained by extraction methods known perse onions, red cabbage, black carrot, Superfruits, in particular from the fresh or dried foliage of the plants. These for agai, noni, goji, pomegranate, mangosteen, currrants, Straw example include maceration or percolation. As the extraction berries, aronia, blueberries and/or elderberries, preferably in medium, for example water and ethanol or mixtures thereof the form of dried fruit, extracts or fruit preparations; soya can be used. Instead of ethanol, methanol and other water isoflavones, nonsteroidal antiinflammatory drugs, antibiot soluble solvents can also be used. Likewise, ethyl acetate can ics, budesonide, systemically active steroids, Sulfasalazine, be used as a solvent. Selection of the temperature and azathioprine/6-mercaptopurine, methotrexate, anti-TNF-al mechanical disintegration of the fruit can promote the extrac pha antibodies, bisabolol, sodium laurylsulphate, chlorhexi tion. According to the state of the art, the mechanical disin dine, metal fluorides (e.g. aluminium and tin fluoride), tegration of the dried foliage e.g. with stirrers, homogenizers organic and inorganic fluorides, flavourings, essential oils, or ultrasound is also advisable. Further, other extraction cooling active Substances, in particular menthol, extracts or promoting Substances, such as acids, bases and enzymes, can pure Substances from eucalyptus, thyme, wintergreen, spear be used. mint and peppermint. 0158. In the context of the present text, the term “Herba Santa foliage in particular comprises leaves, buds, bark, Final Preparations for Customers flowers, fruit and stems of Eriodictyon angustifolium, E. Cali fornicum, E. trichocalyx, E. traskiae, and E. crassifolium. 0163 Preparations according to the invention (in particu 0159. The identification and quantification of flavones and lar the preparations designated above as preferable) are pref bisprenylated benzoic acid derivatives in different Eriodic erably selected from the group consisting of tyon sp. can be effected by means of RP-HPLC-UV/Vis and 0164. Fruit juice-containing drinks; vegetable juice RP-HPLC-MS/MS after the methanolic extraction, as per containing drinks; bakery products; confectionery; formed in the context of our own studies. The flavonoid Snacks; instant products; soups; sauces; spice mixtures; contents, or contents of bisprenylated benzoic acid deriva ice cream; fruit preparations; desserts; dairy products; tives can be determined by means of external calibration with Soya products; cereals; food Supplements, medicinal use of standard substances. The appended FIGS. 1 a. and 1 b products and pharmaceutical products. respectively show by way of example the flavonoid or erionic/ 0.165 Fruit juice-containing drinks here are in particu eriolic acid profile of extracts studied (FIG.1a: LC-MS chro lar fruit juices and smoothies (whole fruit drinks). Veg matogram of the flavonoid fraction from Eriodictyon angus etable juice-containing drinks are in particular juices of tifolium extract; FIG. 1b: LC-MS chromatogram of the red beet and black carrot. US 2013/025 1730 A1 Sep. 26, 2013 10

0166 Bakery products are in particular cakes, waffles non-foaming or after-foaming), skin care products (as and biscuits. described above), as foot care products (including kera 0.167 Confectionery is in particular lozenges and chew tolytic agents and deodorants), as insect repellents, as ing gums, fruitgums, chewing Sweets, (breath freshen Sunscreen agents, as self-tanning agents and/or afterSun ing) Sweets, boiled Sweets, hard caramels, chocolate preparations, skin care products as shaving products or creams, Sweets and chocolate. after-shave, as depilatory agents, as hair care products 0168 Instant products are in particular instant meals Such as for example shampoo (including shampoo for and other instant products, e.g. drink powders and gran normal hair, for greasy hair, for dry, stressed (damaged) ules. hair, 2-in-1 shampoo, antidandruff shampoo, baby 0169 Fruit preparations are in particular jams, pre shampoo, shampoo for dry scalp, shampoo concentrate), serves and fruit sauces. conditioner, hair mask, hair lotion, hair conditioner, hair 0170 Desserts are in particular puddings and jellies. cream, pomade, permanent wave and fixing agents, hair 0171 Dairy products comprise in particular quark, straighteners (straighteners, relaxers), hair setting yoghurt, milk drinks and whey preparations. lotions, styling aids (e.g. gel or wax); bleaching agents, 0172 Cereals are in particular cornflakes, muesli and hair dyes such as for example temporary, direct and muesli bars. semipermanent hair dyes, permanent hair dyes), skin 0173 Further preferable preparations, in particular care products as decorative toiletry products. Such as for food Supplements, medicinal products and pharmaceu example nail care products (nail varnish and nail varnish tical products, are remover), decorative cosmetics (e.g. powder, eye 0.174 Solid galenical forms (such as for example tablets shadow, eye pencil, lipstick), skin care products as (with and without coating, with and without modified deodorant and/or antiperspirant; mouthwash and oral release), Sugar-coated tablets (with and without coating, waterjet, and with and without modified release), capsules (soft or 0180 Oral care products (e.g. toothpaste, tooth cream, hard gelatine capsules with and without modified tooth gel, tooth powder, tooth cleaning fluid or foam, release) granules (with and without modified release), mouthwash, tooth cream and mouthwash as 2-in-1 prod powders (with and without modified release), Supposi uct, mouth spray, dental floss or dental care chewing tories (with and without coating, with and without modi gum). Such oral or dental care products as a rule contain fied release), lozenges and chewing gums), abrasive systems (abrasive or polishing ingredients), 0.175 Liquid forms (such as for example solutions, sus Such as silicates, calcium carbonate, calcium phosphate, pensions, emulsions, syrups (colloquially cough syrup), aluminium oxide and/or hydroxyapatite, Surfactant Sub mouthwashes, gargle solutions, throat sprays or nasal stances, e.g. sodium laurylsulphate, sodium laurylsarco sprays, nasal drops, nasal rinse solutions, nasal powders, sinate and/or cocamidopropyl betaine, humectants such nasal ointments or ear drops, ear sprays, ear rinse Solu as glycerol and/or Sorbitol, thickeners, e.g. carboxym tions, ear powders and aural tampons), ethylcelluloses, polyethylene glycols, carrageenan and/ 0176) Semisolid forms (such as for example hydropho or Laponite R, SweetenerS Such as saccharin, flavour/ bic ointments including for example: hydrocarbon gels, taste correctants for unpleasant taste sensations, taste lipogels, silicone gels, oleogels and water-absorbing modulating Substances (e.g. inositol phosphate, ointments including for example absorption bases, nucleotides, e.g. guanosine monophosphate, adenosine hydrophilic ointments, hydrophilic gels (hydrogels) or monophosphate or other Substances, e.g. sodium pastes, glutamate or 2-phenoxypropionic acid), cooling active 0177. Inhalants (such as for example compressed gas Substances, e.g. mentholderivatives (e.g. L-menthyllac dispenser inhalers, powder inhalers, inhalers with atom tate, L-menthylalkyl carbonates, menthone ketals), ici isers, and inhalation concentrates for inhalation), lin and icilin derivatives, stabilizers and active sub 0.178 Active substance-containing plasters or other Stances, C.2. Sodium fluoride, Sodium therapeutic systems and monofluorophosphate, tin difluoride, quaternary ammo 0179 Cosmetic and/or dermatological preparations, nium fluorides, Zinc citrate, Zinc Sulphate, tin pyrophos which (except for the Substances to be used according to phate, tin dichloride, mixtures of various pyrophos the invention) are constituted as usual and are used for phates, triclosan, cetylpyridinium chloride, aluminium cosmetic, in particular dermatological Sun protection, lactate, potassium citrate, potassium nitrate, potassium for the treatment, care and cleansing of the skin and/or chloride, strontium chloride, hydrogen peroxide, fla the hair or as a make-up product in decorative cosmetics. vourings, sodium bicarbonate and/or odour correctants, Accordingly, such preparations can be present as for and example cleaning agents such as for example soap, Syn 0181 Chewing gums or dental care gums consisting of det, liquid wash, shower and bath preparation, skin care a chewing gum base containing elastomers, e.g. polyvi agents such as for example emulsion (as Solution, dis nyl acetates (PVA), polyethylenes, (low or medium persion, Suspension; cream, lotion or milk depending on molecular weight) polyisobutenes (PIB), polybuta production method and ingredients of the type W/O, dienes, isobutene-isoprene copolymers, polyvinyl ethyl O/W or multiple emulsion, PIT emulsion, emulsion ethers (PVE), polyvinyl butyl ethers, copolymers of foam, micro- or nanoemulsion, Pickering emulsion), vinyl esters and vinyl ethers, styrene/butadiene copoly ointment, paste, gel (including hydro-, hydrodispersion mers (SBR) or vinyl elastomers, e.g. based on vinyl and oleogel), alcoholic or aqueous/alcoholic solution, acetate/vinyl laurate, vinyl acetate/vinyl Stearate or eth oil, toner, balsam, serum, powder, wipe, Eau de Toilette, ylene/vinyl acetate, and mixtures of the said elastomers Eau de Cologne, perfume, wax, including the presenta such as for example described in EP 0242325, U.S. Pat. tion as Stick, roll-on, (pump-)spray, aerosol (foaming, No. 4,518,615, U.S. Pat. No. 5,093,136, U.S. Pat. No. US 2013/025 1730 A1 Sep. 26, 2013 11

5,266,336 U.S. Pat. No. 5,601,858 or U.S. Pat. No. malic acid, acetic acid, citric acid, tartaric acid, phosphoric 6,986,709. In addition, chewing gum bases contain fur acid), bitter Substances (e.g. quinine, caffeine, limonin, ama ther ingredients, e.g. (mineral) fillers (e.g. calcium car rogentin, humolone, lupolone, catechins, tannins), mineral bonate, titanium dioxide, silicon dioxide, talc, alu salts (e.g. sodium chloride, potassium chloride, magnesium minium oxide, dicalcium phosphate, tricalcium chloride, sodium phosphate), Substances preventing enzy phosphate, magnesium hydroxide and mixtures thereof, matic browning (e.g. Sulphite, ascorbic acid), essential oils, plasticizers (e.g. lanolin, Stearic acid, Sodium Stearate, plant extracts, natural or synthetic dyes or pigments (e.g. ethyl acetate, diacetin (glycerol diacetate), triacetin carotenoids, flavonoids, anthocyans, chlorophyll and deriva (glycerol triacetate) and triethyl citrate), emulsifiers tives thereof), spices, trigeminally active Substances or plant (e.g. phosphatides, such as lecithin and mono and dig extracts, containing Such trigeminally active Substances, lycerides of fatty acids, e.g. glycerol monostearate), cooling active Substances such as for examplementhol, men antioxidants, waxes (e.g. paraffin waxes, candelilla thol derivatives (e.g. L-menthol, L-menthyl lactate, L-men waxes, carnauba wax, microcrystalline waxes and poly thyl glutarate, L-menthyl Succinate) or cubebol, synthetic, ethylene waxes), fats or fatty oils (e.g. hardened (hydro natural or nature-identical flavourings or aromatic Substances genated) plant or animal fats) and mono, di- or triglyc and odour correctants. erides. 0186 Preparations according to the invention, used in par 0182 Preferable preparations according to the invention ticular for food or enjoyment can additionally contain one or used for food or enjoyment are: more taste correctants, preferably selected from the following 0183 Confectionery such as for example lozenges and list: nucleotides (e.g. adenosine 5'-monophosphate, cytidine chewing gums, fruitgums, chewing Sweets, (breath freshen 5'-monophosphate) or pharmaceutically acceptable salts ing) Sweets, boiled Sweets, hard caramels, chocolate creams, thereof, lactisols, sodium salts (e.g. sodium chloride, sodium Sweets and chocolate, bakery products such as cakes, waffles lactate, Sodium citrate, Sodium acetate, Sodium gluconate), and biscuits, Snacks, instant meals and other instant products further hydroxy-flavanones (e.g. eriodictyol, homoeriodic (drink powders and granules), ice cream, fruit preparations tyol or sodium salts thereof), in particular according to US (jams, preserves and fruit sauces), desserts (puddings, jel 2002/0188019, hydroxybenzamides as per DE 10 2004 041 lies), dairy products (quark, yoghurts, probiotic yoghurts, 496 (e.g. 2,4-dihydroxybenzoic acid vanillylamide, 2,4-dihy milk drinks, whey preparations) and cereals (cornflakes, droxybenzoic acid N-(4-hydroxy-3-methoxybenzyl)amide, muesli and muesli bars). 2,4,6-trihydroxybenzoic acid N-(4-hydroxy-3-methoxyben 0184 Especially preferred preparations according to the Zyl)-amide, 2-hydroxybenzoic acid N-4-(hydroxy-3-meth invention used for food or enjoyment are fruit gums, fruit oxybenzyl)amide, 4-hydroxybenzoic acid N-(4-hydroxy-3- preparations (jams, preserves and fruit sauces), dairy prod methoxybenzyl)amide, 2,4-dihydroxybenzoic acid N-(4- ucts (quark, yoghurts, probiotic yoghurts, milk drinks, whey hydroxy-3-methoxybenzyl)amide monosodium salt, 2.4- preparations) and cereals (cornflakes, muesli and muesli dihydroxybenzoic acid N-2-(4-hydroxy-3-methoxyphenyl) bars), wherein in turn the dairy products yoghurts, probiotic ethylamide, 2,4-dihydroxybenzoic acid N-(4-hydroxy-3- yoghurts and milk drinks are most preferred. ethoxybenzyl)-amide, 2,4-dihydroxybenzoic acid N-(3,4- dihydroxybenzyl)amide and 2-hydroxy-5-methoxy-N-(2-(4- Additives for the Preparations hydroxy-3-methoxyphenyl)ethylamide (aduncamide), 0185. As further components for preparations according 4-hydroxybenzoic acid Vanillylamide), bitter-masking to the invention used in particular for food or enjoyment, hydroxydeoxybenzoins according to WO 2006/106023 and normal primary, auxiliary and additive Substances for food or the documents based thereon (Symrise) (e.g. 2-(4-hydroxy luxury consumables can be used, e.g. water, mixtures of fresh 3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone, or processed, plant or animal primary or raw Substances (e.g. 1-(2,4-dihydroxyphenyl)-2-(4-hydroxy-3-methoxy-phenyl) raw, roast, dried, fermented, Smoked and/or boiled meat, ethanone, 1-(2-hydroxy-4-methoxyphe-nyl)-2-(4-hydroxy bones, cartilage, fish, vegetables, fruit, spices, nuts, vegetable 3-methoxyphenyl)ethanone), amino acids (e.g. gamma-ami or fruit juices or pastes or mixtures thereof), digestible or nobutyric acid as per WO 2005/096841 for reduction or non-digestible carbohydrates (e.g. amylose, amylopectin, masking of an unpleasant taste sensation Such as bitterness), inulin, Xylans, cellulose), natural or hardened fats (e.g. tallow, malic acid glycosides as per WO 2006/003107, salty-tasting lard, palm fat, coconut fat, hardened plant fat), oils (e.g. mixtures as per WO 2007/045566, diacetyltrimers as per WO Sunflower oil, peanut oil, maize oil, olive oil, fish oil, Soya oil, 2006/058893, divanillin, mixtures of whey proteins with leci sesame oil), fatty acids or salts thereof (e.g. potassium Stear thins and/or bitter-masking Substances such as gingerdiones ate), proteinogenic or non-proteinogenic amino acids and according to WO 2007/003527. related compounds (e.g. Y-amino-butyric acid, taurine), pep 0187 Preparations according to the invention used in par tides (e.g. glutathione), native or processed proteins (e.g. ticular for food or enjoyment can additionally contain one or gelatine), enzymes (e.g. peptidases), nucleic acids, nucle more alkamides, preferably selected from the group consist otides, taste correctants for unpleasant taste sensations, fur ing of 2E.4E-decadienoic acid N-isobutylamide (pellitorin), ther taste modulators for further, as a rule not unpleasant taste 2E.4Z-decadienoic acid N-isobutylamide (cispellitorin), sensations, other taste-modulating Substances (e.g. inositol 2Z.47-decadienoic acid N-isobutylamide, 2Z.4E-decadi phosphate, nucleotides such as guanosine monophosphate, enoic acid N-isobutylamide, 2E.4E-decadienoic acid adenosine monophosphate or other Substances Such as N-(2S)-2-methylbutyl)amide, 2E,4E-decadienoic acid Sodium glutamate or 2-phenoxypropionic acid), emulsifiers N-(2S)-2-methylbutylamide, 2E.4E-decadienoic acid (e.g. lecithins, diacylglycerols, gum Arabic), stabilizers (e.g. N-(2R)-2-methylbutylamide), 2E.4Z-decadienoic acid carrageenan, alginate), preservatives (e.g. benzoic acid, Sor N-(2-methylbutyl)amide, 2E.4E-decadienoic acid N-pip bic acid), antioxidants (e.g. tocopherol, ascorbic acid), chela eride (achilleamide), 2E.4E-decadienoic acid N-piperide tors (e.g. citric acid), organic or inorganic acidulants (e.g. (sarmentin), 2E-decenoic acid N-isobutylamide, 3E-de US 2013/025 1730 A1 Sep. 26, 2013

cenoic acid N-isobutylamide, 3E-nonenoic acid N-isobutyla where this comprises one, two, three, four, five, six, seven, mide, 2E,6Z.8E-decatrienoic acid N-isobutylamide (spilan eight, nine or all compounds (1) to (10) and also one, two, thol), 2E,6Z.8E-decatrienoic acid N-(2S)-2-methylbutyl) three, four, five or all compounds (11) to (16) or consists amide (homospilanthol), 2E,6Z.8E-decatrienoic acid thereof. Particularly preferable here is a mixture or a prepa N-(2R)-2-methylbutyl)amide, 2E-decen-4-ynic acid ration, which comprises all of the compound (1) to (16) or N-isobutylamide, 2Z-decen-4-ynic acid N-isobutylamide, consists thereof. sanshoole. 0188 Preparations according to the invention, used in par 0194 Such a mixture or preparation wherein one, several ticular for prophylaxis and Supplementation of food and for or all compounds of the group of the compounds (1) to (16) the therapy of disease states and for toiletries can preferably are components of a plant extract, preferably an extract from contain Substances or combinations of Substances from the eriodictyon ssp., particularly preferably an extract from eri following groups. Odictyon Californicum and/or eriodictyon angustifolium, is 0189 Fillers (e.g. cellulose, calcium carbonate), free-flow particularly preferable. and anticaking agents (e.g. talc, magnesium Stearate), coat ings (e.g. polyvinyl acetate phthalate, hydroxypropyl-meth 0.195. It was particularly surprising that the compounds of ylcellulose phthalate), disintegrants (e.g. starch, crosslinked the formula (X) to be used according to the invention or salts polyvinylpyrrolidone), plasticizers (e.g. triethylcitrate, dibu thereof can mediate or possess strong anti-inflammatory tyl phthalate) Substances for granulation (lactose, gelatine), effects. Compounds, salts, mixtures and preparations accord retardation (e.g. poly(meth)acrylic acid methyl/ethyl/2-trim ing to the invention (as respectively described above) are ethylaminoethyl ester copolymers in dispersion, vinyl advantageously capable of positively influencing inflamma acetate/crotonic acid copolymers) and compacting (e.g. tory parameters in monocytes. In cell models wherein irri microcrystalline cellulose, lactose), solvent, Suspension or tated and inflammatory phenomena of the mucous mem dispersion agents (e.g. water, ethanol), emulsifiers (e.g. cetyl branes, especially of gingiva and the gastrointestinal tract, are alcohol, lecithin), substances for modification of the rheo simulated, these exhibit an anti-inflammatory action. In par logical properties (silicon dioxide, Sodium alginate), Sub ticular, the following inflammatory parameters are positively stances for microbial stabilization (e.g. benzalkonium chlo influenced according to the invention: PGE2, IL-1, TNF, IL-6 ride, potassium Sorbate), preservatives and antioxidants (e.g. and IL 8, in particular PGE2. Appropriate experiments on this DL-alpha-tocopherol, ascorbic acid), Substances for modifi were performed as described in TS1 (see below, “Example cation of the pH (lactic acid, citric acid), propellant or inert TS: Test study”). Thus for example from a concentration of 1 gases (e.g. fluorinated chlorohydrocarbons, carbon dioxide), ug/ml, eriol-ferion-containing fractions already exhibit a colorants (iron oxides, titanium dioxide), ointment bases (e.g. highly significant action on Some of the abovementioned paraffins, beeswax), inter alia as described in the technical parameters. Concentrations of 10 g/ml and more are particu literature (e.g. Schmidt, Christin. Active and Auxiliary Sub larly suitable. A total extract from Herba Santa foliage which stances for Individual and Bulk Formulation, and Large-scale contains compounds usable according to the invention or Manufacture. 1999: Wissenschaftliche Verlagsgesellschaft individual extracts therefrom for example exhibits significant mbH Stuttgart or Bauer, Frömming Fuhrer. Textbook of Phar effects on individual parameters from a concentration of 1 maceutical Technology. 8" Edition, 2006. Wissenschaftliche ug/ml and highly significant effects up to 250 ug/ml. Verlagsgesellschaft mbH Stuttgart). 0190. Depending on the embodiment according to the 0196. For salts of compounds of the formula (X) usable invention and desired purpose, mixtures according to the according to the invention, that stated further above respec invention (as described above) can also contain one or more tively applies as regards the preferable meanings of the resi of the components mentioned above in connection with dues. The carboxylic acid group which is bound to the carbon preparations according to the invention. atom in position 1 (according to the numbering shown in formula (X)) is then present deprotonated. In addition, one or more hydroxy groups (if present) are optionally also present INDUSTRIAL APPLICATION deprotonated. Here, as well as the deprotonated compound(s) 0191) A further aspect of the present invention relates to a of the formula (X), a corresponding quantity of counter compound, a salt, a mixture or a preparation, as respectively cations are present, where these are preferably selected from described or defined above, for use in a method for the treat the group consisting of singly positively charged cations of ment of animal or human skin which requires treatment with the first main and transition group, ammonium ions, trialky anti-inflammatory active Substances. Regarding the selection lammonium ions, doubly positively charged cations of the of the compounds or the salts and the preferable composition second main and transition group and triply positively of the mixtures and preparations, the aforesaid respectively charged cations of the third main and transition group, and applies. mixtures thereof. The maximum degree of deprotonation of a 0.192 The compounds (1) to (16) described herein advan compound of the formula (X) on which such as salt is based tageously possess a particularly strong anti-inflammatory is found from the carboxyl group and the hydroxy groups of action. The compounds (1) to (16) are advantageously Suit this compound lying adjacent thereto. In turn, from the num able for Supporting the natural defence mechanisms against ber of deprotonated groups, the corresponding number of inflammatory processes in physiological systems (of people counter-cations is obtained (depending on their charge). Thus and animals). Further, these compounds advantageously for example for a compound of the formula (X) with one occur in plants with a long edible consumption history (e.g. carboxyl and one hydroxy group on which Such as Salt is Herba Santa) owing to which they are particularly suitable for based, it is found that with complete deprotonation of the use in foods. groups a doubly negatively charged anion is present, from 0193 Particularly advantageous according to the inven which in turn the number of positive charges is found (here: tion therefore is a mixture or a preparation as described above, two), which must be provided by the countercation(s). Par US 2013/025 1730 A1 Sep. 26, 2013

ticularly preferably, these counter-cations are cations selected 0205 Preferable auxiliary or carrier substances are malto from the group consisting of Na", K", NH, Ca", Mg", dextrin, starch, natural or synthetic polysaccharides and/or A1 and Zn. plant gums such as modified starches or gum Arabic, colour 0197) Particularly preferable therefore is a salt of a com ing agents, e.g. permitted food dyes, colouring plant extracts, pound of the formula (X) or a mixture (as respectively stabilizers, preservatives, antioxidants and Viscosity-modify described above) containing or consisting of ing Substances. 0198 one, two or more different salts of compounds of 0206 Particularly preferable is a mixture according to the the formula (X), preferably of compounds of the formula invention (as described above), wherein the mixture com (X) previously designated as preferable, and optionally prises a plant extract or consists thereof, preferably an extract 0199 one, two or more different salts of compounds of from Eriodictyon ssp., particularly preferably an extract from the formula (Y), preferably of compounds of the formula Eriodictyon Californicum and/or Eriodictyon angustifolium. (Y) previously designated as preferable, or A mixture preferred according to the invention or a mixture preferably to be used according to the invention (as described 0200 one or more different compounds of the formula above) according to one embodiment of the present invention (X) and/or one or more different salts of compounds of particularly preferably comprises or consists of (1.) an extract the formula (X), and optionally from Eriodictyon Californicum, (2.) an extract from Eriodic 0201 one or more different compounds of the formula tyon angustifolium or (3.) an extract from Eriodictyon Cali (Y) and/or one or more different salts of compounds of fornicum and Eriodictyon angustifolium, i.e. an extract from the formula (Y), plants or plant parts from both Eriodictyon Californicum and wherein the counter-cation(s) of one, several or all of the salts also Eriodictyon angustifolium, or (4.) a mixture of an extract of compounds of the formula (X) and/or compounds of the from Eriodictyon Californicum and an extract from Eriodic formula (Y) is or are selected from the group consisting of tyon angustifolium. Na', K", NH, Ca?", Mg, Al" and Zn". 0207 Particularly preferably, a mixture according to the 0202 Asaforesaid, one, several or all of the compounds of invention or a mixture preferably to be used according to the the formula (X) or salts of compounds of the formula (X) to be invention (as respectively described above) consists of an used according to the invention, and optionally one, several or extract from Eriodictyon ssp., particularly preferably of an all of the compounds of the formula (Y) or salts of compounds extract from Eriodictyon Californicum and/or Eriodictyon of the formula (Y) can also be used in the form of plant angustifolium. The production of a plant extract from Eriod extracts, in particular in the form of extracts from Eriodictyon ictyon Californicum and/or Eriodictyon angustifolium is ssp., in particular from Eriodictyon Californicum and/or Eri described later herein. Odictyon angustifolium, optionally after treatment with a base 0208. As described above, one aspect of the present inven for conversion of the compound(s) of the formula (X) or (Y) tion relates in particular to a preparation used for food or into a salt. enjoyment, in particular a food, luxury consumable or drink, 0203 Preferably the dried plant parts (see above) used in or a cosmetic or dermatological preparation, in particular a the context of the present invention e.g. fresh or dried roots, preparation Suitable for the treatment, protection and/or care rootbark, tubers, onions, other under- or aboveground storage of the skin, nails and/or hair and of the oral cavity (in particu organs, accessory fruit, fruit, seeds, bark, wood, pulp, bast, lar of the gingiva and the teeth), or a pharmaceutical prepa stems, stalks, leaves or flower parts, preferably the stems, ration, for the treatment of inflammatory states of the body of stalks, leaves and flower parts, preferably in comminuted warm-blooded animals. As regards the composition of such a form, are extracted with a solvent suitable for food and luxury preparation, reference is essentially made to the above expla consumables attemperatures in the range between the freez nations. ing point and the boiling point of the particular solvent or 0209. According to a preferable embodiment of the solvent mixture, then filtered and the filtrate wholly or par present invention, the proportion of the total quantity of com tially concentrated, preferably by distillation, or freeze- or pounds of the formula (X) and (optionally) compounds of the spray-drying. The crude product thus obtained can then be formula (Y) and salts thereof in the preparation lies in the still further worked up, for example back-extracted, purified range from 0.0001 to 30 wt.%, preferably in the range from via distribution, absorption, exclusion, affinity or ion chro 0.001 to 20 wt.%, particularly preferably in the range from matography, distilled, Sublimed, purified with adsorbents 0.001 to 5 wt.%, based on the total weight of the preparation. Such as activated charcoal, bentonite, diatomaceous earth, 0210 Preparations according to the invention, in particu etc., treated enzymatically (e.g. with glycosidases to increase lar preparations according to the invention used for food or yield of non-Sugar-containing molecules), with acid (e.g. enjoyment, in the context of the present invention can in under pressure), with Suitable basic solutions e.g. of hydrox particular be embodied as compositions Suitable for con ides, carbonates or hydrogen carbonates of Sodium, potas sumption (as described below). The preparations used for sium, calcium, magnesium and Zinc, with acidic ion exchang food or enjoyment in the sense of the present invention can ers or with steam, as a rule at pressures from 0.01 mbar to 100 also be used as semifinished goods for the production of bar, preferably at 1 mbar to 20 bar, treated with an auxiliary further preparations used for food or enjoyment. and carrier Substance and optionally dried (e.g. spray dried) 0211. The preparations according to the invention used for and/or taken up in a solvent suitable for food and luxury food or enjoyment and corresponding semifinished goods and consumables and/or for cosmetic and dermatological uses. preparations or compositions suitable for consumption are as 0204 Suitable solvents for the extraction are in particular a rule products which are intended to be introduced into the water, ethanol, methanol, propylene glycol, glycerine, human oral cavity, to remain there for a certain time and then acetone, dichloromethane, ethyl acetate, diethyl ether, hex either be consumed (e.g. ready-to-eat foods, see below) or ane, heptane, triacetin, plant oils or fats, Supercritical carbon removed again from the oral cavity (e.g. chewing gums). Thus dioxide and mixtures thereof. these products include all articles or Substances which are US 2013/025 1730 A1 Sep. 26, 2013 intended to be ingested by people, in the processed, partially unimportant what plant originally provided the starch for the processed or unprocessed state. In particular, compositions production of the starch hydrolyzates. Maize-based starches suitable for consumption are articles which products which and starches from tapioca, rice, wheat or potatoes in particu are added to foods during the production, processing or modi lar are suitable and readily available. Here previously fication thereof and are intended to be introduced into the described carrier Substances (e.g. silicon dioxide) can advan human oral cavity, in particular with the said food. Accord tageously function as free-flow agents. ingly, Such compositions can in turn be contained in (further) 0215. The preparations according to the invention, which ready-to-use or ready-to-eat preparations used for food or as well as one or more compounds of the formula (X) and/or enjoyment (in the context of the present text, ready-to-use or salts thereof or a suitable mixture also contain one or more ready-to-eat preparations used for food or enjoyment are in Solid carrier Substances can for example be produced by particular foods, especially ready-to-eat foods (see below)). mechanical mixing processes, wherein at the same time a In addition, such compositions can be a component of a comminution of the particles can take place, or by means of semifinished product which optionally can in turn be used for spray-drying. As described above, compositions according to the production of ready-to-use or ready-to-eat preparations the invention which contain solid carrier Substances and are used for food or enjoyment. produced by means of spray-drying are preferable; concern 0212 Preparations used for food or enjoyment in the sense ing the spray-drying, reference is made to U.S. Pat. No. 3,159, of the present invention are in particular ready-to-use or 585, U.S. Pat. No. 3,971,852, U.S. Pat. No. 4,532,145 or U.S. ready-to-eat preparations, in particular foods, especially Pat. No. 5,124,162. ready-to-eat foods, e.g. bakery products (e.g. bread, dry bis 0216 Preferable preparations containing carrier sub cuits, cakes, other pastries), confectionery (e.g. chocolates, stances (as described above) which have been produced by chocolate bar products, other products in bars, fruitgum, hard means of spray-drying preferably have a mean particle size in and soft caramels, chewing gum), alcoholic or non-alcoholic the range from 30 to 300 um and preferably a residual mois drinks (e.g. coffee, tea, wine, wine-containing drinks, beer, ture content of 5 wt.% or less. beer-containing drinks, liqueurs, spirits, brandies, fruit-con 0217. According to one embodiment of the present inven taining soft drinks, isotonic drinks, refreshment drinks, nec tion, the weight ratio of the total mass of compounds of the tars, fruit and vegetable juices, fruit or vegetable juice prepa formula (X) and optionally of the formula (Y) and salts rations), instant drinks (e.g. instant cocoa drinks, instant tea thereof in a preparation described herein containing one or drinks, instant coffee drinks), meat products (e.g. ham, fresh more (Suitable for consumption, Solid) carrier Substances (as sausage or raw sausage preparations, spiced or marinated described above) to the total mass of (suitable for consump fresh or pickled meat products), eggs or egg products (dried tion, Solid) carrier Substances preferably lies in the range from egg, egg white, egg yolk), cereal products (e.g. breakfast 1:10 to 1:100000, preferably in the range from 1:50 (prefer cereals, muesli bars, prefermented prepared rice products), ably from 1:100) to 1:20000, particularly preferably in the dairy products (e.g. milk drinks, milk-based ice cream, range from 1:100 (preferably from 1:1000) to 1:5000, based yoghurt, kefir, cream cheese, Soft cheese, hard cheese, dried on the dry mass of the preparation. milk powder, whey, butter, buttermilk, partially or fully 0218. In a preparation (as described above) containing one hydrolyzed milk protein-containing products), products from or more (suitable for consumption, Solid) carrier Substances Soya protein or other Soya bean fractions (e.g. Soya milk and (as described above), the proportion of the total quantity of products prepared therefrom, Soya lecithin-containing prepa compounds of the formula (X) and optionally of the formula rations, fermented products such as tofu or tempe or products (Y), salts thereof and (suitable for consumption, solid) carrier prepared therefrom, soya sauces), fruit preparations (e.g. pre Substances, based on the total weight of the preparation, pref serves, fruitflavoured ice cream, fruit sauces, fruit fillings), erably lies in the range from 70 to 100 wt.%, preferably in the Vegetable preparations (e.g. ketchup, sauces, dried veg range from 85 to 100 wt.%. etables, deep-frozen vegetables, prefermented vegetables, 0219. The preparations according to the invention used for Vegetables marinated in vinegar, preserved vegetables), food or enjoyment, as well as normally used animal or plant nibbles (e.g. baked or fried potato crisps or potato dough raw materials, can additionally contain water, squalane or products, bread dough products, maize- or peanut-based squalene, natural oils (e.g. olive oil, Sunflower oil, soya oil, extruded products), fat and oil-based products or emulsions peanut oil, rape oil, almond oil, palm oil, coconut oil, palm thereof (e.g. mayonnaise, remoulade, dressings, spice prepa nut oil, borage seed oil and more of the like), natural ester oils rations), other ready-to-serve meals and Soups (e.g. dried (e.g. jojoba oil), fats, waxes and other natural fatty Sub Soups, instant soups, prefermented Soups), spices, spice mix stances, carbohydrates, for example glucose, Sucrose or lac tures and in particular seasonings), which are for example tose, Sweeteners, for example aspartame, cyclamate, saccha used in the Snacks field. rin, xylitol or sorbitol, bitter substances, for example caffeine 0213 Preferable carrier substances contained in such or quinine, bitterness-suppressing Substances, for example (preferably spray dried) compositions according to the inven lactisol, flavour-intensifying Substances, for example sodium tion are silicon dioxide (silicic acid, silica gel), carbohydrates glutamate or inositol phosphate, amino acids, for example and/or carbohydrate polymers (polysaccharides), cyclodex glycine, alanine, leucine, isoleucine, Valine, proline, lysine, trins, starches, degraded starches (starch hydrolyzates), asparagine, aspartic acid, glutamine, glutamic acid, tryp chemically or physically modified starches, modified cellu tophan, phenylalanine, tyrosine, threonine, serine, cystine, loses, gum Arabic, ghatti gum, tragacanth, karaya, carrag cysteine, methionine, hydroxyproline, arginine or histidine, eenan, guar gum, carob flour, alginates, pectin, inulin or Xan peptides, proteins, enzymes, fruit acids, preferably lactic than gum. acid, malic acid or citric acid, as well as emulsifiers, which 0214 Preferable starch hydrolysates are maltodextrins can advantageously be selected from the group of the ionic, and dextrins, where here again maltodextrins with DE values nonionic, polymeric, phosphatecontaining and Zwitterionic in the range 5 to 20 are particularly preferable. Here it is emulsifiers, and in particular one or more thickeners, which US 2013/025 1730 A1 Sep. 26, 2013

can advantageously be selected from the group of the bilirubin, biliverdin, folic acid and derivatives thereof, polysaccharides or derivatives thereof, e.g. hyaluronic acid, ubiquinone and ubiquinol and derivatives thereof, vitamin C guar gum, carob flour, Xanthan gum or allulose derivatives, and derivatives thereof (e.g. ascorbyl palmitate, magnesium and natural, nature-identical or synthetic aromas and salts, for ascorbyl phosphate, ascorbyl acetate), tocopherols and example sodium chloride or potassium chloride. derivatives (e.g. alphatocopherol, Vitamin E acetate), Vitamin 0220. The cosmetic and dermatological preparations A and derivatives (e.g. vitamin A palmitate), rutinic acid and according to the invention can contain cosmetic auxiliary derivatives thereof, flavonoids (e.g. quercetin, alpha-gluco agents and/or additives such as are normally used in Such Sylrutin) and derivatives thereof, phenolic acids (e.g. gallic preparations, e.g. Sunscreens (e.g. organic or inorganic light acid, ferulic acid) and derivatives thereof (e.g. gallic acid filter Substances, preferably micropigments), preservatives, propyl ester, ethyl ester and octyl ester), furfurylidenegluci bactericides, fungicides, Virucides, cooling active Substances, tol, dibutylhydroxytoluene, butylhydroxyanisole, uric acid plant extracts, inflammation-inhibiting active Substances, and derivatives thereof, mannose and derivatives thereof, zinc wound healing accelerating Substances (e.g. chitin or chito and derivatives thereof (e.g. ZnO, ZnSO), selenium and san and derivatives thereof), film-forming Substances (e.g. derivatives thereof (e.g. Selenomethionine), stilbene and polyvinylpyrrolidones or chitosan or derivatives thereof), derivatives thereof (e.g. stilbene oxide, resveratrol) and the common antioxidants, vitamins (e.g. vitamin C and deriva derivatives of these named (active) substances suitable in the tives, tocopherols and derivatives, vitamin A and derivatives), context of the present invention. 2-hydroxycarboxylic acids (e.g. citric acid, malic acid, L-, 0223 Furthermore, a preparation according to the inven D-, or dil-lactic acid), skin lighteners (e.g. kojic acid, hydro tion (as described above), in particular a cosmetic or derma quinone or arbutin), skin colorants (e.g. walnut extracts or tological preparation according to the invention, can include dihydroxyacetone), perfumes, Substances for prevention of one or more UV-A and/or UV-B filter substances. The filter foaming, colorants, pigments which have a colorant action, substance or substances here are preferably selected from the thickeners, Surfactant Substances, emulsifiers, plasticizing, group consisting of 3-benzylidenecamphor derivatives (e.g. moistening and/or humectant Substances (e.g. glycerine or 3-(4-methylbenzylidene)-dl-camphor), aminobenzoic acid urea), fats, oils, unsaturated fatty acids or derivatives thereof derivatives (e.g. 4-(N,N-dimethylamino)benzoic acid 2-eth (e.g. linolic acid, alpha-linolenic acid, gammalinolenic acid ylhexyl ester or menthyl anthranilate), 4-methoxycinnamates or arachidonic acid and their respective natural or synthetic (e.g. 2-ethylhexyl p-methoxycinnamate or isoamyl p-meth esters), waxes or other normal components of a cosmetic or oxycinnamate), benzophenones (e.g. 2-hydroxy-4-methoxy dermatological formulation such as alcohols, polyols, poly benzophenone), singly or multiply sulphonated UV filters mers, foam stabilizers, electrolytes, organic solvents, silicone e.g. 2-phenylbenzimidazol-5-Sulphonic acid, Sulisobenzone derivatives or chelating agents (e.g. ethylendiaminetetraace or 1,4-bis(benzimidazolyl)benzene-4,4,6,6'-tetrasulphonic tic acid and derivatives). acid or 3,3'-(1,4-phenylene-dimethylidene)-bis(7,7-dim 0221) The particular quantities to be used can easily be ethyl-2-oxo-bicyclo2.2.1]heptane-1-methaneSulphonic determined by those skilled in the art by simple testing, acid) and salts thereof. Salicylates (e.g. 2-ethylhexyl salicy depending on the nature of the particular product. late or homomethyl salicylate), triazines {e.g. 2,4-bis-(4-(2- 0222 Preferably preparations according to the invention ethylhexyloxy)-2-hydroxyphenyl]-6-(4-methoxyphenyl)-1, (as described above) additionally contain one or more anti 3,5-triazine, 4,4'-(6-((1,1-dimethylethyl)aminocarbonyl oxidants, where the antioxidant or antioxidants is/are not a phenylamino)-1,3,5-triazin-2,4-diyl-diimino)bisbenzoic compound or compounds of the formula (X) or a salt thereof. acid bis-(2-ethylhexyl) ester), 2-cyanopropenoic acid In particular, as Such antioxidants, all antioxidants Suitable or derivatives (e.g. 2-ethylhexyl 2-cyano-3,3-diphenyl-2-prope usual for the respective use can be used. The antioxidant or noate, dibenzoyl derivatives (e.g. 4-tert-butyl-4'-methoxy antioxidants is or are preferably selected from the group dibenzoylmethane), polymerbound UV filters (e.g. polymers consisting of amino acids (e.g. glycine, histidine, 3,4-dihy of N-2-(or 4)-(2-oxo-3-bornylidene)methylbenzylacryla droxyphenylalanine, tyrosine, tryptophan) and derivatives mide) or pigments (e.g. titanium dioxides, Zirconium diox thereof, imidazoles (e.g. urocanic acid) and derivatives ides, iron oxides, silicon dioxides, manganese oxides, alu thereof, peptides (D.L-carnosine, D-carnosine, L-carnosine, minium oxides, cerium oxides or Zinc oxides). Such a anserine) and derivatives thereof, carotenoids, carotenes (e.g. preparation according to the invention is preferably a Sun beta-carotene, alpha-carotene, lycopene) and derivatives screen for skin and/or hair. thereof, chlorogenic acid and derivatives thereof, lipoic acid 0224. Accordingly, the present invention particularly pref and derivatives thereof, aurothioglucose, propylthiouracil erably relates to a preparation according to the invention (as and other thiols (e.g. thioredoxin, glutathione, cysteine, cys described above) additionally comprising tine, cystamine and glycosyland N-acyl derivatives thereofor 0225 (II) one or more antioxidants, wherein the antioxi alkyl esters thereof) and salts thereof, dilauryl thiodipropi dant or antioxidants is or are not a compound(s) of the onate, distearyl thiodipropionate, thiodipropionic acid and formula (x) or a salt thereofand is or are preferably selected derivatives thereof and phenolic acid amides of phenolic ben from the group consisting of beta-carotene, lycopene, chlo Zylamines (e.g. homoVanillic acid, 3,4-dihydroxyphenylace rogenic acid, 2-hydroxy fatty acids, bilirubin, folic acid, tic acid, ferulic acid, Sinapinic acid, caffeic acid, dihydroferu ubiquinone, ubiquinol, Vitamin C and derivatives thereof. lic acid, dihydrocaffeic acid, Vanillomandelic acid- or 3,4- in particular ascorbyl palmitate, magnesium ascorbyl dihydroxymandelic acid amides of 3,4-dihydroxybenzyl, 2.3, phosphate and ascorbyl acetate; tocopherols and deriva 4-trihydroxybenzyl- or 3,4,5-trihydroxybenzyl-amine), tives thereof, in particular alpha-tocopherol and vitamin E catechol oXimes or catechol oXime ethers (e.g. 3,4-dihy acetate; Vitamin A and derivatives thereof, in particular droxybenzaldoxime or 3,4-dihydroxybenzaldehyde Oethy Vitamin A palmitate; rutinic acid, quercetin, ferulic acid, loXime), also (metal) chelators (e.g. 2-hydroxyfatty acids, dibutylhydroxytoluene, butylhydroxyanisole and uric phytic acid, lactoferrin), humic acid, bile acids, bile extracts, acid, and/or US 2013/025 1730 A1 Sep. 26, 2013 16

0226 (III) one or more UV-A and/or UV-B filter sub dispenser inhalers, powder inhalers, inhalers with atomisers, stances, where one, several or all of the UV-A and/or UV-B and inhalation concentrates for the preparation of inhala filter substances is or are preferably selected from the tions), and active Substance-containing plasters or other group consisting of 3-(4-methylbenzylidene)-dl-camphor, therapeutic systems. menthyl anthranilate, 2-ethylhexyl p-methoxycinnamate, 0233. The pharmaceutical preparations according to the isoamyl p-methoxycinnamate, 2-hydroxy-4-methoxy invention can contain (further) pharmaceutical auxiliary and/ benzophenone, 2-phenylbenzimidazol-5-Sulphonic acid or additive Substances, such as are normally used in Such and salts thereof, 1,4-bis(benzimidazolyl)benzene-4,4,6, preparations, e.g. active Substances from the group of the 6'-tetrasulphonic acid and salts thereof, 2-ethylhexyl sali non-steroidal anti-inflammatories, antibiotics, systemically cylate, homomenthyl salicylate, 2.4-bis-4-(2-ethylhexy active steroids, anti-TNF-alpha antibodies or other biotech loxy)-2-hydroxyphenyl]-6-(4-methoxyphenyl)-1,3,5- nologically produced active Substances and/or pure Sub triazine, 4,4'-(6-((1,1-dimethylethyl)-amino-carbonyl stances Such as budesonide, Sulfasalazine, azathioprine/6- phenylamino)-1,3,5-triazin-2,4-diylidiimino)bisbenzoic mercaptopurine or methotrexate. And for example fillers (e.g. acid bis-(2-ethylhexyl) ester), 2-ethylhexyl 2-cyano-3,3- cellulose, calcium carbonate), free-flow and anticaking diphenyl-2-propenoate, 4-tert-butyl-4'-methoxydiben agents (e.g. talc, magnesium Stearate), coatings (e.g. polyvi Zoylmethane, titanium dioxide, silicon dioxide and Zinc nyl acetate phthalate, hydroxypropyl-methylcellulose phtha oxide. late), disintegrants (e.g. starch, crosslinked polyvinylpyrroli 0227 Particularly preferable is such a preparation accord done), plasticizers (e.g. triethyl citrate, dibutyl phthalate) ing to the invention, wherein Substances for granulation (lactose, gelatine), retardation 0228 the proportion of the total quantity of component (e.g. poly(meth)acrylic acid methyl/ethyl/2-trimethylamino (II) in the preparation, based on the total weight of the ethyl ester copolymers in dispersion, vinyl acetate/crotonic preparation, is 0.0001 to 30 wt.%, preferably 0.001 to 20 acid copolymers) and compacting (e.g. microcrystalline cel wt.%, particularly preferably 0.001 to 5 wt.%, lulose, lactose), solvent, Suspension or dispersion agents (e.g. and/or water, ethanol), emulsifiers (e.g. cetyl alcohol, lecithin), Sub 0229 the proportionorOOrt1On Ofof ththe total1 Cuant1tVquantity OTof COmponentp stances for modification of the rheological properties (silicon (Ill) in the preparation, based on the total weight of the dioxide, Sodium alginate), Substances for microbial stabiliza preparation, is 0.1 to 30 wt.%, preferably 0.5 to 10 wt. tion (e.g. benzalkonium chloride, potassium Sorbate), preser %. Vatives and antioxidants (e.g. DL-alpha-tocopherol, ascorbic 0230. The (pharmaceutical) preparations in the sense of acid). Substances for modification of the pH (lactic acid, citric the present invention used for the treatment of inflammatory acid), propellant or inert gases (e.g. fluorinated chlorohydro states of warm-blooded animals can also be used as semifin carbons, carbon dioxide), colorants (iron oxides, titanium ished goods for the production of further pharmaceutical dioxide), ointment bases (e.g. paraffins, beeswax), inter alia preparations used for the treatment of inflammatory states of as described in the technical literature (e.g. Schmidt, Christin. warm-blooded animals. Active and Auxiliary Substances for Individual and Bulk 0231. The pharmaceutical preparations according to the Formulation, and Large-scale Manufacture. 1999: Wissen invention used for the treatment of inflammatory states of schaftliche Verlagsgesellschaft mbH Stuttgart or Bauer, warm-blooded animals, and corresponding semifinished Fromming Fuhrer. Textbook of Pharmaceutical Technology. goods are as a rule products which are intended to be intro 8" Edition, 2006. Wissenschaftliche Verlagsgesellschaft duced into the body of warm-blooded animals or used on the mbH Stuttgart). body of warm-blooded animals. 0234. The particular quantities to be used can easily be 0232. The pharmaceutical preparations according to the determined by those skilled in the art by simple testing, invention used for the treatment of inflammatory states of depending on the nature of the particular product. warm-blooded animals in the sense of the present invention 0235 According to one aspect of the present invention, a are preferably ready-to-use preparations, in particular medi preparation according to the invention wherein the proportion caments and medicinal products, preferably in the following of the total quantity of compounds of the formula (X) and forms: Solid galenical forms (such as for example tablets optionally of the formula (Y) and salts thereof in the prepa (with and without coating, with and without modified ration lies in the range from 0.0001 to 30 wt.%, preferably in release), Sugar-coated tablets (with and without coating, with the range from 0.001 to 20 wt.%, and particularly preferably and without modified release), capsules (soft or hard gelatine in the range from 0.001 to 5 wt.%, based on the total weight capsules with and without modified release) granules (with of the preparation, is preferable. and without modified release), powders (with and without 0236 (Further) preferable methods for the production of a modified release), Suppositories (with and without coating, preferable mixture or preparation according to the invention with and without modified release) lozenges and chewing (as described above) are described below. gums), and liquid forms (such as for example solutions, Sus 0237 Such a method preferably comprises the steps pensions, emulsions, syrups (colloquially cough syrup), 0238 (a) extraction of plant material (as described above), mouthwashes, gargle solutions, throat sprays or nasal sprays, preferably as described above as preferable, and nasal drops, nasal rinse Solutions, nasal powders, nasal oint 0239 (b) concentration of extracted compounds of the ments or ear drops, ear sprays, ear rinse solutions, ear pow formula (X) and optionally additionally of the formula (Y) ders and aural tampons), and semisolid forms (such as for and/or salts thereof (as described above) by partial or com example hydrophobic ointments including for example: plete removal of other extracted compounds and optionally hydrocarbon gels, lipogels, silicone gels, oleogels and water removal of extractants and/or solvents, preferably so that absorbing ointments including for example absorption bases, the proportion of the total quantity of compounds of the hydrophilic ointments, hydrophilic gels (hydrogels) or formula (X) and optionally (Y) and salts thereof in the pastes, and inhalants (such as for example compressed gas mixture obtained, based on the total weight of the mixture, US 2013/025 1730 A1 Sep. 26, 2013

is 0.0001, preferably 15 to 100 wt.%, preferably 25 to 90 0253) The mixtures (e) and (h) and the mixtures present wt.% (preferably 100 wt.%), and particularly preferably after the steps f) and g), in particular mixture (h), can each be 45 to 85 wt.% (preferably 100 wt.%). mixtures according to the invention (as described above). 0240 For example, a mixture or preparation according to 0254 Evaporative or pervaporative methods can for the invention (as described above) can also be produced by a example be distillation, Sublimation, Steam distillation, method according to the invention (as described above), freeze drying, pervaporative membrane methods or spray wherein the method is carried out following the method drying, and particular appropriate auxiliary and/or carrier described in the publication in WO2004041804 (for the Substances can be added thereto. obtention of a crude extract from Eriodictyon Californicum 0255 According to an alternative embodiment of a and/or Eriodictyon angustifolium). method according to the invention for the production of a 0241 The steps of such a method according to the inven mixture as described above, a methanolic crude extract is tion (partly based on the method according to obtained from Eriodictyon ssp., preferably Eriodictyon Cali WO2004041804) are briefly summarized below: fornicum and/or Eriodictyon angustifolium, which contains 0242 (a) Plant material from Eriodictyon Californicum extracted compounds of the formula (X) and optionally of the and/or Eriodictyon angustifolium is singly or multiply formula (Y) and other extracted compounds (in particular extracted with a non-water-miscible extractant (optionally roSmarinic acid). Herein also, the extracted compounds of the with heating up to the relevant boiling point). formula (X) and optionally of the formula (Y) and/or salts of these extracted compounds in the mixture are concentrated by 0243 (b) The crude extract thus obtained (containing partial or complete removal of other extracted compounds compounds of the formula X and/or of the formulaY to be and optionally removal of extractants and/or solvents (each used according to the invention and other extracted com time preferably analogously to the previously described pounds such as for example roSmarinic acid) is separated method design), so that the proportion of the total quantity of from the plant material. compounds of the formula (X) and optionally of the formula 0244 (c) The crude extract (containing compounds of the (Y) and salts thereof in the mixture, based on the dry mass of formula X and/or of the formula Y to be used according to the mixture, for example preferably lies in the range from 40 the invention and other extracted compounds Such as for to 100 wt.%, particularly preferably 45 to 85 wt.%. example rosmarinic acid) is preferably concentrated and (0256 Such concentration is preferably attained by FCPC interim Stocked. (Fast Centrifugal Partition Chromatography, Guido F. Pauli, 0245 (d) Precipitated solids (waxes) are optionally Samuel M. Pro, J. Brent Friesen Countercurrent Separation of removed. Natural Products.J. Nat. Prod. 2008, 71, 1489-1508) and/or 0246 (e) The (optionally dewaxed) crude extract (contain HTLC (High Temperature Liquid Chromatography: ing compounds of the formula (X) and optionally of the WO2006111476) and/or preparative HPLC (High Pressure formula (Y) to be used according to the invention and other Liquid Chromatography). extracted compounds such as for example roSmarinic acid) 0257 According to a preferable embodiment of the is optionally treated with activated charcoal and separated present invention, the extracts or mixtures described herein from the solid. are incorporated in the form of emulsions into liposomes, for 0247 Through the following further steps, the compounds example starting from phosphatidylcholine, into micro of the formula (X) and optionally of the formula (Y) to be spheres, into nanospheres or also into capsules, granules or used according to the invention can be further concentrated in extrudates, for example of starch, starch derivates, cellulose the organic phase: or cellulose derivates (for example hydroxypropylcellulose), 0248 (f) (Preferably complete) removal of the organic other polysaccharides (for example alginates), natural fats, Solvent of the organic phase by evaporative or permeative natural waxes (for example beeswax, carnauba wax) or of methods. proteins, for example gelatine. 0249 (g) Taking up of the residue (comprising compounds 0258. In connection with the present invention, a prophy of the formula (X) and optionally of the formula (Y) to be lactic and/or therapeutic method as described above, with the used according to the invention) in methanol. following step, is also described: 0250 (h) Removal of the methanol-insoluble components 0259 Contacting of (human or animal) tissue and/or of the of the mixture (comprising compounds of the formula (X) (human or animal) cells with an inflammation-inhibiting and optionally of the formula (Y) to be used according to effective quantity of a compound of the formula (X), a salt of the invention and other extracted compounds) by filtration. a compound of the formula (X), an above-described mixture, 0251. In the mixture present according to this method after in particular of a mixture which additionally comprises a step e), the proportion of the total quantity of compounds of compound of the formula (Y) and/or a salt thereof, as respec the formula (X) and optionally of the formula (Y) and salts tively described above, or of a preparation as described above. thereof, based on the dry mass of the mixture (), according to 0260 The contacting of the tissue or the cells with one or a preferable embodiment of the present invention lies in the more compounds of the formula (X) and optionally addition range from 1 to 35 wt.%, preferably in the range from 20 to ally one or more compounds of the formula (Y) and/or salts 35 wt.%. thereof or a mixture or preparation according to the invention 0252. In the mixture (h) present according to this method (as respectively described above) here—depending on the according to the invention after Steph), the proportion of the tissue to be treated or the cells to be treated—can also be total quantity of compounds of the formula (X) and optionally effected by external (e.g. topical) or internal use (e.g. oral of the formula (Y) and salts thereof, based on the dry mass of application). the mixture (h), preferably lies in the range from 40 to 100 wt. 0261 The following examples serve to clarify the inven %, preferably in the range from 45 to 85 wt.%. tion, without thereby restricting this. US 2013/025 1730 A1 Sep. 26, 2013

EXAMPLES TABLE 2-continued

Preparation Examples FCPC conditions

Example 1 Fractionation 40 fractions of 8 ml (ascending mode) 30 fractions of 10 ml (descending mode) Production of a Methanolic Extract from Eriodictyon angustifolium 0262 Boiling water was poured over 500 g of dried leaves of Eriodictyon angustifolium and stirred for one hour in order TABLE 3a to swell the plant material and prepare it for the further extrac Analytical data tion. The plant material was filtered off, dried and extracted twice with 2.01 methanol each time at room temperature for Erionic acid F (6) Erionic acid C (3) one hour with stirring. The methanolic extract was filtered off, 200 MHZ, CH3OD 200 MHZ, CH3OD dried under vacuum and stored overnight in the high vacuum PoS. 8, mult. 6 (J in Hz) 8, mult. 8 (J in Hz) drying oven to remove residual solvent. The extraction 1 123.2 n.d. yielded 84.53 g of dark green extract. 2 130.8 7.63, d (2.1) 131.1 6.92, s 3 129.4 1303 Example 2 4 158.4 158.4 5 129.4 125.6 6 13 O.S 7.71, d (2.1) 130.8° 6.92, s Isolation of the Individual Compounds from 7 170.8 171.1 Eriodictyon angustifolium by Means of FCPC 8 29.0 2.61, m 29.2 2.59, m 9 33.8 1.95, m 33.9 1.95, m 0263. The methanolic extract of E. angustifolium accord 1.61, m 1.61, m ing to Example 1 was separated and fractionated by means of 10 46.2 2.65 m 46.5 2.66, m FCPC using a two-phase solvent system (heptane/ethyl 9 33.8 1.95, m 33.9 1.95, m 1.61, m 1.61, m acetate/methanol/water 5:4:4:5). As well as flavones 11 216.1 217.4 described in the literature, four compounds of the formula (X) 12 44.5 3.18, m. 42.2 3.19, m could be isolated. Structure elucidation was effected by 13 117.2 5.23, dd (7.1, 7.1) 117.5 5.24, m means of one- and two-dimensional NMR experiments. The 14 136.7 136.8 retention times are shown in Table 1, the FCPC conditions in 15 25.9 1.77, st 25.9 1.72, s 16 16.9 1.12, d (7.0) 16.9 1.12, d (7.0) Table 2 and analytical data in Tables 3a and 3b. 17 17.9° 1.72, s. 18.3 1.61, S 18 29.4 3.33, d (7.3) 29.2 3.40, d (74) TABLE 1. 19 123.0 5.32, dd (7.3, 7.3) 1242 5.61, dd (7.4, 7.4) 2O 1342 137.8 Retention time for various Erionic acids 21 26.O 1.72, s 69.1 3.99, s 22 18.1° 1.60, s 13.9 1.76, s Molecular weight Retention time Compound g/mol min interchangeable signals Erionic acid F (6) 358 17.0-19.0 (ascending) Erionic acid C (3) 374 64.0-69.0 (ascending) TABLE 3b Erionic acid A. (1) 390 52.0-54.0 (descending) Erionic acid B (2) 390 55.0-56.0 (descending) Analytical data Erionic acid A. (1) Erionic acid B (2) 400 MHz, DMSO 600 MHZ, CH3OD TABLE 2 6, mult. 8 (J in Hz) 8, mult. 6 (J in Hz) FCPC conditions 1 127.7g 130.3 FCPC bench scale FCPC model, version A 2 128.7 7.52, s 130.4 7.57, d (2.1) (Kromaton Technologies, Angers, France) 3 128.3 129.6 Rotor 200 ml (semi-preparative) 4 156.5 155.0° Injector Kronlab High Speed Valve (Kronlab 5 121.0 131.4 Chromatography Technology, Dinslaken) 6 128.9° 7.52, s 130.4 7.56, d (2.1) Injection loop Oml 7 169.1 1702 Pumps Knauer HPLC pump 64 (Knauer Berlin) 8 27.4 2.55, m 28.9 2.58, m Pulse damper Type 55073 (BESTA-Technik, Wilhelmsfeld) 9 32.6 1.83, m 34.6 1.96, m Detector ELSD SEDEX 75 Light scattering detector 1.51, m. 1.61, m (S.E.D.E.R.E., Alfortville, Cedex, France) 10 42.7 2.85, ddd 44.4 2.86, ddd Fraction collector Labocol Vario 2000 (Labomatic, Weilam Rhein) (6.8, 6.8, 6.8) (6.8, 6.8, 6.9) Software PrepCon (SCPA. GmbH, Weye-Leeste): 11 2O3.4 2O7.O Version 5.03.009, SCPA. GmbH 2003 12 123.8 6.27, d (15.8) 125.6 6.29, d (15.8) Solvent system upper phase: heptane ethyl acetate (5.4) 13 154.3 6.83, d (15.8) 1549° 6.83, d (15.8) ower phase: methanol/water (4/5) 14 69.1 71.2 Ascending mode methanol/water as stationary phase 15 29.0 1.22, s. 29.3 1.30, s. Descending mode heptane ethyl acetate as stationary phase 16 16.2 1.07, d (6.9) 16.8 1.13, d (6.9) Stock solution 60 mg/10 ml stationary/mobile Phase (1:1) 17 29.0 1.23,s 29.3 1.29, s Flow rate 8 ml/min (ascending mode) 18 27.6 3.33, d (7.3) 32.4 3.02, dd (5.4, 16.5) 0 ml/min (descending mode) 2.74, dd (7.8, 16.5) US 2013/025 1730 A1 Sep. 26, 2013 19

TABLE 3b-continued TABLE 5-continued Analytical data HTLC conditions Erionic acid A. (1) Erionic acid B (2) 50 min: O% A 100% C 400 MHz, DMSO 600 MHZ, CH3OD 60 min: O% A 100% C Detection ELSD (3.5 bar N2, 45° C., gain 6); DAD 210 nm, 6, mult. 8 (J in Hz) 8, mult. 6 (J in Hz) 250 nm, 280 nm, 320 mm 19 120.8 5.50, dd (7.3, 7.3) 70.5 3.75, dd (7.8, 5.4) 2O 136.2 78.4 0265. The following analytical data for erionic acid C (3) 21 66.1 3.83, s 24.3° 1.36, s and erionic acid F (6) correspond to those stated in Example 22 13.1 1.65, s 21.0° 1.25, s 2. interchangeable signals TABLE 6 Example 3 Analytical data Erionic acid D (4) Erionic acid E (5) Isolation of the Individual Compounds from 400 MHZ, CH3OD 200 MHZ, CH3OD Eriodictyon angustifolium by Means of High Temperature Liquid Chromatography (HTLC) PoS. 8, mult. 8 (J in Hz) 8, mult. 6 (J in Hz) 1 130.6 123.3 0264. The methanolic extract of E. angustifolium accord 2 130.6° 7.60, d (2.2) 131.0° 7.60, d (2.2) ing to Example 1 was separated and fractionated by means of 3 130.6 1303 HTLC using a polymer-based semi-preparative column with 4 156.2 158.1 5 120.9.120.8 128.9 water-ethanol gradients under isothermal conditions (120° 6 131.3 7.61, d (2.2) 130.8° 7.63, d (2.2) C.). In addition to flavones described in the literature, four 7 1710 1715 substances could be isolated. The results are shown in Table 4, 8 28.9/28.8 2.56, m 29.3 2.62, m the HTLC conditions in Table 5 and analytical data in Tables 9 34.0/340 1.94, m 34.4 1.97, m 6. 1.60, m 1.63, m 10 46.3/46.3 2.63, m 44.5 2.89, ddd (6.9, 6.9, 6.9) TABLE 4 11 215.6.21S.S 2O7.1 12 41.9 3.17, m. 125.8 6.34, d (15.9) Retention time for various Erionic acids 13 117.3 5.23, m 155.5 6.88, d (15.9) 14 136.6 71.2 Molecular weight Retention time 15 25.9 1.72, s 29.3 1.31, s Compound g/mol min 16 16.7 1.11, d (6.9) 17.2 1.15, d (7.0) 17 18.3 1.60, s 29.3 1.31, s Erionic acid C (3) 374 14.5-15.3 18 32.2 3.05/3.06, ddidd 29.7 3.31 (masked by Erionic acid D (4) 374 154-16.5 (16.7, 5.2) solvents), Erionic acid E (5) 374 17.O-17.7 2.76, dd (16.6, 7.2) Erionic acid F (6) 358 220-23.O 19 70.0/70.0 3.78, m. 123.4 5.33, dd (7.4, 7.4) 2O 79.1 79.1 134.5 21 26.1/26.0 1.37 (1.36°. 26.2 1.77, s 22 21.6/21.3 1.30/1.29 18.0 1.71, s TABLE 5 interchangeable signals HTLC conditions Pumps 2 SunChrom HPLC pumps SunFlow 100 (SunChrom, Example 4 Friedrichsdorf, Germany) Injector 00 ul loop: Midas, Spark, AJ Emmen, The Netherlands Production of a Extract of Erionic Acid from E. HPLC owen Polaratherm Series 9000 (Selerity Technologies angustifolium by Means of Gel Permeation nc., Salt Lake City, USA) Chromatography Detectors Light scattering detector (ELSD) Sedex 85 LT-ELSD (Sedere, Alfortville, Cedex, France); Diode array 0266. From 0.5g of the methanolic extract of E. angusti detector (DAD) SunChrom SpectraFlow, wavelengths folium according to Example 1, the flavanones were removed 200-400 nm (SunChrom, Friedrichsdorf, Germany) Column Hamilton PRP-1 reversed phase; 250 x 10 mm with a flow rate of 2.5 ml/min over a Sephadex-LH 20 col semi-preparative; 10 lm particle size umn. After evaporation an extract (“FF) rich in flavonoids (Hamilton, Bonaduz, Switzerland) was obtained. The remaining part was dried under vacuum Flow rate 3 ml/min and stored overnight in the high vacuum drying oven to Fraction collector Labocol Vario 2000 (Labomatic, Weilam Rhein) Software PrepCon (SCPA. GmbH, Weye-Leeste); remove residual solvent. The flavonoid free dry extract thus Version 5.03.009, SCPA. GmbH 2003 obtained had a content of 46% of benzoic acid derivatives to Stock solution 400 mg/ml E. angustifolium extract (Y) in be used according to the invention. ethanol/water (1:1) Injection volume 00 ul Column Hamilton PRP-1 250 x 10 mm Gel Permeation Chromatography Conditions Temperature 20°C. isothermal Eluent A: water C: ethanol 0267 Stock solution: 0.5 g/20 ml methanol Gradient O min: 100% A O% C 0268 Column: Kronlab 3.5x60 cm 30 min: 50%. A 50% C 0269 Column material: Sephadex LH-20 0270 Solvent: Methanol US 2013/025 1730 A1 Sep. 26, 2013 20

0271 Flow rate: 2.5 ml/min TABLE 8-continued (0272. Detection (UV): 210 mm 0273 FIG. 1 shows typical LC-MS chromatograms (a) of HTLC conditions the extract rich in erionic acid thus obtained and (b) of the Injection volume 100 ul extract rich in flavonoids respectively. Column Hamilton PRP-1 250 x 10 mm Temperature 120° C. isothermal Example 5 Eluent A: water C: ethanol Gradient O min: 100% A O% C Production of a Methanolic Extract from Eriodictyon 30 min: 50%. A 50% C Californicum 50 min: O% A 100% C 60 min: O% A 100% C 0274 Boiling water was poured over 150 g of dried leaves Detection ELSD (3.5 bar N2, 45° C., gain 6); DAD 210 nm, of Eriodictyon Californicum and stirred for one hour in order 250 nm, 280 nm, 320 mm to swell the plant material and prepare it for the further extrac tion. The plant material was filtered off, dried and extracted twice with 1.51 of methanol each time at room temperature TABLE 9a for one hour with stirring. The extract was filtered, dried under vacuum and stored overnight in the high vacuum drying Analytical data oven to remove residual solvent. The extraction yielded 32.65 Eriolic acid A (7) Eriolic acid B (8) g of dark green extract. 400 MHZ, CH3OD 200 MHZ, CHOD Example 6 PoS. 6, mult. 8 (J in Hz) 8, mult. 6 (J in Hz) 1 29.6 23.1 Isolation Of the Individual Compounds from 2 31.0 7.72, s 30.3 7.64, d (2.2) Eriodictyon Californicum by Means of HTLC 3 35.7 28.8 4 61.4 58.2 0275. The methanolic extract of E. Californicum accord 5 35.7 29.2 ing to Example 5 was separated and fractionated by means of 6 30.9 7.72, s 30.3 7.63, d (2.2) HTLC using a polymer-based semi-preparative column with 7 70.6 70.9 8 28.8° 3.43, d (7.1) 29.0 3.38, d (74) water-ethanol gradients under isothermal conditions (120° 9 25.5 5.50, dd (7.2, 7.2) 24.9 5.50, dd (7.4, 7.4) C.). In addition to flavones known from the literature, four 10 39.6 39.6 compounds of the formula (X) could be isolated. The results 11 78.6 3.98, dd (7.0, 7.0) 78.7 3.99, dd (7.0, 7.0) are shown in Table 7, the HTLC conditions in Table 8 and 12 34.8 2.26, dd (7.0, 7.0) 34.8 2.26, dd (7.0, 7.0) 13 21.7 5.07, dd (7.0, 7.0) 21.7 5.08, dd (7.0, 7.0) analytical data in Tables 9a and 9b. 14 34.O 34.0 15 26.0 1.63, s 26.0 1.64, s TABLE 7 16 11.8 1.74, s 11.6 1.72, s 17 18.0 1.60, s 17.9° 1.59, s Retention time for various Eriolic acids 18 28.9° 3.45, d (7.1) 29.4 3.33, d (7.1) 19 24.5 5.57, dd (7.3, 7.3) 23.0 5.32, dd (7.3, 7.3) Molecular weight Retention time 2O 37.5 34.1 Compound g/mol min 21 68.7 3.98, s 26.0 1.76, s 22 13.9 1.78, s 18.0° 1.72, s Eriolic acid A (7) 388 15.0-16.5 23 61.6 Eriolic acid B (8) 358 21.0-22.9 Eriolic acid C (9) 374 13.5-14.8 ab interchangeable signals Eriolic acid D (10) 372 20.0-21.O TABLE 9b TABLE 8 Analytical data HTLC conditions Eriolic acid C (9) Eriolic acid D (10) 200 MHZ, CH3OD 200 MHZ, CH OD Pumps 2 SunChrom HPLC pumps SunFlow 100 (SunChrom, Friedrichsdorf, Germany) PoS. 6, mult. 8 (J in Hz) 6 mult. 8 (J in Hz) Injector 100 ill loop: Midas, Spark, AJ Emmen, The Netherlands 1 123.4 128.4 HPLC owen Polaratherm Series 9000 (Selerity Technologies 2 130.4 7.65, s 130.8 7.71, d (2.2) Inc., Salt Lake City, USA) 3 128.8 135.5 Detectors Light scattering detector (ELSD) Sedex 85 LT-ELSD 4 158.1 1613 (Sedere, Alfortville, Cedex, France); Diode array 5 128.8 136.1 detector (DAD) SunChrom SpectraFlow, wavelengths 6 130.4 7.65, s 130.8 7.70, d (2.2) 200-400 nm (SunChrom, Friedrichsdorf, Germany) 7 171.1 170.7 Column Hamilton PRP-1 reversed phase; 250 x 10 mm 8 29.1° 3.38, d (7.2) 28.8 3.43, d (7.3) semi-preparative; 10 lm particle size 9 124.7 5.55, dd (7.4, 7.4) 125.5 5.50, dd (7.2, 7.2) (Hamilton, Bonaduz, Switzerland) 10 139.6 139.5 Flow rate 3 ml/min 11 78.6 3.99, dd (7.1, 7.1) 78.6 3.98, dd (7.0, 7.0) Fraction collector Labocol Vario 2000 (Labomatic, Weilam Rhein) 12 34.8 2.26, dd (7.1, 7.1) 34.8 2.26, dd (7.0, 7.0) Software PrepCon (SCPA. GmbH, Weye-Leeste); 13 121.6 5.09, dd (7.1, 7.1) 121.6 5.06, dd (7.0, 7.0) Version 5.03.009, SCPA. GmbH 2003 14 1340 133.9 Stock solution 300 mg/ml E. Californicum extract (Y) in 15 26.0 1.64, s 26.0° 1.63, s ethanol/water (1:1) 16 11.6 1.72, s 11.7 1.74, s US 2013/025 1730 A1 Sep. 26, 2013

TABLE 9b-continued residual solvent. The flavanoidfree dry extract thus obtained had a content of the benzoic acid derivatives to be used Analytical data according to the invention of 62%. Eriolic acid C (9) Eriolic acid D (10) 200 MHZ, CH3OD 200 MHZ, CH3OD Formulation Examples PoS. 6, mult. 8 (J in Hz) 6 mult. 8 (J in Hz) 0285. The following tables show formulation examples 17 18.0 1.60, s 18.0° 1.59, s 18 28.9° 3.40, d (74) 29.2 3.38, d (7.3) comprising the products of the present invention. 19 124.1 5.61, dd (7.4, 7.4) 123.7 5.28, dd (7.3, 7.3) 2O 137.4 133.9 TABLE I 21 68.8 3.99, s 25.9° 1.75, s 22 13.8 1.76, s 17.9° 1.74, s Low-fat yoghurt, Sweetened (Amounts in 90 b.w. 23 61.5 3.76, s Ingredient A. B C interchangeable signals Sucrose 10 8 6 Tagatose — 0.5 Example 7 Fructose - O.OS Hesperetin - 0.1 O.OOS Production of a Concentrated Extract from Phloretin - O.OOS Strawberry flavour — 0.25 — Eriodictyon Californicum by Means of Precipitation Peach flavour 0.3 – 0.4 Herba Santa extract (E. angustifolium) 0.4 0.4 0276 5.0 g of an extract of E. Californicum prepared as per Example 1 (10% in ethanol) analogously to Example 5 were dissolved in 100 ml ethyl Concentrated Herba Santa extract (E. angustifolium) O.1 acetate. By addition of 10 ml of 3% sodium hydroxide solu as per EX. 4 (10% in ethanol) tion with stirring, the homoeriodictyol contained was precipi Yoghurt, 0.1% fat Ad 100 tated out. The remaining solution was dried over sodium Sulphate and concentrated. The Sterubin also contained in the extract was precipitated out by Storage of the extract in the refrigerator for 12 hours. After filtration, the filtrate was dried TABLE II under vacuum and stored overnight in the high vacuum drying oven to remove residual solvent. The flavonoid-depleted dry Low fat yoghurt, reduced sugar (amounts in 90 b.w. extract thus obtained contained benzoic acid derivatives to be Ingredient A. B C D used according to the invention in a proportion of 50%. Tagatose O482 0.482 0.482 Sucralose O.OO3 O.OO3 O.OO3 Example 8 Aspartame O.OO O.OO O.OO Acesulfam K O.O1 O.O1 O.O1 Production of a Concentrated Extract from E. Rebaudioside A O.OO Rubus stia vissini is extract O.OO Californicum by Means of Gel Permeation Hesperetin O.O1 O.OO O.OO Chromatography Phloretin O.OO O.OO Strawberry flavour O.2 O.2 0277 From 0.5g of the methanolic extract of E. Califor Raspberry flavour O.3 0.4 nicum according to Example 5, the flavanoids were removed Herba Santa extract (E. californicum) O.3 0.4 with a flow rate of 2.5 ml/min over a Sephadex-LH 20 col as per EX. 5 (10% in ethanol) Concentrated Herba Santa O.1% 0.1% umn, and the remaining extract dried under vacuum and extract (E. californicum) stored overnight in the high vacuum drying oven to remove as per EX. 8 (10% in ethanol) residual solvent. The purified dry extract thus obtained had a Yoghurt, 0.1% fat Ad 100 content of the benzoic acid derivates to be used according to the invention of 75%. (0278 Stock solution: 0.5 g/20 ml methanol 0279 Column: Kronlab 3.5x60 cm TABLE III 0280 Column material: Sephadex LH-20 Low fat yoghurt drink, Sweetened (amounts in 90 b.w. 0281 Solvent: Methanol 0282 Flow rate: 2.5 ml/min Ingredient A. B C (0283 Detection (UV): 210 mm Sucrose 7 4 5 Tagatose O.S Fructose O.OS Example 9 Hesperetin O.1 O.OOS Phloretin O.OOS Production of a Concentrated Extract by Means of Strawberry flavour O.15 Gel Permeation Chromatography Red fruit flavour O.2 O.25 Colouring food: fruit juice 5 5 5 0284. An extract prepared according to WO2004041804 Herba Santa extract O3S O.2 which had already been depleted of homoeriodictyol and (E. anglisiifolium) as per Example 1 (10% in ethanol) sterubin by the method described therein was fractionated Concentrated Herba Santa O.15 over a Sephadex LH-20 column analogously to Example 4 to extract (E. anglisiifolium) remove the residual flavonoids, dried under vacuum and as per EX. 4 (10% in ethanol) stored overnight in the high vacuum drying oven to remove US 2013/025 1730 A1 Sep. 26, 2013 22

TABLE III-continued TABLE VII Low fat yoghurt drink, Sweetened (amounts in 90 b.w. Fruity muesli bars (amounts in % b.w.) Ingredient A. B C Yoghurt, 0.1% fat 60 60 60 Ingredients Water Ad 100 Saccharose 15.992 Glucose syrup 14.0 TABLE IV SorbitOP3OO S.O Sugar-free hard caramels (amounts in 90 b.W. Plant fat S.O Water 3.0 Ingredient A. B Rolled oats 7.3 Palatinit, type M Ad 100 Oat flakes 7.0 Water 24.82 24.82 Cornflakes 4.5 Peppermint flavour O.15 O.OS Hesperetin O.10 Rice crispies 1S.O Trans-pellitorin (10% in ethanol) O.O1 Currants Herba Santa extract O.1 (E. anglisiifolium) as per Dried blueberries Ex. 1 (10% in ethanol) Citric acid powder Concentrated Herba Santa O.OS extract (E. anglisiifolium) Concentrated Herba Santa extract as per EX. 4 as per EX. 4 (10% in ethanol)

0286 Palatinit was mixed with water and the mixture was TABLE VIII melted at 165° C. then cooled to 115° C. Flavouring and extract produced according to the invention, and trans-pelli Chewing gun for bad breath (amounts in 90 b.w. torin in case A and hesperetin in case B, were added, and after Ingredients A. D thorough mixing poured into moulds, and after Solidification Chewing gum base 21.00 21.00 21.00 21.00 were removed from the foil and then individually packed. Glucose syrup 16.8O 16.8O 16...SO 16...SO Glycerine OSO O.SO OSO OSO TABLEV Sugar powder 6O.OO 60.40 6O4(O Spearmint flavour 1...SO 1...SO 1...SO Black, green or herb tea (amounts in 90 b.W. Herba Santa extract (E. angustifolium) as per EX. 1 10% in ethanol Ingredient A. B C D E Herba Santa extract (E. californicum) as per EX. 5 10% in ethanol Black tea (Ceylon) leaves 99.4 — Concentrated extract from E. anguistifolium O.1 Green tea (China), leaves – 99.2 — as per EX. 4 - 10% in ethanol Mate tea (Peru), leaves – 99.5 — Concentrated extract from E. Californicum O.1 Rooibos tea (South Africa), leaves – 99.6 — as per EX. 7 - 10% in ethanol Honeybush tea (South Africa), leaves - 99.6 Herba Santa extract O.3 0.8 — 0.4 O.2 (E. anglisiifolium) as per EX. 1 Herba Santa extract 0.3 — 0.5 — O.2 TABLE IX (E. californicum) as per EX. 5 Sugar-free chewing gun for bad breath (amounts in 90 b.w. Ingredients A. D TABLE VI Chewing gum base 3O.OO 30.00 3O.OO 3O.OO Soya drink Sorbitol, powder 38.25 38.25 38.40 38.40 Palatinit 9.SO 9.SO 9.SO 9.SO ngredient A. B C Xylitol 2.OO 2.OO 2.00 2.OO Mannitol 3.00 3.00 3.00 3.00 Sucrose 5 5 3.5 Aspartame O.10 O.10 O.10 O.10 Tagatose O.S Acesulfam K O.10 O.10 O.10 O.10 Fructose O.OS Emulgum emulsifier O.30 O.30 O.30 O.30 Hesperetin O.OOS Sorbitol 70%, in water 14.00 14.00 14.00 14.00 Phloretin O.OOS Glycerine 1.OO 1.OO 1.00 1.OO Chocolate flavour O.15 Cinnamon menthol flavour 1...SO 1...SO 1...SO 1...SO Vanilla flavour O.1 O.1 Herba Santa extract (E. angustifolium) O.25 Herba Santa extract O.08 O.1 as per EX. 1 - 10% in ethanol (E. anglisiifolium) as per Herba Santa extract (E. californicum) Example 1 (10% in ethanol) as per EX. 5 - 10% in ethanol Concentrated Herba Santa O.OS Concentrated extract from E. anguistifolium O.1 extract (E. californicum) as per EX. 4 - 10% in ethanol as per Ex. 8 (10% in ethanol) Concentrated extract from E. Californicum UnSweetened soya milk base Ad 100 as per EX. 7 - 10% in ethanol US 2013/025 1730 A1 Sep. 26, 2013 23

TABLE X TABLE XIII-continued Ready-to-use mouthwash solution with fluoride Toothpaste (amounts in 90 b.w. for bad breath (amounts in % b.w. Ingredient INCI A. Ingredients A. B C Solbrol M (Nasalt) Solbrol M (Sodium salt) O.15 Ethanol 7.OO 7.OO 7.OO (methylparaben) Glycerine 12.OO 12.OO 12.OO Trisodium phosphate Trisodium phosphate O.10 Na fluoride O.OS O.OS O.OS Saccharin Saccharin O.2O Pluronic F-127 (R) (BASF, 140 140 140 Sodium Sodium monofluorophosphate 1.14 Surface-active Substance) monofluorophosphate Naphosphate buffer pH 7.0 1.10 1.10 1.10 PEG 1500 PEG 1500 S.OO Sorbic acid O.2O O.20 O2O Sident 9 (abrasive silica gel) Sident 9 (abrasive silica) 1O.OO Nasaccharinate O.10 O.10 O.10 Sident 22 S (thickener) Sident 22 S (thickening silica) 8.OO Cinnamon menthol flavour O.15 O.15 0.15 Sodium Sodium carboxymethylcellulose 1.10 Herba Santa extract (E. angustifolium) O.3 carboxymethylcellulose as per EX. 1 10% in ethanol Titanium (IV) oxide Titanium (IV) oxide OSO Herba Santa extract (E. californicum) O.3 Sodium laurylsulphate (SLS) Sodium laurylsulphate (SLS) 1...SO as per EX. 5 10% in ethanol Aroma (PF1, PF2, PF3 or PF4) Flavour 1.OO Concentrated extract from E. anglisiifolium O.08 Concentrated Herba Santa extract (E. californicum) O4O as per EX. 410% in ethanol as per EX. 7 (10% in ethanol) Colorant O.O1 O.O1 O.O1 Dist. water Ad 100

TABLE XIV TABLE XI Anti-placaue toothpaste (amounts in 96 b.w. Mouthwash solution (concentrate) for Ingredient A. B bad breath (amounts in 96 b.w. Carrageenan O.90 O.90 Ingredients A. B C Glycerol 1S.OO 1S.OO Sorbitol 70%, in water 2S.OO 2S.OO Ethanol, 95% 80.00 8O.OO 8O.OO PEG 1 OOO 3.00 3.00 Na cyclamate O.15 O.15 O.15 Na fluoride O.24 O.24 Eucalyptus, wintergreen flavour 3.SO 3.SO 3.SO Tetrapotassium diphosphate 4...SO 4...SO Colorant O.O1 O.O1 O.O1 Tetrasodium diphosphate 1...SO 1...SO Herba Santa extract O.SO Nasaccharinate O4O O40 (E. anglisiifolium) as per Ex. 1 Precipit. Silica gel 2O.OO 2O.OO Concentrated extract from O.1 Titanium dioxide 1.OO 1.OO E. anglisiifolium as per EX. 4 Triclosan O.30 O.30 Concentrated extract from O.1 PHB methyl ester O.10 O.10 E. californicum as per Ex. 7 Spearmint flavour (containing 1.OO 1.20 Demin. water Ad 100 60 wt.% L-carvone and 25 wt.% L-menthol) Concentrated Herba Santa O.30 extract (E. californicum) as TABLE XII per Ex. 7 (10% in ethanol) Herba Santa extract O.SO Mouthwash solution with fluoride for (E. californicum) as bad breath (amounts in 96 b.w. per Ex. 1 (10% in ethanol) Sodium dodecylsulphate 1.30 1.30 Ingredient INCI A. Demin. water Ad 100 Ethyl alcohol Ethyl alcohol 10.00 Cremophor CO 40 Cremophor CO 40 (PEG 1.00 40 hydrogenated castor oil) TABLE XV Benzoic acid Benzoic acid O.12 Aroma (PF1, PF2, PF3 or PF4) Flavour O.25 Tooth cream for pain-sensitive teeth (amounts in 90 b.w. Demin. water Water (deionized) 83.28 Sorbitol 70% Sorbitol 70% S.OO Ingredient A. B Sodium saccharin Sodium saccharin 450 O.O7 Sodium fluoride Sodium fluoride O.18 Na carboxymethylcellulose O.70 O.70 Herba Santa extract (E. angustifolium) O.10 Xanthan gum O.SO OSO as per EX. 1 (10% in ethanol) Glycerol 1S.OO 1S.OO Sorbitol 70%, in water 12.00 12.00 Potassium nitrate S.OO S.OO Sodium monofluorophosphate O.80 O.80 TABLE XIII PHB methyl ester O.15 O.15 PHB propyl ester O.OS O.OS Toothpaste (amounts in 90 b.w. Nasaccharinate O.20 O.20 Flavour (PF1, PF2, PF3 or PF4) 1.OO 1.00 Ingredient INCI A. Herba Santa extract (E. angustifolium) O.SO as per EX. 1 (10% in ethanol) Demin. water Water (deionized) 26.31 Herba Santa extract (E. Californicum) O.25 Sorbitol 70% Sorbitol 70% 7O.O as per EX. 5 (10% in ethanol) US 2013/025 1730 A1 Sep. 26, 2013 24

TABLE XV-continued TABLE XVIII Tooth cream for pain-sensitive teeth (amounts in % b.w.) Soap bar (amounts in 90 b.w. Ingredient INCI A. B Ingredient A. B Demin. water Water 2.5 2.5 Ca carbonate 35.00 3S.OO Soap base mix Sodium tallowates 95.5 95.8 Silicon dioxide 1.00 1.OO palmitates Sodium dodecylsulphate (SDS) 1...SO 1...SO Titanium dioxide Titanium dioxide 1.O 1.O Demin. water Ad 100 Perfume oil P2, Fragrance O.8 P4, P6 or P7 Perfume oil P1, Fragrance O.S P3 or P5 Concentrated Herba Santa extract (E. angustifolium) O.2 TABLE XVI as per Example 4 (10% in ethanol) Concentrated Herba Santa extract (E. californicum) O.2 Gelatine capsules for bad breath for direct as per Example 7 (10% in ethanol) consumption (amounts in 90 b.w. Ingredients A. B C Gelatine casing Glycerine 2014 2014 2014 TABLE XIX Gelatine 240 Bloom 7.91 7.91 7.91 Sucralose O.06S O.06S O.06S Antimicrobial soap bar (amounts in 90 b.w. Allura Red O.OO6 O.OO6 O.OO6 Brilliant Blue O.OOS O.OOS O.OOS Ingredients A. B Core filling Plant oil triglycerides 82.OO 74.OO 6O.OO Flavour B 7.9 15.50 29.5 Sodium soap from tallow 6O.O 60.0 Herba Santa extract O.10 OSO Sodium Soap from palm oil 27.0 27.0 (E. anguistifolium) Glycerol 2.0 2.0 as per EX. 1 Sodium chloride O.S O.S (10% in ethanol) 1-hydroxyethane-1,1-diphosphoric O.3 O.3 Herba Santa extract O.10 O.SO acid, tetrasodium salt (E. californicum) as Alpha-tocopherol O.1 O.1 per Ex. 5 (10% in ethanol) Pigment yellow 1 O.O2 O.O2 Water Ad 100 Perfume oil P2, P4, P6 or P7 3.0 Perfume oil P1, P3 or P5 3.0 0287 Flavour B had the following composition (data in Herba Santa extract (E.) O.S as per Example 1 (10% in ethanol) weight %): 0.1% neotame (powder), 0.05% aspartame, Concentrated Herba Santa extract (E. angustifolium) O.2 29.3% peppermint oil (Avensis), 29.3% peppermint oil (Pip as per Example 7 (10% in ethanol) erita; Willamette), 2.97% sucralose, 2.28% triacetin, 5.4% diethyl tartrate, 12.1% peppermint oil (Yakima), 0.7% etha nol, 3.36% 2-hydroxyethyl menthyl carbonate, 3.0% 2-hy droxypropyl menthyl carbonate, 0.27% vanillin, 5.5% D-li TABLE XX monene, 5.67% L-menthyl acetate. Liquid Soap (amounts in 90 b.W. 0288 The gelatine capsule, which is suitable for direct Ingredient INCI A. B consumption, has a diameter of 5 mm; the weight ratio Tagat O2 PEG-20 Glyceryl oleate 2.5 2.5 between core and casing material is about 90:10. The cap Coconut fatty acid Cocamide DEA S.O S.O Sules open in the mouth in less than 10 secs, and dissolve diethanolamide completely within 50 secs. Abi B8842 Cyclomethicone O.S O.S Sodium laurylether Sodium laureth Sulphate 3S.O 3S.O Sulphate, 28% TABLE XVII Tego-betaine L7 Cocamidopropyl betaine S.O S.O Soap, 25% Coconut acid, potassium 2O.O 2O.O Syndet - soap-free cleansing bar (amounts in 90 b.w. salt, potassium oleate Water Water Ad 100 Ingredient INCI A. B Preservative DMDM hydantoin Perfume oil P2, Fragrance 0.4 Zetesap 813 A Disodium lauryl Sulpho- 92.0 91.9 P4, P6 or P7 Succinate, Sodium lauryl Perfume oil P1, Fragrance 0.4 Sulphate, corn starch, P3 or P5 cetearyl alcohol, paraffin, Concentrated Herba Santa extract (E. angustifolium) 0.4 O.3 titanium dioxide Amphotensid GB 2009 Disodium cocoamphodiacetate 6.O 6.O as per EX. 4 (10% in ethanol) Allantoin Allantoin 1.O 1.O Perfume oil P2, Fragrance 1.O P4, P6 or P7 Perfume oil P1, Fragrance 1.O TABLE XXI P3 or P5 Herba Santa extract (E. angustifolium) O.S Liquid soap (Syndet) (amounts in 90 b.W. as per Example 1 (10% in EtoH) Concentrated Herba Santa extract (E. angustifolium) O.1 Ingredients INCI A. B as per Example 4 (10% in ethanol) Elfan OS46 Sodium olefin C14-C16 35.5 35.5 Sulphonate US 2013/025 1730 A1 Sep. 26, 2013 25

TABLE XXI-continued TABLE XXIV Liquid soap (Syndet) (amounts in 96 b.w.) Anti-dandruff shampoo (all amounts in 90 b.w. Ingredients NCI A. B ngredients INCI A. B Climbazole Climbazole OSO OSO Armoteric LB Lauryl betaine 8.O 8.0 Phenoxyethanol, Phenoxyethanol, methylparaben, O.7O O.70 Elfan SG 1O.O 1O.O methylparaben, ethylparaben, butylparaben, ElfacOS GT282 L Talloweth-60 myristylglycol 3.0 3.0 EN propylparaben, isobutylparaben PCL-Liquid 100 cetearyl ethylhexanoate 4.0 4.0 Propylparaben, Water Water Ad 100 Isobutylparaben Perfume oil P2, Fragrance 0.4 Herba Santa extract (E. angustifolium) 0.60 — P4, P6 or P7 as per EX. 1 (10% in ethanol) C Concentrated Herba Santa extract (E. angustifolium) O4O perful oil P1, Fragrance 0.4 as per EX. 4 (10% in ethanol) 3 or PS Sodium laureth Sulphate Sodium laureth Sulphate 37.OO 37.00 Herba Santa extract (E. angustifolium) O.S Cocamidopropyl betaine Cocamidopropyl betaine 8.OO 8.00 as per EX. 1 (10% in ethanol) PEG-6 PEG-6 caprylic?capric glycerides 2.50 2.50 Herba Santa extract (E. californicum) O.3 Laureth -2 Laureth-2 2.00 2.OO as per EX. 5 (10% in ethanol) Thyme extract Water (aqua), glycerol, OSO OSO Thymus vulgaris (thyme), flowerleaf extract Rosemary extract Rosmarinus officinalis OSO OSO (rosemary) leaf water, TABLE XXII water (aqua), butylene glycol, pentylene glycol Shampoo Bisabolol Bisabolol O.10 O.10 Panthenol Panthenol OSO OSO Ingredients A. B Perfume oil P2, Fragrance OSO - C Sodium lauryl ether Sulphate 12 12 P6 or P7 erfume oil P1, Fragrance OSO (e.g. Texapon NSO) P3 or P5 Cocamidopropylbetaine (e.g. Dehyton K) 2 2 O Sodium chloride 1.4 1.4 Water Water (aqua) 46.3O 46.30 Citric acid 1.3 1.3 Polyguaternium-10 Polyguaternium-10 0.40 0.40 Phenoxyethanol, methyl, ethyl, O.S O.S butyl and propylparaben Perfume oil P2, P4, P6 or P7 O.3 Perfume oil P1, P3 or P5 O.3 TABLE XXV Herba Santa extract (E. californicum) O.25 as per EX. 5 (10% in ethanol) Shower gel (amounts in 90 b.W. Herba Santa extract (E. californicum) O.15 as per EX. 7 (10% in ethanol) Ingredients NCI A. B Water Ad 100 Demin. water Water Ad 100 Plantacare PS10 Sodium laureth Sulphate, 2O.O 200 auryl glucoside TABLE XXIII Dragocid Liquid Phenoxyethanol, O.S O.S methylparaben, 2 in 1 - Shampoo (all amounts in % b.W. ethylparaben,butylparaben, Ingredients NCI A. B propylparaben, isobutylparaben Demineralized water Water Ad 100 Sodium chloride Sodium chloride 1.4 1.4 Plantacare PS10 Sodium laureth Sulphate, 2O.O 20.O Citric acid monohydrate Citric acid 1.3 1.3 auryl glucoside (crystalline) Euperlan PK 771 Glycol distearate, 6.0 6.O Perfume oil P2, Fragrance O.6 sodium lauryl Sul- P4, P6 or P7 phate, cocamide MEA, Perfume oil P1, Fragrance O6 aureth-10 P3 or P5 Dragocid liquid Phenoxyethanol, methyl- O.S O.S Herba Santa extract (E. angustifolium) O.1 paraben, ethylparaben, as per Example 1 (10% in ethanol) butylparaben, Concentrated Herba Santa extract (E. angustifolium) O.OS propylparaben, as per Example 4 (10% in ethanol) isobutylparaben Sodium chloride Sodium chloride 1.4 1.4 Citric acid monohydrate Citric acid O.1 O.1 (crystalline) TABLE XXVI Perfume oil P2, Fragrance O.S P4, P6 or P7 Shaving foam (amounts in 90 b.W. Perfume oil P1, Fragrance O.S P3 or P5 Ingredients A. B Concentrated Herba Santa extract (E. angustifolium) O.15 as per EX. 4 (10% in ethanol) Demin. water 77.2 77.22 Herba Santa extract (E. californicum) O.15 Triethanolamine 4.0 4.0 as per EX. 8 (10% in ethanol) Edenor L2 SM (stearic acid, 5.3 5.3 palmitic acid) (Cognis) US 2013/025 1730 A1 Sep. 26, 2013 26

TABLE XXVI-continued TABLE XXVIII-continued

Shaving foam (amounts in 90 b.w. Deodorant formulation (Roll-on gel) (amounts in % b.w.)

ngredients A. Ingredients A. B Laureth-23 3.0 3.0 Concentrated Herba Santa extract (E. angustifolium) O.10 Stearyl alcohol O.S O.S Euxyl (R) K220 (methylisothiazolinone, O.8 O.8 as per Example 4 (10% in ethanol) ethylhexylglycerol) Water Ad 100 Sodium lauryl Sulphate 3.0 3.0 Extrapone seaweed alga (water, 1.O 1.O propylene glycol, potassium iodide, Fucus Vesiculosus Extract) TABLE XXIX Dragosantol (bisabolol, farnesol) O.1 Perfume oil P2, P4, P6 or P7 Deodorant stick (amounts in % b.w. Perfume oil P1, P3 or P5 Herba Santa extract (E. californicum) Weight Weight as per Example 5 (10% in EtOH) Ingredients % % Concentrated Herba Santa extract as O.08 Sodium stearate 8.OO 8.00 per Example 8 (10% in ethanol) PPG-3 myristyl ether 7O.OO 70.00 Propane, butane 4.2 bar 4.0 4.0 1,2-propylene glycol 1O.OO 10.00 1,1-dimethyl-3-phenylpropanol O.2O O.25 2-butyloctanoic acid O.2O O.20 Perfume oil P2, P4, P6 or P7 O.6O TABLE XXVII Perfume oil P1, P3 or P5 O.60 Herba Santa extract (E. angustifolium) O.30 Aftershave (amounts in % b.w. as per Example 1 (10% in ethanol) Concentrated Herba Santa extract (E. californicum) O.20 Ingredients INCI A. B as per Example 7 (10% in ethanol) Water Ad 100 SymSol (R) PF-3 Water (aqua), pentylene 3.00 3.00 glycol, Sodium lauryl Sulphoacetate, sodium oleoyl sarcosinate, so TABLE XXX dium chloride, disodium Sulphoacetate, sodium AntiperSpirants (amounts in 90 b.W. oleate, sodium Sulphate SymSitive (R) 1609 Pentylene glycol, 1.OO 1.OO ngredients A. B 4-t-butylcyclo-hexanol Frescolat (RML Menthyl lactate O.30 O.30 Reach AZP-908 SUF 24.00 22.OO Glycerol 99.5 P. Glycerol S.OO S.OO Cyclomethicone (pentamer) Ad 100 Water Water (aqua) Ad 100 Polydecene (Silkflo 364 NF) 17.50 2O.OO Extrapone (R) Glacier Glycerol, Water (aqua) 1.OO 1.OO Neo Heliopan OS (ethylhexyl salicylate) 2.50 1.00 Water GW L-menthyl lactate (Frescolate ML) O.25 SymCalmin (R) Butylene glycol, pentylene OSO OSO Polyethylene 3.00 3.00 glycol, hydroxyphenyl Hydrogen. castor oil 2.OO 2.00 propamidobenzoic acid Promyristyl PM-3 7.OO 7.00 Dragosine (R) Carnosine O.10 O.10 PEG-8 distearate 3.00 3.00 Hydrolite (R) 5 Pentylene glycol S.OO S.OO Silicon dioxide (Cab-O-Sil M-5) 1.OO 1.00 Ethanol.96% Alcohol denat. S.OO S.OO Stearyl alcohol 1S.OO 10.00 Colour pigment Colour pigment O.OS O.OS Octyldodecanol 8.00 Perfume oil P2, P4, Perfume O.15 Perfume oil P2, P4, P6 or P7 O.8O P6 or P7 Perfume oil P1, P3 or P5 O.80 Perfume oil P1, P3 Perfume O.15 Herba Santa extract (E. angustifolium) O.30 or PS as per Example 1 (10% in ethanol) Herba Santa extract (E. angustifolium) O.15 Concentrated Herba Santa extract (E. angustifolium) O.30 as per Example 1 (10% in ethanol) as per Example 4 (10% in ethanol) Concentrated Herba Santa extract (E. angustifolium) O.08 as per Example 4 (10% in ethanol) TABLE XXXI

TABLE XXVIII OW lotion (amounts in % b.w. Deodorant formulation (Roll-on gel) (amounts in 90 b.w. Ingredients INCI A. B Ingredients A. B Paraffin oil Paraffin oil S.OO S.OO Isopropyl palmitate Isopropyl palmitate S.OO S.OO 1,3-Butylene glycol 2.OO 2.OO Cetyl alcohol Cetyl alcohol 2.OO 2.00 PEG-40-hydrogen. castor oil 2.OO 2.OO Beeswax Beeswax 2.OO 2.00 Hydroxyethylcellulose OSO O.SO Ceteareth-20 Ceteareth-20 2.OO 2.00 Preservative (phenoxyethanol) O.30 O.30 PEG-20 glyceryl PEG-20 glyceryl 1...SO 1...SO Perfume oil P2, P4, P6 or P7 O.30 Stearate Stearate Perfume oil P1, P3 or P5 O.30 Glycerol Glycerol 3.00 3.00 Herba Santa extract (E. angustifolium) O.30 Perfume oil P2, Perfume O.30 as per Example 1 (10% in EtoH) P4, P6 or P7 US 2013/025 1730 A1 Sep. 26, 2013 27

TABLE XXXI-continued TABLE XXXIII-continued

O/W lotion (amounts in % b.w.) Hand and body cream (amounts in 90 b.w. Ingredients INCI A. B Ingredients INCI A. B Potassium sorbate Potassium sorbate O. 10 O.10 euxyl (R) K300 Methyl, butyl, ethyl, propyl, O.80 O.80 Perfume oil P1, Perfume O.30 isobutylparaben, P3 or P5 phenoxyethanol. Herba Santa extract (E. californicum) O.25 Sodium hydroxide Sodium hydroxide O.SO OSO as per Example 5 (10% in ethanol) 10% solution Concentrated Herba Santa extract (E. californicum) O.10 Perfume oil P2, Perfume 0.20 — P4, P6 or P7 as per Example 7 (10% in ethanol) Perfume oil P1, Perfume — 0.20 Methylparaben Methylparabens O.30 O.30 P3 or P5 Water Water Ad 100 Herba Santa extract (E. angustifolium) as per 0.20 — Example 1 (10% in ethanol) Concentrated Herba Santa extract (E. angustifolium) — 0.15 as per Example 4 (10% in ethanol) TABLE XXXII Body lotion (amounts in 90 b.W. TABLE XXXIV Ingredients INCI A. B Face cream (amounts in 96 b.w. Cetearyl alcohol Cetearyl alcohol 2.00 2.OO Ethylhexyl isononanoate Ethylhexyl isononanoate S.OO S.OO Weight Weight Cetearyl ethylhexanoate, Cetearyl ethylhexanoate, 3.00 3.00 Ingredients INCI % % isopropyl myristate isopropyl myristate Glyceryl oleate citrate, Glyceryl oleate citrate, 4.OO 4.OO Emulsiphos (R) Potassium cetyl 1...SO 1...SO caprylicicapric triglyceride caprylicicapric triglyceride phosphate, hydrogenated Water Water (aqua) 79.50 79.50 palm glycerides Carbomer Carbomer O.30 O.30 Cutina (R) GMS-V Glyceryl Stearate 1.70 1.70 Sodium benzoate Sodium benzoate O.10 O.10 Lanette (RO Cetearyl alcohol 3.00 3.00 Propylene glycol Propylene glycol S.OO S.OO Tegosoft (R) MM Myristyl myristate 1.00 1.OO Triethylene glycol, Triethylene glycol, imida- O.30 O.30 PCL-Liquid 100 Cetearyl ethylhexanoate 1.00 1.OO imidazolidinylurea, Zolidinylurea, methylpara Isodragol (R) Trisononanoin 3.00 3.00 methylparaben, ben, propylparaben, dehy DragoXat (R) 89 Ethylhexyl isononanoate 4.OO 4.OO propylparaben, dehy- droacetic acid Avocado oil Persea gratissina 3.00 3.00 droacetic acid (avocado) oil Sodium hydroxide Sodium hydroxide 30% O.30 O.30 Abi (R) 350 Dimethicone OSO OSO Soln. (30%) solution Cowi-Ox (RT-70 Tocopherol O.10 O.10 Perfume oil P2, P4, Perfume 0.30 — Edeta (RBD Disodium EDTA O.10 O.10 P6 or P7 Carbopol (R) Acrylates/C10-30 alkyl O.30 O.30 Perfume oil P1, P3 or P5 Perfume O.30 Ultrez, 21 acrylate crosspolymer Herba Santa extract (E. angustifolium) as per O.10 Keltrol (R) CG-RD Xanthan gum O.15 O.15 Example 1 (10% in ethanol) Water Water (aqua) Ad 100 Herba Santa extract (E. californicum) as per O.10 Glycerol 99.5 P. Glycerol 4.OO 4.OO Example 5 (10% in ethanol) Propylene glycol- Propylene glycol 3.00 3.00 1,299 PGC Euxyl (R) K712 Sodium benzoate, O.80 O.8O potassium Sorbate TABLE XXXIII SymMatrix (R) Maltodextrin, OSO OSO Rubus finiticosus (blackberry) Hand and body cream (amounts in 90 b.W. eaf extract Ingredients INCI A. B Sodium hydroxide Sodium hydroxide OSO OSO 10% solution Dracorin (R) GOC Glyceryl oleate citrate, 2.00 2.OO Perfume oil P2, Perfume O.30 caprylicicapric triglycerides P4, P6 or P7 PCL-Solid Stearylheptanoate, Stearyl 2.SO 2.50 Perfume oil P1, Perfume O.30 caprylate P3 or P5 Lanette (RO Cetearyl alcohol 1...SO 150 Concentrated Herba Santa extract (E. angustifolium) O.10 Cutina (R) GMS-V Glyceryl Stearate 1.OO 1.OO as per Example 4 (10% in ethanol) DragoXat (R) 89 Ethylhexyl isononanoate 3.00 3.00 Concentrated Herba Santa extract (E. californicum) O.10 PCL-Liquid 100 Cetearyl ethylhexanoate 7.00 7.OO as per Example 8 (10% in ethanol) Isodragol (R) Trisononanoin 4.OO 4.OO Xiameter (RPMX-0345 Cyclopentasiloxane (and) O.SO OSO Cyclosiloxane cyclohexasiloxane Water Water (aqua) Ad 100 TABLE XXXV Carbopol (R) Ultrez 21 Acrylates/C10-30 alkyl acry O.20 O2O late crosspolymer Anti-wrinkle cream (amounts in 96 b.w. Keltrol (R) CG-RD Xanthan gum O. 10 O.10 Glycerol 85 P. Glycerol 3.00 3.00 Ingredients A. DragoBeta Glucan Water (aqua), butylene 1...SO 150 glycol, glycerol, Avena sa Glyceryl Stearate citrate 1.00 1.OO tiva (oat) kernel extract Glyceryl laurate 1.00 1.OO US 2013/025 1730 A1 Sep. 26, 2013 28

TABLE XXXV-continued TABLE XXXVII-continued

Anti-wrinkle cream (amounts in 96 b.w. Sunscreen spray (amounts in 96 b.w.) Ingredients A. B Ingredient NCI A. B Cetearyl alcohol, 2.OO 2.OO Myristyl myristate 1.OO 1.OO Cetearyl ethylhexanoate 4.OO 4.OO Baysilon oil M 10 Dimethicone 1.00 1.OO Mineral oil 4.OO 4.OO Edeta BD Disodium EDTA O.10 O.10 Cyclopentasiloxane, cyclohexasiloxane OSO O.SO Copherol 1250 Tocopheryl acetate OSO OSO PreservativeR. (phenoxyethanoall topolymer O.2O1.OO O.201.OO Cetiol OE Dicaprylyl ether 3.00 3.00 Water Ad 100 Neo Heliopan (R) HMS Homosalate S.OO S.OO Xanthan gum O.10 O.10 Neo Heliopan (RAV Ethylhexyl 6.OO 6.OO 1.2-hexanediol 2.OO 2.OO methoxycinnamate Sodium hydroxide 10% solin. O.10 O.10 Neo Heliopan (R 357 Butyl methoxydibenzoyl- 1.00 1.OO Narcissils Tazetta extract 1.OO 1.OO methane Perfume oil P2, P4, P6 or P7 O.30 C T Diethylhexyl hthal 2.00 2.OO Perfume oil P1, P3 or P5 O.30 orapan TQ ethylhexylnaphthalate Concentrated Herba Santa extract (E. angustifolium) O.10 Alpha Bisabolol Bisabolol O.10 O.10 as per Example 4 (10% in ethanol) Pemulen TR-2 Acrylates/C10-30 alkyl O.25 O.25 caused. Santa N (E. californicum) O.10 acrylate crosspolymer as per EExample 8 (10% in ethanol) Phenoxyethanol Phenoxyethanol O.70 O.70 Solbrol. M Methylparaben O.20 O.2O SolbroP Propylparaben O.10 O.10 TABLE XXXVI NaOH, 10% Sodium hydroxide O60 O.6O Perfume oil P2, P4, P6 Fragrance O.20 Washing and cleansing gel (amounts in 90 b.W. or P7 Ingredient INCI A. B Perfume oil P1, P3 or Fragrance O.2O Water Water (aqua) Ad 100 P5 Pioner (RNP 37 G Sodium carbomer 1...SO 150 Concentrated Herba Santa extract (E. californicum) O.10 SymSol (R) PF-3 Water (aqua), pentylene glycol, S.OO S.OO as per Example 8 (10% in ethanol) sodium lauryl Sulphoacetate, Concentrated Herba Santa extract (E. angustifolium) O.10 sodium oleoyl sarcosinate, sodium chloride, disodium as per Example 4 (10% in ethanol) Sulphoacetate, sodium oleate, sodium Sulphate Hydroviton (R) 24 Water (aqua), pentylene glycol, 1.OO 1.OO glycerol, Sodium lactate, TABLE XXVIII actic acid, serine, urea, sorbitol, Sodium chloride, Sunscreen milk (WO) (amount in % b.w. allantoin Extrapone (R) Silk GW Water (aqua), glycerol, 1.OO 1.OO Ingredients NCI A. B hydrolyzed silk Hydrolite (R) 5 Pentylene glycol 4.OO 4.OO Dehymuls PGPH Polyglyceryl-2 dipoly- 3.00 3.00 Preservative Phenoxyethanol hydroxystearate Actipearls Red Star # Water (aqua), propylene glycol, 1.OO 1.OO Beeswax 8100 Beeswax 1.OO 1.OO DH10402.6 algin, gellan gum, xanthan Monomuls 90-0-18 Glyceryl oleate 1.OO 1.OO gum, calcium chloride, CI Zinc stearate Zinc stearate 1.OO 1.OO 2490 (Pigment Red 5), mica Cetiol SN Cetearyl isononanoate S.OO S.OO (CI 77019), titanium dioxide Cetiol OE Dicaprylyl ether S.OO S.OO (CI 77891) Tegosoft TN C12-15 alkylbenzoate 4.OO 4.OO Perfume oil P2, Perfume OSO - Vitamin E Tocopherol OSO OSO P4, P6 or P7 Neo Heliopan (R) OS Ethylhexyl salicylate S.OO S.OO Perfume oil P1, Perfume - OSO Neo Heliopan (RAV Ethylhexyl methoxycinnamate 7.50 7.50 P3 or P5 Uwinul (RT150 Ethylhexyl triazone 1...SO 150 Herba Santa extract (E. angustifolium) O.2 Demin. water Water (aqua) Ad 100 as per Example 1 (10% in ethanol) Trilon BD Disodium EDTA O.10 O.10 Concentrated Herba Santa extract (E. californicum) - O.25 Glycerol Glycerol S.OO S.OO as per Example 7 (10% in ethanol) Solbrol. M Methylparaben O.20 O2O Phenoxyethanol Phenoxyethanol O.7O O.70 SolbroP Propylparaben O.10 O.10 Neo Heliopan (RAP 10% Disodium phenyl 1S.OO 15.OO TABLE XXXVII Solution, neutralized dibenzimidazole with NaOH etraSulphonate Sunscreen spray (amounts in 90 b.w.) Perfume oil P2, P4, P6 or Perfume O.25 - P7 Ingredient INCI A. B Perfume oil P1, P3 or P5 Perfume O.25 Herba Santa extract (E. angustifolium) 0.15 — Demineralized water Water (aqua) 69.40 69.40 as per Example 1 (10% in ethanol) Glycerol Glycerol 4.OO 4.OO Concentrated Herba Santa extract (E. angustifolium) O.1 1.3 Butylene glycol Butylene glycol S.OO S.OO as per Example 4 (10% in ethanol) D-Panthenol Panthenol OSO O.SO Alpha bisabolol Bisabolol O.10 O.10 Lara Care A-200 Galactoarabinan O.25 O.25 US 2013/0251 730 A1 Sep. 26, 2013 29

TABLE XXXIX TABLE XXXXI

After-Sun Gel (amounts in % b.w.) Solution for wet wipes (amounts in 90 b.w. Ingredients INCI A. B Ingredients INCI SymSol (R) PF-3 Water (aqua), pentylene 2.00 2.00 SymSol (R) PF-3 Water (aqua), pentylene 3.OOO 3.OOO glycol, Sodium lauryl glycol, sodium lauryl Sulphoacetate, sodium oleoyl sarcosinate, sodium Sulphoacetate, sodium chloride, disodium oleoyl sarcosinate, Sulphoacetate, sodium Sodium chloride, oleate, sodium Sulphate disodium Sulphoacetate, Dragosantol (R) 100 Bisabolol O. 10 O.10 Sodium oleate, sodium Glycerol 99.5 P. Glycerol S.OO S.OO Sulphate Water Water (aqua) Ad 100 Hydrolite (R) 5 Pentylene glycol S.OO S.OO Glycerol 99.5 P. Glycerol S.OOO S.OOO Preservative Phenoxyethanol SymHelios (R) 1031 Benzylidene dimethoxy O.100 O.100 D-Panthenol 75W Panthenol O.80 O.80 dimethylindanone DragoCalm (R) Water (aqua), glycerol, 1.OO 100 Water Water (aqua) q.s.p. 100 q.s.p. 100 Avena Saiva (oat) kernel extract Pemulen (RTR-2 Acrylates/C10-30 alkyl 1.OOO 1.OOO Hamameis Distillate Hamamelis virginiana 1.O 1.00 acrylate crosspolymer (witch hazel) water, D-Panthenol 75W Panthenol O.SOO OSOO water (aqua), alcohol SymFinity (R) 1298 Echinacea Purpurea O.100 O.100 Allplant Essence (R) Org. Rose Pelargonium graveolens 1.OO 100 Geranium P flowerleaf stem water extract Perfume oil P2, P4, P6 or P7 Perfume 0.10 — Extrapone (R) Water (aqua), glycerol, 1.OOO 1.OOO Perfume oil P1, P3 or P5 Perfume — 0.10 Pearl GW hy rolyzed pearl, Herba Santa extract as per Example 1 0.30 — X8. han gun (E. angustifolium) (10% in ethanol) Sodium hydroxide So ium hydroxide 2.500 2.SOO Concentrated Herba Santa extract (E. californicum) — 0.20 as per Example 8 (10% in ethanol) O% solin. Preservatives Methyl, butyl, ethyl, 1.OOO 1.OOO propylparaben, phenoxyethanol Test Studies Ethanol.96% Alcohol denat. 1S.OOO Perfume oil P2, Perfume O.20 Example TS1 P4, P6 or P7 Perfume oil P1, Perfume O.20 Test Study Anti-Inflammatory Action in P3 or P5 LPS-Induced Human Monocytes Herba Santa extract (E. angustifolium) O.1 0289. The anti-inflammatory test was performed in a cell as per Example 1 (10% in e hanol) culture system using human monocytes. Human monocytes Concentrated Herba Santa extract O.OS are one of the main cell types which are involved in inflam (E. anglisiifolium) as per Example matory processes in tissues; they are the cells which are 4 (10% in ethanol) mainly influenced by the lipopolysaccharides (LPS) pro duced by gram-negative bacteria. Further, they represent the first step in the cascade of the inflammatory reactions, in that TABLE XXXX they release various cytokines, e.g. interleukin-1beta, inter leukin-6, interleukin-8 and tumour necrosis factor alpha After-sun lotion (amounts in % b.w. (TNFC), but also other inflammation parameters (e.g. pros taglandin E2). The parameters measured here are recognized ngredients A. B inflammation mediators. The use of primary human mono Acrylat C10-30 alkyl acrylate crosspolymer 0.4 0.4 cytes enables a realistic portrayal of the pathophysiological Cetearyl ethylhexanoate 1S.O 1S.O situation. Bisabolol O.2 O.2 Tocopheryl acetate 1.O 1.O 0290 For the experiments, human primary monocytes Panthenol 1.O 1.O were sown into 24-well plates (ca. 500,000 cells/ml in 1 ml). Alcohol 1S.O 1S.O The cell viability was determined by means of the Alamar Glycerol 3.0 3.0 Blue method or by measurement of the intracellular ATP Perfume oil P2, P4, P6 or P7 O.30 level. Perfume oil P1, P3 or P5 O.30 Herba Santa extract (E. angustifolium) O.25 0291. The cells were incubated with the stimulus (LPS) as per Example 1 (10% in ethanol) for 24 hrs. Solutions of the Herba Santa extract according to Concentrated Herba Santa extract (E. angustifolium) O.15 Example 1 and an extract rich in erionic acid according to as per Example 4 (10% in ethanol) Pentylene glycol 4.0 4.0 Example 4 were added 30 mins before the treatment with Preservatives (methyl, butyl, ethyl, 1.O 1.O LPS. After 24 hrs, the supernatant was removed, centrifuged propylparaben, phenoxyethanol) and investigated according to the operating instructions of the Demin. water Ad 100 particular manufacturer of the immunoassay used. The results Triethanolamine O.2 O.2 are shown in FIG. 2a (Herba Santa extract according to Example 1) and FIG.2b (extract rich in erionic acid according to Example 4). US 2013/025 1730 A1 Sep. 26, 2013 30

0292 Adding of the Herba Santa extract according to 0296 (c) the flavonoid fraction (“FF) obtained as a by Example 1 to cells treated with LBS led to a serious reduction product according to Example 4 (containg 41.5% HED, 0.1 of the determined inflammation markers. The effect using the uM, 1 uM and 10 uM calculated on HED); extract rich in erionic acid according to Example 4 were even 0297 (d) the extract rich in erionic acid (“ES) according more significant. to Example 4 or isolated erionic acid B (according to Example 2) and Example TS2 0298 (e) erionic acid C according to Example 3 (each 0.1 Anti-Inflammatory Action in Human Gingival uM, 1 uM and 10 uM). Fibroblastic Cells (HGF-1) 0299. After incubation the cell culture medium was trans 0293 Human gingival fibroblastic cells (HGF-1) were ferred into an Eppendorf reaction vessel and at 4°C. for 10 sowed out in 24-well plates with 15,000 cells per well and min subjected to centrifugation (1000xg) in order to separate cultivated for 3 to 5 days. DNEM containing 10% FBS, 1% the cell depris. The upper layer was stored at -80°C. until the penicillin/streptomycin and 4% glutamine was used as the analysis started. The results of the release of IL-6 and medium. For determination of the anti-inflammatory action 0300 IL-8 after 6 and 9 hrs are shown in FIGS.3a to 3e. In the cells were incubated with 10 g/ml PG-LPS for 6 and 9 Some of the tested concentrations and after certain times of hrs. Subsequently, the release of IL-6 and IL-8 per magnetic treatment adding of the Herba Santa extract according to bead was determined (Procarta, Affimetrix) using a MAGPIX Example 1 also led to a reduction of IL-6 and IL-8 release equipment (Merck-Millipore) and analysed using the Milli (FIG.3a). Adding of the extracts FF and ESled to a significant plex software (Merck Millipore). In each case 4 samples with reduction in IL release (FIGS. 3b, 3c); the same is true for the two technical replicates were measured. In addition to this addition of erionic acid B (FIG. 3d). The most significant control the cells were co-incubated with reduction could be shown for erinoic acid C (FIG. 3e): at 0294 (a) 10 g/ml PG-LPS and also with higher concentration the release of IL-6 and IL-8 was almost 0295 (b) solutions of the Herba Santa extract according to completely inhibited. Example 1 (HS, containing 21.7% HED, 0.1 uM, 1 uMand 0301 In the following Tables 3a to 3e the asterisks mean: 10 uM calculated on HED); *p-0.05, **p<0.01, ***p<0.001. TABLE 3a

Release of IL-6 and IL-8 by HGF-1 cells after stimulation with 10 g/ml PG-LPS or respectively co-incubation with Herba Santa extract of Example 1 (HS, concentration calculated on contained Homoeriodictyol, HED)

IL-6 IL-8 IL-6 Standard IL-8 Standard Test Compound T/C 96) Deviation T/C 96) Deviation

10 g/ml LPS control - 6h 1OOOO 35.66 98.91 9.06 10 pg/ml LPS + 0.1 M HED in HS-6 h 74.54 1831 117.33: 9.78 10 pg/ml LPS + 1 M HED in HS-6 h 61.90** 13.48 120.57 34.88 10 pg/ml LPS + 10 MHED in HS - 6 h 47.97% : 15.55 131.33:8: 37.98 10 g/ml LPS-control - 9 h 1OOOO 1 OSO 1OOOO 13.67 10 pg/ml LPS + 0.1 M HED in HS-9 h 127.27 56.92 101.45 15.92 10 pg/ml LPS + 1 M HED in HS-9 h 127.80% 26.77 139.93% 33.49 10 pg/ml LPS + 10 MHED in HS - 9 h 73.12 20.93 62.92*** 8.38

TABLE 3b Release of IL-6 and IL-8 by HGF-1 cells after stimulation with 10 g/ml PG LPS or respectively co-incubation with the flavonoid extract (FF) of Example 4 IL-6 IL-8 IL-6 Standard IL-8 Standard Test Compound T/C 96) Deviation T/C 96) Deviation 10 g/ml LPS-Control - 6h 100.00 35.66 98.91 9.06 10 pg/ml LPS + 0.1 M HED in FF-6 h 56.58** 12.39 79.04 51.34 10 pg/ml LPS + 1 M HED in FF-6 h 32.93 * * * 9.55 40.99*** 7.95 10 g/ml LPS + 10 MHED in flavonoid 63.65* 12.09 41.76* * * 9.SO fraction - 6 h 10 g/ml LPS-Control - 9 h 100.00 1 OSO 1OOOO 13.67 10 pg/ml LPS + 0.1 M HED in FF-9 h 60.87:8: 22.17 46.73* * * 16.38 10 pg/ml LPS + 1 M HED in FF-9 h 55.88% 36.35 38.73*** 36.35 10 pg/ml LPS + 10 MHED in FF-9 h 57.15*** 24.38 57.23* * * 1880 US 2013/025 1730 A1 Sep. 26, 2013 31

TABLE 3c Release of IL-6 and IL-8 by HGF-1 cells after stimulation with 10 g/ml PG-LPS or respectively co-incubation with the extract rich in erionic acid (ES) of Example 4

IL-6 IL-8 IL-6 Standard IL-8 Standard Test Compound T/C 96) Deviation T/C 96) Deviation 10 g/ml LPS-Control - 6h 100.00 35.66 98.91 9.06 10 g/ml LPS + 1 g/ml ES - 6h 101.00 5.25 117.56 25.82 10 g/ml LPS + 10 pg/ml ES - 6 h 69.31% 14.O1 68.29** 13.30 10 g/ml LPS + 100 g/ml ES - 6h 67.24: 13.42 50.1888 11.27 10 g/ml LPS-Control - 9 h 100.00 1O.SO 100.00 13.67 10 g/ml LPS + 1 g/ml ES - 9 h 38.86*** 11.18 67.36* 25.84 10 g/ml LPS + 10 pg/ml ES-9h 46.62** 13.47 78.74 16.33 10 g/ml LPS + 100 g/ml ES - 9 h 42.00*** 13.20 21.99* * * 5.38

TABLE 3d Release of IL-6 and IL-8 by HGF-1 cells after stimulation with 10 g/ml PG-LPS or respectively co-incubation with the erionic acid B of Example 2

IL-6 IL-8 IL-6 Standard IL-8 Standard Test Compound T/C96) Deviation T/C 9%) Deviation 10 g/ml LPS-Control - 6h 1OOOO 35.66 98.91 9.06 10 g/ml LPS + 1 g/mlerionic acid B - 6h 61.93: 1998 79.91 14.03 10 g/ml LPS + 10 pg/mlerionic acid B - 6h 102.30 2.56 134.54** 1989 10 g/ml LPS + 100 g/mlerionic acid B - 6 h 41.30** S.29 46.30** 1981 10 g/ml LPS-Control - 9 h 1OOOO 1O.SO 1OOOO 13.67 10 g/ml LPS + 1 g/mlerionic acid B - 9 h 77.51: 13.53 77.33 4922 10 g/ml LPS + 10 g/mlerionic acid B-9h 6147*** 10.05 71.35 28.24 10 g/ml LPS + 100 g/mlerionic acid B - 9h 102.74 2S.O2 116.34 40.91

TABLE 3e Release of IL-6 and IL-8 by HGF-1 cells after stimulation with 10 g/ml PG-LPS or respectively co-incubation with the erionic acid C of Example 3

IL-6 IL-8 IL-6 Standard IL-8 Standard Test Compound T/C96) Deviation T/C96) Deviation 10 g/ml LPS-Control - 6h 1OOOO 35.66 98.91 9.06 10 g/ml LPS + 1 g/mlerionic acid C - 6h 76.66 22.32 94.59 23.76 10 g/ml LPS + 10 pg/mlerionic acid C - 6h 65.22% 32.24 62.478 25.75 10 g/ml LPS + 100 g/mlerionic acid C - 6 h 5.11: * * 3.41 0.67* * * O.64 10 g/ml LPS-Control - 9 h 1OOOO 1O.SO 1OOOO 13.67 10 g/ml LPS + 1 g/mlerionic acid C-9 h 53.26** 22.53 39.13* * * 13.83 10 g/ml LPS + 10 pg/mlerionic acid C-9 h 56.22* * * 15.62 39.00* * * 13.38 10 g/ml LPS + 100 g/mlerionic acid C-9 h 7.67:8: 6.85 149* * * 1.83

1-30. (canceled) or any salt of a compound of the formula (X) or any mixture containing or consisting of two or more different com 31. A compound of the formula (X) pounds of the formula (X), two or more different salts of compounds of the formula (X) or one or more different compounds of the formula (X) and one or more different (X) salts of compounds of the formula (X), whereinfor R1, R2 and R3 independently of one another in every compound of the formula (X) the following applies: R1 is hydrogen or methyl, R2 is an organic residue with 5 carbon atoms and one oxygen atom or none and R3 is an organic residue with 10 carbon atoms and one or more OXygen atoms, O R1 and R2 together with the carbon atoms in positions 4 and 5 and the oxygenatom bound to the carbon atom in US 2013/025 1730 A1 Sep. 26, 2013 32

position 4 form a ring and comprise 5 carbon atoms and 33. The compound, salt or mixture of claim 31, wherein one oxygen atom or none, and one, several or all compound(s) of the formula (X) is selected R3 is an organic residue with 10 carbon atoms and one or or are each selected independently of one another from the more OXygen atoms. group consisting of the following compounds (1) to (10): 32. The compound, Salt or mixture according to claim 31, wherein for the groups R1,R2 and R3 in the compound of the formula (X) or independently of one another in one, several or Erionic acid A (1) all, preferably all, compound(s) of the formula (X) the fol lowing applies: R3 is

Erionic acid B (2)

wherein the dotted line which links the carbon atoms designated as B and C denotes a single bond or a double bond is present between these carbon atoms, and the dotted line which links the carbonatoms designated as E and G means an individual double bond, which is posi tioned either between the carbon atoms designated as F and G or between the carbon atoms designated as E and F, R7 for the case where the double bond is positioned between the carbon atoms designated as E and F, is a Erionic acid C (3) hydroxy group or, for the case where the double bond is positioned between the carbon atoms designated as F and G, is absent, R5 and R6 is a hydrogen atom and a hydroxy group or together are an oxygen atom, the dashed line marks the bond which links R3 with the carbon atom in position 3; R1 is hydrogen or methyl and R2 is Erionic acid D (4)

wherein R4 is hydrogen or a hydroxy group and the dashed line marks the bond which links R2 with the carbon atom in position 5 O Erionic acid E (5)

R1 and R2 together is

Erionic acid F (6)

wherein the dashed line (a) marks the bond which links the tertiary carbon atom with the oxygen atom bound to the carbon atom in position 4 and the dashed line (b) marks the bond which links the secondary carbon atom with the carbon atom in position 5. US 2013/025 1730 A1 Sep. 26, 2013

-continued more different hydroxyflavones of the formula (Y) and Eriolic acid A (7) one or more different salts of hydroxyflavones of the formula (Y), wherein for Q1, Q2, Q3, Q4, Q5, Q6, Q7. Q8 and Q9 independently of one another in each hydroxyflavone of the formula (Y) the following applies: Q1 to Q9 independently of one another is hydro gen atoms, hydroxy groups, methyl, ethyl, 1-propyl. methoxy, ethoxy, 1-propyloxy or 2-propyloxy groups, with the proviso that at least one of the residues Q1 to Q9 represents a hydroxy group.

Eriolic acid B (8) 37. The mixture of claim 36, wherein the following applies: Q2, Q4, Q5, Q8 and Q9 represent hydrogen atoms, Q1, Q3 and Q6 independently of one another are hydrogen atoms, hydroxy or methoxy groups, with the proviso that at least one of the residues Q1 and Q3 represents a hydroxy group and Q7 represents a hydroxy group. 38. The mixture of claim 36, containing one, several or all compounds of the formula (Y) selected from the group con Eriolic acid C (9) sisting of homoeriodictyol. Sterubin, eriodictyol. hesperetin, chrysoeriol and luteolin, preferably comprising homoeriod ictyol. 39. The mixture of claim 36, wherein the proportion of the total quantity of compounds of the formula (X) and salts of compounds of the formula (X) in the mixture, based on the total weight of the mixture, is 1 to 99 wt.%. and/or the proportion of the total quantity of compounds of the formula (Y) and salts of compounds of the formula (Y) in the mixture, based on the total weight of the mixture, is 1 to 99 wt.%. 40. The mixture of claim 36, wherein the proportion of the total quantity of compounds of the formula (X), compounds of the formula (Y), salts of compounds of the formula (X) and salts of compounds of the formula (Y) in the mixture, based on the total weight of the mixture, is 0.0001 to 100 wt.%. 41. The mixture of claim 36, wherein the mixture com 34. The mixture of claim 31, containing or consisting of prises a plant extract or consists thereof, and the proportion of two or more different compounds of the formula (X), prefer the total quantity of compounds of the formula (X) and salts ably of two, three, four, five, six, seven, eight, nine or ten of compounds of the formula (X) in the mixture, based on the different compounds of the formula (X). total weight of the mixture, is preferably 0.1 to 100 wt.%. 35. The mixture of claim 33, containing or consisting of 42. The mixture of claim 36, wherein the plant extract is an two or more different compounds of the formula (X) selected extract from Eriodictyon ssp. from the group consisting of the compounds (1) to (10). 43. The mixture of claim 36, wherein the ratio of the total 36. A Mixture comprising a compound of the formula (X) quantity of compounds of the formula (X) and salts of com or a salt of the formula (X) to claim 31, additionally compris pounds of the formula (X) to the total quantity of compounds ing a hydroxyflavone of the formula (Y) of the formula (Y) and salts of compounds of the formula (Y) lies in the range from 0.00001:1 to 1:0.00001 based on the weight.

(Y) 44. A preparation comprising a compound, a salt or a mixture as defined in claim 31, for the prophylaxis and/or treatment of inflammation. in particular of inflammation of the skin. 45. The preparation of claim 44, which is a food or enjoy ment preparation, a pharmaceutical preparation, a cosmetic preparation or a dermatological preparation. 46. The preparation of claim 44, additionally containing one or more further components selected from the group consisting of probiotic bacteria, prebiotics, Synbiotics, ballast Substances, whey proteins, soya proteins, minerals, toco pherols, Vanilla, Vanilla extracts, omega-3 fatty acids, citrus, or a salt of a hydroxyflavone of the formula (Y) or a mixture apple, grape seed, green tea, rosemary, tarragon, thyme, containing or consisting of two or more different horseradish and mace extracts, tannins, tomato, melon and hydroxyflavones of the formula (Y), two or more differ rosehip extracts, beta-carotene; aubergines, rhubarb, red ent salts of hydroxyflavones of the formula (Y) or one or onions, red cabbage, black carrot, Superfruits, in particular US 2013/025 1730 A1 Sep. 26, 2013 34 agai, noni, goji, pomegranate, mangosteen, currants, Straw (b) a method for strengthening damaged or undamaged berries, aronia, blueberries and/or elderberries, preferably in skin, and/or the form of dried fruit, extracts or fruit preparations; soya (c) a method for reducing tissue damage, and/or isoflavones, nonsteroidal antiinflammatory drugs, antibiot (d) a method for recreating a normal cellular composition ics, budesonide, systemically active steroids, Sulfasalazine, in the intestine, and/or azathioprine/6-mercaptopurine, methotrexate, anti-TNF-al (e) a method for recreating or stabilizing the function of pha antibodies, bisabolol, sodium lauryl-sulphate, chlorhexi skin. dine, metal fluorides, organic and inorganic fluorides, fla 51. A process for obtaining the mixture of claim 36 com vourings, essential oils, cooling active Substances, in prising the following steps: particular menthol, extracts of pure Substances from eucalyp (a) extraction of plant material from Eriodictyon ssp., pref tus, thyme, wintergreen, spearmint and peppermint. erably from Eriodictyon Califormicum and/or Eriodic 47. The preparation of claim 44, for the treatment of animal tyon angustifolium, so that a mixture is formed which or human skin which requires a treatment with anti-inflam contains compounds of the formula (X), optionally com matory active Substances. 48. A method for the prophylaxis and/or treatment of pounds of the formula (Y) and other extracted com inflammation comprising administering a compound or salt pounds, and of formula (X) or mixture according to claim 31. (b) concentration of extracted compounds of the formula 49. The method of claim 48 for at least one of (X) and/or salts of the extracted compounds of the for a) prophylaxis and/or treatment of inflammation of the mula (X) and optionally compounds of the formula (Y) skin, and/or salts of the extracted compounds of the formula b) reducing the release of TNF-alpha, (Y) in the mixture by partial or complete removal of c) reducing the release of an interleukin, other extracted compounds and optionally removal of d) reducing the release of a prostaglandin, or extractants and/or solvents. e) reducing the release of interferon-gamma and/or NF-kB. 52. The process of claim 51, wherein the proportion of the 50. The method of claim 49, wherein the method for the total quantity of compounds of the formula (X) and salts of prophylaxis and/or treatment of inflammation is or comprises compounds of the formula (X) in the mixture based on the (a) a method for the prophylaxis and/or treatment of total weight of the mixture is 0.1 to 100 wt.%. chronic inflammatory diseases and/or k k k k k