(12) Patent Application Publication (10) Pub. No.: US 2015/0140141 A1 Milow Et Al

Home , Aromadendrin, Fustin, Garbanzol, Phellamurin, Pinobanksin

US 2015O140141A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0140141 A1 Milow et al. (43) Pub. Date: May 21, 2015

(54) METHODS FOR BOTANCAL AND/OR Publication Classification ALGAE EXTRACTION (51) Int. Cl. (71) Applicants: BASF CORPORATION, FLORHAM A6R8/97 (2006.01) PARK, NJ (US); BASF BEAUTY A61O 19/00 (2006.01) CARE SOLUTIONS FRANCE SAS, A61O I/06 (2006.01) Lyon (FR) A61O I/14 (2006.01) A61O 19/10 (2006.01) (72) Inventors: Clifford A. Milow, Massapequa, NY A618/49 (2006.01) (US); Laurent Bailly, Essey Les Nancy A61O 1704 (2006.01) (FR); Christopher Judd, Riverhead, NY (52) U.S. Cl. (US); Nicole Jeannine Richter, Port CPC. A61K 8/97 (2013.01); A61K 8/498 (2013.01); Jefferson, NY (US) A61O 19/00 (2013.01); A61O 1704 (2013.01); (73) Assignees: BASF BEAUTY CARE SOLUTIONS A61O 1/14 (2013.01); A61O 19/004 (2013.01); FRANCE SAS, Lyon (FR); BASF A61O 19/10 (2013.01); A61O 19/005 CORPORATION, FLORHAMPARK, (2013.01); A61O I/06 (2013.01) NJ (US) (21) Appl. No.: 14/402.719 (57) ABSTRACT (22) PCT Fled: Jun. 6, 2013 The present disclosure relates to methods for extraction of biomass. Biomass of most interest is that which contains (86) PCT NO.: PCT/US2O13/044464 biologically active, extracts suitable for the skin care market. S371 (c)(1), The biomass of interest includes botanicals (plant extracts (2) Date: Nov. 21, 2014 and bioferments thereof), algae (red, brown, green and red, including bioferments thereof), fungi and even animal Related U.S. Application Data extracts (insect, crustacean) origin. Further the use of said (60) Provisional application No. 61/656.221, filed on Jun. extracts in cosmetic preparations prepared by the disclosed 6, 2012. method is envisioned. Patent Application Publication May 21, 2015 Sheet 1 of 2 US 2015/O140141 A1

000’0 W Patent Application Publication May 21, 2015 Sheet 2 of 2 US 2015/O140141 A1

5% FuCuS VesiculoSuS Extraction in Water On Left And Extraction 10% Pluronic F127/Water Solution On The Right. FIG.2 US 2015/O 140141 A1 May 21, 2015

METHODS FOR BOTANCAL AND/OR 0009 B. Description of Related Art ALGAE EXTRACTION 00.10 Extracts may be obtained from the whole plant, algae or fungi (i.e., the entire plant is used to prepare the 0001. This application takes the benefit of U.S. Provi extract) or from a part of the plant (e.g., leaf, stem, root, sional Application No. 61/656.221 filed Jun. 6, 2012, the flower, seed, sap, bark, etc.). The extracts can also be derived contents herein incorporated entirely by reference. by fermentation which helps to breakdown the cellular tissue of the algae or plant, thereby possibly increasing the bioavail BACKGROUND OF THE INVENTION ability of the naturally occurring bioactive targets. 0011. During extraction typically more than one com 0002 A. Field of the Invention pound is extracted from the botanical or algae and will fre quently range from at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 0003. The present invention relates to methods for extrac 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, tion of biomass. Biomass of most interest is that which con 30, 31, 32, 33, 34, or 35 of differing extractants in a single tains biologically active extracts suitable for the skin treat composition. ment market. The biomass of interest includes botanicals 0012. The skin active targets of particular interest are the (plants and bioferments thereof), algae (red, brown, green and flavonoids and flavonoid derivatives. red, including bioferments thereof), fungi and even animal 0013 Typically the plant (or any part of the plant such as (insect, crustacean) origin and the use of said extracts in the leaves, stems, bark, roots, fruit, flowers or flower buds, cosmetic preparations prepared by the disclosed method. seeds, seed pods, sap, whole plant, etc.) is disrupted by 0004. These natural product hydrophobic extracts are mechanical means which results in a puree. The puree is then often used in cosmetic and pharmaceutical application. Natu processed to be substantially free of impurities or undesired ral products, particularly botanically, fungi and algae derived solids. The puree can then be poured into a shallow vessel and such as flavonoids or flavonoid derivatives, have demon quickly exposed to low temperature, i.e., flash frozen, for strable beneficial properties on the skin and hair. For example, example at -20 degrees centigrade or lower, preferably under these extracts have demonstrated antimicrobial, antiseptic, a vacuum for removal of water content (lyophilization). anti-inflammatory, antioxidant, enzyme stimulation or inhi 0014 Aqueous, alcoholic, or oil based extraction tech bition, pigmentation enhancement or control, photoprotec niques, or combinations thereof, have also been used in the tive, treatment of skin aging, skin imperfections, dry skin, past and are used on the whole plant or any part thereof of photodamaged skin, wrinkles, age spots, acne, skin lighten (e.g., leaves, stems, bark, roots, fruit, flowers or flower buds, ing, psoriasis, and atopic dermatosis. seeds, seedpods, sap, whole plant, etc.) to produce an extract. 0005. The botanical, algae and fungal species are for In such a process, the desired part of the plant or the whole example any botanical, algae or fungal species which may plant is crushed up (e.g., blender) and then extracted with the server as a source for flavonoid or flavonoid derivatives. desired solvent (e.g., water, alcohol, waterfalcohol, or oil 0006 More particularly for example the biomass may be based solvents) to obtain the desired extract. The extract can selected from but is not limited to the group consisting of then be stored in liquid form, lyophilized, or subject to further Acacia Senegal, Achillea millefolium, Aloe barbadensis, Ana processing techniques (e.g., heating, cooling, etc.). Extrac nus sativus, Argania spinosa, Avena sativa, Cassia alata, tion processes are well-known to those having ordinary skill Cocoa Callus, Cocos nucifera, Bupleurum falcatum, Buty in the extract field (e.g., maceration, infusion, percolation, rospermum parkii, Calluna vulgaris, Camelia sinensis, digestion, decoction, hot continuous extraction, aqueous-al Chondrus crispus, Centella asiatica, Ceratonia siliqua, Ces coholic extract, counter current extract, microwave assisted trum latifolium, Cinnamomum cassia, Citrus limon, Coffea extraction, ultrasound extraction, Supercritical fluid extracts, Arabica, Cola acuminate, Cucumissativus, Durio zibethinus, phytonic extract (e.g., with hydro-fluoro-carbon solvents), Glycine soia (Soybean), Glycyrrhiza glabra, Gymnema etc. Sylvestre, Haslea Ostrearia, Heliantus annuus, Hibiscus abel 0015. It is known that certain surfactant water based sys moschus, Humulus lupulus, Laminaria digitata, Lepidium tems may be used for extraction of various hydrocarbons. For meyenii, Linum usitatissimum, Macadamia termifolia, Malva example, Calvert, T. L. et al. AICHE Journal, (1994), Vol. 40. Sylvestris, Melissa officinalis, Morus alba, Morus bombycis, #9, p 1449-1457: Hurter, P. N. et al. Langmuir 1992, 8, Nereocystis luetkeana, Olea europaea, Orthosiphon sta 1291-1299 teach the extraction of hydrocarbons from water mineus, Palmeria palmate, Peucedanum graveolens, Peumus waste systems. boldus, Pisum sativum, Pueraria lobata, Punicia granatum, 0016. Additionally, it is also known that some ethanol Pyrus malus, Rheum palmatum, Rhodiola crenulata, Ros derived plant extracts can be solubilized in aqueous solutions marinus officinalis, Saxifraga sarmentosa, Sarrcodiotheca containing poly(ethylene-oxide)-poly(propylene oxide) gaudichaudii, Scutellaria baicalensis, Serenoa serrulata, copolymers (V Dinoiu. et al. Revista de Chimie, 62/4, 396 Spirulina platensis, Theobroma cacao, Tuber magnatum, 400). 0017. Further, U.S. Serial No. 2012/0010390 discloses the Uncaria tomentosa, Vitis vinifera, Ptychopetalum Olacoides, use of aqueous two phase systems for isolation of biomol Zea mays and Zingiber officinale. ecules or target compounds such as an antibody or a protein 0007. In particular extracts from algae are of special inter from a fermentation broth using ethylene oxide and propy est. For example, extraction of Chondrus crispus, Nereocystic lene oxide random copolymers dissolved in one of the liquid luetkeana and Sarrcodiotheca gaudichaudii, Fucus vesiculo phases. PCT application No. WO2012011589 discloses a sus, Sarcodiotheca gaudichaudii, Ulva lactuca, Laminaria method for the manufacturing of fat-soluble bioactive sub longicruris, Nannochloropsis oculata, Tetraselmis suecica stances extracted from microbial cells using an organic Sol are of special interest. vent in combination with a Surfactant. 0008 Extracts from plants such as Cassia alata, Argania 0018. There are however numerous disadvantages to spinosa and Cocoa Callus are also of preferred interest. extracting with solvents or even water especially when the US 2015/O 140141 A1 May 21, 2015 extracts of interest are lipophilic, hydrophobic or ing liquid. It would be highly desirable to improve this filter amphiphilic. Although water is environmentally friendly, it is ing step by speeding up the filtering process and the elimina limited as an effective extracting solvent when the desired tion of multiple filters. extractants are hydrophobic. Organic solvents are less desir able because of their possible flammability and environmen BRIEF DESCRIPTION OF THE DRAWINGS tal drawbacks. Furthermore, when the extractants are desired for use in cosmetics, in particular skin active cosmetics Such 0024 FIG. 1 is a comparison of extraction fingerprints as moisturizes etc., solvents are most undesirable because of from Nereocystis luetkeana using HPLC and different extrac their irritating or drying effects on skin. The organic Solvent tion mediums. can usually be removed by evaporation but this is an addi 0025 Bottom: 5% algae extraction medium with butylene tional step with related economic and environmental costs. glycol 0019. Further there is a need to retrieve more complex 0026. Fourth: 5% algae extraction medium with DI water. targeted biomass extracts which can be obtained through (0027. Third: 5% algae extraction medium with 10 wt.% traditional aqueous, glycol or ethanol extractions and prefer Pluronic(R) L44 in water. ably accompanied by higher overall concentrations of the 0028 Second: 5% algae extraction medium with 10 wt.% targeted extractants. It is of special importance that highly Pluronic(R) F68 in water. active skin benefit agents are extracted from the biomass Such (0029 Top: 5% algae extraction medium with 10 wt.% as for example flavonoids and flavonoid derivatives. These Pluronic(R) F127 in water. actives have been shown to be particularly effective in pre 0030 FIG. 2 is picture of Fucus vesiculosus extraction venting radical damage on skin incurred from UV exposure medium with: and oxidation reactions. 0031 Left water extraction only. 0020 Even though certain skin active targets are known to 0032. Right water and 10 wt.% Pluronic(R) F127 extrac be secondary metabolites in numerous plants, algae and tion. fungi, prediction of the activity of the total extracts on skin, for example activity in protection against UV and radical SUMMARY OF THE INVENTION induced skin damage is much harder to predict. Changing the extraction medium may give rise to increased amounts of 0033. The Applicants have devised a solution to many of known protectants such as flavonoids but this change will also the above difficulties by extracting the biomass using aqueous be impacted by the increase or decrease in unknown co Solutions of nonionic Surfactants. The algae, fungi or botani extractants which in turn may alter the activity of the total cal biomasses are easily extracted gaining significant effi extractant on skin. Thus, the need for alternative extraction ciency benefits and overall improvements in the biologically methods which not only increase the extraction of skin actives active compounds extracted. but do not negatively impact the overall effect of the total 0034. Other non-trivial advantages are apparent from the extractants is desired. It would also be highly desirable if the improved process Such as colorand odor improvements of the total composition of the extracts e gives overall better perfor extractants. See FIG. 2. The avoidance of solvents such as mance in protection of skin from the adverse effects of known alcohols and glycols can be eliminated entirely in the present skinharming agents such as ultraviolet rays, especially UV-B process and the extractant medium presently employed is rays. In particular, it would be highly desirable to effectively even milder than those currently in use containing glycols partition the skin active target molecules without reliance on and/or ethanol. Gycols in particular are not popular with organic solvents and via an extraction method which achieves green and sensitive skin companies. higher concentrations of targeted molecules. It would also be 0035 Quite significantly the discovered method allows desirable for the partitioning matrix itself be suitable for for much faster filtration and a reduction in the number of cosmetic applications without further processing and for the filtrations necessary to remove the extracted biomass from the partitioning matrix to protect the target molecules from oxi aqueous extractant and Surfactant solution. This equates to dation and light degradation. huge manufacturing cost savings. 0021 For certain biomass materials, extraction processes 0036. Accordingly, the Applicants claim: can retrieve cell toxic components as well as skin beneficial 0037. A method of extraction of at least one target skin components as the partitioning occurs based on for example, bioactive from algae, fungi or botantical biomass, which solubility parameters. Thus typical extraction processes fre method comprises quently do not adequately distinguish between the two (ben a) contacting the algae, fungi or botanical biomass with an eficial vs. toxic). The present inventors have found that the aqueous liquid to form a slurry, present process using the particular nonionic Surfactants of 0.038 wherein the aqueous liquid comprises about 0.01 interest in many instances excludes the toxic extractants from to about 20, preferably 0.1 to about 10, and most pref the total extractant. erably about 0.5 to about 5 wt. percent, especially 0.5 to 0022. Further, it is also highly desirable that the extraction about 2 or about 3 wt.% of a nonionic surfactant selected process retrieves relatively low color extractants but still from the group consisting of block copolymers of poly retrieves the important target molecules and that the total (ethylene oxide)/poly(propyleneoxide) and alkyl poly extracted materials have high beneficial activity on skin. glucosides, and the wt. percent is based on the total 0023. Additionally, the extraction process for biomass can weight of the slurry, be quite time consuming especially in relation to the filtering and step (removal of the biomass). For example, aqueous extract b) optionally, separating the biomass from the aqueous slurry, of an algae biomass may take as long as three days and use wherein the target skin bioactive is a flavonoid or flavonoid multiple filters to remove the solid biomass from the extract derivative. US 2015/O 140141 A1 May 21, 2015

0039. Use of a nonionic surfactant in an aqueous medium tions in the case of algae, it may be preferred to use cultivated to increase flux during a filtration process of a solid biomass algae, since cultivation reduces the risk that Supplies will from an aqueous extract, become limited in the case of algae as aquaculture expands wherein the nonionic Surfactant is a surfactant selected from and marine environmental conditions change. the group consisting of block copolymers of poly(ethylene 0049. The plant, algae or fungi source may be pre-treated oxide)/poly(propyleneoxide) and alkyl polyglucosides and in a fermentation process to further breakdown the plant, the aqueous extract comprises at least a flavonoid or flavonoid algae or fungi biomass pulp possibly making any bioactives derivative. present in the biomass more readily available for extraction. 0040. The solid biomass is selected from algae, fungi or 0050 For example, Nereocystis is genus of edible sea kelp botanical biomass, preferably flavonoid rich biomass. that forms thick beds of up to 74 meter plants on rocks in what 0041 Use of a nonionic Surfactant in an aqueous medium are known as kelp forests. This sea kelp may be fermented to increase the flavonoid extraction with Lactobacillus, the same bacterium that produces yogurt. from a flavonoid rich plant, wherein the nonionic Surfactant is Fermentation breaks down the cellular tissue of the kelp leaf, a Surfactant selected from the group consisting of block thereby increasing the bioavailability of the naturally occur copolymers of poly(ethylene oxide)/poly(propyleneoxide) ring phytonutrients that are abundant in kelp. and alkyl polyglucosides. 0051 Fermentation and subsequent reduction of the kelp extract may result in the concentration of these vital nutrients DETAILED DESCRIPTION OF THE INVENTION for use in topical formulations. In skincare products it acts as 0042 All percentages and ratios used herein are by weight excellent oil-free moisturizer. of the total composition unless otherwise designated, and all 0.052 The term “biomass” as used herein means a pulp or temperatures are in degrees Celsius unless otherwise desig puree derived from the algae, plant or fungi. Preferably the nated. term biomass refers to an algae or plant. The pulp or puree 0043. The term "safe and effective amount” as used herein may be derived from the entire plant, algae or fungi or from a means an amount of a compound or composition Sufficient to part of the plant (e.g., leaf, stem, root, flower, seed, sap, bark, induce a positive benefit as described herein, but low enough etc.). to avoid serious side effects in the judgment of the skilled 0053. The marine algae may for example be preferably artisan. selected from the group consisting of Chondrus Crispus, 0044) The term “slurry” as used herein means a suspen Nereocystic luetkeana and Sarrcodiotheca gaudichaudii, Sion of plant, algae or fungi matter in Water. Fucus vesiculosus, Sarcodiotheca gaudichaudii, Ulva lac 0045. The term “molecular weight’ as used herein refers tuca, Laminaria longicruris, Nannochloropsis oculata, Tet to weight average molecular weight unless otherwise speci raselmis suecica fied. 0054 The hydrophobic extracts from algae are especially 0046. The term “comprising for purposes of the invention interesting because the extracts are known to moisturize skin, is open ended, that is may include other components. have firming and anti-irritant properties which make the 0047 Plant, algae or fungi for purposes or this disclosure extracts highly suitable for aging skin. The algae extracts means any plant, algae or fungi, especially flavonoid rich contain polysaccharide Sugars such as alginates, fucoidanes, plant, algae or funge. For example the plant, algae or fungi, polyphenols and fucosterol. Alginates are compounds preferably flavonoid rich plant, algae or fungi may be selected responsible for moisture retention and elasiticity of the skin. for example from the group of genus species consisting of Fucoidanes are sulfated polysaccharides that encourage cir Acacia Senegal, Achillea millefolium, Aloe barbadensis, Ana culation and polyphenols have antiseptic, anti-inflammatory nus sativus, Argania spinosa, Avena sativa, Cocos nucifera, and anti-oxidant properties. Fucosterol functions as a emol Bupleurum falcatum, Butyrospermum parkii, Calluna vul lient, moisturizer and blood stimulant garis, Camelia sinensis, Cassia elate, Cocoa Callus, Chon drus crispus, Centella asiatica, Ceratonia siliqua, Cestrum 0055. The term “extract for purposes of this application latifolium, Cinnamomum cassia, Citrus limon, Coffee Ara means any skin active which has been extracted from the bica, Cola acuminate, Cucumis sativus, Durio zibethinus, plant, algae or fungi biomass. In the present case, the extract Fucus vesiculosus, Glycine soja (Soybean), Glycyrrhiza gla is present in the extracting water/surfactant mixture. It is this bra, Gymnema Sylvestre, Haslea Ostrearia, Heliantus mixture which is directly added to the cosmetic, topical or annuus, Hibiscus abelmoschus, Humulus lupulus, Laminaria pharmaceutical product compositions. Indeed this is one of digitate, Lepidium meyenii, Linum usitatissimum, Macad the advantages of the extracting method. The presence of the amia termifolia, Melva Sylvestris, Melissa officinalis, Morus surfactant, in particular the Pluronic R) does not need to be alba, Morus bombycis, Nereocystis luetkeana, Olea euro removed. It’s presence in the final cosmetic, topical or phar paea, Orthosiphon stamineus, Palmeria palmate, Peu maceutical composition is desirable. cedanum graveolens, Peumus boldus, Pisum sativum, Puer 0056. The extract will be present in the aqueous surfactant aria lobate, Punicia granatum, Pyrus malus, Rheum mixture liquid phase after extraction from the biomass. palmatum, Rhodiola crenulata, Rosmarinus officinalis, Saxi 0057 Extraction for purposes of this application means fraga sarmentosa, Sarrcodiotheca gaudichaudii, Scutellaria treatment or exposure of the biomass (pulp or puree) with a baicalensis, Serenoa serrulata, Spirulina platensis, Theo liquid. Target bioactive moiety or moieties (at least one skin broma cacao, Tuber magnatum, Uncaria tomentosa, Vitis active) are retrieved from the solid biomass via solubilization vinifera, Ptychopetalum Olacoides, Zea mays and Zingiber in the liquid phase. officinale. 0.058 As explained previously the plant, algae or fungi is 0048. Any of the plants, algae or fungi used in the present flavonoid rich. Extraction according to the presently dis disclosure may be natural occurring, cultivated or genetically closed methods of the flavonoid rich plant, algae or fungi will modified organisms (GMO). For industrial cosmetic applica retrieve “target skin actives’. US 2015/O 140141 A1 May 21, 2015

0059. The term “target skin actives” to be extracted catechen, epigallo catechin 3-gallate, eriocitrin, eriodictyol. includes compounds containing the flavone backbone (2-phe farrerol, fisetinidol, fisetinidol-4-ol, fustin, garbanzol, glab nyl-1,4-benzopyrone), isoflavone and the neoflavonoids ranin, glepidotin B. glycyphyllin, hesperetin, hesperidin, backbones or derivatives thereof. homoeriodictyol. 7-hydroxyflavan, isochamaejasmin, isos 0060. The flavone backbone is: akuranetin, isouriaretin, kazinola, kolaflavanone, liquiretige nin, manniflavanone, 6, methocyaromadendrin 3-O-acetate, 6-methoxytaxifolin, 2'-O-methylodoratol, maringenin, narin (A) gin, narirutin, neoastilbin, neoeriocitrin, neohesperidin, odo ratol, phloretin, phellamurin, phloretin, phloridzin, pinobanksin, pinocembrin, pinocembrin 7-rhamnosyl-gluco O side, piperaduncin B, poncirin, 5'-prenyl, naringenin, prun ing, Sakuranetin, Sanggenon C. Sanggenon D. Silandrin, sily bin, sillychristin, Sophoranone, strobopinin, taxifolen, taxifolin-3-O-acetate, tephrowatsin, theasinensin A, 2',4',6'- trihydroxyl-3'-formyldihydrochalcone and uvaretin. O 0066. A more preferred list would include the flavonoids and flavonoid derivatives selected from the group consisting 0061. The isoflavan core is of naringin (aurantiin, naringenin 7-rhamnoglucoside), C-glucosylrutin, C-glucosylmyricetin, C-glucosylisoquerce tin, C-glucosylquercetin, dihydroquercetin (taxifolin), hespe (B) ridin (3',5,7-trihydroxy-4-methoxyflavanone 7-rhamnoglu O coside, hesperitin 7-O-rhamnoglucoside), neohesperidin, rutin (3.3',4',5,7-pentahydroxyflavone 3-rhamnoglucoside, quercetin 3-rhamnoglucoside), troXerutin (3,5-dihydroxy-3', 4,7-tris(2-hydroxyethoxy)flavone-3-(6-O-(6-deoxy-C-L- mannopyranosyl)f-D-glucopyranoside)), monoxerutin (3.3', 4,5-tetrahydroxy-7-(2-hydroxyethoxy)flavone-3-(6-O-(6- deoxy-O-L-mannopyranosyl)f-D-glucopyranoside)), diosmin (3',4',7-trihydroxy-5-methoxyflavanone 7-rhamno 0062. The neoflavonoid core is glucoside), eriodictin, and apigenin 7-glucoside (4.5,7-trihy droxyflavone 7-glucoside), kaempferol, quercitrin, avicu larine, myricitin, epicatechins and catechins. (C) O Extraction Method 0067. As explained above the puree or pulp biomass is added to a water based medium to form a slurry. 0068. The slurry will normally comprise primarily water, that is, comprise for example over 50 wt.%, more typically over 75 wt.%, most typically over 85 wt.% water but may 0063. These above cores will normally be substituted by further contain organic solvents. hydroxyl groups at various positions on the aromatic rings. In 0069. The organic solvents may be hydrocarbons, fatty Some cases such as myricitrin the oxygen containing ring is acid esters, ethers, alcohols, fatty acids or ketones. However, Substituted by a Sugar moiety. Accordingly the flavonoid or if organic solvents are used alcohols or polyalcohols are pre flavonoid derivative (the target skin actives) are selected from ferred and may be selected from the group consisting of compounds which contain cores represented by (A), (B) and methanol, ethanol. 1-propanol, 2-propanol. 1-butanol. 2-bu (C), the cores may be further substituted. tanol, isobutyl alcohol, tert-butyl alcohol, 1.2-ethanediol, 0064. In terms of this disclosure what is meant by fla 1.2-propanediol. 1,3-propandiol, butylene glycol and glyc vonoid-rich would preferably include plant, algae or fungi erin. Preferably, no organic solvent is present in the extraction extract which contains flavonoids aglycones and or glyco slurry. sides of flavones, of flavanones, of 3-hydroxyflavones (fla 0070 Thus the slurry of step a) may comprise an organic Vonoles), of aurones, and of isoflavones. Also preferred are solvent from about 1 to about 10 wt. percent of the slurry. biflavonoids constructed from two flavonoid units, for 0071. But the slurry is preferably essentially organic sol example, those occurringinginkgo species. Further preferred vent free. By essentially organic solvent free, it is meant that flavonoids are the chalcones, especially phloricin, hesperidin the slurry contains minor amounts of organic solvent, that is methyl chalcone, and neohesperidin dihydrochalcone. about 0.1 to about 5 wt. percent, or 0.1 to about or less than 1 0065 Accordingly a preferred listing of flavonoids would wt. percent organic solvent. include abyssinone I, abyssinone V. afzelechin, ampelopsin, (0072. The slurry will contain about 0.01 to about 20, pref aromadendrin, asebogenin, auriculoside, betagarin, broussin, erably 0.1 to about 10, and most preferably about 0.5 to about broussonin C, butin, butrin, (+)-catechin, catechin 7-O-B- 5 wt.%, especially 0.5 to about 2 or about 3 wt.% of a xyloside, davidigenin, diffutin, 7.4'-dihydroxylflavan, 2,6-di nonionic Surfactant, preferably the nonionic Surfactant is a hydroxyl-4'-methoxydihydro-chalcone, 7.3'-dihydroxyl-4- copolymer, preferably a block copolymer of poly(ethylene methoxy-8-methylflavan, 7.4'-dihydroxyl-8-methylfalvan, oxide) and poly(propylene oxide), or a alkyl polyglucoside 6,8-diprenylmaringenin, dracorubin, (-)-epicatechin, ent-epi and more preferably the nonionic surfactant is a triblock US 2015/O 140141 A1 May 21, 2015

copolymer of poly(ethylene oxide) and poly(propylene Surface-active agents are: the long chain alkanolamides; the oxide) or an alkyl polyglucoside. polyethylene oxide condensates of alkyl phenols; the conden 0073. The weight percent of the nonionic surfactant is sation product of aliphatic alcohols having from about 8 to based on the total weight of the slurry. about 18 carbon atoms, in either straight chain, block or 0074 The term “hydrophobic' as used herein meant a branched chain configuration, with ethylene oxide; the long component of the natural product (biomass) which is more chain tertiary amine oxides; the long chain tertiary phosphine soluble in a nonpolar solvent than in water. oxides; the long chain dialkyl Sulfoxides containing one short 0075 Since many bioreactive or target molecules of the chain alkyl or hydroxyalkyl radical of from about 1 to about biomass are located within the structure of the cell wall or 3 carbon atoms; and the alkyl polysaccharide (APS) surfac other organelles within the cell, a suitable process is required tants such as the alkyl polyglycosides; the polyethylene gly to extract the desired components from the cell. Accordingly, col (PEG) glyceryl fatty esters and copolymers of ethylene the cell wall barrier must be perturbed or ruptured sufficiently oxide and propylene oxide including block copolymers of to allow diffusion to occur into the extraction liquid. A polyethylene oxide and polypropylene oxide. The preferred method is therefore needed to rupture cell walls and mem non-ionic Surfactants are the condensation product of ali branes to maximize the removal of the active. Examples of phatic alcohols having from about 8 to about 18 carbonatoms, Such process conditions include the use of heat, high Sear in either straight chain, block or branched chain configura mixing, ultrasonic waved, microwaves, high pressure and tion, with ethylene oxide. For example, copolymers of ethyl prolonged exposure to the extractant medium. ene oxide and propylene oxide are preferred. 0076. Thus the biomass is generally in the form of a pulp I0084. Of special interest however are the block copoly or puree which has been mashed or broken up to rupture cell mers of polyethylene oxide and polypropylene oxide. These walls and membranes. block copolymers are often referred to as poloxamers. These 0077. The amount of pulp or puree biomass which is poloxamer Surfactants are polymeric and comprise blocks of added to the extractant medium (water and nonionic Surfac alternating hydrophobic and hydrophilic blocks. The hydro tant) to form a slurry will vary from about 1 to about 50 wt.%. phobic blocks comprise polypropylene oxide while the preferably about 2 to about 25 wt.% and most preferably hydrophilic blocks comprise polyethylene oxide blocks. about 3 to about 15 wt.% of the total weight of the slurry. I0085. The poloxamers of interest in this application are 0078. The pulp or puree biomass wt.% is normally a dry diblock or triblock, preferably triblock poloxamers of the weight. For example, the pulp or puree is normally dried structures below and are known under the tradename Plu before extraction and most or all of the water content is ronic R supplied by BASF Corporation. removed. The weight percent of the dried biomass varies from about 1 to about 50 wt.% of the total weight of the slurry. HO(CHO)(CHO) (C2HO)OH (I) 007.9 Therefore, the dried biomass contains, if any, only O small amounts of water, for example 0.01 to 5 wt.%, prefer ably 0.01 to about 2 wt.% water. HO(CHO)(CHO) (CHO),OH (II) wherein a and c are independently 3 to 200, Non-Ionic Surfactants and b and d are independently is 5 to 100. 0080. By “surfactant, it is meant any of those molecules I0086 For example, some typical triblock polymers which that are commonly known in the art to provide a reduction in are envisioned in the present application are: Surface tension (such as being able to reduce the Surface tension of water to 60 dynes/cm or less, and, more preferably 50 dynes/cm or less when added to pure deionized water, and Pluronic (R) Molecular Weight measured at ambient temperature i.e., 20°C.). Furthermore, it L10 3200 is preferred that the surfactant or surfactants have a water L31 1100 solubility of at least about 1% in deionized water at ambient L35 1900 L38 47OO temperature. As such, the term Surfactant can also include L42 1630 those molecules that are also commonly referred to as oil in L43 1850 water emulsifiers. In one embodiment, the non-ionic Surfac L44 2200 tant has a Hydrophile-Lipophile Balance (HLB) that is from L61 2OOO L62 2SOO about 8 to >24, and more preferably from about 10 to about L63 26SO >24. L64 2900 0081. By “non-ionic surfactant, it is meant a surfactant P65 3400 that does notionize in aqueous media. In a preferred embodi F68 8400 L72 2750 ment, the non-ionic Surfactant is liquid at ambient tempera P75 41SO ture. F77 6600 0082. The function of the surfactant is to provide one or L81 2750 more of the following: emulsification or solubilization of P84 4200 P85 4600 hydrophobic compounds, wetting and Surface tension reduc F87 7700 tion. F88 114OO 0083. Non-ionic surfactants, which can be used in the L92 3650 presently disclosed extraction process, include those broadly F98 13OOO L101 3800 defined as compounds produced by the condensation of alky P104 S900 lene oxide groups (hydrophilic in nature) with an organic P105 6SOO hydrophobic compound, which may be aliphatic or alkyl F108 146OO aromatic in nature. Examples of preferred classes of nonionic US 2015/O 140141 A1 May 21, 2015

-continued upon the molecular weight and the weight ratio of the hydro phobic (PP) and hydrophilic blocks (PE). Pluronic (R) Molecular Weight 0093. The inventors have discovered that a range of tri L121 4400 block copolymers of differing molecular weights and PP and L122 SOOO PE ratios function when dissolved in aqueous solution are P123 5750 highly effective solubilizers for the target molecules from F127 12600 various plant, fungi and algae sources. RPE 1050 1950 RPE1720 21 SO 0094. These particular block nonionic surfactants are RPE 1740 26SO known to form micelles in water. Thus they may function as RPE 2520 31 OO solubilizing agents for target molecules. RPE 2S4O 3600 0.095 Other non-ionic surfactants of particular interest are the alkyl polyglucoside. I0087 Particularly preferred Pluronics(R) are Pluronic L35, 0096 Alkyl polyglucosides (APGs) are well known in the L44, L43, P105, F68, F87, F108, RPE 1050, RPE 1720, RPR art and may be purchased under the tradename PlantarenR) 1740 and F127 (NF Grades-BASF maintains a Drug Master from BASF SE. File for some of these products). 0097. The terms alkyl polyglucoside and alkyl glucoside are interchangeable. *HO(CHO)(CHO)(C2HO)OH (I) 0098. An alkyl polyglycoside is formed from the reaction **HO(CHO), (CHO) (CHO),OH (II) of glucose and fatty alcohol. An alkyl polyglycoside com pound has a hydrophobic portion (carbon chain) and a hydro philic portion (glycoside unit or group). When describing an alkyl polyglycoside, the average degree of polymerization Pluronic (R) Poloxamer a and c' band d’ Mw HLB (DP) is mentioned. For example, in an alkyl polglycoside or L35: 101 11 16 1900 19 alkyl glycoside a compound with a DP of about 1.4, there are, L43: 123 7 21 1850 7-12 on average, 1.4 units of glucose for eachalkyl group. An alkyl L44 * 124 12 2O 2090-2360 12-18 F68: 188 75 30 7680-951 O >24 polyglucoside or alkyl glucoside is normally a mixture of F87: 237 62 39 6840-883O >24 varying amounts of glucose units on the molecule. It is to be F108: 338 128 S4 12700-17400 >24 understood that a DP of 1.4 does not mean that each molecule P105* 335 38 S4 6SOO 12-18 has 1.4 glucose units. F1278 407 98 58 9840-14600 18-23 RPE 1050** NA 22 8 --1950 15 0099 Alkyl polyglucosides may be represented by the RPE 1720** NA 10 15 --2150 6 following general formula: R-O-(RO), (Z), wherein RPE 1740** NA 24 15 -2650 12 R is a monovalent organic radical having from about 6 to Note: about 30 carbon atoms, R is a divalent alkylene radical hav ** and * designate whether formula (I) or (II) of the non-ionic surfactant, ing from 2 to 4 carbon atoms, and Z is a saccharide residue The number given in the table represents the number of repeating units in a and the number having 5 or 6 carbon atoms, b is a number from 0 to about 12, gfrepeating units in b. Accordingly for F108 of structure (I), a is 141 and c is 141. 'The number given in the table represents the number of repeating units of b and d. and a is a number of from 1 to 6. Accordingly for RPE 1050 of structure (II), a is 22 and b is 8 and d is 8. 0100 Additional suitable alkyl polyglucosides include, Mw represents weight average molecular weight, but are not limited to GLUCOPONR) 225DK, in which the 0088. The first step in synthesizing these Pluronic R. Sur alkyl group contains 8 to 10 carbonatoms and has an average factants is the creation of a hydrophobe of desired molecular DP of 1.7: GLUCOPONR 625UP in which the alkyl group weight by the controlled addition of propylene oxide to the has 12 to 16 carbon atoms and has an average DP of 1.6: two hydroxyl groups of propylene glycol. Ethylene oxide is APG(R) 325N, in which the alkyl group has 9 to 11 carbon then added to sandwich this hydrophobe between hydrophilic atoms and has an average DP of 1.5: GLUCOPONR 600UP. groups, controlled by length to constitute from 10% to 80% in which the alkyl group has 12 to 16 carbon atoms and has an (by weight) of the final molecule. average DP of 1.4: PLANTAREN 2000R, in which the alkyl I0089. In the RPE (or reverse Pluronic(R) surfactants) the group has 8 to 16 carbon atoms and has an average DP of 1.5; structure is as in the formula II above. Thus the buildup of the and PLANTAREN 1300R, in which the alkyl group has 12 to block copolymer is reversed. The central block is polyethyl 16 carbon atoms and an average DP of 1.6. ene oxide sandwiched between two polypropylene blocks. 0101 The alkyl polyglucosides is typically formed by 0090. A range of PluronicR) surfactants are available reacting a Sugar with a higher alcohol in the presence of an where the hydrophobe or center block (polypropylene oxide) acid catalyst, or by reacting a Sugar with a lower alcohol (for varies from about 900 to 4000 weight average molecular example, methanol, ethanol, propanol, butanol) to thereby weight and the ethylene oxide blocks make up from 10 to 80, provide a lower alkyl glycoside, which is then reacted with a preferably 30 to 95, most preferably 40 to 90 weight percent higher alcohol. The higher alcohol generally has the formu of the total block copolymer. lation RO(RO), H, wherein R represents a straight or 0091. The reverse Pluronics(R) RPE surfactants are avail branched alkyl or alkenyl group having from 8 to 22 carbon able where the center block (polyethylene glycol) weight atoms, R represents an alkylene group having from 2 to 20 average molecular weight varies from about 300 to about carbon atoms, and is a mean value that is 0 to 10. 1000 average molecular mass and the total weight average 0102 Specific non-limiting examples of the higher alco molecular weight for the polypropylene oxide terminal hol are straight or branched alkanol such as hexanol, hep blocks range from about 1000 to about 3800. tanol, octanol, nonanol, decanol, dodecanol, tridecanol, tet 0092. Accordingly the triblock polymers typically range radecanol, pentadecanol, hexadecanol, heptadecanol, from about 1000 to about 16000 average molecular weight. octadecanol, methylpentanol, methylhexanol, methylhep The triblock polymers are liquid, Solid or paste depending tanol, methyloctanol, methyldecanol, methylundecanol, US 2015/O 140141 A1 May 21, 2015 methyltridecanol, methylheptadecanol, ethylhexanol, ethy 0108. Another typical way of removing the extracted bio loctanol, ethyldecanol, ethyldodecanol, 2-heptanol, mass is to centrifuge then filter the Supernatant. 2-nonanol, 2-undecanol, 2-tridecanol, 2-pentadecanol, 0109 These consecutive filtrations are very time consum 2-heptadecanol, 2-butyloctanol, 2-hexyloctanol, 2-octyloc ing. The filtration becomes progressively slower as the pore tanol, 2-hexyldecanol and/or 2-octyldecanol; an alkenol Such size decreases. as hexenol, heptenol, octenol, nonenol, decenol, undecenol, 0110. While the speed of filtration is to a certain extent dodecenol, tridecenol, tetradecenol, pentadecenol, hexade biomass determined, if the extractant medium is water/Plu cenol, heptadecenol and octadecenol. These alcohols may be ronic or an alkyl glucoside, it has been discovered that some used either alone or a mixture of two or more of them. of the intermediate filtrations can be eliminated. For example, 0103 Preferred alkyl glucosides comprise from about 1 to one can move from a 2.5 micron filtration directly to a 0.45 about 6 glucose residues per molecule, preferably 1 to 4. filtration without going through an intermediate say 8.0 Preferred alkyl polyglucoside are decyl glucoside, caprylyl/ micron filtration. Of course, the elimination of extra filtration caprylglucoside, coco glucoside and lauryl glucoside which steps is highly desirable and one of the unexpected advan are the condensation product of the corresponding alcohol tages of the present process. with a glucose polymer or single glucose residue and is avail 0111. Thus it has surprisingly been found that when the able commercially from BASF Corporation of Florham Park, extractant medium is water/non-ionic Surfactant or preferably N.J. under the trade name, PlantarenR). water/PluronicR) or alkyl glucoside, the filtration process is 0104. The cosmetic compositions presently disclosed may significantly accelerated. further comprise various additives utilized in the cosmetic field. The CTFA Cosmetic Ingredient Handbook and Per 0112 For example, when the inventive extractant medium Sonal Care Product Counsels ingredient buyers guide is used, the filtering process is normally 2 or 3 time faster than describe a wide variety of nonlimiting cosmetic ingredients an extractant medium comprising water only. commonly used by those skilled in the art and which are 0113. Accordingly the present method may embody the Suitable for use in the cosmetic compositions of the present step of separating the plant, algae or fungi biomass from the invention. Examples of these ingredient classes included: aqueous liquid copolymer slurry by filtration and the filtration abrasives, emulsifiers, absorbents, gelling agents, antifoam is carried out using a filter having a pore size ranging from ing agents, buffering agents, colorants, film formers, pH about 0.1 to about 0.5 microns, preferably about 0.1 to about adjusters, humectants, thickeners and pigments. It is further 0.4, most preferably about 0.1 to about 0.3 microns and the recognized that additional cosmetic active ingredients. Such speed of filtration is at least twice as fast as separation of the as anti-acne actives (for example, salicylic acid or benzoyl plant, algae or fungi biomass from the same water or water/ peroxide), anti-wrinkle actives (for example, retinoids or organic solvent slurry. beta-hydroxy acids), antioxidants (for example, ascorbic acid and its derivatives or tea extracts), chelators (for example, Use of the Extractant furildioxime), anti-inflammatory agents (for example, corti 0114. The present extracts are particularly suitable for costeroids), slimming agents (for example, caffeine), skin body care products, in particular for use in skin-care products, lightening agents (for example, mulberry extract or kojic as bath and shower products, preparations containing fra acid), or Sunscreens (for example, those commercially avail grances and odoriferous Substances (perfumes, after-shave able under the name PARSOL), may be utilized in the cos lotions), hair-care products, deodorizing and antiperspirant metic compositions of the present invention based on the preparations, decorative preparations, light protection formu desired overall benefits intended to be conferred by the com lations (Sunscreens) and skin preparations containing active position. ingredients (vitamins, hormones or antimicrobials). 0105. The upper and lower limits for the quantity of the 0115 The extract is intended primarily for topical appli extract according to the present invention in any given for cation to human skin or hair. The composition according to mulation for a cosmetic composition is based both on the the invention is particularly useful as an agent for condition desired effect of the cosmetic compositions, the other com ing and Smoothing the skin or hair, and preventing or reducing ponents of the formulation, the type of composition, cost and the appearance of wrinkled or aged skin and can thus be practicality. However, the plant, algae or fungi extract pref formulated into a topical skin treatment formulation for use in erably is included in a quantity between about 0.01% and cosmetic applications. The topical skin treatment formulation about 5% and more preferably between about 1% and 3% of the invention is thus useful in the removal of oxidants from based on the final weight of the composition. For purposes of the skin and in the dermatological treatment of the skin this application, this wt.% includes the extract, Surfactant and including, but not limited to, skin imperfections, dry skin, water mixture. photodamaged skin, wrinkles, age spots, acne, skin lighten ing, psoriasis, and atopic dermatosis. Filtering of the Fungi, Algae or Biomass 0116 Suitable skin-care products are, in particular, body 0106 Extracting with aqueous solutions of Pluronic R is oils, body lotions, body gels, treatment creams, skin protec faster and offers higher yields of extractant. tion ointments, shaving preparations, such as shaving foams 0107. In order to remove the biomass, algae or fungi from or gels, skin powders, such as baby powder, moisturizing the slurry it is often necessary to filter using increasingly gels, moisturizing sprays, revitalizing body sprays, cellulite Smaller pore filters. For example, it is typical to require mul gels and peeling preparations. tiple filtrations starting from a large pore size of about 150 0117 Preparations containing fragrances and odoriferous micron moving to progressively smaller pore sizes. For Substances are in particular scents, perfumes, toilet waters example, five filtrations may be necessary starting with 150 and shaving lotions (aftershave preparations). micron, followed by 11 micron, to 2.5 micron and finishing 0118 Suitable hair-care products are, for example, sham with 0.45 and 0.22 micron filters. poos for humans and animals, in particular dogs, hair condi US 2015/O 140141 A1 May 21, 2015

tioners, products for styling and treatinghair, perming agents, TABLE 2 hair sprays and lacquers, hair gels, hair fixatives and hair dyeing or bleaching agents. Extraction Slurry Compositions for F. vesiculosus 0119 Suitable decorative preparations for skin are for Pluronic (R) Time to Filter? example lipsticks, nail varnishes, eye shadows, mascaras, dry DIWater F127 % Algae %Yield (hrs) and moist make-up, rouge, powders, depilatory agents and 95 5 30% 6 Suntan lotions. 85 10.00 5 SO% 1 The % yield is a measure of the weight percent of the filtered extract collected after 0120 Suitable cosmetic formulations containing active filtration. A higher yield would indicate less extract is lost during filtration, 'The water only extracting fluid slurry was filtered in sequence with consecutive filters used ingredients are in particular hormone preparations, vitamin (pore size inum) = 150, 11, 2.5 and 0.8. The series of water only filtrations took 6 hours in preparations, vegetable extract preparations and antibacterial total. preparations. 0127. The water/Pluronic extracting fluid slurry was 0121 The present body care products can be in the form of filtered in sequence with consecutive filters of pore sizes creams, ointments, pastes, foams, gels, lotions, powders, in microns 150, 11, 2.5, 0.45 and 0.22. The inventive make-ups, sprays, Sticks or aerosols. The present extractants extractions took a total of 2 hours. See FIG. 2 showing may be present in the oil phase or in the aqueous or aqueous/ the difference in color of the extracting fluid. alcoholic phase. I0128 Clearly incorporation of the Pluronic R) within the 0122) The following examples further describe and illus aqueous media gave an improved extraction and filtering trate the present invention and should not be construed as efficiency when compared with the water only. Extracting limitations of the present invention. with aqueous solutions of PluronicR) is faster, of higher yield (almost double the yield at /3 the time). EXAMPLES Analytical Results: Example 1 I0129 FIG. 1 is a comparison of extraction fingerprints from Nereocystis luetkeana using HPLC and different extrac tion mediums. Genus Species: Nereocystis luetkeana 0130 Pluronic extracts contained the same compounds as the 100% aqueous and butylene glycol extraction medium 0123) Nereocystis Luetkaeana was provided by BC Kelp. plus additional components. The N. luetkeana is a dried, crushed pulp of all parts of the 0131 FIG. 2 indicates that the color of extractant in the algae organism dried crushed material water/surfactant solution is of much better color when com 0.124. The above dried algae was added to various extrac pared to the algae extracted with only water tant mediums at the amounts given below in Table 1. 0.132. The extracts are thought to have antioxidant, anti inflammatory, anti-melanogenic properties and perhaps col TABLE 1. lagen boosting properties. It is also believed that the Surfac Extraction Slurry Compositions for N. Luetkaeana tant-extract water mixtures are by themselves more oxidation resistant. Pluronic (R) Pluronic (R) Pluronic (R) (0.133 Table 3-7 Extractant Slurries for Additional Species DIWater BG L44 F68 F127 Wt.% Algae Aqueous extraction as above is carried out for a number of 95.00 S.OO different plant species. The aqueous medium extractant only 95.00 S.OO is compared to the extractant via aqueous medium containing 85.OO 1O.OO S.OO 85.OO 1O.OO S.OO varying amounts of non-ionic Surfactants. 85.OO 1O.OO S.OO 0.134 Dried, cut Cassia alata or Argania spinosa leaves were mixed with hot water (80°C.) or with the hot aqueous Notes: numbers in % are wiw basis. Pluronics dissolved in water prior to addition of algae. BG medium containing the non-ionic Surfactants at a ratio of 1:9 refers to butylene glycol. (100 gleaves:0.9L water), the pH of the mixture was adjusted to pH-6 and extraction was proceeded during 1 hour at 80° 0.125. The above slurries are heated to 60° C. and mixed C., pH6 undershaking. After cooling to room temperature the with high speed stirring for 1 hour. The slurry is cooled to insolubles were removed by centrifugation and the Superna room temperature and is filtered via 11 micron filter. Samples tant filtered. The concentration of the targeted flavonoids in are filtered a second time through a 0.22 micron filter before each of the liquid extracts was measured (mg/100g of liquid analysis. extract). The total amount of dry matter recovered in each extract was measured (g/100g of liquid extract). The amount Example 2 ofactive matter is calculated as the difference between the dry matter of the plant extract with surfactant medium and the dry matter of the Surfactant solution alone. Species: Fucus vesiculosus Quantification of Flavonoids 0126 A water only and water/Pluronic containing slurries were mixed overnight then filtered with a consecutively 0.135 Flavonoid determination in the liquid extracts were smaller pore size filters starting at 150 micron, 11 micron, 2.5 performed by HPLC analysis, the method depending of the micron, 0.45, 0.22 flavonoids contained in the plant. US 2015/O 140141 A1 May 21, 2015

0136. For Cassia alata leaves extracts, the column used 1) “Chemical Tests in Tubo was a C18 reversed phase column: Symmetryshield(R) RP 18 WATERS 5um (4.6x250 mm) maintained at 30° C. Gradient a) AO Antioxidant DPPH Test (AO-DPPH) elution of the samples and standard were performed using water (eluent A) and acetonitrile (eluent B). The gradient (0.148. DPPH (diphenylpicryl hydrazyl) is a free, stable, elution initial conditions were 20% of eluent B with linear violet-coloured radical which, in its leuco derivative, is modi gradient to 60% from 0 to 35min, followed by linear gradient fied by Substances which capture free radicals (neutralising to 20% of eluent B at 37 min. effect, also described as a “scavenger effect”). 0.137 The flow rate was 1 ml/min and the sample injection 0149. The result is given as percent inhibition of DPPH' in volume was 10 ul: 2 injections were performed for each radical form relative to the control material without extract. sample b) Anti-HO' Test with Salicylic Acid (Fenton Reaction) 0.138. Detection was performed with a Photo Diode Array 0150. The HO' (formed by H.O. with Fesup.++ and Detector at 350 nm. EDTA present) hydroxylate the salicylic acid, which then 0139 Calibration curves were realized with a Kaempferol 3-O-sophoroside and Kaempferol standards injected at dif forms a reddish compound. ferent concentrations. 0151. The optical density at 490 nm corresponds to the hydroxylated Salicylic acid content. Biological Testing I0152. An anti-radical substance reacts with the HO' radi 0140 Antiinflammatory Properties. In Vitro-UVB Light cals and reduces the formation of this red compound. Protection (UVB-LDH and UVB-PGE2) 0153. The results are given as percent inhibition of the 0141 Cell Protection Effect Against UVB on In Vitro hydroxylation content (average of 2 tests). Cultivated Human Keratinocytes 0154) Thiobarbituric Acid Reactive Assay (% 0142 Background: UVB rays (from 280 to 320 nm) trig ger inflammation (erythema, odema) by activating an AO-TBARS) enzyme, namely phospholipase A2 or PLA2, which removes 0.155. An In vitro model to test relative antioxidant poten arachidonic acid from the phospholipids of the plasma mem tial: ultraviolet-induced lipid peroxydation in liposomes, brane. Arachidonic acid is the precursor of prostaglandins, Archives of biochemistry and biophysics, Vol. 283, No. 2, which cause inflammation and cell membrane damage; the 234-240, (1990). prostaglandins E2 (PGE2) are formed by cyclooxygenase. 0156 An approch towards understanding the genesis of This membrane stress is indicated by the release of the cyto Sunlight-induced skin cancer, Indian Journal of Biochemistry plasm enzyme lactate dehydrogenase (LDH). The effect of and Biophysics, Vol. 27, 254-263, (1990). UVB radiation was investigated on keratinocytes in vitro by determining the release of the cytoplasm enzyme LDH (lac ABBREVIATIONS tate dehydrogenase). This enzyme serves as a marker for cell damage. APG-1 is PlantacareR 2000 UP or Decyl Glucoside (INCI) 0143 Method: To carry out the tests, a defined medium (DMEM), which comprises 10% fetal calf serum, was inocu APG-2 is Plantacare R 810 UP or Caprylyl/Capryl Glucoside lated with the keratinocytes and the plant extract (diluted with (INCI) saline solution) was added 72 hours after inoculation. 0144. The keratinocytes were then irradiated with a UVB L35 is Pluronic(R) L35 or Poloxamer 101 (USAN) dose (30 m.J/cm-tubes: DUKE GL40E). (0145. Following further incubation for 1 day at 37° C. and L43 is Pluronic(R) L43 or Poloxamer 123 (USAN) at 5% CO, the LDH and the PGE2 content in the supernatant was determined. The content of LDH (lactate dehydrogenase) L44 is Pluronic(R) L44 or Poloxamer 124 (USAN) was determined by means of an enzyme reaction (kit used to investigate the LDH content from Roche). The content of NPE 172O is a Pluronic(R) RPE 1720 PGE2 was determined using an ELISA test (ELISA kit from Roche). Following trypsin treatment, the cells were centri fuged and counted. P105 is Pluronic(R) P105 or Poloxamer 335 (USAN) (O157 UVB-LDH LDH or lactate dehydrogenase determi Anti-Radical Action Testing nation by means of an enzyme reaction 0146 The oxidative anti-stress properties were evaluated UVB-PGE2 prostaglandins E2 determined using an ELISA by “in tubo' and “in vitro” tests. test (ELISA kit from Roche). 0147 The group of in tubo tests includes both the initial % AO-DPPH Anti-Radical test using diphenylpicrylhydra radical-type forms of oxygen and the reactive forms intro Zyl duced in Vivo: radical hydroxyl (HO and anion superoxide % AO-TBARS Thiobarbituric Acid Reactive Assay See (O). above. US 2015/O 140141 A1 May 21, 2015 10

TABLE 3 Extracts of Cassia alata leaves with quantification of flavonoids Kaempferol-3-O- Kaempferol Active sophoroside (K3OS) (mg/100g of Surfactant Matter (mg/100g of liquid Surfactant Wt.%. (g/100g) liquid extract) extract) Cassia None (water) O 3.59 225 O alata APG-1 1 3.65 217 extracts APG-2 5 3.86 220 3.6 L3S 10 3.67 269 9.1 L43 10 3.80 272 11.3 L44 10 4.31 268 19.7 RPE1720 10 2.35 217 P105 10 4.85 286 26.6

TABLE 4 TABLE 6-continued Comparison of anti-UVB activities between water and aqueous medium Comparison of anti-UVB activities between water and aqueous medium containing non-ionic Surfactants extracts of Cassia alata leaves (all containing non-ionic Surfactants extracts of Argania spinosa leaves (all liquid extracts were tested at a 0.5% dilution liquid extracts were tested at a 0.037% dilution)

Wt. 90 LDH PGE2 LDH Species Extract Surf (Umg protein) (pg. well) Surfactant (Umg PGE2 Cassia Control without UV O -4 Species Surfactant Wt. 96. protein) pg?well alata Control with UV 1OO 1OO extracts Positive control 15 -6 Control 100 1OO (aspirin at 0.03%) with UV Water 42 29 Positive O O APG-1 1 NT NT control APG-2 5 118 34 (aspirin at L3S 10 52 18 0.03%) L43 10 41 1 Argania None O 79 58 LA4 10 29 2 spinosa (water) NPE1720 10 140 15 Leaves APG-1 1 86 84 P105 10 4 -1 extracts APG-2 5 48 42 L3S 10 78 55 L43 10 56 23 LA4 10 81 33 TABLE 5 RPE1720 10 86 52 Extracts of Argania Spinosa leaves with quantification of flavonoids P105 10 4 O Myricitrin Quercitrin Active Matter (mg/100 g (mg/100 g Surfactant (g/100g of of liquid of liquid 0158. The dry weight of the plant species in all cases is 5 Species Surfactant Wt.%. liquid extract) extract) extract) wt.% of the total slurry weight in Table 7. The slurries are stirred for 1-2 hours at room temperature before measure Argania None O 4.27 37.9 24.4 spinosa (water) ments are taken for grams of active extractant per 100/g of Leaves APG-1 1 4.08 38.2 23.9 liquid, flavonoid concentration and biological testing. extracts APG-2 5 4.63 46.9 32.8 L3S 10 3.37 SS.4 35.4 TABLE 7 L43 10 2.16 SO4 31.0 LA4 10 2.90 S3.6 33.5 Extracts of Cacao alata with quantification of flavonoid and RPE1720 10 1.42 35.3 19.1 corresponding biologic activity P105 10 6.29 76.O 52.4 Kaempferol (% var. Wt.% Extract vs. H2O UVB- UVB TABLE 6 Species Surfactant Surf. (g 100 g) ext.) LDH PGE Comparison of anti-UVB activities between water and aqueous medium Cacao None O.22 O 42 29 containing non-ionic Surfactants extracts of Argania spinosa leaves (all alata (water) liquid extracts were tested at a 0.037% dilution APG-1 1 O.10 neg. APG-2 1 O.10 neg. 118 34 LDH L3S 10 O.25 1940 52 18 Surfactant (Umg PGE2 L43 10 O.39 20.72 41 1 Species Surfactant Wt. 96. protein) pg?well L44 5 O.32 1912 29 2 NPE1720 1 O.33 neg. 140 15 Control O O P105 1 O.15 2.7 4 neg. without UW US 2015/O 140141 A1 May 21, 2015 11

Formulation Examples -continued Example 1A Day Cream with Naturally Sourced UV Protection Ph. Trade Name INCI Name % wt 0159) Citric Acid 25% Citric Acid C.S. Sol. Purifying Toner for Skin Supplier Footnotes: C.P. Kleco Ph. Trade Name INCI Name % wt *RT Vanderbilt Shulke A Deionized Water Water 89.40 Intarone Glycerin Glycerin 3.00 Elestab (R388 Propylene Glycol (and) Phenoxyethanol 1.OO (0163 Procedure (and) Chlorphenesin (and) Methylparaben 0164 Combine Phase A and start heating to 75-80 C. D-Panthenol 75 Panthenol OSO Premix Phase Band add to Phase A while heating to 75-80 C. W Combine Phase C and heat to 75-80 C. Combine Phase D B Eumulgin (R) Coceth-7 (and) PPG-1-PEG-9 Lauryl 1...SO HPS Glycol Ether (and) PEG-40 Hydrogenated homogenize until uniform then add to Phase C and continue Castor Oil heating to 75-80 C. Add Phase C/D to Phase A/B while Copherol (R1250 Tocopheryl Acetate OSO homogenizing until uniform. Transfer to Sweep mixing and C start cooling to 40 C. Add Phase E ingredients one by one and Ocean Breeze Fragrance O.10 6110736 mix well between additions. Cool to room temperature and C Mat-XSTM Water (and) Butylene Glycol (and) Xanthan 2.00 stop. Clinical Gum (and) Sarcosine Extract according Exact (and) water (and) nonionic Surfactant .01-5 Example 3A to invention TEA99% Triethanolamine C.S. (0165

Supplier Footnotes: 'Bell Flavors and Fragrances Moisturizing Makeup Removing Wipe Ph. Trade Name INCI Name % wt (0160 Procedure A Deionized Water Water q.S. to 100 0161 While stirring Phase A, add premixed Phase B. Then Emulgade (RCM Cetearyl Isononanoate 6.OO-1O.OO (and) Ceteareth-20 (and) add Phase C one by one, and mix well between additions. Cetearyl Alcohol (and) Glyceryl Stearate (and) Glycerin (and) Ceteareth Example 2A 12 (and) Cetyl Palmitate Extract according to the Extract according to the O1-500 (0162 Invention invention Citric Acid (50% Soln) Citric Acid O.10 Fragrance Fragrance C.S. Preservative Preservative C.S. Day Cream with Naturally Sourced UV Protection Viscosity mPas: Brook. RVF, 23°C., spindle 4, 10 rpm. pH: 4.9-5.1 Ph. Trade Name INCI Name % wt A Deionized Water Water C.S. Edeta (RBD Disodium EDTA O.10 Example 4A D-Panthenol (R) Panthenol 0.75 75 W (0166 B Glycerin Glycerin 99% 2.00 Keltrol CG Xantham Gum O.20 Veegum Ultra Magnesium Aluminum Silicate O.40 Night Cream C Lanette (R) 22 Behenyl Alcohol 2.00 Eumulgin (R) SG Sodium Stearoyl Glutamate 0.75 Ph. Trade Name INCI Name % wt Myritol (R) 331 Cocoglycerides 3.SO Emuigade (RPL Cetearyl Glucoside (and) Cetearyl 3.SO A Deionized Water Water 65.15 68; SO Alcohol Elestab 388 Propylene glycol (and) Phenoxyethanol 1.00 Cetiol (R) SB 45 Butyrospermum Parkii (Shea) Butter 1...SO (and) Chlorphenesin (and) Cetiol (R) OE Dicaprylyl Ether 3.00 Methylparaben D Z-COTE(R) LSA Zinc Oxide (and ) 12.SO B Glycerin Glycerin 3.00 Triethoxycaprylysilane Vanzan NF' Xanthan gum O.10 Cetiol (R) RLF Caprylyl Caprylate/Caprate 7.00 COSmedia (RSP Sodium Polyacrylate O.70 Cetiol (R) CC Dicaprylyl Carbonate 7.50 C Emulgade (R) Sucro Sucrose Polystearate (and) 3.00 E Sensiva SC 50 Ethylhexylglycerin 1.00 Hydrogenated Polyisobutene Marine Filling Pentaerytrityl Tetraisostearate (and) 1.00 Eumulgin (R) SG Sodium Stearoyl Glutamate 1.OO Spheres Silica Dimethyl Sylilate (and ) Cutina (R) HVG Hydrogenated Vegetable Glycerides 4.OO Sodium Chondroitin Sulfate (and) Monomuls (R90-O 18 Glyceryl Oleate OSO Extract according to the invenion Cetiol (R) RLF Caprylyl Caprylate? Caprate 3.00 Ocean Breeze Fragrance O.10 Myritol (R) 312 Caprylic Capric Triglycerides 6.OO 6110736 Cetiol (R) J600 Oley Erucate 6.OO US 2015/O 140141 A1 May 21, 2015 12

-continued Example 6A

Night Cream 0172

Ph. Trade Name INCI Name % wt After-Sun Gel for Sensitive Skin Generol (R) R Brassica Campestris (Rapeseed) Sterols 0.50 Dow Corning 200 Dimethicone 1.OO Ph. Trade Name NCI Name % wt Fluid 350 cSt A Dehyguart (R) F75 Distearoylethyl Hydroxyethylmonium O.70 D HyalufixTM GL Water (and) Butylene Glycol (and) 3.00 Methosulfate (and) Cetearyl Alcohol Alpinia Galanga Leaf Extract (and) Emulgade (R) Sucrose Polystearate (and) O.SO Xanthan Gum (and) Caprylic Capric Sucro Hydrogenated Polyisobutene Cutina (R) PES Pentaerythrityl Distearate 1.00 Triglyceride Cutina (R) GMS V Glyceryl Stearate 1.00 Extract according to Extract (and) Xanthan Gum 2.OO Cetiol (R) Sensoft Propylheptyl Caprylate 3.00 the invention Myritol (R) 331 Cocoglycerides 2.00 Lavender Vanilla F- Frangrance O.OS Cyperus Root Oil Cyperus Esculentus Root Oil 2.00 Cosmedia (R) Polyguaternium-37 (and) Dicaprylyl 1...SO 12798.13 Triple C Carbonate (and) Lauryl Glucoside B Glycerin Glycerin 3.00 Viscosity: Brookfield RVT, 23°C., spindle T-E (a) 5 rpm: 180,000 cps pH: 6.3 Elestab (R388 Propylene Glycol (and) 1.00 Supplier Footnotes: Phenoxyethanol (and) Chlorphenesin (and) Methylparaben 'RT Vanderbilt, Inc Deionized Water Water 77.70 'Dow Corning Corp, C Extract according Water (and) Extract 1.00 Intarome Fragrance and Flavor Corp, to the invention SkinasensylTM Mannitol (and) Sodium Citrate (and) O.30 PWLS 9852 Acetyl Tetrapeptide-15 (0167 Procedure Ethanol Ethanol S.OO D NaOH (10%) Sodium Hydroxide C.S. (0168 Premix Phase B and swell the mixture in the water Floral Plumeria F- Fragrance O.30 Phase of Phase A. Then heat to 85 C. Heat Phase C to 85C and 1279851 mix until homogeneous. While stirring add Phase C to Phase Viscosity: Brookfield RVT, 23°C., spindle T-E (a) 5 rpm, with Helipath: 120,000 cps pH: 4.0-4. 5 A/B. Allow the emulsion to cool while stirring in such a way Supplier Footnotes: that it remains in continual motion. Avoid incorporating air. If 'Intarome Fragrance and Flavor Corp, necessary homogenize with a suitable dispersion unit (like Ultra Turrax) at approx. 65-60 C. When mixture cools to Procedure below 50 C, add Phase D while mixing. Stir while cooling 0173 until reaches room temperature. (0174 Heat Phase A and B separately to 80-85 C. Add Phase B to A. under moderate mixing. Start cooling. Add Example 5A Phase Cat 45 Corbelow and mix well between each addition. Add Phase D one by one, mix well between additions, than cool to room temperature and stop. (0169 Example 7A Skin Serum 0175 Ph. Trade Name NCI Name % wt A Deionized Water Water 84.7 Glycerin Glycerin 3.00 No-Foam Cleanser Elestab 388 Propylene Glycol (and) Phenoxyethanol 1.00 (and) Chlorphenesin (and) Methylparaben Ph. Trade Name INCI Name % wt Cosmedia (R) SP Sodium Polyacrylate O.80 Cetiol (R) Sensoft Propylheptyl Caprylate 3.00 A Eumulgin (RVL 75 Lauryl Glucoside (and) Polygercyl-2 1...SO Eutanol (R) G 16 S Hexyldecyl Stearate 2.00 Dipolyhydroxystearate (and) Glycerin Cetiol (R) 868 Ethylhexyl Stearate 2.00 Cutina (R) HVG Hydrogenated Vegetable Glycerides 1...SO Activwhite TMLS Water (and) Glycerin (and) Sucrose 3.00 Cutina (R) PES Pentaerythrityl Distearate 1.OO 98O8 Dilaurate (and) Polysorbate 20 (and) Cetiol (R) CC Dicaprylyl Carbonate 3.00 Pisum Sativum (Pea) Extract Luvitol (R) Lite Hydrogenated Polyisobutane 3.00 Extract according Water (and) Extract 2.00 Myritol (R) 331 Cocoglycerides 2.OO to the invention COSmedia (RSP Sodium Polyacrylate O.8O Bisabolo Natural Bisabolol O.SO B Deionized Water Water 80.65 Glycerin Glycerin 3.00 Viscosity:Brookfield RVT.23°C., spindle T-C (a) 10 rpm, with Helipath: 12000 cpspH: 5.80 Elestab (R388 Propylene Glycol (and) Phenoxyethanol 1.OO (and) Chlorphenesin (and) Methylparaben Horse Chestnut Mannitol (and) Ammonium Glycyrrhizate 1.00 Procedure Extract (and) Caffeine (and) Zinc Gluconate (and) 0170 Aescuius Hippocastantin (Horse Mix Phase A and while stirring, slowly add Phase B Chestnut) Seed Extract 0171 NaOH (10%) Sodium Hydroxide (and) Water C.S. to Phase A. When Phase B completely swells, add each ingre C Extract according to Water (and) Extract 1...SO dient of Phase C one at a time into the gel Phase. When the invention completely mixed, add Phase D ingredients one at a time. US 2015/O 140141 A1 May 21, 2015

-continued Example 9A

No-Foam Cleanser 0183)

Ph. Trade Name INCI Name % wt Skin Firming Lotion Champagne Petals O.OS RU-2133 Ph. Trade Name INCI Name % wt

Viscosity: Brookfield RVT, 23°C., spindle T-E (a) 5 rpm, with Helipath: 61,000 cps pH: 6.0 A Deionized Water Water 6840 Supplier Footnotes: Glycerin Glycerin 3.00 'Takasago International Corp. Elestab (R388 Propylene Glycol (and) Phenoxyethanol 1.OO (and) Chlorphenesin (and) Methylparaben (0176 Procedure Vanzan NF Xanthan Gum O.10 COSmedia (RSP Sodium Polyacrylate 1.OO 0177 Combine Phase A, without Cosmedia SP and heat to B Plantapon (R) LGC Sodium Lauryl Glucose Carboxylate 1...SO 80-85 C. Sprinkle Cosmedia SP into Phase A while at 80-85 Sorb (and) Lauryl Glucoside C and mix well. Combine Phase B and heat to 80-85 C. Add C Dehymuls (R) PGPH Polyglyceryl-2 Dipolyhydroxystearate 4.OO Phase B to Phase A while at 80-85 C and mix well. Start Cetiol (R) Sensoft Propylheptyl Caprylate S.OO Myritol (R) 331 Cocoglyceride 3.00 cooling, and homogenize at 55-60C. Add Phase C at 40 C or Cetiol (R) J600 Oley Erucate 1.OO below one by one and mix well between additions. Cool to Cetiol (R) SB 45 Butyrospermum Parkii (Shea) Butter 2.OO room temperature and stop. D Champagne Petals 3.00 RU-2133 E Extract according to Water (and) Extract 2.OO Example 8A the invention 0178 Baobab Extract Hydrolyzed Adansonia Digitata Extract S.OO Viscosity: Brookfield RVT, 23°C., spindle #5 (a) 10 rpm; 7.800 cps pH: 5.5 Supplier Footnotes: Eye Crean RT Vanderbilt, Inc 2 Takasago International Corp, Ph. Trade Name INCI Name % wt 0.184 Procedure A Emulgade (R) Glyceryl Stearate (and) Ceteareth-20 (and) S.OO SE-PF Ceteareth-12 (and) Cetearyl Alcohol (and) 0185 Swell pre-mixed Cosmedia SP and Vanzan NF in Cetyl Palmitate Phase A. Add Phase B and mix homogeneously. Heat Phase C Emulgade (R) PL Cetearyl Glucoside (and) Cetearyl Alcohol 2.OO to 45-50 C just enough to melt shea butter. Mix homoge 68; SO Cetiol (R) RLF Caprylyl Caprylate/Caprate S.OO neously and cool to room temp. Add Phase D to Phase C and Cetiol (R) MM Myristyl Myristate OSO mix well. Cetiol (R) SB 45 Butyrospermum Parkii (Shea) Butter 1.OO 0186. Then slowly add oil Phase C/D to the water Phase Cetiol (R) Sensoft Propylheptyl Caprylate 2.OO A/B while stirring. Avoid incorporating air. If necessary Eutanol (R) G Octyldodecanol 2.OO Covi-ox (RT 70 C Tocopherol OSO homogenize with a suitable dispersion unit (e.g. Ultra Tur Dow Corning 200 Dimethicone OSO rex). Fluid 350 cSt 0187. Add ingredients in Phase E one by one while mix Cosmedia (R) SP Sodium Polyacrylate OSO Vanzan NF Xanthan Gum O.2O ing. B Deionized Water Water 70.70 Glycerin Glycerin 3.00 Example 10A Elestab (R388 Propylene Glycol (and) Phenoxyethanol 1.OO (and) Chlorphenesin (and) Methylparaben 0188 C AMC TM Glycerin (and) Water (and) Sodium PCA 3.00 (and) Urea, (and) Trehalose (and) Triacetin (and) Sodium Hyaluronate (and) Polyguaternium-51 Body Lotion Extract according Water (and) Extract (and) Xanthan Gum 3.00 to the invention Ph. Trade Name INCI Name % wt Champagne Petals O.10 RU-2133 A Emulgade (R) PL 68/50 Cetearyl Glucoside (and) Cetearyl 5.00 Alcohol Viscosity: Brookfield RVT, 23°C., spindle T-E (a) 5 rpm, with Helipath: 30,000 cps pH: 6.0 Cutina (R) CP Cetyl Palmitate 3.00 Supplier Footnotes: Monomuls(R 90-O 18 Glyceryl Oleate O.SO 'Dow Corning Corporation Cetiol (R) OE Dicaprylyl Ether 2.00 *RTVnaderbilt, inc Myritol (R) 312 Caprylic Capric Triglyceride S.OO Takasago International Corp. Cegesoft (R) PS 6 Vegetable Oil 4.OO Cegesoft (R) VP Vegetable Oil (and) Hydrogenated 1.00 Vegetable Oil (and) Euphorbia 0179 Procedure Cerifera (Candelilla) Wax 0180 Heat Phase A (without Cosmedia SP and Xanthan B Deionized Water Water 74.15 Vanzan NF (RT Xanthan Gum O.SO Gum) and Phase B to 80-85 C. While stirring Phase A, dis Vanderbilt) perse Cosmedia SP and Xanthan Gum. Glycerin Glycerin 3.00 0181 Combine and heat Phase B to 80-85C then add to Potassium Sorbate Potassium Sorbate O.30 Phase A, while mixing. Elestab (R) CPN Chlorphenesin O.25 Eumulgin (R) SG Sodium Stearoyl Glutamate 1.00 0182 Start cooling. Homogenize at 55-60C. Add Phase C C Extract according to the Extract (and) Pluronic (R) O.20 one by one at 40 C or below, mix well between additions, then invention cool to room temperature and stop. US 2015/O 140141 A1 May 21, 2015

-continued and the target skin bioactive is a flavonoid or flavonoid derivative. Body Lotion 2. The method according to claim 1, wherein the nonionic surfactant is a triblock copolymer defined by the formula (I) Ph. Trade Name INCI Name % wt or (II) Bergamot & Jasmine O.10 Musk F-127986 HO(CHO)(CHO) (C2HO)OH (I) Citric Acid (25%) Citric Acid C.S. O Viscosity: Brookfield RVT, 23°C., spindle T-E (G5 rpm; 40,000 cps pH: 6.4 Supplier Footnotes: HO(CHO)(CHO) (CHO),OH (II) RT Vanderbilt, Inc 'Jeen International Corporation wherein a and c are independently 3 to 200, Inatome Fragrance and Flavor Corp and b and d are independently is 5 to 100. 3. The method according to claim 1, wherein the nonionic (0189 Procedure Surfactant is the alkyl polyglucoside and is defined by the (0190. Prepare Phase B. Hydrate the thickeners first, then formula add the rest of the ingredients while mixing. Heat Phase A and B to 80-85 C. Add Phase B to Phase A, then cool to 55-60 C and homogenize. Transfer to regular mixing and continue wherein R is a monovalent organic radical having from cooling. Add Phase C one by one at 40 C or below and mix about 6 to about 30 carbon atoms, R is a divalent alky well between additions. If necessary adjust pH with citric lene radical having from 2 to 4 carbon atoms, and Z is a acid. Saccharide residue having 5 or 6 carbon atoms, b is a number from 0 to about 12, and a is a number of from 1 Example 1 1A to 6. 4. The method according to claim 1, wherein the biomass is (0191) a flavonoid rich plant, algae or fungi. 5. The method according to claim 1, wherein the flavonoid Lipstick or other anhydrous product type or flavonoid derivative is selected from compounds compris ing the cyclic cores Phase Ingredient Wt.% (w/w) A. Mineral wax 17.0 Isostearyl isostearate 31.5 (A) Propylene glycol 2.6 dipelargonate Propylene glycol 1.7 isostearate PEG 8 beeswax 3.0 Hydrogenated palm kernel 3.4 oil, glycerides, hydrogenated palm glyceride Lanolin oil 3.4 Sesame oil 1.7 (B) Tribehenin 1.7 Cetyl lactate 3.0 Mineral oil, lanolin alcohol 3.0 B Castor oil qsp 100 Titanium dioxide 3.9 CI15850:1 616 and CI4S410:1 .256 CI 1914.0:1 048 (C) CI77491 1.048 C Extract according to OO1-5 invention

1. A method of extraction of at least one target skin bioac tive from algae, fungi or botantical biomass, which method comprises a) contacting the algae, fungi or botanical biomass with an 6. The method according to claim 1, wherein the flavonoid aqueous liquid to form a slurry, wherein the aqueous or flavonoid derivative is selected from the group consisting liquid comprises about 0.01 to about 20, wt.% of a of abyssinone I, abyssinone V. afzelechin, ampelopsin, aro nonionic Surfactant selected from the group consisting madendrin, asebogenin, auriculoside, betagarin, broussin, of block copolymers of poly(ethylene oxide)/poly(pro broussonin C, butin, butrin, (+)-catechin, catechin 7-O-B- pyleneoxide) and alkyl polyglucosides and the wt. per xyloside, davidigenin, diffutin, 7.4-dihydroxylflavan, 2,6-di cent is based on the total weight of the slurry, hydroxyl-4'-methoxydihydro-chalcone, 7.3'-dihydroxyl-4- and methoxy-8-methylflavan, 7.4'-dihydroxyl-8-methylfalvan, b) optionally, separating the biomass from the aqueous 6,8-diprenylmaringenin, dracorubin, (-)-epicatechin, ent-epi slurry, catechen, epigallo catechin 3-gallate, eriocitrin, eriodictyol. US 2015/O 140141 A1 May 21, 2015

farrerol, fisetinidol, fisetinidol-4-ol, fustin, garbanzol, glab 8. The method according to claim 1, wherein the slurry in ranin, glepidotin B. glycyphyllin, hesperetin, hesperidin, step a) is essentially organic solvent free. homoeriodictyol. 7-hydroxyflavan, isochamaejasmin, isos 9. A method of increasing the flux during a filtration pro akuranetin, isouriaretin, kazinola, kolaflavanone, liquiretige cess of a solid biomass from an aqueous extract, by addition of a surfactant to an aqueous medium and extracting the Solid nin, manniflavanone, 6, methoxyaromadendrin 3-O-acetate, biomass, 6-methoxytaxifolin, 2'-O-methylodoratol, maringenin, narin wherein the nonionic Surfactant is a surfactant selected gin, narirutin, neoastilbin, neoeriocitrin, neohesperidin, odo from the group consisting of block copolymers of poly ratol, phloretin, phellamurin, phloretin, phloridzin, (ethylene oxide)/poly(propyleneoxide) and alkyl poly pinobanksin, pinocembrin, pinocembrin 7-rhamnosyl-gluco glucosides and the aqueous extract comprises at least a side, piperaduncin B, poncirin, 5'-prenyl, naringenin, prun flavonoid or flavonoid derivative. ing, Sakuranetin, Sanggenon C. Sanggenon D, silandrin, sily 10. A method of increasing the flavonoid extraction from a bin, sillychristin, Sophoranone, strobopinin, taxifolen, flavonoid rich plant by addition of a surfactant to an aqueous taxifolin-3-O-acetate, tephrowatsin, theasinensin A, 2',4',6'- medium and extracting the flavonoid rich plant, wherein the trihydroxyl-3'-formyldihydrochalcone and uvaretin. nonionic Surfactant is a surfactant selected from the group 7. The method according to claim 1, wherein the biomass is consisting of block copolymers of poly(ethylene oxide)/poly a plant and selected from the group consisting of Cassia (propyleneoxide) and alkyl polyglucosides. alata, Argania spinosa and Cocoa Callus. k k k k k