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Phenolic Compounds with Cosmetic and Therapeutic Applications

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Phenolic Compounds with Cosmetic and Therapeutic Applications (19) & (11) EP 2 027 279 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C12P 19/46 (2006.01) 18.04.2012 Bulletin 2012/16 (86) International application number: (21) Application number: 07730118.2 PCT/EP2007/055815 (22) Date of filing: 13.06.2007 (87) International publication number: WO 2007/144368 (21.12.2007 Gazette 2007/51) (54) Phenolic compounds with cosmetic and therapeutic applications Phenolische Verbindungen mit kosmetischen und therapeutischen Anwendungen Composés phénoliques avec des utilisations cosmétiques et thérapeutiques (84) Designated Contracting States: • BAE ET AL: "Microbial approach to the AT BE BG CH CY CZ DE DK EE ES FI FR GB GR regioselective glycosylation of hydroxytyrosol" HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE JOURNAL OF THE KOREAN CHEMICAL SI SK TR SOCIETY, vol. 48, 2004, pages 111-114, XP002525761 (30) Priority: 14.06.2006 EP 06290972 • BRAUN ET AL: "Glucoside derivatives as novel photostabilizers for rigid PVC" DIE (43) Date of publication of application: ANGEWANDTE MAKROMOLEKULARE CHEMIE, 25.02.2009 Bulletin 2009/09 vol. 271, 1999, pages 93-100, XP000878315 • BERTRANDET AL: "Leuconostoc mesenteroides (73) Proprietor: Libragen glucansucrasesynthesis of flavonoid glucosides 31000 Toulouse (FR) by acceptor reactions in aqueous-organic solvents" CARBOHYDRATE RESEARCH, vol. (72) Inventors: 341, 10 March 2006 (2006-03-10), pages 855-863, • AURIOL, Daniel XP005394691 cited in the application 31300 Toulouse (FR) • MEULENBELD ET AL: "Enhanced (+)-catechin • NALIN, Renaud transglycosylating activity of Streptococcus 31280 Dremil-Lafage (FR) mutans GS-5 glucosyltransferase-D due to • ROBE, Patrick fructose removal" APPLIED AND 31450 Odars (FR) ENVIRONMENTAL MICROBIOLOGY, vol. 65, • LEFEVRE, Fabrice 1999, pages 4141-4147, XP002410550 cited in the 32120 Bajonnette (FR) application • KUMARASAMY ET AL: "The assessment of (74) Representative: Gallois, Valérie biological activities associated with the major Cabinet BECKER & ASSOCIES constituents of the methanol extract of "wild 25, rue Louis Le Grand carrot" (Daucus carota L.) seeds" JOURNAL OF 75002 Paris (FR) HERBAL PHARMACOTHERAPY, vol. 5, 2005, pages 61-72, XP008072520 (56) References cited: • SATO ET AL: "Alpha-anomer-selective • LIM ET AL: "Regioselectivity of glucosylation of glucosylation of (+)-catechin by the crude caffeic acid by a UDP-glucose: enzyme, showing glucosyl transfer activity, of glucosyltransferase is maintained in planta" Xanthomonas campestris WU-9701" JOURNAL BIOCHEMICAL JOURNAL, vol. 373, 2003, pages OF BIOSCIENCE AND BIOENGINEERING, vol. 90, 987-992, XP002276051 cited in the application 2000, pages 625-630, XP002525762 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 027 279 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 027 279 B1 • BRIGNOLAS ET AL: "Induced responses in phenolic metabolism in two Norway spruce clones after wounding and inoculations with Ophiostomapolonicum, a bark beetle- associated fungus" PLANT PHYSIOLOGY, vol. 109, 1995, pages 821-827, XP002424933 2 EP 2 027 279 B1 Description FIELD OF THE INVENTION 5 [0001] The present invention relates to the preparation of phenolics derivatives, pharmaceutic and cosmetic compo- sitions comprising such phenolics derivatives, and their use for the beauty of the skin and for treating diseases. BACKGROUND OF THE INVENTION 10 Phenolic compounds and their properties [0002] Phenolic compounds (also called phenolics), or polyphenols, constitute one of the most numerous and widely- distributed groups of substances in the plant kingdom, with more than 8,000 phenolic structures currently known. Polyphe- nols are products of the secondary metabolism of plants. The expression "phenolic compounds" embraces a considerable 15 range of substances that possess an aromatic ring bearing one or more hydroxyl substituents. Most of the major classes of plant polyphenol are listed in Table 1, according to the number of carbon atoms of the basic skeleton. The structure of natural polyphenols varies from simple molecules, such as phenolic acids, to highly polymerized compounds, such as condensed tannins (HARBORNE JB (1980) Plant phenolics. In: BELL EA, CHARLWOOD BV (eds) Encyclopedia of Plant Physiology, volume 8 Secondary Plant Products, Springer-Verlag, Berlin Heidelberg New York. Pp: 329-395). 20 [0003] The three important groups for humans are phenolic acids (C6- C1, C6-C2 and C6-C3), flavonoids (C6-C3-C6) and high-molecular weight polyphenols (more than 30 carbon atoms). Indeed, the phenolics, particularly polyphenols, exhibit a wide variety of beneficial biological activities in mammals, including antiviral, antibacterial, immune- stimulating, antiallergic, antihypertensive, antiischemic, antiarrhytmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory 25 actions. They are powerful antioxidants in vitro. TABLE I : The major classes of phenolic compounds (or phenolics) in plants (HARBORNE JB, 1980) NUMBER OF CARBON BASIC SKELETON CLASS EXAMPLES ATOMS 30 6 C6 Simple phenols Catechol, hydroquinone 2,6- Benzoquinones Dimethoxybenzoquinone 7JC6-C1 Phenolic acids Gallic, salicylic 35 8C6-C2 Acetophenones Tyrosine 3-Acetyl-6- derivatives Phenylacetic methoxybenzaldehyde acids Tyrosol p- Hydroxyphenylacetic 9C6-C3 Hydroxycinnamic acids Caffeic, ferulic Myristicin, 40 Phenylpropenes Coumarins eugenol Umbelliferone, Isocoumarins Chromones aesculetin Bergenon Eugenin 10 C6-C4 C6-C1-C6 Naphthoquinones Juglone, plumbagin Xanthones Mangiferin 45 14 C6-C2-C6 Stilbenes Anthraquinones Resveratrol Emodin 15 C6-C3-C6 Flavonoids Isoflavonoids Quercetin, cyanidin Genistein 18 (C6-C3)2 Lignans Neolignans Pinoresinol Eusiderin 30 (C6-C3-C6)2 Biflavonoids Amentoflavone 50 n(C6-C3)n Lignins (C6)n Catechol melanins (C6-C3-C6)n Flavolans (Condensed Tannins) 55 [0004] Among the phenolic acids, the most important constitutive carbon frameworks are the hydroxybenzoic (C6- C1) and hydroxycinnamic (C6-C3) structures. The hydroxybenzoic acid content of edible plants is generally very low, 3 EP 2 027 279 B1 with the exception of certain red fruits, black radish, and onions, which can have concentrations of several tens of milligrams per kilogram fresh weight. Hydroxybenzoic acids are components of complex structures such as hydrolyzable tannins (gallotannins in mangoes and ellagitannins in red fruits such as strawberries, raspberries and blackberries). The hydroxycinnamic acids are more common than are the hydroxybenzoic acids and consist chiefly of p-coumaric, caffeic, 5 ferulic and sinapic acids. These acids are rarely found in the free form, except in processed food that has undergone freezing, sterilization or fermentation. The bound forms are glycosylated derivatives or esters of quinic acid, shikimic acid and tartaric acid. Caffeic acid and quinic acid combine to form chlorogenic acid, which is found in many types of fruit and in high concentration in coffee. Caffeic acid, both free and esterified, is generally the most abundant phenolic acid and represents between 75% and 100% of the total hydroxycinnamic acid of most fruit (MANACH C, SCALBERT 10 A, MORAND C, REMESY C, JIMENEZ L (2004) Polyphenols: food sources and bioavailability. Am J Clin Nutr 79: 727-747). [0005] The flavonoids consist of a large group of low-molecular weight polyphenolic substances, benzo-γ-pyrone derivatives that are diverse in chemical structure; they represent the most common and widely distributed group of plant phenolics. The flavonoids common structure is that of diphenylpropanes (C6-C3-C6); its consists of two aromatic rings 15 (cycles A and B) linked through three carbons that usually form an oxygenated heterocycle (cycle C). Figure 1 shows the basic structure and the system used for the carbon numbering of the flavonoid nucleus. Structural variations within the rings subdivide the flavonoids into several families: flavonols, flavones, flavanols, isoflavones, antocyanidins and others. These flavonoids often occur as glycosides, glycosylation rendering the molecule more water-soluble and less reactive toward free radicals. The sugar most commonly involved in glycoside formation is glucose, although galactose, 20 rhamnose, xylose and arabinose also occur, as well as disaccharides such as rutinose. The flavonoid variants are all related by a common biosynthetic pathway, incorporating precursors from both the shikimate and the acetate-malonate pathways (CROZIER A, BURNS J, AZIZ AA, STEWART AJ, RABIASZ HS, JENKINS GI, EDWARDS CA, LEAN MEJ (2000) Antioxidant flavonols from fruits, vegetables and beverages: measurements and bioavailability. Biol Res 33: 79-88). Further modifications occur at various stages, resulting in an alteration in the extent of hydroxylation, methylation, 25 isoprenylation, dimerization and glycosylation (producing O- or C- glycosides). Phenolic compounds act as antioxidants with mechanisms involving both free radical scavenging and metal chelation. Indeed, excess levels of metal cations of iron, zinc and copper in the human body can promote the generation
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