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(12) Patent Application Publication (10) Pub. No.: US 2011/0046077 A1 Talamond Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2011/0046077 A1 Talamond Et Al US 2011 0046077A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0046077 A1 Talamond et al. (43) Pub. Date: Feb. 24, 2011 (54) PROCESS FOR THE EXTRACTION OF (86). PCT No.: PCT/EP09/54349 MANGIFERN AND SOMANGFERIN S371 (c)(1), (75) Inventors: Pascale Talamond, Eyragues (FR): (2), (4) Date: Oct. 7, 2010 Laurence Mondolot, Montpellier (30) Foreign Application Priority Data (FR); Annick Gargadennec, Montpellier (FR): Alexandre De Apr. 11, 2008 (FR) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - O852468 Kochiko, Montpellier (FR); Serge Publication Classification Hamon, Teyran (FR); Alain (51) Int. Cl. A.audine Campa,NE Teyran Er (FR) A63L/7048C7H I/08 (2006.01) A6IR 8/60 (2006.01) Correspondence Address: A6IP3/10 (2006.01) MARSHALL, GERSTEIN & BORUN LLP A6IP39/06 (2006.01) 233 SOUTH WACKER DRIVE, 6300 WILLIS A6IP37/08 (2006.01) TOWER A61O 19/00 (2006.01) CHICAGO, IL 60606–6357 (US) (52) U.S. Cl. ........................................... 514/23: 536/128 (57) ABSTRACT (73) Assignee: Institut De Recherche Pour Le The present invention relates to methods for extracting and Developpement (IRD), Marseille 2 isolating glycosyl Xanthone derivatives, in particular (FR) mangiferin and isomangiferin, from plants of the Rubiaceae family, especially of the Coffea genus. The invention also (21) Appl. No.: 12/936,859 relates to extracts obtained using Such methods, as well as compositions comprising such extracts that are useful in the (22) PCT Filed: Apr. 10, 2009 cosmetic and pharmaceutical industry. Patent Application Publication Feb. 24, 2011 Sheet 1 of 2 US 2011/0046077 A1 Figure 1 Patent Application Publication Feb. 24, 2011 Sheet 2 of 2 US 2011/0046077 A1 O4 3. O n ' : - 200 250 3. 35 400 Figure 2 US 2011/0046077 A1 Feb. 24, 2011 PROCESS FOR THE EXTRACTION OF Rubiaceae, to which in particular gardenia (genus Gardenia), MANGIFERN AND SOMANGFERIN cinchona (genus Cinchona) and the coffee plant (genus Cof fea) belong. RELATED APPLICATIONS 0005. Due to its impact on the quality of coffee, a great deal of information exists on the chemical composition of 0001. This application claims priority to French Patent green or roasted coffee beans. The majority of studies have Application No. FR 08524 68 filed on Apr. 11, 2008, which been carried out on cultivated species, such as Coffea arabica is incorporated herein by reference in its entirety. and Coffea canephora. The biochemical composition of cof fee beans has also been studied for some of the 103 wild FIELD OF THE INVENTION species identified to date (Anthony et al., 1993; Campa et al., 2005a; Campa et al., 2005b), revealing that sugars, lipids, 0002 The present invention relates to a process for obtain chlorogenic acids, amino acids, caffeine and trigonelline are ing C-glycosylxanthone derivatives, in particular mangiferin generally the main compounds which accumulate during the and isomangiferin, from plants of the Rubiaceae family. Such growth of the coffee bean (Tressl, 1989; Ho et al., 1993). The as plants of the Coffea genus. inter- and intra-species diversity of the metabolic content has been extensively studied (Clifford, 1985; Rogers, 1999) and the results obtained have shown that chlorogenic acids, which BACKGROUND OF THE INVENTION are soluble phenolic compounds, strongly accumulate in the 0003. Mangiferin and isomangiferin are natural products green beans, except in the case of the wild species, such as present in a number of plants. They are C-glycosyl Xanthone Coffea pseudozanguebariae. In contrast, very few biochemi derivatives that have numerous advantageous properties from cal analyses have been carried out on the leaves of wild or the cosmetic and pharmaceutical viewpoint. In fact, it has cultivated species. The most recent studies have evaluated the been demonstrated that mangiferin, just like other Xanthone caffeine and trigonelline contents in the leaves of C. arabica derivatives, has antidiabetic (Miura et al., 2001), antioxidant (Zheng and Ashihara, 2004) and the chlorogenic acid content (Garrido et al., 2004), antiallergic (Pinto et al., 2005), anti in the leaves of C. pseudozanguebariae (Bertrandet al., 2003) hyperlipidaemic (Muruganandan et al., 2005) and anticarci and C. canephora (Mondolot et al., 2006). nogenic (Pinto et al., 2005) properties as well as cardiotonic and diuretic properties (GB 1 099 764). It has also been SUMMARY OF THE INVENTION suggested that mangiferin could be used in the treatment of 0006. The inventors have, for the first time, demonstrated diseases and clinical conditions caused by the herpes virus the presence of Xanthone derivatives, in particular C-glycosyl (GB 2 108 383). Furthermore, due to its anti-collagenase, xanthone derivatives, in plants of the family of the Rubiaceae anti-elastase, anti-tyrosinase and anti-radical activities and to and have developed methods for the extraction and isolation its photoprotective activities in the region of ultraviolet (UV) of such derivatives. In particular, the inventors have shown radiation, mangiferin is of use in protecting the skin from UV that the leaves of some species of coffee plants comprise radiation, in improving its structural quality and in helping to significant amounts of C-glycosyl Xanthones, in particular of combat biological and/or radiation-induced skin ageing (WO mangiferin and isomangiferin. They have also shown that 96/16632). Moreover, it has been demonstrated that mangiferin is present in the leaves of the species of Rondele mangiferin activates the expression of heat-shock proteins tia odorata. and inhibits the expression of matrix metalloproteases, thus 0007 Thus, the present invention generally relates to pro improving the cellular response to heat shock (US 2006/ cesses for obtaining C-glycosyl Xanthones from one or more 0088,560). plants belonging to one or more species of the Rubiaceae 0004. Mangiferin and isomangiferin (the chemical struc family. The plant of the Rubiaceae family may belong to a tures of which are presented on FIG.1) belong to the xanthone Subfamily selected from the group consisting of Rubioideae, family. This family forms a large group of natural products Cinchonoideae. Ixoroideae, and Antirheoideae. which are generally found only in Some families of higher 0008. The plants of the Rubiaceae family may belong to a plants, in lichens and in fungi (Sultanbawa, 1980; Hostett genus selected from the group consisting of Acranthera, mann and Hostetmann, 1989). An analysis of the scientific Acrobotrys, Acunaeanthus, Adina, Adinauclea, Agathisan literature has shown that 515 different natural Xanthones were themum, Aidia, Aidiopsis, Airosperma, Aitchisonia, Alberta, identified from January 2000 to December 2004 (i.e., within Aleisanthia, Alibertia, Allaeophania, Alleizettella, Allenan only 5 years), 278 of these xanthones being new xanthones thus Alseis, Amaioua, Amaracarpus, Amphiasma, Amphi discovered for the first time (Viera and Kijoa, 2005). Despite dasya, Ancylanthos, Anomanthodia, Antherostele, Anthor their high biochemical diversity, the xanthones of higher rhiza, Anthospermum, Antirhea, Aoranthe, Aphaenandra, plants are mainly associated with the Clusiaceae and Genti Aphanocarpus, Appunia, Arachnothryx, Arcytophyllum, anaceae families. They are occasionally found in phyloge Argocoffeopsis, Argostemma Ariadne, Asemnantha Asperu netically distant families. Such as the Iridaceae, Liliaceae, galium, Asperula Astiella, Atractocarpus, Atractogyne, Anacardiaceae, Euphorbiaceae or Verbenaceae. Thus, Augusta, Aulacocalyx, Badusa, Balnea, Bancalus, Bathysa, mangiferin, which was initially isolated from Mangifera Batopedina, Becheria, Belonophora, Benkara, Benzonia, indica L. (Anacardiaceae), is naturally present in a number of Berghesia, Bertiera, Bikkia, Blandibractea, Blepharidium, species of the families of the Fabaceae, Gentianaceae, Anac Bobea, Boholia, Borojoa, Bothriospora, Botryarrhena, Bou ardiaceae, Flacourtiaceae, Polypodiaceae, Guttiferae, Legu vardia, Brachytome, Bradea, Brenania, Breonadia, Breonia, minosae, Hippocrateaceae, Sapotaceae, Convolvulaceae, Burchelia, Burttaavya, Byrsophyllum, Calanda, Callipeltis, Liliaceae, Iridaceae and Poaceae. Just like the other natural Calochone, Calycophyllum, Calycosia, Calycosiphonia, Xanthones identified to date, neither mangiferin nor iso Canephora, Canthium, Capirona, Captaincookia, Carpa mangiferin has been isolated from plants of the family of the coce, Carphalea, Carterella, Casasia, Catesbaea, Catunar US 2011/0046077 A1 Feb. 24, 2011 egan, Cephalanthus, Cephalodendron, Ceratopyxis, Neurocalyx, Nichallea, Nodocarpaea, Normandia, Nosto Ceriscoides, Ceuthocarpus, Chaetostachydium, Chalepo lachma, Ochreinauclea, Octotropis, Oldenlandia, Oldenlan phyllum, Chamaepentas, Chapelieria, Chassalia, Chaza diopsis, Oligocodon, Omiltemia, Opercularia, Ophiorrhiza, liella, Chimarrhis, Chiococca, Chione, Chomelia, Chou Ophryococcus, Oregandra, Osa, Otiophora, Otocalyx, lettia, Cigarrilla, Cinchona, Cladoceras, Clarkella, Otomeria, Ottoschmidtia, Oxyanthus, Oxyceros, Pachys Coccochondra, Coccocypselum, Codaria, Coddia, Coelopy tigma, Pachystylus, Paederia, Pagamea, Paganeopsis, Pali rena, Coelospermum, Coffea, Coleactina, Colletoecema, courea, Pamplethantha, Paracephaelis, Parachimarrhis, Commitheca, Condaminea, Conostomium, Conotrichia, Paracorynanthe, Paragenipa, Paraknoxia, Parapentas, Para Coprosma, Coptophyllum, Coptosapelta, Corynanthe, Cory triaina, Pauridiantha, Pausinystalia, Pavetta, Pavera, Pela phothamnus, Cosmibuena, Cosmocalyx, Coupoui,
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