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Fflc^Cj^^Lljp^ O Sources and Chemistry of Resveratrol fflc^cj^^lljp^ O Sources and Chemistry of Resveratrol Navindra P. Seeram University of California, Los Angeles Vishal V. Kulkarni and Subhash Padhye University of Pune, India CONTENTS Introduction 17 Sources of Resveratrol 18 Structure of Resveratrol 22 Chemical Analyses of Resveratrol 23 Synthesis of Resveratrol 24 Theoretical and SAR Studies of Resveratrol 25 Conclusion 26 References 26 INTRODUCTION Stilbenoids are phenol-based plant metabolites widely represented in nature and implicated with human health benefits against problems such as cancer, inflammation, neurodegenerative disease, and heart disease. Among stilbenes, the phytoalexin resveratrol (3,4',5-trihydroxystilbene; Figure 2.1) has attracted immense attention from biologists and chemists due to its numerous biological properties. Resveratrol is a pivotal molecule in plant biology and plays an important role as the parent molecule of oligo­ mers known as the viniferins [1]. It is also found in nature as closely related analogs, derivatives, and conjugates (Table 2.1) [1-80]. In addition, the inherent structural simplicity of the resveratrol molecule allows for the rational design of new chemotherapeutic agents, and hence a number of its synthetic adducts, analogs, derivatives, and conjugates have been reported (Table 2.1) [1-80]. 17 18 Resveratrol in Health and Disease Trans-resveratrol (frans-3,4',5-trihydroxystilbene) C/s-resveratrol (c/s-3,4',5-trihydroxystilbene) FIGURE 2.1 Chemical structures of trans- and r/.v-resveratrol (3.4'. .5-trihydrox- vstilbene). Numerous efforts have been directed to studies of structure-activity relationships (SARs) of resveratrol and its analogs with the goal of increasing and enhancing their //; V/IY; biological potency and bioavailability. The pharmacological activity of resveratrol has also stimulated the development of numerous chemical analytical methods for its measurement in different matrices such as plant extracts, wines and other beverages, and food-derived products, as well as in biological fluids and tissues. Because of the numerous biological properties and implications in health and disease associated with resveratrol, the focus of this chapter is on its occurrence, chemical analyses, synthesis, and studies of its chemistry. SOURCES OF RESVERATROL The sources of resveratrol and its related natural and synthetic derivatives, conjugates, and analogs are shown in Table 2.1 [1 80]. Res\eratrol was first identified in 1940 from the white hellebore lily VcrdHiini grciiulifloniiu O. Loes [81], although its richest known natural source is the Asian medicinal plant Folygomiin ciispidatitin (Japanese "Ko-jo-kon"). The occurrence of resveratrol was popularized in 1992 when it was discovered as a constituent of red wine, and implicated in the "French paradox," an epidemio­ logical finding of an inverse relationship between red wine consumption and the incidence of heart disease. Resveratrol has also been implicated with Sources and Chemistry of Resveratrol 19 TABLE 2.1 Natural and Synthetic Sources of Resveratrol and its Analogs Compound and sources Ref. Resveratrol (3.4'.5-lrihydro.\ystilbenc)" 1-13 Red grape, grapevine, grape leaf and berr\' skin, imiseadine grape, red wine, blueberry, cranberry, bilberry, lingonberry, sparkleberry. deerberry. partridgeberry; Polygonuiv cuspidulwu (Japanese knotweed); Monis spp. (including mulberry); lily {Vcrutnmi spp.); legumes [Cassia spp.. Pterolohiwu hcxapcuilliim): peanuts (Aiachls hypogaca): Rht'uni spp. (including rhubarb); eucalyptus; spruce (Picca spp); pine [Pimis spp.); Poaceae (grasses, including Festuca. Hordcum, Poa. Stipa. and Lolium spp.); Trifo/iiiui spp.; Nothofagus spp.; Artocarpus spp.; Gneium spp.; Plcuroptcrus ciliiiwrvis: Baultinia raceiuosa: Paeoniu lacliflora: Sci/la nervosa: Tctrastignui hypoglauvwu: Rwnvx hiiccphalophonis: Yucca spp.; Sniilax spp. Dihydrores\eralrol (/n;/;.v-.3.5.4'-trihydroxybibcnzylslilbene)"' 14. 15 Dioscorca spp.; Biilhopliyllum trisic Piceatannol or astringinin (//•i:(/;.v--'^.4,.3'.5'-tetrahydroxystilbene) .3, 15-20 White tea tree (Melaleuca leucadendron): Asian legume (Cassia garretliaiia). C. margiiiata: rhubarb (Rheum spp.); Euphorbia lagascae: Polygonwn ciispidaluiir. Vitis vinijera Dihydropiccalaniiol (//7/)).v-3.4,3'.5'-tctrahydroxybibenzylstilbene)'' 17 Cassia garrettiaiui Gnetol (nY«;.s-2.6.3'.5'.-tctrahydroxystilbene) 7. 21. 22 Gnetuiu spp. (including G. monaiuni. G. africanwu. G. giiei>u)ii, G. ula) Oxyresveratrol (/r((//.s-2.3'.4.5'-tclrahydroxyslilbene) '). 23-25 Moras spp.; Madura poiiiifera: Arioawpus gonwzlanus: Schoenocaulou officinale Hydroxyres\eratrol (//•rt/»-2.3,5.4'-tetrahydroxystilbcne) 3 Polygonum cuspidatum 7'/Y/«i--3.4.5.4'-tetrahydroxystilbene'' 26 r/Y/H.v-3.3'.4',5.5'-pentahydroxystilbcne" 27. 28 Eucalyptus wcmdoo: Vouacapoua americana. V. macropetala Pinosylvin (nY;/;.v-3.5-dihydroxystilbene)'' 1. 26. 29-34 Gneium cleistostachyum: Alpinia katsumadal; Polyalthia longifolia: Polygonum nodosum: Pinus spp. (including Scottish pine. P. sylvesiris) Dihydropinosylvin (/n/«.y-3.5-dihydroxybibenzylstilbene)" 35-37 Dioscorea halalas ryY»;.v-2.4.4'-trihydroxystilbcne" 36. 37 r/Y//;.v-3.5.3'-trihydroxystilbene" 38. 39 7'/Y//?.v-3.4.5-trihydroxystilbene" 40 rjY»«-3.4.4'-trihydroxystilbone'' 40. 41 r/Y//;.v-3.4-dihydroxystilbene'' 36. 37. 41 r(Y//;.v-3.4'-dihydroxystilbeiie'' 38. 39 r(Y»;.v-3.3'-dih\droxvstilbene'' 38. 39 (conlinued) 20 Resveratrol in Health and Disease TABLE 2.1 Continued Compound and sources Ref. r)Y(/).v-2.4-dihydroxystilbene'' 36. 37 ryYOT.v-4,4'-dihydroxyslilbenc" 36. 37. 40. 41 r/v/;)5-3-hydroxystilbene" 38. 39 ryv//i.s-4-hydroxystilbene (/j-hydroxystilbenc)'' 36. 37. 40 rjY//;,v-halogenatcd-3.5.4'-trihydroxystilbenes 42. 43 (lluoro-. chloro-, and iodorcsvcratrols)'' Dimethoxypinosylvin (//Y//(.v-3.5-dimcthoxystilbene)" 26 Rhapontigenin or 3-melhoxyies\'cratrol 6. 44. 45 (/ra/;.v-3.5.3'-trihydroxy-4'-melhoxystilbcne)" Rheum spp. [iiicliuling R. liuipontiiwn. R. wululatimi): Scilla nervosa Isorhapontigenin (//YH;.v-3.5.4'-trihydioxy-3'-methoxystilbcnc)'' 7. 46. 47 Giu'iiini spp.: Bekmieaiuhi chiiiensis Desoxyrhapontigenin or 4-mcthoxyresvcratrol 29. 48-50 (r/Y»7.v-3.5-dihydroxy-4'-mellioxyslilbene) Gnetuin eleisiosiiuhvwn. Rheum uitduUitum: Kneiiia iiusirosidineiisis: Rumex hueephcdophonis Pinostilbene or 3-methox\rcs\cratrol (/;Y//(.s-5.4'-dihydroxy-3-inethoxystilbene) 50 Rumex hueephidopliorus 7"/Y»;.s-3.4'-dinietlioxy-5-h\droxystilbcnc'' Knema austrosiamensis 48. 49 C'(.v-3.5.3'-trihydroxy-4'-inclhoxystilbcnc'' 51 Trimcthyircsveratrol (/yY//;.v-3.5.4'-trimethoxystilbcne)" Piero/ohiuni hexapetaUum 8. 26. 52 Gnetuclcistol D or 2-mctliox\oxyrcsveratrol 29 (//Y//;.v-2-mcthoxy-3'.4,5-trih\droxysti]benc) Gnetum eleistostaehyum Gnetuclcistol E or 3-methoxyisorhapontigenin 29 (//Y//;i-3.3'-dimcthoxy-5.4'-dihydroxystilbene) Gnetum eleistostaehyum Trans- and (7'.v-3.5.4'-trimcthoxy-3'-hydroxystilbene'' 51 Trans- and (•/.v-3,5.3'-trimethoxy-4'-hydroxystilbene" 51 Trans- and (;'/.v-3.5-diniethoxy-3'.4'-dihydroxystilbene'' 51 Trans- and (•/.v-3.5-dihydrox_\'-3'-amino-4'-methoxystilbene'' 51 Trans- and (7'.v-3.5-dimctlioxy-4'-aminostilbenc'' 51 Trans- and r/.v-3,4',5-trimcthoxy-3'-aniinostilbene'' 51 Trans- and (•/.v-3,5-dimclhoxy-4'-nitrosti!bcnc'' 51 Trans- and (•/.v-3.4',5-trimclhoxy-3'-nitrostilbcnc" 51 r/Y»7.y-5.4'-dihydroxy-3-mcthoxystilbcnc Rumex hiicephalophorus 51 Pterostilbene (/n/;;,v-3.5-dimcthoxy-4'-hydroxystilbcnc)'' 8. 51. 53. 54 Draeena eoehiinhinensis: Pleroearpus spp. (including P santalinus. P marsupium): Vitis vim'fera: Pterolohhim hexapetcilhim r/.v-3.5-dimethoxy-4'-h\droxystilbcnc'' 51 3.4.5.4'-tctramcthoxystilbcnc'' 26 3.4.5.3'-tctramcthoxystilbcnc'' 26 3.4.5.3'.4'-pcntamcthox\stilbcnc"' 26 7";Y//;.v-3.4.3'.5'-tctramcthox\slilbcnc Crotahuia nui(hirensis '^5 Sources and Chemistry of Resveratrol 21 TABLE 2.1 Continued Compound and sources Ref. Trails- and (:/.v-3.3'.5.5'-tetrahydroxy-4-methoxystilbene Yucca pcriculosa. 56-60 Y. schidiiicra: Cassia pudihwula T'(v//).v-4.4'-dihydroxystilbene Yucca pcriculosa 56 Trans-J-liy(lro\y-5-ine!h()xys!ilhcih' Cryplocarya iilcnhuri^cnsis 59 7"/Y//;.v-4.,V-dihydroxy-5'-methoxystilbene Dracaena loureiri 60 7'j7(/;.s-4-li\droxy-3'.5'-dimethoxystilbenc Dracaena loureiri. D. cochinchinensis 60. 61 Piccid or po!\'datin or resNeratrol-3-glucoside 2. 6. 62, 63 (»7;/;.v-3.5.4'-trihydroxystilbene-3-0-P-D-glucopyranosidc) Polygonum ctispidaUiin: Rlwuni rhaponlicuiu: Picea spp.: lentils (Lens culinaris) Rhapontin or rhaponticin 2. 6 (/n/«.v-3.3'.5-irihydroxy-4'-methoxystilbene-3-0-P-D-glucopyranosidc) Rlu'uni spp.: eucalyptus Deoxyrhapontin (/r(//;.v-3.5-dihydroxy-4'-methoxystilbcnc-3-0-(3-D-giucopyrano- 6 side) Rheum rhapoiuicum Isorhapontin (nY/;(.v-3.4'.5-trihydroxy-3'-mcthoxystilbene-3-0-p-r)-glucopyrano- 6. 62 side) Pin us sihiricu: Picea spp. Piceatannol glucoside (3.5.3',4'-tctrahydroxystilbene-4'-0-P-D-glucopyranoside) 2. 6 Rheum rhapontieum: Polygonum cuspidatum: spruce Pinostilbenosidc (r/v/;(.v-3-methoxy-5-h\droxystilbene-4'-0-P-r)-glucopyranoside) 64 Pinus koraieiisis Resveralroloside or resveratrol-4'-glucopyranosidc 2, 6. 3. 65 (rc(//;.v-3.5.4'-trihydroxystilbene-4'-0-P-D-glucopyranoside) Polrgoiuim cuspidalum: Pinus spp.; I'ifis vinijera Astringin (//Y;//.v-3,4,3'.5'-tetrahydroxystilbene-3'-0-P-D-glucopyranoside) 3. 62. 65 Picea spp.; Vilis vinijera Piceid-2"-0-ga]late and -2"-0-coumarate Pleuropierus ciliinerYis 66 Rhaponticin-2"-0-gallate and -6"-0-gallale Rhubarb {Rheum undulatum) 67 Piceatannol-6"-0-gallate Chinese rhubarb (Rhei rhizoma) 68 C/.v-rcsveratrol-3.4'-C-P-diglucoside
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