A Mini Review on the Chemical Synthesis of Resveratrol

Author(s): Hong Huang, Ruonan Liu, Wenhua Ou*

Journal Name: Mini-Reviews in Organic Chemistry

Volume 17 , Issue 5 , 2020

DOI : 10.2174/1570193X16666190617155558

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Graphical Abstract:


Abstract:

Resveratrol is a polyphenolic compound and has been shown to possess numerous biological activities, which could possibly be applied to the prevention and/or treatment of cancer, cardiovascular disease, and neurodegenerative diseases. This review summarizes the progress of different chemical methods in the preparation of resveratrol.

Keywords: Chemical synthesis, demethylation, heck reaction process, perkin reaction process, resveratrol, wittig-reaction process.

[1]
Burns, J.; Yokota, T.; Ashihara, H.; Lean, M.E.; Crozier, A. Plant foods and herbal sources of resveratrol. J. Agric. Food Chem., 2002, 50(11), 3337-3340.
[http://dx.doi.org/10.1021/jf0112973] [PMID: 12010007]
[2]
Rimando, A.M.; Kalt, W.; Magee, J.B.; Dewey, J.; Ballington, J.R. Resveratrol, pterostilbene, and piceatannol in vaccinium berries. J. Agric. Food Chem., 2004, 52(15), 4713-4719.
[http://dx.doi.org/10.1021/jf040095e] [PMID: 15264904]
[3]
Sanders, T.H.; McMichael, R.W., Jr.; Hendrix, K.W. Occurrence of resveratrol in edible peanuts. J. Agric. Food Chem., 2000, 48(4), 1243-1246.
[http://dx.doi.org/10.1021/jf990737b] [PMID: 10775379]
[4]
Hurst, W.J.; Glinski, J.A.; Miller, K.B.; Apgar, J.; Davey, M.H.; Stuart, D.A. Survey of the trans-resveratrol and trans-piceid content of cocoa-containing and chocolate products. J. Agric. Food Chem., 2008, 56(18), 8374-8378.
[http://dx.doi.org/10.1021/jf801297w] [PMID: 18759443]
[5]
Frémont, L. Biological effects of resveratrol. Life Sci., 2000, 66(8), 663-673.
[http://dx.doi.org/10.1016/S0024-3205(99)00410-5] [PMID: 10680575]
[6]
Bavaresco, L.; Fregoni, C.; Cantù, E.; Trevisan, M. Stilbene compounds: From the grapevine to wine. Drugs Exp. Clin. Res., 1999, 25(2-3), 57-63.
[PMID: 10370866]
[7]
Jasiński, M.; Jasińska, L.; Ogrodowczyk, M.; Jasińska, O. Resveratrol in prostate diseases - a short review. Cent. European J. Urol., 2013, 66(2), 144-149.
[PMID: 24579014]
[8]
(a) Colman, J. A commentary on resveratrol. Med. Aromat. Plants,2015, 4(4), 1-1. bEctor, B.J.; Magee, J.; Hegwood, C.P.; Coign, M.J. Resveratrol concentration in Muscadine berries, juice, pomace, purees, seeds, and wines. Am. J. Enol. Vitic.,1996, 47(1), 57-62. (c) Jeandet, P.; Bessis, R. The production of resveratrol by grape berries in different developmental stages. Am. J. Enol. Vitic.,1991, 42(1), 41-46. (d) Sun, B.; Ribes, A.M.; Leandro, M.C.; Belchior, A.P.; Spranger, M.I. Quantitative extraction from grape skins, contribution of grape solids to wine and variation during wine maturation. Anal. Chim. Acta, 2006, 563, 382-390.
[9]
Aggarwal, B.B.; Bhardwaj, A.; Aggarwal, R.S.; Seeram, N.P.; Shishodia, S.; Takada, Y. Role of resveratrol in prevention and therapy of cancer: Preclinical and clinical studies. Anticancer Res., 2004, 24(5A), 2783-2840.
[PMID: 15517885]
[10]
Romero-Pérez, A.I.; Ibern-Gómez, M.; Lamuela-Raventós, R.M.; de La Torre-Boronat, M.C. Piceid, the major resveratrol derivative in grape juices. J. Agric. Food Chem., 1999, 47(4), 1533-1536.
[http://dx.doi.org/10.1021/jf981024g] [PMID: 10564012]
[11]
Siemann, E.H.; Creasey, L.L. Concentration of the phytoalexin resveratrol in wine. Am. J. Enol. Vitic., 1992, 43(1), 49-52.
[12]
Renaud, S.; de Lorgeril, M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet, 1992, 339(8808), 1523-1526.
[http://dx.doi.org/10.1016/0140-6736(92)91277-F] [PMID: 1351198]
[13]
Vidavalur, R.; Otani, H.; Singal, P.K.; Maulik, N. Significance of wine and resveratrol in cardiovascular disease: French paradox revisited. Exp. Clin. Cardiol., 2006, 11(3), 217-225.
[PMID: 18651034]
[14]
Baell, J.; Walters, M.A. Chemistry: Chemical con artists foil drug discovery. Nature, 2014, 513(7519), 481-483.
[http://dx.doi.org/10.1038/513481a] [PMID: 25254460]
[15]
Walle, T.; Hsieh, F.; DeLegge, M.H.; Oatis, J.E., Jr; Walle, U.K. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos., 2004, 32(12), 1377-1382.
[http://dx.doi.org/10.1124/dmd.104.000885] [PMID: 15333514]
[16]
Ingólfsson, H.I.; Thakur, P.; Herold, K.F.; Hobart, E.A.; Ramsey, N.B.; Periole, X.; de Jong, D.H.; Zwama, M.; Yilmaz, D.; Hall, K.; Maretzky, T.; Hemmings, H.C., Jr; Blobel, C.; Marrink, S.J.; Koçer, A.; Sack, J.T.; Andersen, O.S. Phytochemicals perturb membranes and promiscuously alter protein function. ACS Chem. Biol., 2014, 9(8), 1788-1798.
[http://dx.doi.org/10.1021/cb500086e] [PMID: 24901212]
[17]
Vang, O. Resveratrol: challenges in analyzing its biological effects. Ann. N. Y. Acad. Sci., 2015, 1348(1), 161-170.
[http://dx.doi.org/10.1111/nyas.12879] [PMID: 26315294]
[18]
de Santi, C.; Pietrabissa, A.; Mosca, F.; Pacifici, G.M. Glucuronidation of resveratrol, a natural product present in grape and wine, in the human liver. Xenobiotica, 2000, 30(11), 1047-1054.
[http://dx.doi.org/10.1080/00498250010002487] [PMID: 11197066]
[19]
Alcaín, F.J.; Villalba, J.M. Sirtuin activators. Expert Opin. Ther. Pat., 2009, 19(4), 403-414.
[http://dx.doi.org/10.1517/13543770902762893] [PMID: 19441923]
[20]
De Santi, C.; Pietrabissa, A.; Spisni, R.; Mosca, F.; Pacifici, G.M. Sulphation of resveratrol, a natural product present in grapes and wine, in the human liver and duodenum. Xenobiotica, 2000, 30(6), 609-617.
[http://dx.doi.org/10.1080/004982500406435] [PMID: 10923862]
[21]
Beher, D.; Wu, J.; Cumine, S.; Kim, K.W.; Lu, S.C.; Atangan, L.; Wang, M. Resveratrol is not a direct activator of SIRT1 enzyme activity. Chem. Biol. Drug Des., 2009, 74(6), 619-624.
[http://dx.doi.org/10.1111/j.1747-0285.2009.00901.x] [PMID: 19843076]
[22]
De Santi, C.; Pietrabissa, A.; Spisni, R.; Mosca, F.; Pacifici, G.M. Sulphation of resveratrol, a natural compound present in wine, and its inhibition by natural flavonoids. Xenobiotica, 2000, 30(9), 857-866.
[http://dx.doi.org/10.1080/004982500433282] [PMID: 11055264]
[23]
Pacholec, M.; Bleasdale, J.E.; Chrunyk, B.; Cunningham, D.; Flynn, D.; Garofalo, R.S.; Griffith, D.; Griffor, M.; Loulakis, P.; Pabst, B.; Qiu, X.; Stockman, B.; Thanabal, V.; Varghese, A.; Ward, J.; Withka, J.; Ahn, K. SRT1720, SRT2183, SRT1460, and resveratrol are not direct activators of SIRT1. J. Biol. Chem., 2010, 285(11), 8340-8351.
[http://dx.doi.org/10.1074/jbc.M109.088682] [PMID: 20061378]
[24]
Boocock, D.J.; Faust, G.E.; Patel, K.R.; Schinas, A.M.; Brown, V.A.; Ducharme, M.P.; Booth, T.D.; Crowell, J.A.; Perloff, M.; Gescher, A.J.; Steward, W.P.; Brenner, D.E. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol. Biomarkers Prev., 2007, 16(6), 1246-1252.
[http://dx.doi.org/10.1158/1055-9965.EPI-07-0022] [PMID: 17548692]
[25]
Lagouge, M.; Argmann, C.; Gerhart-Hines, Z.; Meziane, H.; Lerin, C.; Daussin, F.; Messadeq, N.; Milne, J.; Lambert, P.; Elliott, P.; Geny, B.; Laakso, M.; Puigserver, P.; Auwerx, J. Resveratrol improves mitochondrial function and protects against metabolic disease by activating SIRT1 and PGC-1alpha. Cell, 2006, 127(6), 1109-1122.
[http://dx.doi.org/10.1016/j.cell.2006.11.013] [PMID: 17112576]
[26]
Almeida, L.; Vaz-da-Silva, M.; Falcão, A.; Soares, E.; Costa, R.; Loureiro, A.I.; Fernandes-Lopes, C.; Rocha, J.F.; Nunes, T.; Wright, L.; Soares-da-Silva, P. Pharmacokinetic and safety profile of trans-resveratrol in a rising multiple-dose study in healthy volunteers. Mol. Nutr. Food Res., 2009, 53(Suppl. 1), S7-S15.
[http://dx.doi.org/10.1002/mnfr.200800177] [PMID: 19194969]
[27]
Macmillan-Crow, L.A.; Cruthirds, D.L. Invited review: Manganese superoxide dismutase in disease. Free Radic. Res., 2001, 34(4), 325-336.
[http://dx.doi.org/10.1080/10715760100300281] [PMID: 11328670]
[28]
Goldberg, D.M.; Yan, J.; Soleas, G.J. Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin. Biochem., 2003, 36(1), 79-87.
[http://dx.doi.org/10.1016/S0009-9120(02)00397-1] [PMID: 12554065]
[29]
Prossnitz, E.R.; Barton, M. Estrogen biology: New insights into GPER function and clinical opportunities. Mol. Cell. Endocrinol., 2014, 389(1-2), 71-83.
[http://dx.doi.org/10.1016/j.mce.2014.02.002] [PMID: 24530924]
[30]
Vaz-da-Silva, M.; Loureiro, A.I.; Falcao, A.; Nunes, T.; Rocha, J.F.; Fernandes-Lopes, C.; Soares, E.; Wright, L.; Almeida, L.; Soares-da-Silva, P. Effect of food on the pharmacokinetic profile of trans-resveratrol. Int. J. Clin. Pharmacol. Ther., 2008, 46(11), 564-570.
[http://dx.doi.org/10.5414/CPP46564] [PMID: 19000554]
[31]
Wang, L.; Waltenberger, B.; Pferschy-Wenzig, E.M.; Blunder, M.; Liu, X.; Malainer, C.; Blazevic, T.; Schwaiger, S.; Rollinger, J.M.; Heiss, E.H.; Schuster, D.; Kopp, B.; Bauer, R.; Stuppner, H.; Dirsch, V.M.; Atanasov, A.G. Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): A review. Biochem. Pharmacol., 2014, 92(1), 73-89.
[http://dx.doi.org/10.1016/j.bcp.2014.07.018] [PMID: 25083916]
[32]
Vercauteren, J. Compositions of stilbenic polyphenolic derivatives, their preparation, and their use in the treatment of disease and aging. W.O. Patent 2009/063. 2009.
[33]
Sharan, S.; Nagar, S. Pulmonary metabolism of resveratrol: in vitro and in vivo evidence. Drug Metab. Dispos., 2013, 41(5), 1163-1169.
[http://dx.doi.org/10.1124/dmd.113.051326] [PMID: 23474649]
[34]
Kelly, G. A review of the sirtuin system, its clinical implications, and the potential role of dietary activators like resveratrol: Part 1. Altern. Med. Rev., 2010, 15(3), 245-263.
[PMID: 21155626]
[35]
Ragazzi, E.; Froldi, G.; Fassina, G. Resveratrol activity on guinea pig isolated trachea from normal and albumin-sensitized animals. Pharmacol. Res. Commun., 1988, 20(Suppl. 5), 79-82.
[http://dx.doi.org/10.1016/S0031-6989(88)80846-4] [PMID: 2907791]
[36]
Bertelli, A.; Bertelli, A.A.; Gozzini, A.; Giovannini, L. Plasma and tissue resveratrol concentrations and pharmacological activity. Drugs Exp. Clin. Res., 1998, 24(3), 133-138.
[PMID: 9825229]
[37]
Shah, A.; Reyes, L.M.; Morton, J.S.; Fung, D.; Schneider, J.; Davidge, S.T. Effect of resveratrol on metabolic and cardiovascular function in male and female adult offspring exposed to prenatal hypoxia and a high-fat diet. J. Physiol., 2016, 594(5), 1465-1482.
[http://dx.doi.org/10.1113/JP271133] [PMID: 26467260]
[38]
Moreno-Manas, M.; Pleixats, R. Dehydroacetic acid chemistry. A new synthesis of resveratrol, a phytoalexine of Vitis vinifera. Anal. Quim., 1985, 81, 157-161.
[39]
Ali, M.A.; Kondo, K.; Tsuda, Y. Synthesis and nematocidal activity of hydroxystilbenes. Chem. Pharm. Bull. (Tokyo), 1992, 40(5), 1130-1136.
[http://dx.doi.org/10.1248/cpb.40.1130]
[40]
Li, X.G.; Wang, S.Y.; Li, C.R.; Li, S.X. Study on the Synthesis of Resveratrol. China Food Addit., 2002, 5, 25-27.
[41]
Zhuo, G.L.; Shen, Z.L.; Jiang, X.Z. Total synthesis of natural product E-reservatrol. Zhongguo Yaowu Huaxue Zazhi, 2002, 12(3), 152-154.
[42]
Wang, F.S.; Hu, W.B.; Song, X.J.; Xiang, J.G.; Deng, S.M.; Feng, F. Method for synthesis of trans-resveratrol via combined hydroxy- protection method. C.N. Patent 102,079,691. 2011.
[43]
Andrus, M.; Meredith, E. Synthesis of resveratrol. W.O. Patent 2001/060,774. 2001.
[44]
Kim, S.; Ko, H.; Park, J.E.; Jung, S.; Lee, S.K.; Chun, Y.J. Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J. Med. Chem., 2002, 45(1), 160-164.
[http://dx.doi.org/10.1021/jm010298j] [PMID: 11754588]
[45]
Wang, Z.Y.; Ma, Z.J.; Li, Q.; Shen, Z. Synthesis of resveratrol. Carol. J. Pharm., 2003, 34(9), 428-429.
[46]
Liu, P.; Li, J.J.; Cheng, M.S. Improved synthesis of resveratrol. Zhongguo Yaowu Huaxue Zazhi, 2008, 18(6), 424-425.
[47]
Bai, D.H. Synthesis of natural product Resveratrol. J. Tianjin Normal Univ. (Nat. Sci. Ed.), 2006, 26(1), 17-19.
[48]
Li, W.; Li, Z.Q. Process for the preparation of trans-resveratrol. C.N. Patent 103,570,508. 2014.
[49]
Jungong, C.S.; Novikov, A.V. Practical preparation of resveratrol 3-o-β-d-glucuronide. Synth. Commun., 2012, 42(24), 3589-3597.
[http://dx.doi.org/10.1080/00397911.2011.585733] [PMID: 22919115]
[50]
Hou, J.; Wang, G.P.; Zhou, Q. Synthesis of resveratrol. Carol. J. Pharm., 2008, 39(1), 1-8.
[51]
Mi, Q.X.; Zeng, D.L. Simple and high-efficiency method for synthesis of trans-resveratrol. C.N. Patent 101,585,751. 2009.
[52]
Li, Y.Q.; Li, Z.L.; Zhao, W.J.; Wen, R.X.; Meng, Q.W.; Zeng, Y. Synthesis of stilbene derivatives with inhibition of SARS coronavirus replication. Eur. J. Med. Chem., 2006, 41(9), 1084-1089.
[http://dx.doi.org/10.1016/j.ejmech.2006.03.024] [PMID: 16875760]
[53]
Yoshiaki, T.; Kenji, T.; Junko, I.; Yue-Hua, H.; Maki, T.; Naho, Y.; Masatake, N. Biomimic transformation of resveratrol. Tetrahedron, 2005, 61(43), 10285-10295.
[http://dx.doi.org/10.1016/j.tet.2005.08.023]
[54]
Moon, H.I.; Chung, I.M.; Jung, J.C.; Lim, E.; Lee, Y.; Oh, S.; Jung, M. The convenient synthesis and evaluation of the anticancer activities of new resveratrol derivatives. J. Enzyme Inhib. Med. Chem., 2009, 24(2), 328-336.
[http://dx.doi.org/10.1080/14756360802185731] [PMID: 18608762]
[55]
Pan, H.J.; Shai, X.Y.; Wang, C.J.; Wei, Y.Y. Total Synthesis of Resveratrol. Chin. J. Synthetic Chem., 2008, 16(2), 170-172.
[56]
Francisco, A.; Paola, R.; Miguel, Y. Synthesis of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles. Tetrahedron Lett., 2009, 50(25), 3070-3073.
[http://dx.doi.org/10.1016/j.tetlet.2009.04.023]
[57]
McNulty, J.; Das, P. Highly Stereoselective and general synthesis of (E)-stilbenes and alkenes by means of an aqueous Wittig reaction. Eur. J. Org. Chem., 2009, (24), 4031-4035.
[http://dx.doi.org/10.1002/ejoc.200900634]
[58]
Drahl, C. In names, history and legacy-chemistry and culture collide in the coining of namesake reactions. Chem. Eng. News, 2010, 88(22), 31-33.
[http://dx.doi.org/10.1021/cen-v088n020.p031]
[59]
Heck, R.F.; Nolley, J.P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem., 1972, 37(14), 2320-2322.
[http://dx.doi.org/10.1021/jo00979a024]
[60]
Mizoroki, T.; Mori, K.; Ozaki, A. Arylation of olefin with aryl iodide catalyzed by palladium. Bull. Chem. Soc. Jpn., 1971, 44(2), 581-581.
[http://dx.doi.org/10.1246/bcsj.44.581]
[61]
Guiso, M.; Marra, C.; Farina, A. A new efficient resveratrol synthesis. Tetrahedron Lett., 2002, 43(4), 597-598.
[http://dx.doi.org/10.1016/S0040-4039(01)02227-4]
[62]
Farina, A.; Ferranti, C.; Marra, C. An improved synthesis of resveratrol. Nat. Prod. Res., 2006, 20(3), 247-252.
[http://dx.doi.org/10.1080/14786410500059532] [PMID: 16401555]
[63]
Farina, A.; Ferranti, C.; Marra, C.; Guiso, M.; Norcia, G. Synthesis of hydroxystilbenes and their derivatives via Heck reaction. Nat. Prod. Res., 2007, 21(6), 564-573.
[http://dx.doi.org/10.1080/14786410701195291] [PMID: 17497428]
[64]
Csuk, R.; Albert, S.; Kluge, R.; Ströhl, D. Resveratrol derived butyrylcholinesterase inhibitors. Arch. Pharm. (Weinheim), 2013, 346(7), 499-503.
[http://dx.doi.org/10.1002/ardp.201300051] [PMID: 23722618]
[65]
Andrus, M.B.; Liu, J.; Meredith, E.L.; Nartey, E. Synthesis of resveratrol using a direct decarbonylative Heck approach from resorcylic acid. Tetrahedron Lett., 2003, 44(26), 4819-4822.
[http://dx.doi.org/10.1016/S0040-4039(03)01131-6]
[66]
Yan, Z.J. A process for preparing resveratrol by using Heck reaction. C.N. Patent 102,976,938. 2013.
[67]
Liu, Y.; Liu, W. Process for preparation of resveratrol. C.N. Patent 102,276,426. 2011.
[68]
Andrus, M.B.; Liu, J. Sirtuin activating compounds and methods for making the same. US Patent 771,416,1B2. 2008.
[69]
Liu, M.Y.; Li, Z.Q. Method for preparing resveratrol and its derivatives by decarbonylative Heck reaction. C.N. Patent 102,050,705. 2011.
[70]
Myers, A.G.; Tanaka, D.; Mannion, M.R. Development of a decarboxylative palladation reaction and its use in a Heck-type olefination of arene carboxylates. J. Am. Chem. Soc., 2002, 124(38), 11250-11251.
[http://dx.doi.org/10.1021/ja027523m] [PMID: 12236722]
[71]
Andrus, M.B.; Liu, J. Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative heck couplings. Tetrahedron Lett., 2006, 47(32), 5811-5814.
[http://dx.doi.org/10.1016/j.tetlet.2006.05.065]
[72]
Venturin Moro, A.; Pereira Cardoso, F.S.; Duarte Correia, C.R. Heck arylation of styrenes with arenediazonium salts: Short, efficient, and stereoselective synthesis of resveratrol, DMU-212, and analogues. Tetrahedron Lett., 2008, 49(39), 5668-5671.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.087]
[73]
Schmidt, B.; Elizarov, N.; Berger, R.; Hölter, F. Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes. Org. Biomol. Chem., 2013, 11(22), 3674-3691.
[http://dx.doi.org/10.1039/c3ob40420j] [PMID: 23615777]
[74]
Perkin, W.H. On the artificial production of coumarin and formation of its homologues. J. Chem. Soc., 1868, 21, 53-63.
[http://dx.doi.org/10.1039/JS8682100053]
[75]
Perkin, W.H. On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues. J. Chem. Soc., 1877, 32, 660-674.
[http://dx.doi.org/10.1039/JS8773200660]
[76]
Dippy, J.F.J.; Evans, R.M. The nature of the catalyst in the Perkin condensation. J. Org. Chem., 1950, 15(3), 451-456.
[http://dx.doi.org/10.1021/jo01149a001]
[77]
Spath, E.; Kurt Kromp, K. About the ingredients of red sandalwood. III. Mitteil. The synthesis of pterostilbene. Chem. Ber., 1941, 74(2), 189-192.
[http://dx.doi.org/10.1002/cber.19410740204]
[78]
Ao, G.Z.; Hou, P.B.; Cao, Y.; Yang, S.W.; Feng, J.J. Method for preparation of (E)-Resveratrol. C.N. Patent 102,180,773. 2011.
[79]
Li, G.X.; Zou, Y.; Zhang, X.J. An efficient synthesis of resveratrol and a hydroxyl derivative via the Perkin reaction: cis to trans isomerisation in a demethylation process. J. Chem. Res., 2007, (11), 657-659.
[80]
Zou, Y.; Li, G.X.; Zhang, X.J.; Wei, W.; Lin, H.Z. Process for preparation of trans polyhydroxy diphenyl ethylene compounds. C.N. Patent 101,066,912. 2007.
[81]
Zhu, Y.S.; Luo, S.N.; Shen, Y.J.; Yu, H.X.; Chen, B.; Zhang, L.G. Synthesis of resveratrol analogues. Youji Huaxue, 2006, 26(7), 958-962.
[82]
Wang, Z.X.; Zhnag, X.J.; Zhou, Y.; Zou, Y. A convenient synthesis of trans- and cis-3,4′,5-trihydroxystilbene. J. Chin. Pharm. Sci., 2005, 14(4), 204-208.
[83]
Du, J.L.; Zou, Y.; Xiao, C.F. A convenient method for synthesis of resveratrol. Fine Chem., 2009, 26(6), 580-584.
[84]
Xiao, C.F.; Zou, Y.; Du, J. Li.; Sun, H.Y.; Liu, X.K. Hydroxyl substitutional effect on selective synthesis of cis, trans stilbenes and 3-arylcoumarins through perkin condensation. Synth. Commun., 2012, 42(9), 1243-125.
[http://dx.doi.org/10.1080/00397911.2010.538889]
[85]
Gan, L. Improved method for synthesizing resveratrol. C.N. Patent 101,875,600. 2010.
[86]
Zou, Y.; Xiao, C.F.; Chen, Y.; Wei, W.; Sun, H.Y.; Lu, Z.L. A process for preparing stilbene derivatives. C.N. Patent 101,774,894. 2010.
[87]
Sinha, A.K.; Sharma, A.; Kumar, V. Single step microwave induced process for the preparation of substituted stilbenes and analogs. U.S. Patent 2007/276,172. 2007.
[88]
Zou, Y.; Du, J.L.; Xiao, C.F. Process for preparation of polyhydroxy substituted transstil-benes. C.N. Patent 101,481,300. 2009.
[89]
Solladiéa, G.; Pasturel-Jacopéa, Y.; Maignanb, J. A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids. Tetrahedron, 2003, 59(18), 3315-3321.
[http://dx.doi.org/10.1016/S0040-4020(03)00405-8]
[90]
Pettit, G.R.; Grealish, M.P.; Jung, M.K.; Hamel, E.; Pettit, R.K.; Chapuis, J.C.; Schmidt, J.M. Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate. J. Med. Chem., 2002, 45(12), 2534-2542.
[http://dx.doi.org/10.1021/jm010119y] [PMID: 12036362]
[91]
Zou, Y.; Huang, Q.; Huang, T.K.; Ni, Q.C.; Zhang, E.S.; Xu, T.L.; Yuan, M.; Li, J. CuI/1,10-phen/PEG promoted decarboxylation of 2,3-diarylacrylic acids: Synthesis of stilbenes under neutral and microwave conditions with an in situ generated recyclable catalyst. Org. Biomol. Chem., 2013, 11(40), 6967-6974.
[http://dx.doi.org/10.1039/c3ob41588k] [PMID: 24057265]
[92]
Liu, C.H.; Xiang, L.J.; Wen, R.M.; You, P.Q. Synthesis of resveratrol. Carol. J. Pharm., 2012, 43(11), 893-895.
[93]
Peddikotla, P.; Chittiboyina, A.G.; Khan, I.A. Synthesis of pterostilbene by Julia Olefination. Synth. Commun., 2013, 43(23), 3217-3223.
[http://dx.doi.org/10.1080/00397911.2013.775308]
[94]
Wiffen, J.W.; Mccague, R. Process for the preparation of polyhydroxylated stilbenes via claisen condensation. E.P. Patent 1,884,508. 2006.
[95]
Wu, A.Q.; Shen, L.Q.; Wu, Z.H. Total synthesis of (E)-resveratrol. Shizhen Guoyi Guoyao, 2010, 21(1), 75-76.
[96]
Lai, Y.T.; Zhang, X.Q.; Gro, J.; Li, B.L. Synthesis of resveratrol analogues. Chem. Regents, 2007, 29(5), 257-259.
[97]
Zhu, Y.H. Method for preparing resveratrol and its analogs via composite metal oxide solid alkali catalysis. C.N. Patent 103,214,352. 2013.
[98]
Dorwal, H.N.; Sabapathy, S.M. Process for the preparation of polyhydroxystilbene compounds by deprotection of the corresponding ethers. U.S. Patent 2015/031,921. 2015.
[99]
Yan, R.A.; Lin, Y.X. Improved method for synthesis of resveratrol with aluminum trichloride as catalyst. C.N. Patent 102,050,704. 2011.
[100]
Vallejos, J.C.; Schouteeten, A.; Wilhelm, D. Process for the synthesis of polyhydroxystilbene compounds. W.O. Patent, WO/2009/043761. 2009.
[101]
Lappano, R.; Rosano, C.; Madeo, A.; Albanito, L.; Plastina, P.; Gabriele, B.; Forti, L.; Stivala, L.A.; Iacopetta, D.; Dolce, V.; Andò, S.; Pezzi, V.; Maggiolini, M. Structure-activity relationships of resveratrol and derivatives in breast cancer cells. Mol. Nutr. Food Res., 2009, 53(7), 845-858.
[http://dx.doi.org/10.1002/mnfr.200800331] [PMID: 19496085]
[102]
Kumar, V.; Sharma, A.; Sharma, A.; Sinha, A.K. Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: A clean synthesis of hydroxylated (E)-stilbenes. Tetrahedron, 2007, 63(32), 7640-7646.
[http://dx.doi.org/10.1016/j.tet.2007.05.046]
[103]
Ferré-Filmon, K.; Delaude, L.; Demonceau, A.; Noels, A.F. Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis. Eur. J. Org. Chem., 2005, (15), 3319-3325.
[http://dx.doi.org/10.1002/ejoc.200500068]


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Article Details

VOLUME: 17
ISSUE: 5
Year: 2020
Published on: 11 August, 2020
Page: [546 - 558]
Pages: 13
DOI: 10.2174/1570193X16666190617155558
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