Obtaining resveratrol: From chemical synthesis to biotechnological production

Mini-Reviews in Organic Chemistry

Volumn 7, Issue 4, 2010, Pages 272-281

  Fan, Enguo ^a   Zhang, Kai ^b   Zhu, Mingzhao ^c   Wang, Qiang ^d  

^a UNIVERSITY OF FREIBURG   (Germany)

^b NANKAI UNIVERSITY   (China)

^c UNIVERSITY OF ARKANSAS   (United States)

^d CHONGQING UNIVERSITY OF EDUCATION   (China)

Author keywords

Bioavailability; Biotechnological production; Chemical synthesis; Plant extraction; Resveratrol; Structure activity relationship

Indexed keywords

BIOCHEMISTRY; BIOTECHNOLOGY; EXTRACTION; RESVERATROL;

BIOAVAILABILITY; BIOTECHNOLOGICAL PRODUCTION; CLASSICAL METHODS; LARGE SCALE PRODUCTIONS; NATURAL MATERIALS; PLANT EXTRACTION; PREPARATION METHOD; REGIONAL VARIATION; SEASONAL VARIATION; STRUCTURE-ACTIVITY RELATIONSHIPS;

SYNTHESIS (CHEMICAL);

EID: 77958194073     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019310792246454     Document Type: Article

References (148)

1. Sun, A.Y., Simonyi, A., Sun, G.Y. The French Paradox and beyond: neuroprotective effects of polyphenols. Free. Radic. Biol. Med., 2002, 32(4), 314-318.
2. Fulda, S. Regulation of apoptosis and cell survival by resveratrol. Mini-Rev. Org. Chem., 2010, 7(4), 262-266.
3. Pallàs, M., Junyent, F., Jimenez, A., Verdaguer, E., Camins, A. Resveratrol: a therapeutic approach to nuerodegenerative diseases and aging. Mini-Rev. Org. Chem., 2010, 7(4), 267-271.
4. Mamunur Rahman, M., Das, D. K. Effectiveness of resveratrol against cardiovascular disease. Mini-Rev. Org. Chem., 2010, 7(4), 256-261.
5. Fan, E., Zhang, L., Jiang, S., Bai, Y. Beneficial effects of resveratrol on atherosclerosis. J. Med. Food, 2008, 11(4), 610-614.
6. Fan, E., Jiang, S., Zhang, L., Bai, Y. Molecular mechanism of apoptosis induction by resveratrol, a natural cancer chemopreventive agent. Int. J. Vitam. Nutr. Res., 2008, 78(1), 3-8.
7. Shakibaei, M., Harikumar, K.B., Aggarwal, B.B. Resveratrol addiction: to die or not to die. Mol. Nutr. Food Res., 2009, 53(1), 115-128.
8. Pervaiz, S., Holme, AL. Resveratrol: its biologic targets and functional activity. Antioxid. Redox Signal., 2009, 11(11), 2851-2597.
9. Jeandet, P., Douillet-Breuil, A.C., Bessis, R., Debord, S., Sbaghi, M., Adrian, M. Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J. Agric. Food Chem., 2002, 50(10), 2731-2741.
10. Halls, C., Yu, O. Potential for metabolic engineering of resveratrol biosynthesis. Trends Biotechnol., 2008, 26(2), 77-81.
11. Donnez, D., Jeandet, P., Clément, C., Courot, E. Bioproduction of resveratrol and stilbene derivatives by plant cells and microorganisms. Trends Biotechnol., 2009, 27(12), 706-713.
12. Artés-Hernández, F., Artés, F., Tomás-Barberán, F.A. Quality and enhancement of bioactive phenolics in cv. Napoleon table grapes exposed to different postharvest gaseous treatments. J. Agric. Food Chem., 2003, 51(18), 5290-5295.
13. Iriti, M., Rossoni, M., Borgo, M., Faoro, F. Benzothiadiazole enhances resveratrol and anthocyanin biosynthesis in grapevine, meanwhile improving resistance to Botrytis cinerea. J. Agric. Food Chem., 2004, 52(14), 4406-4413.
14. Tassoni, A., Fornalè, S., Franceschetti, M., Musiani, F., Michael, A.J., Perry, B., Bagni, N. Jasmonates and Na-orthovanadate promote resveratrol production in Vitis vinifera cv. Barbera cell cultures. New Phytol., 2005, 166(3), 895-905.
15. Rudolf, J.R., Resurreccion, A.V. Elicitation of resveratrol in peanut kernels by application of abiotic stresses. J. Agric. Food Chem., 2005, 53(26), 10186-10192.
16. González-Barrio, R., Beltrán, D., Cantos, E., Gil, M.I., Espín, J.C., Tomás-Barberán, F.A. Comparison of ozone and UV-C treatments on the postharvest stilbenoid monomer, dimer, and trimer induction in var. 'Superior' white table grapes. J. Agric. Food Chem., 2006, 54(12), 4222-4228.
17. Trela, B.C., Waterhouse, A. L. Resveratrol: isomeric molar absorptivities and stability. J. Agric. Food Chem., 1996, 44(5), 1253-1257.
18. Fan, E., Zhang, K., Jiang, S., Yan, C., Bai, Y. Analysis of trans-resveratrol in grapes by micro-high performance liquid chromatography. Anal. Sci., 2008, 24(8), 1019-1023.
19. Karacabey, E., Mazza, G. Optimization of solid-liquid extraction of resveratrol and other phenolic compounds from milled grape canes (Vitis vinifera). J. Agric. Food Chem., 2008, 56 (15), 6318-6325.
20. Bais, A.J., Murphy, P.J., Dry, I.B. The molecular regulation of stilbene phytoalexin biosynthesis in Vitis vinifera during grape berry development. Aust. J. Plant Physiol., 2000, 27(5), 425-433.
21. Chung, I.-M., Park, M.R., Chun, J.C., Yun, S.J. Resveratrol accumulation and resveratrol synthase gene expression in response to abiotic stresses and hormones in peanut plants. Plant Sci., 2003, 164(7), 103-109.
22. Beňová, B., Adam, M., Pavlíková, P., Fischer, J. Supercritical fluid extraction of piceid, resveratrol and emodin from Japanese knotweed. J. Supercrit. Fluids, 2010, 51(3), 325-330.
23. Piñeiro, Z., Palma, M., Barroso, C.G. Determination of trans-resveratrol in grapes by pressurised liquid extraction and fast high-performance liquid chromatography. J. Chromatogr. A, 2006, 1110(1-2), 61-65.
24. Yang, F., Zhang, T., Ito, Y. Large-scale separation of resveratrol, anthraglycoside A and anthraglycoside B from Polygonum cuspidatum Sieb. et Zucc by high-speed counter-current chromatography. J. Chromatogr. A, 2001, 919(2), 443-448.
25. Zhang, D., Li, X., Hao, D., Li, G., Xu, B., Ma, G., Su, Z. Systematic purification of polydatin, resveratrol and anthraglycoside B from Polygonum cuspidatum Sieb. et Zucc. Sep. Purif. Technol., 2009, 66(2), 329-339.
26. Sun, B., Ribes, A.M., Leandro, M.C., Belchior, A.P., Spranger, M.I. Stilbenes: Quantitative extraction from grape skins, contribution of grape solids to wine and variation during wine maturation. Anal. Chim. Acta, 2006, 563(1-2), 382-390.
27. Nerantizis, T.E., Tataridis, P. Integrated enology-utilization of winery by-products into high added value products. E. J. Sci. Technol. (e-Jst), 2006, 1(3), 179-189.
28. Späth, E., Kromp, K. Über die Inhaltsstoffe des roten Sandelholzes. III. Mitteil.: Die Synthese des Pterostilbens. Chem. Ber., 1941, 74(2), 189-192.
29. Takaoka, M. The phenolic substances of white hellebore (Veratrum grandiflorum Loes. fil.). J. Chem. Soc. Jpn., 1939, 60, 1261-1264.
30. Takaoka, M. Phenolic substances of white hellebore (Veratrum grandiflorum Loes. fil.). J. Fac. Sci. Hokkaido Imp. Univ., 1940, 3, 1-16.
31. Solladié, G., Jacopé, Y.P., Maignan, J. A re-investigation of resveratrol synthesis of perkins reaction. application to the synthesis of aryl cinnamic acids. Tetrahedron, 2003, 59(18), 3315-3321.
32. Sinha, A.K., Kumar, V., Sharma, A., Sharma, A., Kumar R. An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction. Tetrahedron, 2007, 63(45), 11070-11077.
33. Chandrasekhar, S., Karri, P. Revised mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride. Tetrahedron Lett., 2006, 47(13), 2249-2251.
34. Moreno-Manas, M., Pleixatas, R. Dehydroacetic acid chemistry. A new synthesis of resveratrol, a photoalexine of Vitis Vinifera. Anal. Quim., 1985, 81, 157-161.
35. Jeandet, P., Bessis, R., Gautheron, B. The production of reseveratrol 3,5,4′-trihydroxystilbene by grape berries in different developmental stages. Am. J. Enol. Vitic., 1991, 42(1), 41-46.
36. Goldberg, D.M., Yan, J., Ng, E., Diamandis, E.P., Karumanchiri, A., Soleas, G., Waterhouse, A.L. Direct injection gas chromatographic mass spectrometric assay for trans-resveratrol. Anal. Chem., 1994, 66(22), 3959-3963.
37. Orsini, F., Pelizzoni, F., Bellini, B., Miglierini, G. Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series). Carbohydr. Res., 1997, 301(3-4), 95-109.
38. Alonso, F., Riente, P., Yus, M. Wittig-type olefination of alcohols promoted by nickel nanoparticles: synthesis of polymethoxylated and polyhydroxylated stilbenes. Eur. J. Org. Chem., 2009, 2009(34), 6034-6042.
39. Alonso, F., Riente, P., Yus, M. Synthesis of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles. Tetrahedron Lett., 2009, 50(25), 3070-3073.
40. 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.
41. Clarke, S.D., Harrison, C.R., Hodge, P. Phase transfer catalysed polymer-supported Wittig reactions. Tetrahedron Lett., 1980, 21(14), 1375-1378.
42. Bellucci, G., Chiappe, C., Moro, G.L. Crown ether catalyzed stereospecific synthesis of Z- and E-Stilbenes by Wittig reaction I a solid-liquid two-phases system. Tetrahedron Lett., 1996, 37(24), 4225-4228.
43. Ferré-Filmon, K., Delaude, L., Demonceau, A., Noels, A.F. Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins. Coord. Chem. Rev., 2004, 248(21-24), 2323-2336.
44. Cushman, M., Nagarathnam, D., Gopal, D., He, H.-M., Lin, C. M., Hamel, E. Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5 trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents. J. Med. Chem., 1992, 35(12), 2293-2306.
45. Alli, M.A., Tsuda, Y. New method for isomerization of (Z)-Stilbenes into the (E)-Isomers catalyzed by diaryl disulfide. Chem. Pharm. Bull., 1992, 40(10), 2842-2844.
46. Wang, Q., EI Khoury, M., Schlosser, M. Bridging the final gap in stereocontrolled wittig reactions: methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity. Chemistry, 2000, 6(3), 420-426.
47. Maryanoff, B.E., Reitz, A.B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev., 1989, 89(4), 863-927.
48. Lion, C.J., Matthews, C.S., Stevens, M.F.G., Westwell, A.D. Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes. J. Med. Chem., 2005, 48(4), 1292-1295.
49. Heynekamp, J.J., Weber, W.M., Hunsaker, L.A., Gonzales, A.M., Orlando, R.A., Deck, L.M., Jagt, D.L. Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor kappaB. J. Med. Chem., 2006, 49(24), 7182-7189.
50. Dakdouki, S.C., Villemin, D., Bar, N. Solid-Phase reactive chromatography (SPRC): A new methodology for Wittig and Horner-Emmons reactions on a column under microwave irradiation. Eur. J. Org. Chem., 2010, 2010(2), 333-337.
51. Guiso, M., Marra, C., Farina, A. A new efficient resveratrol synthesis. Tetrahedron Lett., 2002, 43(4), 597-598.
52. Farina, A., Ferranti, C., Marra, C. An improved synthesis of resveratrol. Nat. Prod. Res., 2006, 20(3), 247-252.
53. 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.
54. Jeffery, T., Ferber, B. One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol. Tetrahedron Lett., 2003, 44(1), 193-197.
55. Moro, A.V., Cardoso, F.S.P., Correia, C.R.D. 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.
56. Iijima, T., Makabe, H. Short-step synthesis of a resveratrol derivative from commercially available 1,3-dimethoxybenzene and 4-vinylanisole. Biosci. Biotechnol. Biochem., 2009, 73(11), 2547-2548.
57. Alonso, E., Ramón, D.J., Yus, M. Simple synthesis of 5-substituted resorcinols: a revisited family of interesting bioactive molecules. J. Org. Chem., 1997, 62(2), 417-421.
58. Aïssa, C. Mechanistic manifold and new developments of the Julia-Kocienski reaction. Eur. J. Org. Chem., 2009, 2009(12), 1831-1844.
59. Alonso, D.A., Nájera, C., Varea, M. 3,5-Bis(trifluoromethyl)phenyl sulfones in the modified Julia olefination: application to the synthesis of resveratrol. Tetrahedron Lett., 2004, 45(3), 573-577.
60. Alonso, D. A., Fuensanta, M., Nájera, C., Varea, M. 3,5-Bis(trifluoromethyl) phenyl Sulfones in the Direct Julia-Kocienski Olefination. J. Org. Chem., 2005, 70(16), 6404-6416.
61. Likhtenshtein, G. Stilbenes: Applications in Chemistry. WILEY-VCH Verlag GmbH & Co. KGaA: Weinheim, 2009.
62. Delaunois, B., Cordelier, S., Conreux, A., Clément, C., Jeandet, P. Molecular engineering of resveratrol in plants. Plant Biotechnol. J., 2009, 7(1), 2-12.
63. Watts, K.T., Lee, P.C., Schmidt-Dannert, C. Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. BMC Biotechnol., 2006, 6, 22.
64. Beekwilder, J., Wolswinkel, R., Jonker, H., Hall, R., de Vos, C. H., Bovy, A. Production of resveratrol in recombinant microorganisms. Appl. Environ. Microbiol., 2006, 72(8), 5670-5672.
65. Huang, L.L., Xue, Z., Zhu, Q.Q. Method for the production of resveratrol in a recombinant bacterial host cell. U.S. Patent 20070031951 A1, February 08, 2007.
66. Katsuyama, Y., Funa, N., Horinouchi, S. Precursor-directed biosynthesis of stilbene methyl ethers in Escherichia coli. Biotechnol. J., 2007, 2(10), 1286-1293.
67. Katsuyama, Y., Funa, N., Miyahisa, I., Horinouchi, S. Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli. Chem. Biol., 2007, 14(6), 613-621.
68. Huang, L.L., Xue, Z., Zhu, Q.Q. Method for the production of resveratrol in a recombinant oleaginous microorganism U.S. patent PCT/US2006/019085, May 17, 2006.
69. Katz, M., Smits, H.P., Förster, J., Nielsen, J.B. Metabolically engineered cells for the production of resveratrol or an oligomeric or glycosidically-bound derivative thereof. EU patent EP20060708430, November 21, 2007.
70. Trantas, E., Panopoulos, N., Ververidis, F. Metabolic engineering of the complete pathway leading to heterologous biosynthesis of various flavonoids and stilbenoids in Saccharomyces cerevisiae. Metab. Eng., 2009, 11(6), 355-366.
71. Zhang, Y., Li, S.Z., Li, J., Pan, X., Cahoon, R.E., Jaworski, J.G., Wang, X., Jez, J.M., Chen, F., Yu, O. Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and mammalian cells. J. Am. Chem. Soc., 2006, 128(40), 13030-13031.
72. Becker, J.V., Armstrong, G.O., van der Merwe, M.J., Lambrechts, M.G., Vivier, M.A., Pretorius, I.S. Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol. FEMS Yeast Res., 2003, 4(1), 79-85.
73. Aziz, N.H., Farag, S.E., Mousa, L.A., Abo-Zaid, M.A. Comparative antibacterial and antifungal effects of some phenolic compounds. Microbios., 1998, 93(374), 43-54.
74. Gonzalez-Candelas, L., Gil, J.V., Lamuela-Raventos, R.M., Ramon, D. The use of transgenic yeasts expressing a gene encoding a glycosyl-hydrolase as a tool to increase resveratrol content in wine. Int. J. Food Microbiol., 2000, 59(3), 179-183.
75. Todaro, A., Palmeri, R., Barbagallo, R.N., Pifferi, P.G., Spagna, G. Increase of trans-resveratrol in typical Sicilian wine using β-Glucosidase from various sources. Food Chem., 2008, 107(4), 1570-1575.
76. Pretorius, I.S., Bauer., F.F. Meeting the consumer challenge through genetically customized wine-yeast strains. Trends Biotechnol., 2002, 20(10), 426-432.
77. Hanhineva, K., Kokko, H., Siljanen, H., Rogachev, I., Aharoni, A., Kärenlampi, S.O. Stilbene synthase gene transfer caused alterations in the phenylpropanoid metabolism of transgenic strawberry (Fragaria x ananassa). J. Exp. Bot., 2009, 60(7), 2093-2106.
78. Kobayashi, S., Ding, C.K., Nakamura, Y., Nakajima, I., Matsumoto, R. Kiwifruits (Actinidia deliciosa) transformed with a Vitis stilbene synthase gene produce piceid (resveratrol-glucoside). Plant Cell Rep., 2000, 19(9), 904-910.
79. Schulze, K., Schreiber, L., Szankowski, I. Inhibiting effects of resveratrol and its glucoside piceid against Venturia inaequalis, the causal agent of apple scab. J. Agric. Food Chem., 2005, 53(2), 356-362.
80. Jaillon, O., Aury, J.M., Noel, B., Policriti, A., Clepet, C., Casagrande, A., Choisne, N., Aubourg, S., Vitulo, N., Jubin, C., Vezzi, A., Legeai, F., Hugueney, P., Dasilva, C., Horner, D., Mica, E., Jublot, D., Poulain, J., Bruyère, C., Billault, A., Segurens, B., Gouyvenoux, M., Ugarte, E., Cattonaro, F., Anthouard, V., Vico, V., Del Fabbro, C., Alaux, M., Di Gaspero, G., Dumas, V., Felice, N., Paillard, S., Juman, I., Moroldo, M., Scalabrin, S., Canaguier, A., Le Clainche, I., Malacrida, G., Durand, E., Pesole, G., Laucou, V., Chatelet, P., Merdinoglu, D., Delledonne, M., Pezzotti, M., Lecharny, A., Scarpelli, C., Artiguenave, F., Pè, M.E., Valle, G., Morgante, M., Caboche, M., Adam-Blondon, A.F., Weissenbach, J., Quétier, F., Wincker, P., French-Italian Public Consortium for Grapevine Genome Characterization. The grapevine genome sequence suggests ancestral hexaploidization in major angiosperm phyla. Nature, 2007, 449(7161), 463-467.
81. Serazetdinova, L., Oldach, K.H., Lörz, H. Expression of transgenic stilbene synthases in wheat causes the accumulation of unknown stilbene derivatives with antifungal activity. J. Plant Physiol., 2005, 162(9), 985-1002.
82. Wiese, W., Vornam, B., Krause, E., Kindl, H. Structural organization and differential expression of three stilbene synthase genes located on a 13 kb grapevine DNA fragment. Plant Mol. Biol., 1994, 26(2), 667-677.
83. Rühmann, S., Treutter, D., Fritsche, S., Briviba, K., Szankowski, I. Piceid (resveratrol glucoside) synthesis in stilbene synthase transgenic apple fruit. J. Agric. Food Chem., 2006, 54(13), 4633-4640.
84. Richter, A., Jacobsen, H.J., De Kathen, A., De Lorenzo, G., Briviba, K., Hain, R., Ramsay, G., Kiesecker, H. Transgenic peas (Pisum sativum) expressing polygalacturonase inhibiting protein from raspberry (Rubus idaeus) and stilbene synthase from grape (Vitis vinifera). Plant Cell Rep., 2006, 25(11), 1166-1173.
85. Kovárová, M., Bartůnková, K., Frantík, T., Koblihová, H., Prchalová, K., Vosátka, M. Factors influencing the production of stilbenes by the knotweed, Reynoutria xbohemica. BMC Plant Biol., 2010, 10(1), 19.
86. Gatto, P., Vrhovsek, U., Muth, J., Segala, C., Romualdi, C., Fontana, P., Pruefer, D., Stefanini, M., Moser, C., Mattivi, F., Velasco, R. Ripening and genotype control stilbene accumulation in healthy grapes. J. Agric. Food Chem., 2008, 56(24), 11773-11785.
87. Lim, J.D., Yun, S.J., Chung, I.M., Yu, C.Y. Resveratrol synthase transgene expression and accumulation of resveratrol glycoside in Rehmannia glutinosa. Mol. Breeding, 2005, 16(3), 219-233.
88. Smetanska, I. Production of secondary metabolites using plant cell cultures. Adv. Biochem. Eng. Biotechnol., 2008, 111, 187-228.
89. Kouakou, T.H., Téguo, P.W., Valls, J., Kouadio, Y.J., Decendit, A., Mérillon, J.-M. First evidence of trans-resveratrol production in cell suspension cultures of cotton (Gossypium hirsutum L.). Plant Cell Tissue Org. Cult., 2006, 86(3), 405-409.
90. Bru, R., Sellés, S., Casado-Vela, J., Belchí-Navarro, S., Pedreño, M.A. Modified cyclodextrins are chemically defined glucan inducers of defense responses in grapevine cell cultures. J. Agric. Food Chem., 2006, 54(1), 65-71.
91. Lijavetzky, D., Almagro, L., Belchi-Navarro, S., Martínez-Zapater, J.M., Bru, R., Pedreño, M.A. Synergistic effect of methyljasmonate and cyclodextrin on stilbene biosynthesis pathway gene expression and resveratrol production in Monastrell grapevine cell cultures. BMC Res. Notes, 2008, 22(1), 132.
92. Ferri, M., Tassoni, A., Franceschetti, M., Righetti, L., Naldrett, M.J., Bagni, N. Chitosan treatment induces changes of protein expression profile and stilbene distribution in Vitis vinifera cell suspensions. Proteomics, 2009, 9(3), 610-624.
93. Zamboni, A., Gatto, P., Cestaro, A., Pilati, S., Viola, R., Mattivi, F., Moser, C., Velasco, R. Grapevine cell early activation of specific responses to DIMEB, a resveratrol elicitor. BMC Genomics, 2009, 10, 363.
94. Saigne-Soulard, C., Richard, T., Mérillon, J.M., Monti, J.P. 13C NMR analysis of polyphenol biosynthesis in grape cells: Impact of various inducing factors. Anal. Chim. Acta, 2006, 563(1-2), 137-144.
95. Lucas-Abellán, C., Fortea, I., López-Nicolás, J.M., Núñez-Delicado, E. Cyclodextrins as resveratrol carrier system. Food Chem., 2007, 104(1), 39-44.
96. Regev-Shoshani, G., Shoseyov, O., Bilkis, I., Kerem, Z. Glycosylation of resveratrol protects it from enzymic oxidation. Biochem. J., 2003, 374(Pt 1), 157-163.
97. Yazaki, K., Sugiyama, A., Morita, M., Shitan, N. Secondary transport as an efficient membrane transport mechanism for plant secondary metabolites. Phytochem. Rev., 2008, 7(3), 513-524.
98. Medina-Bolivar, F., Condori, J., Rimando, A.M., Hubstenberger, J., Shelton, K., O'Keefe, S. F., Bennett, S., Dolan, M. C. Production and secretion of resveratrol in hairy root cultures of peanut. Phytochemistry, 2007, 68(14), 1992-2003.
99. Kim, J.S., Lee, S.K., Park, S.U. Resveratrol production in hairy root culture of peanut, Arachis hypogaea L. transformed with different Agrobacterium rhizogenes strains. Afr. J. Biotechnol., 2008, 7(20), 3788-3790.
100. Condori, J., Sivakumar, G., Hubstenberger, J., Dolan, M.C., Sobolev, V.S., Medina-Bolivar, F. Induced biosynthesis of resveratrol and the prenylated stilbenoids arachidin-1 and arachidin-3 in hairy root cultures of peanut: Effects of culture medium and growth stage. Plant Physiol. Biochem., 2010, doi:10.1016/j.plaphy.2010.01.008.
101. Georgiev, M.I., Pavlov, A.I., Bley, T. Hairy root type plant in vitro systems as sources of bioactive substances. Appl. Microbiol. Biot., 2007, 74(6), 1175-1185.
102. Ku, K.L., Chang, P.S., Cheng, Y.C., Lien, C.Y. Production of stilbenoids from the callus of Arachis hypogaea: a novel source of the anticancer compound piceatannol. J. Agric. Food Chem., 2005, 53(10), 3877-3881.
103. Kiselev, K.V., Dubrovina, A.S., Veselova, M.V., Bulgakov, V.P., Fedoreyev, S.A., Zhuravlev, Y.N. The rolB gene-induced overproduction of resveratrol in Vitis amurensis transformed cells. J. Biotechnol., 2007, 128(3), 681-692.
104. Keskin, N., Kunter, B. Production of trans-resveratrol in 'Cabernet Sauvignon' (Vitis vinifera L.) callus culture in response to ultraviolet-C irradiation. Vitis, 2008, 47(4), 193-196.
105. Ho, C.W., Kuo H.S. In vitro resveratrol rich callus tissues derived from Vitis thunbergii Sieb. et Zucc. and method for producing the same. U.S. Patent 20080160560, March 07, 2008.
106. Dubrovina, A.S., Kiselev, K.V., Veselova, M.V., Isaeva, G.A., Fedoreyev, S.A., Zhuravlev, Y.N. Enhanced resveratrol accumulation in rolB transgenic cultures of Vitis amurensis correlates with unusual changes in CDPK gene expression. J. Plant Physiol., 2009, 166(11), 1194-1206.
107. Kiselev, K.V., Dubrovina, A.S., Bulgakov, V.P. Phenylalanine ammonia-lyase and stilbene synthase gene expression in rolB transgenic cell cultures of Vitis amurensis. Appl. Microbiol. Biotechnol., 2009, 82(4), 647-655.
108. Baur JA, Sinclair, D.A. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov., 2006, 5(6), 493-506.
109. Watve, M.G., Tickoo, R., Jog, M.M., Bhole, B.D. How many antibiotics are produced by the genus Streptomyces? Arch. Microbiol., 2001, 176(5), 386-390.
110. Park, S.R., Yoon, J.A., Paik, J.H., Park, J.W., Jung, W.S., Ban, Y.H., Kim, E.J., Yoo, Y.J., Han, A.R., Yoon, Y.J. Engineering of plant-specific phenylpropanoids biosynthesis in Streptomyces venezuelae. J. Biotechnol., 2009, 141(3-4), 181-188.
111. Fan, E., Zhang, K., Yao, C., Yan, C., Bai, Y., Jiang, S. Determination of trans-resveratrol in China Great Wall "Fazenda" red wine by use of micellar electrokinetic chromatography. Chromatographia, 2005, 62(5-6), 289-294.
112. Kolouchova-Hanzlikova, I., Melzoch, K., Filip, V., Šmidrkal, J. Rapid method for resveratrol determination by HPLC with electrochemical and UV detections in wines. Food Chem., 2004, 87(1), 151-158.
113. López-Hernández, J., Paseiro-Losada, P., Sanches-Silva, A.T., Lage-Yusty, M.A. Study of the changes of trans -resveratrol caused by ultraviolet light and determination of trans- and cis-resveratrol in Spanish white wines. Eur. Food Res. Technol., 2007, 225(5-6), 789-796.
114. Montsko, G., Nikfardjam, M.S.P., Szabo, Z., Boddi, K., Lorand, T., Ohmacht, R., Mark L. Determination of products derived from trans-resveratrol UV photoisomerisation by means of HPLC-APCI-MS. J. Photochem. Photobiol., A 2008, 196(1), 44-50.
115. Wenzel, E., Somoza, V. Metabolism and bioavailability of trans-resveratrol. Mol. Nutr. Food Res., 2005, 49(5), 472-481.
116. Juan, M.E., González-Pons, E., Planas, J.M. Multidrug resistance proteins restrain the intestinal absorption of trans-resveratrol in rats. J. Nutr., 2010, 140(3), 489-495.
117. Soleas, G.J., Angelini, M., Grass, L., Diamandis, E.P., Goldberg, D.M. Absorption of trans-resveratrol in rats. Methods Enzymol., 2001, 335, 145-154.
118. Vitrac, X., Desmouliere, A., Brouillaud, B., Krisa, S., Deffieux, G., Barthe, N., Rosenbaum, J., Mérillon, J.M. Distribution of [14C]trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration. Life Sci., 2003, 72(20), 2219-2233.
119. Yu, C., Shin, Y.G., Chow, A., Li, Y. Human, rat and mouse metabolism of resveratrol. Pharm. Res., 2002, 19(12), 1907-1914.
120. Sale, S., Verschoyle, R.D., Boocock, D., Jones, D.J.L. Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans-3,4,5,49-tetramethoxystilbene. Br. J. Cancer, 2004, 90(3), 736-744.
121. Jannin, B., Menzel, M., Berlot, J.P., Delmas, D., Lançon, A., Latruffe, N. Transport of resveratrol, a cancer chemopreventive agent, to cellular targets: plasmatic protein binding and cell uptake. Biochem. Pharmacol., 2004, 68(6), 1113-1138.
122. 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.
123. Lee, S.K., Zhang, W., Sanderson, B.J. Selective growth inhibition of human leukemia and human lymphoblastoid cells by resveratrol via cell cycle arrest and apoptosis induction. J. Agric. Food Chem., 2008, 56(16), 7572-7577.
124. Shu, X.H., Li, H., Sun, Z., Wu, M.L., Ma, J.X., Wang, J.M., Wang, Q., Sun, Y., Fu, Y.S., Chen, X.Y., Kong, Q.Y., Liu, J. Identification of metabolic pattern and bioactive form of resveratrol in human medulloblastoma cells. Biochem. Pharmacol., 2010, 79(10), 1516-1525.
125. Stopper, H., Schmitt, E., Kobras, K. Genotoxicity of phytoestrogens. Mutat. Res., 2005, 574(1-2), 139-155.
126. Del Nero, J., P. De Melo, C. Investigation of the excited states of resveratrol and related molecules. Int. J. Quantum Chem., 2003, 95, 213-218.
127. Erkoc, S., Keskin, N., Erkoc, F. Resveratrol and its analogues resveratrol-dihydroxyl isomers: semi-empirical SCF-MO calculations. Theor. Chem., 2003, 631(1-3), 67-73.
128. Cao, H., Pan, X., Li, C., Zhou, C., Deng, F., Li, T. Density functional theory calculations for resveratrol. Biol. Med. Chem. Lett., 2003, 13(11), 1869-1871.
129. Caruso, F., Tanski, J., Villegas-Estrada, A., Rossi, M. Structural basis for antioxidant activity of trans-resveratrol: ab initio calculations and crystal and molecular structure. J. Agric. Food Chem., 2004, 52(24), 7279-7285.
130. Stivala, L.A., Savio, M., Carafoli, F., Perucca, P., Bianchi, L., Maga, G., Forti, L., Pagnoni, U.M., Albini, A., Prosperi, E., Vannini, V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem., 2001, 276(25), 22586-22594.
131. Matsuoka, A., Takeshita, K., Furuta, A., Ozaki, M., Fukuhara, K., Miyata, N. The 4'-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol. Mutat. Res., 2002, 521(1-2), 29-35.
132. Brede, O., Stojanovic, S., Sprinz, H. Antioxidant action of transresveratrol and its analogues in the radiation-induced liposome oxidation. Free Radic. Res., 2002, 36(Suppl. 1), 76-77.
133. Murias, M., Jäger, W., Handler, N., Erker, T., Horvath, Z., Szekeres, T., Nohl, H., Gille, L. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem. Pharmacol., 2005, 69(6), 903-912.
134. Fukuhara, K., Nakanishi, I., Matsuoka, A., Matsumura, T., Honda, S., Hayashi, M., Ozawa, T., Miyata, N., Saito, S., Ikota, N., Okuda, H. Effect of methyl substitution on the antioxidative property and genotoxicity of resveratrol. Chem. Res. Toxicol., 2008, 21(2), 282-287.
135. Murias, M., Handler, N., Erker, T., Pleban, K., Ecker, G., Saiko, P., Szekeres, T., Jäger, W. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem., 2004, 12(21), 5571-5578.
136. Ovesna, Z., Horváthová-Kozics, K. Structure-activity relationship of trans-resveratrol and its analogues. Neoplasma 2005, 52(6), 450-455.
137. Shang, Y.J., Qian, Y.P., Liu, X.D., Dai, F., Shang, X.L., Jia, W.Q., Liu, Q., Fang, J.G., Zhou, B. Radical-scavenging activity and mechanism of resveratrol-oriented analogues: influence of the solvent, radical, and substitution. J. Org. Chem., 2009, 74(14), 5025-5031.
138. Rüweler, M., Gülden, M., Maser, E., Murias, M., Seibert, H. Cytotoxic, cytoprotective and antioxidant activities of resveratrol and analogues in C6 astroglioma cells in vitro. Chem. Biol. Interact., 2009, 182(2-3), 128-135.
139. Cardile, V., Chillemi, R., Lombardo, L., Sciuto, S., Spatafora, C., Tringali, C. Antiproliferative activity of methylated analogues of E-and Z-resveratrol. Z. Naturforsch. C, 2007, 62(3-4), 189-195.
140. Roberti, M., Pizzirani, D., Simoni, D., Rondanin, R., Baruchello, R., Bonora, C., Buscemi, F., Grimaudo, S., Tolomeo, M. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem., 2003, 46(16), 3546-3554.
141. Lee, S.K., Nam, K.A., Hoe, Y.H., Min, H.Y., Kim, E.Y., Ko, H., Song, S., Lee, T., Kim, S. Synthesis and evaluation of cytotoxicity of stilbene analogues. Arch. Pharm. Res., 2003, 26(4), 253-257.
142. Chemler, J.A., Koffas, M.A. Metabolic engineering for plant natural product biosynthesis in microbes. Curr. Opin. Biotechnol., 2008, 19(6), 597-605.
143. Fecik, R.A. Natural product biosynthesis moves in vitro. Nat. Chem. Biol., 2007, 3(9), 531-532.
144. Cheng, Q., Xiang, L., Izumikawa, M., Meluzzi, D., Moore, B.S. Enzymatic total synthesis of enterocin polyketides. Nat. Chem. Biol., 2007, 3(9),557-558.
145. Balibar, C.J., Howard-Jones, A.R., Walsh, C.T. Terrequinone A biosynthesis through L-tryptophan oxidation, dimerization and bisprenylation. Nat. Chem. Biol., 2007, 3(9), 584-592
146. Gescher, A.J., Steward, W.P. Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: a conundrum. Cancer Epidemiol. Biomarkers Prev., 2003, 12(10), 953-957.
147. Fan, E., Zhang, K. Targeting resveratrol to mitochondria for cardiovascular diseases. Recent Pat. Cardiovasc. Drug Discov., 2010, 5(2), 97-102.
148. Jeffery, E.H., Keck, A.S. Translating knowledge generated by epidemiological and in vitro studies into dietary cancer prevention. Mol. Nutr. Food Res., 2008, 52(Suppl 1), S7-17.