A novel, convenient synthesis of the 3-O-β-D- and 4′-O-β -D-glucopyranosides of trans-resveratrol

Synthetic Communications

Volumn 34, Issue 9, 2004, Pages 1565-1575

  Learmonth, David A ^a  

^a DEPARTMENT OF RESEARCH AND DEVELOPMENT   (Portugal)

Author keywords

Glucosidation; Glucupyranoside; Heck reaction; Trans Resveratrol

Indexed keywords

GLUCOPYRANOSIDE; GLUCOSIDE; NATURAL PRODUCT; POLYPHENOL DERIVATIVE; RESVERATROL; RESVERATROL 3 O BETA DEXTRO GLUCOPYRANOSIDE; RESVERATROL 4' O BETA DEXTRO GLUCOPYRANOSIDE; SILBENOID; STILBENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATE; HECK REACTION; SANDMEYER REACTION; SYNTHESIS;

EID: 2442695248     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120030744     Document Type: Article

References (29)

1. Schultz, T.P.; Boldin, W.D.; Fisher, T.H.; Nicholas, D.D.; McMurtrey, K.D.; Pobanz, K. Structure-fungicidal properties of some 3- and 4-hydroxylated stilbenes and bibenzyl analogs. Phytochemistry 1992, 31 (11), 3801-3806.
2. Sobolev, V.S.; Cole, R.J.; Dorner, J.W.; Yagen, B.J. Isolation, purification and liquid chromatographic determination of stilbene phytoalexins in peanuts. AOAC Int. 1995, 78 (5), 1177-1182; Chem Abstr. 123, 337690.
3. Sobolev, V.S.; Cole, R.J.; Dorner, J.W.; Yagen, B.J. Isolation, purification and liquid chromatographic determination of stilbene phytoalexins in peanuts. AOAC Int. 1995, 78 (5), 1177-1182; Chem Abstr. 123, 337690.
4. Celott, E.; Ferrarini, R.; Zironi, R.; Conte, L.S. Resveratrol content of some wines obtained from dried Valpolicella grapes: Recioto and Amarone. J. Chromatogr. A 1996, 730, 47-52.
5. Pace-Asciak, C.R.; Hahm, S.; Diamandis, E.P.; Soleas, G.; Goldberg, D.M. The red wine phenolics trans-reservatrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin. Chim. Acta 1995, 235, 207-219.
6. Mannila, E.; Talvitie, A.; Kolehmainen, E. Antileukemic compounds derived from stilbenes in Picea abies bark. Phytochemistry 1993, 33, 813-816.
7. Langcake, P.; Cornford, C.A.; Pryce, R.J. Identification of pterostilbene as a phytoalexin from Vitis vinifera leaves. Phytochemistry 1979, 18, 1025-1027.
8. Chen, C.K.; Pace-Asciak, C.R. Vasorelaxing activity of resveratrol and quercetin in isolated rat aorta. Gen. Pharmacol. 1996, 27 (2), 363-366.
9. Kopp, P. Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the "French paradox"? Eur. J. Endocrinol. 1998, 138 (6), 619-620.
10. Das, D.K.; Sato, M.; Ray, P.S.; Maulik, G.; Engelman, R.M.; Bertelli, A.A.E.; Bertelli, A. Cardiprotection of red wine. Role of polyphenolic antioxidants. Drugs Exp. Clin. Res. 1999, 25 (2/3), 115-120.
11. Goldberg, D.M.; Ng, E.; Karamanchiri, A.; Yan, J.; Diamandis, E.P.; Soleas, G. Assay of resveratrol glucosides and isomers in wine by direct-injection high-performance liquid chromatography. J. Chromatogr. A 1995, 708, 89-98.
12. Orsini, F.; Pelizzoni, F.; Verotta, L.; Abarjai, T. Isolation, synthesis and antiplatelet aggregation activity of resveratrol 3-O-β -D-glucopyranoside and related compounds. J. Nat. Prod. 1997, 60, 1082-1087.
13. Kimura, Y.; Okuda, H. Effects of naturally occurring stilbene glucosides from medicinal plants and wine on tumour growth and lung metastasis in Lewis lung carcinoma-bearing mice. J. Pharm. Pharmacol. 2000, 52 (19), 1287-1295.
14. Chen, L.; Han, Y.; Yang, F.; Zhang, T. High-speed counter-current chromatography separation and purification of reservatrol and piceid from Polygonum cuspidatum. J. Chromatogr. A 2001, 907, 343-346.
15. Vastano, B.C.; Chen, Y.; Zhu, N.; Ho, C.; Zhou, Z.; Rosen, R.T. Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum. J. Agric. Food Chem. 2000, 48, 253-256.
16. Teguo, P.W.; Fauconneau, J.M.; Bernard, G.; Huguet, F.; Vercautern, J.; Merillon, J.M. Isolation, identification and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell cultures. J. Nat. Prod. 1998, 61 (5), 655-657.
17. Teguo, P.W.; Hawthorne, M.E.; Cuendet, M.; Merillon, J.M.; Kinghorn, A.D.; Pezzuto, J.M.; Mehta, R.G. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutrition and Cancer 2001, 40 (2), 173-179.
18. Jayatilake, G.S.; Jayasuriya, H.; Lee, E.S.; Koonchanok, N.M.; Geahlen, R.L.; Ashendel, C.L.; Chang, J.L.; Ching, J. Kinase inhibitors from Polygonum cuspidatum. J. Nat. Prod. 1993, 56 (10), 1805-1810.
19. Fan, W.; Tezuka, Y.; Kadota, S. Prolyl endopeptidase inhibitory activity of fourteen Kampo formulas and inhibitory constituents of Tokaku-jokito. Chem. Pharm. Bull. 2000, 48 (7), 1055-1061.
20. Guiso, M.; Marra, C.; Farina, A. A new efficient resveratrol synthesis. Tetrahedron Lett. 2002, 43, 597-598.
21. Chang, S.; Na, Y.; Shin, H.J.; Choi, E.; Jeong, L.S. A short and efficient synthetic approach to hydroxy (E)-stilbenoids via solid-phase cross metathetis. Tetrahedron Lett. 2002, 43, 7445-7448.
22. Shen, Z.L.; Zhuo, L.; Jiang, X.Z. A practical synthesis of trans-resveratrol. Indian J. Chem. Sect. B 2002, 41B (11), 2395-2398.
23. Polunin, K.E.; Schmalz, H.G.; Polunina, I.A. Chromium arene complexes in synthesis of trans-resveratrol. Russ. Chem. Bull. 2002, 51 (7), 1319-1324.
24. Jeffery, T.; Ferber, B. One-pot palladium catalysed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol. Tetrahedron Lett. 2003, 44, 193-197.
25. Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G. Synthesis of biologically active polyphenolic glycosides (combrestatin and resveratrol series). Carbohydr. Res. 1997, 301, 95-109.
26. Brandolini, V.; Maietti, A.; Tedeschi, P.; Durini, E.; Vertuani, S.; Manfredini, S. Capillary electrophoresis determination, synthesis and stability of resveratrol and related 3-O-β-D-glucopyranosides. J. Agric. Food Chem. 2002, 50, 7407-7411.
27. Learmonth, D.A. A concise synthesis of the 3-O-β-D- and 4′-O-β-D-glucuronide conjugates of trans-resveratrol. Bioconjugate Chem. 2003, 14, 262-267.
28. Deboves, H.J.C.; Montalbetti, C.A.G.N.; Jackson, R.F.W. Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids. J. Chem. Soc. Perkin Trans. 1 2001, 16, 1876-1884.
29. Trela, B.C.; Waterhouse, A.L. Resveratrol: isomeric molar absorptivities and stability. J. Agric. Food Chem. 1996, 44, 1253-1257.