(0.27 g, 1 mmol) was added to dichloromethane (5 ml) and stirred to dissolve. A 1 mol/L solution of BBr3 in dichloromethane (10 ml) was added dropwise, and the reaction was stirred at room temperature for 2 h, and the reaction was followed by TLC [developing solvent: acetone-hexane (1:2)]. The reaction mixture was poured into EtOAc (EtOAc m. Recrystallization from 50% ethanol gave white crystals (1) (0.20 g, 90%), mp 256 to 257.

[Pharmacological action] (1) Anti-tumor effect
(2) treatment of cardiovascular disease
(3) Antioxidant and anti-free radical action
(4) Liver protection
(5) estrogen-like effects and affect bone metabolism
(6) Regulating immunity
(7) Anti-virus
(8) Anti-bacteria and fungi
(9) Anti-allergic reaction
(10) Radiation protection
(11) Prevention of acute infectious atypical pneumonia
[Use] Widely used in medicine, health care products, cosmetics and food additives

【references】
[1] Resveratrol: A Review http://www.pewiki.net/resveratrol/
[2] Bowers JL, Tyulmenkov VV, Jernigan SC, Klinge CM. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. Endocrinology. 2000; 141:3657-3667.
[3] Burkitt MJ, Duncan J. Effects of trans-resveratrol on copper-dependent hydroxyl-radical formation and DNA damage: Evidence for hydroxyl-radical scavenging and a novel. Glutathione-sparing mechanism of action. Arch Biochem Biophys. 2000; 381:253-263.
[4] Cao G, Prior RL. Red wine in moderation: Potential health benefits independent of alcohol. Nutr Clin Care. 2000; 3:76-82.
[5] Chun YJ, Kim MY, Guengerich FP. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem Biophys Res Commun. 1999; 262:20-24.
[6] Cichewicz RH, Kouzi SA, Hamann MT. Dimerization of resveratrol by the grapevine pathogen. Botrytis cinerea. J Natl Prod. 2000; 63:29-33.
[7] Ciolino HP, Yeh GC. Inhibition of aryl hydrocarbon-induced cytochrome P450 1A1 enzyme activity and CYP1A1 expression by resveratrol. Mol Pharmacol. 1999; 56:760-767.
[8] Doherty JJ, Fu MM, Stiffer BS, et al. Resveratrol inhibition of herpes simplex virus replication. Antiviral Res. 1999; 43:145-155.
[9] Dubash BD, Zheng BL, Kim CH, et al. Inhibitory effect of resveratrol and related compounds on the macromolecular synthesis in HL-60 cells and the metabolism of 7,12-dimethylbenz[a]anthracene by mouse liver microsomes. In: Shahidi F, Ho C-T, eds. Phytochemicals and Phytopharmaceuticals. Champaign, IL: AOCS Press; 2000:314-320.
[10] Fontecave M, Lepoivre M, Elleingand E, et al. Resveratrol, a remarkable inhibitor of ribonucleotide reductase. FEBS Lett. 1998; 421:277-279.
[11] Frémont L. Biological effects of resveratrol. Life Sci. 2000; 66:663-673.
[12] Frémont L, Belguendouz L, Delpal S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci. 1999; 64:2511-2521.
[13] Gehm BD, McAndrews JM, Chien P-Y, Jameson JL. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci USA. 1997; 94:14138-14143.
[14] Holmes-McNary M, Baldwin AS Jr. Chemopreventive properties of trans-resveratrol are associated with inhibition of activation of the IkappaB kinase. Cancer Res. 2000; 60:3477-3483.
[15] Hsieh TC, Juan G, Darzynkiewicz Z, Wu JM. Resveratrol increases nitric oxide synthase, induces accumulation of p53 and p21 (WAF1/CIP1), and suppresses cultured bovine pulmonary artery endothelial cell proliferation by perturbing progression through S and G2. Cancer Res. 1999; 59:2596-2601.
[16] Hung L-M, Chen J-K, Huang S-S, et al. Cardioprotective effect of resveratrol, a natural antioxidant derived from grapes. Cardiovascular Res. 2000; 47:549-555.
[17] Jang M, Cai L, Udeani GO, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science. 1997; 275:218-220.
[18] Jang M, Pezzuto JM. Cancer chemopreventive activity of resveratrol. Drugs Exp Clin Res. 1999; 25:65-77.
[19] Kirk RI, Deitch JA, Wu JM, Lerea KM. Resveratrol decreases early signaling events in washed platelets but has little effect on platelet aggregation in whole blood. Blood Cells Mol Dis. 2000; 26:144-150.
[20] Martinez J, Moreno JJ. Effect of resveratrol, a natural polyphenolic compound, on reactive oxygen species and prostaglandin production. Biochem Pharmacol. 2000; 59:865-870.
[21] Nielsen M, Ruch RJ, Vang O. Resveratrol reverses tumor-promoter-induced inhibition of gap-junctional intercellular communication. Biochem Biophys Res Commun. 2000; 275:804-809.
[22] Pace-Asciak CR, Hahn S, Diamandis EP, et al. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin Chim Acta. 1995; 235:207-219.
[23] Paul B, Masih I, Deopujari J, Charpentier C. Occurrence of resveratrol and pterostilbene in age-old darakchasava, an ayurvedic medicine from India. J Ethnopharmacol. 1999; 68:71-76.
[24] Pinto MC, García-Barrado JA, Macías P. Resveratrol is a potent inhibitor of the dioxygenase activity of lipoxygenase. J Agric Food Chem. 1999; 47:4842-4846.
[25] Ray PS, Maulik G, Cordis GA, et al. The red wine antioxidant resveratrol protects isolated rat hearts from ischemia reperfusion injury. Free Rad Biol Med. 1999; 27:160-169.
[26] Sanders TH, McMichael RW Jr, Hendrix KW. Occurrence of resveratrol in edible peanuts. J Agric Food Chem. 2000; 48:1243-1246.
[27] Schneider Y, Vincent F, Duranton B, et al. Anti-proliferative effect of resveratrol, a natural component of grapes and wine, on human colonic cancer cells. Cancer Lett. 2000; 158:85-91.
[28] Soleas GJ, Diamandis EP, Goldberg DM. Resveratrol: A molecule whose time has come? And gone? Clin Biochem. 1997; 30:91-113.
[29] Stewart JR, Christman KL, O’Brian CA. Effects of resveratrol on the autophosphorylation of phorbol ester-responsive protein kinases. Biochem Pharmacol. 2000; 60:1355-1359.
[30] Subbaramaiah K, Chung WJ, Michaluart P, et al. Resveratrol inhibits cyclooxygenase-2 transcription and activity in phorbol ester-treated human mammary epithelial cells. J Biol Chem. 1998; 273:21875-21882.
[31] Subbaramaiah K, Michaluart P, Chung WJ, et al. Resveratrol inhibits cyclooxygenase-2 transcription in human mammary epithelial cells. Ann NY Acad Sci. 2000; 889:214-223.
[32] Tang W, Eisenbrand G. Chinese Drugs of Plant Origin. Berlin: Springer-Verlag; 1992; 787-791.
[33] Tessitore L, Davit A, Sarotto I, Caderni G. Resveratrol depresses the growth of colorectal aberrant crypt foci by affecting bax and p21CIP expression. Carcinogenesis. 2000; 21:1619-1622.
[34] Tomera JF. Current knowledge of the health benefits and disadvantages of wine consumption. Trends Food Sci Technol. 1999; 10:129-138.
[35] Tsai SH, Lin-Shiau SY, Lin JK. Suppression of nitric oxide synthase and the down-regulation of the activation of NFkappaB in macrophages by resveratrol. Br J Pharmacol. 1999; 126:673-680.
[36] Zou J, Huang Y, Chen Q, et al. Suppression of mitogenesis and regulation of cell cycle traverse by resveratrol in cultured smooth muscle cells. Int J Oncol. 1999; 15:647-651.