Biological/chemopreventive activity of stilbenes and their effect on colon cancer

Planta Medica

Volumn 74, Issue 13, 2008, Pages 1635-1643

  Rimando, Agnes M ^a   Suh, Nanjoo ^b,c  

^a NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

^b RUTGERS UNIVERSITY   (United States)

^c RUTGERS CANCER INSTITUTE OF NEW JERSEY   (United States)

Author keywords

Colon cancer; Inflammation; Resveratrol; Stilbenes

Indexed keywords

ANTINEOPLASTIC AGENT; ASTRINGIN; DESOXYRHAPONTIGENIN; ISORHAPONTIGENIN; ISORHAPONTIN; OXYRESVERATROL; PICEATANNOL; PICEID; PINOSTILBENE; PINOSTILBENOSIDE; PINOSYLVIN; PINOSYLVIN MONOMETHYLETHER; PTEROSTILBENE; RESVERATROL; RESVERATROL TRIMETHYLETHER; RESVERATROLOSIDE; RHAPONTIGENIN; RHAPONTIN; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BIOLOGICAL ACTIVITY; CANCER INHIBITION; CANCER PREVENTION; COLON CANCER; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; HUMAN; NONHUMAN; REVIEW; SINGLE DRUG DOSE;

ANIMALS; ANTICARCINOGENIC AGENTS; COLONIC NEOPLASMS; DIET; FRUIT; HUMANS; MICE; STILBENES; VEGETABLES;

ANIMALIA; VITACEAE;

EID: 56249132708     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1088301     Document Type: Review

References (119)

1. Kelloff GJ, Lippman SM, Dannenberg AJ, Sigman CC et al. Progress in chemoprevention drug development: the promise of molecular biomarkers for prevention of intraepithelial neoplasia and cancer - a plan to move forward. Clin Cancer Res 2006; 12: 3661-97
2. Khanna D, Sethi G, Ahn KS, Pandey MK, Kunnumakkara AB, Sung B et al. Natural products as a gold mine for arthritis treatment. Curr Opin Pharmacol 2007; 7: 344-51
3. Gescher AJ. Resveratrol from red grapes - pedestrian polyphenol or useful anticancer agent? Planta Med 2008; 74: 1651-5
4. Garodia P, Ichikawa H, Malani N, Sethi G, Aggarwal BB. From ancient medicine to modern medicine: ayurvedic concepts of health and their role in inflammation and cancer. J Soc Integr Oncol 2007; 5: 25-37
5. Langcake P, Pryce RJ. A new class of phytoalexins from grapevines. Experientia 1977; 33: 151-2
6. Hart JH, Shrimpton DM. Role of stilbenes in resistance of wood to decay. Phytopathology 1979; 69: 1138-43
7. Baur JA, Pearson KJ, Price NL, Jamieson HA, Lerin C, Kalra A et al. Resveratrol improves health and survival of mice on a high-calorie diet. Nature 2006; 444: 337-42
8. Aggarwal BB, Shishodia S, Sandur SK, Pandey MK, Sethi G. Inflammation and cancer: how hot is the link? Biochem Pharmacol 2006; 72: 1605-21
9. Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y. Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Res 2004; 24: 2783-840
10. Baur JA, Sinclair DA. Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov 2006; 5: 493-506
11. Rimando AM, Kalt W, Magee JB, Dewey J, Ballington JR. Resveratrol, pterostilbene, and piceatannol in vaccinium berries. J Agric Food Chem 2004; 52: 4713-9
12. Ingham JL. 3,5,4′-Trihydroxystilbene as a phytoalexin from groundnuts (Arachis hypogaea). Phytochemistry 1976; 15: 1791-3
13. Kimura Y, Okuda H. Resveratrol isolated from Polygonum cuspidatum root prevents tumor growth and metastasis to lung and tumor-induced neovascularization in Lewis lung carcinoma-bearing mice. J Nutr 2001; 131: 1844-9
14. Jordan VC. Tamoxifen (ICI46.474) as a targeted therapy to treat and prevent breast cancer. Br J Pharmacol 2006; 147: S269-76
15. Tolomeo M, Grimaudo S, Di Cristina A, Roberti M, Pizzirani D, Meli M et al. Pterostilbene and 3′-hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells. Int J Biochem Cell Biol 2005; 37: 1709-26
16. Heo YH, Min HY, Kim S, Lee SK. Growth inhibition and G2/M phase cell cycle arrest by 3,4,5-trimethoxy-4′-bromo-cis-stilbene in human colon cancer cells. J Appl Pharmacol 2007; 15: 95-101
17. de la Lastra CA, Villegas I. Resveratrol as an anti-inflammatory and anti-aging agent: mechanisms and clinical implications. Mol Nutr Food Res 2005; 49: 405-30
18. Gatz SA, Wiesmuller L. Take a break - resveratrol in action on DNA. Carcinogenesis 2008; 29: 321-32
19. Das S, Das DK. Anti-inflammatory responses of resveratrol. Inflamm Allergy Drug Targets 2007; 6: 168-73
20. Benitez DA, Pozo-Guisado E, Clementi M, Castellan E, Fernandez-Salguero PM. Non-genomic action of resveratrol on androgen and oestrogen receptors in prostate cancer: modulation of the phosphoinositide 3-kinase pathway. Br J Cancer 2007; 96: 1595-604
21. Gusmon J, Malonne H, Atassi G. A reappraisal of the potential chemopreventive and chemotherapeutic properties of resveratrol. Carcinogenesis 2001; 22: 1111-7
22. Guengerich PF, Chun YJ, Kim D, Gillam EM, Shimada T. Cytochrome P450 1B1: a target for inhibition in anticarcinogenesis strategies. Mutat Res 2003; 523-524: 173-82
23. Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM. Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Cancer Res 2001; 61: 7456-63
24. Gehm BD, McAndrews JM, Chien PY, Jameson JL. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci U S A 1997; 94: 14138-43
25. Rimando AM, Nagmani R, Feller DR, Yokoyama W. Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J Agric Food Chem 2005; 53: 3403-7
26. Ulrich S, Loitsch SM, Ran O, von Knethen A, Brune B, Schubert-Zsilavecz M et al. Peroxisome proliferator-activated receptor gamma as a molecular target of resveratrol-induced modulation of polyamine metabolism. Cancer Res 2006; 66: 7348-54
27. Harikumar KB, Aggarwal BB. Resveratrol: A multitargeted agent for age-associated chronic diseases. Cell Cycle 2008; 7: 1020-35
28. Kundu JK, Shin YK, Surh YJ. Resveratrol modulates phorbol ester-induced pro-inflammatory signal transduction pathways in mouse skin in vivo: NF-kappaB and AP-1 as prime targets. Biochem Pharmacol 2006; 72: 1506-15
29. Lagouge M, Argmann C, Gerhart-Hines Z, Meziane H, Lerin C, Daussin F et al. Resveratrol Improves mitochondrial function and protects against metabolic disease by activating SIRT1 and PGC-1alpha, Cell 2006; 127: 1109-22
30. Kim D, Nguyen MD, Dobbin MM, Fischer A, Sananbenesi F, Rodgers JT et al. SIRT1 deacetylase protects against neurodegeneration in models for Alzheimer's disease and amyotrophic lateral sclerosis. Embo J 2007; 26: 3169-79
31. Hayashibara T, Yamada Y, Nakayama S, Harasawa H, Tsuruda K, Sugahara K et al. Resveratrol induces downregulation in survivin expression and apoptosis in HTLV-1-infected cell lines: a prospective agent for adult T cell leukemia chemotherapy. Nutr Cancer 2002; 44: 193-201
32. Shankar S, Singh C, Srivastava RK. Chemoprevention by resveratrol: molecular mechanisms and therapeutic potential. Front Biosci 2007; 12: 4839-54
33. Lee SC, Chan J, Clement MV, Pervaiz S. Functional proteomics of resveratrol-induced colon cancer cell apoptosis: caspase-6-mediated cleavage of lamin A is a major signaling loop. Proteomics 2006; 6: 2386-94
34. Delmas D, Rebe C, Lacour S, Filomenko R, Athias A, Gamben P et al. Resveratrol-induced apoptosis is associated with Fas redistribution in the rafts and the formation of a death-inducing signaling complex in colon cancer cells. J Biol Chem 2003; 278: 41482-90
35. Su JL, Lin MT, Hong CC, Chang CC, Shiah SG, Wu CW et al. Resveratrol induces Fast-related apoptosis through Cdc42 activation of ASK1/ JNK-dependent signaling pathway in human leukemia HL-60 cells. Carcinogenesis 2005; 26: 1-10
36. Tsan MF, White JE, Maheshwari JG, Bremner TA, Sacco J. Resveratrol induces Fas signalling-independent apoptosis in THP-1 human monocytic leukaemia cells. Br J Haematol 2000; 109: 405-12
37. Bernhard D, Tinhofer I, Tonko M, Hubl H, Ausserlechner MJ, Greif R et al. Resveratrol causes arrest in the S-phase prior to Fas-independent apoptosis in CEM-C7H2 acute leukemia cells. Cell Death Differ 2000; 7: 834-42
38. Fulda S, Debatin KM. Resveratrol-mediated sensitisation to TRAIL-induced apoptosis depends on death receptor and mitochondrial signalling. Eur J Cancer 2005; 41: 786-98
39. Clement MV, Hirpara JL, Chawdhury SH, Pervaiz S. Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells. Blood 1998; 92: 996-1002
40. Wang Y, Wang B, Cheng J, Yang L, Liu ZL, Balan K et al. FADD-dependent apoptosis induction in Jurkat leukemia T-cells by the resveratrol analogue, 3,4,5-trihydroxy-trans-stilbene. Biochem Pharmacol 2005; 69: 249-54
41. Kundu JK, Chun KS, Kim SO, Surh YJ. Resveratrol inhibits phorbol ester-induced cyclooxygenase-2 expression in mouse skin: MAPKs and AP-1 as potential molecular targets. Biofactors 2004; 21: 33-9
42. Aggarwal BB, Shishodia S. Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol 2006; 71: 1397-421
43. Yu R, Hebbar V, Kim DW, Mandlekar S, Pezzuto JM, Kong AN. Resveratrol inhibits phorbol ester and UV-induced activator protein 1 activation by interfering with mitogen-activated protein kinase pathways. Mol Pharmacol 2001; 60: 217-24
44. Frojdo S, Cozzone D, Vidal H, Pirola L. Resveratrol is a class IA phospho-inositide 3-kinase inhibitor. Biochem J 2007; 406: 511-8
45. Pozo-Guisado E, Lorenzo-Benayas MJ, Fernandez-Salguero PM. Resveratrol modulates the phosphoinositide 3-kinase pathway through an estrogen receptor alpha-dependent mechanism: relevance in cell proliferation. Int J Cancer 2004; 109: 167-73
46. Inoue H, Jiang XF, Katayama T, Osada S, Umesono K, Namura S. Brain protection by resveratrol and fenofibrate against stroke requires peroxisome proliferator-activated receptor alpha in mice. Neurosci Lett 2003; 352: 203-6
47. BowersJL, Tyulmenkov VV, Jernigan SC, Klinge CM. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. Endocrinology 2000; 141: 3657-67
48. Mueller SO, Simon S, Chae K, Metzler M, Korach KS. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. Toxicol Sci 2004; 80: 14-25
49. Wada-Hiraike O, Warner M, Gustafsson JA. New developments in oestrogen signalling in colonic epithelium. Biochem Soc Trans 2006; 34: 1114-6
50. Kundu JK, Shin YK, Kim SH, Surh YJ. Resveratrol inhibits phorbol ester-induced expression of COX-2 and activation of NF-kappaB in mouse skin by blocking IkappaB kinase activity. Carcinogenesis 2006; 27: 1465-74
51. Suh N, Paul S, Hao X, Simi B, Xiao H, Rimando AM et al. Pterostilbene, an active constituent of blueberries, suppresses aberrant crypt foci formation in the azoxymethane-induced colon carcinogenesis model in rats. Clin Cancer Res 2007; 13: 350-5
52. Hougee S, Faber J, Sanders A, de Jong RB, van den Berg WB, Garssen J et al. Selective COX-2 inhibition by a Pterocarpus marsupium extract characterized by pterostilbene, and its activity in healthy human volunteers. Planta Med 2005; 71: 387-92
53. Subbaramaiah K, Dannenberg AJ. Resveratrol inhibits the expression of cyclooxygenase-2 in mammary epithelial cells. Adv Exp Med Biol 2001; 492: 147-57
54. Subbaramaiah K, Chung WJ, Michaluart P, Telang N, Tanabe T, Inoue H et al. Resveratrol inhibits cyclooxygenase-2 transcription and activity in phorbol ester-treated human mammary epithelial cells. J Biol Chem 1998; 273: 21875-82
55. Das S, Fraga CG, Das DK. Cardioprotective effect of resveratrol via HO-1 expression involves p38map kinase and PI-3-kinase signaling, but does not involve NFkappaB. Free Radic Res 2006; 40: 1066-75
56. Chun YJ, Kim MY, Guengerich FP. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem Biophys Res Commun 1999; 262: 20-4
57. Mikstacka R, Rimando AM, Szalaty K, Stasik K, Baer-Dubowska W. Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities. Xenobiotica 2006; 36: 269-85
58. Mikstacka R, Przybylska D, Rimando AM, Baer-Dubowska W. Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans-resveratrol methyl ethers. Mol Nutr Food Res 2007; 51: 517-24
59. Belleri M, Ribatti D, Nicoli S, Cotelli F, Forti L, Vannini V et al. Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3,5,4′- trimethoxystilbene. Mol Pharmacol 2005; 67: 1451-9
60. Banerjee S, Bueso-Ramos C, Aggarwal BB. Suppression of 7,12-dimethylbenz[a]anthracene-induced mammary carcinogenesis in rats by resveratrol: role of nuclear factor-kappaB, cyclooxygenase 2, and matrix metalloprotease 9. Cancer Res 2002; 62: 4945-54
61. Oak MH, El Bedoui J, Schini-Kerth VB. Antiangiogenic properties of natural polyphenols from red wine and green tea. J Nutr Biochem 2005; 16: 1-8
62. Chen Y, Tseng SH. Review. Pro- and anti-angiogenesis effects of resveratrol. In Vivo 2007; 21: 365-70
63. Howitz KT, Bitterman KJ, Cohen HY, Lamming DW, Lavu S, Wood JG et al. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature 2003; 425: 191-6
64. Walle T, Hsieh F, DeLegge MH, Oatis JE Jr, Walle UK. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos 2004; 32: 1377-82
65. Goldberg DM, Yan J, Soleas GJ. Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin Biochem 2003; 36: 79-87
66. Yu C, Shin YG, Chow A, Li Y, KosmederJW, Lee YS et al. Human, rat, and mouse metabolism of resveratrol. Pharm Res 2002; 19: 1907-14
67. Remsberg CM, Yanez JA, Ohgami Y, Vega-Villa KR, Rimando AM, Davies NM. Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, anti-inflammatory, antioxidant and analgesic activity. Phytother Res 2008; 22: 169-79
68. Roupe KA, Yanez JA, Teng XW, Davies NM. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. J Pharm Pharmacol 2006; 58: 1443-50
69. Marier JF, Vachon P, Gritsas A, Zhang J, Moreau JP, Ducharme MP. Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. J Pharmacol Exp Ther 2002; 302: 369-73
70. Aziz MH, Afaq F, Ahmad N. Prevention of ultraviolet-B radiation damage by resveratrol in mouse skin is mediated via modulation in survivin. Photochem Photobiol 2005; 81: 25-31
71. Afaq F, Adhami VM, Ahmad N. Prevention of short-term ultraviolet B radiation-mediated damages by resveratrol in SKH-1 hairless mice. Toxicol Appl Pharmacol 2003; 186: 28-37
72. Kapadia GJ, Azuine MA, Tokuda H, Takasaki M, Mukainaka T, Konoshima T et al. Chemopreventive effect of resveratrol, sesamol, sesame oil and sunflower oil in the Epstein-Barr virus early antigen activation assay and the mouse skin two-stage carcinogenesis. Pharmacol Res 2002; 45: 499-505
73. Li ZG, Hong T, Shimada Y, Komoto I, Kawabe A, Ding Y et al. Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol. Carcinogenesis 2002; 23: 1531-6
74. Provinciali M, Re F. Donnini A, Orlando F, Bartozzi B, Di Scasio G et al. Effect of resveratrol on the development of spontaneous mammary tumors in HER-2/neu transgenic mice, Int J Cancer 2005; 115: 36-45
75. Whitsett T, Carpenter M, Lamartiniere CA, Resveratrol, but not EGCC, in the diet suppresses DMBA-induced mammary cancer in rats. J Carcinog 2006; 5: 15
76. Coussens LM, Werb Z. Inflammation and cancer. Nature 2002; 420: 860-7
77. Ulrich CM, Bigler J, Potter JD. Non-steroidal anti-inflammatory drugs for cancer prevention: promise, perils and pharmacogenetics. Nat Rev Cancer 2006; 6: 130-40
78. Ohta T, Takahashi M, Ochiai A. Increased protein expression of both inducible nitric oxide synthase and cyclooxygenase-2 in human colon cancers. Cancer Lett 2006; 239: 246-53
79. Cianchi F, Cortesini C, Fantappie O, Messerini L, Schiavone N, Vannacci A et al. Inducible nitric oxide synthase expression in human colorectal cancer: correlation with tumor angiogenesis. Am J Pathol 2003; 162: 793-801
80. Roo CV, Kawamori T, Hamid R, Ready BS. Chemoprevention of colonic aberrant crypt foci by an inducible nitric oxide synthase-selective inhibitor. Carcinogenesis 1999; 20: 641-4
81. Takahashi M, Mutoh M, Shoji Y, Sato H, Kamanaka Y, Naka M et al. Suppressive effect of an inducible nitric oxide inhibitor, ONO-1714, on AOM-induced rat colon carcinogenesis. Nitric Oxide 2006; 14: 130-6
82. Rao CV, Indranie C, Simi B, Manning PT, Connor JR, Ready BS. Chemopreventive properties of a selective inducible nitric oxide synthase inhibitor in colon carcinogenesis, administered alone or in combination with celecoxib, a selective cyclooxygenase-2 inhibitor. Cancer Res 2002; 62: 165-70
83. Tessitore L, Davit A, Sarotto I, Caderni G. Resveratrol depresses the growth of colorectal aberrant crypt foci by affecting bax and p21 (CIP) expression. Carcinogenesis 2000; 21: 1619-22
84. Sengottuvelan M, Viswanathan P, Nalini N. Chemopreventive effect of frans-resveratrol - a phytoalexin against colonie aberrant crypt foci and cell proliferation in 1,2-dimethylhydrazine induced colon carcinogenesis. Carcinogenesis 2006; 27: 1038-46
85. Carpet DE, Pierre F. Point: From animal models to prevention of colon cancer. Systematic review of chemoprevention in min mice and choice of the model system. Cancer Epidemiol Biomarkers Prev 2003; 12: 391-400
86. Schneider Y, Duranton B, Gosse F, Schleiffer R, Seiler N, Raul F. Resveratrol inhibits intestinal tumorigenesis and modulates host-defense-related gene expression in an animal model of human familial adenomatous polyposis. Nutr Cancer 2001; 39: 102-7
87. Ziegler CC, Rainwater L, Whelan J, McEntee MF. Dietary resveratrol does not affect intestinal tumorigenesis in Apc(Min/+) mice. J Nutr 2004; 134:5-10
88. Sale S, Tunstall RG, Ruparelia KC, Potter GA, Steward WP, Gescher AJ. Comparison of the effects of the chemopreventive agent resveratrol and its synthetic analog trans-3,4,5,4′-tetramethoxystilbene (DMU-212) on adenoma development in the Apc(Min+) mouse and cyclooxygenase-2 in human-derived colon cancer cells, Int J Cancer 2005; 115: 194-201
89. Kineman BD, Au A, Paiva NL, Kaiser MS, Brummer EC, Bin DF. Transgenic alfalfa that accumulates piceid (trans-resveratrol-3-O- beta-D-glucopyranoside) requires the presence of beta-glucosidase to inhibit the formation of aberrant crypt foci in the colon of CF-1 mice. Nutr Cancer 2007; 58: 66-74
90. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF. Beecher CW et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997; 275: 218-20
91. Zern TL, Wood RJ, Greene C, West KL, Liu Y, Aggarwal D et al. Grape polyphenols exert a cardioprotective effect in pre- and postmenopausal women by lowering plasma lipids and reducing oxidative stress. J Nutr 2005; 135: 1911-7
92. Levi F, Pasche C, Lucchini F, Ghidoni R, Ferraroni M, La Vecchia C. Resveratrol and breast cancer risk. Eur J Cancer Prev 2005; 14: 139-42
93. Boocock DJ, Faust GE, Patel KR, Schinas AM, Brown VA, Ducharme MP et al. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol Biomarkers Prev 2007; 16: 1246-52
94. Manners GD, Swan EP. Stilbenes in the barks of five Canadian Picea species. Phytochemistry 1971; 10: 607-10
95. Waffo-Teguo P, Hawthorne ME, Cuendet M, Merillon JM, Kinghorn AD, Pezzuto JM et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer 2001; 40: 173-9
96. Wober J, Moller F, Richter T, Unger C, Weigt C, Jandausch A et al. Activation of estrogen receptor-beta by a special extract of Rheum rhaponticum (ERr 731), its aglycones and structurally related compounds. J Steroid Biochem Mol Biol 2007; 107: 191-201
97. Ko SK. Effects of stilbene derivatives from Rheum undulatum on 5a-reductase activity. Saengyak Hakhoechi 2000; 31: 245-8
98. Ryu SY, Choi SU, Lee CO, Lee SH, Ahn JW, Zee OP. Antitumor activity of some phenolic components in plants. Arch Pharm Res 1994; 17: 42-4
99. Mellanen P, Petanen T, Lehtimaki J, Makela S, Bylund G, Holmbom B et al. Wood-derived estrogens: studies in vitro with breast cancer cell lines and in vivo in trout. Toxicol Appl Pharmacol 1996; 136: 381-8
100. Deshpande VH, Srinivasan R, Rao AVR. Wood phenolics of Morus species. IV. Phenolics of the heartwood of five Morus species. Indian J Chem 1975; 13: 453-7
101. Lee SK, Nam KA, Hoe YH, Min HY, Kim EY, Ko H et al. Synthesis and evaluation of cytotoxicity of stilbene analogues. Arch Pharm Res 2003; 26: 253-7
102. Kim YH, Park C, Lee JO, Kim GY, Lee WH, Choi YH et al. Induction of apoptosis by piceatannol in human leukemic U937 cells through down-regulation of Bcl-2 and activation of caspases. Oncol Rep 2008; 19: 961-7
103. Kuo PL, Hsu YL. The grape and wine constituent piceatannol inhibits proliferation of human bladder cancer cells via blocking cell cycle progression and inducing Fas/membrane bound Fas ligand-mediated apoptotic pathway. Mol Nutr Food Res 2008; 52: 408-18
104. Waterhouse AL, Lamuela-Raventos RM. The occurrence of piceid, a stilbene glucoside, in grape berries. Phytochemistry 1994; 37: 571-3
105. Tyukavkina NA, Gromova AS, Lutskii VI, Voronov VK. Hydroxystilbenes from Pinus sibirica bark. Khimiya Prirodnykh Soedinenii 1972; 5: 600-3
106. Gromovo AS, Lutskii VI, Tyukavkina NA. Stilbenes from the bark of some Pinaceae species. Koksnes Kimija 1979; 3: 103-9
107. Clausen TP, Reichardt PB, Bryant JP. Pinosylvin and pinosylvin methyl ether as feeding deterrents in green alder. J Chem Ecol 1986; 12: 2117-31
108. Jorgensen E. The formation of pinosylvin and its monomethyl ether in the sapwood of Pinus resinosa. Can J Bot 1961; 39: 1765-72
109. Skinnider L, Stoessl A. The effect of the phytoalexins, lubimin, (-)-maackiain, pinosylvin, and the related compounds dehydroloroglossol and hordatine M on human lymphoblastoid cell lines. Experientia 1986; 42: 568-70
110. Pezet R, Pont V. Demonstration of pterostilbene in clusters of Vitis vinifera. Plant Physiol Biochem 1988; 26: 603-7
111. Maurya R, Ray AB, Duah FK, Slatkin DJ, Schiff PL Jr. Constituents of Pterocarpus marsupium. J Nat Prod 1984; 47: 179-81
112. MacRae WD, Towers GHN. Nonalkaloidal constituents of Virola elongata bark. Phytochemistry 1985; 24: 561-6
113. Cardile V, Chillemi R, Lombarde L, Sciuto S, Spatafora C, Tringali C. Antiproliferative activity of methylated analogues of E- and Z-resveratrol. Z Naturforsch [C] 2007; 62: 189-95
114. Murakami T, Tanaka K. New phenolic glycosides in Rhei palmati rhizomes. Tetrahedron Lett 1972; 29: 2965-8
115. Ferrer P, Asensi M, Segarra R, Ortega A, Benlloch M, Obrador E et al. Association between pterostilbene and quercetin inhibits metastatic activity of B16 melanoma. Neoplasia 2005; 7: 37-47
116. Asensi M, Medina I, Ortega A, Carretero J, Bano MC, Obrador E et al. Inhibition of cancer growth by resveratrol is related to its low bioavailability. Free Radic Biol Med 2002; 33: 387-98
117. Sengottuvelan M, Nalini N. Dietary supplementation of resveratrol suppresses colonic tumour incidence in 1,2-dimethylhydrazine-treated rats by modulating biotransforming enzymes and aberrant crypt foci development. Br J Nutr 2006; 96: 145-53
118. Pan MH, Coo JH, Lai CS, Wang YJ, Chen WM, Lo CY et al. Antitumor activity of 3,5,4′-trimethoxystilbene in COLO 205 cells and xenografts in SCID mice. Mol Carcinogen 2008; 47: 184-96
119. Martin AR, Villegas I, Sanchez-Hidalgo M, de la Lastra CA. The effects of resveratrol, a phytoalexin derived from red wines, on chronic inflammation induced in an experimentally induced colitis model. Br J Pharmacol 2006; 147: 873-85