Anti-tumor properties of stilbene-based resveratrol analogues: Recent results

Natural Product Communications

Volumn 2, Issue 4, 2017, Pages 499-513

  Chillemi, Rosa ^a   Sciuto, Sebastiano ^a   Spatafora, Carmela ^a   Tringali, Corrado ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Anti tumor properties; Antiproliferative activity; Apoptotic activity; Methoxystilbenes; Resveratrol analogues

Indexed keywords

ANTINEOPLASTIC AGENT; CATECHOL; DIMETHOXYSTILBENE; HEXAHYDROXYSTILBENE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MONOETHOXYSTILBENE; OXYRESVERATROL; PENTAHYDROXYSTILBENE; PICEATANNOL; PINOSYLVIN; POLYHYDROXYSTILBENE; PTEROSTILBENE; PYROGALLOL; RESVERATROL; RHAPONTIGENIN; STILBENE; STILBENE DERIVATIVE; TETRAMETHOXYSTILBENE; TRIMETHOXYSTILBENE; TUMOR NECROSIS FACTOR; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL LINE; CANCER INHIBITION; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; HUMAN; IN VIVO STUDY; ISOMER; NONHUMAN; TRANSCRIPTION INITIATION;

EID: 84864983865     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: None     Document Type: Article

References (74)

1. Renaud S, de Lorgeril M. (1992) Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet, 339, 1523-1526.
2. Takaoka MJ. (1940) Of the phenolic substances of white hellebore (Veratrum grandiflorum Loes. fil.). Journal of the Faculty of Science Hokkaido Imperial University, 3, 1-16.
3. Nonomura S, Kanagawa H, Makimoto A. (1963) Chemical constituents of Polygonaceous plants. I. Studies on the components of Ko-jo-kon (Polygonum cuspidatum Sieb. et Zucc.). Yakugaku Zasshi, 83, 988-990.
4. Jeandet P, Bessis R, Sbaghi M, Meunier P, Trollat P. (1995) Resveratrol content of wines of different ages: relationship with fungal disease pressure in the vineyard. American Journal of Enology and Viticulture, 46, 1-4.
5. Baur JA, Sinclair DA. (2006) Therapeutic potential of resveratrol: the in vivo evidence. Nature Reviews Drug Discovery, 5, 493-506.
6. Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y. (2004) Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Research, 24, 2783-2840.
7. Burjonroppa S, Fujise K. (2006) Resveratrol as cardioprotective agent: evidence from bench and bedside. In Resveratrol in Health and Disease, Aggarwal BB, Shishodia S. (Eds). Taylor & Francis, London, 539-555.
8. Signorelli P, Ghidoni R. (2005) Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. Journal of Nutritional Biochemistry, 16, 449-466.
9. Delmas D, Lançon A, Colin D, Jannin B, Latruffe N. (2006) Resveratrol as a chemopreventive agent: a promising molecule for fighting cancer. Current Drug Targets, 7, 423-442.
10. Aggarwal BB, Shishodia S. (2006) Oxidative Stress and Disease vol 20. Resveratrol in Health and Disease. 1-712 pp. Taylor & Francis, London.
11. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM. (1997) Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science, 275, 218-220.
12. Fulda S, Debatin KM. (2006) Resveratrol modulation of signal transduction in apoptosis and cell survival: a mini-review. Cancer Detection and Prevention, 30, 217-223.
13. Aggarwal BB, Shishodia S. (2006) Molecular targets of dietary agents for prevention and therapy of cancer. Biochemical Pharmacology, 71, 1397-1421.
14. Jazirehi AR, Bonavida B. (2006) Resveratrol as a sensitizer to apoptosis-inducing stimuli. In Resveratrol in Health and Disease. Aggarwal BB, Shishodia S. (Eds). Taylor & Francis, London, 399-421.
15. Wenzel E, Somoza V. (2005) Metabolism and bioavailability of trans-resveratrol. Molecular Nutrition & Food Research, 49, 472-481.
16. Gorham J. (1995) The Biochemistry of the Stilbenoids. Chapman & Hall, London.
17. Mattivi F, Remiero F, Korhammer S. (1995) Isolation, characterization, and evolution in red wine vinification of resveratrol monomers. Journal of Agricultural and Food Chemistry, 43, 1820-1823.
18. Ingham JL. (1976) 3, 5, 4'-Trihydroxystilbene as a phytoalexin from groundnuts (Arachis hypogaea). Phytochemistry, 15, 1791-1793.
19. Sarker SD, Whiting P, Dinan L. (1999) Identification and ecdysteroid antagonist activity of three resveratrol trimers (suffruticosols A, B and C) from Paeonia suffruticosa. Tetrahedron, 55, 513-24.
20. Hadfield JA, Gaukroger K, Hirst N, Weston AP, Lawrence NJ, McGown AT. (2005) Synthesis and evaluation of double bond substituted combretastatins. European Journal of Medicinal Chemistry, 40, 529-541.
21. Tozer GM, Kanthou C, Baguley BC. (2005) Disrupting tumour blood vessels. Nature Reviews Cancer, 5, 423-435.
22. Tron GC, Pirali T, Sorba G, Pagliai F, Busacca S, Genazzani AA. (2006) Medicinal chemistry of combretastatin A4: Present and future directions. Journal of Medicinal Chemistry, 49, 3033-3044.
23. Ovesná Z, Horváthová-Kozics K. (2005) Structure-activity relationship of trans-resveratrol and its analogues. Neoplasma, 52, 450-455.
24. Zhou B, Liu Z-L. (2005) Bioantioxidants: from chemistry to biology. Pure and Applied Chemistry, 77, 1887-1903.
25. Roupe KA, Remsberg CM, Yáñez JA, Davies NM. (2006) Pharmacometrics of stilbenes: seguing towards the clinic. Current Clinical Pharmacology, 1, 81-101.
26. King RE, Bomser JA, Min DB. (2006) Bioactivity of resveratrol. Comprehensive Reviews in Food Science and Food Safety, 5, 65-70.
27. Celimene CC, Smith DR, Young RA, Stanosz GR. (2001) In vitro inhibition of Spaeorpsis sapinea by natural stilbenes. Phytochemistry, 56, 161-165.
28. Roupe KA, Fukuda C, Yáñez JA, Halls S, Davies NM. (2005) Pinosylvin: Method of analysis, anti-cancer activity and metabolism. The AAPS Journal, 7 (S2) Abstract T3261.
29. Cai Y-J, Fang J-G, Ma L-P, Yang L, Liu Z-L. (2003) Inhibition of free radical-induced peroxidation of rat liver microsomes by resveratrol and its analogues. Biochimica et Biophysica Acta, 1637, 31-38.
30. Cai Y-J, Wei Q-Y, Fang J-G, Yang L, Liu Z-L, Wyche JH, Han Z. (2004) The 3, 4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities. Anticancer Research, 24, 999-1002.
31. Lion CJ, Matthews CS, Stevens MFG, Westwell AD. (2005) Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes. Journal of Medicinal Chemistry, 48, 1292-1295.
32. Heynekamp JJ, Weber WM, Hunsaker LA, Gonzales AM, Orlando RA, Deck LM, Vander Jagt DL. (2006) 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. Journal of Medicinal Chemistry, 49, 7182-7189.
33. Rimando AM, Cuendet M, Desmarchelier C, Mehta RG, Pezzuto JM, Duke SO. (2002) Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. Journal of Agricultural and Food Chemistry, 50, 3453-3457.
34. Ferrer P, Asensi M, Segarra R, Ortega A, Benlloch M, Obrador E, Varea MT, Asensio G, Jorda L, Estrela JM. (2005) Association between pterostilbene and quercetin inhibits metastatic activity of B16 melanoma. Neoplasia, 7, 37-47.
35. Tolomeo M, Grimaudo S, Di Cristina A, Roberti M, Pizzirani D, Meli M, Dusonchet L, Gebbia N, Abbadessa V, Crosta L, Barucchello R, Grisolia G, Invidiata F, Simoni D. (2005) Pterostilbene and 3'-hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells. International Journal of Biochemistry & Cell Biology, 37, 1709-1726.
36. Roberti M, Pizzirani D, Simoni D, Rondanin R, Baruchello R, Bonora C, Buscemi F, Grimaudo S, Tolomeo M. (2003) Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. Journal of Medicinal Chemistry, 46, 3546-3554.
37. MacRae WD, Towers GHN. (1985) Non-alkaloidal constituents of Virola elongate bark. Phytochemistry, 24, 561-566.
38. Lee SK, Nam KA, Hoe YH, Min H-Y, Kim E-Y, Ko H, Song S, Lee T, Kim S. (2003) Synthesis and evaluation of cytotoxicity of stilbene analogues. Archives of Pharmacal Research, 26, 253-257.
39. Schneider Y, Chabert P, Stutzmann J, Coelho D, Fougerousse A, Gosse F, Launay J-F, Brouillard R, Raul F. (2003) Resveratrol analog (Z)-3, 5, 4'-trimethoxystilbene is a potent anti-mitotic drug inhibiting tubulin polymerization. International Journal of Cancer, 107, 189-196.
40. Schneider Y, Fischer B, Coelho D, Roussi S, Gosse F, Bischoff P, Raul F. (2004) (Z)-3, 5, 4'-Tri-O-methylresveratrol induces apoptosis in human lymphoblastoid cells independently of their p53 status. Cancer Letters, 211, 155-161.
41. Simoni D, Roberti M, Invidiata FP, Aiello E, Aiello S, Marchetti P, Baruchello R, Eleopra M, Di Cristina A, Grimaudo S, Gebbia N, Crosta L, Dieli F, Tolomeo M. (2006) Stilbene-based anticancer agents: Resveratrol analogues active toward HL60 leukemic cells with a non-specific phase mechanism. Bioorganic & Medicinal Chemistry Letters, 16, 3245-3248.
42. 1 phase and induces differentiation in leukemia cells. Journal of Medicinal Chemistry, 49, 3012-3018.
43. Minutolo F, Sala G, Bagnacani A, Bertini S, Carboni I, Placanica G, Prota G, Rapposelli S, Sacchi N, Macchia M, Ghidoni R. (2005) Synthesis of a resveratrol analogue with high ceramide-mediated proapoptotic activity on human breast cancer cells. Journal of Medicinal Chemistry, 48, 6783-6786.
44. Matsuoka A, Takeshita K, Furuta A, Ozaki M, Fukuhara K, Miyata N. (2002) The 4'-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol. Mutation Research, 521, 29-35.
45. Petralia S, Spatafora C, Tringali C, Foti MC, Sortino S. (2004) Hydrogen atom abstraction from resveratrol and two lipophilic derivatives by tert-butoxyl radicals. A laser flash photolysis study. New Journal of Chemistry, 28, 1484-1487.
46. Ruan B-F, Huang X-F, Ding H, Xu C, Ge H-M, Zhu H-L, Tan R-X. (2006) Synthesis and cytotoxic evaluation of a series of resveratrol derivatives. Chemistry & Biodiversity, 3, 975-981.
47. Belleri M, Ribatti D, Nicoli S, Cotelli F, Forti L, Vannini V, Stivala LA, Presta M. (2005) Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3, 5, 4'-trimethoxystilbene. Molecular Pharmacology, 67, 1451-1459.
48. Bhowmick N, Neilson EG, Moses HL. (2004) Stromal fibroblasts in cancer initiation and progression. Nature, 432, 332-337.
49. Mikstacka R, Rimando AM, Szalaty K, Stasik K, Baer-Dubowska W. (2006) Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities. Xenobiotica, 36, 269-285.
50. Nicolosi G, Spatafora C, Tringali C. (2002) Chemo-enzymatic preparation of resveratrol derivatives. Journal of Molecular Catalysis B: Enzymatic, 16, 223-229.
51. Cardile V, Lombardo L, Spatafora C, Tringali C. (2005) Chemo-enzymatic synthesis and antiproliferative activity of resveratrol analogues. Bioorganic Chemistry, 33, 22-33.
52. Likhitwitayawuid K, Sornsute A, Sritularak B, Ploypradith P. (2006) Chemical transformations of oxyresveratrol (trans-2, 4, 3', 5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. Bioorganic & Medicinal Chemistry Letters, 16, 5650-5653.
53. Cardile V, Chillemi R, Lombardo L, Sciuto S, Spatafora C, Tringali C. (2007) Antiproliferative activity of methylated analogues of E- and Z-resveratrol. Zeitschrift für Naturforschung C, 62c, in press.
54. Andrus MB, Liu J. (2006) Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings. Tetrahedron Letters, 47, 5811-5814.
55. Wang Y, Wang B, Cheng J, Yang L, Liu Z-L, Balan K, Pantazis P, Wyche JH, Han Z. (2005) FADD-dependent apoptosis induction in Jurkat leukemia T-cells by the resveratrol analogue, 3, 4, 5-trihydroxy-trans-stilbene. Biochemical Pharmacology, 69, 249-254.
56. Roupe K, Fukada C, Halls S, Teng XW, Davies NM. (2004) Anti-cancer activity, pharmacokinetics and metabolism of piceatannol in vitro and in vivo. Journal of Pharmacy & Pharmaceutical Sciences, 7, 75-76.
57. Larrosa M, Tomas-Barberan FA, Espin JC. (2004) The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells. European Journal of Nutrition, 43, 275-284.
58. Barton BE, Karras JG, Murphy TF, Barton A, Huang HFS. (2004) Signal transducer and activator of transcription 3 (STAT3) activation in prostate cancer: Direct STAT3 inhibition induces apoptosis in prostate cancer lines. Molecular Cancer Therapeutics, 3, 11-20.
59. Chowdhury SA, Kishino K, Satoh R, Hashimoto K, Kikuchi H, Nishikawa H, Shirataki Y, Sakagami H. (2005) Tumor-specificity and apoptosis-inducing activity of stilbenes and flavonoids. Anticancer Research, 25, 2055-2063.
60. Takei M, Umeyama A, Arihara S, Matsumoto H. (2005) Effect of piceatannol in human monocyte-derived dendritic cells in vitro. Journal of Pharmaceutical Sciences, 94, 974-982.
61. Füllbeck M, Huang X, Dumdey R, Frommel C, Dubiel W, Preissner R. (2005) Novel curcumin- and emodin-related compounds identified by in silico 2D/3D conformer screening induce apoptosis in tumor cells. BMC Cancer, 5, 97, doi: 10.1186/1471-2407-5-97
62. Murias M, Jaeger W, Handler N, Erker T, Horvath Z, Szekeres T, Nohl H, Gille L. (2005) Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochemical Pharmacology, 69, 903-912.
63. Ovesná Z, Kozics K, Bader Y, Saiko P, Handler N, Erker T, Szekeres T. (2006) Antioxidant activity of resveratrol, piceatannol and 3, 3', 4, 4', 5, 5'-hexahydroxy-trans-stilbene in three leukaemia cell lines. Oncology Reports, 16, 617-624.
64. Matsuda H, Tomohiro N, Hiraba K, Harima S, Ko S, Matsuo K, Yoshikawa M, Kubo M. (2001) Study on anti-Oketsu activity of rhubarb II. Anti-allergic effects of stilbene components from Rhei undulati Rhizoma (dried rhizome of Rheum undulatum cultivated in Korea). Biological & Pharmaceutical Bulletin, 24, 264-267.
65. Roupe KA, Helms GL, Halls SC, Yáñez JA, Davies NM. (2005) Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: applications to metabolism, pharmacokinetics and anti-cancer studies. Journal of Pharmacy & Pharmaceutical Sciences, 8, 374-386.
66. Likhitwitayawuid K, Sritularak B, Benchanak K, Lipipun V, Mathew J, Schinazi RF. (2005) Phenolics with antiviral activity from Millettia erythrocalyx and Artocarpus lakoocha. Natural Product Research, 19, 177-182.
67. Kim YM, Yun J, Lee C-K, Lee H, Min KR, Kim Y. (2002) Oxyresveratrol and hydroxystilbene compounds: Inhibitory effect on tyrosinase and mechanism of action. Journal of Biological Chemistry, 277, 16340-16344.
68. Sale S, Verschoyle RD, Boocock D, Jones DJL, Wilsher N, Ruparelia KC, Potter GA, Farmer PB, Steward WP, Gescher AJ. (2004) Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans-3, 4, 5, 4'-tetramethoxystilbene. British Journal of Cancer, 90, 736-744.
69. Potter GA, Butler PC, Ruparelia KC, Ijaz T, Wilsher NC, Wanogho E, Tan HL, Hoang TTV, Stanley LA, Burke MD. (2002) DMU212: a novel CYP1B1 activated anticancer prodrug. British Journal of Cancer, 86, S117.
70. Min+ mouse and cyclooxygenase-2 in human-derived colon cancer cells. International Journal of Cancer, 115, 194-201.
71. Gosslau A, Chen M, Ho C-T, Chen KY. (2005) A methoxy derivative of resveratrol analogue selectively induced activation of the mitochondrial apoptotic pathway in transformed fibroblasts. British Journal of Cancer, 92, 513-521.
72. Horvath Z, Murias M, Saiko P, Erker T, Handler N, Madlener S, Jaeger W, Grusch M, Fritzer-Szekeres M, Krupitza G, Szekeres T. (2006) Cytotoxic and biochemical effects of 3, 3', 4, 4', 5, 5'-hexahydroxystilbene, a novel resveratrol analog in HL-60 human promyelocytic leukemia cells. Experimental Hematology, 34, 1377-1384.
73. Lee E-J, Min H-Y, Park HJ, Chung H-J, Kim S, Han YN, Lee SK. (2004) G2/M cell cycle arrest and induction of apoptosis by a stilbenoid, 3, 4, 5-trimethoxy-4'-bromo-cis-stilbene, in human lung cancer cells. Life Sciences, 75, 2829-2839.
74. Gaukroger K, Hadfield JA, Lawrence NJ, Nolan S, McGown AT. (2003) Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? Organic & Biomolecular Chemistry, 1, 3033-3037.