A review of the pharmacological effects of piceatannol on cardiovascular diseases

Phytotherapy Research

Volumn 28, Issue 11, 2014, Pages 1581-1588

  Tang, Yee Ling ^a   Chan, Shun Wan ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Cardiovascular diseases; Piceatannol; Resveratrol; Stilbene

Indexed keywords

PICEATANNOL; RESVERATROL; 3,3',4,5'-TETRAHYDROXYSTILBENE; STILBENE DERIVATIVE;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; ATHEROSCLEROSIS; BRUGADA SYNDROME; CARDIOVASCULAR DISEASE; CARDIOVASCULAR MORTALITY; CARDIOVASCULAR RISK; CARDIOVASCULAR SYSTEM; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEVELOPED COUNTRY; DEVELOPING COUNTRY; DIET SUPPLEMENTATION; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; ECG ABNORMALITY; HEART ARRHYTHMIA; HEART DEATH; HUMAN; HYPERCHOLESTEROLEMIA; INCIDENCE; LONG QT SYNDROME; MALE; NONHUMAN; RAT; SOCIAL ASPECT; VASODILATATION; ANIMAL; CARDIOVASCULAR DISEASES;

VITACEAE;

ANIMALS; CARDIOVASCULAR DISEASES; HUMANS; STILBENES;

EID: 84918838028     PISSN: 0951418X     EISSN: 10991573     Source Type: Journal    
DOI: 10.1002/ptr.5185     Document Type: Article

References (72)

1. Ashikawa K, Majumdar S, Banerjee S, Bharti AC, Shishodia S, Aggarwal BB. 2002. Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation. J Immunol 169: 6490-6497.
2. Batchvarova N, Wang XZ, Ron D. 1995. Inhibition of adipogenesis by the stress-induced protein CHOP (Gadd153). EMBO J 14: 4654-4661.
3. Bavaresco L. 2003. Role of viticultural factors on stilbene concentrations of grapes and wine. Drugs Exp Clin Res 29: 181-187.
4. Bavaresco L, Vezzulli S, Battilani P, Giorni P, Pietri A, Bertuzzi T. 2003. Effect of ochratoxin A-producing Aspergilli on stilbenic phytoalexin synthesis in grapes. J Agric Food Chem 51: 6151-6157.
5. Cantos E, Espin JC, Fernandez MJ, Oliva J, Tomas-Barberan FA. 2003. Postharvest UV-C-irradiated grapes as a potential source for producing stilbene-enriched red wines. J Agric Food Chem 51: 1208-1214.
6. Carmena R, Duriez P, Fruchart JC. 2004. Atherogenic lipoprotein particles in atherosclerosis. Circulation 109: III2-7.
7. Chai YY,Wang F, Li YL, Liu K, Xu H. 2012. Antioxidant activities of stilbenoids from Rheum emodi Wall. Evid Based Complement Alternat Med 2012: 603678.
8. Chan E, Chan JY, Wu JH, et al. 2012. Serum nitric oxide synthase activity is a novel predictor of impaired vasorelaxation in rats. Clin Exp Pharmacol Physiol 39: 894-896.
9. Chan JY, Yuen AC, Chan RY, Chan SW. 2013. A review of the cardiovascular benefits and antioxidant properties of allicin. Phytother Res 27: 637-646.
10. Chen WP, Hung LM, Hsueh CH, Lai LP, Su MJ. 2009. Piceatannol, a derivative of resveratrol, moderately slows I(Na) inactivation and exerts antiarrhythmic action in ischaemia-reperfused rat hearts. Br J Pharmacol 157: 381-391.
11. Chen JS, Chen YH, Huang PH, et al. 2012. Ginkgo biloba extract reduces high-glucose-induced endothelial adhesion by inhibiting the redox-dependent interleukin-6 pathways. Cardiovasc Diabetol 11: 49.
12. Choi KH, Kim JE, Song NR, et al. 2010. Phosphoinositide 3-kinase is a novel target of piceatannol for inhibiting PDGF-BB-induced proliferation and migration in human aortic smooth muscle cells. Cardiovasc Res 85: 836-844.
13. Dantas AP, Jimenez-Altayo F, Vila E. 2012. Vascular aging: facts and factors. Front Physiol 3: 325.
14. Devaraj S, Davis B, Simon SI, Jialal I. 2006. CRP promotes monocyte-endothelial cell adhesion via Fcgamma receptors in human aortic endothelial cells under static and shear flow conditions. Am J Physiol Heart Circ Physiol 291: H1170-1176.
15. Fabre KM, Saito K, DeGraff W, et al. 2011. The effects of resveratrol and selected metabolites on the radiation and antioxidant response. Cancer Biol Ther 12: 915-923.
16. Farahi N, Cowburn AS, Upton PD, et al. 2007. Eotaxin-1/CC chemokine ligand 11: a novel eosinophil survival factor secreted by human pulmonary artery endothelial cells. J Immunol 179: 1264-1273.
17. Fritzenwanger M, Meusel K, Foerster M, Kuethe F, Krack A, Figulla HR. 2006. Cardiotrophin-1 induces interleukin-6 synthesis in human umbilical vein endothelial cells. Cytokine 36: 101-106.
18. Frombaum M, Therond P, Djelidi R, Beaudeux JL, Bonnefont-Rousselot D, Borderie D. 2011. Piceatannol is more effective than resveratrol in restoring endothelial cell dimethylarginine dimethylaminohydrolase expression and activity after highglucose oxidative stress. Free Radic Res 45: 293-302.
19. Goncharova EA, Ammit AJ, Irani C, et al. 2002. PI3K is required for proliferation and migration of human pulmonary vascular smooth muscle cells. Am J Physiol Lung Cell Mol Physiol 283: L354-363.
20. Huang X, Ordemann J, Muller JM, Dubiel W. 2012. The COP9 signalosome, cullin 3 and Keap1 supercomplex regulates CHOP stability and adipogenesis. Biol Open 1: 705-710.
21. Hung LM, Chen JK, Lee RS, Liang HC, Su MJ. 2001. Beneficial effects of astringinin, a resveratrol analogue, on the ischemia and reperfusion damage in rat heart. Free Radic Biol Med 30: 877-883.
22. Hur KY, Seo HJ, Kang ES, et al. 2008. Therapeutic effect of magnesium lithospermate B on neointimal formation after balloon-induced vascular injury. Eur J Pharmacol 586: 226-233.
23. Institute of Medicine. 2010. Promoting Cardiovascular Health in the Developing World: A Critical Challenge to Achieve Global Health, Fuster V, Kelly BB. The National Academies Press: Washington, DC.
24. Kalache A, Aboderin I, Hoskins I. 2002. Compression of morbidity and active ageing: key priorities for public health policy in the 21st century. Bull World Health Organ 80: 243-244.
25. Khurana R, Simons M, Martin JF, Zachary IC. 2005. Role of angiogenesis in cardiovascular disease: a critical appraisal. Circulation 112: 1813-1824.
26. Kim HJ, Lee KW, Kim MS, Lee HJ. 2008. Piceatannol attenuates hydrogen-peroxide-and peroxynitrite-induced apoptosis of PC12 cells by blocking down-regulation of Bcl-XL and activation of JNK. J Nutr Biochem 19: 459-466.
27. Kimura Y, Baba K, Okuda H. 2000. Inhibitory effects of active substances isolated from Cassia garrettiana heartwood on tumor growth and lung metastasis in Lewis lung carcinoma-bearing mice (Part 2). Anticancer Res 20: 2923-2930.
28. Kinoshita Y, Kawakami S, Yanae K, et al. 2013. Effect of long-term piceatannol treatment on eNOS levels in cultured endothelial cells. Biochem Biophys Res Commun 430: 1164-1168.
29. Kita Y, Miura Y, Yagasaki K. 2012. Antiproliferative and antiinvasive effect of piceatannol, a polyphenol present in grapes and wine, against hepatoma AH109A cells. J Biomed Biotechnol 2012: 672416.
30. Komiya A, Nagase H, Yamada H, et al. 2003. Concerted expression of eotaxin-1, eotaxin-2, and eotaxin-3 in human bronchial epithelial cells. Cell Immunol 225: 91-100.
31. Kwok CY,Wong CNY, Yau MYC, et al. 2010. Consumption of dried fruit of Crataegus pinnatifida (hawthorn) suppresses highcholesterol diet-induced hypercholesterolemia in rats. J Funct Foods 2: 179-186.
32. Lee CK, Lee HM, Kim HJ, et al. 2007. Syk contributes to PDGF-BB-mediated migration of rat aortic smooth muscle cells via MAPK pathways. Cardiovasc Res 74: 159-168.
33. Lee HH, Park SA, Almazari I, Kim EH, Na HK, Surh YJ. 2010. Piceatannol induces heme oxygenase-1 expression in human mammary epithelial cells through activation of ARE-driven Nrf2 signaling. Arch Biochem Biophys 501: 142-150.
34. Li J, Tang MS, Liu B, Shi X, Huang C. 2004. A critical role of PI-3K/ Akt/JNKs pathway in benzo[a]pyrene diol-epoxide (B[a]PDE)-induced AP-1 transactivation in mouse epidermal Cl41 cells. Oncogene 23: 3932-3944.
35. Li Q, Wu JH, Guo DJ, Cheng HL, Chen SL, Chan SW. 2009. Suppression of diet-induced hypercholesterolemia by scutellarin in rats. Planta Med 75: 1203-1208.
36. Libby P. 2002. Atherosclerosis: the new view. Sci Am 286: 46-55.
37. Marier JF, Vachon P, Gritsas A, Zhang J, Moreau JP, Ducharme MP. 2002. Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. J Pharmacol Exp Ther 302: 369-373.
38. Messiad H, Amira-Guebailia H, Houache O. 2013. Reversed phase high performance liquid chromatography used for the physicochemical and thermodynamic characterization of piceatannol/ beta-cyclodextrin complex. J Chromatogr B Analyt Technol Biomed Life Sci 926: 21-27.
39. Miksits M, Maier-Salamon A, Vo TP, et al. 2010. Glucuronidation of piceatannol by human liver microsomes: major role of UGT1A1, UGT1A8 and UGT1A10. J Pharm Pharmacol 62: 47-54.
40. Morabia A, Abel T. 2006. The WHO report "Preventing chronic diseases: a vital investment" and us. Soz Praventivmed 51: 74.
41. Murias M, Jager W, Handler N, et al. 2005. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. BiochemPharmacol 69: 903-912.
42. Nopo-Olazabal C, Hubstenberger J, Nopo-Olazabal L, Medina-Bolivar F. 2013. Antioxidant activity of selected stilbenoids and their bioproduction in hairy root cultures of muscadine grape (Vitis rotundifolia Michx.). J Agric Food Chem 61: 11744-11758.
43. Oh KS, Ryu SY, Kim YS, Lee BH. 2007. Large conductance Ca2 +-activated K+(BKCa) channels are involved in the vascular relaxations elicited by piceatannol isolated from Rheum undulatum rhizome. Planta Med 73: 1441-1446.
44. Ovesna Z, Kozics K, Bader Y, et al. 2006. Antioxidant activity of resveratrol, piceatannol and 3,3',4,4',5,5'-hexahydroxytrans-stilbene in three leukemia cell lines. Oncol Rep 16: 617-624.
45. Piotrowska H, Kucinska M, Murias M. 2012. Biological activity of piceatannol: leaving the shadow of resveratrol. Mutat Res 750: 60-82.
46. Potter GA, Patterson LH, Wanogho E, et al. 2002. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br J Cancer 86: 774-778.
47. Rhayem Y, Therond P, Camont L, et al. 2008. Chain-breaking activity of resveratrol and piceatannol in a linoleate micellar model. Chem Phys Lipids 155: 48-56.
48. Rimando AM, Kalt W, Magee JB, Dewey J, Ballington JR. 2004. Resveratrol, pterostilbene, and piceatannol in vaccinium berries. J Agric Food Chem 52: 4713-4719.
49. Rimando AM, Nagmani R, Feller DR, Yokoyama W. 2005. Pterostilbene, a new agonist for the peroxisome proliferatoractivated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J Agric Food Chem 53: 3403-3407.
50. Rokudai A, Terui Y, Kuniyoshi R, et al. 2006. Differential regulation of eotaxin-1/CCL11 and eotaxin-3/CCL26 production by the TNF-alpha and IL-4 stimulated human lung fibroblast. Biol Pharm Bull 29: 1102-1109.
51. Ross R. 1993. The pathogenesis of atherosclerosis: a perspective for the 1990s. Nature 362: 801-809.
52. Ross R. 1999. Atherosclerosis-an inflammatory disease. N Engl J Med 340: 115-126.
53. Roupe K, Teng XW, Fu X, Meadows GG, Davies NM. 2004. Determination of piceatannol in rat serum and liver microsomes: pharmacokinetics and phase I and II biotransformation. Biomed Chromatogr 18: 486-491.
54. Roupe KA, Remsberg CM, Yanez JA, Davies NM. 2006a. Pharmacometrics of stilbenes: seguing towards the clinic. Curr Clin Pharmacol 1: 81-101.
55. Roupe KA, Yanez JA, Teng XW, Davies NM. 2006b. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. J Pharm Pharmacol 58: 1443-1450.
56. Ruweler M, Gulden M, Maser E, Murias M, Seibert H. 2009. Cytotoxic, cytoprotective and antioxidant activities of resveratrol and analogues in C6 astroglioma cells in vitro. Chem Biol Interact 182: 128-135.
57. Sano S, Sugiyama K, Ito T, Katano Y, Ishihata A. 2011. Identification of the strong vasorelaxing substance scirpusin B, a dimer of piceatannol, from passion fruit (Passiflora edulis) seeds. J Agric Food Chem 59: 6209-6213.
58. Schaefer D, Meyer JE, Pods R, et al. 2006. Endothelial and epithelial expression of eotaxin-2 (CCL24) in nasal polyps. Int Arch Allergy Immunol 140: 205-214.
59. Seta Y, Shan K, Bozkurt B, Oral H, Mann DL. 1996. Basic mechanisms in heart failure: the cytokine hypothesis. J Card Fail 2: 243-249.
60. Seto SW, Lam TY, Tam HL, et al. 2009. Novel hypoglycemic effects of Ganoderma lucidum water-extract in obese/diabetic (+db/ +db) mice. Phytomedicine 16: 426-436.
61. Wan CW, Wong CN, Pin WK, et al. 2013. Chlorogenic acid exhibits cholesterol lowering and fatty liver attenuating properties by up-regulating the gene expression of PPAR-alpha in hypercholesterolemic rats induced with a high-cholesterol diet. Phytother Res 27: 545-551.
62. Wang L, Shah PK, Wang W, Song L, Yang M, Sharifi BG. 2013. Tenascin-C deficiency in apo E-/-mouse increases eotaxin levels: implications for atherosclerosis. Atherosclerosis 227: 267-274.
63. Wesolowska O, Kuzdzal M, Strancar J, Michalak K. 2009. Interaction of the chemopreventive agent resveratrol and its metabolite, piceatannol, with model membranes. Biochim Biophys Acta 1788: 1851-1860.
64. Willenberg I, Brauer W, Empl MT, Schebb NH. 2012. Development of a rapid LC-UV method for the investigation of chemical and metabolic stability of resveratrol oligomers. J Agric Food Chem 60: 7844-7850.
65. Woo A, Min B, Ryoo S. 2010. Piceatannol-3'-O-beta-D-glucopyranoside as an active component of rhubarb activates endothelial nitric oxide synthase through inhibition of arginase activity. Exp Mol Med 42: 524-532.
66. Woo A, Shin W, Cuong TD, et al. 2013. Arginase inhibition by piceatannol-3'-O-beta-D-glucopyranoside improves endothelial dysfunction via activation of endothelial nitric oxide synthase in ApoE-null mice fed a high-cholesterol diet. Int J Mol Med 31: 803-810.
67. Wung BS, Hsu MC, Wu CC, Hsieh CW. 2006. Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. Pharmacol Res 53: 113-122.
68. Yang CJ, Lin CY, Hsieh TC, Olson SC, Wu JM. 2011. Control of eotaxin-1 expression and release by resveratrol and its metabolites in culture human pulmonary artery endothelial cells. Am J Cardiovasc Dis 1: 16-30.
69. Yokozawa T, Kim YJ. 2007. Piceatannol inhibits melanogenesis by its antioxidative actions. Biol Pharm Bull 30: 2007-2011.
70. Yoo MY, Oh KS, Lee JW, et al. 2007. Vasorelaxant effect of stilbenes from rhizome extract of rhubarb (Rheum undulatum) on the contractility of rat aorta. Phytother Res 21: 186-189.
71. Zhan Y, Kim S, Izumi Y, et al. 2003. Role of JNK, p38, and ERK in platelet-derived growth factor-induced vascular proliferation, migration, and gene expression. Arterioscler Thromb Vasc Biol 23: 795-801.
72. Zou L, Sato N, Kone BC. 2004. Alpha-melanocyte stimulating hormone protects against H2O2-induced inhibition of wound restitution in IEC-6 cells via a Syk kinase-and NF-kappabetadependent mechanism. Shock 22: 453-459.