Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor α-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 9, 2005, Pages 3403-3407

  Rimando, Agnes M ^a   Nagmani, Rangaswamy ^b   Feller, Dennis R ^c   Yokoyama, Wallace ^d  

^a NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

^b Enzymatic Therapy Inc   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d WESTERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

Cholesterol; Lipoprotein; PPAR ; Pterostilbene

Indexed keywords

ACYL COENZYME A OXIDASE; CHOLESTEROL; HYBRID PROTEIN; LIPOPROTEIN; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PHENOL DERIVATIVE; PTEROSTILBENE; STILBENE DERIVATIVE;

ANIMAL; ARTICLE; BLOOD; CELL CULTURE; DNA RESPONSIVE ELEMENT; DRUG POTENTIATION; GENETIC TRANSFECTION; GENETICS; HAMSTER; HYPERCHOLESTEROLEMIA; LIVER TUMOR; MALE; RAT; SYRIAN HAMSTER;

ACYL-COA OXIDASE; ANIMALS; CHOLESTEROL; CRICETINAE; HYPERCHOLESTEROLEMIA; LIPOPROTEINS; LIVER NEOPLASMS, EXPERIMENTAL; MALE; MESOCRICETUS; PHENOLS; PPAR ALPHA; RATS; RECOMBINANT FUSION PROTEINS; RESPONSE ELEMENTS; STILBENES; TRANSFECTION; TUMOR CELLS, CULTURED;

ANIMALIA; ARACHIS HYPOGAEA; CRICETINAE; VITACEAE; VITIS SP.;

EID: 19944410516     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0580364     Document Type: Article

References (40)

1. Dreyer, C.; Krey, G.; Keller, H.; Givel, F.; Helftenbein, G.; Wahli, W. Control of the peroxisomal β-oxidation pathway by a novel family of nuclear hormone receptors. Cell 1992, 68, 879-87.
2. Tugwood, J. D.; Aldridge, T. C.; Lambe, K. G.; Macdonald, N.; Woodyatt, N. J. Peroxisome proliferator-activated receptors: Structures and function. Ann. N. Y. Acad. Sci. 1996, 804, 252-265.
3. Chakrabarti, R.; Rajagopalan, R. The role of PPARs in obesity and other insulin resistance associated disorders. Curr. Med. Chem.: Immunol. Endocr. Metab. Agents 2004, 4, 67-73.
4. Escher, P.; Wahli, W. Peroxisome proliferator-activated receptors: Insight into multiple cellular functions. Mutat. Res. 2000, 448, 121-138.
5. Mudaliar, S.; Henry, R. R. PPAR agonists in health and disease: A pathophysiologic and clinical overview. Curr. Opin. Endocrinol. Diabetes 2002, 9, 285-302.
6. Fruchart, J.-C.; Staels, B.; Duriez, P. PPAR-alpha in lipid and lipoprotein metabolism, vascular inflammation and atherosclerosis. Prog. Exp. Cardiol. 2003, 8, 3-16.
7. Gilde, A. J.; Van Bilsen, M. Peroxisome proliferator-activated receptors (PPARS): Regulators of gene expression in heart and skeletal muscle. Acta Physiol. Scand. 2003, 178, 425-434.
8. Fruchart, J.-C.; Duriez, P. Anti-cholesterol agents, new therapeutic approaches. Ann. Pharm. Fr. 2004, 62, 3-18.
9. Gervois, P.; Torra, I. P.; Fruchart, J.-C.; Staels, B. Regulation of lipid and lipoprotein metabolism by PPAR activators. Clin. Chem. Lab. Med. 2000, 38, 3-11.
10. Kersten, S.; Mandard, S.; Escher, P.; Gonzalez, F. J.; Tafuri, S.; Desvergne, B.; Wahli, W. The peroxisome proliferator-activated receptor a regulates amino acid metabolism. FASEB 2001, 15, 1971-1978.
11. Stivala, L. A.; Savio, M.; Fedarico, C.; Perucca, P.; Bianchi, L.; Magas, G.; Forti, L.; Pagnoni, U. M.; Albini, A.; Prosperi, E.; Vannini, V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem. 2001, 276, 22586-22594.
12. Teguo, P. W.; Fauconneau, B.; Deffieux, G.; Huguet, F.; Vercauteren, J.; Mérillon, J.-M. Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell cultures. J. Nat. Prod. 1998, 61, 655-657.
13. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
14. Hegsted, D. M.; Ausman, L. M. Diet, alcohol and coronary heart disease in man. J. Nutr. 1988, 118, 1184-1189.
15. Renaud, S.; De Lorgeril, M. Wine, alcohol, and the French paradox for coronary heart disease. Lancet 1992, 339, 1523.
16. Miura, D.; Miura, Y.; Yagasaki, K. Hypolipidemic action of dietary resveratrol, a phytoalexin in grapes and red wine, in hepatoma-bearing rats. Life Sci. 2003, 73, 1393-400.
17. Rimando, A. M.; Cuendet, M.; Desmarchelier, C.; Mehta, R. G.; Pezzuto, J. M.; Duke, S. O. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. J. Agric. Food Chem. 2002, 50, 3453-3457.
18. Manickam, M.; Ramanathan, M.; Jahromi, M. A. F.; Chansouria, J. P. N.; Ray, A. B. Antihyperglycemic activity of phenolics from Pterocarpus marsupium. J. Nat. Prod. 1997, 60, 609-610.
19. Rimando, A. M.; Pezzuto, J. M.; Farnsworth, N. R.; Santisuk, T.; Reutrakul, V. Revision of the NMR assignments of pterostilbene and dihydrodehydro-diconiferyl alcohol: Cytotoxic constituents from Anogeissus acuminata. Nat. Prod. Lett. 1994, 4, 267-272.
20. 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.
21. Waffo-Teguo, P.; 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. Nutr. Cancer 2001, 40, 173-179.
22. Hung, L. M.; Chen, J.-K.; Lee, R.-S.; Liang, H.-C; Su, M.-J. Beneficial effects of astringinin, a resveratrol analogue, on the ischemia and reperfusion damage in rat heart. Free Radical Biol. Med. 2001, 30, 877-883.
23. Lee, S. K.; Mbwambo, Z. H.; Chung, H.; Luyengi, L.; Gamez, E. J. C.; Mehta, R. G.; Kinghorn, A. D.; Pezzuto, J. M. Evaluation of the antioxidant potential of natural products. Comb. Chem. High Throughput Screen. 1998, 1, 35-46.
24. Matsuda, H.; Tomohiro, N.; Hiraba, K.; Harima, S.; Ko, S.; Matsuo, K.; Yoshikawa, M.; Kubo, M. 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). Biol. Pharm. Bull. 2001, 24, 264-267.
25. Lee, S. K.; Nam, K. A.; Hoe, Y. H.; Min, H.-Y.; Kim, E.-Y.; Ko, H.; Song, S.; Lee, T.; Kim, S. Synthesis and evaluation of cytotoxicity of stilbene analogues. Arch. Pharm. Res. 2003, 26, 253-257.
26. Inoue, H.; Jiang, X.-F.; 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, 203-206.
27. Jaradat, M. S.; Noonan, D. J.; Wu, B.; Feller, D. R. Pseudolaric acid analogues as a new class of peroxisomal proliferator-activated receptor agonists. Planta Med. 2002, 68, 667-671.
28. German, J.; Xu, R.; Walzern, R.; Kinsella, J.; Nakamura, M.; Yokoyama, W. Effect of dietary fats and barley fiber on total cholesterol and lipoprotein cholesterol distribution in plasma of hamsters. Nutr. Res. 1996, 16, 1239-1249.
29. Akbiyik, F.; Ray, D.; Bozkaya, H.; Demirpence, E. Ligand- and species-dependent activation of PPARalpha. Cell Physiol. Biochem. 2004, 14, 269-276.
30. Choudhury, A. I.; Sims, H. M.; Horley, N. J.; Roberts, R. A.; Tomlinson, S. R.; Salter, A. M.; Bruce, M.; Shaw, P. N.; Kendall, D.; Barrett, D. A.; Bell, D. R. Molecular analysis of peroxisome proliferation in the hamster. Toxicol. Appl. Pharmacol. 2004, 197, 9-18.
31. Wang, P.-R.; Guo, Q.; Ippolito, M.; Wu, M.; Milot, D.; Ventre, J.; Doebber, T.; Wright, S. D.; Chao, Y.-S. High fat fed hamster, a unique animal model for treatment of diabetic dyslipidemia with peroxisome proliferator activated receptor alpha selective agonists. Eur. J. Pharm. 2001, 427, 285-293.
32. Rizvi, F.; Puri, A.; Bhatia, G.; Khanna, A. K.; Wulff, E. M.; Rastogi, A. K.; Chander, R. Antidyslipidemic action of fenofibrate in dyslipidemic-diabetic hamster model. Biochem. Biophys. Res. Commun. 2003, 305, 215-222.
33. Kollar, P.; Kotolova, H.; Necas, J.; Karpisek, M.; Bartosikova, L.; Karesova, P. Experimental study of resveratrol and flavonoids in red wine with regard to their possible hypolipidemic effect. Vnitrni Lekarstvi 2000, 46, 856-860.
34. Wilson, T.; Knight, T. J.; Beits, D. C.; Lewis, D. S.; Engen, R. L. Resveratrol promotes atherosclerosis in hypercholesterolemic rabbits. Life Sci. 1996, 59, 15-21.
35. Wu, J. M.; Lu, X.; Guo, J.; Hsieh, T.-C. In Phytochemicals: Mechanisms of Action; Meskin, M. S., Bidlack, W. R., Davies, A. J., Lewis, D. S., Randolph, R. K., Eds.; CRC Press LLC: Boca Raton, FL, 2003; pp 145-161.
36. Roberts, R. A.; Moffat, G. J. Biology and toxicology of PPARα ligands- The hypolipidemic fibrate peroxisome proliferators. Commun. Toxicol. 2001, 7, 259-273.
37. Adrian, M.; Jeandet, P.; Douillet-Breuil, A. C.; Bessis, R. Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation. J. Agric. Food Chem. 2000, 48, 6103-6105.
38. Rimando, A. M.; Magee, J.; Kalt, W.; Ballington, J. Resveratrol, pterostilbene and piceatannol in Vaccinium berries. J. Agric. Food Chem. 2004, 52, 4713-4719.
39. Maurya, R.; Ray, A. B.; Duah, F. K.; Slatkin, D. J.; Schiff, P. L., Jr. Constituents of Pterocarpus marsupium. J. Nat. Prod. 1984, 47, 179-81.
40. Arnone, A.; Camarda, L.; Merlini, L.; Nasini, G.; Taylor, D. A. H. Coloring matters of the West African red woods Pterocarpus osun and P. soyauxii. Structures of santarubins A and B. J. Chem. Soc., Perkins Trans. 1 1977, 19, 2116-2118.