Protective Effects of Resveratrol and its Analogues against Free Radical-Induced Oxidative Hemolysis of Red Blood Cells†
Jian-Guo Fang
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorMan Lu
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorLan-Ping Ma
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorLi Yang
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorLong-Min Wu
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorZhong-Li Liu
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorJian-Guo Fang
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorMan Lu
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorLan-Ping Ma
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorLi Yang
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorLong-Min Wu
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorZhong-Li Liu
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorAbstract
The in vitro oxidative hemolysis of human red blood cells (RBCs) was used as a model to study the free radical-induced damage of biological membranes and the protective effect of resveratrol (3,5,4′-trihydroxy-trans-stilbene, 1) and its analogues, i. e., 4-hydroxy-trans-stilbene (2), 3, 5-dihydroxytrans-stilbene (3), 3,4-dihydroxy-trans-stilbene (4), 4,4′-dihydroxy-trans-stilbene (5) and 2, 4, 4′-trihydroxy-trans-stilbene (6). The hemolysis of RBCs was induced by a water-soluble free radical initiator 2, 2′-azobis (2-amidinopropane hydrochloride) (AAPH). It was found that addition of AAPH at 37 °C to the suspension of RBCs caused fast hemolysis after a short period of inhibition period, and addition of 1–6 significantly suppressed the hemolysis. Compound 4 which bears an ortho-dihydroxyl functionality showed much more effective anti-hemolysis activity than that of resveratrol and the other analogues.
References
- 1(a) Soleas, G. J.; Diamandis, E. P.; Goldberg, D. M. CUn. Biochem. 1997, 30, 91. (b) Sieman, E. H.; Creasy, L. L. Am. J. Enol. Vitic. 1992, 43, 49. (c) Corder, R.; Douthwaite, J. A.; Lees, D. M.; Khan, N. Q.; Santos, A. C. V. D.; Wood, E. G. M.; Carrier, J. Nature 2001, 414, 863.
- 2(a) Jang, M. S.; Cai, E. N.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Famsworth, N. R.; Kinghom, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218. (b) Domianaki, A.; Bakogeorgou, E.; Kampa, M.; Notas, G.; Hatzoglou, A.; Panagiotou, S.; Gemetzi, C.; Kouroumalis, E.; Martin, P. M.; Castanas, E. J. Cell. Biochem. 2000, 78, 429. (c) Jang, M.; Pezzuto, J. M. Drugs Exp. Clin. Res. 1999, 25, 65. (d) Sgamboto, A.; Ardito, R.; Faraglia, B.; Boninsegna, A.; Wolf, F. I.; Cittadini, A. Mutat. Res. 2001, 496, 171. (e) Schneider, Y.; Vincent, F.; Duranton, B.; Bodolo, L.; Gosse, F.; Bergmann, C.; Seiler, N.; Raul, F. Cancer Lett. 2000, 158, 85. (f) Surh, Y. J.; Hurh, Y. J.; Kang, J. Y.; Lee, E.; Kong, G.; Lee, S. J. Cancer Lett. 1999, 140, 1.
- 3(a) Rotondo, S.; Rajtar, G.; Manarinl, S.; Celardo, A.; Rotilio, D.; Gaetano, G.; Evangelists, V.; Cerletti, C. Br. J. Pharmacol. 1998, 123, 1691. (b) Jang, D. S.; Kang, B. S.; Ryu, S. Y.; Chang, J. M.; Min, K. R.; Kim, Y. Biochem. Pharmacol. 1999, 57, 705.
- 4 Ruf, J. C. Drugs Exp. CUn. Res. 1999, 25, 125.
- 5 Matsuda, H.; Tomohiro, N.; Hiraba, K.; Harima, S.; Ko, S.; Matsuo, K.; Yoshikawa, M.; Kuno, M. Biol. Pharm. Bull. 2001, 24, 264.
- 6(a) Stivala, L. A.; Savio, M.; Carafoli, P.; Perucca, P.; Bianchi, L.; Maga, G.; Forti, L.; Pagnoni, U. M.; Albini, A.; Prosperi, E.; Vannini, V. J. Biol. Chem. 2001, 276, 22586. (b) Burkitt, M. J.; Duncan, J. Arch. Biochem. Biophys. 2000, 381, 253. (c) Tadolini, B.; Julian, C.; Piu, L.; Franconi, F.; Cabrini, L. Free Radical Res. 2000, 33, 105. (d) Seybert, D. M.; Milnar, C. M. Free Radical Biol. Med. 1998, 25, Suppl. 1, 85. (e) Pinto, M. C.; Garcina-Barrado, J. A.; Macias, P. J. Agric. Food Chem. 1999, 47, 4842. (f) Hung, L. M.; Chen, J. K.; Huang, S. S.; Lee, R. S.; Su, M. J. Cardiovasc. Res. 2000, 47, 549.
- 7(a) Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3 Ed., Oxford Univ. Press, London, 1999. (b) Forsberg, L.; Fair, U.; Morgenstem, R. Arch. Biochem. Biophys. 2001, 381, 84. (c) Mamett, L. J. Carcinogenesis 2000, 21, 361. (d) Esterbauer, H.; Ramos, P. Rev. Physiol., Biochem. Pharmacol. 1995, 127, 31.
- 8 Tedesco, I.; Risso, M.; Russo, P.; Iacomino, G.; Rus-so, G. L.; Carraturo, A.; Faruolo, C.; Moio, L.; Palumbo, R. J. Nutr. Biochem. 2000, 11, 114.
- 9(a) Chen, Z. H.; Zhou, B.; Yang, L.; Wu, L. M.; Liu, Z. L. J. Chem. Soc., Perkin Trans. 2 2001, 1835. (b) Liu, Z. Q.; Ma, L. P.; Zhou, B.; Yang, L.; Liu, Z. L. Chem. Phys. Lipids 2000, 106, 53.
- 10(a) Yu, W.; Liu, Z. Q.; Liu, Z. L. J. Chem. Soc., Perkin Trans. 2 1999, 969. (b) Liu, Z. Q.; Yu, W.; Liu, Z. L. Chem. Phys. Lipids 1999, 705, 125.
- 11 Zhou, B.; Chen, Z.; Chen, Y.; Jia, Z.; Jia, Y.; Zeng, L.; Wu, L. M.; Yang, L.; Liu, Z. L. Appl. Magn. Reson. 2000, 18, 397.
- 12(a) Ma, L. P.; Liu, Z. Q.; Zhou, B.; Yang, L.; Liu, Z. L. Chin. Sci. Bull. 2000, 45, 2052. (b) Nike, E.; Komuro, E.; Takahashi, M.; Urano, S.; Ito, E.; Texao, K. J. Biol. Chem. 1988, 263, 19809.
- 13(a) Thakkar, K.; Geahlen, R. L.; Cushman, M. J. Med. Chem. 1993, 36, 2950. (b) Bachelor, F. W.; Loman, A. A.; Snowdon, I. R. Can. J. Chem. 1970, 48, 1554.
- 14 Kuang, Z. H.; Wang, P. F.; Zheng, R. L.; Liu, Z. L.; Liu, Y. C. Chem. Phys. Lipids 1994, 71, 95.
- 15 Bowry, V. W.; Stacker, R. J. Am. Chem. Soc. 1993, 115, 6029.
- 16
Fang, J. G.;
Lu, M.;
Chen, Z. H.;
Zhu, H. H.;
Li, Y.;
Yang, L.;
Wu, L. M.;
Liu, Z. L.
Chem. Eur. J.
2002,
8,
4191.
10.1002/1521-3765(20020916)8:18<4191::AID-CHEM4191>3.0.CO;2-S CAS PubMed Web of Science® Google Scholar
- 17 Foti, M.; Ruberto, G. J. Agric. Food Chem. 2001, 49, 342.
- 18 Wright, J. S.; Johnson, E. R.; DiLabio, G. A. J. Am. Chem. Soc. 2001, 123, 1173.
- 19 Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194.
- 20 Liu, Y. C.; Liu, Z. L.; Han, Z. X. Rev. Chem. Intermed. 1988, 10, 269.