Inhibitory effects of caffeic acid ester analogues on free radicals and human liver microsome CYP1A2 activities

Medicinal Chemistry

Volumn 7, Issue 2, 2011, Pages 99-105

  Jaikang, Churdsak ^a   Chaiyasut, Chaiyavat ^a   Narongchai, Paitoon ^b   Niwatananun, Kanokporn ^a   Narongchai, Siripun ^b   Kusirisin, Winthana ^b  

^a CHIANG MAI UNIVERSITY   (Thailand)

^b Faculty of Medicine Chiang Mai University   (Thailand)

Author keywords

Caffeic acid ester analogues; Cancer chemoprevention; Cytochrome P4501A2; Enzyme inhibition; Ethyl caffeate; Free radical scavenging

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; BENZYL CAFFEATE; CAFFEIC ACID; CYTOCHROME P450 1A2; ETHYL CAFFEATE; FREE RADICAL; NITRIC OXIDE; OCTYL CAFFEATE; PHENACETIN; PHENACETIN O DEETHYLASE; PHENETHYL CAFFEATE; SUPEROXIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CANCER PREVENTION; CATALYSIS; DRUG SYNTHESIS; ENZYME KINETICS; HUMAN; HUMAN CELL; IC 50; LIVER MICROSOME; PRIORITY JOURNAL;

EID: 79952345436     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340611794859316     Document Type: Article

References (30)

1. Surh, Y.J. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutat. Res., 1999, 428, 305-327.
2. Hashizume, T.; Yoshitomi, S.; Asahi, S.; Matsumura, S.; Chatani, F.; Oda, H. In vitro micronucleus test in HepG2 transformants expressing a series of human cytochrome P450 isoforms with chemicals requiring metabolic activation. Mutat. Res., 2009, 677, 1-7.
3. Cheung, C.; Gonzalez, F.J. Humanized mouse lines and their application for prediction of human drug metabolism and toxicological risk assessment. J. Pharmacol. Exp. Ther., 2008, 327, 288-299.
4. Bozina, N.; Bradamante, V.; Lovric M. Genetic polymorphism of metabolic enzymes P450 (CYP) as a susceptibility factor for drug response, toxicity, and cancer risk. Arh. Hig. Rada. Toksikol., 2009, 60, 217-242.
5. Wang, B.; Zhou, S.F. Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr. Med. Chem., 2009, 16, 4066-4218.
6. Zhou, S.F; Chan, E.; Zhou, Z. W.; Xue, C. C.; Lai, X.; Duan, W. Insights into the structure, function, and regulation of human cytochrome P450 1A2. Curr. Drug Metab., 2009, 10, 713-729.
7. Gao, S.; Hu, M. Bioavailability challenges associated with development of anti-cancer phenolics. Mini Rev. Med. Chem., 2010, 10, 550-567.
8. Jaganathan, S.K.; Mandal, M. Antiproliferative effects of honey and of its polyphenols: a review. J. Biomed. Biotechnol., 2009, 2009, 830-616.
9. Manda, G.; Nechifor, M.T.; Neagu, T.M. Reactive oxygen species, cancer and anti-cancer therapies. Curr. Chem. Biol., 2009, 3, 342-366.
10. Choi, K.; Kim, J.; Kim, G.W.; Choi, C. Oxidative stress-induced necrotic cell death via mitochondira-dependent burst of reactive oxygen species. Curr. Neurovasc. Res., 2009, 6, 213-222.
11. Pandey, K.B.; Rizvi, S.I. Current understanding of dietary polyphenols and their role in health and disease. Curr. Nutrit. Food. Sci., 2009, 5, 249-263.
12. Kusirisin, W.; Srichairatanakool, S.; Lerttrakarnnon, P.; Lailerd, N.; Suttajit, M.; Jaikang, C.; Chaiyasut, C. Antioxidative activity, polyphenolic content and anti-glycation effect of some Thai medicinal plants traditionally used in diabetic patients. Med. Chem., 2009, 5, 139-147.
13. Hirose, M.; Takahashi, S.; Ogawa, K.; Futakuchi, M.; Shirai, T.; Shibutani, M.; Uneyama, C.; Toyoda, K.; Iwata, H. Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats. Cancer Lett., 1999, 143, 173-178. (Pubitemid 29392952)
14. Son, S.; Lewis, B.A. Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure-activity relationship. J. Agric. Food Chem., 2002, 50, 468-472. (Pubitemid 34106663)
15. Jiang, R.W.; Lau, K. M.; Hon, P.M.; Mak, T.C.; Woo, K.S.; Fung, K.P. Chemistry and biological activities of caffeic acid derivatives from Salvia miltiorrhiza. Curr. Med. Chem., 2005, 12, 237-246. (Pubitemid 40089836)
16. Uwai, K.; Osanai, Y.; Imaizumi, T.; Kanno, S.; Takeshita M.; Ishikawa, M. Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. Bioorgan. Med. Chem., 2008, 16, 7795-7803.
17. Jaikang, C.; Chaiyasut, C. Caffeic acid and its derivatives as heme oxygenase 1 inducer in Hep G2 cell line. J. Med. Plants. Res., 2010, 4, 940-946
18. Lee, Y.T.; Don, M.J.; Liao, C.H.; Chiou, H.W.; Chen, C.F.; Ho, L.K. Effects of phenolic acid esters and amides on stimulusinduced reactive oxygen species production in human neutrophils. Clin. Chim. Acta, 2005, 352, 135-141.
19. GÜlin, I.; Mshvildadze, V.; Gepdiremen, A.; Elias, R. Screening of antiradical and antioxidant activity of monodesmosides and crude extract from Leontice smirnowii tuber. Phytomedicine, 2006, 13, 343-351. (Pubitemid 44382442)
20. Govindarajan, R.; Vijayakumar, M.; Rao, C.V.; Shirwaikar, A.; Rawat, A.K.; Mehrotra, S.; Pushpangadan, P. Antioxidant potential of Anogeissus latifolia. Biol. Pharm. Bull., 2004, 27, 1266-1269. (Pubitemid 41701724)
21. Shon, M.Y.; Kim, T.H.; Sung, N.J. Antioxidants and free radical scavenging activity of Phellinus baumii (Phellinus of Hymenochaetaceae) extracts. Food Chem., 2003, 82, 593-597.
22. Banerjee, A.; Dasgupta, N.; De, B. In vitro study of antioxidant activity of Syzygium cumini fruit. Food Chem., 2005, 90, 727-733. (Pubitemid 39424039)
23. Kusirisin, W.; Jaikang, C.; Chaiyasut, C.; Narongchai, P. Effect of polyphenolic compounds from Solanum torvum on plasma lipid peroxidation, superoxide anion and cytochrome P450 2E1 in human liver microsomes. Med. Chem., 2009, 5, 583-588.
24. Taubert, D.; Breitenbach, T. Lazar, A.; Censarek, P.; Harlfinger, S.; Berkels, R.; Klaus, W.; Roesen, R. Reaction rate constants of superoxide scavenging by plant antioxidants. Free Radic. Biol. Med., 2003, 35, 1599-1607. (Pubitemid 37532911)
25. Ardestani, A.; Yazdanparast, R. Antioxidant and free radical scavenging potential of Achillea santolina extracts. Food Chem., 2007, 104, 21-29. (Pubitemid 46561097)
26. Yen, G.C.; Lai, H.H.; Chou, H. Y. Nitric oxide-scavenging and antioxidant effects of Uraria crinita root. Food Chem., 2001, 74, 471-478.
27. Hsu, B.; Coupar, I.M.; Ng, K. Antioxidant activity of hot water extract from the fruit of the Doum palm, Hyphaene thebaica. Food Chem., 2006, 98, 317-328.
28. Letelier, M.E.; Molina-Berros, A.; Corts-Troncoso, J.; Jara-Sandoval, J.; Holst, M.; Palma, K.; Montoya, M.; Miranda, D.; Gonzlez-Lira, V. DPPH and oxygen free radicals as pro-oxidant of biomolecules. Toxicol. In Vitro, 2008, 22, 279-286.
29. Moon, J.H.; Terao, J. Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food Chem., 1998, 46, 5062-5065. (Pubitemid 128488258)
30. Beltran-Ramirez, O.; Aleman-Lazarini, L.; Salcido-Neyoy, M.; Hernandez-Garcia, S.; Fattel-Fazenda, S.; Arce-Popoca, E.; Arellanes-Robledo, J.; Garcia-Roman, R.; Vazquez-Vazquez, P.; Sierra-Santoyo, A.; Villa-Trevino, S. Evidence that the anticarcinogenic effect of caffeic acid phenethyl ester in the resistant hepatocyte model involves modifications of cytochrome P450. Toxicol. Sci., 2008, 104, 100-106. (Pubitemid 351859032)