Kinetics and antioxidative sites of capsaicin in homogeneous solution

JAOCS, Journal of the American Oil Chemists' Society

Volumn 87, Issue 12, 2010, Pages 1397-1405

  Okada, Youji ^a   Tanaka, Kaoru ^a   Sato, Eisuke ^b   Okajima, Haruo ^a  

^a KYORIN UNIVERSITY   (Japan)

^b AOMORI UNIVERSITY   (Japan)

Author keywords

Antioxidative site; Capsaicin; DPPH; Peroxyl radical; Phenolic OH group; Rate constant

Indexed keywords

ANTIOXIDATIVE SITE; CAPSAICIN; DPPH; PEROXYL RADICAL; PHENOLIC OH GROUP;

ACETONE; ACETONITRILE; METHANOL; ORGANIC SOLVENTS; RATE CONSTANTS;

PHENOLS;

EID: 78650594648     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-010-1628-4     Document Type: Article

References (30)

1. Frankel EN (1995) Natural and biological antioxidants in foods and biological systems. Their mechanism of action, applications and implications. Lipid Technol 77-88
2. Nakatani N (1996) Antioxidants from spices and herbs. In: Shahidi F (ed) Natural antioxidants-chemistry, health effects, and applications. AOCS press, Champaign, pp 64-75
3. AK De JJ Ghosh 1989 Capsaicin pretreatment protects free radical induced rat lung damage on exposure to gaseous chemical lung irritants Phytother Res 3 159 161 1:CAS:528:DyaL1MXlvV2is7s%3D 10.1002/ptr.2650030411
4. AK De JJ Ghosh 1992 Studies on capsaicin inhibition of chemically induced lipid peroxidation in the lung and liver tissues of rat Phytother Res 6 34 37 1:CAS:528:DyaK38XhvVyjsL8%3D 10.1002/ptr.2650060109
5. AC Pulla Reddy BR Lokesh 1992 Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat liver microsomes Mol Cell Biochem 111 117 124 10.1007/BF00229582
6. A Asai K Nakagawa T Miyazawa 1999 Antioxidative effects of turmeric, rosemary and capsicum extracts on membrane phospholipid peroxidation and liver lipid metabolism in mice Biosci Biotechnol Biochem 63 2118 2122 1:CAS:528:DC%2BD3cXlsFKlsQ%3D%3D 10.1271/bbb.63.2118
7. Y Okada H Okajima 2001 Antioxidant effect of capsaicin on lipid peroxidation in homogeneous solution, micelle dispersions and liposomal membranes Redox Rep 6 117 122 1:CAS:528:DC%2BD3MXlt12gur4%3D 10.1179/135100001101536120 (Pubitemid 32519819)
8. Y Okada H Okajima Y Shima H Ohta 2002 Hydroxyl radical scavenging action of capsaicin Redox Rep 7 153 157 1:CAS:528:DC%2BD38Xmt1aht78%3D 10.1179/135100002125000398 (Pubitemid 34700439)
9. K Kogure S Goto M Nishimura M Yasumoto K Abe C Ohiwa H Sassa T Kusumi H Terada 2002 Mechanism of potent antiperoxidative effect of capsaicin Biochim Biophys Acta 1573 84 92 1:CAS:528:DC%2BD38Xns1agsr8%3D
10. S Saito J Kawabata 2005 Effect of electron-withdrawing substituents on DPPH radical scavenging of protocatechuic acid and its analogues in alcoholic solvents Tetrahedron 61 8101 8108 1:CAS:528:DC%2BD2MXmtlGqtL0%3D 10.1016/j.tet.2005.06.040 (Pubitemid 41019133)
11. S Saito J Kawabata 2006 DPPH (=2, 2-diphenyl-1-picrylhydrazyl) radical-scavenging reaction of protocatechuic acid (=3, 4-dihydroxybenzoic acid): Difference in reactivity between acids and their esters Helv Chim Acta 89 1395 1407 1:CAS:528:DC%2BD28Xotleisr4%3D 10.1002/hlca.200690139 (Pubitemid 44196365)
12. G Litwinienko KU Ingold 2003 Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2, 2-diphenyl-1-picrylhydrazyl (dpph•) in alcohols J Org Chem 68 3433 3438 1:CAS:528:DC%2BD3sXisFWhu7s%3D 10.1021/jo026917t (Pubitemid 36520361)
13. G Litwinienko KU Ingold 2004 Abnormal solvent effects on hydrogen atom abstractions. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer J Org Chem 69 5888 5896 1:CAS:528:DC%2BD2cXmt1Kju70%3D 10.1021/jo049254j (Pubitemid 39145667)
14. G Litwinienko KU Ingold 2007 Solvent effects on the rates and mechanisms of reaction of phenols with free radicals Acc Chem Res 40 222 230 1:CAS:528:DC%2BD2sXltVehug%3D%3D 10.1021/ar0682029
15. MC Foti C Daquino C Geraci 2004 Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH• radical in alcoholic solutions J Org Chem 69 2309 2314 1:CAS:528:DC%2BD2cXhsFyhsbs%3D 10.1021/jo035758q (Pubitemid 38419039)
16. N Hashimoto T Aoyama T Shioiri 1981 New methods and reagents in organic synthesis. 14. A simple efficient preparation of methyl esters with trimethylsilyldiazomethane (TMSCHN2) and its application to gas chromatographic analysis of fatty acids Chem Pharm Bull 29 1475 1478 1:CAS:528: DyaL3MXkvFSmt7w%3D
17. Y Okada K Tanaka E Sato H Okajima 2006 Kinetic and mechanistic studies of allicin as an antioxidant Org Biomol Chem 4 4113 4117 1:CAS:528: DC%2BD28XhtFKitr%2FJ 10.1039/b611506c (Pubitemid 44665181)
18. Y Okada K Tanaka E Sato H Okajima 2008 Antioxidant activity of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate, from Petiveria alliacea L. Org Biomol Chem 6 1097 1102 1:CAS:528:DC%2BD1cXjtVCjtbg%3D 10.1039/b715727d
19. J-Y Feng Z-Q Liu 2009 Phenolic and enolic hydroxyl groups in curcumin: which plays the major role in scavenging radicals? J Agric Food Chem 57 11041 11046 1:CAS:528:DC%2BD1MXhtV2murnK 10.1021/jf902244g
20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, revision C. 02. Gaussian, Inc., Pittsburgh
21. LL Chepelev CS Beshara PD Maclean GL Hatfield AA Rand A Thompson JS Wright LRC Barclay 2006 Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures J Org Chem 71 22 30 1:CAS:528:DC%2BD2MXht1GjurfI 10.1021/jo051359e (Pubitemid 43128054)
22. GW Burton KU Ingold 1986 Vitamin E: application of the principles of physical organic chemistry to the exploration of its structure and function Acc Chem Res 19 194 201 1:CAS:528:DyaL28XltFeqtbk%3D 10.1021/ar00127a001
23. O Dangks C Dufour G Fargeix 2000 Inhibition of lipid peroxidation by quercetin and quercetin derivatives: antioxidant and prooxidant effects J Chem Soc Perkin Trans 2 1215 1222
24. WA Pryor JA Cornicelli LJ Devall B Tait BK Trivedi DT Witiak M Wu 1993 A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants J Org Chem 58 3521 3532 1:CAS:528:DyaK3sXlt1GgsLo%3D 10.1021/jo00065a013
25. L Landi D Fiorentini C Stefanelli P Pasquali GF Pednlli 1990 Inhibition of autoxidation of egg yolk phosphatidylcholine in homogeneous solution and in liposomes by oxidized ubiquinone Biochim Biophys Acta 1028 223 228 1:CAS:528:DyaK3MXjslyksg%3D%3D 10.1016/0005-2736(90)90170-S (Pubitemid 20318025)
26. LRC Barclay KU Ingold 1981 Autoxidation of biological molecules. 2. Autoxidation of a model membrane. Comparison of the autoxidation of egg lecithin phosphatidylcholine in water and in chlorobenzene J Am Chem Soc 103 6478 6485 1:CAS:528:DyaL3MXls1Chur4%3D 10.1021/ja00411a036
27. E Niki 1987 Antioxidants in relation to lipid peroxidation Chem Phys Lipids 44 227 253 1:CAS:528:DyaL2sXmt1yhtLY%3D 10.1016/0009-3084(87)90052-1
28. HH Hussain G Babic T Durst JS Wright M Flueraru A Chichirau LL Chepelev 2003 Development of novel antioxidants: design, synthesis, and reactivity J Org Chem 68 7023 7032 1:CAS:528:DC%2BD3sXmsVehu78%3D 10.1021/jo0301090 (Pubitemid 37071783)
29. V Thavasi RPA Bettens LP Leong 2009 Temperature and solvent effects on radical scavenging ability of phenols J Phys Chem A 113 3068 3077 1:CAS:528:DC%2BD1MXivVeit7w%3D 10.1021/jp806679v
30. L López-Giraldo M Laguerre J Lecomte M-C Figueroa-Espinoza B Barea J Weiss EA Decker P Villeneuve 2009 Kinetic and stoichiometry of the reaction of chlorogenic acid its alkyl esters against the DPPH radical J Agric Food Chem 57 863 870 10.1021/jf803148z