Antioxidant activity of bakuchiol: Experimental evidences and theoretical treatments on the possible involvement of the terpenoid chain

Chemical Research in Toxicology

Volumn 16, Issue 9, 2003, Pages 1062-1069

  Adhikari, S ^a   Joshi, R ^a   Patro, B S ^a   Ghanty, T K ^a   Chintalwar, G J ^a   Sharma, A ^a   Chattopadhyay, S ^a   Mukherjee, T ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; BAKUCHIOL; MEROTERPENE; PEROXY RADICAL; PLANT EXTRACT; TERPENE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; LIPID PEROXIDATION; OXIDATION; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTIOXIDANTS; BRAIN; BRAIN CHEMISTRY; CALORIMETRY; DRUGS, CHINESE HERBAL; FREE RADICAL SCAVENGERS; FREE RADICALS; LINOLEIC ACIDS; LIPID PEROXIDATION; PHENOLS; PICRATES; PROTEINS; PSORALEA; PULSE RADIOLYSIS; RATS; RATS, WISTAR; SEEDS; TERPENES;

EID: 0141831739     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034082r     Document Type: Article

References (52)

1. Potterat, O. (1997) Antioxidants and free radical scavengers of natural origin. Curr. Org. Chem. 1, 415-440.
2. (a) Bors, W., Heller, W., Michel, C., and Stettmaier, K. (1996) Flavonoids and Polyphenols: Chemistry and Biology. Handbook of Antioxidants (Cadenas, E., and Parker, L., Eds.) pp 409-466, Marcel Dekker, New York.
3. (b) Rice-Evans, C. (1995) Plant polyphenols: free radical scavengers or chain-breaking antioxidants? Biochem. Soc. Symp. 61, 103-116.
4. (a) Wright, J. S., Johnson, E. R., and DiLabio, G. A. (2001) Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants. J. Am. Chem. Soc. 123, 1173-1183.
5. (b) Pratt, D. A., Dilabio, G. A., Brigati, G., Pedulli, G. F., and Valmigli, I. (2001) 5-Pyrimidinols: Novel chain breaking antioxidants. More effective than phenols. J. Am. Chem. Soc. 123, 4625-4626.
6. (c) Sun, Y.-M., Zhang, H.-Y., Chen, D.-Z., and Liu, C.-B. (2002) Theoretical elucidation on the antioxidant mechanism of curcumin: A DFT study. Org. Lett. 4, 2909-2911.
7. (a) Jovanovic, S. V., Steenken, S., Boone, C. W., and Simic, M. G. (1999) H-atom transfer is a preferred antioxidant mechanism of curcumin. J. Am. Chem. Soc. 121, 9677-9681.
8. (b) Patro, B. S., Rele, S., Chintalwar, G. J., Chattopadhyay, S., Adhikari, S., and Mukherjee, T. (2002) Lipid protective activities of dehydrogingerdiones and probable mode of action. Chem. Biol. Chem. 3, 364-370.
9. (c) Rele, M., Patro, B. S., Adhikari, S., Kalena, G. P., Chattopadhyay, S., and Mukherjee, T. (2002) Proc. Ind. Acad. Sci. 114, 739-747.
10. (a) Ng, T. B., Liu, F., and Wang, Z. T. (2000) Antioxidant activity of natural products from plants. Life Sci. 66, 709-723.
11. (b) Liebgott, T., Miollan, M., Berchadsky, Y., Drieu, K., Culcasi, M., and Pietri, S. (2000) Complementary cardioprotective effects of flavonoid metabolites and terpenoid constituents of ginkgo biloba estract (Egb761) during ischemia and reperfusion. Basic Res. Cardiol. 95, 368-377.
12. Meheta, G., Nayak, U. R., and Sukh, D. (1973) Meroterpenoids-I; Psoralea corylifolia Linn.-1. Bakuchiol, a novel meroterpene phenol. Tetrahedron 29, 1119-1125.
13. (a) Katsura, H., Tsukiyama, R., Suzuki, A., and Kobayashi, M. (2001) In vitro antimicrobial activities of bakuchiol against microorganisms. Antimicrob. Agents Chemother. 45, 3309-3313.
14. (b) Backhouse, C. N., Delporte, C. L., Negrete, R. E., Cassels, B. K., Schneider, C., Breitmaier, E., and San Feliciano, A. (1995) Cyclobakuchiol A and B from Psoralea glandulosa. Phytochemistry 40, 325-327.
15. (c) Haraguchi, H., Inoue, J., Tamura, Y., and Mizutani, K. (2000) Inhibition of mitochondrial lipid peroxidation by bakuchiol, a meroterpene from Psoralea corylifolia. Planta Med. 66, 569-571.
16. Banerji, A., and Chintalwar, G. J. (1985) Role of amino acids in terpenoid biosynthesis. Proc. Third Int. Conf. Chem. Biotechnol. Biologically Active Nat. Prod. 3, 285-299.
17. Joshi, R., Adhikari, S., Patro, B. S., Chattopadhyay, S., and Mukherjee, T. (2001) Free radical scavenging behavior of folic acid: Evidence for possible antioxidant activity. Free Radical Biol. Med. 30, 1390-1399.
18. Mellors, A., and Tappel, A. L. (1966) The inhibition of mitrochondrial peroxidation by ubiquinone and ubiquinol. J. Biol. Chem. 241, 4353-4356.
19. Mukherjee, T. (1997) Atomic, Molecular and Cluster Physics (Ahmad, S. A., Ed.) pp 299-316, Narosa, New Delhi.
20. Buxton, G. V., and Stuart, C. R. (1995) Reevaluation of the thiocyanate dosimeter for pulse radiolysis. J. Chem. Soc., Faraday Trans. 91, 279-281.
21. Schmidt, M. W., Baldridge, K. K., Boatz, J. A., Elbert, S. T., Gordon, M. S., Jensen, J. H., Koseki, S., Matsunaga, N., Nguyen, K. A., Su, S. J., Windus, T. L., Dupuis, M., and Montgomery, J. A. (1993) The general atomic and molecular electronic structure system. J. Comput. Chem. 14, 1347-1363.
22. (a) Ames, B. N., Shigenaga, M. K., and Hagen, T. M. (1993) Oxidants and antioxidants and the degenerative diseases of aging. Proc. Natl. Acad. Sci. U.S.A. 90, 7915-7922.
23. (b) Sies, H. (1997) Antioxidants in Disease: Mechanisms and Therapy, Academic Press, New York.
24. (c) Bonnefont, R. D., Bastard, J. P., Jandon, M. C., and Delattre, J. (2000) Consequences of the diabetic status on the oxidant/antioxidant balance. Diabetes Metab. 26, 163-176.
25. (d) Higashi, Y., Sasaki, S., Nakagawa, K., Matsuura, H., Oshima, T., and Chayama, K. (2002) Endothelial function and oxidative stress in renovascular hypertension. N. Engl. J. Med. 346, 1954-1962.
26. Chevion, S., Roberts, M. A., and Chevion, M. (2000) The use of cyclic voltametry for the evaluation of antioxidant capacity. Free Radical Biol. Med. 28, 860-870.
27. Das, T. N., Dhanasekaran, T., Alfassi, Z. B., and Neta, P. (1998) Reduction potential of the tert-butyl peroxyl radical in aqueous solutions. J. Phys. Chem. A 102, 280-284.
28. Stojanovic, S., Sprinz, H., and Brede, O. (2001) Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Arch. Biochem. Biophys. 391, 79-89.
29. Packer, J. E., Slater, T. F., and Wilson, R. L. (1979) Direct observation of a free radical interaction between vitamin E and C. Nature 278, 737-738.
30. (a) Shen, Y., Lind, J., Eriksen, T. E., and Merenyi, G. (1989) Reactivity of the trichloro methyl peroxyl radical: evidence for a first-order transformation. J. Phys. Chem. 93, 553-557.
31. (b) Guha, S. N., and Priyadarshini, K. I. (2000) Kinetic and redox characteristics of phenoxyl radicals of eugenol and isoeugenol: Apulse radiolysis study. Int. J. Chem. Kinet. 32, 17-23.
32. Erben-Russ, M., Bors, W., and Saran, M. (1987) Reactions of linoleic peroxyl radicals with phenolic antioxidants: A pulse radiolysis study. Int. J. Radiat. Biol. 52, 393-412.
33. (a) von Sonntag, C., and Schuchmann, H. P. (1982) Peroxyl radicals in aqueous solutions. Peroxyl Radicals (Alfassi, Z. B., Ed.) pp 173-234, Wiley, New York.
34. (b) Neta, P., Huie, R. E., Maruthamuthu, P., and Steenken, S. (1989) Solvent effects in the reactions of peroxyl radicals with organic reductants. Evidence for proton-transfer-mediated electron transfer. J. Phys. Chem. 93, 7654-7659.
35. (c) Neta, P., Huie, R. E., and Ross, A. B. (1990) Rate constants for reactions of peroxyl radicals in fluid solutions J. Phys. Chem. Ref. Data 19, 413-513.
36. Stojanovic, S., and Brede, O. (2002) Elementary reactions of the antioxidant action of trans-stilbene derivatives: resveratrol, pinosylvin and 4-hydroxystilbene. Phys. Chem. Chem. Phys. 4, 757-764.
37. (a) Schöneich, C., and Asmus, K.-D. (1990) Reaction of thiyl radicals with alcohols, ethers and polyunsaturated fatty acids: a possible role of thiyl radicals in thiol mutagenesis? Radiat. Environ. Biophys. 29, 263-271.
38. (b) Wardman, P., and von Sonntag, C. (1995) Kinetic factors that control the fate of thiyl radicals in cells. Methods in Enzymology (Packer, L., Ed.) Vol. 251, pp 31-45, Academic Press, New York.
39. (a) Stocker, R., and Frei, B. (1991) Endogeneous antioxidant defences in human blood plasma. Oxidative Stress: Oxidants and Antioxidants (Sies, H., Ed.) pp 213-243, Academic Press, London.
40. (b) Schöneich, C., Dillinger, U., von Bruchhausen, F., and Asmus, K.-D. (1992) Oxidation of polyunsaturated fatty acids and lipids through thiyl and sulfonyl radicals: reaction kinetics and influence of oxygen and structure of thiyl radicals. Arch. Biochem. Biophys. 292, 456-467.
41. (a) Chatgilialoglu, C., Ferreri, C., Ballestri, M., Mulazzani, Q. G., and Landi, L. (2000) Cis/trans isomerization of monounsaturated fatty acid residues in phospholipids by thiyl radicals. J. Am. Chem. Soc. 122, 4593-4601.
42. (b) Sprinz, H., Adhikari, S., and Brede, O. (2001) Transformation of phospholipid membranes by thiyl radicals via cis-trans isomerization of fatty acid residues. Adv. Colloid Interface Sci. 89-90, 313-325.
43. (c) Adhikari, S., Sprinz, H., and Brede, O. (2001) Thiyl radical induced isomerization of unsaturated fatty acids: Determination of equilibrium constants. Res. Chem. Intermed. 27, 549-559.
44. (d) Ferreri, C., Mennella, R. M., Formisano, C., Landi, L., and Chatgilialoglu, C. (2002) Arachidonate geometrical isomers generated by thiyl radicals: The relationship with trans lipids detected in biological samples. Free Radical Biol. Med. 33, 1516-1526.
45. (a) Surdhar, S. P., and Armstrong, D. (1987) Reduction potential and exchange reactions of thiyl radicals and disulfide anion radicals J. Phys. Chem. 91, 6532-6537.
46. .-, mediating electron transfer to Fe(III)-cytochrome c. Biophys. Chem. 49, 101-110.
47. (a) Becke, A. D. (1993) A new mixing of Hatree-Fock and local density-functional theories. J. Chem. Phys. 98, 1372-1377.
48. (b) Becke, A. D. (1993) Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652.
49. (c) Lee, C., Yang, W., and Parr, R. G. (1988) Development of Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789.
50. (d) Kirkwood, J. G. (1934) On the theory of strong electrolyte solutions. J. Chem. Phys. 2, 351-361.
51. (e) Onsagar, L. (1936) Electric moment of molecules in liquids. J. Am. Chem. Soc. 58, 1486-1493.
52. Jovanovic, S. V., Boone, C. W., Steenken, S., Trigona, M., and Kaskey, R. B. (2001) How curcumin works preferentially with water soluble antioxidants. J. Am. Chem. Soc. 123, 3064-3068.