In vitro antioxidant properties, DNA damage protective activity, and xanthine oxidase inhibitory effect of cajaninstilbene acid, a stilbene compound derived from pigeon pea [ Cajanus cajan (L.) Millsp.] leaves

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 1, 2011, Pages 437-443

  Wu, Nan ^a   Kong, Yu ^a   Fu, Yujie ^a   Zu, Yuangang ^a   Yang, Zhiwei ^a   Yang, Mei ^a   Peng, Xiao ^a   Efferth, Thomas ^a,b  

^a NORTHEAST FORESTRY UNIVERSITY   (China)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

antioxidant activity; Cajaninstilbene acid; DNA damage; stilbene; xanthine oxidase

Indexed keywords

ANTIOXIDANT ACTIVITIES; CAJANINSTILBENE ACID; DNA DAMAGE; STILBENE; XANTHINE OXIDASE;

BINDING ENERGY; DNA; NITRIC OXIDE; OXYGEN;

NUCLEIC ACIDS;

3 HYDROXY 4 PRENYL 5 METHOXYSTILBENE 2 CARBOXYLIC ACID; 3-HYDROXY-4-PRENYL-5-METHOXYSTILBENE-2-CARBOXYLIC ACID; ANTIMUTAGENIC AGENT; ANTIOXIDANT; BACTERIAL DNA; ENZYME INHIBITOR; PLANT EXTRACT; SALICYLIC ACID DERIVATIVE; STILBENE DERIVATIVE; XANTHINE OXIDASE;

ARTICLE; CHEMISTRY; DNA DAMAGE; DRUG ANTAGONISM; GENETICS; HUMAN; PIGEONPEA; PLANT LEAF;

ANTIMUTAGENIC AGENTS; ANTIOXIDANTS; CAJANUS; DNA DAMAGE; DNA, BACTERIAL; ENZYME INHIBITORS; HUMANS; PLANT EXTRACTS; PLANT LEAVES; SALICYLIC ACIDS; STILBENES; XANTHINE OXIDASE;

CAJANUS CAJAN;

EID: 78651098731     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf103970b     Document Type: Article

References (38)

1. Simonian, N. A.; Coyle, J. T. Oxidative stress in neurodegenerative diseases Annu. Rev. Pharmacol. Toxicol. 1996, 36, 83-106
2. Halliwell, B.; Gutteridge, J. M. C. Role of free radicals and catalytic metal ions in human disease: an overview Methods Enzymol. 1990, 186, 1-85
3. Hatano, T.; Edamatsu, R.; Hiramatsu, M.; Mori, A.; Fujita, Y.; Yoshida, T.; Okuda, T. Effects of interaction of tannins with co-existing substances. VI: Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical Chem. Pharm. Bull. 1989, 37, 2016-2021
4. Wiseman, H.; Halliwell, B. Damage to DNA by reactive oxygen and nitrogen species: role of inflammatory disease and progression to cancer Biochem. J. 1996, 313, 17-29
5. Stich, H. F. The beneficial and hazardous effects of simple phenolic compounds Mutat. Res. 1991, 259, 307-324
6. Hille, R.; Nishino, T. Flavoprotein structure and mechanism. Xanthine oxidase and xanthine dehydrogenase FASEB J. 1995, 9, 995-1003
7. Enroth, C.; Eger, B. T.; Okamoto, K.; Nishino, T.; Pai, E. F. Crystal structures of bovine milk xanthine dehydrogenase and xanthine oxidase: structure-based mechanism of conversion Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10723-10728
8. Ardan, T.; Kovaceva, J.; Cejkova, J. Comparative histochemical and immunohistochemical study on xanthine oxidoreductase/xanthine oxidase in mammalian corneal epithelium Acta Histochem. 2004, 106, 69-75
9. Lin, C. M.; Chen, C. S.; Chen, C. T.; Liang, Y. C.; Lin, J. K. Molecular modeling of flavonoids that inhibits xanthine oxidase Biochem. Biophys. Res. Commun. 2002, 294, 167-172
10. Ali, H. I.; Fujita, T.; Akaho, E.; Nagamatsu, T. A comparative study of AutoDock and PMF scoring performances, and SAR of 2-substituted pyrazolotriazolopyrimidines and 4-substituted pyrazolopyrimidines as potent xanthine oxidase inhibitors J. Comput.-Aided Mol. Des. 2010, 24, 57-75
11. Grover, J. K.; Yadav, S.; Vats, V. J. Medicinal plants of India with anti-diabetic potential J. Ethnopharmacol. 2002, 81, 81-100
12. Tang, Y.; Wang, B.; Zhou, X. J. Effect of external application of herbal cajani preparation on the fibronection content during healing process of open wound J. Guangzhou Univ. Tradit. Chin. Med. 1999, 16, 302-304
13. Luo, Q. F.; Sun, L.; Si, J. Y.; Chen, D. H. Hypocholesterolemic effect of stilbenes containing extract-fraction from Cajanus cajan L. on diet-induced hypercholesterolemia in mice Phytomedicine 2008, 15, 932-939
14. Hain, R.; Bieseler, B.; Kindl, H.; Schroder, G.; Stocker, R. Expression of a stilbene synthase gene in Nicotiana tabacum results in synthesis of the phytoalexin resveratrol Plant Mol. Biol. 1990, 15, 325-335
15. Savio, M.; Coppa, T.; Bianchi, L.; Vannini, V.; Maga, G.; Forti, L.; Cazzalini, O.; Lazzè, M. C.; Perucca, P.; Prosperib, E.; Stivala, L. A. The resveratrol analogue 4,4′-dihydroxy-trans-stilbene inhibits cell proliferation with higher efficiency but different mechanism from resveratrol Int. J. Biochem. Cell Biol. 2009, 41, 2493-2502
16. Wu, N.; Fu, K.; Fu, Y. J.; Zu, Y. G.; Chang, F. R.; Chen, Y. H.; Liu, X. L.; Kong, Y.; Liu, W.; Gu, C. B. Antioxidant activities of extracts and main components of pigeonpea [ Cajanus cajan (L.) Millsp.] leaves Molecules 2009, 14, 1032-1043
17. Kong, Y.; Fu, Y. J.; Zu, Y. G.; Chang, F. R.; Chen, Y. H.; Liu, X. L.; Stelten, J.; Schiebel, H. M. Cajanuslactone, a new coumarin with anti-bacterial activity from pigeon pea [ Cajanus cajan (L.) Millsp.] leaves Food Chem. 2010, 121, 1150-1155
18. Wang, Z. H.; Hsu, C. C.; Yin, M. C. Antioxidative characteristics of aqueous and ethanol extracts of glossy privet fruit Food Chem. 2009, 112, 914-918
19. Halliwell, B.; Gutteridge, J. M. C.; Aruoma, O. I. The deoxyribose method: a simple test tube assay for determination of rate constants for reaction of hydroxyl radicals Anal. Biochem. 1987, 165, 215-219
20. Sharma, M.; Tripathi, P.; Singh, V. P.; Tripathi, Y. B. Hepatoprotective and toxicological evaluation of hepatomed, an ayurvedic drug Indian J. Exp. Biol. 1995, 33, 34-37
21. Accelrys Inc. InsightII, Version (2005; Accelrys Inc., San Diego, CA.
22. Pauff, J. M.; Zhang, J.; Bell, C. E.; Hille, R. Substrate orientation in xanthine oxidase: crystal structure of enzyme in reaction with 2-hydroxy-6-methylpurine J. Biol. Chem. 2008, 283, 4818-4824
23. Yang, Z. W.; Yang, G.; Zu, Y. G.; Fu, Y. J.; Zhou, L. J. The conformational analysis and proton transfer of the neuraminidase inhibitors: a theoretical study Phys. Chem. Chem. Phys. 2009, 11, 10035-10041
24. Accelrys Inc. Affinity User Guide; Accelrys Inc.: San Diego, CA, 2005.
25. Lee, J. C.; Kim, H. R.; Kim, J.; Jang, Y. S. J. Antioxidant property of an ethanol extract of the stem of Opuntia ficus-indica Var. Saboten J. Agric. Food Chem. 2002, 50, 6490-6496
26. Head, J. D.; Zerner, M. C. A Broyden-Fletcher-Goldfarb-Shanno optimization procedure for molecular geometries Chem. Phys. lett. 1985, 122, 264-270
27. Kamilo-lu, Ö.; Ercisli, S.; engül, M.; Toplu, C.; Serie, S. Total phenolics and antioxidant activity of jujube (Zizyphus jujube Mill.) genotypes selected from Turkey Afr. J. Biotechnol. 2009, 8, 303-307
28. Kaur, C.; Kapoor, H. C. Anti-oxidant activity and total phenolic content of some Asian vegetables Int. J. Food Sci. Technol. 2002, 37, 153-161 (Pubitemid 36840533)
29. Gavino, V. C.; Miller, J. S.; Ikareblha, S. O.; Milo, G. E.; Cornwell, D. G. Effects of polyunsaturated fatty acids and antioxidants on lipid peroxidation in tissue cultures J. Lipid Res. 1981, 22, 763-769
30. 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
31. Sabuncuoglu, S.; Sohretoglu, D.; Koray Sakar, M.; Ozgunes, H. Antioxidant activity of polyphenolic compounds and extracts from Geranium purpureum Toxicol. Lett. 2008, 180S, S32-S246
32. Hasiah, A. H.; Ghazali, A. R.; Weber, J. E. F.; Velu, S.; Thomas, N. F.; Inayat Hussain, S. H. Cytotoxic and antioxidant effects of methoxylated stilbene analogues on HepG2 hepatoma and Chang liver cells: implications for structure activity relationship. Hum. Exp. Toxicol. 2010, (doi: 10.1177/0960327110368739).
33. Wilson, M. A.; Rimando, A. M.; Wolkow, C. A. Methoxylation enhances stilbene bioactivity in Caenorhabditis elegans BMC Pharmacol. 2008, 8, 15-26
34. Mérillon, J. M.; Fauconneau, B.; Teguo, P. W.; Barrier, L.; Vercauteren, J.; Huguet, F. Antioxidant activity of the stilbene astringin, newly extracted from Vitis vinifera cell cultures Clin. Chem. 1997, 43, 1092-1093
35. Matsuda, H.; Morikawa, T.; Toguchida, I.; Park, J. Y.; Harima, S.; Yoshikawa, M. Antioxidant constituents from rhubarb: structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides Bioorg. Med. Chem. 2001, 9, 41-50
36. Kaur, R.; Arora, S.; Singh, B. Antioxidant activity of the phenol rich fractions of leaves of Chukrasia tabularis A. Juss Bioresour. Technol. 2008, 99, 7692-7698
37. Hatano, T.; Edamatsu, R.; Hiramatsu, M.; Mori, A.; Fujita, Y.; Yoshida, T.; Okuda, T. Effects of interaction of tannins with co-existing substances. VI: Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical Chem. Pharm. Bull. 1989, 37, 2016-2021
38. Chang, W. S.; Lee, Y. J.; Lu, F. J.; Chiang, H. C. Inhibitory effects of flavonoids on xanthine oxidase Anticancer Res. 1993, 13, 2165-2170