Anacardic acids and ferric ion chelation

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 62, Issue 9-10, 2007, Pages 710-716

  Tsujimoto, Kazuo ^a   Hayashi, Akio ^a   Tae, Joung Ha ^b   Kubo, Isao ^b  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Anacardic acids; Deprotonated molecule; Iron; Lipoxygenase

Indexed keywords

ANACARDIACEAE; ANACARDIUM OCCIDENTALE; GLYCINE MAX;

EID: 36148937568     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2007-9-1014     Document Type: Article

References (47)

1. Arora A., Nair M. G., and Strasburg G. M. (1998), Structure-activity relationships for antioxidant activities of a series of flavonoids an a liposomal system. Free Rad. Biol. Med. 24, 1355-1363.
2. Aruoma O. I. and Halliwell B. (1991), Free Radicals and Food Additives. Taylor & Francis, London.
3. Bhattacharya S. K., Mukhopadhyay M., Rao P. J. R. M., Bagchi A., and Ray, A. B. (1987), Pharmacological investigation on sodium salt and acetyl derivative of anacardic acid. Phytother. Res. 1, 127-131.
4. Clapp C. H., Banerjee A., and Rotenberg S. A. (1985), Inhibition of soybean lipoxygenase-1 by N-alkylhydroxylamines. Biochemistry 24, 1826-1830.
5. Coates N. J., Gilpin M. L., Gwynn M. N., Lewis D. E., Milner P. H., Spear S. R., and Tyler J. W. (1994), SB-202742, a novel β-lactamase inhibitor isolated from Spondias mombin. J. Nat. Prod. 57, 654-657.
6. Copeland R. A. (2000), Enzyme: A Practical Introduction to Structure, Mechanism, and Data Analysis. Wiley-VCH, New York, pp. 266-332.
7. Cornicelli J. A. and Trivedi B. K. (1999), 15-Lipoxygenase and its inhibition: a novel therapeutic target for vascular disease. Curr. Pharm. Design 5, 11-20.
8. Gardner H. W. (1991), Recent investigations into the lipoxygenase pathway of plants. Biochim. Biophys. Acta 1084, 221-239.
9. Gardner H. W. (1995), Biological roles and biochemistry of the lipoxygenase pathway. HortScience 30, 197-205.
10. Gibian M. J. and Galaway R. A. (1976), Steady-state kinetics lipoxygenase oxygenation of unsaturated fatty acid. Biochemistry 15, 4209-4214.
11. Grazzini R., Hesk D., Heininger E., Hildenbrandt G., Reddy C. C., Cox-Foster D., Medford J., Craig R., and Mumma R. O. (1991), Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids. Biochem. Biophy. Res. Commun. 176, 775-780.
12. Grechkin A. (1998), Recent developments in biochemistry of the plant lipoxygenase pathway. Prog. Lipid Res. 37, 317-352.
13. Ha T. J. and Kubo I. (2005), Lipoxygenase inhibitory activity of anacardic acids. J. Agric. Food Chem. 53, 4350-4354.
14. Ha T. J. and Kubo I. (2007), Slow-binding inhibition of soybean lipoxygenase-1 by dodecyl gallate. J. Agric. Food Chem. 55, 446-451.
15. Ha T. J., Nihei K. and Kubo I. (2004), Lipoxygenase inhibitory activity of octyl gallate. J. Agric. Food Chem. 52, 3177-3181.
16. Halliwell B. and Gutteridge J. M. C. (1989), Free Radicals in Biology and Medicine, 2nd ed. Clarendon Press, Oxford.
17. Hasinoff B. B. and Davey J. P. (1989), The inhibition of a membrane-bound enzyme as a model for anaesthetic action and drug toxicity. Biochem. J. 258, 101-107.
18. 2+-adducts. J. Mass. Spectrom. Soc. Jpn. 55, 7-13.
19. Henle E. S. and Linn S. (1997), Formation, prevention, and repair of DNA damage by iron/hydrogen peroxide. J. Biol. Chem. 272, 19095-19098.
20. Hird N. W. and Milner P. H. (1994), Synthesis and β-lactamase inhibition of anacardic acids and their analogs. Bioorg. Med. Chem. Lett. 4, 1423-1428.
21. Irie J., Murata M., and Homma S. (1996), Glycerol-3-phosphate dehydrogenase inhibitors, anacardic acids, from Ginkgo biloba. Biosci. Biotechnol. Biochem. 60, 240-243.
22. Kemal C., Louis-Flamberg P., Krupinski-Olsen R., and Shorter A. (1987), Reductive inactivation of soybean lipoxygenase-1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry 26, 7064-7072.
23. Kris-Etherton P. M. and Keen C. L. (2002), Evidence that the antioxidant flavonoids in tea and cocoa are beneficial for cardiovascular health. Curr. Opin. Lipidol. 13, 41-49.
24. Kubo I., Komatsu S., and Ochi M. (1986), Molluscicides from the cashew Anacardium occidentale and their large-scale isolation. J. Agric. Food Chem. 34, 970-973.
25. Kubo I., Kim M., Naya K., Komatsu S., Yamagiwa Y., Ohashi K., Sakamoto Y., Hirakawa S., and Kamikawa T. (1987), Prostaglandin synthetase inhibitors from the African medicinal plant Ozoroa mucronata. Chem. Lett. 6, 1101-1104.
26. Kubo I., Muroi H., Himejima M., Yamagiwa Y., Mera Y., Tokushima K., Ohta S., and Kamikawa T. (1993), Structure and antimicrobial activity relationships of anacardic acids. J. Agric. Food Chem. 41, 1016-1019.
27. Kubo I., Kinst-Hori I., and Yokokawa Y. (1994), Tyrosinase inhibitors from Anacardium occidentale fruits. J. Nat. Prod. 57, 545-551.
28. Kubo J., Lee J. R., and Kubo I. (1999), Anti-Helicobacter pylori agents from the cashew apple. J. Agric. Food Chem. 47, 533-537.
29. Kubo I., Kinst-Hori I., Chaudhuri S. K., Kubo Y., Sanchez Y., and Ogura T. (2000), Flavonols from Heterotheca inuloides: tyrosinase inhibitory activity and structural criteria. Bioorg. Med. Chem. 8, 1749-1755.
30. Kubo I., Masuoka N., Ha T. J., and Tsujimoto K. (2006), Antioxidant activity of anacardic acids. Food Chem. 99, 555-562.
31. Lodovici M., Guglielmi F., Meoni M., and Dolara P. (2001), Effect of natural phenolic acids on DNA oxidation in vitro. Food Chem. Toxicol. 39, 1205-1210.
32. Mansuy D., Cucurou C., Biatry B., and Battioni J. P. (1988), Soybean lipoxygenase-catalyzed oxidations by linoleic acid hydroperoxide: different reducing substrates and dehydrogenation of phenidone and BW 755C. Biochem. Biophys. Res. Commun. 151, 339-346.
33. Masuoka N. and Kubo I. (2004), Characterization of xanthine oxidase inhibition by anacardic acids. Biochim. Biophys. Acta 1688, 245-249.
34. Nagabhushana K. S., Shobha S. V., and Ravindranath B. (1995), Selective ionophoric properties of anacardic acid. J. Nat. Prod. 58, 807-810.
35. Nelson M. J. (1988), Catecholate complex of ferric soybean lipoxygenase-1. Biochemistry 27, 4273-4278.
36. Nomura M. and Fujihara Y. (1994), Inhibition of 6-[(8Z,11Z) ,14-pentadecatrienyl]salicylic acid derivatives. J. Jpn. Oil Chem. Soc. 43, 574-578.
37. Prigge S. T., Boyington J. C., Faig M., Doctor K. S., Gaffney B. J., and Amzel L. M. (1997), Structure and mechanism of lipoxygenases. Biochimie 79, 629-636.
38. Richard-Forget F., Gauillard F., Hugues M., Jean-Marc T., Boivin P., and Nicolas J. (1995), Inhibition of horse bean and germinated barley lipoxygenases by some phenolic compounds. J. Food Sci. 60, 1325-1329.
39. Rickert K. W. and Klinman J. P. (1999), Nature of hydrogen transfer in soybean lipoxygenase-1: separation of primary and secondary isotope effects. Biochemistry 38, 12218-12228.
40. Ruddat V. C., Whitman S., Holman T. R., and Bernasconi C. F. (2003), Stopped-flow kinetics investigations of the activation of soybean lipoxygenase-1 and the influence of inhibitors on the allosteric site. Biochemistry 42, 4172-4178.
41. Sánchez-Ferrer A., Rodríguez-López J. N., García-Cánovas F., and García-Carmona F. (1995), Tyrosinase: A comprehensive review of its mechanism. Biochim. Biophys. Acta 1247, 1-11.
42. Shobha S. V., Ramadoss C. S., and Ravindranath B. (1994), Inhibition of soybean lipoxygenase-1 by anacardic acids, cardols, and cardanols. J. Nat. Prod. 57, 1755-1757.
43. Tanford C. (1980), The Hydrophobic Effect: Formation of Micelles and Biological Membranes, 2nd ed. John Wiley & Sons, New York.
44. Toyomizu M., Sugiyama S., Jin R. L., and Nakatsu T. (1993), α-Glucosidase and aldose reductase inhibitors: constituents of cashew, Anacardium occidentale, nut shell liquids. Phytother. Res. 7, 252-254.
45. Trevisan M. T. S., Pfundstein B., Haubner R., Würtele G., Spiegelhaider B., Bartsch H., and Owen R. W. (2006), Characterization of alkyl phenols in cashew (Anacardium occidentale) products and assay of their antioxidant capacity. Food Chem. Toxicol. 44, 188-197.
46. Tyman J. H. P. (1979), Non-isoprenoid long chain phenols. Chem. Soc. Rev. 8, 499-537.
47. Yamagiwa Y., Ohashi K., Sakamoto Y., Hirakawa S., Kamikawa T., and Kubo I. (1987), Syntheses of anacardic acids and ginkgoic acid. Tetrahedron 43, 3387-3394.