Sclerotiorin, a novel inhibitor of lipoxygenase from Penicillium frequentans

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 8, 2007, Pages 2879-2883

  Chidananda, C ^a   Sattur, A P ^a  

^a CENTRAL FOOD TECHNOLOGICAL RESEARCH INSTITUTE   (India)

Author keywords

Antioxidant; Inhibitor; Lipoxygenase; Penicillium frequentans; Sclerotiorin

Indexed keywords

ANTIOXIDANT; BENZOPYRAN DERIVATIVE; FREE RADICAL; LIPOXYGENASE; LIPOXYGENASE INHIBITOR; LIPOXYGENASE L 1; LIPOXYGENASE L-1; SCLEROTIORIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG EFFECT; ISOLATION AND PURIFICATION; PENICILLIUM;

ANTIOXIDANTS; BENZOPYRANS; FREE RADICALS; LIPOXYGENASE; LIPOXYGENASE INHIBITORS; PENICILLIUM;

GLYCINE MAX; PENICILLIUM; PENICILLIUM GLABRUM;

EID: 34247595326     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf062032x     Document Type: Article

References (34)

1. Barsh, A. R. Lipoxygenase: Occurrence, function, catalysis and acquisition of substrate. J. Biol. Chem. 1999, 274, 23679-23682.
2. Grechkin, A. Recent developments in biochemistry of plant lipoxygenase pathway. Prog. Lipid Res. 1998, 37, 317-352.
3. Steinberg, D. At last, direct evidence that lipoxygenase a role in atherogenesis. J. Clin. invest. 1999, 103, 1487-1488.
4. Prigge, S. T.; Boyington, J. C.; Faig, M.; Doctor, K. S.; Gaffney, B. J.; Amzel, L. M. Structure and mechanism of lipoxygenases. Biochimie 1997, 79, 629-636.
5. Rao, K. C. S.; Divakar, S.; Babu, K. N.; Karanth, N. G.; Sattur, A. P. Nigerloxin, a novel inhibitor of aldose reductase and lipoxygenase with free radical scavenging activity from Aspergillus niger CFR-W-105. 7. Antibiot. 2002, 55, 789-793.
6. Rao, K. C. S.; Divakar, S.; Rao, A. G. A.; Karanth, N. G.; Suneetha, W. J.; Krishnakanth, T. P.; Sattur, A. P. Asperenone an inhibitor of 15-lipoxygenase and human platelet aggregation from Aspergillus niger. Biotechnol. Lett. 2002, 24, 1967-1970.
7. Chidananda, C.; Rao, L. J. M.; Sattur, A. P. Sclerotiorin, from Penicillium frequentans, a potent inhibitor of aldose reductase. Biotechnol. Lett. 2006, 28, 1633-1636.
8. 5Cl, a chlorine-containing metabolic product of Penicillium sclerotiorum van BEYMA. Biochem. J. 1940, 34, 1419-1421.
9. Whalley, W. B.; Ferguson, G.; Marsh, W. C.; Restivo, R. J. The chemistry of fungi, part LXVIII. The absolute configuration of (+)-sclerotiorin and of the azaphilones. J. Chem. Soc. Perkin. Trans. I 1976, 1366-1369.
10. Tabata, Y.; Ikegami, S.; Yaguchi, T.; Sasaki, T.; Hashiko, S.; Sakma, S.; Shia-Ya, K.; Seto, H. Diazaphilonic acid, a new azaphilone with telomerase inhibitory activity. J. Antibiot. 1999, 52, 412-414.
11. Kono, K.; Tanaka, M.; Ono, Y.; Hosoya, T.; Ogita, T.; Kahama, T. S-15183 a & b, new sphingosine kinase inhibitors, produced from fungi. J. Antibiot. 2001, 54, 415-420.
12. Nam, J. Y.; Son, K. H.; Kim, H. K.; Han, M. Y.; Kim, S. U.; Choi, J. D.; Kwon, B. M. Sclerotiorin and isochromophilone IV: Inhibitors of Grb2-Shc interaction, isolated from Penicillium multicolor F1753.7. Microbiol. Biotechnol. 2000, 10, 544-546.
13. 2 inhibitors containing sclerotiorin from Penicillium sclerotiorum for treatment of inflammatory pancreatitis, and allergy. Jpn. Kokai Tokyo Koho 1990, JP 02255615A2.
14. Negishi, Y.; Matsuo, N.; Miyadera, K.; Tanishima, M. Lipase inhibitors containing sclerotiorin. Jpn. Kokai Tokyo Koho 2000, JP 200091527 A2.
15. Takenaka, Y.; Tanahashi, T.; Nagakura, N.; Hamada, N. Production of xanthones with free radical scavenging property, emodin and sclerotiorin by cultured lichen mycobionts of Pyrenula japonica. Z. Naturforsch. 2000, 55, 910-14.
16. Axelrod, B.; Cheesbrough, T. M.; Laakso, S. Lipoxygenase from soybeans. Methods Enzymol. 1981, 71, 1321-1324.
17. Prieto, P.; Pineda, M.; Aquilar, M. Spectrophotometric quantification of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to determination of Vitamin E. Anal. Biochem. 1999, 269, 337-341.
18. Abe, N.; Nemoto, A.; Tsuchiya, Y.; Hojo, H.; Hirota, A. Studies, on the 1,1-diphenyl 1-2-picrylhydrazyl radical scavenging mechanism for 2-pyrone compounds. Biosci., Biotechnol., Biochem. 2000, 64, 306-313.
19. Buege, J. A.; Aust, S. D. Microsomal lipid peroxidation. Methods Enzymol. 1978, 52, 302-310.
20. Carter, P. Spectrophotometric determination of serum Iron at the submicrogram level with a new reagent (Ferrozine). Anal. Biochem. 1971, 40, 450-458.
21. Hiroshi, T.; Matsushima, C.; Tabata, N.; Namatame, I.; Tanaka, H.; Bamberger, M. J.; Arai, H.; Fukazawa, M.; Inone, K.; Omura, S. Structure-specific inhibition of cholesteryl ester transfer protein by azaphillone. J. Antibiot. 1999, 52, 160-170.
22. Fujimoto, H.; Matsudo, T.; Yamaguchi, A.; Yamazaki, M. Two new fungal azaphilones from Talaraomyces luteus, with monoamine oxidase inhibitory effect. Heterocycles 1990, 30, 607-616.
23. Omura, S.; Tanaka, H.; Ikeda, H. M. Isochromophilones I and II, novel inhibitors against gp120-CD4 binding from Penicillium sp. J. Antibiot. 1993, 46, 1908-1911.
24. Arai, N.; Shiomi, K.; Tomoda, H.; Tabata, N.; Yang, D. J.; Masuma, R.; Kawakuba, T.; Omura, S. Isochromophilones III-IV, inhibitors of acyl-CoA: cholesterol acyltrasferase produced by Penicillium multicolor FO-3216. 7. Antibiot. 1995, 48, 696-702.
25. Pairet, L.; Wrigley, S. K.; Chetland, I.; Reynolds, E. E.; Hayes, M. A.; Holloway, J.; Ainsworth, A. M.; Katzer, W.; Cheng, X. M.; Hupe, D. J.; Charlton, P.; Doherty, A. M. Azaphilones with endothelin receptor binding activity produced by Penicillium sclerotiorum: Taxonomy, fermentation, isolation, structural elucidation and biological activity. J. Antibiot. 1995, 48, 913-923.
26. Yasumoto, B. K.; Yamamoto, A.; Mitsuda, H. Effect of phenolic antioxidants on lipoxygenase reaction. Agric. Biol. Chem. 1970, 34, 1162-1168.
27. Blots, M. S. Antioxidant determination by the use of stable free radical. Nature 1958, 181, 1999-2000.
28. Summerfield, F. W.; Tappel, A. L. Determination of fluorescence quenching of DNA cross-links made by malondialdehyde. Biochim. Biophys. Acta 1983, 185.
29. Horton, A, A.; Fairhurst, S. Lipid peroxidation and mechanism of toxicity. Crit. Rev. Toxicol. 1987, 27-29.
30. Skrzypczak-Jankun, E.; Mc-Cabe, N. P. S. H.; Selman, S. H. J.; Jankun, H. Curcumin inhibits lipoxygenase by binding to its central cavity: Theoretical and X-ray evidence. Int. J. Mol. Med. 2000, 6, 521-526.
31. Guindon, Y.; Girard, Y. A.; Maycock, A.; Ford-Hutchinson, A. W.; Atkinson, J. G. L-651, 392: A novel, potent and selective 5-lipoxygenase inhibitor. Adv. Prostaglandin Thromboxane Leukotrienes Res. 1987, 17, 554-557.
32. Van-der-Zee, J.; Eling, T. E.; Mason, R. P. Formation of free radical metabolites in the reaction between soybean lipoxygenase and its inhibitors. An ESR study. Biochemistry 1989, 28, 8363-8367.
33. Pinto, M. C.; Garcia-Barrado, J. A.; Macias, P. Resveratrol is a potent inhibitor of dioxygenase activity of lipoxygenase. J. Agric. Food. Chem. 1999, 47, 4842-4846.
34. Began, E.; Rao, A. G. Inhibition of lipoxygenase 1 by phosphatidylcholine micelles-bound curcumin. Lipids 33, 1223-1228.