Secondary metabolites from the fungus Monascus kaoliang and inhibition of nitric oxide production in lipopolysaccharide-activated macrophages

Phytochemistry Letters

Volumn 5, Issue 2, 2012, Pages 262-266

  Cheng, Ming Jen ^a   Wu, Ming Der ^a   Su, Yung Shun ^b   Yuan, Gwo Fang ^a   Chen, Yen Lin ^a   Chen, Ih Sheng ^c  

^a FOOD INDUSTRY RESEARCH AND DEVELOPMENT INSTITUTE   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^c KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Azaphilone derivatives; Metabolites; Monascus kaoliang; NO production; Red yeast rice

Indexed keywords

ACETIC ACID DERIVATIVE; GAMMA LACTONE DERIVATIVE; ISOCHROMAN DERIVATIVE; LIPOPOLYSACCHARIDE; MONASCUSKAOLIN; NATURAL PRODUCT; NITRIC OXIDE; QUERCETIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG SCREENING; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; IN VITRO STUDY; MACROPHAGE ACTIVATION; METABOLITE; MINIMUM INHIBITORY CONCENTRATION; MONASCUS KAOLIANG; MOUSE; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PHYTOCHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

FUNGI; MONASCUS KAOLIANG;

EID: 84862807885     PISSN: 18743900     EISSN: 18767486     Source Type: Journal    
DOI: 10.1016/j.phytol.2012.01.008     Document Type: Article

References (32)

1. T. Akihisa, S. Mafune, M. Ukiya, Y. Kimura, K. Yasukawa, T. Suzuki, H. Tokuda, N. Tanabe, and T. Fukuoka (+)- and (-)-syn-2-Isobutyl-4-methylazetidine- 2,4-dicarboxylic acids from the extract of Monascus pilosus-fermented rice (red-mold rice) J. Nat. Prod. 67 2004 479 480
2. T. Akihisa, H. Tokuda, K. Yasukawa, M. Ukiya, A. Kiyota, N. Sakamoto, T. Suzuki, N. Tanabe, and H. Nishino Azaphilones, furanoisophthalides, and amino acids from the extracts of Monascus pilosus-fermented rice (red-mold rice) and their chemopreventive effects J. Agric. Food Chem. 53 2005 562 565
3. 2A Adenosine receptor antagonists: a study on the importance of modifications at the side chain on the activity and solubility J. Med. Chem. 45 2002 115 126
4. P.J. Blanc, M.O. Loret, A.L. Santerre, A. Pareilleux, D. Prome, J.C. Prome, J.P. Laussac, and G. Goma Pigments of Monascus J. Food Sci. 59 1994 862 865
5. M.J. Cheng, M.D. Wu, I.S. Chen, and G.F. Yuan Secondary metabolites from the mycelia of the fungus Monascus pilosus BCRC 38072 Chem. Pharm. Bull. 56 2008 394 397
6. M.J. Cheng, M.D. Wu, P.S. Yang, J.J. Chen, Y.L. Chen, and G.F. Yuan Secondary metabolites isolated from the fungus Monascus kaoliang-fermented rice J. Chil. Chem. Soc. 55 2010 107 110
7. A. Endo Monacolin K, a new hypocholesterolemic agent produced by a Monascus species J. Antibiot. 32 1979 852 854
8. A. Endo Compactin (ML-236B) and related compounds as potential cholesterol-lowering agents that inhibit HMG-CoA reductase J. Med. Chem. 28 1985 401 405
9. T.W. Hearn Carbon-13 chemical shifts in some substituted furans and thiophenes Aust. J. Chem. 29 1996 107 113
10. C.F. Hossain, E. Okuyama, and M. Yamazaki A new series of coumarin derivatives having monoamine oxidase inhibitory activity from Monascus anka Chem. Pharm. Bull. 44 1996 1535 1539
11. Y.W. Hsu, L.C. Hsu, Y.H. Liang, Y.H. Kuo, and T.M. Pan Monaphilones A-C, three new antiproliferative azaphilone derivatives from Monascus purpureus NTU 568 J. Agric. Food Chem. 58 2010 8211 8216
12. Z. Huang, Y. Xu, L. Li, and Y. Li Two new Monascus metabolites with strong blue fluorescence isolated from red yeast rice J. Agric. Food Chem. 56 2008 112 118
13. M. Johansson, B. Köpcke, H. Anke, and O. Sterner Biologically active secondary metabolites from the ascomycete A111-95. 2. Structure elucidation J. Antibiot. 55 2002 104 106
14. S. Jongrungruangchok, P. Kittakoop, B. Yongsmith, R. Bavovada, S. Tanasupawat, N. Lartpornmatulee, and Y. Thebtaranonth Azaphilone pigments from a yellow mutant of the fungus Monascus kaoliang Phytochemistry 65 2004 2569 2575
15. P. Jůzlová, L. Martinková, and V. Kren Secondary metabolites of the fungus Monascus: a review J. Ind. Microbiol. 16 1996 163 170
16. A. Knecht, B. Cramer, and H.U. Humpf New Monascus metabolites: structure elucidation and toxicological properties studied with immortalized human kidney epithelial cells Mol. Nutr. Food Res. 50 2006 314 321
17. R.T. Lalonde, C. Wong, and A.I.M. Tsai Polyglucoside metabolites of deaceae the chain sesquence of oleoside aglucon, tyrosol and glucose unite in three metabolites from Fraxinus Americana J. Am. Chem. Soc. 98 1976 3007 3012
18. W.S. Lee, M.J. Kim, Y.I. Beck, Y.D. Park, and T.S. Jeong Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots Bioorg. Med. Chem. Lett. 15 2005 3573 3575
19. J. Ma, Y. Li, Q. Ye, J. Li, Y. Hua, D. Ju, D. Zhang, R. Cooper, and M. Chang Constituents of red yeast rice, a traditional Chinese food and medicine J. Agric. Food Chem. 48 2000 5220 5225
20. L. Martinokova, P. Juzlova, and D. Vesely Biological activity of polyketide pigments produced by the fungus Monascus J. Appl. Bacteriol. 79 1995 609 616
21. T. Mosman Utilization of purified human monocytes in the agarose droplet assay for measuring migration inhibitory factors J. Immunol. Methods 65 1983 55 63
22. R.E. Mudgett Monascus G.J. Lauro, F.J. Francis, Natural Food Colorants Science and Technology 2000 Marcel Dekker New York 31 85
23. H. Nozaki, S. Date, H. Kondo, H. Kiyohara, D. Takaoda, T. Tada, and M. Nakayama Ankalactone, a new α,β-unsaturated γ-lactone form Monascus anka Agric. Biol. Chem. 55 1991 899 990
24. S. Sakai, K. Minoda, G. Saito, and A. Sato Therapeutic efficiency of p-hydroxybenzoic acid ester J. Sci. Res. Inst. (Tokyo) 50 1956 93 97
25. K. Sato, Y. Goda, S.S. Sakamoto, H. Shibata, T. Maitani, and T. Yamada Identification of major pigments containing d-amino acid units in commercial Monascus pigments Chem. Pharm. Bull. 45 1997 227 229
26. Y.H. Tseng, J.H. Yang, H.L. Chang, Y.L. Lee, and J.L. Mau Antioxidant properties of methanolic extracts from monascal adlay Food Chem. 97 2006 375 381
27. K. Tsuji, T. Ichikawa, N. Tanabe, S. Abe, S. Tarui, and Y. Nakagawa Effects of two kinds of Kojion blood pressure in spontaneously hypertensive rats Nippon. Nogeikagaku Kaishi. 66 1992 1241 1246
28. E. Wenkert, M.E. Alonso, H.E. Gottlieb, E. Sanchez, R. Pellicciari, and P. Cogolli Reactions of ethyl diazoacetate with thianaphthene, indoles, and benzofuran J. Org. Chem. 42 1977 3945 3949
29. D. Wild, G. Tóth, and H.U. Humpf New Monascus metabolite isolated from red yeast rice (Angkak, red Koji) J. Agric. Food Chem. 50 2002 3999 4002
30. D. Wild, G. Tóth, and H.U. Humpf New Monascus metabolites with a pyridine structure in red fermented rice J. Agric. Food Chem. 51 2003 5493 5496
31. H.C. Wong, and Y.S. Bau Pigmentation and antibiobacterial activity of fast neutron- and X-ray induced strains of Monascus purpureus went Plant Physiol. 60 1977 578 581
32. C.Z. Zhang, X.Z. Xu, and C. Li Fructosides from Cynomorium songaricum Phytochemistry 41 1996 975 976