Monaphilones A-C, three new antiproliferative azaphilone derivatives from Monascus purpureus NTU 568

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 14, 2010, Pages 8211-8216

  Hsu, Ya Wen ^a,b   Hsu, Li Chuan ^a,b   Liang, Yu Han ^a,b   Kuo, Yao Haur ^b,c   Pan, Tzu Ming ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

^c CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

ankaflavin; azaphilone; HPLC; Monaphilones A C; monascin; Monascus purpureus

Indexed keywords

AZAPHILONE; BENZOPYRAN DERIVATIVE; CYCLOHEXANONE DERIVATIVE; GROWTH INHIBITOR; MONAPHILONE A; MONAPHILONE B; MONAPHILONE C; PIGMENT;

ARTICLE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HUMAN; ISOLATION AND PURIFICATION; MONASCUS; TUMOR CELL LINE; DRUG EFFECTS;

BENZOPYRANS; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLOHEXANONES; GROWTH INHIBITORS; HUMANS; MONASCUS; PIGMENTS, BIOLOGICAL;

MONASCUS; MONASCUS PURPUREUS;

EID: 77954867227     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf100930j     Document Type: Article

References (19)

1. Endo, A. Monacolin K, a new hypocholesterolemic agent produced by a Monascus species J. Antibiot. 1979, 32, 852-854
2. Endo, A.; Komagata, D.; Shimada, H. Monacolin M, a new inhibitor of cholesterol biosynthesis J. Antibiot. 1986, 39, 1670-1673
3. Akihisa, T.; Tokuda, H.; Yasukawa, K.; Ukiya, M.; Kiyota, A.; Sakamoto, N.; Suzuki, T.; Tanabe, N.; Nishino, H. Azaphilones, furanoisophthalides, and amino acids from the extracts of Monascus pilosus -fermented rice (red-mold rice) and their chemopreventive effects J. Agric. Food Chem. 2005, 53, 562-565
4. Su, N. W.; Lin, Y. L.; Lee, M. H.; Ho, C. Y. Ankaflavin from Monascus -fermented red rice exhibits selective cytotoxic effect and induces cell death on Hep G2 cells J. Agric. Food Chem. 2005, 53, 1949-1954
5. Aniya, Y.; Yokomakura., T.; Yonamine, M.; Shimada, K.; Nagamine, T.; Shimabukuro, M.; Gibo, H. Screening of antioxidant action of various molds and protection of Monascus anka against experimentally induced liver injuries of rats Gen. Pharmacol. 1999, 32, 225-231 (Pubitemid 29127120)
6. Keisuke, T.; Tomio, I.; Nobukazu, T.; Hiroshi, O.; Shirou, A.; Shouichi, T.; Yasue, N. Extraction of hypotensive substance from wheat beni-koji Nippon Shokuhin Kogyo Gakkaishi 1992, 39, 913-918
7. Lee, C. L.; Tsai, T. Y.; Wang, J. J.; Pan, T. M. In vivo hypolipidemic effects and safety of low dosage Monascus powder in a hamster model of hyperlipidemia Appl. Microbiol. Biotechnol. 2006, 70, 533-540
8. Wu, C. L.; Lee, C. L.; Pan, T. M. Red mold dioscorea has greater anti-hypertensive effect than traditional red mold rice in spontaneously hypertensive rats J. Agric. Food Chem. 2009, 57, 5035-5041
9. Lee, C. L.; Hung, H. K.; Wang, J. J.; Pan, T. M. Red mold dioscorea has greater hypolipidemic and antiatherosclerotic effect than traditional red mold rice and unfermented dioscorea in hamsters J. Agric. Food Chem. 2007, 55, 7162-7169
10. Lee, C. L.; Wang, J. J.; Kuo, S. L.; Pan, T. M. Monascus fermentation of dioscorea for increasing the production of cholesterol-lowering agent-monacolin K and antiinflammation agent-monascin Appl. Microbiol. Biotechnol. 2006, 72, 1254-1262
11. Ho, B. Y.; Pan, T. M. The Monascus metabolite, monacolin K, reduces tumor progression and metastasis of Lewis lung carcinoma cells J. Agric. Food Chem. 2009, 57, 8258-8265
12. Akihisa, T.; Tokuda, H.; Ukiya, M.; Kiyota, A.; Yasukawa, M. Anti-tumor-initiating effects of monascin, an anzaphilonoid pigment from the extract of Monascus pillosus fermented rice (red-mold rice) Chem. Biodiversity 2007, 2, 1305-1309
13. Martinková, L.; Patáková-Juzlová, P.; Kren, V.; Kucerová, Z.; Havlicek, V.; Olsovsky, P.; Hovorka, O.; Rihová, B.; Vesely, D.; Veselá, D.; Ulrichová, J.; Prikrylová, V. Biological activities of oligoketide pigments of Monascus purpureus Food Addit. Contam. 1999, 16, 15-24
14. Lin, W. Y.; Hsu, W. Y.; Hish, C. H.; Pan, T. M. Proteome changes in Caco-2 cells treated with Monascus -fermented red mold rice extract J. Agric. Food Chem. 2007, 55, 8987-8994
15. Tsai, R. L.; Ho, B. Y.; Pan, T. M. Red mold rice mitigates oral carcinogenesis in 7,12-dimethyl-1,2-benz[a]anthracene-induced oral carcinogenesis in hamster. Evidence Based Complementary Altern. Med. 2009, Advance Access published on December 17.
16. Su, Y. C.; Wang, J. J.; Lin, T. T.; Pan, T. M. Production of the secondary metabolites γ-aminobutyric acid and monacolin K by Monascus J. Ind. Microbiol. Biotechnol. 2003, 30, 41-46
17. Zhang, D. Y.; Wu, J.; Ye, F.; Xue, L.; Jiang, S.; Yi, J. Inhibition of cancer cell proliferation and prostaglandin E2 synthesis by Scutellaria Baicalensis Cancer Res. 2003, 63, 4037-4043
18. Kuo, Y. H.; Huang, H. C.; Kuo Yang, L. M.; Hsu, Y. W.; Lee, K. H.; Chang, F. R.; Wu, Y. C. New dammarane-type saponins from the galls of Sapindus mukorossi J. Agric. Food Chem. 2005, 53, 4722-4727
19. Kimura, T.; Nishida, M.; Kuramochi, K.; Sugawara, F.; Yoshida, H.; Mizushina, Y. Novel azaphilones, kasanosins A and B, which are specific inhibitors of eukaryotic DNA polymerases β and λ from Talaromyces sp Bioorg. Med. Chem. 2008, 16, 4594-4599