Secondary Metabolites from the Fungus Monascus purpureus and Evaluation of Their Cytotoxic Activity
Corresponding Author
Ming-Jen Cheng
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Corresponding author for chemical aspects of the work.
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))Search for more papers by this authorPing-Hsun Yang
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Search for more papers by this authorMing-Der Wu
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Search for more papers by this authorIh-Sheng Chen
College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, R.O.C.
Search for more papers by this authorMing-Tsuen Hsieh
School of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, College of Pharmacy, China Medical University, Taichung, 404 Taiwan, R.O.C.
Search for more papers by this authorYen-Lin Chen
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Search for more papers by this authorCorresponding Author
Gwo-Fang Yuan
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Corresponding author for general information.
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))Search for more papers by this authorCorresponding Author
Ming-Jen Cheng
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Corresponding author for chemical aspects of the work.
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))Search for more papers by this authorPing-Hsun Yang
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Search for more papers by this authorMing-Der Wu
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Search for more papers by this authorIh-Sheng Chen
College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, R.O.C.
Search for more papers by this authorMing-Tsuen Hsieh
School of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, College of Pharmacy, China Medical University, Taichung, 404 Taiwan, R.O.C.
Search for more papers by this authorYen-Lin Chen
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Search for more papers by this authorCorresponding Author
Gwo-Fang Yuan
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))
Corresponding author for general information.
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan, R.O.C. (phone: +886-3-522-3191 (ext 568))Search for more papers by this authorAbstract
Investigation of the 95% EtOH extract of red yeast rice fermented with the fungus Monascus purpureus BCRC 31615 has led to the isolation and structure elucidation of four new compounds, including one new azaphilone analog, monascuspurpurone (1), a new isocoumarin, monaschromone (2), a new furan-3-one derivative, 2-dodecyl-5-(2-methoxyethyl)-2-methylfuran-3(2H)-one (3), and a new alkaloid, methyl 4-[(E)-2-acetyl-4-oxoundec-1-enyl]-6-propylnicotinate (4), together with seven known compounds. The structures of all isolates were elucidated on the basis of extensive spectroscopic analyses and comparison with literature data. Compounds 1–4 were tested for their cytotoxicity against the MCF-7, NCI-H460, and SF-268 cell lines using the MTT (=3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) assay. Among them, compounds 1 and 4 were found to have moderate cytotoxic effects against these three cell lines in vitro.
References
- 1 J. Ma, Y. Li, Q. Ye, J. Li, Y. Hua, D. Ju, D. Zhang, R. Cooper, M. Chang, J. Agric. Food Chem. 2000, 48, 5220.
- 2 R. E. Mudgett, ‘Monascus’, in ‘Natural Food Colorants: Science and Technology’, Vol. 14, Eds. G. J. Lauro, F. J. Francis, Marcel Dekker, New York, 2000, p. 31.
- 3 K. Tsuji, T. Ichikawa, N. Tanabe, S. Abe, S. Tarui, Y. Nakagawa, Nippon Nogeikagaku Kaishi 1992, 66, 1241.
- 4 A. Endo, J. Antibiot. 1979, 32, 852.
- 5 A. Endo, J. Med. Chem. 1985, 28, 401.
- 6 L. Martinokova, P. Juzlova, D. Vesely, J. Appl. Bacteriol. 1995, 79, 609.
- 7 A. Endo, D. Komagata, H. Shimada, J. Antibiot. 1986, 39, 1670.
- 8 P. J. Blanc, M. O. Loret, A. L. Santerre, A. Pareilleux, D. Prome, I. C. Prome, J. P. Laussac, G. Goma, J. Food Sci. 1994, 59, 862.
- 9 P. Jůzlová, L. Martínková, V. Křen, J. Ind. Microbiol. 1996, 16, 163.
- 10 T. Akihisa, H. Tokuda, K. Yasukawa, M. Ukiya, A. Kiyota, N. Sakamoto, T. Suzuki, N. Tanabe, H. Nishino, J. Agric. Food Chem. 2005, 53, 562.
- 11 H. Nozaki, S. Date, H. Kondo, H. Kiyohara, D. Takaoka, T. Tada, M. Nakayama, Agric. Biol. Chem. 1991, 55, 899.
- 12 P. J. Blanc, M. O. Loret, G. Goma, Biotechnol. Lett. 1995, 17, 291.
- 13 K. Sato, Y. Goda, S. S. Sakamoto, H. Shibata, T. Maitani, T. Yamada, Chem. Pharm. Bull. 1997, 45, 227.
- 14 S. Jongrungruangchok, P. Kittakoop, B. Yongsmith, R. Bavovada, S. Tanasupawat, N. Lartpornmatulee, Y. Thebtaranonth, Phytochemistry 2004, 65, 2569.
- 15 Z. Huang, Y. Xu, L. Li, Y. Li, J. Agric. Food Chem. 2008, 56, 112.
- 16 D. Wild, G. Tóth, H.-U. Humpf, J. Agric. Food Chem. 2002, 50, 3999.
- 17 T. Akihisa, S. Mafune, M. Ukiya, Y. Kimura, K. Yasukawa, T. Suzuki, H. Tokuda, N. Tanabe, T. Fukuoka, J. Nat. Prod. 2004, 67, 479.
- 18 C. F. Hossain, E. Okuyama, M. Yamazaki, Chem. Pharm. Bull. 1996, 44, 1535.
- 19 D. Wild, G. Tóth, H.-U. Humpf, J. Agric. Food Chem. 2003, 51, 5493.
- 20 M.-J. Cheng, M.-D. Wu, I.-S. Chen, G.-F. Yuan, Chem. Pharm. Bull. 2008, 56, 394.
- 21 Y.-M. Bi, X.-B. Bi, Q.-R. Zhao, Y.-T. Chen, J.-L. Xie, Helv. Chim. Acta 2004, 87, 2890.
- 22 L. Camarda, L. Merlini, G. Nasini, Phytochemistry 1976, 15, 537.
- 23 A. S. Feliciano, A. F. Barrero, M. Medarde, J. M. M. Del Corral, M. V. Calle, Phytochemistry 1983, 22, 2031.
- 24 I. Zabetakis, J. W. Gramshaw, D. S. Robinson, Food Chem. 1999, 65, 139.
- 25 J. He, E. M. K. Wijeratne, B. P. Bashyal, J. Zhan, C. J. Seliga, M. X. Liu, E. E. Pierson, L. S. Pierson, H. D. VanEtten, A. A. L. Gunatilaka, J. Nat. Prod. 2004, 67, 1985.
- 26 M. A. R. Serrano, M. Pivatto, W. Francisco, A. Danuello, L. O. Regasini, E. M. C. Lopes, M. N. Lopes, M. C. M. Young, V. S. Bolzani, J. Nat. Prod. 2010, 73, 482.
- 27 L. L. Li, J. P. Chen, L. Y. Kong, Chin. J. Nat. Med. 2006, 4, 32.
- 28 H. C. Chiang, S. C. Chu, J. Chin. Chem. Soc. 1991, 38, 71.
- 29 N. K. N. Yee, R. M. Coates, J. Org. Chem. 1992, 57, 4598.
- 30 H. Achenbach, A. Schwinn, Phytochemistry 1995, 38, 1037.
- 31 S.-T. Chang, S.-S. Cheng, S.-Y. Wang, J. Chem. Ecol. 2001, 27, 717.
- 32 J. Hargreaves, J. O. Park, E. L. Ghisalberti, K. Sivasithamparam, B. W. Skelton, A. H. White, J. Nat. Prod. 2002, 65, 7.
- 33 R. S. Gieni, Y. Li, K. T. HayGlass, J. Immunol. Methods 1995, 187, 85.
- 34 M. Johansson, B. Köpcke, H. Anke, O. Sterner, J. Antibiot. 2002, 55, 104.
