Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities

Journal of Antibiotics

Volumn 63, Issue 4, 2010, Pages 165-170

  Du, Lin ^a   Feng, Teng ^a   Zhao, Boyu ^a   Li, Dehai ^a   Cai, Shengxin ^a   Zhu, Tianjiao ^a   Wang, Fengping ^b   Xiao, Xiang ^b   Gu, Qianqun ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Alkaloid; Deep ocean; Fungus; Penicillium sp.

Indexed keywords

ACETIC ACID; ALKALOID; MELEAGRIN D; MELEAGRIN E; MEVALONIC ACID; ROQUEFORTINE H; ROQUEFORTINE I; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL CYCLE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL STRAIN; CELL STRAIN A549; CELL STRAIN HL 60; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL STRAIN; HUMAN; HUMAN CELL; MARINE SPECIES; PENICILLIUM; PRIORITY JOURNAL; SEDIMENT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ALKALOIDS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL SURVIVAL; DITERPENES; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; GEOLOGIC SEDIMENTS; HL-60 CELLS; HUMANS; IMIDAZOLES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; SOIL MICROBIOLOGY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

FUNGI; PENICILLIUM SP.;

EID: 77951709222     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.11     Document Type: Article

References (19)

1. Scott, P. M., Merrien, M. A. & Polonsky, J. Roquefortine and iso-fumigaclavine A, metabolites from Penicillium roqueforti. Experientia. 32, 140-142 (1976).
2. Ohmomo, S., Oguma, K., Ohashi, T. & Abe, M. Isolation of a new indole alkaloid, roquefortine D, from the cultures of Penicillium roqueforti. Agric. Biol. Chem. 42, 2387-2389 (1978).
3. Musuku, A et al. Isolation and structure determination of a new roquefortine-related mycotoxin from Penicillium verrucosum VAR. Cyclopium isolated from Cassava. J. Nat. Prod. 57, 983-987 (1994).
4. Kozlovsky, A. G., Vinokurova, N. G., Solov'eva, T. F. & Buzilova, I. G. Nitrogencontaining secondary metabolites of microscopic fungi. Appl. Biochem. Microbiol. 32, 39-48 (1996).
5. Kozlovsky, A. G. et al. A new 16n-carboxyethyl derivative of 3,12-dihydroroquefortin. Heterocycles 60, 1639-1644 (2003).
6. Steyn, P. S. & Vleggaa, R. Roquefortine, an intermediate in the biosynthesis of oxaline in cultures of Penicillium oxalicum. J. Chem. Soc. Chem. Commun. 560-561 (1983).
7. Clark, B., Capon, R. J., Lacey, E., Tennant, S. & Gill, J. H. Roquefortine E, a diketopiperazine from an Australian isolate of Gymnoascusreessii. J. Nat. Prod. 68, 1661-1664 (2005).
8. Kopp, B. & Rehm, H. J. Antimicrobial action of roquefortine. Eur. J. Appl. Microbiol. Biotechnol. 6, 397-401 (1979).
9. Aninat, C., Hayashi, Y., Andre, F. & Delaforge, M. Molecular requirements for inhibition of cytochrome P450 activities by roquefortine. Chem. Res. Toxicol. 14, 1259-1265 (2001).
10. Koizumi, Y., Arai, M., Tomoda, H. & Omura, S. Oxaline, a fungal alkaloid, arrests the cell cycle in M phaseby inhibition of tubulin polymerization. Biochim. Biophys. Acta 1693, 47-55 (2004). (Pubitemid 38970135)
11. Du, L. et al. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron 65, 1033-1039 (2009).
12. Kawai, K., Nozawa, K., Nakajima, S. & Iitaka, Y. Studies on fungal products. VII. The structures of meleagrin and 9-O-p-bromobenzoylmeleagrin. Chem. Pharm. Bull. 32, 94-98 (1984).
13. Yamaguchi, T., Nozawa, K., Nakajima, S., Kawai, K. & Udagawa, S. Absolute configuration of roquefortine C, a tremorgenic mycotoxin. Maikotokishin 34, 29-32 (1991).
14. Kusch, J. & Rehm, H. J. Regulation aspects of roquefortine production by free and Caalginate immobilized mycelia of Penicillium roqueforti. Appl. Microbiol. Biotechnol. 23, 394-399 (1986).
15. Reshetilova, T. A., Vinokurova, N. G., Khmelenina, V. N. & Kozlovskii, A. G. The role of roquefortine in the synthesis of alkaloids meleagrine, glandicolines-a and glandicolines- b, and oxaline in fungi Penicillium glandicola and P.atramentosum. Microbiology 64, 27-29 (1995).
16. Williams, R. M., Stoching, E. M. & Sanz-Cervera, J. F. Biosynthesis of prenylated alkaloids derived from tryptophan. Top. Curr. Chem. 209, 97-173 (2000).
17. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63 (1983).
18. Skehan, P et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl Cancer Inst. 82, 1107-1112 (1990).
19. Du, L et al. Cytotoxic sorbicillinoids and bisorbicillinoids from a marine-derived fungus Trichoderma sp. Chem. Pharm. Bull. 57, 220-223 (2009).