Terpendole E, a kinesin Eg5 Inhibitor, is a key biosynthetic intermediate of indole-diterpenes in the producing fungus Chaunopycnis alba

Chemistry and Biology

Volumn 19, Issue 12, 2012, Pages 1611-1619

  Motoyama, Takayuki ^a   Hayashi, Toshiaki ^a   Hirota, Hiroshi ^a   Ueki, Masashi ^a   Osada, Hiroyuki ^a  

^a RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

13 DESOXYPAXILLINE; DITERPENE; INDOLE; PASPALINE; TERB PROTEIN; TERC PROTEIN; TERF PROTEIN; TERK PROTEIN; TERM PROTEIN; TERP PROTEIN; TERPENDOLE E; TERPENE; TERQ PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CHAUNOPYCNIS ALBA; CHEMICAL STRUCTURE; DEMETHYLATION; FUNGUS; GENE CLUSTER; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; WILD TYPE;

ANTINEOPLASTIC AGENTS; ASCOMYCOTA; DITERPENES; GENES, FUNGAL; HUMANS; INDOLES; KINESIN; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY;

CHAUNOPYCNIS ALBA; FUNGI;

EID: 84871542194     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2012.10.010     Document Type: Article

References (22)

1. M.J. de Groot, P. Bundock, P.J. Hooykaas, and A.G. Beijersbergen Agrobacterium tumefaciens-mediated transformation of filamentous fungi Nat. Biotechnol. 16 1998 839 842
2. R.T. Gallagher, E.P. White, and P.H. Mortimer Ryegrass staggers: isolation of potent neurotoxins lolitrem A and lolitrem B from staggers-producing pastures N. Z. Vet. J. 29 1981 189 190
3. X.H. Huang, H. Nishida, H. Tomoda, N. Tabata, K. Shiomi, D.J. Yang, H. Takayanagi, and S. Omura Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. II. Structure elucidation of terpendoles A, B, C and D J. Antibiot. 48 1995 5 11
4. X.H. Huang, H. Tomoda, H. Nishida, R. Masuma, and S. Omura Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. I. Production, isolation and biological properties J. Antibiot. 48 1995 1 4
5. T. Itoh, K. Tokunaga, Y. Matsuda, I. Fujii, I. Abe, Y. Ebizuka, and T. Kushiro Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases Nat. Chem. 2 2010 858 864
6. S.D. Knight, and C.A. Parrish Recent progress in the identification and clinical evaluation of inhibitors of the mitotic kinesin KSP Curr. Top. Med. Chem. 8 2008 888 904
7. S.M. Li Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis Nat. Prod. Rep. 27 2010 57 78
8. T. Motoyama, K. Kadokura, T. Ohira, A. Ichiishi, M. Fujimura, I. Yamaguchi, and T. Kudo A two-component histidine kinase of the rice blast fungus is involved in osmotic stress response and fungicide action Fungal Genet. Biol. 42 2005 200 212
9. T. Motoyama, N. Ochiai, M. Morita, Y. Iida, R. Usami, and T. Kudo Involvement of putative response regulator genes of the rice blast fungus Magnaporthe oryzae in osmotic stress response, fungicide action, and pathogenicity Curr. Genet. 54 2008 185 195
10. S.C. Munday-Finch, A.L. Wilkins, C.O. Miles, H. Tomoda, and S. Omura Isolation and structure elucidation of lolilline, a possible biosynthetic precursor of the lolitrem family of tremorgenic mycotoxins J. Agric. Food Chem. 45 1997 199 204 10.1021/jf960396r
11. J. Nakazawa, J. Yajima, T. Usui, M. Ueki, A. Takatsuki, M. Imoto, Y.Y. Toyoshima, and H. Osada A novel action of terpendole E on the motor activity of mitotic Kinesin Eg5 Chem. Biol. 10 2003 131 137
12. M.J. Nicholson, A. Koulman, B.J. Monahan, B.L. Pritchard, G.A. Payne, and B. Scott Identification of two aflatrem biosynthesis gene loci in Aspergillus flavus and metabolic engineering of Penicillium paxilli to elucidate their function Appl. Environ. Microbiol. 75 2009 7469 7481
13. H.S. Rho, S. Kang, and Y.H. Lee Agrobacterium tumefaciens-mediated transformation of the plant pathogenic fungus, Magnaporthe grisea Mol. Cells 12 2001 407 411
14. S. Saikia, E.J. Parker, A. Koulman, and B. Scott Defining paxilline biosynthesis in Penicillium paxilli: functional characterization of two cytochrome P450 monooxygenases J. Biol. Chem. 282 2007 16829 16837
15. S. Saikia, M.J. Nicholson, C. Young, E.J. Parker, and B. Scott The genetic basis for indole-diterpene chemical diversity in filamentous fungi Mycol. Res. 112 2008 184 199
16. J. Sambrook, E.F. Fritsch, and T. Maniatis Molecular Cloning: A Laboratory Manual 1989 Cold Spring Harbor Laboratory Cold Spring Harbor, New York
17. V. Sarli, and A. Giannis Targeting the kinesin spindle protein: basic principles and clinical implications Clin. Cancer Res. 14 2008 7583 7587
18. H. Tomoda, N. Tabata, D.J. Yang, H. Takayanagi, and S. Omura Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. III. Production, isolation and structure elucidation of new components J. Antibiot. 48 1995 793 804
19. C. Young, L. McMillan, E. Telfer, and B. Scott Molecular cloning and genetic analysis of an indole-diterpene gene cluster from Penicillium paxilli Mol. Microbiol. 39 2001 754 764
20. C.A. Young, M.K. Bryant, M.J. Christensen, B.A. Tapper, G.T. Bryan, and B. Scott Molecular cloning and genetic analysis of a symbiosis-expressed gene cluster for lolitrem biosynthesis from a mutualistic endophyte of perennial ryegrass Mol. Genet. Genomics 274 2005 13 29
21. C.A. Young, B.A. Tapper, K. May, C.D. Moon, C.L. Schardl, and B. Scott Indole-diterpene biosynthetic capability of epichloë endophytes as predicted by ltm gene analysis Appl. Environ. Microbiol. 75 2009 2200 2211
22. S. Zhang, B.J. Monahan, J.S. Tkacz, and B. Scott Indole-diterpene gene cluster from Aspergillus flavus Appl. Environ. Microbiol. 70 2004 6875 6883