New diketopiperazines from the entomopathogenic fungus Verticillium hemipterigenum BCC 1449.

Two new diketopiperazines, bisdethiodi(methylthio)-1-demethylhyalodendrin and 1-demethylhyalodendrin tetrasulfide, together with two known cyclodepsipeptides, enniatins B and B4, and two known pyrones, pyrenocines A and B, were isolated from a culture broth of the entomopathogenic fungus Verticillium hemipterigenum BCC 1449. These structures were elucidated using spectroscopic methods and X-ray crystallography. Antimalarial and cytotoxic activities of these compounds were evaluated.

[1]  M. Tanticharoen,et al.  Unusual enniatins produced by the insect pathogenic fungus Verticillium hemipterigenum: isolation and studies on precursor-directed biosynthesis , 2003 .

[2]  S. Wren,et al.  Novel inhibitors of plasminogen activator inhibitor-1: development of new templates from diketopiperazines. , 2002, Bioorganic & medicinal chemistry letters.

[3]  Y. Sugie,et al.  A new antibiotic CJ-17,665 from Aspergillus ochraceus. , 2001, The Journal of antibiotics.

[4]  I. Donkor,et al.  Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus. , 2001, Bioorganic & medicinal chemistry letters.

[5]  N. Hywel-Jones,et al.  Bioxanthracenes from the Insect Pathogenic Fungus Cordyceps pseudomilitaris BCC 1620. Part 1. Taxonomy, Fermentation, Isolation and Antimalarial Activity. , 2001 .

[6]  J. Davide,et al.  Oxo-piperazine derivatives of N-arylpiperazinones as inhibitors of farnesyltransferase. , 2001, Bioorganic & medicinal chemistry letters.

[7]  N. Hywel-Jones,et al.  Bioxanthracenes from the insect pathogenic fungus. Cordyceps pseudomilitaris BCC 1620. I. Taxonomy, fermentation, isolation and antimalarial activity. , 2001, The Journal of antibiotics.

[8]  Y. Tsantrizos,et al.  Novel quinazolinones and enniatins from Fusarium lateritium Nees , 1993 .

[9]  William P. Janzen,et al.  Balanol: a novel and potent inhibitor of protein kinase C from the fungus Verticillium balanoides , 1993 .

[10]  S. Ōmura,et al.  New cyclodepsipeptides, enniatins D, E and F produced by Fusarium sp. FO-1305. , 1992, The Journal of antibiotics.

[11]  J. Miller,et al.  Production of enniatins by Fusarium acuminatum and Fusarium compactum in liquid culture: isolation and characterization of three new enniatins, B2, B3, and B4 , 1992 .

[12]  I. Kawamoto,et al.  ES-242-1, a novel compound from Verticillium sp., binds to a site on N-methyl-D-aspartate receptor that is coupled to the channel domain. , 1992, The Journal of antibiotics.

[13]  D. Scudiero,et al.  New colorimetric cytotoxicity assay for anticancer-drug screening. , 1990, Journal of the National Cancer Institute.

[14]  D. Rast,et al.  Bisvertinols: a new group of dimeric vertinoids from verticillium intertextum , 1986 .

[15]  D. Rast,et al.  ISOLATION OF FOUR HEXAKETIDES FROM VERTICILLIUM INTERTEXTUM , 1982 .

[16]  Takeshi Matsumoto,et al.  X-Ray Crystal Structure of Pyrenocine A, a Phytotoxin from Pyrenochaeta terrestris , 1981 .

[17]  S. Yamamura,et al.  Isolation and structure of citreopyrone, a metabolite of biourge , 1980 .

[18]  J. Haynes,et al.  Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique , 1979, Antimicrobial Agents and Chemotherapy.

[19]  S. Sakamura,et al.  Phytotoxins Produced by Onion Pink Root Fungus, Pyrenochaeta terrestris , 1979 .

[20]  M. Kakushima,et al.  An Epitetrathiodioxopiperazine with 3S,6S Configuration from Hyalodendron sp. , 1975 .

[21]  M. Kakushima,et al.  An Epitetrathiodioxopiperazine with 3 S ,6 S Configuration from Hyalodendron sp. , 1975 .

[22]  M. Kakushima,et al.  Metabolites of Hyalodendron sp.: Bisdethiodi(methylthio)hyalodendrin , 1974 .

[23]  K. Michel,et al.  Epipolythiopiperazinedione antibiotics from Penicillium turbatum. , 1974, The Journal of antibiotics.

[24]  W. Rosenbrook,et al.  A novel class of diketopiperazines. , 1973, The Journal of antibiotics.

[25]  M. Matsumoto,et al.  Studies on the metabolites of Verticillium sp. structures of Verticillins A, B, and C. , 1973, Journal of the Chemical Society. Perkin transactions 1.

[26]  H. Loosli,et al.  [Isolation of 11 , 11' -dihydroxychaetocin from Verticillium tenereum]. , 1972, Helvetica chimica acta.

[27]  P. Plattner,et al.  Welkstoffe und Antibiotika. 7. Mitteilung. Über die Isolierung neuartiger Antibiotika aus Fusarien , 1948 .