title: Terpenoids produced by actinomycetes: isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088.
abstract: New terpenoids named gifhornenolones A (1) and B (2) were isolated from the culture broth of Verrucosispora gifhornensis YM28-088, and their structures were established as hydroxylated isopimaradiene derivatives on the basis of extensive NMR and MS spectral analyses. In addition, a known sesquiterpene compound cyperusol C (3) was isolated. The absolute configuration of 1 was determined by nuclear Overhauser effect spectroscopy (NOESY) and CD spectra as 4R, 5S, 9R, 10S, 13R, and that of 2 was determined by NOESY experiments as 3R, 4R, 5R, 9R, 10S, 13R. Labeling experiments with [1-(13)C]glucose and [U-(13)C(6)]glucose confirmed that the MEP (2-C-methyl-D-erythritol-4-phosphate) pathway was used for the biosynthesis of terpenoids in this organism. 1 showed potent inhibitory activity to the androgen receptor with an IC(50) of 2.8 microg ml(-1).
authors.affiliation: Department of Applied Biology and Chemistry, Faculty of Applied Bioscience, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Shirai
authors.forename: Masaaki
authors.initials: M
authors.lastname: Okuda
authors.forename: Keiichiro
authors.initials: K
authors.lastname: Motohashi
authors.forename: Masaya
authors.initials: M
authors.lastname: Imoto
authors.forename: Kazuo
authors.initials: K
authors.lastname: Furihata
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Matsuo
authors.forename: Atsuko
authors.initials: A
authors.lastname: Katsuta
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Shizuri
authors.forename: Haruo
authors.initials: H
authors.lastname: Seto
mesh_terms: D039903:Actinobacteria / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000900:Anti-Bacterial Agents; D004224:Diterpenes; C550111:gifhornenolone A; C550112:gifhornenolone B