Terpenoids produced by actinomycetes: Isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088

Masato Shirai, Masaaki Okuda, Keiichiro Motohashi, Masaya Imoto, Kazuo Furihata, Yoshihide Matsuo, Atsuko Katsuta, Yoshikazu Shizuri, Haruo Seto

Research output: Contribution to journalArticle

35 Citations (Scopus)

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 Cglucose and U-13 C6 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 IC50 of 2.8 μg ml-1.

Original languageEnglish
Pages (from-to)245-250
Number of pages6
JournalJournal of Antibiotics
Volume63
Issue number5
DOIs
Publication statusPublished - 2010 May

Fingerprint

Actinobacteria
Diterpenes
Terpenes
Spectrum Analysis
Sesquiterpenes
Androgen Receptors
Inhibitory Concentration 50
Glucose
gifhornenolone B
gifhornenolone A
2-C-methylerythritol 4-phosphate

Keywords

  • Androgen receptor binding inhibitor
  • Biosynthesis
  • Cyperusol C
  • Gifhornenolone
  • Terpenoid
  • Verrucosispora gifhornensis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Terpenoids produced by actinomycetes : Isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088. / Shirai, Masato; Okuda, Masaaki; Motohashi, Keiichiro; Imoto, Masaya; Furihata, Kazuo; Matsuo, Yoshihide; Katsuta, Atsuko; Shizuri, Yoshikazu; Seto, Haruo.

In: Journal of Antibiotics, Vol. 63, No. 5, 05.2010, p. 245-250.

Research output: Contribution to journalArticle

Shirai, Masato ; Okuda, Masaaki ; Motohashi, Keiichiro ; Imoto, Masaya ; Furihata, Kazuo ; Matsuo, Yoshihide ; Katsuta, Atsuko ; Shizuri, Yoshikazu ; Seto, Haruo. / Terpenoids produced by actinomycetes : Isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088. In: Journal of Antibiotics. 2010 ; Vol. 63, No. 5. pp. 245-250.
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