Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Journal of antibiotics, 2010-05, Vol.63 (5), p.245-250

Ort / Verlag

London: Nature Publishing Group UK

Erscheinungsjahr

2010

Quelle

Electronic Journals Library

Beschreibungen/Notizen

• 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 4 R , 5 S , 9 R , 10 S , 13 R , and that of 2 was determined by NOESY experiments as 3 R , 4 R , 5 R , 9 R , 10 S , 13 R . 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  μ g ml −1 .