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 language | English |
|---|---|
| Pages (from-to) | 245-250 |
| Number of pages | 6 |
| Journal | Journal of Antibiotics |
| Volume | 63 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 2010 May |
Fingerprint
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 journal › Article
}
TY - JOUR
T1 - Terpenoids produced by actinomycetes
T2 - Isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088
AU - Shirai, Masato
AU - Okuda, Masaaki
AU - Motohashi, Keiichiro
AU - Imoto, Masaya
AU - Furihata, Kazuo
AU - Matsuo, Yoshihide
AU - Katsuta, Atsuko
AU - Shizuri, Yoshikazu
AU - Seto, Haruo
PY - 2010/5
Y1 - 2010/5
N2 - 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.
AB - 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.
KW - Androgen receptor binding inhibitor
KW - Biosynthesis
KW - Cyperusol C
KW - Gifhornenolone
KW - Terpenoid
KW - Verrucosispora gifhornensis
UR - http://www.scopus.com/inward/record.url?scp=77952923683&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77952923683&partnerID=8YFLogxK
U2 - 10.1038/ja.2010.30
DO - 10.1038/ja.2010.30
M3 - Article
C2 - 20379218
AN - SCOPUS:77952923683
VL - 63
SP - 245
EP - 250
JO - Journal of Antibiotics
JF - Journal of Antibiotics
SN - 0021-8820
IS - 5
ER -