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 lg ml À1 .
Terpenoids Produced by Actinomycetes: Isolation, Structural Elucidation and Biosynthesis of New Diterpenes, Gifhornenolones A and B from Verrucosispora gifhornensis YM28-088. -Labeling experiments confirm that the MEP (2-C-methyl-D-erythritol-4-phosphate) pathway is used for the biosynthesis of gifhornenolone A (I) and B (II) in the title microorganism. Because of its structural similarity to steroidal compounds (I) shows potent androgen antagonist activity. -(SHIRAI, M.; OKUDA, M.; MOTOHASHI, K.; IMOTO, M.; FURIHATA, K.; MATSUO, Y.; KATSUTA, A.; SHIZURI, Y.; SETO*, H.; J.
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