The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
STRUCTURE-ACTIVITY RELATIONSHIPS OF VIRGINIAE BUTANOLIDE C, AN INDUCER OF VIRGINIAMYCIN PRODUCTION IN STREPTOMYCES VIRGINIAE
TAKUYA NIHIRAYOSHIHIRO SHIMIZUHYUN Soo KIMYASUHIRO YAMADA
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1988 Volume 41 Issue 12 Pages 1828-1837

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Abstract

Virginiae butanolide C, [2-(1'-hydroxyhexyl)-3-(hydroxymethyl)butanolide (3)], is one of the inducers of virginiamycin production in Streptomyces virginiae. Various racemic analogues were synthesized, and their effectiveness in virginiamycin induction was studied. Among analogues having a series of C-2 side chains, those with 1'-hydroxyheptyl or 1'-hydroxyoctyl moiety were most effective with a minimum effective concentration of 0.8 ng/ml. At the same length of C-2 side chain, a 2, 3-cis analogue was 10-fold more active than a 2, 3-trans analogue, and the 2, 3-trans analogue was 10-fold more active than an analogue having a 1'-ketoalkyl moiety at C-2 (A-factor type analogue). Methoxylation or deletion of either ' one of the two hydroxy groups in virginiae butanolide C analogues caused a 100 to 1, 000-fold decrease in activity, thus indicating the importance of the two hydroxy groups in virginiamycin induction.

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© Japan Antibiotics Research Association
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