Nihira T, Shimizu Y, Kim H S, Yamada Y
Department of Fermentation Technology, Faculty of Engineering, Osaka University, Japan.
J Antibiot (Tokyo). 1988 Dec;41(12):1828-37. doi: 10.7164/antibiotics.41.1828.
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.
弗吉尼亚丁醇内酯C，即[2-(1'-羟基己基)-3-(羟甲基)丁醇内酯(3)]，是弗吉尼亚链霉菌中维及霉素产生的诱导剂之一。合成了各种外消旋类似物，并研究了它们在维及霉素诱导方面的有效性。在具有一系列C-2侧链的类似物中，那些带有1'-羟基庚基或1'-羟基辛基部分的类似物最有效，最低有效浓度为0.8 ng/ml。在C-2侧链长度相同的情况下，2,3-顺式类似物的活性比2,3-反式类似物高10倍，而2,3-反式类似物的活性比在C-2处具有1'-酮烷基部分的类似物（A因子型类似物）高10倍。弗吉尼亚丁醇内酯C类似物中两个羟基之一的甲氧基化或缺失会导致活性降低100至1000倍，从而表明这两个羟基在维及霉素诱导中的重要性。
