Structure-activity relationships for unsaturated dialdehydes. 10. The generation of bioactive products by autoxidation of isovelleral and merulidial.

M Jonassohn, H Anke, P Morales, O Sterner
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引用次数: 13

Abstract

The autoxidation of the two mutagenic and antimicrobial sesquiterpenes merulidial (1a) and isovelleral (5) generates a number of bioactive products that are suggested to be partly responsible for the mutagenic and antimicrobial activities of the two compounds. The biological activities of the autoxidation products are, as far as has been possible to assay, of the same order as the parent compounds, and it is shown that they are formed in normal bioassay media. Merulidial (1a) is especially interesting, as its rate of autoxidation is considerably higher compared with non-mutagenic derivatives of 1a. In addition, natural isovelleral [(+/-)-5] was found to be twice as mutagenic as synthetic isovelleral [(+/-)-5], indicating that (-)-isovelleral is only weakly active or inactive, and supporting the suggestion that the interaction of isovelleral (5) and its derivatives with DNA depends on the absolute stereochemistry of the unsaturated dialdehyde moiety.

不饱和二醛的构效关系。10. 异柳醛和多柳醛自氧化生成生物活性产物。
两种诱变和抗菌倍半萜多柳二烯(1a)和异柳六烯(5)的自氧化产生了许多生物活性产物,这些产物被认为是这两种化合物的诱变和抗菌活性的部分原因。自氧化产物的生物活性,就可能的测定而言,与母体化合物具有相同的顺序,并且表明它们是在正常的生物测定介质中形成的。多柳醚(1a)特别有趣,因为与1a的非诱变衍生物相比,其自氧化率要高得多。此外,天然异vellal[(+/-)-5]的诱变性是合成异vellal[(+/-)-5]的两倍,这表明(-)-异vellal仅具有弱活性或无活性,并支持异vellal(5)及其衍生物与DNA的相互作用取决于不饱和双醛部分的绝对立体化学。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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