48 糸状菌の生産する新マクロライドの化学構造と生理活性

概要

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In our search for biologically active substances among fungal metabolites, we have found two new macrolides, pyrenolide A and resorcylide. I. The production of fungal factors regulating their growth and morphological development have recieved increasing interests recently. Our examination focused on these metabolites has now led to the isolation of a new fungal morphogenic substance, designated as pyrenolide A, from the fungus Pyrenophora teres IFO 7508. The structure including its absolute stereochemistry of pyrenolide A was established as shown in 1. Pyrenolide A was active to inhibit the growth of the hyphae of several fungal species, and successively to induce the formation of many irregularly swollen hyphae at low concentration (1-10μg/disc). II. trans- and cis-Resorcylide were isolated as plant growth inhibitors from the culture filtrate of an unidentified species of Penicillium. On the basis of chemical and spectroscopic evidence, the structures of trans- and cis-resorcylide were shown as I and II, respectively. Isomerization of the double bond of α,β-unsaturated ketone in resorcylides and their reactions with some nucleophiles were examined; it was shown that the double bond in I was markedly active, but that in II was inactive. In parallel with the above results, we found that I was much more active than II in biological tests for the growth of plant seedlings and microorganisms.
天然有機化合物討論会の論文
1979-09-20