Studies on Biosysnthesis of Insecticidal Indole Alkaloid Okaramines

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Penicillium simplicissimum ATCC 90288, when grown on okara, produces insecticidal indole alkaloid okaramines, which has a unique structure. To clarify the biogenetic pathway of okaramines, several subjects were carried out, and some results are obtained as follows.1) To feed labelled compounds, several media for liquid culture were tested. Czapek medium exsibited good growth and good production of okaramines in the presence of methanol extract of okara.2) Labelled tryptophan was added to the liquid culture, and okaramine B was isolated. Mass spectrum of the isolated okaramine B strongly indicated that indole parts of okaramines are derived from tryptophan.3) Okara and soyabean are strongly suggested to have some factors which induce okaramine production by P.simplicissimum ATCC 90288. A bioassay system for evaluating okaramine production was established, and these factors were partially purified with this system.4) A okaramine congener, okaramine G,was isolated from ATCC 90288, and the structure was elucidated.5) Investigation of terpene-related compounds produced by ATCC 90288 led to the isolation of a new oleanane triterpene.6) A new soil isolate Aspergillus aculeatus KF-428 produced okaramines A and B together with new congeners okaramines H and I.