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Journal ArticleDOI

Ascotoxin (Decumbin), a Metabolite of Ascochyta imperfecta PECK.

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TLDR
In this article, the absolute structure of decumbin was presented as [II] by the following evidences: the configuration about C4 was determined as (S) by the benzoate rule on the tetrahydromonoketone (21).
Abstract
From the mycelium of Ascochyta imperfecta decumbin, C16H24O4, mp 203°C, was obtained in one percent yield.The absolute structure of decumbin was presented as [II] by the following evidences: The configuration about C4 was determined as (S) by the benzoate rule on the tetrahydromonoketone (21). The hydroxyl at C7 is α, because tetrahydrodecumbin (23) showed no intramolecular hydrogen bond, while its C7 epimer (24) did. Ring juncture was determined by ORD of a five membered ketone (16). Two double bonds were found to be trans from IR data. The stereochemistry of decumbin monoepoxide (7), tetrahydropyrans (12 and 13) was also studied. Plant tests of the twenty derivatives of decumbin on lucerne and rape revealed that the growth inhibition activity has close relation with the presence of double bond in the thirteen membered lactone ring.

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Journal ArticleDOI

Über die Isolierung neuer Stoffwechselprodukte aus Penicillium brefeldianum DODGE

TL;DR: In this article, two new mold metabolites, Brefeldin A (C16H24O4) and Brefieldin B (C15H2205), have been isolated from the fermentation broth of a strain of Pefiicillium brefeldia from the DODGE.
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