菌類によるアルカロイドおよび関連物質の生産-8-ペプチド型麦角アルカロイド類の生成機構

概要

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Formation of peptide portions of peptide-type ergot alkaloids has been studied by the use of some radioactive prolyldiketopiperazines and the intact mycelia of two ergot strains which are productive of ergokryptine_??_ergokryptinine or ergotamine_??_ergotaminine as the main alkaloid. L-Leucyl-D-proline-lacta-3H as well as L-leucyl-L-proline-lactam-3H were shown to be incorporated into ergokryptine_??_ergokryptinine, while L-phenylalanyl-D-proline-lactam as well as L-phenylalanyl-L-proline-lactam were shown to be incorporated into ergotamine_??_ergotaminine. The radioactive ergokryptinine and ergotaminine formed by the incorporation of L-leucyl-D-proline-lactam 3H and L-phenylalanyl-D-proline-lactam-3H, respectively, were isolated and recrystallized from methanol with carrier materials, and identified by melting point as well as by thin-layer chromatography. The specific activities of the isolates did not change over several recrystallizations. These findings indicate that the incorporation of prolyldiketopiperazines having D-proline configuration into peptide-type alkaloids was effected after the substrates were converted to those having L-proline configuration in the employed mycelia. From the present results, the mechanism of the formation of peptide-type ergot alkaloids was brought to light to a certain extent.
社団法人日本農芸化学会の論文