麦角菌の生産する1新プロリルジケトピペラジンについて菌類によるアルカロイドおよび関連物質の生産 (第13報)

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The authors have examined the structure of the prolyldiketopiperazine “B” which was previously(1) found in the sclerotia and saprophytic cultures of Elymus-type ergot fungus. From the physico- and spectro-chemical data, it was found that “B” must be constituted from D-proline and a new L-amino acid “X” which was presumed to be L-homoleucine. “X” was obtained in crystalline form from the acid hydrolyzate of “B”; C7H15NO2, mp 211_??_215°C (decomp.), [α]25D+25°(c=0.2, 6 N HCl). On the other hand, the authentic L-homoleucine was prepared by treating the synthetic 5-methyl-2-amino-hexanoic acid (D, L-homoleucine) of S. David and J. -C. Fisher(5) with D-amino acid oxidase (pig kidney, Miles Lab., Inc). It was found that “X” is identical in all respects with the authentic L-homoleucine, and by this finding, it was confirmed that “B” is nothing but a new compound, L-homoleucyl-D-proline-lactam. From the present result together with that obtained in previous experiment, (6) the structures of two peptide-type ergot alkaloids, “P1” (ergohexine) and “P2” (ergoheptine) could be proposed for the first time.
社団法人日本農芸化学会の論文