Researches on Ergot Fungus

Journal of the agricultural chemical society of Japan
1955.0

Abstract

It was found that the Elymus-type ergot fungus also can produce alkaloids in saprophytic culture (surface technique) in excellent yield. Ergokryptine, ergokryptinine, ergoclavine, ergosinine and agroclavine, and further a new water-soluble alkaloid, for which we propose the name elymoclavine, were isolated from the culture as well as from the scierotia of the said fungus. Elymoclavine was crystallised from ethyl acetate in monoclinic prisms (Fig. 2); axial angle β=96°, refractive indices nβ′=1.62, nβ’=1.75.↑. It was decomposed at 249° (uncorr.) and had the composition C16H18ON2, [α]20D=-109° (c. 0.4 in ethanol), [α]24D=-143° (c. 0.4 in pyridine). The UV-spectrum of elymoclavine shows the maxima at the vicinity of 227, 283 and 295mμ., typical for agroclavine (Fig. 3). On catalytic hydrogenation it yielded a dihydro-derivative, C16H200N2, which was crystallised from methanol in rhombic prisms (Fis. 4), showing a straight extinction, refractive indices nα=1.66, nβ′=1.68, nγ=1.73, m. p. 283° (uncorr. dec.), [α]20D=-60° (c. 0.13 in ethanol), [α]20D=-92° (c. 0.5 in pyridine). The UV-spectrum of the dihyro-derivative was more or less displaced (Fig. 3). It seemed to be identical with α-dihydro-lysergol (dihydro-lysergol). M. PÖHM discovered by paper chromatography two pairs of new peptide-type alkaloids, ergohexine-ergohexinine and ergoheptine-ergoheptinine, in the scierotia of Elymus mollis TRIN. A. STOLL et al. isolated agroclavine, elymoclavine and anew alkaloid penniclavine from the saprophytic culture of the fungus obtained from the scierotia of Pennisetum typhoideum RICH. S. YAMATODANI et al. confirmed that the dihydro-derivative of elymoclavine above-mentioned was identical with α-dihydro-lysergol. Moreover, - they obtained by the catalytic hydrogenation of elymoclavine another dihydro-derivative which was proved to be identical with β-dihydro-lysergol. © 1955, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.

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