菌體成分に關する研究 (第7報) : Fungisterol の構造に就て (其の1)

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Fungisterol was isolated by TANRET from ergot and thereafter studied by Heyl et al., who thought its chemical structure to be completely unsaturated in the steroid ring or to habe two more hydrogen atoms than ergosterol and to be the mixture of α-dihydroergosterol and its unknown isomer.Crude fungisterol (m. p. [146/8℃]was obtained from the mycelium of Penicilium chrysogenum grown in submerged culture.After saponifying fungisterol acetate (m. p. [158.5℃], [α]^<15>_D=-15.7°)which was obtained by acetylatin of the crude fungisterol and recrystallization repeated 6 times of so obtained acetate, fungisterol (m. p. [147.5℃], [α]^<15>_D=-21.9°)was obtained in crystalline plate, which was moreover recrystallized 18 times-8 times from alcohol and ether (1 : 1), 2 times from ethyl acetate and 8 times from alcohol.The chemical structure of fungisterol was partially made clear by the comparison of its ultraviolet absorption spectrum with that of pure cholesterol, ergosterol and α-dihydroergosterol, under simultaneous application of DIMROTH's results concerning the relation between absorption maxima or absorption cofficients and the chemical structure of sterids. (ct. Fig. 1〜2 in the text.)In conclusion, the chemical structure of fungisterol-absorption maxima at 260?, 271,281.8 and 294 m/μ ; E _282 m/μ=9980-is alike to ergosterol, and seems to have conjugated double bond in the steroid nucleus.The author will report in next time on some chemical behaviors, the structure of nucleus and side chain, and the position of double bond in detail.
社団法人日本生物工学会の論文
1951-12-15

菌體成分に關する研究 (第7報) : Fungisterol の構造に就て (其の1)

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