菌體成分に關する研究 (第9報) : Fungisterolの化學構造 (其の3)

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概要

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• The author showed in the previous reports that fungisterol (C_<28>H_<44>O) is an isomer of ergosterol, and has one conjugated double bond in one ring of steroid nucleus and the other in side chain -C_9H_<17>. This compound was considered to have a chemical structure different from all the known ergosterol isomers. Irradiating with ultraviolet ray and then treating in the same manner as ergosterol, the product of irradiated fungisterol which has no absorption band at 265 mμ does not produce calciferol. Therefore, it has been concluded that the conjugated double bond in fungisterol nucleus does not lie in the position of carbon atoms 5,6 and 7,8. By the reduction of fungisterol with sodium and absolute propyl alcohol, δ-dihydrofungisterol was obtained, as in the case of catalytic reduction with hydrogen and palladium in etherial solution. The structure of δ-dihydrofungisterol was also determined by the oxidation of its acetate with chromium trioxide, giving Δ^<22>-ergostenol-3-one-7-oxide-8,9 acetate, which was reduced to corresponding ergostanol compound hy catalytic hydrogenation. [figure] On the other hand, α-dihydrofungisteryl acetate was obtained by the catalytic reduction of fungisteryl acetate with hydrogen and palladium in acetic acid solution, and the acetate obtained was epimerised to β-compound by treating with dry hydrochloric acid in chloroform solution. α-dihydrofungisteryl acetate was oxidised with chromium trioxide to Δ^<22>-ergostenol-3-one-7-oxide-8,14 acetate as a main product, which was then reduced to corresponding ergostanol by catalytic hydrogenation. The results obtained from the oxidation were sufficient to conclude that one of the double bonds in the nucleus of fungisterol lies between carbon atoms 8 and 9. For the determination of the chemical structure of fungisterol, some derivatives of its were prepared, and their chemical and physical properties were examined. The author has concluded that the chemical structure of fungisterol is Δ^<6,7 ; 8,9 ; 22,23>-ergostatrienol-3.

• 社団法人日本生物工学会の論文
• 1953-08-15

著者

• 齋藤 耀

  大阪學芸大學

• 齋藤 耀

  大阪學藝大學

関連論文

• 菌體成文に關する研究 (第10報) : Fungisterolの生成機構に關する1考察
• 菌體成文に關する研究 (第9報補遺) Fungisterolの化學構造に就て
• 菌體成分に關する研究 (第9報) : Fungisterolの化學構造 (其の3)
• 菌體成分に關する研究 (第8報) : Fungisterol の化學構造に就て(其の2)
• 菌體成分に關する研究 (第7報補遺) : Fungisterol の赤外線吸收スペクトル
• 菌體成分に關する研究 (第7報) : Fungisterol の構造に就て (其の1)
• 菌體成分に關する研究 (第6報) : 放線菌菌體成分に就て
• 菌体成分に關する研究(第5報) : Aspergillus Sydowiの菌体成分に就いて
• 菌體成分に關する研究(第4報) : ペニシリン生産菌體中のステリン及びアミノ酸に就て
• 菌體成分に關する研究 (第3報) : 椎茸より分離したステリンの紫外線照射による變化に對する一考察
• 菌體成分に關する研究(第2報) : 數種の菌類體中のステリンに就て
• 菌體成分に關する研究(第1報) : ペニシリン菌體中のステリンに就て
• 菌体成分に関する研究-9補遺・10-
• 菌体成分に関する研究-7補遺,8-

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