72(P47) Gelasinospora属子嚢菌3種からの免疫調節活性成分(ポスター発表の部)
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概要
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In our screening project on immunomodulatory constituents of fungi, six new immunosuppressive α-pyrones named multiforisins A-F have so far been isolated from Gelasinospora multiforis. Successively, it was found that the crude extracts of Gelasinospora heterospora and G. santi-florii showed immunosuppressive activity. Among the four constituents 1-4 isolated from Gelasinospora heterospora, 1-3 exhibited immunosuppressive activity. The spectral data including two dimensional ^1H- and ^<13>C-NMR and the chemical correlation to multiforisins A(5) and B(6), indicated that 3, 1 and 4, which were also isolated from G. multiforis together with 5 this time, were elucidated to be new homologues of the multiforisins and named multiforisins G, H, and I, respectively (Chart 1). Compound 2, which were also isolated from G. santi-florii this time, was deduced to be identical with sordarial from Sordaria macrospora. The absolute configurations at positions 3' and 4' in 2, which had been not yet decided, were finally determined to be R and S, respectively (Chart 2). Among the six constituents 2 and 11-15 isolated from G. santi-florii, 12, 2 and 11 exhibited immunosuppressive activity. The main active principle 12 and an inactive one 13 were identical with seco-anthraquinone-type compounds, nidulalins A and B, from Emericella nidulans var lata, respectively. Compounds 15 and 11 were deduced to be new compounds related to 12, and 14 was found to be identical with 1-hydroxy-3-methylxanthone from Anixiella micropertusa, as shown in Chart 3. To our knowledge, this is the first time that sordarial and nidulalin A have been isolated as immunosuppressive constituents from natural source. The immunosuppressive activities (IC_<50> values) of 1-6, 11-16 and the three compounds as positive control in Table 1 suggested that the presence of ?CH_2OH at position 3 or 5 in the multiforisins and that of the unique A-ring moiety in 12 were very important for the appearance of the immunosuppressive activities of the multiforisins and 12, respectively. Investigation on the mode of action of 12 suggested that the immunosuppressive effect of 12 was not due to the ability to inhibit IL-2 production.
- 天然有機化合物討論会の論文
- 1998-08-31
著者
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山口 健太郎
千葉大分析セ
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山口 健太郎
千葉大学分析センター
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山崎 幹夫
千葉大薬
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山崎 幹夫
千葉大学薬学部
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藤本 治宏
千葉大院薬
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奥山 恵美
千葉大院薬
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山崎 幹夫
千葉大学薬学部医薬品素材学講座
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奥山 恵美
千葉大学 院薬
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奥山 恵美
千葉大薬
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角野 めぐみ
千葉大薬
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藤本 治宏
千葉大薬
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金 容必
千葉大薬
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永野 順子
千葉大薬
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藤本 治宏
Chiba Univ. Chiba Jpn
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