P-32 インドネシア産キノコMicroporellus subsessilisに含まれる10-phenyl-[11]-cytochalasan(ポスター発表の部)

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In the course of screening for new bioactive compounds from Indonesian mushrooms, the MeOH extract of Microporellus subsessilis was found to induce immotility in Artemia salina. Bioactivity-guided fractionation of this extract revealed six members of the cytochalasin family, including three new 10-phenyl-[11]-cytochalasans (4-6) together with three known derivatives (1-3). Compound 1 was identified as (7S^*,16S^*,18S^*,19R^*)-7,18,19-trihydroxy-16,18-dimethyl-10-phenyl-[11]-cytochalasa-6(12),13(E)-diene-1,2-dione. Compounds 2 and 3 were identified as 19-deoxy and 19-methoxy derivatives of 1, respectively. In compound 4, the six-membered ring of 3 was modified with a double bond newly introduced between C-6 and C-7, and a hydroxymethyl was located at C-6. Compound 5 was also determined as the 7-deoxv-6,7-epoxide of 3. In compound 6, the hydroxyl at C-19 of 1 was acylated with a novel C_<17> fatty acid, 4-methyl-6(E),8(E)-hexadecadienoic acid. The structure of 6 was determined to be (7S^*,16S^*,18S^*,19R^*)-7,18-dihydroxy-19-O-(4-methy1-6(E),8(E)-hexadecadienoyl)-16,18-dimethyl-10-ph enyl-[11]-cytochalasa-6(12),13(E)-diene- 1,21-dione. To our knowledge, 6 is the first member of the cytochalasin family to contain a long-chain fatty acid moiety. Compounds 1, 2, 3 and 6 showed immotility rates of 72%. 78%, 64% and 63%, respectively, in Artemia salina at 10ppm, while 4 and 5 showed no immotile activity. These findings strongly indicated that the hydroxyl group at C-7 and the exomethylene at C-6 is essential for such activity.
天然有機化合物討論会の論文
2006-09-15

P-32 インドネシア産キノコMicroporellus subsessilisに含まれる10-phenyl-[11]-cytochalasan(ポスター発表の部)

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