7 海藻から分離した真菌が生産する新規抗微細藻物質ハリメシン類(口頭発表の部)

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In the course of searching new substances produced by marine-microorganism, three anti-microalgal substances named halymecins A(1), B(2), C(3) were isolated from the fungus, Fusarium sp. FE-71-1 of an alga isolate, by centrifuged partition chromatography and column chromatography. The molecular formula of 1 was determined to be C_<42>H_<76>O_<14> on the basis of HR FAB-MS. The ^1H and ^<13>C NMR showed the molecule contained one acetyl group, four methyl groups, 16 methylene groups, 8 methine groups bound to oxygen and four carbonyl carbons besides acetyl carbon. The acetyl derivative of 1 simplified ^1H-NMR spectrum, suggested that 1 was the tetramer of single unit and this unit was elucidated to 3,5-dihydroxydecanoate by extensive analyses of COSY and TOCSY spectra. The position of the acetyl group of 1 was determined by HMBC spectra. Acid degradation of 1 afforded an optical active 3-hydroxy-δ-lactone, coincided with the reported 3R,5R stereo-isomers unambiguously by NMR and optical rotation. The structure of 2 was elucidated to a β-D-mannoside of 1 from the spectral analysis of NMR and chemical degradation. 3 was also elucidated to mono acetyl derivative of 3,5-dihydroxydecanoate trimmer as a same manner. We also found the anti-microalgal fraction from another fungus, Acremonium sp. FK-N30 of an alga isolate. NMR spectral features were similar to those observed for 1, 2 and 3 but without having acetyl group. This fraction showed a single peak by HPLC however it was proved to be the mixture of halymecin D (4) and E (5) by negative FAB-MS. 4 had a molecular formular of C_<40>H_<74>O_<15> by HR FAB-MS suggested the existence of trihydroxydecanoate units as well as 3,5-dihydroxydecanoate. Negative FAB CID revealed that 4 was composed of two dihydroxydecanoate and two trihydroxydecanoate and the sequence was explained by fragmentation brought by cleavage of each ester bond. The hydroxy groups of trihydroxydecanoate moieties were elucidated to 3, 5, 9 positions by COSY spectrum. A molecular formular of C_<30>H_<56>O_<11> was established for 5. The structure was elucidated to be composed of two 3,5-dihydroxydecanoate and one 3,5,9-trihydroxydecanoate The sequence was explained by negative FAB CID.
天然有機化合物討論会の論文
1994-09-20

7 海藻から分離した真菌が生産する新規抗微細藻物質ハリメシン類(口頭発表の部)

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