19 渦鞭毛藻の生産する抗カビ成分アンフィジノールの構造研究(口頭発表の部)

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Screening of seven species of marine dinoflagellates for antifungal substances led to discovery of highly potent gambieric acid in Gambierdiscus toxicus and amphidinol in Amphidinium klebsii. Amphidinol, which was three times more potent than amphotericin-B, was purified from cultured cells mainly by gel pearmeation chromatography. A part of the culture (20 L) was done with added NaH^<13>co_3. About 4% enrichment of ^<13>C was attained. UV and IR spectra, respectively, indicated the presence of a conjugated trien and a sulfate ester in the molecule. The latter moiety was further confimed by determination of SO_4^<2-> after solvolysis. FAB-MS indicated the molecular weight to be 1488 (C_<73>H_<125>O_<27>SNa). The major part of the structure was deduced by a combined use of 2D-NMR, such as ^1H-^1H COSY, ^1H-^1H HOHAHA, PS-NOESY and PS C-H COSY. Proton signals on a linear hydrocarbon chain with six double bonds (C54-C69) and a long carbon chain with three hydorxyls (C6-C17) were unassignable due to heavy overlapping and had to be solved by long range ^<13>C-^1H COSY and ^<13>C-^1H HOHAHA. With the ^<13>C-enriched preparation, measurements were successful with only 3 mg. As the ^<13>C signals in the repeating moieties were too congested to be correlated with ^1H signals, these ^<13>C observing methods were more informative to establish these parts of the sturcutre than were ^1H observing methods (HMQC, HMBC). Detailed analyses of ^<13>C-^1H 2D-NMR data thus enabled us to deduce the whole structure of amphidinol as shown in Fig. 3.
天然有機化合物討論会の論文
1990-09-25

19 渦鞭毛藻の生産する抗カビ成分アンフィジノールの構造研究(口頭発表の部)

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