9 フロリダ産コケムシAmathia convolutaより得られた新規N-acyl γ-lactam alkaloids,Convolutamides A〜Fおよびβ-phenylethylamines,Convolutamines A〜Eの構造(口頭発表の部)

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During our search for new bioactive substances from marine organisms, we have examined extracts of the Floridian bryozoan Amathia convoluta and obtained the six new alkaloids, convolutamides A (1a), B (1b), C (2a), D (2b), E (3a), and F (3b), possessing an N-acyl-γ-lactam moiety with a dibromophenol group. Also, from the same extracts, the five new β-phenylethylamine alkaloids, convolutamines A (4), B (5), C (6), D (7), and E (8) were obtained. The structures have been elucidated on the basis of extensive spectroscopic data such as ^1H-^1H COSY, HMQC, HMBC, NOESY, HMQC-HOHAHA, INADEQUATE experiments. The structures of convolutamides A〜F were shown in Fig. 1. The NMR data of convolutamides A (1a) and B (1b) were shown in Table 1. The partial structure of the γ-lactam moiety was deduced from the COSY correlations as well as the HMBC cross-peaks, in addition to FAB MS/MS spectral data (Table 2). In Fig. 2, the daughter ions observed in the negative FAB MS/MS for the acyl part of 1b and 2b were illustrated. On the other hand, the structures of convolutamines A〜E were shown in Fig. 3. The ^1H and ^<13>C NMR data were indicated in Table 3 and 4. The relative stereochemistry of the morpholine ring in the structure of convolutamine E (8) was illustrated in Fig. 4. To our knowledge, compounds with oxazolidine as convolutamine D (7) are rare in nature. While, convolutamides A〜F (1a〜3b) may belong to an unprecedented class of natural product possessing a unique γ-lactam and dibromophenol ring system. Convolutamides A (1a) and B (1b) exhibited against L1210 and KB cells with IC50 values of 4.8 and 2.8μg/ml, respectively. Also, convolutamines A (1), B (2), and D (4) exhibited against P388 cell with IC50 values of 10.6, 4.8, and 8.6μg/ml, respectively.
天然有機化合物討論会の論文
1994-09-20

9 フロリダ産コケムシAmathia convolutaより得られた新規N-acyl γ-lactam alkaloids,Convolutamides A〜Fおよびβ-phenylethylamines,Convolutamines A〜Eの構造(口頭発表の部)

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