39 海洋動物タツナミガイDolabella auriculariaから得られた抗腫瘍性物質Dolastatin 11の構造(口頭発表の部)

概要

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A cyclic depsipeptide dolastatin 11 (1) was isolated as the major antineo-plastic component of the sea hare Dolabella auricularia, collected in the Indian Ocean. Dolastatin 11 has shown antineoplastic activity against the PS leukemia, ED_<50> 2.7×10^<-3>μg/ml. Detailed studies on the 400MHz 'H-'H-COSY, 2D-J resolved, 'H-^<13>C 2D-shift correlated and 'H NOESEY experiments combined with 'H NOE difference NMR and SP-SIMS experiments, (in addition to acid and base hydrolysis studies, followed by GC-MS analysis) were employed to elucidate the structure of dolastatin 11 (1). Interestingly, structure (1) was close to that of Majusculamide C, which was isolated from the blue-green algae Lyngbya majuscula and structure determined by R. Moore and colleagues in 1984. The difference resided in replacement of a N-methylisoleucine unit in Majusculamide C with a N-methylleucine in dolastatin 11 (1). In order to confirm the proposed pentapeptide portion of structure (1), the synthesis of the segment Gly-NMe-L-Leu-Gly-NMe-L-Val-OMe-NMe-L-Tyr-OMe (8) was completed. The synthetic pentapeptide (8) was useful in confirming the dolastatin 11 structural determination.
天然有機化合物討論会の論文
1987-07-25