51 新抗腫瘍性抗生物質Macbecin I及びIIの構造

概要

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Macbecin I (1) and II (2) are new antitumor antibiotics which have been isolated from the culture broth of Nocardia sp. No. C-14919. Macbecin I (1), C_<30>H_<42>N_2O_8 and Macbecin II (2), C_<30>H_<44>N_2O_8 were considered to be 2,6-disubstituted benzoquinone and hydroquinone from oxidation-reduction relationship, UV, ^1H-NMR and ^<13>C-NMR spectra. Alkaline methanolysis of 1 gave a 2-aminobenzoquinone derivative (5), suggesting an ansa-structure for 1, and acid hydrolysis of 1 gave decarbamoyl products (9), (10) and (11). Spin decoupling studies of 1, 3 and 5 clarified the presence of partial structures [A], [B], [C] and [D]. Furthermore, from their interrelationship were proposed two structures 1a and 1b, out of which 1a has been selected for the structure of 1 on the basis of the structure of oxidative degradation product (12). X-ray analysis of the bromoacetyl derivative of 1 confirmed the above proposed structure and in addition determined the absolute stereochemistry of 1 and 2.
天然有機化合物討論会の論文
1979-09-20