92(PB3-3) 新規Glycopeptide系抗生物質Orienticin類の構造(ポスター発表の部)

概要

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Glycopeptide antibiotics have been attracting interest because of their activity against methicillin-resistant Staphylococcus aureus, and many new glycopeptides have been reported up to date. We isolated the new glycopeptide antibiotics orienticin A (1), B (2), C (3) and D (4) from metabolites of Nocardia orientalis PA 42867 by repeated reversed-phase chromatography. The structure of orienticine A (1), the major component, was elucidated by comparison of ^1H and ^<13>C NMR spectra with those of vancomycin (5). The absolute structure of orienticin A (1) was decided by comparison of the aglycone (8) with the partial hydrogenated vancomycin aglycone. The structure of orienticin B (2), the second major component, was also elucidated by comparison of its NMR spectrum with that of orienticin A (1), and the partial hydrolysis product was also obtained, i.e., pseudo-aglycone I (6). The minor component orienticin C (3) was found to be dechlorinated orienticin A (1), and orienticin D (4) to be orienticin A (1) methylated at the N-methyl leucine part, based on the NMR and mass spectra. These four new glycopeptide antibiotics, orienticin A (1), B (2), C (3), D (4), and their acid-treated products, i.e., pseudo-aglycone I (6), II (7) and aglycone (8), possess in vitro and in vivo antibacterial activities, and some of them are more active than vancomyicn (5).
天然有機化合物討論会の論文
1987-07-25