Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Structures and Biological Properties of Kinamycin A, B, C, and D
大村 智中川 彰山田 陽城秦 藤樹古崎 昭雄渡辺 得之助
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1973 年 21 巻 5 号 p. 931-940

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A series of new antibiotics, Kinamycin A, B, C, and D which are mainly effective against gram-positive bacteria, were extracted with chloroform from the broth filtrate of Streptomyces murayamaensis sp. nov. HATA et OHTANI. Kinamycin C (I), C24H20O10N2, m/e 496 (M+), was determined to have an 8-hydroxynaphthoquinone skeleton, nitrile, acetoxyl, and tertiary methyl groups from its ultraviolet (UV), infrared (IR), and nuclear magnetic resonance (NMR) spectra, and was further found to have a unique structure of N-C-N from some chemical reactions and X-ray diffraction. Structure relationship among I and other components A, B, and D was assumed to be due to the difference in the number and position of the acetoxyl group from analyses of IR, NMR, and mass spectra of their acetylated compounds. The antimicrobial activity of the four kinamycins increases with the decreasing number of acetoxy group, in the order of kinamycin C, A, D, and B. In addition, some derivatives obtained during structural studies on I were found to have nearly equal or increased antimicrobia1 activity compared with I and kinamycin D (XI).
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© The Pharmaceutical Society of Japan
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