Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Structure of a New Antimicrobial Unsaturated Fatty Acid from Sm. kitasatoensis NU-23-1
大村 智今井 美光竹嶋 秀雄中川 彰
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1976 年 24 巻 12 号 p. 3139-3143

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Antimicrobial compound LA-1 (I) has been isolated from the culture broth of the leucomycin (LM) producing strain, Sm. kitasatoensis NU-23-1 and its structure determined. It has been found that the new compound I is transiently accumulated preceding the production of LM during fermentation process. I is extracted with organic solvents under acidic conditions from the culture filtrate of its highly accumulative mutant NU-4-4-2 after 27-30 hours incubation. I is exceedingly unstable in its solid state. Its ultraviolet (UV) spectrum (UV λMeOHmax nm : 270) and infrared (IR) spectrum (IR νCCl4max cm-1 : 3000-, 1925, 1700-, 1630-1610, 985) have suggested that I is an oxo-unsaturated fatty acid having a conjugated allene segment. Its proton magnetic resonance (PMR) and 13Carbon-nuclear magnetic resonance (CMR) spectra and the spectroscopic data (IR, PMR, CMR, and mass spectrum) of its stable derivatives, octahydro LA-1 (II) and octahydro methyl LA-1 (III), have been fully compatible with the molecular formula, C10H10O3 and with the molecular weight, 178. Its structure has been elucidated on the basis of these spectroscopic properties.
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© The Pharmaceutical Society of Japan
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