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氢化庚烯素:一种水溶性多烯大环内酯。II. 化学和生物学性质。

Hydroheptin: a water-soluble polyene macrolide. II. Chemical and biological properties.

作者信息

Tunac J B, McDaniel L E, Patel M, Schaffner C P

出版信息

J Antibiot (Tokyo). 1979 Dec;32(12):1230-8. doi: 10.7164/antibiotics.32.1230.

DOI:10.7164/antibiotics.32.1230
PMID:541250
Abstract

Hydroheptin, a new polyene macrolide antifungal antibiotic, is co-produced with the antibiotic, chartreusin, by a strain of Streptomyces chartreusis designated as IMRU 3962 isolated in our laboratory. The unique water-solubility of this antibiotic at neutrality, revealing in aqueous solution molecular dispersion and an ultraviolet-visible absorption spectrum characteristic of an all-trans heptaene chromophore, clearly distinguishes it from all previously-described and naturally-occurring heptaene macrolides. The isolation and identification of the amino sugar, mycosamine (3-amino-3,6-dideoxy-D-mannose), in acid hydrolysates of hydroheptin and the absence of an aromatic amine upon retrograde alkaline dealdolization of the molecule certainly characterize the antibiotic as a member of the non-aromatic heptaene macrolide group. Chromatographic and countercurrent distribution studies likewise support its novelty. With little or no demonstrable activity against bacteria, hydroheptin as compared to other non-aromatic heptaene macrolides exhibits excellent but somewhat less activity against a wide variety of yeasts and fungi. Likewise, its parenteral toxicity appears to be less than that of other heptaene macrolides.

摘要

水合菌素是一种新型多烯大环内酯类抗真菌抗生素,由我们实验室分离出的一株名为IMRU 3962的绿脓链霉菌与抗生素黄绿青霉素共同产生。这种抗生素在中性条件下具有独特的水溶性,在水溶液中呈现分子分散状态,其紫外可见吸收光谱具有全反式七烯发色团的特征,这使其与所有先前描述的天然七烯大环内酯类抗生素明显不同。在水合菌素的酸水解产物中分离并鉴定出氨基糖——霉菌胺(3 - 氨基 - 3,6 - 二脱氧 - D - 甘露糖),并且该分子经逆向碱性脱醛醇反应后不存在芳香胺,这些特征无疑将该抗生素归为非芳香族七烯大环内酯类。色谱和逆流分配研究同样证实了它的新颖性。水合菌素对细菌几乎没有或没有明显活性,与其他非芳香族七烯大环内酯类相比,它对多种酵母和真菌具有优异但略低的活性。同样,其肠胃外毒性似乎低于其他七烯大环内酯类。

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