SALMYCIN A-D, ANTIBIOTICS FROM STREPTOMYCES-VIOLACEUS, DSM-8286, HAVING A SIDEROPHORE AMINOGLYCOSIDE STRUCTURE
SALMYCIN A-D, ANTIBIOTICS FROM STREPTOMYCES-VIOLACEUS, DSM-8286, HAVING A SIDEROPHORE AMINOGLYCOSIDE STRUCTURE
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DOI：
10.1002/hlca.19950780105
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发表时间：
1995-01-01
影响因子：
1.8
通讯作者：
KOGLER, H
中科院分区：
文献类型：
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作者：
VERTESY, L;ARETZ, W;KOGLER, H
盐霉素B（2）和C（3）是在酸性条件下从紫色链霉菌DSM 8286的培养液中分离出来的，在酸性条件下它们是稳定的。酸和碱不稳定的天然主要组分盐霉素A（1）以及盐霉素D（4）在严格中性pH条件下获得。化合物1（C41 H69 FeN 6 O21）、2（C41 H69 FeN 6 O21）、3（C40 H67 FeN 6 O21）和4（C40 H68 FeN 7 O21）被分类为铁霉素，干燥时稳定。1和2的温和碱性水解产生已知的含铁载体丹沙明（5; C27 H46 FeN 5 O 11）和氨基二糖。通过氢化使盐霉素B的氨基糖苷6（C14 H25 NO11）稳定，并通过H-1、H-1-和（HC）-H-1-C-13-相关NMR光谱测定相应的过乙酸酯10的结构（表1）。化合物6由连接至6-脱氧-6-（甲基氨基）庚吡喃糖的2-位的葡萄糖-2-酮糖单元组成。达诺沙明通过羧基通过酯键与葡萄糖-2-酮糖的伯醇键合。盐霉素A（1）是2的天然肟，由2与羟胺反应合成。鲑鱼霉素和含有六吡喃-2-酮糖的那些衍生物形成稳定的酮水合物，其可以通过质谱法鉴定。虽然最近发现的几个特征的丹霉素不对应的salmycins，C-13-NMR光谱表明，这两组抗生素是密切相关的。所有沙门氏菌素，尤其是组分1，对葡萄球菌和链球菌，甚至对这些病原体的耐药菌株都具有高度活性。
Salmycin B (2) and C (3) were isolated under acid conditions, under which they are stable, from the culture broth of Streptomyces violaceus, DSM 8286. The acid- and alkaline-labile, native main component salmycin A (1), as well as salmycin D (4), were obtained under strictly neutral pH conditions. The compounds 1 (C41H70FeN7O21), 2 (C41H69FeN6O21), 3 (C40H67FeN6O21), and 4 (C40H68FeN7O21) are classified as sideromycins and are stable when dry. Mild alkaline hydrolysis of 1 and 2 yielded the known siderophor danoxamin (5; C27H46FeN5O11), and amino-disaccharides. The amino-glycoside 6 (C14H25NO11) of salmycin B was stabilized by hydrogenation and the structure of the corresponding peracetate 10 determined by H-1,H-1- and (HC)-H-1-C-13-correlation NMR spectroscopy (Table 1). Compound 6 consists of a glucos-2-ulose unit which is linked to the 2-position of a 6-deoxy-6-(methylamino)heptopyranose. The danoxamin is bonded via the carboxy group by ester linkage to the primary alcohol of the glucos-2-ulose. Salmycin A (1) is a natural oxime of 2, it was synthesized from 2 with hydroxylamine. The salmycins and those derivatives which contain hexapyranos-2-ulose form stable ketone hydrates which can be identified by mass spectrometry. Although several recently identified features of the danomycins do not correspond with those of the salmycins, C-13-NMR spectra show that both groups of antibiotics are closely related. All salmycins, especially component 1, are highly active against Staphylococci and Streptococci, even against resistant strains of these pathogens.