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Salmycin A–D, Antibiotika aus Streptomyces violaceus , DSM 8286, mit Siderophor‐Aminoglycosid‐Struktur
Author(s) -
Vértesy László,
Aretz Werner,
Fehlhaber HansWolfram,
Kogler Herbert
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780105
Subject(s) - chemistry , stereochemistry , hydroxylamine , hydrolysis , ketone , nuclear magnetic resonance spectroscopy , organic chemistry
Salmycin A–D, Antibiotics from Strep tomy ces violaceus , DSM 8286, Having a Siderophor‐Aminoglycoside Structure 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 (C 41 H 70 FeN 7 O 21 ), 2 (C 41 H 69 FeN 6 O 21 ), 3 (C 40 H 67 FeN 6 O 21 ), and 4 (C 40 H 68 FeN 7 O 21 ) are classified as sideromycins and are stable when dry. Mild alkaline hydrolysis of 1 and 2 yielded the known siderophor danoxamin ( 5 ; C 27 H 46 FeN 5 O 11 ), and amino‐disaccharides. The amino‐glycoside 6 (C 14 H 25 NO 11 ) of salmycin B was stabilized by hydrogenation and the structure of the corresponding peracetate 10 determined by 1 H, 1 H‐ and 1 H, 13 C‐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, 13 C‐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.