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Maremycins C and D, New Diketopiperazines, and Maremycins E and F, Novel Polycyclic spiro ‐Indole Metabolites Isolated from Streptomyces sp.
Author(s) -
Tang YuanQing,
Sattler Isabel,
Thiericke Ralf,
Grabley Susanne,
Feng XiaoZhang
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:2<261::aid-ejoc261>3.0.co;2-6
Subject(s) - diketopiperazines , moiety , chemistry , diastereomer , stereochemistry , indole test
New diketopiperazines, named maremycins C 1 /C 2 ( 1a / 1b ) and D 1 /D 2 ( 2a / 2b ), as well as the novel spiro‐indoles, maremycins E ( 3 ) and F ( 4 ), have been detected alongside the known maremycin B ( 6 ) in the culture broth of Streptomyces sp . (strain GT 051237) by chemical screening. The structures have been determined by detailed NMR spectroscopic investigations of the isolated metabolites. Maremycins C 1 /C 2 ( 1a / 1b ) as well as D 1 /D 2 ( 2a / 2b ) are diastereomers and were identified as mixtures. Structurally, maremycins C 1 /C 2 ( 1a / 1b ) are the diastereomers of the sulfur oxidation products of maremycin B ( 6 ), while D 1 /D 2 ( 2a / 2b ) are the demethylmercapto analogues of maremycins A ( 5 ) and B ( 6 ), respectively. Maremycins E and F possess a novel structural skeleton, where a spiro moiety is formed between the 6‐position of the cyclopenta[ f ]quinoxaline moiety and the 3′‐position of the indol‐2‐one moiety of the initial diketopiperazine product.