Julichrome Monomers from Marine Gastropod Mollusk-Associated Streptomyces and Stereochemical Revision of Julichromes Q3 ·5 and Q3·3.

Julichrome Monomers from Marine Gastropod Mollusk-Associated Streptomyces and Stereochemical Revision of Julichromes Q3·5 and Q3·3. Chem Biodivers. 2020 Feb 24;: Authors: Dong Y, Ding W, Sun C, Ji X, Ling C, Zhou Z, Chen Z, Chen X, Ju J Abstract Two julichrome monomers, julichromes Q 11 ( 1 ) and Q 12 ( 2 ), along with five known julichromes [Q 10 ( 3 ), Q 3.5 ( 4 ), Q 3·3 ( 5 ), Q 6·6 ( 6 ), Q 6 ( 7 )] and four known anthraquinones [chrysophanol ( 8 ), 4-acetylchrysophanol ( 9 ), islandicin ( 10 ), huanglongmycin A ( 11 )], were isolated from the marine gastropod mollusk Batillaria zonalis- associated Streptomyces sampsonii SCSIO 054. This is the first report of julichromes isolated from a marine source. Extensive dissection of 1D and 2D NMR datasets combined with X-ray crystallography enabled rigorous elucidation of the previously reported configurations of julichrome Q 3·5 ( 4 ) and related julichrome Q 3·3 ( 5 ); both of the stereochemistry at C(9) needs to be revised. In addition, julichrome Q 12 ( 2 ) was found to display antibacterial activity against Micrococcus luteus and Bacillus subtilis with MICs of 2.0 and 8.0 μg mL -1 ; compounds 1 , 3 , 6 and 7 also showed inhibitory activities against an array of methicillin-resistant Staphylococcus aureus , S. aureus and S . simulans AKA1 with MIC values ranging from 8 to 64 μg mL -1. PMID: 32091654 [PubMed - as supplied by publisher]
Source: Chemistry and Biodiversity - Category: Biochemistry Authors: Tags: Chem Biodivers Source Type: research