Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q3 ⋅ 5 and Q3 ⋅ 3. Issue 4 (12th March 2020)

• Record Type: Journal Article
• Authors: Dong, Yuliang; Ding, Wenjuan; Sun, Changli; Ji, Xiaoqi; Ling, Chunyao; Zhou, Zhenbin; Chen, Zhiyun; Chen, Xuehong; Ju, Jianhua
• Is Part Of: Chemistry & biodiversity. Volume 17:Issue 4(2020)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-03-12
• Subjects: julichromes -- absolute configuration -- structure revision -- antibacterial activity -- biological activity; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.202000057
• Languages: English
• ISSNs: 1612-1872

Abstract

Abstract: Two julichrome monomers, julichromes Q11 (1 ) and Q12 (2 ), along with five known julichromes (Q10, Q3 ⋅ 5, Q3 ⋅ 3, Q6 ⋅ 6, Q6, 3 –7 ) and four known anthraquinones (chrysophanol, 4‐acetylchrysophanol, islandicin, huanglongmycin A, 8 –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 Q3 ⋅ 5 (4 ) and related julichrome Q3 ⋅ 3 (5 ); both of the configuration at C(9) needs to be revised. In addition, julichrome Q12 (2 ) was found to display antibacterial activity against Micrococcus luteus and Bacillus subtilis with MICs of 2.0 and 8.0 μg mL −1 ; four compounds (1, 3, 6, 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 . Abstract :