期刊
JOURNAL OF NATURAL PRODUCTS
卷 82, 期 2, 页码 368-374出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.8b00930
关键词
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资金
- National Natural Science Foundation of China [81703411, U1606403, 41776156]
- Scientific and Technological Innovation Project - Qingdao National Laboratory for Marine Science and Technology [2016ASKJ08]
- Natural Science Foundation of the Jiangsu Higher Education Institutions of China [17KJA350005]
- Taishan Scholars Program, China
Cultivation of the mangrove rhizosphere soil-derived fungus Penicillium janthinellum HK1-6 with NaBr led to the isolation of two new brominated azaphilones, penicilones G and H (5, 6), two new tricyclic polyketides, penijanthinones A and B (7, 8), and two known azaphilones, penicilones A and B (1, 2). The planar structures and relative configurations of the new compounds were elucidated using comprehensive spectroscopic methods including 1D and 2D NOE spectra. Their absolute configurations were determined by chemical conversions, TDDFT ECD calculations, and comparisons of their ECD spectra. Interestingly, the NaBr-induced brominated azaphilones (5, 6) had the opposite configuration at C-7 compared to the chloro analogues (3, 4) produced by this fungus cultivated with sea salt. Ester hydrolysis of penicilone B (2) afforded the carboxylic acid side chain 2,4-dimethyldec-2-enoic acid (9), with a 4S configuration assigned by its specific rotation. Penicilone H (6) showed antibacterial activity with MIC values ranging from 3.13 to 12.5 mu g/mL.
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