Marine Science & Technology Institute, College of Environmental Science & Engineering , Yangzhou University , 196#, Huayang West Street , Yangzhou 225127 , People's Republic of China.
Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy , Ocean University of China , Qingdao 266003 , People's Republic of China.
J Nat Prod. 2019 Feb 22;82(2):368-374. doi: 10.1021/acs.jnatprod.8b00930. Epub 2019 Jan 29.
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 4 S configuration assigned by its specific rotation. Penicilone H (6) showed antibacterial activity with MIC values ranging from 3.13 to 12.5 μg/mL.
用 NaBr 培养红树林根际土壤来源的真菌青霉（Penicillium janthinellum）HK1-6 导致分离得到两个新的溴化氮杂菲酮，penicilones G 和 H（5、6），两个新的三环聚酮，penijanthinones A 和 B（7、8），以及两个已知的氮杂菲酮，penicilones A 和 B（1、2）。新化合物的平面结构和相对构型通过包括 1D 和 2D NOE 光谱在内的综合光谱方法阐明。它们的绝对构型通过化学转化、TDDFT ECD 计算和比较它们的 ECD 光谱确定。有趣的是，与由这种真菌在海水中培养产生的氯类似物（3、4）相比，NaBr 诱导的溴化氮杂菲酮（5、6）在 C-7 处具有相反的构型。penicilone B（2）的酯水解得到羧酸侧链 2,4-二甲基癸-2-烯酸（9），其旋光度确定为 4S 构型。Penicilone H（6）显示出抗菌活性，MIC 值范围为 3.13 至 12.5 μg/mL。
