期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 3, 页码 1228-1237出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02614
关键词
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资金
- Program of National Natural Science Foundation of China [81874300, U1706210, 41776141, U1606403]
- AoShan Talents Program - Qingdao National Laboratory for Marine Science and Technology [2015ASTP-ES11]
- Program of Natural Science Foundation of Shandong Province of China [JQ201510]
- Fundamental Research Funds for the Central Universities [201841004]
- Taishan Scholars Program, China
- China Postdoctoral Science Foundation [2017M622285]
- Qingdao Postdoctoral Researcher Applied Research Project, China
A challenging problem in natural product discovery is to rapidly dereplicate known compounds and expose novel ones from complicated components. Herein, integrating the LC-MS/MS-dependent molecular networking and H-1 NMR techniques efficiently and successfully enabled the targeted identification of seven new cyclohexadepsipeptides, chrysogeamides A-G (1-7), from the coral-derived fungus Penicillium chrysogenum (CHNSCLM-0003) which was targeted from a library of marine-derived Penicillium fungi. Compound 4 features a rare 3-hydroxy-4-methylhexanoic acid (HMHA) moiety which was first discovered from marine-derived organisms. Interestingly, isotope-labeling feeding experiments confirmed that C-13(1)-L-Leu was transformed into C-13(1)-D-Leu moiety, indicating that D-Leu could be isomerized from L-Leu. Compounds 1 and 2 obviously promoted angiogenesis in zebrafish at 1.0 mu g/mL with nontoxic to embryonic zebrafish at 100 mu g/mL. Combining molecular networking with H-1 NMR as a discovery tool will be implemented as a systematic strategy, not only for known compounds dereplication but also for untapped reservoir discovery.
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