期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 9, 页码 5091-5098出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00030
关键词
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资金
- National Key Research and Development Program of China [2018YFC0310903]
- Drug Innovation Major Project [2018ZX09711-001-001-009]
- National Natural Science Foundation of China [81520108028, 21672230, 41876194, 41506187, 81603022]
- NSFC-Shandong Joint Fund for Marine Science Research Centers [U1606403]
- SKLDR/SIMM Projects [SIMM1903ZZ-04]
- Syngenta-SIMM-PhD Studentship Project
A detailed chemical research of soft coral Sarcophyton ehrenbergi from the South China Sea yielded five new cembranoids 1-5 featuring an alpha,beta-unsaturated-gamma-lactone moiety rarely at C-6 to C-19, along with one known related diterpene 6. The structures and absolute configurations of 1-5 were established in the light of extensive spectroscopic data analysis, chemical reaction, X-ray diffraction analysis, TDDFT/ECD (time-dependent density functional theory/electronic circular dichroism) calculations, and biosynthesis path. This study led to the stereostructural revision of 6, which was misassigned by erroneously applying the empirical ECD helicity rule, indicating a challenging and risky work to determine the structure of this type of marine cembranoids. In the TNF-alpha inhibitory biotest, compound 2 exhibited a potent inhibitory activity (IC50 = 8.5 mu M), which was analogous to the positive control dexamethasone (IC50 = 8.7 mu M).
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