期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 21, 页码 15298-15306出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01880
关键词
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资金
- National Natural Science Foundation of China [82073736, 81872766]
- Key R&D Projects in Liaoning Province [2020JH2/10300058]
- Liaoning revitalization talents program [XLYC2002066, XLYC2007180]
- Program for Major Scientific and Medical Technology Problems of China Medicine Education Association in 2020 [2020KTS003]
Through molecular networking strategies, four unusual sesquiterpenes were isolated from the herb of Daphne penicillata, including Daphnenoids A-C and a biogenetically related Daphnenoid D. Daphnenoid A has a unique caged structure, while Daphnenoids B and C are the first natural sesquiterpenes with spirocyclic systems.
Daphnenoids A-C (1-3), three unusual sesquiterpenes with distinctive ring skeletons, together with a biogenetically related daphnenoid D (4) were obtained from the herb of Daphne penicillata by molecular networking strategies. Daphnenoid A (1) possesses a unique caged tetracyclo [5.3.2.0(1),(6).0(4),(11)] dodecane scaffold by unexpected cyclizations of C-1/C-11 and C-2/C-14. Daphnenoids B and C (2 and 3) were the first discovered natural sesquiterpenes with unique 5/5 spirocyclic systems in nature. Their structures were determined by NMR spectroscopic analysis, computer-assisted structure elucidation methods, quantum chemical calculations, and X-ray diffraction. A hypothetical biogenetic pathway begins with typical guaiane sesquiterpene (a), including a key intermediate (4) was proposed. Daphnenoids B and C (2 and 3) exhibited potential inhibitory activities on the production of NO against LPS-induced BV2 microglial cells.
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