Three Unusual Sesquiterpenes with Distinctive Ring Skeletons from Daphne penicillata Uncovered by Molecular Networking Strategies.
Peng ZhaoZhi-Yuan LiShu-Yan QinBen-Song XinYu-Yang LiuBin LinGuo-Dong YaoXiao-Xiao HuangShao-Jiang SongPublished in: The Journal of organic chemistry (2021)
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 [5.3.2.01,6.04,11] 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.
Keyphrases
- lps induced
- inflammatory response
- high resolution
- molecular dynamics
- induced apoptosis
- lipopolysaccharide induced
- molecular docking
- cell cycle arrest
- density functional theory
- molecular dynamics simulations
- electron microscopy
- human health
- single molecule
- dual energy
- monte carlo
- spinal cord injury
- climate change
- cell death
- tissue engineering
- spinal cord
- neuropathic pain