Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

Guaiane-type sesquiterpenoids are well-known in medicinal chemistry of natural products, but the unprecedented sesquiterpenoid scaffold furnished by unexpected carbon–carbon linkage formation or cleavage deserves to be further explored. Herein, we report on targeted isolation of such compounds from...

Full description

Saved in:
Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-09, Vol.10 (19), p.4740-4749
Main Authors: Shu-Hui, Dong, Jin-Ling, Han, Xin-Yu, Chang, Mei-Ya Lian, Zhang, Xin, Xiao-Ling, Liu, Bai, Ming, Xiao-Xiao, Huang, Shao-Jiang, Song
Format: Article
Language:English
Subjects:
Carbon
Cholinesterase
Ischemia
Natural products
NMR
Nuclear magnetic resonance
Organic chemistry
Quantum chemistry
Screening
Sesquiterpenes
Sesquiterpenoids
X-ray diffraction
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Guaiane-type sesquiterpenoids are well-known in medicinal chemistry of natural products, but the unprecedented sesquiterpenoid scaffold furnished by unexpected carbon–carbon linkage formation or cleavage deserves to be further explored. Herein, we report on targeted isolation of such compounds from Daphne aurantiaca, daphaulides A, B, and D (1, 2, and 4), by our integrated strategy: the Block and Grid strategy (BAGs) followed by activity screening and structure evaluation. Their structures were elucidated by NMR spectroscopic analysis, computer-assisted structure elucidation methods, quantum chemical calculations, and X-ray diffraction. The plausible biosynthetic pathways for compounds 1–5 were proposed. Compounds 2 and 3 exhibited dose-dependent inhibitory effects against cholinesterase in vitro and in silico. The experimental and theoretical results indicated that compound 3 opens up new possibilities for developing anti-cerebral ischemia agents.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo00902e