Gastroprotective 2-(2-phenylethyl)chromone-sesquiterpene hybrids from the resinous wood of Aquilaria sinensis (Lour.) Gilg

[Display omitted] •Six rare 2-(2-phenylethyl)chromone-sesquiterpene hybrids were isolated from Chinese agarwood.•Compounds 2 and 6 exhibited pronounced protection against TCA-induced gastric mucosal damage.•Compound 6 suppressed the ER stress-triggered apoptosis in TCA-insult cells via Perk/eIF2α/CH...

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Published in:Bioorganic chemistry 2023-04, Vol.133, p.106396-106396, Article 106396
Main Authors: Zhang, Hang, Ma, Jia-Le, Chang, Chuang, Ta, He, Zhao, Yun-Fang, Shi, She-Po, Song, Yue-Lin, Tu, Peng-Fei, Huo, Hui-Xia, Zheng, Jiao, Li, Jun
Format: Article
Language:English
Subjects:
2-(2-Phenylethyl)chromone-sesquiterpene hybrid
Aquilaria sinensis
Aquisinenin
Chinese agarwood
Chromones
Flavonoids - chemistry
Gastric mucosal protection
Molecular Structure
Resins, Plant
Sesquiterpenes
Thymelaeaceae - chemistry
Wood - chemistry
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Summary:[Display omitted] •Six rare 2-(2-phenylethyl)chromone-sesquiterpene hybrids were isolated from Chinese agarwood.•Compounds 2 and 6 exhibited pronounced protection against TCA-induced gastric mucosal damage.•Compound 6 suppressed the ER stress-triggered apoptosis in TCA-insult cells via Perk/eIF2α/CHOP signal pathway. Six previously unprecedented 2-(2-phenylethyl)chromone-sesquiterpene hybrids, aquisinenins A–F (1 – 6), were isolated from the resinous wood of Aquilaria sinensis by a LC-MS-guided fractionation procedure. Their structures were determined by extensive spectroscopic analysis (1D and 2D NMR, UV, IR, and HRMS) and experimental and computed ECD data. Compounds 1 – 6 were rare dimeric 2-(2-phenylethyl)chromone-sesquiterpene derivatives featuring 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone hybridized with different sesquiterpene (eudesmane/guaiane type) moieties via ester bond. Furthermore, all the isolated compounds were evaluated for their protective effects on taurocholic acid (TCA)-induced GES-1 cell injury. The most effective aquisinenin F (6) was used to elucidate the involved mechanism on protection against TCA-induced gastric mucosal damage. Our results indicated that 6 protected against gastric mucosal cell insult by downregulation of the ER stress triggered by TCA.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2023.106396