Undescribed indole lactones from Alstonia scholaris protecting hepatic cell damage

Six previously undescribed rigidly monoterpenoid indole alkaloids, alstolactines F-K (1-6), were isolated from Alstonia scholaris. Among them, a pair of cage-like epimers, 1 and 2, featuring a rare 6/5/6/6/7 ring system, represent the first example of C →C -olide, while compound 3 possesses unique d...

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Published in:Phytochemistry (Oxford) 2024-01, Vol.217, p.113926-113926, Article 113926
Main Authors: Hu, Bin-Yuan, Zhao, Yun-Li, He, Ying-Jie, Qin, Yan, Luo, Xiao-Dong
Format: Article
Language:English
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Summary:Six previously undescribed rigidly monoterpenoid indole alkaloids, alstolactines F-K (1-6), were isolated from Alstonia scholaris. Among them, a pair of cage-like epimers, 1 and 2, featuring a rare 6/5/6/6/7 ring system, represent the first example of C →C -olide, while compound 3 possesses unique degraded C and C . The structures of the isolates were established by multiple spectroscopic analyses, quantum computational chemistry methods, and X-ray diffraction. Furthermore, the expression levels of proteins including NLRP3, TLR4, P-p65, NF-ĸB, Notch-2, IL-18, P-p38, and p38 in LPS-induced human normal hepatocyte (LO2) cells could be significantly downregulated by compounds 1-6, which showed potent anti-inflammatory bioactivity.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2023.113926