Monoterpene indole alkaloids with diverse skeletons from the stems of Rauvolfia vomitoria and their acetylcholinesterase inhibitory activities
| Autor: | Rongkun Miao, Xincai Hao, Guanqun Zhan, Fuxin Zhang, Zengjun Guo, Xi Zheng, Hui Zhang, Xinxin Zhang |
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| Rok vydání: | 2020 |
| Předmět: |
0106 biological sciences
endocrine system Aché Monoterpene Plant Science Horticulture complex mixtures 01 natural sciences Biochemistry Rauwolfia Indole Alkaloids chemistry.chemical_compound heterocyclic compounds Cytotoxicity Molecular Biology Indole test biology Apocynaceae Molecular Structure 010405 organic chemistry organic chemicals Alkaloid Rauvolfia vomitoria General Medicine biology.organism_classification Acetylcholinesterase language.human_language 0104 chemical sciences chemistry language Monoterpenes Cholinesterase Inhibitors 010606 plant biology & botany |
| Zdroj: | Phytochemistry. 177 |
| ISSN: | 1873-3700 |
| Popis: | Nine undescribed monoterpene indole alkaloids, rauvomitorine A−I, including an unprecedented C-9-methoxymethylene-sarpagine framework alkaloid, two rare suaveoline framework type alkaloids, and six yohimbine framework type alkaloids, as well as eleven known alkaloids, were isolated from the stems of Rauvolfia vomitoria Afzel. (Apocynaceae). The structures of the unreported alkaloids were elucidated by extensive spectroscopic analysis and single-crystal X-ray diffraction analysis with Cu Kα radiation. Rauvomitorine A with an unreported framework type represents the first example of C-9-methoxymethylene-sarpagine alkaloids and its plausible biosynthetic pathway was proposed. All the isolated alkaloids were evaluated their acetylcholinesterase inhibitory (AChE) activities and cytotoxicity against five cancer cell lines and some of them exhibited potential anti-AChE activities with IC50 values ranging from 49.76 to 186.62 μM. Importantly, this is the first report of the AChE inhibitory activities on suaveoline framework type alkaloids, suggesting this type of alkaloids may be valuable sources for the discovery of AChE inhibitory agents. A preliminary structure-activity relationship for AChE inhibitory activities of the isolated alkaloids is also discussed, providing some clues to designing lead compounds for AChE inhibitors. |
| Databáze: | OpenAIRE |
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