2. Academic Validation
  3. Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of Alangium salviifolium and Their Cytotoxicity

Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of Alangium salviifolium and Their Cytotoxicity

  • J Nat Prod. 2019 Sep 27;82(9):2645-2652. doi: 10.1021/acs.jnatprod.9b00670.
You-Sheng Cai 1,  Cong Wang 2,  Congkui Tian 3,  Wen-Ting Sun 1,  Ling Chen 1,  Di Xiao 1,  Si-Yuan Zhou 1,  Guofu Qiu 1,  Jianqing Yu 1,  Kongkai Zhu 4,  Sheng-Ping Yang 1
Affiliations

Affiliations

  • 1 Institute of TCM and Natural Products, School of Pharmaceutical Sciences , Wuhan University , Wuhan 430071 , People's Republic of China.
  • 2 Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Key Laboratory of Guangxi Colleges and Universities for Food Safety and Pharmaceutical Analytical Chemistry, School of Chemistry and Chemical Engineering , Guangxi University for Nationalities , Nanning 530006 , People's Republic of China.
  • 3 Wuling Mountain Institute of Natural Medicine , Hubei Minzu University, Key Laboratory of Biological Resources Protection and Utilization of Hubei Province , Enshi 445000 , People's Republic of China.
  • 4 School of Biological Science and Technology , University of Jinan , Jinan 250022 , People's Republic of China.
PMID: 31513408 DOI: 10.1021/acs.jnatprod.9b00670
Abstract

Two octahydro-protoberberine Alkaloids, alangiifoliumines A (1) and B (2), and two new protoemetine derivatives, alangiifoliumines C (3) and D (4), together with 11 known compounds, have been isolated from the stems of Alangium salviifolium. While the structures of these compounds were elucidated by spectroscopic methods, the absolute configurations of the new Alkaloids were determined by conformational analysis and time-dependent density functional theory-electronic circular dichroism spectra calculations on selected stereoisomers. Compounds 1 and 2 represent the first 5,8,8a,9,12,12a,13,13a-octahydro-protoberberine derivatives, in which the aromatic ring D was reduced to cyclohexene. All the compounds isolated were evaluated for their cytotoxic activity against three human Cancer cell lines: A-549, HeLa, and SKOV-3. Alkaloids 1, 3, and 6-14 exhibited inhibitory effects against all three human Cancer cell lines, with half-maximal inhibitory concentration (IC50) values in the range of 3 nM to 9.4 μM.

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