Cytotoxic alkaloids from the fruits and seeds of Alangium salviifolium (L.f.) Wangerin

Zhou, Siyuan; Fan, Fengkai; Sun, Jian; Guo, Ziyan; Sun, Wen-Ting; Chen, Ling; Tang, Qing-Qing; Qiu, Guofu; Yang, Sheng‐Ping; Yu, Jianqing; Cai, Yuanfeng

doi:10.1016/j.phytol.2018.06.012

Cited by 9 publications

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References 13 publications

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“…At this point, all the carbon, hydrogen, and nitrogen atoms had been accounted for, except for a single oxygen atom that remained unassigned. A detailed analysis of the NMR data (Table ) of 3 and 8 implied that this unassigned oxygen atom should be attached to the nitrogen atom of the imine group, which was confirmed by the shielded chemical shift of C-11 (δ C 136.8). ,, The planar structure of 3 was determined unambiguously as shown. The relative configuration of 3 was established by an analysis of the NOESY spectrum.…”

Section: Results and Discussionmentioning

confidence: 99%

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

et al. 2019

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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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Section: Results and Discussionmentioning

confidence: 99%

“…Recently, our group described the isolation of cepheline-type alkaloids from the fruits and seeds of Alangium salviifolium (L.f.) Wangerin and their cytotoxic activities . In a continuation of a systematic phytochemical study of the Alangium spp.…”

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confidence: 99%