10.1021/acs.jnatprod.9b00670.s001
You-Sheng Cai
You-Sheng
Cai
Cong Wang
Cong
Wang
Congkui Tian
Congkui
Tian
Wen-Ting Sun
Wen-Ting
Sun
Ling Chen
Ling
Chen
Di Xiao
Di
Xiao
Si-Yuan Zhou
Si-Yuan
Zhou
Guofu Qiu
Guofu
Qiu
Jianqing Yu
Jianqing
Yu
Kongkai Zhu
Kongkai
Zhu
Sheng-Ping Yang
Sheng-Ping
Yang
Octahydro-Protoberberine and Protoemetine-Type Alkaloids
from the Stems of <i>Alangium salviifolium</i> and Their
Cytotoxicity
American Chemical Society
2019
cancer cell lines
alangiifoliumine
9.4 μ M
dichroism spectra calculations
alkaloids
SKOV -3. Alkaloids 1
derivative
Alangium salviifolium
compound
IC
2019-09-12 18:35:19
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Octahydro-Protoberberine_and_Protoemetine-Type_Alkaloids_from_the_Stems_of_i_Alangium_salviifolium_i_and_Their_Cytotoxicity/9819404
Two octahydro-protoberberine alkaloids,
alangiifoliumines A (<b>1</b>) and B (<b>2</b>), and two
new protoemetine derivatives,
alangiifoliumines C (<b>3</b>) and D (<b>4</b>), together
with 11 known compounds, have been isolated from the stems of <i>Alangium salviifolium</i>. 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 <b>1</b> and <b>2</b> 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 <b>1</b>, <b>3</b>, and <b>6</b>–<b>14</b> exhibited inhibitory effects against all three human cancer cell
lines, with half-maximal inhibitory concentration (IC<sub>50</sub>) values in the range of 3 nM to 9.4 μM.