Cytotoxic neolignans from the traditional Chinese medicine Daphniphyllum macropodum Miq.
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Author(s)
Ma, Xinhua
Yang, Jie
Brown, Christopher L
Wang, Chao
Deng, Shihao
Ke, Ruifang
Xu, Shicheng
Huang, Mi
Yang, Xinzhou
Feng, Yunjiang
Griffith University Author(s)
Year published
2017
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Four new neolignans, (E)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-6-ol (1), methyl (E)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carboxylate (2), (R)-4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)benzaldehyde (3) and methyl (E,R)-3-(4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)phenyl)acrylate (4) were isolated from the seeds of Daphniphyllum macropodum Miq, together with four known compounds. The structures of the new compounds were established by spectroscopic analyses, including 1D and 2D NMR as well as HRESIMS data. The absolute configurations of 3 and 4 were determined by the ...
View more >Four new neolignans, (E)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-6-ol (1), methyl (E)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carboxylate (2), (R)-4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)benzaldehyde (3) and methyl (E,R)-3-(4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)phenyl)acrylate (4) were isolated from the seeds of Daphniphyllum macropodum Miq, together with four known compounds. The structures of the new compounds were established by spectroscopic analyses, including 1D and 2D NMR as well as HRESIMS data. The absolute configurations of 3 and 4 were determined by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. All the compounds were evaluated for their antiproliferative activity on human NSCLC A549 and H460 cell lines. Compound 2 significantly inhibited the cancer cell growth in a dose-dependent manner. Mechanism of the action studies showed that 2 increased the expression of bax, caspase-3 and caspase-9, and decreased the production of bcl-2, suggesting that 2 induced apoptosis in A549 cells through activating the mitochondrial pathway.
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View more >Four new neolignans, (E)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-6-ol (1), methyl (E)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carboxylate (2), (R)-4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)benzaldehyde (3) and methyl (E,R)-3-(4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)phenyl)acrylate (4) were isolated from the seeds of Daphniphyllum macropodum Miq, together with four known compounds. The structures of the new compounds were established by spectroscopic analyses, including 1D and 2D NMR as well as HRESIMS data. The absolute configurations of 3 and 4 were determined by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. All the compounds were evaluated for their antiproliferative activity on human NSCLC A549 and H460 cell lines. Compound 2 significantly inhibited the cancer cell growth in a dose-dependent manner. Mechanism of the action studies showed that 2 increased the expression of bax, caspase-3 and caspase-9, and decreased the production of bcl-2, suggesting that 2 induced apoptosis in A549 cells through activating the mitochondrial pathway.
View less >
Journal Title
RSC Advances
Volume
7
Issue
83
Copyright Statement
© The Author(s) 2017. This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported (CC BY-NC 3.0) License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited.
Subject
Chemical sciences
Other chemical sciences not elsewhere classified