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Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai

One new phenylpropanoid, turformosin A (1), and one new triterpene, turformosinic acid (2), together with 16 known compounds, were isolated from the stems of Turpinia formosana Nakai. All structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques and MS an...

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Autores principales: Huang, Hui-Chi, Chiou, Chun-Tang, Hsiao, Ping-Chun, Liaw, Chia-Ching, Zhang, Li-Jie, Chang, Chao-Lin, Chen, Ih-Sheng, Chen, Wen-Chi, Lee, Kuo-Hsiung, Kuo, Yao-Haur
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268649/
https://www.ncbi.nlm.nih.gov/pubmed/22334062
http://dx.doi.org/10.3390/molecules17021837
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author Huang, Hui-Chi
Chiou, Chun-Tang
Hsiao, Ping-Chun
Liaw, Chia-Ching
Zhang, Li-Jie
Chang, Chao-Lin
Chen, Ih-Sheng
Chen, Wen-Chi
Lee, Kuo-Hsiung
Kuo, Yao-Haur
author_facet Huang, Hui-Chi
Chiou, Chun-Tang
Hsiao, Ping-Chun
Liaw, Chia-Ching
Zhang, Li-Jie
Chang, Chao-Lin
Chen, Ih-Sheng
Chen, Wen-Chi
Lee, Kuo-Hsiung
Kuo, Yao-Haur
author_sort Huang, Hui-Chi
collection PubMed
description One new phenylpropanoid, turformosin A (1), and one new triterpene, turformosinic acid (2), together with 16 known compounds, were isolated from the stems of Turpinia formosana Nakai. All structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques and MS analysis. Selected isolated compounds were evaluated for in vitro cytotoxicity against four human cancer cell lines and antioxidant scavenging effects on DPPH. (−)-(7′S,8′S)-threo-carolignan X (3) exhibited cytotoxicity against Hep2, WiDr, Daoy, and MCF-7 cell lines with ED(50) values of 3.60, 4.45, 6.07, and 13.7 μg/mL, respectively. Turformosin A (1), (−)-(7′S,8′S)-threo-carolignan X (3), methoxyhydroquinone-4-β-D-glucopyranoside (5), and methoxy-hydroquinone-1-β-D-glucopyranoside (6), exhibited similar anti-oxidative activity. Hep2 cells treated with 10 μg/mL of 3 showed elevation of sub-G1 population (from 20% at 8 h to 60% at 48 h), and activation of caspase-9/caspase-3/PARP cascade. Compound 3 induced intrinsic apoptotic pathway in Hep2 cells with dose and time dependence (10 μg/mL for 8 h).
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spelling pubmed-62686492018-12-10 Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai Huang, Hui-Chi Chiou, Chun-Tang Hsiao, Ping-Chun Liaw, Chia-Ching Zhang, Li-Jie Chang, Chao-Lin Chen, Ih-Sheng Chen, Wen-Chi Lee, Kuo-Hsiung Kuo, Yao-Haur Molecules Article One new phenylpropanoid, turformosin A (1), and one new triterpene, turformosinic acid (2), together with 16 known compounds, were isolated from the stems of Turpinia formosana Nakai. All structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques and MS analysis. Selected isolated compounds were evaluated for in vitro cytotoxicity against four human cancer cell lines and antioxidant scavenging effects on DPPH. (−)-(7′S,8′S)-threo-carolignan X (3) exhibited cytotoxicity against Hep2, WiDr, Daoy, and MCF-7 cell lines with ED(50) values of 3.60, 4.45, 6.07, and 13.7 μg/mL, respectively. Turformosin A (1), (−)-(7′S,8′S)-threo-carolignan X (3), methoxyhydroquinone-4-β-D-glucopyranoside (5), and methoxy-hydroquinone-1-β-D-glucopyranoside (6), exhibited similar anti-oxidative activity. Hep2 cells treated with 10 μg/mL of 3 showed elevation of sub-G1 population (from 20% at 8 h to 60% at 48 h), and activation of caspase-9/caspase-3/PARP cascade. Compound 3 induced intrinsic apoptotic pathway in Hep2 cells with dose and time dependence (10 μg/mL for 8 h). MDPI 2012-02-14 /pmc/articles/PMC6268649/ /pubmed/22334062 http://dx.doi.org/10.3390/molecules17021837 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Huang, Hui-Chi
Chiou, Chun-Tang
Hsiao, Ping-Chun
Liaw, Chia-Ching
Zhang, Li-Jie
Chang, Chao-Lin
Chen, Ih-Sheng
Chen, Wen-Chi
Lee, Kuo-Hsiung
Kuo, Yao-Haur
Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
title Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
title_full Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
title_fullStr Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
title_full_unstemmed Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
title_short Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
title_sort cytotoxic phenylpropanoids and a new triterpene, turformosinic acid, from turpinia formosana nakai
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268649/
https://www.ncbi.nlm.nih.gov/pubmed/22334062
http://dx.doi.org/10.3390/molecules17021837
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