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Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai
School of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan
Division of Herbal Drug and Natural Products, National Research Institute of Chinese Medicine, Taipei 112, Taiwan
College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA
Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 404, Taiwan
These authors contribute equally to this work.
* Author to whom correspondence should be addressed.
Received: 26 January 2012; in revised form: 6 February 2012 / Accepted: 7 February 2012 / Published: 14 February 2012
Abstract: 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 ED50 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).
Keywords: Staphyleaceae; Turpinia formosana Nakai; turformosin A; turfomosinic acid; cytotoxicity
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Huang, H.-C.; Chiou, C.-T.; Hsiao, P.-C.; Liaw, C.-C.; Zhang, L.-J.; Chang, C.-L.; Chen, I.-S.; Chen, W.-C.; Lee, K.-H.; Kuo, Y.-H. Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai. Molecules 2012, 17, 1837-1851.
Huang H-C, Chiou C-T, Hsiao P-C, Liaw C-C, Zhang L-J, Chang C-L, Chen I-S, Chen W-C, Lee K-H, Kuo Y-H. Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai. Molecules. 2012; 17(2):1837-1851.
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. 2012. "Cytotoxic Phenylpropanoids and a New Triterpene, Turformosinic Acid, from Turpinia formosana Nakai." Molecules 17, no. 2: 1837-1851.