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Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata
School of Pharmacy, Taipei Medical University, Taipei 110, Taiwan
Yong Chung Prosperous Biotech Co. Ltd., New Taipei 231, Taiwan
Twherb Biomedical Co. Ltd., Jhubei 302, Taiwan
Tsuzuki Institute for Traditional Medicine, College of Pharmacy, China Medical University, 404 Taichung, Taiwan
School of Medicine, Taipei Medical University, Taipei 110, Taiwan
These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 15 May 2013; in revised form: 20 June 2013 / Accepted: 21 June 2013 / Published: 28 June 2013
Abstract: A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3′-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.
Keywords: Antrodia camphorata; enynyl-benzenoid; antrocamphin O; synthesis; cytotoxic activity
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MDPI and ACS Style
Chen, P.-Y.; Wu, J.-D.; Tang, K.-Y.; Yu, C.-C.; Kuo, Y.-H.; Zhong, W.-B.; Lee, C.-K. Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata . Molecules 2013, 18, 7600-7608.
Chen P-Y, Wu J-D, Tang K-Y, Yu C-C, Kuo Y-H, Zhong W-B, Lee C-K. Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata . Molecules. 2013; 18(7):7600-7608.
Chen, Pi-Yu; Wu, Jen-Der; Tang, Kai-Yih; Yu, Chieh-Chou; Kuo, Yueh-Hsiung; Zhong, Wen-Bin; Lee, Ching-Kuo. 2013. "Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata ." Molecules 18, no. 7: 7600-7608.