Cytotoxic terpenoids from the stem bark of Taxus wallichiana |
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| Affiliation: | 1. Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam;2. Institute of Biotechnology, VAST, Hanoi, Viet Nam;1. Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon;2. Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon;3. Université de Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France;4. Food Science, Department of Chemistry, Carleton University, Room 207D Steacie Building, 1125 Colonel by Drive, K1S 5B6 Ottawa, Canada;1. UMR 152 PharmaDev, Université de Toulouse, IRD, UPS, Toulouse, France;2. Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Peru;3. Institut de Chimie de Toulouse, ICT UAR 2599, Université Paul Sabatier-Toulouse III, Toulouse, France;1. Thuyloi University, 175 Tay Son, Dong Da, Hanoi, Viet Nam;2. Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam;3. Institute of Ecology and Biological Resources, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam;1. Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China;2. College of Life Sciences, Inner Mongolia Agricultural University, Hohhot 010018, PR China;3. College of Pharmacy, Inner Mongolia Medical University, Hohhot 010110, PR China;4. Inner Mongolia Grand Pharmaceutical Co., Ltd, Hohhot 010010, PR China;1. Beijing Key laboratory of Bioactive Substances and Functional Foods, Beijing Union University, Beijing 100191, China;2. College of Food Science and Technology, Henan Agricultural University, Zhengzhou 450002, China |
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| Abstract: | Chemical study of the stem bark of Taxus wallichiana Zucc. afforded the isolation of two new cyclopenta[b]naphthalene terpenoids, wallichianones A (1) and B (2) and 13 taxane diterpenoids, baccatin III (3), 10-deacetylbaccatin III (4), baccatin IV (5), 1-dehydroxybaccatin IV (6), 1-deoxybaccatin VI (7), taxol (8), 10-deacetyltaxol (9), 7-epi-10-deacetyltaxol (10), taxol-7-xyloside (11), 7-xylosyl-10-deacetyltaxol C (12), cephalomannine (13), 10-deacetylcaphalomannine (14), and 7-epi-10-deacetylcephalomannine (15). Their structures were identified by comprehensive analyses of the spectroscopic methods, including NMR and mass spectra. The absolute configurations of 1 and 2 were clarified by time-dependent density functional theory (TD-DFT) electronic circular dichroism (ECD) spectroscopic analyses. Compounds 3 and 7–15 showed cytotoxicity against all five human cancer cell lines, including lung (SK-LU-1), liver (HepG2), breast (MCF7), skin (SK-Mel-2), and prostate (LNCaP), with IC50 values ranging from 1.4 ± 0.2 to 88.1 ± 5.8 μM. Compounds 9–11, 14, and 15 were additionally cytotoxic against human embryonic kidney (HEK-293A) cell line (IC50 = 14.5 ± 1.0–48.4 ± 1.0 μM), however, 13 was noncytotoxic toward this cell line. The positive control, ellipticine showed cytotoxicity against all the cell lines, with IC50 values in a range of 1.5 ± 0.1–2.0 ± 0.3 μM. Preliminary analysis of the structural and cytotoxicity relationship of compounds 3–15 suggested that the phenylalanine substituent at C-13 may contribute an important role for the cytotoxicity of the taxane diterpenoids. |
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| Keywords: | Taxaceae Taxane diterpenoid Cytotoxicity |
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