Cytotoxic macrocyclic diterpenoids from Jatropha multifida |
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| Institution: | 1. Institute of Traditional Chinese Medicine & Natural Products, Jinan University, China;2. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, China;3. College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, China;1. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China;2. Key Laboratory of Tropical Plant Resource and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Yunnan 666303, China;1. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, and Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, PR China;2. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, PR China;3. Key Laboratory of Tropical Plant Resource and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Yunnan 666303, PR China;4. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, PR China;1. Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil;2. Department of Natural Sciences, Mid Sweden University, SE-851 70 Sundsvall, Sweden;3. Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil;4. Instituto de Química, Universidade Estadual Paulista, Araraquara, SP, Brazil;5. Departamento de Bioquímica e Biologia Molecular, Instituto de Ciências Biológicas, Universidade Federal de Goiás, Brazil;1. Department of Microbial and Biochemical Pharmacy, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China;2. Lab of Pharmacognosy and Phytochemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China;3. School of Traditional Dai-Thai Medicine West Yunnan University of Applied Science, Yunnan, 666100, China |
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| Abstract: | Nine new macrocyclic diterpenoids (1–9), jatromultones A-I, along with eight known analogues (10–17) were isolated from the trunks of Jatropha multifida. The structures of the new compounds, including their absolute configurations, were elucidated by combination of spectroscopic analysis, single crystal X-ray diffraction, Rh2(OCOCF3)4-induced CD method, and chemical correlations. All compounds were screened for the cytotoxicity against five cancer cell lines, including one drug-resistant cell line, and seven compounds exhibited significant activity with IC50 values less than 10 μM. Compound 4 with IC50 values ranging from 2.69 to 6.44 μM toward all cell lines was selected for further mechanistic study, which showed that 4 could arrest cell cycle at G2/M phase and induce apoptosis. The brief structure-activity relationships (SARs) of these macrocyclic diterpenoids were also discussed. |
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| Keywords: | Macrocyclic diterpenoid Absolute configuration Cytotoxicity |
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