Diterpenoids from Wedelia prostrata and Their Derivatives and Cytotoxic Activities |
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| Authors: | Xin‐Hua Ma Zhi‐Biao Wang Lei Zhang Wei Li Cui‐Min Deng Tian‐Hua Zhong Guang‐Yu Li Wei‐Ming Zheng Yong‐Hong Zhang |
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| Affiliation: | 1. Key Laboratory of Natural Drug Pharmacology in Fujian Province, School of Pharmacy, Fujian Medical University, Fuzhou, P. R. China;2. Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen, P. R. China |
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| Abstract: | One new ent‐kaurane diterpenoid, 11β,16α‐dihydroxy‐ent‐kauran‐19‐oic acid ( 1 ), together with eight known analogues 2 – 9 were isolated from the aerial parts of Wedelia prostrata. One of the acidic diterpenoids, kaurenoic acid ( 3 ), was converted to seven derivatives, 10 – 16 . All compounds were evaluated for their cytotoxic activity in vitro against human leukemia (K562), liver (HepG‐2), and stomach (SGC‐7901) cancer cell lines. Only four kaurenoic acid derivatives, 13 – 16 , with 15‐keto and substitutions at C(19) position, exhibited notable cytotoxic activities on these tumor cell lines with IC50 value ranging from 0.05 to 3.71 μm . Compounds 10 – 12 , with oxime on C(15) showed moderate inhibitory effects and compounds 1 – 9 showed no cytotoxicities on them. Structure–activity relationships were also discussed based on the experimental data obtained. The known derivative, 15‐oxokaurenoic acid 4‐piperdin‐1‐ylbutyl ester ( 17 ), induced typical apoptotic cell death in colon SW480 cells upon evaluation of the apoptosis‐inducing activity by flow‐cytometric analysis. |
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| Keywords: |
Wedelia prostrata
Asteraceae ent‐Kaurane diterpenoid Cytotoxic activities Apoptosis‐inducing activities |
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