Callicarpanes A–L,Twelve New Clerodane Diterpenoids with NLRP3 Inflammasome Inhibitory Activity from Callicarpa integerrima |
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Authors: | De-Wen Bi Ying-Xin Zhao Xiong Qiu Xue-Cong Zhang Ya-Ling Zhou Muhammad Aurang Zeb Wen-Hui Pang Rui Li Meng-Ru Wang Bin Cheng Jing-Jing Zhang Xing-Jie Zhang Xiao-Li Li Rui-Han Zhang Wei-Lie Xiao |
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Institution: | 1. Key Laboratory of Medicinal Chemistry for Natural Resource of Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology and School of Medicine, Yunnan University, Kunming, 650500 P. R. China
Equally contributed to this research work.;2. Key Laboratory of Medicinal Chemistry for Natural Resource of Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology and School of Medicine, Yunnan University, Kunming, 650500 P. R. China |
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Abstract: | Twelve new clerodane diterpenoids named callicarpanes A–L ( 1 – 12 ), together with eight known compounds ( 13 – 20 ), were isolated from Callicarpa integerrima. Their structures were determined by comprehensive spectroscopic data. The calculated chemical shifts were used to identify relative configurations using DP4+ analysis. The absolute configurations (AC) were assigned based on quantum chemical calculations and X-ray single-crystal diffraction methods. Compounds 1 , 3 , 5 , 9 , 10 , 12 , 15 , 16 , and 19 showed significant inhibitory activity for NLRP3 inflammasome activation, with the IC50 against lactate dehydrogenase (LDH) release ranging from 0.08 to 4.78 μM. Further study revealed that compound 10 repressed IL-1β secretion and caspase-1 maturation in J774A.1 cell as well as blocked macrophage pyroptosis. |
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Keywords: | clerodane diterpenoids callicarpa quantum chemical calculations NLRP3 inflammasome Callicarpa integerrima |
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