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Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha.

State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, People's Republic of China. College of Chemistry and Environmental Sciences, Kashgar University, Kashgar 844000, People's Republic of China. Key Laboratory for Tibet Plateau Phytochemistry of Qinghai Province, College of Pharmacy, Qinghai Nationalities University, Xining 810007, People's Republic of China. Tianjin Second People's Hospital, Tianjin 300192, People's Republic of China. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China. College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea. Department of Plant and Soil Sciences, University of Pretoria, Pretoria 0002, South Africa.

Journal of natural products. 2020;(4):894-904
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Abstract

Eight new neo-clerodane diterpenoids (1-8) were acquired from the aerial parts of Ajuga pantantha. Spectroscopic data analysis permitted the definition of their structures, and experimental and calculated electronic circular dichroism data were used to define their absolute configurations. Compounds 2 and 4-8 were found to have NO inhibitory effects with IC50 values of 20.2, 45.5, 34.0, 27.0, 45.0, and 25.8 μM, respectively. The more potent compounds 2, 6, and 8 were analyzed to establish their anti-inflammatory mechanism, including regulation of the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins as well as their binding interactions with the two proteins.