Phytochemicals with NO inhibitory effects and interactions with iNOS protein from Trigonostemon howii.

Jun Ma, Xueyuan Yang, Peixia Wang, Bangjian Dong, Guochen Su, Muhetaer Tuerhong, Da-Qing Jin, Jing Xu, Dongho Lee, Yasushi Ohizumi, Jianping Lin, Yuanqiang Guo

Journal: Bioorganic chemistry 2017;75():71-77

PMID: 28917124

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Abstract

A phytochemical investigation to obtain new NO inhibitors led to the isolation of nine compounds including one new guaiane-type sesquiterpenoid (1) and two new cleistanthane diterpenoids (2 and 3) from the stems of Trigonostemon howii. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of new compounds 1-3 were established via comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 2 and 3 possess a rare 3,4-seco-cleistanthane diterpenoid skeleton. All of the compounds showed inhibitory effects on lipopolysaccharide-induced NO production in murine microglial BV-2 cells. The further molecular docking studies indicated the strong interactions between some bioactive compounds with the iNOS protein, which revealed the possible and potential mechanism of NO inhibition of bioactive compounds.

Address: State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, People's Republic of China.; College of Chemistry and Environmental Sciences, Laboratory of Xinjiang Native Medicinal and Edible Plant Resources Chemistry, Kashgar University, Kashgar 844000, People's Republic of China.; School of Medicine, Nankai University, Tianjin 300071, People's Republic of China.; State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, People's Republic of China. Electronic address: [email protected].; Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea.; Department of Medical Biochemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan.; State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, People's Republic of China. Electronic address: [email protected].

DOI: 10.1016/j.bioorg.2017.08.008

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MeSH Terms: Binding Sites, Catalytic Domain, Circular Dichroism, Diterpenes, Enzyme Inhibitors, Euphorbiaceae, Magnetic Resonance Spectroscopy, Molecular Conformation, Molecular Docking Simulation, Nitric Oxide, Nitric Oxide Synthase Type II, Phytochemicals, Plant Stems, Sesquiterpenes, Guaiane, Thermodynamics