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Bioorg Chem. 2018 Feb;76:53-60. doi: 10.1016/j.bioorg.2017.10.008. Epub 2017 Oct 21.

Nitric oxide inhibitors with a spiro diterpenoid skeleton from Scutellaria formosana: Structures, NO inhibitory effects, and interactions with iNOS.

Author information

1
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.
2
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.
3
School of Medicine, Nankai University, Tianjin 300071, People's Republic of China.
4
Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Republic of Korea.
5
Department of Medical Biochemistry, School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan.
6
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. Electronic address: victgyq@nankai.edu.cn.

Abstract

A phytochemical investigation to obtain new NO inhibitors resulted in the isolation of five new spiro diterpenoids (1 -5) from the aerial parts of Scutellaria formosana. The structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established via comparison of experimental and calculated electronic circular dichroism (ECD) spectra. The nitric oxide (NO) inhibitory effects were evaluated and all of the compounds showed inhibitory effects on lipopolysaccharide-induced NO production in murine microglial BV-2 cells. The possible mechanism of NO inhibition of bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the iNOS protein.

KEYWORDS:

Molecular docking; NO inhibitors; Scutellaria formosana; Spiro diterpenoid; iNOS

PMID:
29128707
DOI:
10.1016/j.bioorg.2017.10.008
[Indexed for MEDLINE]

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