Novel cycloneolignans from Vernicia fordii with inhibitory effects on over-activation of BV2 cells in vitro

• Published in: Scientific reports Vol. 7; no. 1; pp. 13608 - 10
• Main Authors: Zhao, Wei-Hong, Li, Ning, Chu, Yang, Sun, Tao, Wang, Jian, Wang, Wen-Li, Li, Jia-Yuan, Lin, Bin, Chen, Ru, Hou, Yue
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 19.10.2017; Nature Publishing Group
• Subjects: 631/378/1689; 639/638; Alzheimer's disease; Animals; Binding Sites; Bioassays; Cell Line; Cotton; Euphorbiaceae - chemistry; Euphorbiaceae - metabolism; Humanities and Social Sciences; Hydrocarbons; Interleukin-1beta - metabolism; Interleukin-6 - metabolism; Laboratories; Lignans - chemistry; Lignans - isolation & purification; Lignans - metabolism; Lignans - pharmacology; Lipopolysaccharides; Lipopolysaccharides - pharmacology; Mice; Microglia; Microglia - cytology; Microglia - drug effects; Microglia - metabolism; Molecular Conformation; Molecular Docking Simulation; multidisciplinary; Natural products; Nitric Oxide - metabolism; Nitric Oxide Synthase Type II - chemistry; Nitric Oxide Synthase Type II - metabolism; Nonsteroidal anti-inflammatory drugs; Pharmaceuticals; Plant Extracts - chemistry; Science; Science (multidisciplinary); Seeds; Seeds - chemistry; Seeds - metabolism; Stereoisomerism; Stereoselectivity; Vernicia fordii
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-017-14062-z

Novel natural products 7 R , 8 R , 7′ R , 9′ S -verniciasin A ( 1a ), 7 S , 8 S , 7′ S , 9′ R - verniciasin A ( 1b ), 7 R , 8 R , 7′ R , 9′ S −7′-methoxylverniciasin A ( 2a ) and 7 S , 8 S , 7′ S , 9′ R −7′-methoxylverniciasin A ( 2b ) were characterized from the seed capsule of Vernicia fordii . And the unique 9-O-9′−7, 9′-cyclo-8, 1′-neolignan skeleton with a seven-membered ring, was identified by extensive spectroscopic analysis. Further the possible biosynthetic pathway was briefly discussed. Interestingly, 1a , 2a , 1b and 2b all exhibited significant stereoselective inhibitory effects on NO production in LPS-induced BV2 microglia cell. Then the primary mechanism of the bioactivities and stereoselectivity was explored by means of bioassay and molecular docking.