Schisandrene, a dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans.
Phytochemical investigation of the fruits of Schisandra chinensis led to the isolation of 13 lignans including schisandrene (13), a new lignan based on a dibenzocyclooctadiene backbone with an exocyclic double bond. Its structure and absolute configuration were established using NMR, MS, and CD data. Antioxidant activity of the lignans was evaluated using a DCFH-DA cellular-based assay. The structure-activity relationships of the dibenzocyclooctadiene lignans showed that the exocyclic methylene functionality was essential for antioxidant activity, with the benzoyloxy group probably enhancing such effects.
Choi
Young-Whan
YW
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, 38677, USA.
Takamatsu
Satoshi
S
Khan
Shabana I
SI
Srinivas
Pullela V
PV
Ferreira
Daneel
D
Zhao
Jianping
J
Khan
Ikhlas A
IA
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D034242:Cyclooctanes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007723:Korea; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D032141:Schisandra / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000975:Antioxidants; D034242:Cyclooctanes; D017705:Lignans; C510060:schisandrene