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.
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, 38677, USA.
Young-Whan
YW
Choi
Satoshi
S
Takamatsu
Shabana I
SI
Khan
Pullela V
PV
Srinivas
Daneel
D
Ferreira
Jianping
J
Zhao
Ikhlas A
IA
Khan
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