Schisandrene, a Dibenzocyclooctadiene Lignan from Schisandra chinensis:  Structure−Antioxidant Activity Relationships of Dibenzocyclooctadiene Lignans

Abstract

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.

Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: Absolute configuration, and their estrogenic and anti-proliferative activity

“…On the contrary, it is expected that the two chromophores interact with each other according to the exciton-coupled CD mechanism [28], which may in principle generate strong CD signals [29]. In practice, it cannot be taken for granted that the helicity rule may be applied to benzoatecontaining lignans such as 1, as it is commonly done [3,14,24,30,31]. In fact, if we compare the CD spectrum of 1 (Fig.…”

Ultra performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometric procedure for qualitative and quantitative analyses of nortriterpenoids and lignans in the genus Schisandra

“…A formula database of known lignans in S. chinensis and S. sphenanthera has been established in our laboratory, which was used to tentatively identify 19 lignans (peaks 18-37) by comparing the exact masses and formulae of their MS and MS/MS data acquired by UPLC-QTOF-MS with those of literatures. Those include angeloylgomisin H (18) [14,15], tigloylgomisin H (19) [14,15], schisandrol B (20) [14,15], benzoylgomision H (21) [15], tigloylgomisin Q (22) [14,15], schisanhernol (23) [15,17], schisantherin B (24) [14,15], schisantherin C (25) [14,15], wuweilignan D (26) [32], schisantherin D (27) [14,16], gomisin K1 (28) [18], wuweilignan L (29) [32], gomisin O (30) [14], gomision M2 (31) [7,14] [17], ␥-schsandrin (32) [14,17] schisandrene (33) [33], benzoylgomisin O (34) [18], tigloylgomisin O (35) [18], gomisin R (36) [14] and pregomisin (37) [14].…”

Effects of gomisin A on vascular contraction in rat aortic rings

“…Schisandra chinensis have some beneficial effects including hepatoprotective, antioxidative, anti-inflammatory, anticancer, and anti-HIV actions (Chen et al 1997;Chiu et al 2002;Choi et al 2006;Wu et al 2003;Yasukawa et al 1992). The fruit of Schisandra chinensis is known to be enriched with lignans (Nakajima et al 1983), of which schisandrin (2-9%), γ-schisandrin (1-5%), deoxyschisandrin (0.2-1.1%), and GA (0.7-3%) are major ingredients, depending on the plant origin and harvest season (% dry weight) (He et al 1997;Park et al 2007).…”