Crystal structure and optical activity of 2-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-3-yl acetate / 药学实践杂志

Objective To investigate the structure and optical activity of flavonoid derivative:2-(3,4-dimethoxyphenyl)-4-oxo-4 H-chromen-3-yl acetate(4).Methods The absolute configuration was obtained by X-ray single crystal diffraction.The optical rotation of the compound was determined by the SGW ?R-1 automatic polarimeter.Results X-ray single crystal diffrac-tion showed that compound 4 belongs to the orthorhombic space group P212121with a=7.763(2)?A,b=13.930(4)?A and c=14.906(4),α= β= γ=90.00°,V =1611.91(8)?A3,Z=8.There is no hydrogen bonding between the molecules in this crystal state.The molecules maintain their stable arrangement in space by van der Waals forces.It can be seen from the single-crystal data that there is a 33.9(2)° torsion of the dimethoxy-substituted benzene ring in the compound 4 with respect to the 4 H-chromene skeleton,suggesting that there may exist optical activity.Further experimental results of the optical rotation proved that the compound has a L-rotatory,specific rotation[α]19.1D = -5.077°.Conclusion The results of the single crystal indicated that the benzene ring substituted with dimethoxy group in compound 4 has a 33.9(2)° torsion relative to the 4 H-chromene skeleton,which results in chirality and optical activity.This is the first report that non-flavonoid-glycoside has optical activity.

Studies on the synthesis and anti-fatigue activity of the salidroside derivatives / 药学实践杂志

Objective A series of 4 substituted salidroside derivatives were designed and synthesized .Their anti-fatigue effects were investigated .Methods With five-acetyl glucose and different 4-substituted benzyl tyrosols as the starting materi-als ,salidroside derivatives were synthesized through glycosidation and deacetylation reactions .The exercise exhaustive mice model was used to study the anti-fatigue effects of those synthesized derivatives by comparing the loading swimming time of mice .Results 10 novel salidroside derivatives were synthesized .The loading swimming tests showed that the swimming time of the mice in the positive group (salidroside) and 3a-1 group (phenethyl-β-D-glucoside) was longer than that in the control group with statistically significant difference(P<0 .05) .The swimming times for other groups were similar to control group with no statistically significant difference .Conclusion This synthetic method for salidroside derivatives was convenient and feasible for large production .The 4-hydroxyl groups on the benzene ring of salidroside and its derivatives may be the active site responsible for their anti-fatigue activity .