Two pairs of enantiomers,(−)and(+)-securidanes A(1 and 2)and B(3 and 4)featuring unprecedented triarylmethane(TAM)skeletons,were isolated from Securidaca inappendiculata.Teir structures were established by spectroscop...Two pairs of enantiomers,(−)and(+)-securidanes A(1 and 2)and B(3 and 4)featuring unprecedented triarylmethane(TAM)skeletons,were isolated from Securidaca inappendiculata.Teir structures were established by spectroscopic data,X-ray crystallography,and CD analysis.A plausible biosynthetic pathway for 1−4 based on the co-isolated precursors was proposed.Bioinspired total synthesis of 1−4was completed in high yield,which in turn corroborated the biosynthetic hypothesis.Compounds 1−4 showed good inhibition against protein tyrosine phosphatase 1B(PTP1B).Te molecular docking demonstrated that the strongest inhibitor 3(IC50=7.52�M)reaches deeper into the binding pocket and has an additional H-bond.展开更多
基金Te authors thank Professor S.Q.Tang of Guangxi Normal University for the identifcation of the plant material.Te National Natural Science Foundation(nos.21532007,U1302222,81321092)and the Foundation from the MOST(2012CB721105)of China are gratefully acknowledged.
文摘Two pairs of enantiomers,(−)and(+)-securidanes A(1 and 2)and B(3 and 4)featuring unprecedented triarylmethane(TAM)skeletons,were isolated from Securidaca inappendiculata.Teir structures were established by spectroscopic data,X-ray crystallography,and CD analysis.A plausible biosynthetic pathway for 1−4 based on the co-isolated precursors was proposed.Bioinspired total synthesis of 1−4was completed in high yield,which in turn corroborated the biosynthetic hypothesis.Compounds 1−4 showed good inhibition against protein tyrosine phosphatase 1B(PTP1B).Te molecular docking demonstrated that the strongest inhibitor 3(IC50=7.52�M)reaches deeper into the binding pocket and has an additional H-bond.
