Five new flavan-4-ol glycosides jixueqiosides A-E(1-5)and two new flavan glycosides jixueqiosides F and G(6 and 7),along with twelve known flavan-4-ol glycosides(8-19),were isolated from the roots of Pronephrium penan...Five new flavan-4-ol glycosides jixueqiosides A-E(1-5)and two new flavan glycosides jixueqiosides F and G(6 and 7),along with twelve known flavan-4-ol glycosides(8-19),were isolated from the roots of Pronephrium penangianum.Comprehensive spectral analyses,X-ray single-crystal diffraction,and theoretical electronic circular dichroism(ECD)calculations established structures and absolute configurations.A single crystal structure of flavan-4-ol glycoside(14)was reported for the first time,while the characteristic ECD and NMR data for all isolated flavan-4-ol glycosides(1-5,8-19)were analyzed,establishing a set of empirical rules.Activity screening of these isolates showed that 8 and 9 could inhibit the proliferation of MDA-MB-231 and MCF-7 cells with IC50 values of 7.93±2.85μmol·L^(-1)and 5.87±1.58μmol·L^(-1)(MDA-MB-231),and 2.21±1.38μmol·L^(-1)and 3.52±1.55μmol·L^(-1)(MCF-7),respectively.Western blotting and flow cytometry analyses demonstrated that 8 and 9 dose-dependently induced apoptosis in MDA-MB-231 cells by up-regulating BAX,activating caspase-3 and down-regulating BCL-2.Additionally,compound 8 affected autophagy-related proteins,increasing the ratio of LC3-II/LC3-I and Beclin-1 levels to inhibit MDA-MB-231 cell proliferation.Moreover,anti-inflammatory studies indicated that 2,3,7,13,14,and 18 moderately inhibited tumor necrosis factor-α(TNF-α),interleukin-6(IL-6),and nitric oxide(NO)release.展开更多
基金supported by the National Natural Science Foundation of China(No.81874369)the Excellent Youth Project of the Hunan Provincial Department of Education(No.22B0388)the Project of Hunan Administration of Traditional Chinese Medicine(No.B2023143)。
文摘Five new flavan-4-ol glycosides jixueqiosides A-E(1-5)and two new flavan glycosides jixueqiosides F and G(6 and 7),along with twelve known flavan-4-ol glycosides(8-19),were isolated from the roots of Pronephrium penangianum.Comprehensive spectral analyses,X-ray single-crystal diffraction,and theoretical electronic circular dichroism(ECD)calculations established structures and absolute configurations.A single crystal structure of flavan-4-ol glycoside(14)was reported for the first time,while the characteristic ECD and NMR data for all isolated flavan-4-ol glycosides(1-5,8-19)were analyzed,establishing a set of empirical rules.Activity screening of these isolates showed that 8 and 9 could inhibit the proliferation of MDA-MB-231 and MCF-7 cells with IC50 values of 7.93±2.85μmol·L^(-1)and 5.87±1.58μmol·L^(-1)(MDA-MB-231),and 2.21±1.38μmol·L^(-1)and 3.52±1.55μmol·L^(-1)(MCF-7),respectively.Western blotting and flow cytometry analyses demonstrated that 8 and 9 dose-dependently induced apoptosis in MDA-MB-231 cells by up-regulating BAX,activating caspase-3 and down-regulating BCL-2.Additionally,compound 8 affected autophagy-related proteins,increasing the ratio of LC3-II/LC3-I and Beclin-1 levels to inhibit MDA-MB-231 cell proliferation.Moreover,anti-inflammatory studies indicated that 2,3,7,13,14,and 18 moderately inhibited tumor necrosis factor-α(TNF-α),interleukin-6(IL-6),and nitric oxide(NO)release.
