Sixteen new dammarane-type triterpenoid saponins(1-16)featuring diverse structural variations in the side chain at C-17,along with twenty-one known analogues(17-37),have been isolated from the rhizomes of Gynostemma l...Sixteen new dammarane-type triterpenoid saponins(1-16)featuring diverse structural variations in the side chain at C-17,along with twenty-one known analogues(17-37),have been isolated from the rhizomes of Gynostemma longipes C.Y.Wu,a plant renowned for its medicinal and edible properties.The structural elucidation of these compounds was accomplished through comprehensive analyses of 1D and 2D NMR and HRMS spectroscopic data,supplemented by comparison with previously reported data.Subsequent assays on the isolates for their protective effects against hypoxia-induced damage in pheochromocytoma cells(PC12 cells)revealed that nine saponins exhibited significant anti-hypoxic activities.Further investigation into the anti-hypoxia mechanisms of the representative saponins demonstrated that compounds 22 and 36 markedly reduced the levels of hypoxia-induced apoptosis.Additionally,these compounds were found to decrease the release of lactate dehydrogenase(LDH)and malondialdehyde(MDA),while increasing the activity of superoxide dismutase(SOD),thereby indicating that the saponins could mitigate hypoxia-induced injuries by ameliorating apoptosis and oxidative stress.These findings offer substantial evidence for the future utilization and development of G.longipes,identifying dammarane-type triterpenoid saponins as its active anti-hypoxic constituents.展开更多
Four new dammarane-type triterpenoid saponins,namely notoginsenosides SFt1-SFt4(1-4)were isolated from the steamed leaves of Panax notoginseng(Burk.)F.H.Chen(Araliaceae),together with 17 known saponins.Their structure...Four new dammarane-type triterpenoid saponins,namely notoginsenosides SFt1-SFt4(1-4)were isolated from the steamed leaves of Panax notoginseng(Burk.)F.H.Chen(Araliaceae),together with 17 known saponins.Their structures were established on the basis of detailed spectroscopic analyses and acidic hydrolysis.The known ginsenosides Rk2 and Rh3 were obtained from P.notoginseng for the first time.All of these new saponins showed no in vitro cytotoxicity against five human cancer cell lines(HL-60,SMMC-7712,A-549,MCF-7,and SW480).展开更多
One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynoste...One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino.Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR,HR-TOF-MS,NMR.展开更多
Gypenosides,structurally analogous to ginsenosides and derived from a sustainable source,are recognized as the principal active compounds found in Gynostemma pentaphyllum,a Chinese medicinal plant used in the treatmen...Gypenosides,structurally analogous to ginsenosides and derived from a sustainable source,are recognized as the principal active compounds found in Gynostemma pentaphyllum,a Chinese medicinal plant used in the treatment of the metabolic syndrome.By bioactive tracking isolation of the plants collected from different regions across China,we obtained four new gypenosides(1−4),together with nine known gypenosides(5−13),from the methanol extract of the plant.The structures of new gypenosides were elucidated by one-dimensional(1D)and two-dimensional(2D)nuclear magnetic resonance(NMR)spectra,complemented by chemical degradation experiments.Through comprehensive evaluation involving COL1A1 promoter assays and PP2Cαactivity assays,we established a definitive structure-activity relationship for these dammarane-type triterpenoids,affirming the indispensability of the C-3 saccharide chain and C-17 lactone ring in effectively impeding extracellular matrix(ECM)deposition within hepatic stellate cells.Further in vivo study on the CCl4-induced liver damage mouse model corroborated that compound 5 significantly ameliorated the process of hepatic fibrosis by oral administration.These results underscore the potential of dammarane-type triterpenoids as prospective antifibrotic leads and highlight their prevalence as key molecular frameworks in the therapeutic intervention of chronic hepatic disorders.展开更多
Three new dammarane-type glycosides (1-3) had been isolated from the aerial part of Gynostemma pentaphyllum (Thunb) Makino. The structures of compounds 1-3 had been elucidated as 3b, 12b, 25-trihydroxy-20(S), 24(S)-ep...Three new dammarane-type glycosides (1-3) had been isolated from the aerial part of Gynostemma pentaphyllum (Thunb) Makino. The structures of compounds 1-3 had been elucidated as 3b, 12b, 25-trihydroxy-20(S), 24(S)-epoxydammarane 3-O-b-D-glucopyranosyl (12)-b-D- xylo -pyranoside, 3b, 12b, 25-trihydroxy-20(S), 24(R)-epoxydammarane 3-O-b-D-glucopyranosyl (12) -b-D-xylopyranoside and 3b, 12b, 23b, 25-tetrahydroxy-20(S), 24(S)-epoxydammarane 3-O-b-D- glucopyranosyl (12)-b-D-xylopyranoside, respectively, on the basis of chemical and spectro -scopic methods.展开更多
文摘Sixteen new dammarane-type triterpenoid saponins(1-16)featuring diverse structural variations in the side chain at C-17,along with twenty-one known analogues(17-37),have been isolated from the rhizomes of Gynostemma longipes C.Y.Wu,a plant renowned for its medicinal and edible properties.The structural elucidation of these compounds was accomplished through comprehensive analyses of 1D and 2D NMR and HRMS spectroscopic data,supplemented by comparison with previously reported data.Subsequent assays on the isolates for their protective effects against hypoxia-induced damage in pheochromocytoma cells(PC12 cells)revealed that nine saponins exhibited significant anti-hypoxic activities.Further investigation into the anti-hypoxia mechanisms of the representative saponins demonstrated that compounds 22 and 36 markedly reduced the levels of hypoxia-induced apoptosis.Additionally,these compounds were found to decrease the release of lactate dehydrogenase(LDH)and malondialdehyde(MDA),while increasing the activity of superoxide dismutase(SOD),thereby indicating that the saponins could mitigate hypoxia-induced injuries by ameliorating apoptosis and oxidative stress.These findings offer substantial evidence for the future utilization and development of G.longipes,identifying dammarane-type triterpenoid saponins as its active anti-hypoxic constituents.
基金This work was supported by the 973 Program of Ministry of Science and Technology of China(2011CB915503).
文摘Four new dammarane-type triterpenoid saponins,namely notoginsenosides SFt1-SFt4(1-4)were isolated from the steamed leaves of Panax notoginseng(Burk.)F.H.Chen(Araliaceae),together with 17 known saponins.Their structures were established on the basis of detailed spectroscopic analyses and acidic hydrolysis.The known ginsenosides Rk2 and Rh3 were obtained from P.notoginseng for the first time.All of these new saponins showed no in vitro cytotoxicity against five human cancer cell lines(HL-60,SMMC-7712,A-549,MCF-7,and SW480).
基金supported by E&T modern center for Natural products of Liaoning Province of China (No.2006-19-10)
文摘One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino.Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR,HR-TOF-MS,NMR.
基金supported by the National Key R&D Program(No.2018YFC1707900)the National Natural Science Foundation of China(No.22177052)+1 种基金Jiangsu Provincial Science and Technology Development Project of Chinese Medicine(No.ZD202002)Jiangsu postgraduate scientific research innovation program(No.KYCX21_1721).
文摘Gypenosides,structurally analogous to ginsenosides and derived from a sustainable source,are recognized as the principal active compounds found in Gynostemma pentaphyllum,a Chinese medicinal plant used in the treatment of the metabolic syndrome.By bioactive tracking isolation of the plants collected from different regions across China,we obtained four new gypenosides(1−4),together with nine known gypenosides(5−13),from the methanol extract of the plant.The structures of new gypenosides were elucidated by one-dimensional(1D)and two-dimensional(2D)nuclear magnetic resonance(NMR)spectra,complemented by chemical degradation experiments.Through comprehensive evaluation involving COL1A1 promoter assays and PP2Cαactivity assays,we established a definitive structure-activity relationship for these dammarane-type triterpenoids,affirming the indispensability of the C-3 saccharide chain and C-17 lactone ring in effectively impeding extracellular matrix(ECM)deposition within hepatic stellate cells.Further in vivo study on the CCl4-induced liver damage mouse model corroborated that compound 5 significantly ameliorated the process of hepatic fibrosis by oral administration.These results underscore the potential of dammarane-type triterpenoids as prospective antifibrotic leads and highlight their prevalence as key molecular frameworks in the therapeutic intervention of chronic hepatic disorders.
文摘Three new dammarane-type glycosides (1-3) had been isolated from the aerial part of Gynostemma pentaphyllum (Thunb) Makino. The structures of compounds 1-3 had been elucidated as 3b, 12b, 25-trihydroxy-20(S), 24(S)-epoxydammarane 3-O-b-D-glucopyranosyl (12)-b-D- xylo -pyranoside, 3b, 12b, 25-trihydroxy-20(S), 24(R)-epoxydammarane 3-O-b-D-glucopyranosyl (12) -b-D-xylopyranoside and 3b, 12b, 23b, 25-tetrahydroxy-20(S), 24(S)-epoxydammarane 3-O-b-D- glucopyranosyl (12)-b-D-xylopyranoside, respectively, on the basis of chemical and spectro -scopic methods.
