Two new saponins from Thalictrum fortunei

Two new cycloartane glycosides were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The chemical structures of these compounds were elucidated as 3-O-β-d-glucopyranosyl (1 → 4)-β-d-fucopyranosyl-(22S,24Z)-cycloart-24-en-3β,22,26,30-tetraol 26-O-β-d-glucopyranoside and 3-O-β-d-glucopyranosyl (1 → 4)-β-d-fucopyranosyl-(22S,24Z)-cycloart-24-en-3β,22,26,29-tetraol 26-O-β-d-glucopyranoside by extensive 1D and 2D NMR methods, HR-ESI-MS, and hydrolysis. Their cytotoxic activities toward human hepatoma Bel-7402 cells, human colon carcinoma LoVo cells, and human non-small-cell lung cancer NCIH-460 cells were evaluated by MTT assay, respectively.     

New cycloartane glycosides from the aerial part of Thalictrum fortunei

Four new cycloartane glycosides, 3-O-β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 4)-β-d-fucopyranosyl (22S,24Z)-cycloart-24-en-3β,22,26-triol 26-O-(6-O-acetyl)-β-d-glucopyranoside (1), 3-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 4)-β-d-fucopyranosyl (22S,24Z)-cycloart-24-en-3β,22,26-triol 26-O-(6-O-acetyl)-β-d-glucopyranoside (2), 3-O-β-d-glucopyranosyl (24S)-cycloartane-3β,16β,24,25,30-pentaol 25-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside (3) and 3-O-β-d-glucopyranosyl (24S)-cycloartane-3β,16β,24,25,30-pentaol 25-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranoside (4), were isolated from the aerial parts of Thalictrum fortunei. Their structures were established on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis.     

Two new steroidal saponins from Tribulus terrestris

Two new steroidal saponins and two known flavonoid glycosides were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic analysis and chemical reaction as 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-12-one-3β,22α,26-triol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (1), 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-22-methoxy-2α,3β,26-triol-3-O-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (2), kaempferol-3-gentiobioside (3), and isorhamnetin-3-gentiobioside (4).     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

Two new triterpene saponins from Lysimachia capillipes

Two new saponins, capilliposide G (1) and capilliposide H (2), were isolated from the whole plants of Lysimachia capillipes. Their structures were determined by 1D and 2D NMR, MS technique and chemical methods.     

Two new triterpenoid saponins from Ardisia crenata

Two new triterpenoid saponins, ardisicrenoside K (1) and ardisicrenoside L (2), have been isolated from the roots of Ardisia crenata Sims. Their structures have been determined as 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16-oxo-30,30-dimethoxyoleanane and 3beta-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16alpha,20-dihydroxyoleanane by means of chemical evidences and spectral analysis. Their weak anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae was evaluated in vitro.     

Two new triterpenoid saponins from Ardisia crenata

Two new triterpenoid saponins, ardisicrenoside K (1) and ardisicrenoside L (2), have been isolated from the roots of Ardisia crenata Sims. Their structures have been determined as 3β-O-{α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-13β,28-epoxy-16-oxo-30,30-dimethoxyoleanane and 3β-O-{β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-13β,28-epoxy-16α,20-dihydroxyoleanane by means of chemical evidences and spectral analysis. Their weak anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae was evaluated in vitro.     

Two new triterpene saponins from Lysimachia capillipes

Two new saponins, capilliposide G (1) and capilliposide H (2), were isolated from the whole plants of Lysimachia capillipes. Their structures were determined by 1D and 2D NMR, MS technique and chemical methods.     

Two new furostanol saponins from Tribulus terrestris

Two new furostanol saponins were isolated from the fruits of Tribulus terrestris L. Their structures were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-12-one-3β,26-diol-3-O-β-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2) on the basis of spectroscopic data as well as chemical evidence.     

Two new triterpene saponins from Lysimachia davurica

Two new saponins, named davuricoside L (1) and davuricoside O (2), have been isolated from the whole plants of Lysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

Two new triterpenoid saponins from Symplocos Chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21β-O- cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (1) and 21β-O-cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-(3-O-acetyl)-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.     

Two new triterpenoid saponins from Symplocos chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21beta-O- cinnamoyl-22alpha-O-(2-methylbutanoyl)-15alpha, 16alpha, 28-trihydroxyolean-12-ene-3beta-O-[beta-D-glucopyranosyl (1 --> 2)]-alpha-L-arabinofuranosyl (1 --> 4)-beta-D-glucuronopyranoside (1) and 21beta-O-cinnamoyl-22alpha-O-(2-methylbutanoyl)-15alpha, 16alpha, 28-trihydroxyolean-12-ene-3beta-O-(3-O-acetyl)-[beta-D-glucopyranosyl (1 --> 2)]-alpha-L-arabinofuranosyl (1 --> 4)-beta-D-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3beta,19alpha,20beta-trihydroxyurs-11,13 (18)-diene-28,20beta-lactone-3-O-beta-D-glucopyranosyl (1 --> 3)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-xylopyranoside (1) and 3-O-beta-D-glucopyranosyl (1 --> 3)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-xylopyranosyl-pomolic acid 28-O-beta-D-glucopyranosyl ester (2) by means of spectral and chemical methods.     

Two new triterpene saponins from Lysimachia davurica

Two new saponins, named davuricoside L (1) and davuricoside O (2), have been isolated from the whole plants of Lysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

Two new triterpene saponins from Gynostemma pentaphyllum

Two new dammarane-type triterpene saponins, gypenbiosides A (1) and B (2), were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Their structural elucidations were accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR, HR-TOF-MS, and NMR. The cytotoxic activity was evaluated against one human cancer cell line HL-60 using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.     

Two new triterpenoid saponins from Glochidion puberum

Two new triterpenoid saponins, puberosides A and B, were isolated from the aerial parts of Glochidion puberum. Their structures were elucidated as 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-benzoyloxy-olean-12-ene-16α,28-diol (1) and 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-28-benzoyloxy-olean-12-ene-16α,22α-diol (2) by analysis of their spectroscopic data.     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3β,19α,20β-trihydroxyurs-11,13 (18)-diene-28,20β-lactone-3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranoside (1) and 3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranosyl-pomolic acid 28-O-β-d-glucopyranosyl ester (2) by means of spectral and chemical methods.     

Two new furostanol saponins from Tribulus terrestris L

Two new furostanol saponins, tribufurosides B (1) and C (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D NMR and 2D NMR), the structures of two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-d-galactopyranosyl(1 --> 2)-beta-d-glucopyranosyl(1 --> 2)-beta-d-galactopyranoside (1) and (25S)-5alpha-furost-20(22)-en-12-one-3beta, 26-diol-26-O-beta-d-glucopyranoside (2).     

Two new sulfated oleanan saponins from Achyranthes root

Two new sulfated oleanan saponins, sulfachyranthosides B (1) and D (2), were isolated from a water extract of Achyranthes root (root of Achyranthes bidentata). The structures were determined by analyses of spectroscopic data to be sulfates of achyranthosides B and D, respectively, at the 4′-position of the glucose moiety attached to the C-28 carboxylic acid of oleanolic acid.     

Two new triterpenoid saponins from Caragana microphylla seeds

Two new triterpenoid saponins, caraganins A and B (1 and 2), structurally characterized by a 22-oxo group, were isolated from the seeds of Caragana microphylla Lam., together with their n-butyl esters as artifacts (1a and 2a). Their structures and configurations were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. Compounds 1a and 2a exhibited potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration values ranging from 3.125 to 6.25 μg/ml.