Triterpenoid saponins from the buds of Lonicera similis

Four new lupane triterpenoid saponins, along with one known lupane and eight hederagenin saponins, were isolated from the EtOH extract of the buds of Lonicera similis Hemsl. The structures of the new compounds were established as 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside A, 1), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (lonisimilioside B, 2), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl betulinic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (lonisimilioside C, 3) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl betulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside D, 4), respectively. The cytotoxic activities of the isolates against human cancer cell lines HepG2, MCF-7 and A-549 were evaluated. Only the monodesmosidic saponin with a free carboxyl group at C-28 (12) exhibited significant cytotoxicities against HepG2, MCF-7 and A-549 cell lines with the IC₅₀ values of 8.98 ± 0.19, 12.48 ± 0.45 and 11.62 ± 0.54 μM, respectively. Furthermore, Hoechst fluorescence 33342 staining was used to demonstrate that 12 could induce HepG2 and A-549 cells apoptosis significantly.     

Four new dimeric triterpene glucosides from Sanguisorba officinalis

In search for bioactive compounds from the roots of Sanguisorba officinalis L. (Rosaceae), four new dimeric triterpene glucosides, namely sanguidioside A, B, C, and D (1-4) were isolated. Alkaline hydrolysis of 1-2 afforded the corresponding dimeric aglycones (1a and 2a). Meanwhile, a ready intra-molecular transesterification was observed, providing dimeric triterpenes 1b and 2b. Alkaline hydrolysis of the crude dimmeric saponin also provided a new dimeric triterpene, sanguidiogenin (9). The structures of all these compounds are elucidated via spectroscopic and chemical methods, and are further confirmed by the X-ray diffraction analysis of the dimeric aglycone 2a. Compound 3 represents the first dimeric saponin of an oleanolic acid and an ursonic acid derivative, while compound 4 is the first dimeric saponin of oleanolic acid derivatives.     

Simultaneous determination of 12 active components in the roots of Pulsatilla chinensis using tissue‐smashing extraction with liquid chromatography and mass spectrometry

Ultra high performance liquid chromatography coupled with mass spectrometry and combining a tissue‐smashing extraction technique was developed for the simultaneous quantitative analysis of 12 compounds in the roots of Pulsatilla chinensis . Among them, compound 6 was characterized and accurately quantified in this herb for the first time. The parameters of extraction condition were simultaneously optimized with a Box–Behnken design and Derringer's function. The optimized conditions were as follows: sample quantity of 0.5 g, ethanol concentration of 70%, and extraction time of 200 s. Multiple‐reaction monitoring scanning was employed for the quantification between positive and negative mode in a single run of 6 min. Full validation of the method was carried out, and the results indicated that the method was rapid, specific, and reliable. The developed method was successfully applied to quantify the 12 compounds in 33 batches of P. chinensis from different provinces. Moreover, the principal component analysis was performed to compare the P. chinensis collected from different provinces of China based on quantitative data and the results indicated that the content of compounds could be used to differentiate the origins of P. chinensis . These results demonstrated that this method is feasible and reliable for the quality control of P. chinensis .     

Two new triterpenoid saponins from Polygala crotalarioides

<正>Two new oleanane-type saponins,crotalarioside A(1) and crotalarioside B(2),were isolated from the roots of Polygala crotalarioides.Their structures were elucidated on the basis of spectroscopic and chemical evidence.     

A New Triterpenoid Oligoglycoside Escin IVe from the Seeds ofAesculus Chinensis

Inthecourseofourstudiesonnewbiologicallyactivesaponinsofnaturalmedicines,wehaveisolatedescinsla.fo.IVa.IVb,IVc,andIVdtyolnseedsof.4e'v"11/llSchinensisBee.(Hippocastanaceae),andsinglecrystalX-raydiffractionanalysiswasundertakenonescinla'.whichconfirmstheabsoluteconfigurationandsugarsequence.ThepresentpaperdescribesthestructuredeterminationofanewtriterpenoidsaponinnamedescinIVefromthesameplant.EscinIVe,whitepowder.Positive-modeTOF-MScm/zI111[M Na] ,coupledwitllNMRdata.correspondstoane…     

Spirostanol Saponins from the Fibrous Roots of Ophiopogon japonicus (Thunb.) Ker‐Gawl

Three new steroidal saponins, (25R)‐ruscogenin‐3‐yl α‐L ‐rhamnopyranosyl‐(1→2)‐[β‐D ‐xylopyranosyl‐(1→4)]‐β‐D ‐glucopyranoside ( 1 ), diosgenin‐3‐yl 2‐O‐acetyl‐α‐L ‐rhamnopyranosyl‐(1→2)‐[β‐D ‐xylopyranosyl‐(1→4)]‐β‐D ‐glucopyranoside ( 2 ), and pennogenin‐3‐yl 2‐O‐acetyl‐α‐L ‐rhamnopyranosyl‐(1→2)‐[β‐D ‐xylopyranosyl‐(1→4)]‐β‐D ‐glucopyranoside ( 3 ) were isolated from the fibrous roots of Ophiopogon japonicus (Thunb .) Ker‐Gawl . Their structures were determined by spectroscopic methods including IR, HR‐ESI‐MS, and 1D‐ and 2D‐NMR. All of these three steroidal saponins exhibited weak cytotoxicities against Hela and Hep2 cell lines.     

Complete 1H- and 13C NMR assignments of saponins from roots of Gypsophila trichotoma Wend

The assignments of 1H and 13C NMR spectra of two new aminoacyl triterpene saponins from roots of Gypsophila trichotoma Wend. are reported. In addition to 1D NMR methods, 2D NMR techniques (COSY, TOCSY, ROESY, HSQC, HMBC, and HSQC-TOCSY) were used for the assignments. The structures were completed by analysis of HR-ESI-MS and ESI-MS(n).     

Medicinal Flowers. Part 29. Acylated Oleanane‐Type Triterpene Bisdesmosides: Perennisaponins G,H, I,J, K,L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis

The MeOH extract from the flowers of Bellis perennis was found to show pancreatic‐lipase inhibitory activity (IC₅₀ 455 μg/ml). From the extract, seven new triterpene saponins named perennisaponins G ( 1 ; IC₅₀ 163 μM ), H ( 2 ; 137 μM ), I ( 3 ; 147 μM ), J ( 4 ; 148 μM ), K ( 5 ; 223 μM ), L ( 6 ; 81.4 μM ), and M ( 7 ; 195 μM ) were isolated as pancreatic lipase inhibitors. The stereostructures of 1 – 7 were elucidated on the basis of chemical and spectroscopic evidence.     

New triterpenoid glycosides fromThalictrum minus L.

Two triterpenoid diglycosides of the cycloartane series were isolated from the terrestrial part ofThalictrum minus L. (Ranunculaceae). Genins of these glycosides are side-chain structural isomers—3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20(S)-lanost-24(Z)-ene-3β, 16β, 22(S), 26, 29-pentaol and 3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20(S)-lanost-25-ene-3β, 16β,22(S), 24ζ, 29-pentaol. The structures of these glycosides were established using 1D and 2D NMR spectroscopy and FAB mass spectrometry. For Part 9, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1434–1437, July, 1998.     

Synthesis of pennogenyl saponin analogs using three methods

The synthesis of pennogenyl saponins and related compounds using three popular methods of glycosylation has been reported for the first time. Glycosyl halides, glycosyl trichloroacetimidates, and thioglycosides were used as glycosyl donors in the reactions with pennogenin as the glycosyl acceptor. The reactions occur selectively with the C(3)OH group due to the difference in steric accessibility of the hydroxyl groups at the C(3) and C(17) atoms of pennogenin. This makes it possible to synthesize a series of pennogenyl saponins without C(17)OH group protection. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1789–1792, October, 2006.