Oleanane-triterpene Saponins from Clinopodium urticifolium

Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 1; 3B, 16B, 21B, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 2; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]-B-D-fucopyranoside 3; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-gluco-pyranosyl-(1-4)-B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]- B-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.

A new dammarane-type triterpene saponin from Gynostemma pentaphyllum

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.

A new triterpene saponin from Panax japonicus C.A.Meyer var major(Burk.) C.Y.Wu et K.M.Feng

One new Iriterpene saponin was isolated from Panaxjaponicus C. A. Meyer var major （Burk.） C. Y. Wu et K. M. Feng, and established as oleanolic acid 3-O-[β-D-glucopyranosyl-（1 →2）-β-D-glucuronopyranosyl-6＇-O-n-butyl ester] which showed mod- erate antitumor activities against the A2780 cells and OVCAR-3 cells. Its structure was established by means of spectral data, particularly NMR, including HSQC and HMBC techniques.

Antiglycation,antioxidant,antiacne,and photoprotective activities of crude extracts and triterpene saponin fraction of Sapindus saponaria L.fruits:An in vitro study

Objective:To evaluate the photoprotective,antioxidant,antiglycation,and antiacne activities of crude extract(CESs)and triterpene saponin fraction(TSSs)of Sapindus saponaria.Methods:HPLC-MS purification was performed on a Symmetry TM C18 column.The saponins were identified by a UV detector.Antioxidant activity was evaluated by DPPH and O_(2)^(−)radicals scavenging,and FRAP and TBARS assays.Glycation activity was assessed by relative electrophoretic mobility and inhibition of advanced glycation end products(AGEs)formation.Additionally,antiacne activity was determined by inhibition of Cutibacterium acnes,and photoprotective effect was evaluated by Mansur’s method.Results:Most of the triterpene saponins detected in the fraction by HPLC-MS analysis were hederagenin as the aglycon.CESs and TSSs presented varying antioxidant activity in DPPH(CESs:75.69%and TSSs:83.65%),FRAP(CESs:425.39μM TE/g DW and TSSs:649.36μM TE/g DW),TBARS(CESs:42.96%and TSSs:52.16%)and O_(2)^(−)radicals scavenging(CESs:61.33%and TSSs:86.69%)tests.CESs and TSSs also exhibited antiglycation activity comparable to bovine serum albumin treated with aminoguanidine.In addition,CESs and TSSs showed inhibition of AGE formation(34.48%and 61.85%,respectively).Antiacne activity against Cutibacterium acnes was observed with a minimum inhibitory concentration equal to minimum bactericidal concentration(CESs:36.11µg/mL and TSSs:18.34µg/mL).In photoprotective assays,CESs and TSSs showed maximum absorbance of 1.42 to 0.20 and 2.80 to 1.30,respectively,in the wavelength range of 260 to 400 nm.Furthermore,CESs and TSSs showed sun protection factors of 8.89 and 14.89,respectively.Conclusions:Sapindus saponaria fruit extracts show strong antioxidant potential and antiglycation activity against bovine serum albumin glycation and AGE formation.Besides,they presented antibacterial activity against Cutibacterium acnes and photoprotective effect against UV-A and UV-B.

Inhibition of DNA-Topoisomerase I by Acylated Triterpene Saponins from Pittosporum angustifolium Lodd.

Previous phytochemical investigation of the leaves and seeds of Pittosporum angustifolium Lodd.led to the isolation and structural elucidation of polyphenols and triterpene saponins.Evaluation for cytotoxicity of isolated saponins revealed that the predominant structural feature for a cytotoxic activity are acyl substituents at the oleanane aglycon backbone.The present work reports the results of a screening of 10 selected acylated saponins for their potential to inhibit the human DNA-topoisomerase I,giving rise to IC50 values in a range of 2.8-46.5 lM.To clarify the mode of observed cytotoxic action and,moreover,to distinguish from a pure surfactant effect which is commonly accompanied with saponins,these results indicate an involvement of the topoisomerase I and its role as a possible target structure for a cytotoxic activity.In addition,computational predictions of the fitting of saponins to the topoisomerase I-DNA complex,indicate a similar binding mode to that of clinically used topoisomerase I inhibitors.Graphical Abstract Ten acylated triterpene saponins from Pittosporum angustifolium were investigated for their potential to inhibit the human DNA-topoisomerase I and computational predictions of the fitting of saponins to the topoisomerase I-DNA complex were carried out.

Antitumor triterpene saponins from Anemone flaccida

A new triterpenoid saponin, 3-O-[（6′-butyryl）-β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-（1→4）-β-D-glucopyranosyl-（1→6）-β-D-glucopyranosyl] oleanolic acid, as well as three known triterpenoid saponins were isolated from the rhizomes of Anemone flaccida. Their structures were elucidated by spectroscopic methods. These compounds showed significant antitumor activities.

A NEW TRITERPENE SAPONIN FROM THE STEMS AND LEAVES OF PANAX GINSENG

a new triterpene compound was isolated from the stems and leaves of Panax ginseng C. A. Meyer and established as 3β, 6α, 12β-trihydroxy-dammar-20(21), 24-diene-6-0-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside on the basis of spectral analysis and chemical evidence.

A New Triterpene Saponin from Gynostemma pentaphyllum

Objective To study the triterpene saponins from Gynostemma pentaphyllum with antitumor activities. Methods The 75% EtOH extract of G. pentaphyllum was used for isolation by silica gel column chromatography and preparative HPLC. The structures of pure compounds isolated were identified by the spectral analysis and chemical evidence. Results Two compounds were isolated and identified as 23(S)-3β,20ξ,21ξ-trihydroxy-19-oxo-21,23- epoxydammar-24-ene 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-xylopyranosyl (1→3)]-β-D-arabinopyranoside (1) and 23(S)-21(R)-O-n-butyl-3β,20ξ-dihydroxy-21,23-epoxydammar-24-ene 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-xylo- pyranosyl (1→3)]-β-D-arabinopyranoside (2). Conclusion Compound 2 is a new triterpene saponin with moderate antitumor activities against the HL-60, Colon205, and Du145 cell lines.

Triterpene saponins with XOD inhibitory activity from the roots of Ilex pubescens

A new triterpene saponin with 28-nor-urs-12（13）,18（17）-dien-3β-ol as aglycone,named ilexsaponin C（1） was isolated from the roots of Ilex pubescens,together with three known saponins 2,3 and 4.The structure of 1 was elucidated on the basis of spectral analysis including 1D and 2D NMR and HR-ESI-MS.Saponins 1 and 4 exhibited significant XOD inhibitory activity in the test.

Two Novel Antifungal Saponins from Tibetan Herbal Medicine Clematis tangutica

Antifungal assay-guided isolation of the ethanol extract of the aerial parts of Clematis tangutica yielded two novel triterpene saponins. Their structures were determined to be 3-O-a-L-arabinopyranosyl hederagenin 28-O-a-L-rhamnopyranosyl ester (1) and 3-O-b-D- glucopyranosyl(14)-a-L-arabinopyranosyl hederagenin 28-O-a-L-rhamnopyranosyl ester (2) on the basis of spectral data and chemical reactions.

Two new saponins from the aerial part of Astragalus membranaceus var. mongholicus

Two new saponins named mongholicoside A （1） and mongholicoside B （2） were isolated from the aerial part of Astragalus membranaceus var mongholicus. Their structures were determined by 1D and 2D NMR, ESI-MS techniques and chemical methods.

Two Novel Saponins from Lysimachia capillipes

Two new saponins named capilliposide C 1 and capilliposide D 2 were isolated from the whole plants of Lysimachia capillipes, their structures were deternuned by 1D and 2D NMR, ESIMS techniques, and chemical methods.Capilliposide C showed significant cytotoxic activity against human A2780 cells.

Two New Saponins from Lysimachia davurica

Two new saponins named davuricoside I (1) and davuricoside E (2) were isolated fromthe whole plants of Lysimachia davurica. Their structures were determined by 1D and 2D NMR,FAB-MS techniques, and chemical methods.

Triterpenoid saponin biosynthesis genes and their expression patterns during the development of sea cucumber Apostichopus japonicus

Sea cucumbers are echinoderm species with a leathery skin and an elongated body.Natural compounds,including saponins,have been previously isolated from sea cucumber.The majority of saponins derived from this organism typically belong to the triterpene glycosides,which exhibit various biological effects(e.g.,antifungal,cytotoxic,hemolytic,and cytostatic immunomodulatory activities).In the present study,30 saponin biosynthesis enzymes,namely 2 AACTs,2 FPSs,2 HMGSs,2 OSCs,1 SS,2 SEs,and 19 UGTs,were found in the genome of sea cucumber Apostichopus japonicus.Compared with upstream saponin biosynthesis enzymes(i.e.,AACTs,FPSs,HMGSs,OSCs,and SSs),the downstream saponin biosynthesis enzymes(SEs and UGTs)shared lower amino acid sequence similarity with the corresponding genes in other echinoderms.It was proposed that the enzyme structures comprised bothα-helices andβ-sheets.Notably,only a low percentage ofβ-sheets were present in FPSs,OSCs,and SS.The saponin biosynthesis enzymes showed dynamic expression patterns during five critical developmental stages of A.japonicus(fertilized oocytes,blastula,gastrula,doliolaria,and penractula).The present study involved elucidation of putative saponin biosynthesis pathways in sea cucumber and provides a valuable platform for further investigation of saponin biosynthesis in echinoderms.

Anti‑inflammatory and Cytotoxic Triterpenes from the Rot Roots of Panax notoginseng

Four new protopanaxatriol-type triterpenes(1-2)and glucosides(3-4),were isolated from the rot roots of Panax notoginseng(Burk.)Chen,along with four known ones(5-8).Their structures were elucidated on the basis of extensive spectroscopic analysis(HRESIMS,NMR,UV,IR,and OR)and acidic hydrolysis.The possible transformation pathway of these compounds were also speculated from ginsenoside Rg_(1).Compound 1,with a uniqueα,β-unsaturated ketene in its side chain,showed significant inhibitory effects against NO production on Murine macrophage cells(IC_(50)=4.12±0.20μM)and comparable cytotoxicities against five human cancer cell lines(myeloid leukemia HL-60,lung cancer A-549 cells,hepatocellular carcinoma SMMC7721,breast cancer MCF-7,and colon cancer SW480)to positive control,cisplatin(DDP).

Licorice and its main components on the treatment of diabetes and its complications:A review of in vivo and in vitro studies

Licorice is one of the oldest herbal medicines for its various ethno pharmacological uses.In both Asian and European countries,it has been recorded for treatment of inflammatory diseases.A large number of ingredients have been isolated from licorice,including triterpene saponins and flavonoids,which are normally being considered to be the main biologically active components.In the last decade,licorice has been proved exert anti-diabetic effect in various in vivo and in vitro models of diabetes mellitus.Furthermore,licorice can also antagonize all sorts of diabetes complications,including diabetic nephropathy,atherosclerosis,diabetic retinopathy and neuropathy.Except anti-inflammation,licorice and its active components show anti-diabetic effects by improving insulin resistance and increasing insulin secretion,regulating lipid metabolism,and anti-oxidation.The useful effects of licorice and its active components are due to regulating different pathways and proteins,including NF-κB,AMPK,insulin signaling pathway,MAPK,etc.In this review,we provide an overview of the beneficial effects and related molecular mechanism of licorice and its effective components on improving diabetes and its complications.

New Cytotoxic Saponins from Lysimachia davurica Ledeb.

To investigate the saponins from whole plants of Lysimachia davurica Ledeb., two new saponins named davuricoside I （compound 1） and E （compound 2） were isolated. Their chemical structures were elucidated as 3β, 16α, 28, 29-tetrihydroxy-olean-12-en-3-O-β-D-glucopyranosyl-（1→2）-β-D-glucuronopyranoside （compound 1） and 3β, 16α, 29-trihydroxy-13, 28-epoxy-oleanane-3-O-β-D-glucopyranosyl-（1→2）-β-D-glucuronopyranoside （compound 2） on the basis of their one- and two-dimensional nuclear magnetic resonance and mass spectrometry data, and chemical methods. Compound 1 showed significant cytotoxic activity against human A2780 cells.

Two New Saponins from Lysimachia capillipes Hemsl.

To investigate the saponins from whole plants of Lysimachia capilUpes Hemsl., two new saponins, named capilliposide E （1） and capilliposide F （2）, were isolated. The structures of the new saponins were elucidated as 3β, 22α-dihydroxy-16α-acetat-28→ 13-lactone-oleanane-3-O- [β-D-glucopyranosyl- （1 →2）-α-L-arabinpyranoyl]-22-O-β-D-glucopyranoside （1） and 3β, 22α-dihydroxy- 16α-acetat-28→ 13-lactone-oleanane-3-O-{ [β-D-glucopyranosyl-（1→2）-β-D-glucopyranosyl-（1→4）]-α-L-arabinpyranoyl}-22-O-β- D-glucopyranoside （2）. The structures of these compounds were determined by 1D- and 2D-NMR, MS techniques, and chemical methods.

Simultaneous analysis of 12 bioactive constituents in Gegen Qinlian pill by HPLC-DAD

In this study, a novel and simple high performance liquid chromatography with diode array detection （HPLC-DAD） method for the simultaneous qualitative and quantitative determination of 12 bioactive components in Gegen Qinlian pill was developed. The separation was performed on a Kromasil C18 column （250 mm×4.6 ram, 5.0 μm） by gradient elution with acetonitrile and 0.02 mol/L ammonium acetate （containing 0.3% triethylamine, and adjusted pH to 4.3 using 1% glacial acetic acid） as the mobile phase at a flow rate of 0.7 mL/min. Three different detection wavelengths （250, 280, 346 nm） were set at the maximum UV absorption wavelengths of these components. Twelve components （puerarin, daidzin, baicalin, wogonoside, liquiritin, berberine, palmatine, jatrorrhizine, glycyrrhizin, baicalein, wogonin and daidzein） were identified and determined using the developed method. All calibration curves showed good linear regression （r〉0.9995） within tested ranges. The injection precision, intra-day precisions and analysis repeatability were evaluated with the RSD values, which were no more than 0.97%, 1.69% and 1.71%, respectively. The recoveries were ranged from 97.4% to 100.2% with RSD values less than 1.87%. This readily available, low-cost and reliable HPLC-DAD method would improve the quality control of Gegen Qinlian pill.