Two New Tirucallane-Type Triterpenoid Saponins from Sapindus mukorossi

Two new tirucallane-type triterpenoid saponins, Sapimukoside A (1) and Sapimukoside B (2), were isolated from the roots of Sapindus mukorossi Gaertn. On the basis of spectroscopic and chemical evidence, their structures were elucidated to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (2).

New Triterpenoid Saponins from Polycarpon prostratum (Caryophyllaceae)

Three new triterpenoid saponins, namely prostratosides A-C (1-3), were isolated from the whole plant of Polycarpon prostratum (Forssk.) Aschers. et Schwein. ex Aschers. By spectroscopic methods, their structures were determined as 3_O_{β_D_xylopyranosyl_(1→2)_β_D_glucopyranosyl_(1→4)_[β_D_glucopyranosyl_(1→2)]_α_L_arabinopyranoside}_22α_acetoxy_saikogenin G, 3_O_{β_D_xylopyranosyl_(1→2)_β_D_glucopyranosyl_(1→4)_[β_D_glucopyranosyl_(1→2)]_α_L_arabinopyranoside}_16α_hydroxy_22α_acetoxy_saikogenin E and 3_O_{β_D_xylopyranosyl_(1→2)_β_D_glucopyranosyl_(1→4)_[β_D_glucopyranosyl_(1→2)]_α_L_arabinopyranoside}_21β_acetoxy_saikogenin G, respectively.

Antioxidant,antimicrobial,and α-glucosidase inhibitory activities of saponin extracts from walnut(Juglans regia L.) leaves

Objective:To investigate the relationship between triterpenoid saponin content and antioxidant,antimicrobial,and α-glucosidase inhibitory activities of 70%ethanolic,butanolic,aqueous,supernate and precipitate extracts of Juglans regia leaves.Methods:Triterpenoid saponins of different Juglans regia leaf extracts were measured by the vanillin method.Antioxidant activity was evaluated against DPPH and ABTS free radicals.We also assessed α-glucosidase inhibitory and antimicrobial activities of the leaf extracts.Pearson’s correlation coefficient was evaluated to determine the correlation between the saponin content and biological activities.Results:The butanolic extract was most effective against DPPH with an IC50of 6.63μg/mL,while the aqueous extract showed the highest scavenging activity against ABTS free radical with an IC50of 42.27μg/mL.Pearson’s correlation analysis indicated a strong negative correlation (r=-0.956) between DPPH radical scavenging activity (IC50) and the saponin content in the samples examined.In addition,the aqueous extract showed the best α-glucosidase inhibitory activity compared with other extracts.All the extracts had fair antibacterial activity against Bacillus subtilis,Escherichia coli,and Klebsiella pneumoniae except for the aqueous extract.Conclusions:Juglans regia extracts show potent antioxidant,antimicrobial,and α-glucosidase inhibitory activities.There is a correlation between saponin levels in Juglans regia leaf extracts and the studied activities.However,additional research is required to establish these relationships by identifying the specific saponin molecules responsible for these activities and elucidating their mechanisms of action.

Adjuvant effects of saponins on animal immune responses

Vaccines require optimal adjuvants including immunopotentiator and delivery systems to offer long term protection from infectious diseases in animals and man. Initially it was believed that adjuvants are responsible for promoting strong and sustainable antibody responses. Now it has been shown that adjuvants influence the isotype and avidity of antibody and also affect the properties of cell-mediated immunity. Mostly oil emulsions, lipopolysaccharides, polymers, saponins, liposomes, cytokines, ISCOMs (immunostimulating complexes), Freund’s complete adjuvant, Freund’s incomplete adjuvant, alums, bacterial toxins etc., are common adjuvants under investigation. Saponin based adjuvants have the ability to stimulate the cell mediated immune system as well as to enhance antibody production and have the advantage that only a low dose is needed for adjuvant activity. In the present study the importance of adjuvants, their role and the effect of saponin in immune system is reviewed.

A new triterpenoid saponin from the roots of Platycodon grandiflorum

A new triterpenoid saponin, 3-O-β-D-glucopyranosyl 16-oxo-platycodigenin 28-O-β-D-apiofuranosyl-（1 → 3）-β-D-xylopyra- nosyl-（1→4）-α-L-rhamnopyranosyl-（1 → 2）-α-L-arabinopyra-nosyl ester, was isolated from the roots of Platycodon grandiflorum, together with three known saponins, including platycodin D, deapio platycoside E and platycoside E. The structure of the new compound, named 16-oxo-platycodin D, was elucidated on the basis of spectroscopic data.

Two New Oleanene-Type Triterpenoid Saponins from Pueraria peduncularis

From the radix of Pueraria peduncularis Grah., two new oleanene-type triterpenoid saponins named pedunsaponins B (2) and C (3) were isolated. Their structures were determined as 3-O-(6-O-methyl)-beta-D-glucuronopyranosyl-3 beta.15 alpha-diol-12-oleanene-16-one (2) and 3-O-beta-D-glucopyranosyl-( 1 --> 3)-beta-D-glucuronopyranosyl-3 beta, 15 alpha-diol-12-oleanene-16-one (3) on the basis of spectroscopic evidence and chemical reactions.

Cytotoxic triterpenoid saponins from Ardisia pusilla

A new triterpenoid saponin, 3-O-{ β-D-xylopyranosyl-（1 → 2）-β-D-glucopyranosyl-（1 → 4）-[β-D-glucopyranosyl-（1 → 2）]-α- L-arabinopyranosyl}-3β,16α,28α-trihydroxy-13β,28-epoxy-oleanan-30-al （ardipusilloside Ⅲ, 1）, together with two known saponins, ardisiacrispins A （2） and B （3）, were isolated from the whole plants of Ardisia pusilla A. DC. Their structures were elucidated by extensive spectral analysis and chemical evidences. Saponins 1 and 3 exhibited significant cytotoxicity against human glioblastoma U251MG cells.

Two new triterpenoid saponins from Rhaponticum uniflorum

Two new triterpenoid saponins were isolated from the roots ofRhaponticum uniflorum. Their structures were elucidated as 3-O- [β-D-glucopyranosyl]-ilexolic acid-28-O-[β-D-glucopyranosyl] ester 1 and 3-O-[β-D-glucopyranosyl]-urs-12, 19 （29）-dien-oic acid-28-O-[β-b-glucopyranosyl] ester 2 mainly by 1D, 2D NMR techniques and chemical methods.

Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida

To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes,a phytochemical study of Cimicifuga foetida was conducted.113 g(0.17%)actein was purified by recrystallization while eight cycloartane-type triterpenes(1-8)were isolated from the mother liquid.The chemical structures of new compounds(1-4)were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses.Moreover,new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC_(50) values ranging from 4.02 to 15.80μM.

Triterpenoid Saponins from the Seeds of Aesculus chinensis and Their Cytotoxicities

Six new triterpenoid saponins,aesculusosides A-F(1-6),together with 19 known ones,were isolated from the seeds of Aesculus chinensis.The new structures were elucidated through extensive spectroscopic analyses and by comparison with previously reported data.Some of the isolates were evaluated for their cytotoxic activities against MCF-7 cell line by an MTT assay,and compounds 15,16,19,and 23-25 exhibited inhibitory activities against MCF-7 with IC50 values ranging from 7.1 to 31.3μM.

Triterpenoid Saponins from Clematis tangutica

Two new triterpenoid saponins, tanguticoside A and B were isolated from aerial part of Clematis tangutica. Their structures were elucidated as 3-O-beta-D-glucopyranosyl hederagenin 28 O-alpha-L-rhamnopyranosyl- (1-->4)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosidel and 3-O-beta-D-glucopyranosyl ranosyl- (1-->2)-beta-D-glucopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl- (1-->4)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranoside2, respectively.

Three New Triterpenoid Saponins from the Seeds of Aesculus chinensis

Three new triterpenoid saponins, escins IVc (1), IVd (2) and IVf (3) were isolated from the seeds of Aesculus chinensis. They were. determined as 22 alpha-tigloyl-28-acetylprotoaescigenin-3 beta-O- [beta-D-glucopyranosyl (1-->2)] [beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranosiduronic acid 1, 22 alpha-angeloyl-28-acetylprotoaescigenin-3 beta-O- [beta-D-glucopyranosyl (1-->2)] [beta-D-glucopyrano- syl (1-->4)]-beta-D-glucopyranosiduronic acid 2 and 28-tigloyl protoaescigenin-3 beta-O- [beta-D-gluco-pyranosyl (12)] [beta-D-glucopyranosyl (1-->4)] -beta-D-glucopyranosiduronic acid 3.

ASTERYUNNANOSIDE A AND B，TWO NEW TRITERPENOID SAPONINS FROM ASTER YUNNANENSIS FRANCH

Two new oleanane-type triterpenoid saponins.sateryunn3noside A and B,were isolated from the roots of Aster yunnanensis Franch,and their Structures were elucidated based on spectral evidence and chemical hydrolysis. They have the same aglycone,Which has been assigned as 2a,3 .23-trihydroxyolean-12-en-28-cio acid,and the deference consisted only in 28-O-linked sugar moieties. Asteryunnanoside A is a 28-O-a-L-rhamnopyranosyl-(1-2)- -D-glucopyranoside and B is 28-O- -D-glucopyranosyl-(1 -2),-D-glucopyranoside of the corresponding aglycone.

Triterpenoid Saponins from Tu Jia Ethnomedicine Bai San Qi and Their Cytotoxicity on Hep G2 and BGC-823 Cell Lines

Objective Tu Jia ethnomedicine is a unique medical system inherited and adhibited by Tu Jia minority living in central-south China. Panax japonicus C. A. Mey.(Bai San Qi,白三七) is recognized as an effective and rare medicinal plant to treat weakness, fatigue and rheumatism in Tu Jia ethnomedicine. This paper is to discover more substance evidence for the application of Tu Jia ethnomedicine. Methods Column chromatography and preparative high performance liquid chromatography (HPLC) was applied for isolation and purification;1H-NMR, 13C-NMR, 1H-1H COSY, HSQC and HMBC NMR spectra were applied for structure identification;Methyl thiazolyl tetrazolim (MTT) assays were applied for cytotoxicity evaluation. Results Totally 12 known compounds were isolated by column chromatography and preparative HPLC from rhizomes of Panax japonicus C. A. Mey.(Bai San Qi,白三七). Structures of these compounds were identified by their NMR spectra. All the 12 compounds were triterpenoid saponins. Five of them were oleanolic acid type, and the remaining 7 were dammarane type. Eleven compounds were assayed for their cytotoxic activity against Hep G2 human liver cancer cell lines and BGC-823 human gastric cancer cell lines. Three of the 11 showed relatively dominant cytotoxicity against these cell lines. Conclusions A total of 12 known compounds have been identified from Panax japonicus C. A. Mey.(Bai San Qi,白三七);NMR spectra of compounds with similar skeletons showed regular characteristics;3 compounds showed relatively dominant cytotoxicity against Hep G2 and BGC-823 cancer cell lines, and the result can be valued as weak while setting the taxol as a positive control.

TWO NEW TRITERPENOID SAPONINS，ASTERBATANOSIDE B AND C FROM ASTER BATANGENSIS

Two new oleanane-type triterpenoid saponins, asterbatanoside B and C have been isolated from the roots of Aster batsngensis and their structures elucidated as -2a, 3P, 23-trihydroxyolean-12-en-28-cio acid -28-O-β-D-glucopyranosyl-(1-6) β-Dglucopyranoside and 3-O-β-D-glucopyrsnosyl-2D, 3β, 23-trihydroxyolean-12-en-28-oicacid-28-O-β-D-glucopyranoside by means of spectral data and chemical evidence.

TWO NEW TRITERPENOID SAPONINS，ASTERBATANOSIDE D ANDE，FROM ASTER SATANGENSIS

Two new triterpenoid saponins named asterbatanoside D and E have been isolated from Aster batgngensis and their structures elucidated as 3-O-β-D-glucopyranosyl-bayogenin-28-O- β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside and 3-O-6'-acetyl-β-D-glucopyranosyl-bayogenin-28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl. based on MS, 1D and 2D NMR techniques (COSY,TOCSY,ROESY, HMQC and HMBC), and Chemical reactions.

Antitumor Triterpenoid Saponin from the Fruits of Avicennia marina

The fruits of Avicennia marina are widely used for both medicine and food in Guangxi of China.As a part of our continuous effort to search for bioactive molecules from the plant,the fruits of A.marina were investigated,which has led to one new triterpenoid saponin(1)and 29 known compounds been isolated and their structures were established by using spectroscopic methods and comparing with literature data.The new triterpenoid saponin showed cytotoxicity against GSC3#and GSC-18# with the IC50 values were 12.21 and 5.53 μg/mL respectively,and most of the known compounds had significant antioxidant capacity with the IC_(50) values ranging from 0.36 to 13.07 μg/mL.

NEW TRITERPENOIDAL SAPONINS FROM MUSSAENDA PUBESECUS

A cyclolanostene-type triterpene and two saponins derived thereform, namely MP-C,D and F,were isolated from the acid-hydrolyzate of the mixture of saponins of Mussaenda pubesecus.Their structures were elucidated on the basis of chemical and UV,IR,~1H,^(13)C NMR and MS spectral evidence.The two new saponins MP-D and F were named Mussaendoside A and C,respectively.

Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest

Bioassay-guided fractionation of EtOH extracts obtained from the roots and wood of the Madagascan plant Leptaulus citroides Baill.(Cardiopteridaceae)led to the isolation of ethyl esters of three new triterpenoid saponins(1–3)and the known sesquiterpenoid cinnamosmolide(4).The structures of 1–3 were elucidated by extensive 1D and 2D NMR experiments and mass spectrometry.Compounds 1,2,and 4 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line with IC50 values of 2.8,10.2 and 2.0 lM,respectively.

Two New Triterpenoid Saponins from Aster Lingulatus

Two new saponins named asterlingulatosides A and B were isolated from the whole plants of Aster lingulatus. Their structures were elucidated by spectral and chemical evidence as 3-O-beta-D-glucopyranosyl-3 beta, 16 alpha-dihydroxyolean-12-en-28-oic acid -28-O-alpha-L-arabinopyranoside and 3-O-beta-D-glucopyranosyl-3 beta,16 alpha-dihydroxyolean-12-en-28-oic acid -28-O-alpha-L-rhamnopyranosyl-(1-->2)- alpha-L-arabinopyranoside respectively. They showed inhibitory activity on DNA synthesis of human leukemia HL-60 cells.