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).

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.

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.

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.

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.

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.

Steroid and triterpenoid saponins from the rhizomes of Paris polyphylla var.stenophylla

Five new saponins,including three steroid saponins,paristenoids A-C(1-3),and two triterpenoid saponins,paristenoids D-E(4-5),along with four known ones(6-9)were isolated from the rhizomes of Paris polyphylla var.stenophylla.The structures of the isolated compounds were identified nainly by detailed spectroscopic analysis,including extensive 1D and 2D NMR,MS,as well as chemical methods.Compound 3 is a new cyclocholestanol-type steroidal saponin with a rare 6/6/6/5/5 fused-rings cholestanol skeleton,and this skeleton has been first found from the genus Paris.The cytotoxicities of the isolated compounds against three human three glioma cell lines(U87MG,U251MG and SHG44)were evaluated,and compound 7 displayed certain inhibitory effect with ICso values of 15.22±1.73,18.87±1.81 and 17.64±1.69μmol^(-1),respectively.

Structural determination of two triterpenoid saponins from Gymnocladus chinensis Baill

Two triterpenoid saponins （compound Ⅰ and Ⅱ） have been isolated from Gymnocladus chinensis Baill., and compound Ⅰ was determined as a new compound. The structure of compound Ⅰ was assigned as 2β,23-dihydroxy-acacic acid-3-O-α-L-arabinopyranosyl-21-O-{（6S）-2-E-2,6-dimethyl-6-O-[4-O-（6S）-2-E- 2,6 -dimethyl-6-O-β-D-glucopyranosyl-α-L-arabinopyranosyl-2,7-octadienoyl} -28-O-β-D-xylopyranosyl（ 1 →3 ）-β-D-xylopymnosyl （ 1→4）- α-L-rhamnopyranosyl（1→2）-[α-L-rhamnopyranosyl-（1→6）]-β-D-glucopyranoside by extensive MS and NMR studies.

Simultaneous determination of four triterpenoid saponins and two liganoids in the roots of Ilex pubescens by RP-HPLC-DAD

A reversed-phase high performance liquid chromatography （RP-HPLC） method with diode array detector （DAD） has been established to simultaneously determine six bioactive compounds in the roots ofllex pubescens, namely tortoside A, （＋）-syringaresinol, ilexsaponin B3, ilexsaponin A1, ilexsaponin B1, ilexgenin A. The RP-HPLC assay was performed on a reversed-phase C18 column with a gradient elution. The mobile phase consisted of acetonitrile and water containing 0.1% （v/v） phosphoric acid. The flow rate was 1.0 mL/min and the detection wavelength was set at 210 nm. The six marker constituents were separated well with good linearity （r2〉0.9996）, precision, stability and repeatability. The overall recoveries were in the range of 99.00%-104.52%. Cluster analysis was employed to analyze 15 batches of samples. The result indicated this method provide an efficient way to perform quality control as well as a scientific rationale for the Geo-authentication of I. pubescens.

Advances in biosynthesis of triterpenoid saponins in medicinal plants

In recent years, biosynthesis of triterpenoid saponins in medicinal plants has been widely studied because of their active ingredients with diverse pharmacological activities. Various oxidosqualene cyclases, cytochrome P450 monooxygenases, uridine diphosphate glucuronosyltransferases, and transcription factors related to triterpenoid saponins biosynthesis have been explored and identified. In the biosynthesis of triterpenoid saponins, the progress of gene mining by omics-based sequencing, gene screening, gene function verification, catalyzing mechanism of key enzymes and gene regulation are summarized and discussed. By the progress of the biosynthesis pathway of triterpenoid saponins, the large-scale production of some triterpenoid saponins and aglycones has been achieved through plant tissue culture, transgenic plants and engineered yeast cells. However, the complex biosynthetic pathway and structural diversity limit the biosynthesis of triterpenoid saponins in different system. Special focus can further be placed on the systematic botany information of medicinal plants obtained from omics large dataset, and triterpenoid saponins produced by synthetic biology strategies, gene mutations and gene editing technology.

Triterpenoid saponins and phenylpropanoid glycoside from the roots of Ardisia crenata and their cytotoxic activities

Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods.Compounds 2-7 were evaluated for their cytotoxic activities against A549,MCF-7,HepG2 and MDA-MB-231 cell lines by MTT assay.Ardicrenin(6)showed significant cytotoxicity,with IC50 values of 1.17±0.01,1.19±0.06,3.52±0.23,and 16.61±1.02μmol·L^(-1),respectively.

Triterpenoid saponins from the roots of Cyathula officinalis and their inhibitory effects on nitric oxide production

The present study was designed to investigate the chemical constituents of the roots of Cyathula officinalis. Compounds were isolated by silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. Their structures were determined on the basis of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. One new oleanane-type triterpenoid saponin, 28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranosyl] hederagenin(1), was isolated from the roots of Cyathula officinalis. The anti-inflammatory activities of the isolates were evaluated for their inhibitory effects against LPS-induced nitric oxide(NO) production in RAW 264.7 macrophages cells. Compounds 2, 4, and 6 exhibited moderate anti-inflammatory activities.

Cycloartenol triterpenoid saponins from Cimicifuga simplex(Ranunculaceae) and their biological effects

The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9,19-cyclolanostane triterpenoid glycosides, which are distributed widely in Cimicifuga plants, but not in other members of the Ranunculaceae family, and are considered to be characteristics of the Cimicifuga genus. This type of triterpenoid glycoside possesses several important biological activities. More than 120 cycloartane triterpene glycosides have been isolated from Cimicifuga simplex Wormsk. The aim of this review article is to summarize all the major findings based on the available scientific literatures on C. simplex, with a focus on the identified 9,19-cyclolanostane triterpenoid glycosides. Biological studies of cycloartane triterpene glycosides from Cimicifuga spp. are also discussed.

New triterpenoid saponins from the leaves of Ilex chinensis and their hepatoprotective activity

Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from the leaves of Ilex chinensis.Their structures were elucidated by comprehensive spectroscopic 1 D and 2 D NMR and HR-ESI-MS data.Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization.Compounds 1,2,4,9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol(APAP)-induced Hep G2 cell injury in vitro.

Triterpenoid Saponins from Luculia pincia Hook

Two new triterpenoid saponins,cincholic acid-3- O - β - D -xylopyranoside,28- O - β - D -glucopyranosyl ester (1),quinovic acid-28- O - β - D -glucopyranosyl ester (4),and a new phenolic glucoside,4-[4'- O -( 2',3',5',6'-tetrahydroxy phenyl)- β - D -glucoside]-1-butene (2),along with five known triterpenoid saponins and one phenolic glucoside were isolated from the n -butanol fraction of the stems of Luculia pinciana Hook. Their structures were established by means of spectroscopic methods.