A new triterpenoid saponin from the roots of Ardisia crenata

A new triterpenoid saponin.3 β-O-{ β-D-glucopyranosyl-(1—4)-[ β-D-glucopyranosyl-[1-2)]- α-L-arabinopyranosyl}-16α, 28-dihydroxyolean-12-en-30-oic acid 30-O- β-D-glucopyranosyl ester(ardisicrenoside N.1),together with two known saponins, ardisicrenoside C(2) and D(3),were isolated from the roots of Ardisia crenata Sim.Their structures were elucidated by extensive spectral analysis and chemical evidences.Saponins 1 showed cytotoxicity against MCI-7 and NCI-H460 cancer cell lines at 11.0μmol/L and 22.1μmol/L in vitro.     

Three New Triterpenoid Saponins from Ardisia crenata

Three new triterpenoid saponins, ardisicrenoside I ( 1 ), ardisicrenoside J ( 2 ), and ardisicrenoside M ( 3 ), along with eight known compounds, were isolated from the roots of Ardisia crenata Sims . Their structures were elucidated as 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 1 ), 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 2 ), 30,30‐dimethoxy‐16‐oxo‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 3 ), ardisiacrispin A ( 4 ), ardisiacrispin B ( 5 ), ardisicrenoside B ( 6 ), ardisicrenoside A ( 7 ), ardisicrenoside H ( 8 ), ardisicrenoside G ( 9 ), cyclamiretin A‐3β‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 10 ), and cyclamiretin A‐3β‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 11 ) by means of chemical and spectral analysis, and their cytotoxicities were evaluated in vitro.     

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

Two new lactones, named Ardisicreolides A–B (1–2), together with four known flavonoids, Quercetin (3), Myricetrin (4), Quercitrin (5), Tamarixetin 3-O-rhamnoside (6), were isolated from the ethyl acetate portion of 70% ethanol extracts of dried leaves from Ardisia crenata Sims. These compounds were identified from Ardisia crenata Sims for the first time. The structures of 1–6 were elucidated according to 1D and 2D-NMR methods and together with the published literature. All of the isolated compounds were evaluated for in vitro anti-microbial effect against Escherichia coli, Pseudomonas aeuroginosa, Enterococcus faecalis, Proteus vulgaris, Staphylococcus aureus, and Bacillus subtilis. In addition, compounds 1–2 were assessed for anti-inflammatory activity by acting on LPS-induced RAW 264.7 macrophage cells in vitro. The results showed that only compound 2 exhibited moderate antibacterial activity on Bacillus subtilis. Moreover, compounds 1 and 2 were found to significantly inhibit the production of nitric oxide (NO) and reduce the release of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), interleukin-4 (IL-4), and interleukin-10 (IL-10) in LPS-induced RAW 264.7 macrophage cells. The present data suggest that lactones from the leaves of A. crenata Sims might be used as a potential source of natural anti-inflammatory agents.     

New triterpenoid saponins from the steaming treated roots of Panax notoginseng

Further phytochemical investigation of the steaming treated roots of Panax notoginseng (Araliaceae) led to the identification of two new dammarane-type triterpenoid saponins, notoginsenoside SP20 (1) and SP21 (2). In addition, a pair of new phenolic glycosides (3a and 3b) was also isolated together with two known compounds. Their structures were elucidated by HRESIMS, 1D- and 2D-NMR spectra. Compounds 1 and 2 showed no in vitro cytotoxicity against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-9 and SW480).     

Cytotoxic triterpenoid saponins from Ardisia pusilla

A new triterpenoid saponin,3-O-{β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-ghcopyranosyl-(1→2)]-α-L-arabinopyranosyl }-3β,16α,28α-trihydroxy-1313,28-epoxy-oleanan-30-al(ardipusilloside Ⅲ,1),together with two known sapo-nins,ardisiacrispins A(2)and B(3),were isolated from the whole plants ofArdisia 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.     

Three novel triterpenoid saponins from Lysimachia capillipes and their cytotoxic activities

Three new saponins, capilliposide A (1), capilliposide B (2) and capilliposide C (3) were isolated from an ethanol extract of Lysimachia capillipes. Their structures were determined by 1D and 2D NMR (1H-1H COSY, HMBC, HMQC, DEPT and TOCSY) techniques, MS, and hydrolysis. Capilliposide B showed significant cytotoxicity against human A-2780 cells.     

Ursane-type triterpenoid saponins from Elsholtzia bodinieri

Investigation of the n-BuOH extract of the aerial parts of Elsholtzia bodinieri led to the isolation of two new ursane-type triterpenoid saponins, bodiniosides O (1) and P (2), along with five known saponins, rotungenoside (3), 3,28-O-bis-β-d-glucopyranosides of 19α-hydroxyarjunolic acid (4), oblonganosides I (5), rotungenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (6), and bodinioside M (7) isolated from the species. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-β-d-xylopyranosyl-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-β-d-xylopyranosyl-(1→6)-[β-d-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside and 3-O-β-d-xylopyranosyl-23-hydroxy-urs-12(13)-en-28-oic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside. Compounds 1 and 2 exhibited potent anti-HCV activities in vitro with a selective index of 30.63 and 9.08, respectively.     

Cytotoxic 13,28 Epoxy Bridged Oleanane-Type Triterpenoid Saponins from the Roots of Ardisia crispa

Ardisiacrispin D–F (1–3), three new 13,28 epoxy bridged oleanane-type triterpenoid saponins, together with four known analogues (4–7) were isolated from the roots of Ardisia crispa. The structures of 1–7 were elucidated based on 1D and 2D-NMR experiments and by comparing their spectroscopic data with values from the published literatures. Ardisiacrispin D–F (1–3) are first examples that the monosaccharide directly linked to aglycone C-3 of triterpenoid saponins in genus Ardisia are non-arabinopyranose. In the present paper, all compounds are evaluated for the cytotoxicity against three cancer cell lines (HeLa, HepG2 and U87 MG) in vitro. The results show that compounds 1, 4 and 6 exhibited significant cytotoxicity against Hela and U87 MG cells with IC₅₀ values in the range of 2.2 ± 0.6 to 9.5 ± 1.8 µM. The present investigation suggests that roots of A. crispa could be a potential source of natural anti-tumor agents and their triterpenoid saponins might be responsible for cytotoxicity.     

New triterpenoid saponins from the leaves of Cyclocarya paliurus

Two new secodammarane triterpenoid saponins, cyclocariosides I and J (1 and 2), and a new epoxydammarane triterpenoid saponin, cyclocarioside K (3) were isolated from the ethanol extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic techniques.     

Five new bidesmoside triterpenoid saponins from Stauntonia chinensis

Eleven triterpenoid saponins (1-11) were isolated from Stauntonia chinensis DC. (Lardizabalaceae), including five new compounds, yemuoside YM(21-25) (1-3, 6, 7) structures of which were elucidated by chemical methods and a combination of MS, 1D- and 2D- NMR experiments including DEPT, (1)H--(1)H COSY, HSQC, HMBC, TOCSY, and NOESY as 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-rhamnopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonicacid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-xylopyranosyl-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-akebonic acid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), 3-O-beta-D-glucopyranosyl-(1 --> 3)-alpha-L-arabinopyranosyl-akebonic acid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (3), 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-rhamnopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (6), 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-arabinopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (7).     

Three new oleanane-type triterpenoid saponins from the seeds of Celosia cristata L.

Phytochemical investigation of the 1-butanol soluble fraction of 60% ethanol extract of the seeds of Celosia cristata L. led to the identification of three new oleanane-type triterpenoid saponins. Using ¹D and ²D NMR experiment methods, ESI-MS analysis and acid hydrolysis, their structures were identified as 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl]-2β-hydroxy-oleanolic acid-28-O-β-D-glucopyranoside (1), 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl]-2β, 23-dihydroxy-oleanolic acid-28-O-β-D-glucopyranoside (2) and 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl]-2-hydroxyl-medicagenic acid-28-O-β-D-glucopyranosyide (3), respectively.     

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.     

Two new triterpenoid saponins obtained by microbial hydrolysis with Alternaria alternata AS 3.6872

Compound 1, a triterpenoid saponin from Ardisia gigantifolia Stapf showing potential anti-tumour activity, was hydrolysed into two deglycosyl derivatives (2 and 3) by Alternaria alternata AS 3.6872. Both these derivatives are new compounds. Their structures were elucidated on the basis of 1D, 2D NMR, HR-ESI-MS and optical rotation spectral data. Compounds 1–3 were evaluated for their cytotoxicity against human hepatocellular carcinoma and normal liver cells by Cell Counting Kit 8 colorimetric assay.     

Identification and structural characterisation of triterpene saponins from the root of Ardisia mamillata Hance by HPLC-ESI-QTOF-MS/MS

Triterpene saponins in medicinal plants attract scientific attentions for their structural diversity and significant bioactivities. In this work, a high-performance liquid chromatography coupled to electrospray ionisation and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS/MS) method is used to rapidly separate and identify triterpene saponins from the extract of Ardisia mamillata Hance (AMH). In the full scan mass spectrum, the accurate determination of molecular formula is obtained by the predominant ion [M + HCOO]^? in negative ion mode. As a result, 30 triterpene saponins are identified or tentatively identified in the plant extract. Of these, 17 triterpene saponins are new compounds. In conclusion, the HPLC-ESI-QTOF-MS/MS is an efficient technique to separate and identify triterpene saponins in complex matrices of medicinal plant.     

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 epidioxy-tetracyclic triterpenoid from Poria cocos Wolf

A new epidioxy-tetracyclic triterpenoid, 3-(2-hydroxyacetoxy)-5α, 8α-peroxydehydrotumulosic acid (10), along with nine known compounds were isolated from Poria cocos Wolf (Polyporaceae). Their structures were determined by extensive spectroscopic analyses and comparison with literature data. The cytotoxicity of these compounds against human cancer cell lines MNK-45 was evaluated by MTT method.     

Ardisimamillosides G and H,two new triterpenoid saponins from Ardisia mamillata

Two new triterpenoid saponins, ardisimamilloside G (1), 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16-oxo-oleanan-3beta,30-diol and ardisimamilloside H (2), 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl]-3beta-hydroxy-13beta,28-epoxy-16-oxo-oleanan-30-al, were isolated from the roots of Ardisia mamillata HANCE. Structure assignments were established on the basis of spectral data and chemical evidence.     

One new 19-nor cucurbitane-type triterpenoid from the stems of Momordica charantia

One new 19-nor cucurbitane-type triterpenoid (3β,9β,25-trihydroxy-7β-methoxy-19-nor-cucurbita-5,23(E)-diene) (1), together with other six known cucurbitane-type triterpenoids (2–7), were isolated from the stems of Momordica charantia L. The chemical structure of 1 was elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY and ROESY), MS experiments. Using MTT assay, compound 1 exhibited weak cytotoxicity against HL-60, A-549, and SK-BR-3 cell lines with the IC₅₀ values at 27.3, 32.7 and 26.6 μM, respectively.     

Five new triterpenoid saponins from the roots of Platycodon grandiflorum

Five new triterpenoid saponins, platycoside H [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside I [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside J [3-O-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside K [3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28-oic acid], and platycoside L [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28 oic acid], and three known triterpenoid saponins, platycoside F, platycoside B, and platycoside C, were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence.