New triterpene saponins from the root of Ilex pubescens

Two new triterpene glycosides named ilexpublesnin A (1) and ilexpublesnin B (2) were isolated from the root of Ilex pubescens. Their structures were determined as 3-O-(β-d-xylopyranosyl)-28-O-(β-d-glucopyranosyl)-3β, 19α-dihydroxyurs-23-oxo-12-en-28-oic acid (1) and 28-O-(β-d-xylopyranosyl-(2 → 1)-β-d-glucopyranosyl)-3β, 19α-dihydroxyurs-23-oxo-12-en-28-oic acid (2) on the basis of chemical and spectroscopic methods.     

New antioxidant and antiglycation active triterpenoid saponins from the root bark of Aralia taibaiensis

Four new oleanane type triterpenoid saponins (1-4) and a known saponin (5) were isolated from the root bark of Aralia taibaiensis Z.Z. Wang et H.C. Zheng. The structures of the four new compounds were elucidated as 3-O-{β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucurono-pyranosyl}-olean-11,13(18)-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (1), 3-O-{β-d-gluco-pyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucuronopyranosyl}-olean-11,13(18)-diene-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3-O-{β-d-glucopyranosyl-(1 → 2)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucuronopyranosyl}-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) and 3-O-{β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl}-oleanolic acid 28-O-β-d-glucopyranosyl ester (4), on the basis of extensive spectral analysis and chemical evidence. Compounds 1-5 exhibited moderate effects on antioxidant and antiglycation activities, which correlated with treatment of diabetes mellitus.     

Cytotoxic nor-dammarane triterpenoids from Dysoxylum hainanense

Four new nor-dammarane triterpenoids, 12β-O-acetyl-15α,28-dihydoxy-17β-methoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanran (1), 12β-O-acetyl-15α,17β,28-trihydoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanran (2), 12β-O-acetyl-15α,28-dihydoxy-3-oxo-17-en-20,21,22-23,24,25,26,27-octanordammanran (3), and 12β,15α,17β,28-tetrahydoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanran (4), were isolated from the 70% EtOH extract of Dysoxylum hainanense. The structures of the new compounds were elucidated by spectral methods. All the triterpenoids were in vitro evaluated for their cytotoxic activities against four tumor cell lines (A549, SK-OV-3, SKMEL-2 and HCT15).     

New triterpenoid saponins from Leontice smirnowii

Three new triterpene saponins, leonticins I (1), J (2) and L (3) were isolated from the tubers of Leontice smirnowii. On the basis of spectroscopic methods, including 2D NMR experiments (DEPT, gs-COSY, gs-HMQC, gs-HMBC and gs-HSQC-TOCSY), mass spectrometry (HR-ESI-MS) and chemical degradation, the structures of the new compounds were elucidated as 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-1 → 2)]-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (1), 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (2) and 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)]-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (3), respectively. The aglycone 3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid was observed for the first time in Leontice species.     

Cytotoxic taraxerane triterpenoids from Saussurea graminea

Four new taraxerane triterpenoids, 1β,3β-dihydroxy-11α,12α-oxidotaraxerane (1), 28-hydroxy-11α,12α-oxidotaraxerane-3-one (2), 3β-hydroxy-11α,12α-oxidotaraxerane-28-al (3), and 3-O-acetyl-11α,12α-oxidotaraxerane-28-al (4), together with three known compounds 3β-hydroxy-11α,12α-oxidotaraxerane (5), 3β,28-dihydroxy-11α,12α-oxidotaraxerane (6), and 11α,12α-oxidotaraxerane-3-one (7), were isolated from the 70% EtOH extract of Saussurea graminea. Their structures were elucidated on the basis of extensive 1D and 2D NMR (COSY, HMQC, HMBC and NOESY) analyses. The isolated compounds were evaluated in vitro for cytotoxic properties against eight tumor cell lines (A-549, BGC-823, HCT15, HeLa, HepG2, MCF-7, SGC-7901 and SK-MEL-2).     

Leiyemudanosides A–C,three new bidesmosidic triterpenoid saponins from the roots of Caulophyllum robustum

Three new oleanane bidesmosidic triterpenoid saponins, named leiyemudanosides A–C (1–3) were isolated from the roots of Caulophyllum robustum Maxim. Their structures were established by chemical and detailed spectroscopic analysis as 3-O-α-l-arabinopyranosyl-caulophyllogenin-28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1), 3-O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl-caulophyllogenin-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (2), and 3-O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl-echinocystic acid-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (3), respectively.     

A new triterpene glycoside from Centella erecta

A new (2α,3β)-23-sulphonyl-2,3-dihydroxyurs-12-en-28-oic acid O-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1) together with eighteen known compounds were isolated from Centella erecta (L.f.) Fern. Their structures were elucidated mainly by NMR and HRESIMS, as well as on comparison with the reported data.     

Three new triterpenoid saponins from root of Gardenia jasminoides Ellis

Three new compounds (Gardeniside A–C), 11α,12α-epoxy-3β-[(O-β-D-glucuronopyranoside-6′-O-methly ester)oxy]olean-28,13-olide (1), siaresinolic acid 3-O-β-D-glucuronopyranoside-6′-O-methly ester (2), and 3-O-β-D- glucuronopyranoside-6′-O-methly ester-siaresinolic acid-28-O-β-D- glucopyranoside (3), with seven known compounds oleanolic acid 3-O-β-D- glucuronopyranoside-6′-O-methly ester (4), oleanolic acid 3-O-β-D- glucuropyranoside (5), hederagenin 3-O-β-D- glucuronopyranoside-6′-O- methly ester (6), chikusetsusaponin IVa methyl ester (7), chikusetsusaponin (8), chikusetsusaponin IVa butyl ester (9), siaresinolic acid 28-o-β-d-glucopyranosyl ester (10) were isolated from the root of Gardenia jasminoides Ellis. Six compounds (1, 4–7, and 9) showed cytotoxic activities against HeLa, A549, MCF-7 and A354-S2 cell lines.     

A new triterpene saponin from Androsace integra

A new triterpene saponin, androsacin (1), along with two known compounds, ardisiacrispin A (2) and saxifragifolin A (3), were isolated from the whole plants of Androsace integra. The chemical structure of the new compound was elucidated as 3β-O-{β-D-glucopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-[O-β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranosyl}-16α-hydroxy-13β,28-epoxy-olean-30-al on the basis of spectral evidence. Ardisiacrispin A (2) was cytotoxic toward HepG2 cancer cell with the GI₅₀ value of 1.56 μM.     

Anti-inflammatory, antiviral and quantitative study of quercetin-3-O-β-D-glucuronide in Polygonum perfoliatum L

Quercetin-3-O-β-D-glucuronide, isolated from Polygonum perfoliatum L., was evaluated by antiviral efficacy against influenza A virus and anti-inflammatory activity in vivo in mouse, and it was used for quality evaluation of P. perfoliatum L.. In vivo study, oral administration of quercetin-3-O-β-D-glucuronide significantly suppressed ear edema induced by dimethyl benzene and peritoneal permeability induced by acetic acid in mice, and quercetin-3-O-β-D-glucuronide also showed to possess inhibitory activity against influenza A virus (FLUAV). In the present study, additionally, a rapid, simple and sensitive method for quantitative analysis of quercetin-3-O-β-D-glucuronide in P. perfoliatum L. was developed using high performance liquid chromatography (HPLC) coupled with photodiode array detection. The separation was carried out on a Lichrosher-C18 column (250 mm × 4.6 mm, 5 μm) together with a C18 guard column at isocratic elution systems of methanol (A) and 0.05% aqueous phosphoric acid (B) (43:57, v/v) with detection wavelength at 258 nm and column temperature at 30 °C. The method was validated for linearity, repeatability, limit of quantification (LOQ), precision and robustness. The contents of quercetin-3-O-β-D-glucuronide in 28 samples from different regions of China were between 0.06% and 2.09%. The developed analytical method was applied to investigate P. perfoliatum L. and for quality control of the herb.     

Anti-diabetic potential of ursolic acid stearoyl glucoside: a new triterpenic gycosidic ester from Lantana camara

A new stearoyl glucoside of ursolic acid, urs-12-en-3β-ol-28-oic acid 3β-d-glucopyranosyl-4′-octadecanoate and other compounds were isolated from the leaves of Lantana camara L. The structure of this new glycoside was elucidated and established by standard spectroscopic methods. In streptozotocin-induced diabetic rats it showed significant reduction in blood glucose level.     

Triterpenoids from Calophyllum inophyllum and their growth inhibitory effects on human leukemia HL-60 cells

A new friedelane-type triterpene (1), along with seven known triterpenoids, was isolated from the stems and leaves of Calophyllum inophyllum Linn. Their structures were established as 3β, 23-epoxy-friedelan-28-oic acid (1), friedelin (2), epifriedelanol (3), canophyllal (4), canophyllol (5), canophyllic acid (6), 3-oxo-friedelan-28-oic acid (7), and oleanolic acid (8) by spectroscopic methods (NMR, EI-MS). The growth inhibitory effects of these triterpenoids on human leukemia HL-60 cells were determined.     

Two new triterpenoids from the roots of Actinidia chinensis

Two new triterpenoids (1, 2), together with one flavonoid glycoside and thirteen known triterpenoids were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). The structures of the new constituents were elucidated as 12α-chloro-2α, 3β, 13β, 23-tetrahydroxyolean-28-oic acid-13-lactone (1), 2α, 3α, 19α, 23, 24-pentahydroxyurs-12-en-28-oic acid (2). Structure elucidation was accomplished by 1D, 2D NMR spectra (HMQC, HMBC, ¹H-¹H COSY, TOCSY, and NOESY) and mass spectrometry (ESIMS). Moreover, two known triterpenoids showed positive cytotoxic activity against LOVO and HepG2 cell lines.     

New anthraquinone glycosides from the roots of Morinda citrifolia

Six new anthraquinone glycosides: digiferruginol-1-methylether-11-O-β-gentiobioside (1); digiferruginol-11-O-β-primeveroside (2); damnacanthol-11-O-β-primeveroside (3); 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate (4); 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate (5); and 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone (6) were isolated from Morinda citrifolia (Rubiaceae) roots together with four known anthraquinone glycosides. The structures of the new compounds were established using spectral methods. For five of the new compounds, the sugar is attached via the hydroxymethyl group of the anthraquinone C-2 carbon. This type of bond is rarely found for anthraquinone glycosides isolated from natural sources.     

Sesquiterpenes inhibiting NO production from Celastrus orbiculatus

Two new (1 and 2) and one known (3) β-dihydroagarofuran sesquiterpenes were isolated from the fruits of Celastrus orbicultus Thunb. Their structures were elucidated as 1β,13-diacetoxy-8β,9β-dibenzoyloxy-β-dihydroagarofuran (1), 1β,13-diacetoxy-8α-hydroxy-9β-benzoyloxy-β-dihydroagarofuran (2), and 1β,6α,13-triacetoxy-9α-benzoyloxy-β-dihydroagarofuran (3), on the basis of spectroscopic data analyses. All the compounds exhibited inhibitory effects on LPS-induced nitric oxide production in murine microglial BV-2 cells.     

New flavonol glycosides from Aconitum burnatii Gáyer and Aconitum variegatum L.

Six flavonol glycosides, compounds 1-3 from A. burnatii Gáyer and 4-6 from A. variegatum L., were obtained from their methanol extracts of aerial parts. The identified structures were quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-p-coumaroyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (1), quercetin 3-O-β-d-glucopyranoside-7-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (2), quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-caffeoyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (3), kaempferol 3-O-β-d-galactopyranoside-7-O-α-l-arabinopyranoside (4), quercetin 3-O-β-d-glucopyranoside (5), and kaempferol 3-O-β-d-glucopyranoside (6). Compounds 1, 2 and 4 were isolated for the first time. The antioxidant potential of the methanol extracts and pure compounds was tested with different assays.     

A new steroidal saponin from the dried stems of Asparagus officinalis L

Yamogenin II (1), a new steroidal saponin with a unique aglycone moiety, and (25S)-spirostan-5-ene-3β-ol-3-O-α-l-rhamnopyranosyl-(1,2)-[α-l-rhamnopyranosyl-(1,4)]-β-d-glucopyranoside (2), were isolated from the dried stems of Asparagus officinalis L. The structure of 1 was assessed by spectroscopial analysis as (25S)-spirostan-5-ene-3β,21-diol-3-O-α-l-rhamnopyranosyl-(1,2)-[α-l-rhamnopyranosyl-(1,4)]-β-d-glucopyranoside.     

A new dihydrodibenzodioxinone from Hypericum x ‘Hidcote’

One new compound, 4-hydroxy-4a,7-dimethoxy-4,4a-dihydrodibenzo-p-dioxin-2(3H)-one (1), was isolated from the aerial parts of the hybrid Hypericum x ‘Hidcote’, together with 8 known compounds: caryophyllene-4,5-epoxide, quercetin, quercitrin, quercetin-3-O-β-D-galactopyranoside, epicatechin, betulinic acid methyl ester, β-sitosterol and β-sitosterol glucoside. The structure of the new compound, as well as its absolute configuration, was established by means of spectroscopic data analyses, including 2D NMR spectroscopy and X-ray structural analysis.     

Two new triterpene saponins from the aerial parts of Paraquilegia microphylla

Two new triterpene saponins, paraquinosides A (1) and B (2) were isolated from the aerial parts of Paraquilegia microphylla (Royle) Dromm. et Hutch, a Tibetan ethnic medicine distributed in the Qinghai–Tibet Plateau. On the basis of 1D and 2D NMR evidence, their structure was elucidated as 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl-15-dehydroxyl-16-O-methyl-24, 25-deoxy-26-hydroxylshengmanol-26-O-β-D-glucopyranoside (1) and 3-O-α-L-Rhamnopyranosyl (1→2)-[β-D-glucopyranosyl(1→3)]-β-D-glucopyranosyl-15-dehydroxyl-16-O-methyl-24, 25-deoxy-26-hydroxylshengmanol-26-O-β-D- glucopyranoside (2), respectively.     

New furostanol saponins from Smilax aspera L. and their in vitro cytotoxicity

The occurrence of the two new cis-fused A/B rings furostanol saponins (25S)-26-O-β-d-glucopyranosyl-5β-furostan-1β,3β,22α,26-tetraol-1-O-β-d-glucopyranoside and (25S)-26-O-β-d-glucopyranosyl-5β-furostan-1β,2β,3β,5β,22α,26-hexaol and the known compounds (25S)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranoside and (25S)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol-3-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranoside, trans-resveratrol, (+) catechin and (−) epicatechin in the rhizomes of Smilax aspera is reported. All saponins have been isolated as their 22-OMe derivatives, which were further subjected to extensive spectroscopic analysis. The isolated furostanol saponins were evaluated for cytotoxic activity against human normal amniotic and human lung carcinoma cell lines using neutral red and MTT assays. In vitro experiments showed significant cytotoxicity in a dose dependent manner with IC₅₀ values in the range of 32.98-94.53 µM.