Triterpene saponins from the roots of Dipsacus asper and their protective effects against the Aβ(25-35) induced cytotoxicity in PC12 cells

Three new triterpene saponins, named asperosaponin A-C (1-3), together with seven known triterpene saponins (4-10) were isolated from the roots of Dipsacus asper. The structures of compounds 1-3 were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1-3, 6-10 had significantly protective effects in PC12 cells against the Aβ(25-35) induced cytotoxicity. All the compounds isolated showed no cytotoxic activity against three human cancer cell lines, A-549, Bel-7402 and BGC-823.     

Steroidal saponins from Fritillaria pallidiflora Schrenk

Five new steroidal saponins, Pallidifloside D (1), Pallidifloside E (2), Pallidifloside G (5), Pallidifloside H (6) and Pallidifloside I (7), together with seven other steroidal saponins (3, 4, 8-12) were isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were established by spectroscopic techniques (IR, MS, 1D and 2D NMR) and chemical means. The isolated steroidal saponins were evaluated for cyotoxic activity against human C6 brain gliomas and Hela cervix cancer cell lines using MTT assays. Compounds 1, 10, 11, 12 showed cytotoxicity against C6 and Hela cell lines with IC(50) values in the range of 5.1-75.8μM.     

Five new furostanol saponins from the rhizomes of Tupistra chinensis

Five new furostanol saponins (1-5), together with three known compounds (6-8) were obtained from the n-butanol soluble fraction of ethanol extract from Tupistra chinensis. Their structures were determined on the basis of chemical methods and spectral data. The isolated compounds were tested in vitro for their cytotoxic activities against the A549, HepG 2 and Caski cancer cell lines. Among them, compounds 6, 7, and 8 showed cytotoxicity against A549 cancer cell lines with IC(50) values of 6.6, 6.7 and 29.1 μM, respectively.     

Two new cytotoxic triterpenoid saponins from the roots of Clematis argentilucida

Bioassay-guided fractionation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of two new triterpenoid saponins along with a known one, cussonside B (3). By extensive spectral analysis and chemical evidences, the structures of the two new saponins were determined to be 3β-O-[β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] hederagenin-11,13-dien-28-oic acid (1) and 3β-O-{β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl} oleanolic acid (2), respectively. Saponin 1 is the first example of triterpenoid saponins with two double bonds located at C-11 and C-13 in the aglycone from the genus Clematis. The two new saponins exhibited significant cytotoxicity against human leukemia HL-60 cell lines, human hepatocellular carcinoma Hep-G2 cell lines and human glioblastoma U251MG cell lines with a range of IC(50) values from 2.74 to 25.40μM, while 3 showed inactivity against all of the three cancer cell lines.     

Chemical characteristics of saponins from Paris fargesii var. brevipetala and cytotoxic activity of its main ingredient, paris saponin H

More attention was paid to the anti-tumor activity of Rhizoma Paridis (RP) recently, of which the wild resource was decreased significantly. This study was aimed to elucidate the chemical characteristics of Paris fargesii var. brevipetala (PFB) that may be administrated as alternate resource of legal RP. A HPLC-ELSD method was established to characterize the steroid saponins in rhizomes of PFB and two legal Paris species [Paris polyphylla var. chinensis (PPC) and P. polyphylla var. yunnanensis (PPY)] in Chinese Pharmacopoeia (CP). Ten saponins (paris saponins I, II, V, VI, VII, H, gracillin and other three paris saponins) were involved as standards. The results indicated that PFB contained pennogenyl saponins as the main components with small amounts of diosgenin saponins. The total contents of the detected saponins in PFB ranged from 9.12mg/g to 85.33mg/g. Nine of the twelve PFB samples own a total content of paris saponins I, II, VI, and VII more than 6.0mg/g (meeting the standard of CP 2010 edition). Principal Component Analysis (PCA) and Partial Least Squares-Discriminate Analysis (PLS-DA) both confirmed the fact that saponin profiles of PFB, PPC and PPY were different from each other. In addition, paris saponin H (Ps H), the predominant saponin of PFB (>50%), was tested in vitro to evaluate its cytotoxic activities on HepG2, A549, RPE and L929 cells with a positive control of Cisplatin. Ps H showed a remarkable cytotoxic activity on A549 cells with an IC(50) value of 1.53±0.08μg/mL.     

Four new sesquiterpenes from Commiphora myrrha and their neuroprotective effects

Four new sesquiterpenes, myrrhterpenoids K-N (1-4) have been isolated from the resin of Commiphora myrrha. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESIMS, HR-ESIMS, 1D and 2D NMR). Compounds 1 and 4 showed neuroprotective effects against MPP(+)-induced neuronal cell death in SH-SY5Y cells.     

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: confirmation of their synonymy

A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3β,23-diol 3-O-{β-D-xylopyranosyl-(1→2)-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five cancer cell lines and for antioxidant and cytoprotective activity.     

New triterpenoids from the stems and leaves of Panax ginseng

Three new dammarane-type triterpene saponins ginsenosides Rh(18) (1), Rh(19) (3) and Rh(20) (4), along with two new triterpene sapogenins 12β,23(R)-epoxydammara-24-ene-3β,6α,20(S)-triol (2) and dammara-(20E)22,25-diene-3β,6α,12β,24S-tetrol (5) were isolated from the stems and leaves of Panax ginseng C. A. Mey. Their structures were elucidated on the basis of spectral evidence and comparisons with literature data.     

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.     

Selective modulation of P-glycoprotein activity by steroidal saponines from Paris polyphylla

Bio-guided fractionation of the roots of Paris polyphylla (Trilliaceae), based on inhibition of P-glycoprotein-mediated daunorubicin efflux in K562/R7 cell line, led to isolation and identification of the three saponins 3-O-Rha(1-->2)[Ara(1-->4)]Glc-pennogenine, gracillin and polyphyllin D, and the two ecdysteroids 20-hydroxyecdysone and pinnatasterone. These compounds were tested for multidrug reversion on P-glycoprotein (ABCB1) with both drug-selected and transfected cell lines, and also on Breast Cancer Resistance Protein (BCRP/ABCG2). By contrast to a weak efficiency on BCRP, the three saponins displayed significant effects as inhibitors of P-glycoprotein-mediated drug efflux.     

Asterosaponins from the starfish Culcita novaeguineae and their bioactivities

Bioassay-guided fractionation of the n-BuOH extract of the starfish Culcita novaeguineae resulted in the isolation of one new sulfated steroidal glycoside (asterosaponin) (1), along with three known asterosaponins, thornasteroside A (2), marthasteroside A(1) (3) and regularoside A (4), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Their structures were elucidated by extensive spectral studies and chemical evidences. All the saponins showed moderate cytotoxicity against cancer cell lines K-562 and BEL-7402.     

Isorhynchophylline: A plant alkaloid with therapeutic potential for cardiovascular and central nervous system diseases

Uncaria species (Gouteng in Chinese) have been used as a plant medicine to treat ailments of cardiovascular and central nervous systems. As the main alkaloid constituent of Uncaria species, isorhynchophylline has drawn extensive attention toward antihypertensive and neuroprotective activities in recent years. Isorhynchophylline mainly acts on cardiovascular and central nervous systems diseases including hypertension, brachycardia, arrhythmia, and sedation, vascular dementia, and amnesia. Isorhynchophylline also has effects on anticoagulation, inhibition vascular smooth muscle cell apoptosis and proliferation, anti-multidrug resistant of lung cells, anti-endotoxemic, and antispasmodic. The active mechanisms are related to modulation on calcium ion channel, protection neural and neuroglial cells against β-amyloid(25-35)-induced neurotoxicity and via inducing autophagy. As a candidate drug of several cardiovascular and central nervous systems diseases, isorhynchophylline will attract scientists to pursue the potential related pharmacological effects and its mechanism with new technologies. But relatively few clinical application of isorhynchophylline has been conducted on its pharmacological activities. It requires more in vivo validations and further investigations of antihypertensive and neuroprotective mechanisms of isorhynchophylline.     

Analgesic and antipyretic effects of Capparis zeylanica leaves

The ethanol and water extracts of Capparis zeylanica leaves showed dose-dependent and significant (P<0.05) increases in pain threshold in tail-immersion test. Moreover, both the extracts (100-200 mg/kg) exhibited a dose-dependent inhibition of writhing and also showed a significant (P<0.001) inhibition of both phases of the formalin pain test. The water extract (200 mg/kg) significantly (P<0.01) reversed yeast-induced fever. Preliminary phytochemical screening of the extracts showed the presence of alkaloids, flavonoids, saponins glycosides, terpenoids, tannins, proteins and carbohydrates.     

Effect of organogenesis on steroidal saponin biosynthesis in calli cultures of Ruscus aculeatus

Calli cultures derived from Ruscus aculeatus rhizomes were investigated for their potential to biosynthesize saponins. The capacity of undifferentiated tissues to form steroidal saponins is very limited, but when the calli developed organogenesis, mainly aerial shoots and roots, the saponin production increased significantly. Plantlets regenerated from aerial shoots of Ruscus calli showed a saponin pattern similar to that of the callus cultures but the levels of saponins found in the aerial part and roots were significantly greater.     

Neuroprotective labdane diterpenes from Fritillaria ebeiensis

By bioactivity-guided isolation, two labdane diterpenes (1 and 2) have been isolated from the bulbs of Fritillaria ebeiensis. Their structures were elucidated as 6α,7β-dihydroxy-labda-8(17),12(E),14-triene (1) and 6-oxo-2α-hydroxy-labda-7,12(E), 14-triene (2), on the basis of spectroscopic data analysis (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR). Both of the isolates showed neuroprotective effects against MPP⁺-induced neuronal cell death in human dopaminergic neuroblastoma SH-SY5Y cells.     

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.     

Steroidal saponins from Smilacina japonica

Three new steroidal saponins, japonicoside A (1), japonicoside B (2) and japonicoside C (3) were isolated from the dried rhizomes and roots of Smilacina japonica A. Gray. Their structures were elucidated as (25S)-5α-spirostan-9(11)-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1), (25S)-5α-spirostan-9(11)-en-3β,17α-diol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2) and (25S)-5α-spirostan-9(11)-en-3β,17α,24α-triol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (3) on the basis of chemical methods and detailed spectroscopic analysis, including 1D, 2D NMR and HR-ESI-MS. The cytotoxicity of isolated compounds was evaluated in vitro for cytotoxic properties against human hepatocellular carcinoma cells (SMMC-7221) and human colorectal adenocarcinoma cells (DLD-1), respectively.     

Iridoids from the roots of Valeriana jatamansi and their neuroprotective effects

Three new iridoids, valeriandoids A–C (1–3), together with three known analogues (4–6), were isolated from the roots of Valeriana jatamansi. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESIMS, HRESIMS, 1D and 2D NMR) and by comparison of their NMR data with those of related compounds. All the isolated compounds were evaluated for their neuroprotective effects and compounds 1, 3, 4 and 6 showed moderate neuroprotective effects.     

Identification of Ruscus steroidal saponins by HPLC-MS analysis

A novel HPLC-UV method has been developed for the fingerprint analysis of the steroidal saponins in the rhizomes of three Ruscus species (Ruscus aculeatus, Ruscus hypoglossum and Ruscus colchicus). Saponins were identified by HPLC-ESI-MS. During the study a new major saponin was detected in the rhizomes of R. hypoglossum and R. colchicus. The structure of the new compound was defined as 1-O-[alpha-L-rhamnopyranosyl-(1-->2)-6-O-acetyl-beta-D-galactopyranosyl]-1beta,3beta,22xi,26-tetrahydroxy-furost-5(6)-en-26-O-beta-D-glucopyranoside (8) by spectral analysis.     

Antiproliferative activity of Saponaria vaccaria constituents and related compounds

Total methanolic extracts of Saponaria vaccaria seed derived from several varieties, as well as various purified components obtained through successive chromatographic separations of total extracts were evaluated for their growth inhibitory activity in WiDr (colon), MDA-MB-231 (breast), NCI-417 (lung) and PC-3 (prostate) human cancer cells as well as the non-tumorigenic fibroblast BJ (CRL-2522) cell line using MTT colorimetric assay. Purified bisdesmosidic saponins segetoside H and I were further examined using microscopy and apoptosis assays. Bisdesmosidic saponins exhibited dose-dependent growth inhibitory and selective apoptosis-inducing activity. Growth inhibitory effects were particularly strong in a breast (MDA-MB-231) and a prostate (PC-3) cancer cell line. Total extracts exhibited a different preference being most active against a colon cancer cell line (WiDr). In a comparison of varieties, all of the total seed extracts exhibited similar dose-dependent activities, but with some variation in potency. Monodesmosidic saponins vaccarosides A and B, phenolic vaccarin, and cyclopeptide segetalin A, co-occurring seed substituents, did not exhibit activity. The non-tumorigenic fibroblast cell line BJ (CRL 2522) was growth inhibited but did not undergo apoptosis when treated with bisdesmosidic saponins at low micromolar concentrations. Saponin-rich extracts from Kochia scoparia seed and Chenopodium quinoa were also evaluated alongside Saponaria saponins but did not exhibit activity. Closely related Quillaja saponins exhibited activity but were less potent.