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Antispasmodic saponins from bulbs of red onion, Allium cepa L. var. Tropea.

A phytochemical analysis of the polar extract from the red bulbs of Allium cepa L. var. Tropea, typical of Calabria, a southern region of Italy, was performed extensively for the first time, leading to the isolation of four new furostanol saponins, named tropeoside A1/A2 (1a/1b) and tropeoside B1/B2 (3a/3b), along with the respective 22-O-methyl derivatives (2a/2b and 4a/4b), almost certainly extraction artifacts. High concentrations of ascalonicoside A1/A2 (5a/5b) and ascalonicoside B (6), previously isolated from Allium ascalonicum Hort., were also found. This is the first report of furostanol saponins in this A. cepa variety. The chemical structures of the new compounds were established through a combination of extensive nuclear magnetic resonance, mass spectrometry and chemical analyses. High concentrations of quercetin, quercetin 4(I)-glucoside, taxifolin, taxifolin 7-glucoside, and phenylalanine were also isolated. The new saponins were found to possess antispasmodic activity in the guinea pig isolated ileum; such an effect might contribute to explaining the traditional use of onion in the treatment of disturbances of the gastrointestinal tract.

Magnetic Resonance Spectroscopy↗

Structure of steroidal saponins from underground parts of Allium nutans L.

Four steroidal glycosides including deltoside and nolinofuroside D and two novel saponins were isolated from underground parts of Allium nutans L. On the basis of the spectral (LSIMS and NMR) analysis, the structures of the new compounds were established as 25R Delta(5)-spirostan 3beta-ol-3-O-¿alpha-L-rhamnopyranosyl(1-->2)-[beta-D-glucopyranosyl(1 -->4)]-O-beta-D-galactopyranoside¿ and 25R Delta(5)-spirostan 1beta, 3beta-diol 1-O-beta-D-galactopyranoside. On the basis of the extraction efficiency, the concentration of saponins was established to be about 4% of dry matter, which makes this species a good source of steroidal saponins for commercial use.

Allium↗

Bioactive saponins from Swartzia schomburgkii from the suriname rainforest.

Bioassay-guided fractionation of the MeOH extract of Swartzia schomburgkii using the engineered yeast strains 1138, 1140, and 1353 as the bioassay tool resulted in the isolation of five active (2, 4-7) and three inactive (1, 3, 8) saponins. Saponins 4 and 6 are previously unreported. The structures of all of the saponins were established based on 1D and 2D NMR spectral analysis, on acid and alkaline hydrolysis followed by TLC and GC-MS, and by comparison with literature data for known compounds. Three of the isolated compounds (4-6) showed weak cytotoxicity against the M-109 cell line.

Antifungal Agents↗

New spirostanol steroids and steroidal saponins from roots and rhizomes of Dracaena angustifolia and their antiproliferative activity.

The MeOH extract of Nam ginseng (roots and rhizomes of Dracaena angustifolia) afforded nine new compounds, including three spirostanol sapogenins, named namogenins A-C (1-3), four spirostanol saponins, named namonins A-D (4-7), a furostanol saponin, named namonin E (8), and a pregnan glycoside, named namonin F (9), along with another eight known steroidal saponins (10-17). Their structures were determined on the basis of spectral analyses and chemical methods. All compounds were tested for their antiproliferative activity against murine colon 26-L5 carcinoma, human HT-1080 fibrosarcoma, and B-16 BL6 melanoma cells. Compounds 4, 5, and 10 showed potent antiproliferative activity against HT-1080 fibrosarcoma cells, having IC(50) values of 0.2, 0.3, and 0.6 microM, respectively, comparable to that of doxorubicin.

Animals↗

New bisdesmosidic triterpene saponins from the roots of Pulsatilla chinensis.

Further phytochemical analysis aimed at the triterpene saponin constituents of the roots of Pulsatilla chinensis has resulted in the isolation of four new bisdesmosidic triterpene saponins whose aglycons are based on the lupane skeleton (1-4), together with three known saponins (5-7). The structures of the new compounds were determined by spectroscopic analysis and acid-catalyzed hydrolysis.

Antineoplastic Agents, Phytogenic↗

Bioactive saponins from Acacia tenuifolia from the suriname rainforest.

Bioassay-guided fractionation of the MeOH extract of Acacia tenuifolia using the engineered yeast strains 1138, 1140, 1353, and Sc7 as the bioassay tool resulted in the isolation of the three new saponins 3, 5, and 6 and the three known saponins 1, 2, and 4. The structures of the new compounds were established on the basis of HRMS, 1D and 2D NMR spectral data on the intact saponins, and GC-MS analyses of the sugars. Compounds 1,2 and 5,6 showed cytotoxicity against mammalian cell lines.

Acacia↗

Characterization of new sweet triterpene saponins from Albizia myriophylla.

Five new oleanane-type triterpene saponins, albiziasaponins A-E (1-5), were isolated from the stems of Albizia myriophylla collected in Thailand, together with two known triterpene saponins, licorice-saponin F3 and yunganoside B(1). The structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. In addition, when sensory tests were performed on sweetness, albiziasaponin B (2), with a carbonyl group at the C-30 position, was found to show a potent sweetness intensity relative to sucrose (600 times).

Adult↗

Eranthisaponins A and B, two new bisdesmosidic triterpene saponins from the tubers of Eranthis cilicica.

The present investigation aimed at the glycoside constituents of the tubers of Eranthis cilicica has resulted in the isolation of two new bisdesmosidic triterpene saponins based upon hederagenin, named eranthisaponins A (1) and B (2), along with four known triterpene saponins. The structures of the new saponins 1 and 2 were determined on the basis of spectroscopic analysis, including extensive 1D and 2D NMR data, and acid hydrolysis followed by chromatographic analysis. This is the first report concerning the secondary metabolites of E. cilicica.

Chromatography, High Pressure Liquid↗

Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships.

A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol (1) on the basis of spectroscopic analysis (1H NMR, 13C NMR, 1H-1H COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 microg/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.

Antifungal Agents↗

Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda.

Three new oleanane-type triterpene saponins (1-3), named grandibracteosides A-C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance.

Albizzia↗

Saponins of Allium elburzense.

A phytochemical investigation of the bulbs of Allium elburzense has been undertaken, leading to the isolation of 13 furostanol and spirostanol saponins, eight of which are new, namely, elburzensosides A1/A2 (1a/1b), B1/B2 (2a/2b), C1/C2 (3a/3b), and D1/D2 (4a/4b). On the basis of spectroscopic analysis, mainly 2D NMR and mass spectrometry, and chemical methods, the structures of the new compounds were determined as furost-2alpha,3beta,5alpha,6beta,22alpha-pentol 3-O-beta-D-glucopyranosyl 26-O-beta-D-glucopyranoside (1a), furost-2alpha,3beta,5alpha,6beta,22alpha-pentol 3-O-[beta-D-glucopyranosyl-(1-->4)-O-beta-D-glucopyranosyl] 26-O-beta-D-glucopyranoside (2a), furost-2alpha,3beta,5alpha,22alpha-tetrol 3-O-beta-D-glucopyranosyl 26-O-beta-D-glucopyranoside (3a), and furost-2alpha,3beta,5alpha,22alpha-tetrol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (4a), and the corresponding epimers at position 22 (1b-4b). Along with these compounds we have isolated the corresponding 22-O-methyl derivatives that we consider extraction artifacts. All the new elburzensosides A1/A2-D1/D2 possess as a common structural feature an OH-5alphathat is rare among furostanol saponins. The reported compounds have been isolated in large amounts, and this makes A. elburzense a prolific producer of saponins of the furostanol and spirostanol types.

Allium↗

Triterpenoid saponins from the roots of Pulsatilla koreana.

Six new saponins, five lupanes (1-5) and one oleanane (6), along with 11 known saponins, were isolated from the roots of Pulsatilla koreana. The structures of the new saponins were found to be 23-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (1), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (2), 3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (4), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (5), and hederagenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (6). Their structures were determined on the basis of 1D and 2D NMR ((13)C NMR, (1)H NMR, (1)H-(1)H COSY, HMQC, and HMBC) methods, FABMS, and hydrolysis. All isolated compounds were evaluated for their cytotoxic activity against A-549 human lung carcinoma cells.

Antineoplastic Agents, Phytogenic↗

Triterpene saponins from the leaves of Ilex kudingcha.

Nine new triterpene saponins, ilekudinosides K-S (1-9), and eight known triterpene saponins were isolated from the 70% ethanol extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (1), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-beta-kudinlactone (2), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-gamma-kudinlactone (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (4), 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl-alpha-kudinlactone (5), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-alpha-kudinlactone (6), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-beta-kudinlactone (7), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-beta-kudinlactone (8), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-gamma-kudinlactone (9), respectively. The structures and stereochemistry of compounds 1-9 were elucidated by spectroscopic data interpretation and chemical degradation.

Drugs, Chinese Herbal↗

Biologically active triterpenoid saponins from Acanthopanax senticosus.

Three new triterpenoid saponins, acanthopanaxosides A (1), B (7), and C (13), were isolated from the leaves of Acanthopanax senticosus, together with 12 known saponins. The structures of these new saponins were established as 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-30-nor-olean-12,20(29)-dien-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (7), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-3beta-hydroxyolean-12-ene-28,29-dioic acid (13), on the basis of spectroscopic analysis and chemical degradation. Among the known compounds, sessiloside and tauroside H1 are reported for the first time from A. senticosus. The biological activity of compounds 1-15 was examined against pancreatic lipase. Ciwujianoside C1 (6), tauroside H1 (11), 3-O-alpha-rhamnopyranosyl-(1-->2)-alpha-arabinopyranosyl mesembryanthemoidigenic acid (12), acanthopanaxoside C (13), sessiloside (14), and chiisanoside (15) inhibited pancreatic lipase activity in vitro. In turn, ciwujianosides C2 (3), D2 (5), C4 (8), and C3 (10) and hederasaponin B (9) enhanced this enzyme.

Drugs, Chinese Herbal↗

Constituents of leguminous plants, XIII. New triterpenoid saponins from Wistaria brachybotrys.

Two new triterpenoid saponins, wistariasaponins D [1] amd G [2], and the known saponin dehydrosoyasaponin I [3] were isolated from the knots of Wistaria brachybotrys. The Structures of 1 and 2 were determined from their chemical and physicochemical evidence. The inhibitory effects of these saponins on the activation of Epstein-Barr virus early antigen that was induced by a tumor promoter were also tested for the primary screening of antitumor-promoting activities.

Antigens, Viral↗

In vivo and in vitro biosynthesis of saponins in sea cucumbers.

The triterpene precursor of saponins in sea cucumbers has been identified as parkeol [lanost-9(11)-en-3 beta-ol] [1]. Dissection of the sea cucumbers Holothuria floridea and Actinopyga agassize after incubations with radiolabeled parkeol demonstrated that saponin biosynthesis occurs exclusively in the Cuvier gland. This result was corroborated by incubating a cell-free extract of the Cuvier gland with labeled parkeol and observing transformation of the precursor to saponins.

Animals↗

Triterpenoid saponins from Bellis bernardii.

Nine saponins were isolated from the deacylated saponin mixture obtained from the whole plants of Bellis bernardii. Their structures have been elucidated from NMR and MS data and by chemical derivatization. Three were glycosides of the recently reported bellisonic acid (2 beta, 3 beta,-23-trihydroxy-16-oxoolean-12-en-28-oic acid), with the major compounds being related glycosides of polygalacic acid (2 beta, 3 beta, 16 alpha, 23-tetrahydroxyolean-12-en-28-oic acid). In addition, a saponin of bayogenin (2 beta, 3 beta, 23-trihydroxyolean-12-en-28-oic acid) was obtained and is the first acyl glycoside of this aglycon with a free hydroxyl group at C-3.

Carbohydrate Sequence↗

Lathyrus saponin, a new trisaccharide glycoside from Lathyrus japonicus.

A new triterpenoid saponin, named Lathyrus saponin (3), was isolated from the whole plant of Lathyrus japonicus Willd. together with two known saponins, azukisaponins II (1) and V (2). as their methyl esters. The structure of 3 was determined to be soyasapogenol B 3-0-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glu curonopyranoside on the basis of physicochemical and spectroscopic methods.

Carbohydrate Sequence↗