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Triterpenoid saponins from the roots of tea plant (Camellia sinensis var. assamica).

Three olean-12-ene type triterpenoid saponins, named TR-saponins A, B and C, were isolated as methyl esters from tea roots (Camellia sinesis var. assamica) after treatment with diazomethane. Their structures were established as the methyl esters of 3-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-glucuronopyranosyl-21, 22-di-O-angeloyl-R1-barrigenol-23-oic acid, 3-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-glucuronopyranosyl-21-O-angeloyl-22-O-2-me thylbutanoyl-R1- barrigenol-23-oic acid and 3-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-glucuronopyranosyl-16 alpha-O-acetyl-21-O-angeloyl-22-O-2-methylbutanoyl-R1-bar rigenol-23-oic acid, by extensive 1D and 2D-NMR as well as FABMS and HR-MS analyses.

Magnetic Resonance Spectroscopy↗

Nootropic and anxiolytic activity of saponins of Albizzia lebbeck leaves.

The effect of saponin containing, n-butanolic fraction (BF), extracted from dried leaves of Albizzia lebbeck, was studied on cognitive behavior and anxiety in albino mice. The elevated plus maze was used for assessment of both nootropic and anxiolytic activity. The nootropic activity was evaluated by recording the effect of BF (0, 10, 25, and 50 mg/kg) on the transfer latency, whereas anxiolytic activity was assessed by studying its effect on the duration of occupancy in the closed arm. Results showed significant improvement in the retention ability of the normal and amnesic mice as compared to their respective controls. Animals treated with BF (25 mg/kg) spent more time in the open arm in a dose-dependent manner. The BF was without any significant effect on motor coordination. However, it significantly inhibited passivity and hypothermia induced by baclofen (10 mg/kg), a GABA(B) agonist. The data emanated in the present study suggests involvement of gamma-aminobutyric acid (GABA) in the nootropic and anxiolytic activity of saponins obtained from A. lebbeck.

1-Butanol↗

Study of the adjuvant activity of new MDP derivatives and purified saponins and their influence on HIV-1 replication in vitro.

Muramyl dipeptide (MDP), eight new lipophilic MDP derivatives (MDPs) and three purified saponins were evaluated for their ability to induce immune responses in mice immunized with HIV-1 envelope protein rgp160 and for their ability to influence the HIV-1 replication in vitro. Three of nine new synthetic MDP derivatives (beta-butyl-MDP, MTPO-26 and beta-cholesteryl-MDP) and one saponin (Taurosid I) have been shown to induce strong humoral immune responses to HIV-1 envelope glycoproteins rgp160 and rgp120. Three substances (beta-butyl-MDP, MDP-cholyl and beta-G27-MDP) induced high levels of T-cell stimulation to HIV-1 rgp160. beta-butyl-MDP induced the strongest B- and T-cell responses to HIV-1 glycoproteins. Two substances (beta-butyl-MDP and Taurosid I) did not induce an enhancement of HIV-1 replication in vitro and can be considered as promising adjuvants.

Acetylmuramyl-Alanyl-Isoglutamine↗

Ultrasound-induced physiological effects and secondary metabolite (saponin) production in Panax ginseng cell cultures.

This work was aimed at the effects of ultrasound (US) on the growth and secondary metabolite biosynthesis of cultured plant cells. Suspension cultures of Panax ginseng cells were exposed to US at power density below 82 mW/cm3 for short periods of time (1-4 min) in a US bath (38.5-kHz fixed frequency and 810 W maximum peak power). Under most exposure conditions, US stimulated the biosynthesis of secondary metabolites, the ginsenoside saponins of ginseng cells, increasing the total saponin content of the cell by up to 75%. The growth and viability of ginseng cells were usually depressed immediately after the exposure to US, but recovered gradually to levels similar to those of a normal culture in a few days, with virtually no net loss of biomass yield at the end of the culture period. At some lower US doses, sonicated cultures could even reach slightly higher biomass yields than that of normal cultures. The effects of US on cell growth and secondary metabolite yield showed a significant correlation with the total US energy emitted (i.e., the product of US power and exposure time). Mechanical stress and microstreaming induced by acoustic cavitation were considered as the most possible causes of the various physiological effects of US on ginseng cells. In particular, the stimulation of secondary metabolite production by US may be a result of US-induced plant cell defense response.

Cells, Cultured↗

Saponins from Styrax officinalis.

Three triterpene saponins named Styrax-saponin A-C (1-3) were found in pericarps of Styrax officinalis together with the deacylsaponin (4). Structural determinations were achieved using 1D-, 2D-NMR and mass spectrometry.

Humans↗

Triterpenoid saponins from the roots of Silene cucubalus.

A new triterpenoid saponin was isolated from the roots of Silene cucubalus and its structure was determined on the basis of one- and two-dimensional NMR spectroscopy as gypsogenin 3-O-beta-xylopyranosyl-(1-->3)-[beta-galactopyranosyl-(1-->2)]-beta-glucuronopyranoside. A known saponin, quillaic acid 3-O-beta-xylopyranosyl-(1-->3)-[beta-galactopyranosyl-(1-->2)]-beta-glucuronopyranoside, was also isolated.

Humans↗

Furostanol saponins from Tribulus terrestris.

An HPLC-ELSD-ESI-MS method has been developed for the analysis of the steroidal saponins in the aerial parts of Tribulus terrestris. Protodioscin, a new saponin (5,6-dihydroprotodioscin, neoprotodioscin) and their respective sulfates were detected. The structure of the new compound was elucidated on the basis of NMR and ESI-MS spectral analysis.

Chromatography, High Pressure Liquid↗

Saponins and phenolic content in plant dietary additives of a traditional subsistence community, the Batemi of Ngorongoro District, Tanzania.

Reports of plants added to milk and meat-based soups by the Maasai and Batemi in East Africa support a role for phenolic antioxidants and hypocholesterolemic agents in the diet, and provide explanation of the low incidence of cardiovascular disease of populations that traditionally consume high levels of dietary fat and cholesterol. Plant food additives used by the Batemi of Ngorongoro District, Tanzania, were tabulated, based on interviews with 22 informants, while 17 specimens were collected in the field and analyzed for saponin and phenolic content. A total of 81% of the Batemi additives and 82% of those known to be used by the Maasai contain potentially hypocholesterolemic saponins and/or phenolics.

Anticholesteremic Agents↗

Acyl-CoA: cholesterol acyltransferase inhibitory activity of ginseng sapogenins, produced from the ginseng saponins.

Ginseng sapogenins were produced from ginseng saponins, isolated from Korean ginseng roots. Ginseng saponins very mildly inhibited acyl-CoA:cholesterol acyltransferase (ACAT) in vitro, however, the sapogenins showed strong inhibitory activity on microsomal ACAT. Therefore, the sapogenins will be one of key ingredients of ginseng affected a lowering of the serum total cholesterol level.

Animals↗

Isolation and characterization of novel cytotoxic saponins from Archidendron ellipticum.

A series of new ester saponins, elliptosides A-J, has been isolated from the tropical plant Archidendron ellipticum (Leguminosae). These saponins were particularly cytotoxic to certain renal and melanoma cancer cell lines in the NCI's 60-cell line human tumor screen. The structures of elliptosides A, E, and F were elucidated by spectroscopic and chemical means. Elliptoside A showed in vivo antitumor activity against the LOX melanoma cell line.

Antineoplastic Agents, Phytogenic↗

Macrophage-oriented cytotoxic activity of novel triterpene saponins extracted from roots of Securidaca inappendiculata.

It is recognized that macrophages in peripheral tissues often proliferate under pathological conditions such as tumors, inflammation and atherosclerosis. Because the growth state of macrophages is believed to be a factor regulating the pathological process of the diseases, substances that regulate macrophage growth or survival may be useful for disease control. In this paper, we identified the activity inhibiting macrophage growth in a hot water extract of roots of Securidaca inappendiculata. The extract markedly inhibited macrophage colony-stimulating factor (M-CSF/CSF-1)-induced growth of macrophages, whereas it exerted a less potent effect on growth of Concanavalin A (Con A)-stimulated thymocytes or M-CSF-stimulated bone marrow cells. The inhibition of macrophage growth was caused by a cytotoxic effect rather than a cytostatic effect. Cell death was due to the induction of apoptosis, as judged by staining with terminal deoxynucleotidyl transferase-mediated d-UTP nick end labelling (TUNEL). The cytotoxic activity seemed to be specific to peripheral macrophages; it showed a weak effect on the growth and survival of tumor cell lines including a macrophage-like cell line, J-774.1. Moreover, the saponin fraction induced apoptotic cell death of macrophages only when they were stimulated by M-CSF; it did not affect the viability of macrophages cultured without M-CSF or with granulocyte/macrophage-CSF. We determined the structures of the two active triterpene saponin compounds in the fraction, named securioside A and securioside B having a 3,4-dimethoxycinnamic group which is essential for the cell death-inducing activity. They are believed to be the primary compounds of new drugs for the treatment of pathological states in which macrophage proliferation occurs.

Animals↗

Corynebacterium parvum as an adjuvant for Trypanosoma cruzi epimastigote vaccines: a comparison with saponin and Bordetella pertussis.

The effect was compared in CBA mice of adding Corynebacterium parvum, saponin, and Bordetella pertussis to living or killed Trypanosoma cruzi (Y strain) epimastigote vaccines on the induction of protective immunity against subcutaneous (s.c.) challenge with blood trypomastigotes. The addition of C. parvum to a low dose of T. cruzi vaccine, which alone was non-protective, generated a greater degree of protection than did saponin or B. pertussis. C. parvum alone increased resistance to infection to a variable and usually weak extent. The addition of C. parvum to larger doses of T. cruzi vaccine, which were themselves sufficient to elicit some degree of protection, improved resistance when the challenge was given 1 or 12 weeks after immunization, but lowered it at 3 weeks. It is concluded that the comparative efficacy of adjuvants for T. cruzi vaccines needs to be assessed on 3 parameters: (1) the dose of antigen, (2) the dose of adjuvant and (3) the time interval between immunization and challenge.

Adjuvants, Immunologic↗

Studies on the constituents of Chenopodium quinoa seeds: isolation and characterization of new triterpene saponins.

Six triterpenoid saponins were isolated from the edible grain quinoa, which is seeds of Chenopodium quinoa (Chenopodiaceae). Following are their structures: phytolaccagenic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside (1); phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1' '-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (2); phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1' "-->3' ')-beta-D-xylopyranosyl-(1' '-->2')-beta-D-glucopyranosyl]-28-O-beta-D-glucopyranoside (3); phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1' "-->2' ')-beta-D-glucopyranosyl-(1' '-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (4); oleanolic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside (5); and oleanolic acid 3-O-[beta-D-glucopyranosyl-(1' '-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (6). The oleanane-type saponins (5, 6) were isolated for the first time in this plant, two of the phytolaccagenane (1, 3) were new compounds and two (2, 4) were previously found in quinoa. The structures were characterized on the basis of hydrolysis and spectral evidence, including 1D- and 2-D NMR (HMQC and HMBC) and ESI-MS analyses.

Carbohydrate Sequence↗

New oleanane saponins in Chenopodium quinoa.

Six triterpenoid saponins were isolated from the seeds of Chenopodium quinoa (Chenopodiaceae). Their structures were as follows: phytolaccagenic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside (1); spergulagenic acid 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl-28-O-beta-D-glucopyranoside (2); hederagenin 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (3); phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-28-O-beta-D-glucopyranoside (4); hederagenin 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-28-O-beta-D-glucopyranoside (5); and spergulagenic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside (6). Saponins 5 and 6 are new. The structures were characterized on the basis of hydrolysis and spectral evidence, including IR, UV, optical rotations, 1D- and 2D-NMR (HMQC and HMBC), ESIMS, and FABMS analyses.

Chenopodiaceae↗

Steroidal saponins of Yucca schidigera Roezl.

Eight steroidal saponins have been isolated from Yucca schidigera Roezl. trunk, and their structures were established by spectral (MS and NMR) techniques. These included three novel furostanol glycosides including 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-5 beta(25R)-furostan-3 beta,22 alpha,26-triol 26-O-beta-D-glucopyranoside, 3-O-beta-D-glcopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-5 beta(25R)-furost-20(22)-en-3 beta,26-diol-12-one 26-O-beta-D-glucopyranoside, 3-O-beta-D-glcopyranosyl-(1-->2)-beta-D-glucopyranosyl-5 beta(25R)-furostan-3 beta,22 alpha,26-triol 26-O-beta-D-glucopyranoside, and five known spirostanol glycosides. On the basis of the extraction efficiency, furostanol glycosides made up only 6.8% of total saponins isolated.

Liliaceae↗

Studies on the constituents of a Brazilian folk infusion. Isolation and structure elucidation of new triterpene saponins from Ilex amara leaves.

The isolation of three new triterpene saponins 3beta-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-2-O-acetylarabinopyranosylolean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl ester (2), 3beta-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-O-arabinopyranosylurs-12-en-28-oic acid (3), and 3beta-O-beta-D-glucopyranosyl-(1-->2)-beta-D-O-galactopyranosylurs-12-en-28-oic acid (4) together with five known saponins and one flavonoid glycoside from the aqueous infusion of Ilex amara (Vellozo) Loes. leaves is reported. All structures were elucidated by spectroscopic methods, including the concerted application of one-dimensional (1H, TOCSY, 13C, and 13C DEPT NMR) and two-dimensional NMR techniques (DQF-COSY, HSQC, and HMBC).

Brazil↗

Triterpene saponins from debittered quinoa (Chenopodium quinoa) seeds.

Twelve triterpene saponins have been isolated from the debittered seeds of quinoa (Chenopodium quinoa), and their structures were characterized on the basis of hydrolysis and spectral data, especially NMR evidence. Among them, three compounds, including 3-O-beta-D-glucuropyranosyl oleanolic acid (1), 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl hederagenin (2), and the new compound 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl-30-O-methyl spergulagenate 28-O-beta-D-glucopyranosyl ester (3), are identified for the first time from quinoa seeds. The other isolated saponins have been previously reported in quinoa.

Chenopodium quinoa↗

Antimicrobial furostanol saponins from the seeds of Capsicum annuum L. var. acuminatum.

Three new furostanol saponins named capsicoside E (1), capsicoside F (2), and capsicoside G (5) were obtained from the seeds of Capsicum annuum L. var. acuminatum along with known oligoglycosides (3, 4, and 6-10). On the basis of chemical and spectroscopic analyses, the structures of these new furostanol oligoglycosides were elucidated as 26-O-beta-D-glucopyranosyl-22-O-methyl-5alpha-furost-25(27)-en-2alpha,3beta,22xi,26-tetraol-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside (1), 26-O-beta-D-glucopyranosyl-(25R)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside (2), and 26-O-beta-D-gluco-pyranosyl-(25R)-5alpha-furosta-3beta,22xi,26-triol-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside (5). The isolated saponins showed higher antimicrobial activity against yeasts than against common fungi. Data indicated that the antiyeast activity was related to the combination of the oligosaccharide chain (S1, S2, or S3) with an O-methyl group at R(3) and the presence of a hydroxyl group at the C-2 position.

Anti-Bacterial Agents↗