Two new triterpene saponins from Eryngium campestre

Two new triterpene saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-angeloyl-R1-barrigenol (1) and 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-beta,beta-dimethylacryloyl-A1-barrigenol (2), were isolated from the roots of Eryngium campestre (Apiaceae). Their structures were established mainly by 2D NMR techniques and mass spectrometry.     

Two new monodesmosidic triterpene saponins from Gypsophila oldhamiana

Two new monodesmosidic triterpene saponins were isolated from the roots of Gypsophila oldhamiana (Caryophyllaceae). Their structures were elucidated on the basis of spectral data to be quillaic acid, alpha-L-arabinopyranosyl-(1-->4)-alpha-L-arabinopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (1), and vaccaric acid, beta-D-glucopyranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (2). Compound 1 showed a significant enhancement of granulocyte phagocytosis in vitro.     

Phytoecdysteroids from the roots of Achyranthes bidentata Blume

Two new phytoecdysteroids, (25S)-20,22-O-(R-ethylidene)inokosterone and 20,22-O-(R-3-methoxycarbonyl)propylidene-20-hydroxyecdysone, together with six known phytoecdysteroids 3-8 were isolated from the roots of Achyranthes bidentata Blume. The new structures were established on the basis of spectroscopic studies and chemical evidences. The absolute configuration at C-25 in the structure of known compound 3 was determined by chemical and spectroscopic means.     

Antitumor triterpene saponins from Anemone flaccida

A new triterpenoid saponin, 3-O-[（6′-butyryl）-β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-（1→4）-β-D-glucopyranosyl-（1→6）-β-D-glucopyranosyl] oleanolic acid, as well as three known triterpenoid saponins were isolated from the rhizomes of Anemone flaccida. Their structures were elucidated by spectroscopic methods. These compounds showed significant antitumor activities.     

Supercritical fluid extraction of ecdysterone from the roots of Achyranthes bidentata BL

Ecdysterone has been found in a great many plants and animals and has some valuable pharmaceutical properties. The present study was conducted to investigate optimal conditions for the extraction of the compound by supercritical fluid extraction from the roots of Achyranthes bidentata BL. An orthogonal array design (OAD), OA(9)(3(4)), was employed as a chemometric method for optimization of the extraction of ecdysterone from the herbal medicine. Four parameters, namely, pressure and temperature of the supercritical fluid, the dynamic extraction time, and the flow rate of dimethyl sulfoxide, were studied and optimized by a three-level OAD. Determinations of the extracts were performed by high-performance liquid chromatography. The effects of the parameters were studied using analysis of variance. The results shown that the yield of ecdysterone could be influenced by the four parameters to a similar degree. The yield for DMSO-modified supercritical CO(2) was in the range from 0.65 to 1.03 mg/g under the selected conditions. In comparison with methanol-modified supercritical CO(2 )and Soxhlet extraction, a higher yield was obtained when DMSO-modified supercritical CO(2) was used.     

Cytotoxic triterpene saponins from the mangrove Aegiceras corniculatum

Using various chromatographic separations, sixteen compounds, including one new triterpene saponin named aegicoroside A (1), were isolated from the leaves of the Vietnamese mangrove Aegiceras corniculatum. Their structures were determined by spectroscopic methods such as 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities of the isolated compounds against MCF7 (breast), HCT116 (colon), B16F10 (melanoma), and A549 (adenocarcinoma) cancer cell lines were also evaluated. Strong cytotoxicity was observed for sakurasosaponin (2) against all four cancer cell lines and for sakurasosaponin methyl ester (3) against MCF7, A549, and HCT116 cell lines with IC₅₀ values ranging from 2.89 ± 0.02 to 9.86 ± 0.21 μM.     

Oleanolic triterpene saponins from the roots of Panax bipinnatifidus

Ten oleanane-type saponins (1-10), including three new compounds, namely bifinosides A-C (1-3), were isolated from the roots of Panax bipinnatifidus SEEM. Their structures were elucidated on the basis of chemical and spectroscopic methods.     

Structural study on a bioactive fructan from the root of Achyranthes bidentata Blume

The structure of a saccharide component (Abs),with pronounced activity of improving immunity system,isolated from the root of Achyranthes bidentata Blume,a traditional Chinese herbal medicine,was studied.Based on 13C NMR,HPLC,and methylation analyses,Abs was shown to be a mixture of short-chain fructans with an average dp of 8,containing more (2→6) than (2→1) linked β-D-fructofuranosyl residues,with branching at O-6 or O-1 of 18% of the D-fructofuranoeyl residues.     

Triterpenes and triterpene saponins from the stems of Akebia trifoliata

To characterize the stems of Akebia trifoliata chemically, a detailed phytochemical examination was carried out on A. trifoliata stems, with particular attention to the triterpene and triterpene saponin constituents, and resulted in the isolation of three new triterpenes (1-3) and three new triterpene saponins (11-13), together with seven known triterpenes (4-10) and 12 known triterpene saponins (14-25). The structures of the new compounds were determined on the basis of spectroscopic analysis, including two-dimensional NMR spectroscopic data, and the results of hydrolysis. Four saponins (22-25), which were obtained in good yields and were not isolated from Akebia quinata stems, are concluded to be applicable as marker compounds in chemically distinguishing between A. trifoliata and A. quinata by conventional TLC examination. To the best our knowledge, the current work is the first chemical investigation of A. trifoliata.     

Three new triterpene saponins from the seeds of Aesculus chinensis

Three new triterpenoid saponins were isolated from the seeds of Aesculus chinensis, and characterized as 22-tigloylprotoaescigenin 3-O-[beta-D-glucopyranosyl (1-->2)] [beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranosiduronic acid (escin IVg, 1), 22-angeloylprotoaescigenin 3-O-[beta-D-glucopyranosyl (1-->2)] [beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranosiduronic acid (escin IVh, 2) and 16-angeloyl-21-acetylprotoaescigenin 3-O-[beta-D-glucopyranosyl (1-->2)] [beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranosiduronic acid (escin VIb, 3), together with two known compounds, escin IIIa (4) and desacylescin 1 (5). Their structures were established on the basis of spectroscopic and chemical evidence.     

Anti-platelet aggregation triterpene saponins from the galls of Sapindus mukorossi

Bioassay-directed fractionation of an ethanolic extract of the galls of Sapindus mukorossi has resulted in the isolation of two new tirucallane-type triterpenoid saponins, sapinmusaponins Q (1) and R (2), along with three known oleanane-type triterpenoid saponins (3-5). Their structures were elucidated on the basis of spectroscopic analysis and chemical hydrolysis. Biological evaluation showed that both sapinmusaponins Q and R demonstrated more potent anti-platelet aggregation activity than aspirin.     

Two new triterpenoid saponins from Platycodon grandiflorum.

Two new triterpenoid saponins, platycoside D [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D- glucopyranosyl-2 beta, 3 beta, 16 alpha, 23-tetrahydroxyolean-12-ene-28-oic acid 28-O-beta-D- apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnop yranosyl- (1-->2)-alpha-L-arabinopyranoside] and platycoside E [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosyl-2 beta,3 beta,16 alpha,23,24-pentahydroxyolean-12-ene-28-oic acid 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alp ha-L- rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside] were isolated from the roots of Platycodon grandiflorum. Structural determination is based on spectral and chemical evidence.     

Bioactive saponins and glycosides. XXV. Acylated oleanane-type triterpene saponins from the seeds of tea plant (Camellia sinensis)

Seven new acylated oleanane-type triterpene oligoglycosides, theasaponins A(4) (1), A(5) (2), C(1) (3), E(8) (4), E(9) (5), G(1) (6), and H(1) (7), were isolated from the seeds of Japanese tea plant (Camellia sinensis). The structures of 1-7 were elucidated on the basis of chemical and physicochemical evidence.     

Six new dammarane-type triterpene saponins from the leaves of Panax ginseng

Six new minor saponins, together with known ginsenosides, were isolated from the leaves of Panax ginseng. The new saponins were named as ginsenoside-Rh5, -Rh6, -Rh7 -Rh8, -Rh9 and -Rg7, and their structures were elucidated on the basis of chemical and physicochemical evidence to be as follows: ginsenoside-Rh5: 3beta,6alpha,12beta,24zeta-tetrahydroxy-dammar-20(22),25-diene 6-O-beta-D-glucopyranoside (1), -Rh6: 3beta,6alpha12beta,20(S)-tetrahydroxy-25-hydroperoxy-dammar-23-ene 20-O-beta-D-glucopyranoside (2), -Rh7: 3beta,7beta,12beta,20(S)-tetrahydroxy-dammar-5,24-diene 20-O-beta-D-glucopyranoside (3), -Rh8: 3beta,6alpha,20(S)-trihydroxy-dammar-24-ene-12-one 20-O-beta-D-glucopyranoside (4), -Rh9: 3beta,6alpha,20(S)-trihydroxy-12beta,23-epoxy-dammar-24-ene 20-O-beta-D-glucopyranoside (5) and -Rg7: 3-O-beta-D-glucopyranosyl 3beta,12beta,20(S),24(R)-tetrahydroxy-dammar-25-ene 20-O-beta-D-glucopyranoside (6).     

Acetylated triterpene saponins from the Thai medicinal plant, Sapindus emarginatus

From the pericarps of Sapindus emarginatus (Sapindaceae), three new acetylated triterpene saponins were isolated together with hederagenin and five known triterpene saponins, as well as one known sweet acyclic sesquiterpene glycoside, mukurozioside IIb. The structures of new compounds were elucidated as hederagenin 3-O-(2-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside, 23-O-acetyl-hederagenin 3-O-(4-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside and oleanolic acid 3-O-(4-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside by chemical and spectroscopic data.     

Structure of triterpene saponins from the roots ofGlycyrrhiza echinata

Conclusions On the basis of a physicochemical study of the saponins ofGlycyrrhiza echinata L., their molecular weights have been determined. It has been found that the two saponins are biosides of macedonic acid (saponin A) and echinatic acid (saponin B), the carbohydrate moieties of which contain L-rhamnose and D-glucuronic acid.In both saponins, the L-rhamnose is bound directly to the aglycones.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 1, pp. 17–19, 1969     

Two new furostanol saponins from Tribulus terrestris L.

<正>Two new furostanol glycoside,26-O-β-D-glucopyranosyl-(25S)-5α-furost-3β,22α,26-triol-3-O-β-D-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside(1) and 26-O-β-D-glucopyranosyl-(25S)-5α-furost-20(22)-en-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(2) were isolated fromthe fruits of Tribulus terrestris L.The structures of two new furostanol saponins were elucidated by spectroscopic methods.     

Two new saponins from Zygophyllum atriplicoides

Phytochemicals investigation of the whole plant of Zygophyllum atriplicoides resulted in the isolation of two new triterpenoidal saponins together with a known compound. The structure of the new compounds atriplicosaponin A (1) and atriplicosaponin B (2) were established as 3-O-[alpha-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]-hederagenin and 27 alpha-hydroxyurs-12-ene-3-O-[beta-D-glucopyranosyl(1-->4)(2-O-sulpho)-beta-D-quinovopyranoside] and known compound was identified as 3-O-[beta-D-glucopyranosyl]-beta-sitosterol. The structure elucidations of the compounds were based primarily on 1D and 2D-NMR analysis, including COSY, HMBC and HMQC correlations.     

Two triterpenoid saponins from Neonauclea sessilifolia

From the dried roots of Neonauclea sessilifolia (Rubiaceae), two new triterpenoid saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-quinovopyranosyl quinovic acid (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-quinovopyranosyl pyrocincholic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), were isolated, together with five known saponins. The structures of the new saponins were determined by spectroscopic and chemical means.