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At least 757 records · Page 42Linked to original sources
PubMed1999

Effect of six steroidal saponins isolated from anemarrhenae rhizoma on platelet aggregation and hemolysis in human blood.

Six steroidal saponins were isolated from Anemarrhena asphodeloides Bunge (Liliaceae), a traditional chinese medicine, and named anemarrhenasaponin I (An-I), anemarrhenasaponin Ia (An-Ia), timosaponin B-I (TB-I), timosaponin B-II (TB-II), timosaponin B-III (TB-III), and timosaponin A-III (TA-III). The effects of these six compounds on platelet aggregation and hemolysis in human blood were studied. All these compounds provoked remarkable inhibiting effect on platelet aggregation, and activated partial thromboplastin times (APTT) are sensitive to the presence of these six compounds. Using an in vitro system, APTT was delayed with the increment of the concentrations of these six compounds. In these six compounds, only timosaponin A-III appeared a strong effect on hemolysis, and anemarrhenasaponin Ia had a slight effect on hemolysis, other had no effect on hemolysis. These results suggested that these steroidal saponins isolated from Anemarrhena asphodeloides Bunge (Liliaceae) might be used as a novel antithrombotic therapeutic agents in post-myocardial infarction.

Antithrombins↗
PubMed1999

Effects of ginseng saponins on responses induced by various receptor stimuli.

We investigated the effects of four ginseng saponins, ginsenoside-Rb1, -Rg2, -Rg3 and -Ro, on the responses induced by receptor stimulation of various stimuli. Ginsenoside-Rg2 (1-100 microM) reduced the secretions of catecholamines from bovine adrenal chromaffin cells stimulated by acetylcholine and gamma-aminobutyric acid but not by angiotensin II, bradykinin, histamine and neurotensin. In guinea-pig, the ginsenoside also diminished the nicotine-induced secretion of catecholamines from the adrenal chromaffin cells, but it did not affect the muscarine- and the histamine-induced ileum contractions. On the other hand, ginsenoside-Rg3 (1-100 microM) reduced not only the acetylcholine-, the gamma-aminobutyric acid- and the neurotensin-induced secretions but also, at a higher concentration (100 microM), the angiotensin II-, the bradykinin- and the histamine-induced secretions from the bovine chromaffin cells. Furthermore, the saponin (3-100 microM) significantly inhibited the muscarine- and the histamine-induced ileum contractions of the guinea-pig. Ginsenoside-Rb1 and -Ro had no marked effect on their responses. These results strongly suggest that ginsenoside-Rg2 is a potent selective blocker of nicotinic acetylcholine and gamma-aminobutyric acid receptors (ionotropic receptors) and ginsenoside-Rg3 is not only a blocker of ionotropic receptors but also an antagonist of muscarinic or histamine receptors.

Adrenal Glands↗
PubMed1999

Application of high-performance liquid chromatography coupled to nuclear magnetic resonance spectrometry, mass spectrometry and bioassay for the determination of active saponins from Bacopa monniera Wettst.

Reversed-phase high-performance liquid chromatographic separation coupled to (structurally informative) spectroscopic methods like NMR and MS and an efficient bioassay have been used to determine the active compounds from a crude fraction of Bacopa monniera. The fraction containing a mixture of saponins with closely related structures was found to show a significant anthelmintic activity against Caenorhabditis elegans (used as a model test organism for determining anthelmintic activity). The activity was correlated to two dammarane type triterpenoidal saponins containing at least three sugar units. The optimization of separation for 1 mg of the crude sample on column and the sensitivity of on-flow one- and two-dimensional NMR experiments to the high-molecular-mass compounds (M(r) 890-930) has been demonstrated.

Animals↗
PubMed2000

Steroidal saponins from the leaves of Cestrum sendtenerianum.

Five steroidal saponins were isolated from the EtOH extract of Cestrium sendtenerianum (Solanaceae), as confirmed by detailed analysis of their 1H, 13C, and two-dimensional NMR spectral data, and by the results of hydrolytic cleavage. The saponins were revealed to contain three hydroxyl groups at the C-1beta, C-2alpha, and C-3beta positions in the spirostanol skeleton, and to bear a di- or triglycoside at C-3 as the common structural features. One of the compounds, a spirostanol triglycoside, showed weak cytotoxic activity on HL-60 human promyelocytic leukemia cells, with an IC50 value of 7.7 microg/ml.

Carbohydrate Conformation↗
PubMed2000

Triterpenoid saponins from Fagonia cretica.

Four new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia cretica. They were characterized as 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] 27-hydroxy oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester and 3beta-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester. The structures of the saponins were assigned by spectral analyses (FABMS, 1H, 13C NMR, 1H-1H COSY, TOCSY, HMQC and HMBC spectra) and NOE experiments. To the best of our knowledge the genin 3beta hydroxy olean-12-en-27-al-28-oic acid is new.

Magnetic Resonance Spectroscopy↗
PubMed2000

Structural studies of triterpenoid saponins with new acyl components from Quillaja saponaria Molina.

Eight new triterpenoid saponins were isolated from a bark extract of Quillaja saponaria Molina by silica and reverse phase chromatography. The saponins were characterized by spectroscopic data and chemical methods as phytolaccagenic acid, 22beta-hydroxy-quillaic acid, and echinocystic acid substituted with different oligosaccharides at C-3 and C-28. The O-4 of the fucosyl residue in the 28-O-oligosaccharide was substituted with either acetyl, (S)-2-methylbutanoyl, or (3S,4S)-3-hydroxy-4-methylhexanoyl groups.

Carbohydrate Conformation↗
PubMed1994

Triterpene saponins from Myrsine pellucida.

Quercitol, five saponins and 3-O-(6'-O-palmitoyl) beta-D-glucopyranosyl stigmasterol were isolated from the stem bark of Myrisine pellucida. These compounds are described for the first time in this plant and their structures were determined using a combination of 1H and 13C NMR, and mass spectroscopy. The two saponins are new compounds, 3-O-(alpha-L-rhamnopyranosyl (1-->2) beta-D-glucopyranosyl (1-->4) alpha-L-arabinopyranosyl) cyclamiretin A and 3-O-(beta-D-xylopyranosyl) (1-->2) beta-D-glucopyranosyl (1-->4) [beta-D-glucopyranosyl (1-->2)] alpha-L-arabinopyranosyl) cyclamiretin D.

Bolivia↗
PubMed1994

Oleanane-triterpene saponins from Clinopodium chinense var. parviflorum.

From the whole plants of Clinopodium chinense var. parviflorum three new saponins, named clinoposaponins IX-XI, were isolated together with three known saponins and their structures elucidated from spectroscopic data and chemical evidence. Clinoposaponins IX, X and XI were identified as 13 beta,28-epoxy-16 beta,23-dihydroxyolean-11-en-3 beta-yl-beta-D- glucopyranoside,13 beta,28-epoxy-16 beta,23-dihydroxyolean-11-en-3 beta-yl-beta- D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside and 13 beta,28-epoxy-16 beta-hydroxyolean-11-en-3 beta-yl-beta-D-glucopyranosyl- (1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-fucopyranoside.

Carbohydrate Sequence↗
PubMed1994

Triterpenoid saponins from Ardisia crenata.

Two novel triterpenoid saponins, ardisicrenoside A [3 beta-O-(alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->4)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)- 13 beta,28-epoxy-16 alpha,30-oleananediol] and ardisicrenoside B [3 beta-O-(beta-D-xylopyranosyl-(1-->2)-[beta-D- glucopyranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->2)]- alpha-L-arabinopyranosyl)-13 beta,28-epoxy-16 alpha,30-oleananediol] were isolated from the roots of Ardisia crenata. Two known triterpenoid saponins, ardisiacrispins A and B were also isolated from this source. Their structures were determined mainly by 2D NMR (COSY, HOHAHA, HETCOR, HMBC and ROESY) experiments. The aglycones are the new 13 beta,28-epoxy-3 beta,16 alpha,30-oleananetriol for ardisicrenosides A and B.

Carbohydrate Sequence↗
PubMed1994

Anti-inflammatory triterpene saponins of Pithecellobium dulce: characterization of an echinocystic acid bisdesmoside.

A new bisdesmodic triterpenoid saponin, dulcin was isolated from the seeds of Pithecellobium dulce and was identified as 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl]- 28-O-[beta-D-xylopyranosyl (1-->6)-beta-D-glucopyranosyl]-echinocystic acid. The known oleanolic acid saponin PE, oleanolic acid 3-O-beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranoside was also obtained. The structural features were elucidated by a combination of spectroscopic methods and some chemical transformations.

Anti-Inflammatory Agents↗
PubMed1994

Saponins from Barringtonia acutangula.

Three monodesmosidic glucuronide saponins of barringtogenol C, named barringtosides A, B and C have been isolated as their methyl esters from the dried seeds of Barringtonia acutangula. On the basis of chemical and spectral evidence, the structures of these new saponins were elucidated to be as follows: barringtoside A, 3-O-beta-D-xylopyranosyl(1-->3)-[beta-D-galactopyranosyl(1-->2)]-beta-D- glucuronopyranosyl barringtogenol C; barringtoside B, 3-O-beta-D-xylopyranosyl(1-->3)-]beta-D-galactopyranosyl(1-->2)]-beta-D- glucuronopyranosyl-21-O-tigloyl-28-O-isobutyryl barringtogenol C; barringtoside C, 3-O-alpha-L-arabinopyranosyl(1-->3)-[beta-D-galactopyranosyl(1-->2 )]-beta-D - glucuronopyranosyl barringtogenol C.

Carbohydrate Sequence↗
PubMed1994

Bacoside A3--a triterpenoid saponin from Bacopa monniera.

A new triterpenoid saponin, bacoside A3, a constituent of bacosides the saponin mixture of Bacopa monniera, was isolated and characterized. Its structure was established as 3-beta-[O-beta-D-glucopyranosyl(1-->3)-O- [alpha-L-arabinofuranosyl(1-->2) ]O-beta-D-glucopyranosyl)oxy]jujubogenin by chemical and spectral analyses. The cis-isomer of ebelin lactone was also obtained as one of the artefacts of the aglycone and its structure revised.

Carbohydrate Sequence↗
PubMed2001

Application of MS and NMR to the structure elucidation of complex sugar moieties of natural products: exemplified by the steroidal saponin from Yucca filamentosa L.

An approach, using well characterized procedures, is presented that should be of general applicability for the structural elucidation of complex sugar moieties of natural products. The methods used are exemplified by the structure elucidation of a new gitogenin-based steroidal saponin that has a strong leishmanicidal activity similar to preparations used in clinical practice and has been isolated by bioactivity-guided fractionation of the ethanolic extract of Yucca filamentosa L. leaves. The saponin has been characterized as 3-O-((beta-D-glucopyranosyl-(1-->3)- beta-D-glucopyranosy-(1-->2))(alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3))-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranosyl)-25R,5alpha-spirostan-2alpha,3beta-diol.

Biological Products↗
PubMed2002

Triterpenoid saponins and acylated prosapogenins from Harpullia austro-caledonica.

Three new triterpenoid saponins have been isolated from the stem bark of Harpullia austro-caledonica and identified as 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-protoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-16-desoxyprotoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-24-oxo-camelliagenin D. The 21,22-di-O-angeloate esters of protoaescigenin and barringtogenol C were isolated in the acid hydrolysate of the saponin extract together with a new prosapogenin identified as 21beta,22alpha-di-O-angeloyl camelliagenin D. The structures were established using one- and two- dimensional NMR and mass spectrometry.

Acylation↗
PubMed2003

Triterpenoid saponins from Meryta lanceolata.

Four new oleanane-type saponins and a known one were isolated from the leaves and stems of Meryta lanceolata. The new saponins were characterised by spectroscopic means and chemical hydrolysis as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D- glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-6-O-acetyl glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester and 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC and NOE difference studies.

Araliaceae↗
PubMed2003

Bidesmosidic saponins from the fruits of Diploclisia glaucescens.

Chemical investigation of methanol extract of the fruits of Diploclisia glaucescens (Menispermaceae) furnished two new bidesmosidic saponins 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl]phytolaccagenic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]phytolaccagenic acid 28-O-beta-D-glucopyranosyl ester, together with known 3-O-beta-D-glucopyranosylphytolaccagenic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]serjanic acid 28-O-beta-D-glucopyranosyl ester. The last saponin is reported for the first time from the family Menispermaceae.

Acetylation↗
PubMed2003

Further saponins from Taverniera aegyptiaca.

From the saponin fraction of the total methanolic extract of the dried root and stem barks of Taverniera aegyptiaca Boiss, six new triterpenoidal saponins of oleanane type were isolated and identified as 28-methyl serratagenate-3-beta-O-beta-xylopyranosyl (1-->2)-beta-glucopyranoside (2), 28-methyl serratagenate 3-beta-O-alpha-rhamnopyranosyl (1-->2)-beta-glucopyranoside (3), 3beta-O-alpha-rhamnopyranosyl (1-->2) beta-glucopyranosyl-olean-11,13(18)-dien-1beta, 3beta, 22beta-triol (4), 3beta-O-beta-glucopyranosyl (1-->2)-beta-glucuronopyranosylolean-11,13(18)-dien-1beta,3beta,22beta-triol (5), 3beta-O-beta-xylopyranosyl(1-->2)-beta-glucuronopyranosylolean-11,13(18)-dien-1beta,3beta,22beta-triol (6), 3beta-O-alpha-rhamnopyranosyl (1-->2)-beta-glucuronopyranosylolean-11,13(18)-dien-1beta, 3beta, 22beta-triol (7) together with the known oleanolic acid 3-beta-O-beta-glucoside (1). The identification of the isolated compounds was done on the basis of chemical and spectral evidences.

Chromatography↗