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At least 811 records · Page 45Linked to original sources
PubMed2003

Molluscicidal saponins from Sapindus mukorossi, inhibitory agents of golden apple snails, Pomacea canaliculata.

Extracts of soapnut, Sapindus mukorossi Gaertn. (Sapindaceae) showed molluscicidal effects against the golden apple snail, Pomacea canaliculata Lamarck. (Ampullariidae) with LC(50) values of 85, 22, and 17 ppm after treating 24, 48, and 72 h, respectively. Bioassay-directed fractionation of S. mukorossi resulted in the isolation of one new hederagenin-based acetylated saponin, hederagenin 3-O-(2,4-O-di-acetyl-alpha-l-arabinopyranoside)-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranoside (1), along with six known hederagenin saponins, hederagenin 3-O-(3,4-O-di-acetyl-alpha-l-arabinopyranoside)-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranoside (2), hederagenin 3-O-(3-O-acetyl-beta-d-xylopyranosyl)-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranoside (3), hederagenin 3-O-(4-O-acetyl-beta-d-xylopyranosyl)-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranoside (4), hederagenin 3-O-(3,4-O-di-acetyl-beta-d-xylopyranosyl)-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranoside (5), hederagenin 3-O-beta-d-xylopyranosyl-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranoside (6), and hederagenin 3-O-alpha-l-arabinopyranoside (7). The bioassay data revealed that 1-7 were molluscicidal, causing 70-100% mortality at 10 ppm against the golden apple snail.

Animals↗
PubMed2003

Isolation and identification of steroidal saponins in Taiwanese yam cultivar (Dioscorea pseudojaponica Yamamoto).

A new furostanol pentaoligoside and spirostanol tetraoligoside were isolated for the first time from yam tubers (Dioscorea pseudojaponica Yamamoto) from Taiwan, together with four known yam saponins, methyl protodioscin, methyl protogracillin, dioscin, and gracillin. Their structures were characterized as 26-O-beta-D-glucopyranosyl-22alpha-methoxyl-(25R)-furost-5-en-3beta,26-diol, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-([alpha-L-rhamnopyranosyl-(1-->4)]-O-[alpha-L-rhamnopyranosyl-(1-->4)])-beta-D-glucopyranoside, and (25R)-spirost-5-en-3beta-ol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-([alpha-L-rhamnopyranosyl-(1-->4)]-O-[alpha-L-rhamnopyranosyl-(1-->4)])-beta-D-glucopyranoside. The structural identification was performed using LC-MS and 1H and 13C NMR. The methanol extract of yam tubers was fractionated by XAD-2 column chromatography using a methanol/water gradient elution system to yield furostanol and spirostanol glycoside fractions. Preparative high-performance liquid chromatography, employing a C18 column and a mobile phase of methanol/water (69:31, v/v), was used to separate each furostanol glycoside, whereas a mobile phase of methanol/water (79:21, v/v) was used to resolve the individual spirostanol glycosides. The conversions from steroid saponins to diosgenin after acid hydrolysis were around 68 and 90% for furostanol and spirostanol glycosides, respectively.

Chromatography, High Pressure Liquid↗
PubMed2005

Triterpene saponins from barrel medic (Medicago truncatula) aerial parts.

Triterpene saponins from Medicago truncatula aerial parts have been separated and their structures determined by the extensive use of 1D- and 2D-NMR experiments including 1H-1H (DQF-COSY, 1D-TOCSY) and 1H-13C (HSQC, HMBC) spectroscopy along with ESIMS. Fifteen individual compounds were isolated that included seven medicagenic acid and eight zanhic acid glycosides. Additionally, two soyasapogenol B and soyasapogenol E glycosides were identified by MS/MS and TLC. Four medicagenic acid glycosides (5, 11, 12, 14) and eight zanhic acid glycosides (1-4, 6-9) are reported here for the first time. The common feature of M. truncatula aerial part saponins is the (1-->3) linkage between the two glucose units at C-3 of medicagenic and zanhic acids, which is different from that found in alfalfa (Medicago sativa), where this linkage was always (1-->2). This may suggest differences in glucosyltransferases between these two Medicago species.

Glycosides↗
PubMed2005

OSW saponins: facile synthesis toward a new type of structures with potent antitumor activities.

[reaction: see text] OSW saponins, featuring a 16beta,17alpha-dihydroxycholest-22-one aglycon and an acylated beta-D-xylopyranosyl-(1-->3)-alpha-L-arabinopyranosyl residue attached to the 16-hydroxyl group, have recently been discovered from a group of lily plants, which show potent antitumor activities with a novel mechanism of action. This paper describes an aldol approach to the stereoselective construction of the 16alpha,17alpha-dihydroxycholest-22-one structure from 16alpha-hydroxy-5-androsten-17-ones and propionates. Elaboration of the aldol adducts toward OSW-1, involving installation of the isoamyl ketone side chain, inversion of the 16-hydroxyl configuration, and selective protection of the C22-oxy function, has been explored and accomplished. In particular, the present route was found convenient for the synthesis of OSW saponin analogues with a C22-ester side chain. Thus, the 23-oxa-analogue of OSW-1 (40) was prepared starting from the industrial dehydroisoandrosterone (1) in a linear eight-step sequence and in 26% overall yield. Analogues with a variety of modified side chains were prepared, via aldol condensation with propionates of varying length, thiopropionate, and acetate (for preparation of 68-75) or via aminolysis of the 22,16-lactone 26 (for preparation of the 23-N-analogues). Cross metathesis (CM) reaction was also found feasible for modification at the final stage from C22-allyl ester 70. Valuable structure-activity relationships (SAR), together with the practical synthetic approach, have thus been provided to set a new stage for further studies on this new type of antitumor structures.

Antineoplastic Agents↗
PubMed2001

Four new triterpenoid saponins from Conyza blinii.

Three new bisdesmosidic saponins named conyzasaponins A, B, and C (1-3) and one new monodesmosidic saponin, conyzasaponin G (4), were isolated from the aerial parts of Conyza blinii. Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HOHAHA, HMQC, HMBC, and NOESY) and MS studies. Compounds 1-3 share a common prosapogenin, bayogenin 3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside, which is identical with conyzasaponin G (4), and differ in the structures of the ester-linked sugar moieties at C-28. Conyzasaponin A (1) is the 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, conyzasaponin B (2), the 28-O-beta-D-apiofurano- syl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, and conyzasaponin C (3), the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester of the prosapogenin, respectively.

Carbohydrate Sequence↗
PubMed2001

Antisweet saponins from Gymnema sylvestre.

Three new oleanane-type triterpene glycosides (1-3), along with the sodium salt of alternoside II (4), were isolated from an ethanol extract of the leaves of Gymnema sylvestre. The structures of these new saponins were identified as 21 beta-O-benzoylsitakisogenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucuronopyranoside (1), the potassium salt of longispinogenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucuronopyranoside (2), and the potassium salt of 29-hydroxylongispinogenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucuronopyranoside (3). The aglycon of 3, gymnemagenol (3a), was characterized as 3 beta,16 beta,28, 29-tetrahydroxyolean-12-ene. Structure elucidation was accomplished by interpretation of NMR (DQF-COSY, HMQC, and HMBC) results, FABMS, and hydrolysis. Saponin 1 and the sodium salt of alternoside II (4) exhibited antisweet activity.

Adult↗
PubMed2001

Junceosides A-C, new triterpene saponins from Arenaria juncea.

Three novel triterpenoid saponins, junceosides A (1), B (2), and C (3), together with two known saponins have been isolated from the roots of Arenaria juncea. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-glucopyranosyl(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 3-O-beta-D-xylopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3).

Caryophyllaceae↗
PubMed2002

Dammarane-type triterpene saponins from Panax japonicus.

Six new dammarane-type saponins (1-6), together with 11 known saponins (7-17), were isolated from Ye-Sanchi, the underground part of Panax japonicus collected in the South of Yunnan Province, China. Their structures were elucidated by chemical and spectroscopic means.

China↗
PubMed2002

New acylated triterpene saponins from Silene fortunei that modulate lymphocyte proliferation.

Three new acylated triterpene saponins 1-3, with a quillaic acid as aglycon, were isolated from the roots of Silene fortunei together with a known phytoecdysteroid (20-hydroxyecdysone). The compounds were characterized mainly by a combination of 2D NMR techniques, mass spectrometry, and chemical methods. Saponins 1-3, jenisseensosides C and D (4, 5), and 6 (deacylated form of 2/3 and 4/5) were found to stimulate the proliferation of the Jurkat tumor cell lines at low concentration. At high concentration, 2/3 and 4/5 inhibited the proliferation of the cells and suggested the induction of apoptosis.

Acetylation↗
PubMed2003

Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia.

Two new oleanane-type triterpene saponins, adianthifoliosides A (1) and B (2), were isolated from a 95% ethanolic extract of roots of Albizia adianthifolia. Their structures were elucidated mainly by using a combination of 600 MHz 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and by FABMS and HRESIMS. Compounds 1 and 2 were characterized as glycosides of acacic acid acylated by an o-hydroxybenzoyl unit. The crude saponin mixture (CSM), compounds 1 and 2 together with 3 and 4 (prosapogenins obtained from the mild alkaline hydrolysate of the CSM), were evaluated for immunomodulatory activity on the Jurkat T cell line and for hemolytic property against sheep erythrocytes. Compound 2 and, to a lesser extent, 1 and 3 were found to exhibit a dose-dependent immunomodulatory effect in the concentration range 10(-2)-10 microM, whereas 4 showed a lymphoproliferative activity in the same concentration range. Among the compounds tested, only 1 and 2 were found to be hemolytic.

Acetylation↗
PubMed2003

Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production.

Two new triterpenoid saponins (1 and 2) were isolated from the stem bark of Cussonia bancoensis together with the known stigmasterol, ursolic acid, 23-hydroxyursolic acid (3), and 3beta-hydroxylup-20(29)-en-28-oic acid. On the basis of their spectroscopic data and on chemical transformations, the structures of the new saponins have been established as 3-O-(alpha-Ll-arabinopyranosyl)-23-hydroxyursolic acid (1) and 3-O-(beta-D-glucopyranosyl)-23-hydroxyursolic acid (2). In a nitric oxide (NO)-production bioassay, compound 3 exhibited significant NO inhibitory activity, while compounds 1 and 2 were less potent than 3.

Animals↗
PubMed2004

Oleanane saponins from Sanicula elata var. chinensis.

Eleven new oleanane-type triterpenoid saponins, saniculasaponins I-XI (1-11), and a known saponin, sandrosaponin IX (12), were isolated from the methanol extract of the whole plants of Sanicula elataHam. var. chinensis Makino. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

Chromatography, High Pressure Liquid↗
PubMed2004

Hydrocotylosides I-VII, new oleanane saponins from hydrocotylesibthorpioides.

Seven new oleanane-type triterpenoid saponins, hydrocotylosides I-VII (1-7), and one known saponin, udosaponin B (8), were isolated from the methanol extract of the whole plants of Hydrocotyle sibthorpioides.The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

Apiaceae↗
PubMed2004

Acetals of three new cycloartane-type saponins from Egyptian collections of Astragalus tomentosus.

Three new cycloartane-type saponin ethyl acetals, deacetyltomentoside I (2), tomentoside III (3), and tomentoside IV (4), were isolated along with the known acetal tomentoside I (1) from the aerial parts of Astragalus tomentosus of Egyptian origin. The saponins from which the acetals are most probably derived are also new compounds. The structures of the acetals were established as 6alpha-hydroxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-beta-d-xyloside (2), 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-(4'-trans-2-butenoyl)]xyloside (3), and 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-glucopyranosyl(1 --> 2)]-beta-d-xyloside (4), by detailed spectroscopic and chemical studies.

Acetals↗
PubMed2004

Five new Ocotillone-type saponins from Gynostemma pentaphyllum.

Five new ocotillone-type saponins, gynosides A-E (1-5), along with 10 known dammarane-type saponins, were isolated from the aerial parts of Gynostemma pentaphyllum. The structures of these new compounds were determined by NMR analysis and acid hydrolysis. The structure and stereochemistry of gynoside A (1) were confirmed by X-ray crystallography.

Crystallography, X-Ray↗
PubMed2004

Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum.

Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-3-O-acetyl-beta-D-fucopyranoside (2), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (3), and 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-[3-O-acetyl-beta-D-quinovopyranosyl-(1-->4)]-beta-D-fucopyranoside (4).

Caryophyllaceae↗
PubMed2005

Cytotoxic steroidal saponins from the rhizomes of Asparagus oligoclonos.

Two new steroidal saponins, aspaoligonins A (2) and B (3), were isolated from the methanolic extract of the rhizomes of Asparagus oligoclonos together with a known spirostanol saponin, asparanin A (1). Aspaoligonins A and B were characterized as (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranoside and (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-alpha-L-rhamnopyanosyl (1-->4)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranoside, respectively, by spectrometric analyses including HRFABMS and 2D NMR. Compounds 1-3 were cytotoxic against five human tumor cell lines with IC50 values of 2.05-2.84 microg/mL.

Antineoplastic Agents, Phytogenic↗
PubMed2005

Silenorubicosides A-D, triterpenoid saponins from Silene rubicunda.

Four novel triterpenoid saponins, silenorubicosides A-D (1-4), together with four known saponins were isolated from the roots of Silene rubicunda. Their structures were established on the basis of spectroscopic analysis, including extensive 1D and 2D NMR (DQF-COSY, TOCSY, HETCOR, HMBC, and phase-sensitive NOESY) studies and chemical degradation.

Carbohydrate Sequence↗