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1.
Six new steroidal saponins were isolated from the rhizomes of Smilax sieboldii. Their structures were determined by spectroscopic analysis and hydrolysis to be 3 beta-hydroxy-(25R)-5 alpha-spirostan-6-one (laxogenin) 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]-beta-D-glucopyranoside, laxogenin 3-O-alpha-L-arabinopyranosyl-(1----6)-beta-D-glucopyranoside, 3 beta,27-dihydroxy-(25S)-5 alpha-spirostan-6-one 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]- beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-3 beta,22 xi,26-trihydroxy-(25R)-5 alpha-furostan-6-one 3-O-alpha-L-arabinopyranosyl-(1----6)-beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-3 beta,22 xi,26-trihydroxy-(25R)-5 alpha-furostan-6- one 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]- beta-D-glucopyranoside and (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl- (1----6)]-beta-D-glucopyranoside. The inhibition of cAMP phosphodiesterase by the saponins was evaluated. 相似文献
2.
Two new jatropham derivatives and three new steroidal saponins were isolated from the fresh bulbs of Lilium hansonii, along with previously known compounds. The structures of the new compounds were elucidated, on the basis of spectroscopic data and chemical evidence, and by comparing them with those of known compounds, as (-)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) 5-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranoside, (2S*,4R*)-1-(3-methyl-2-oxo-3-pyrrolinyl)-4-methyl-5-oxo-2-pyrr olidinecarboxyli c acid, 26-O-beta-D-glucopyranosyl-(25R)-5 alpha-furostan-3 beta,22 zeta-diol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, (25R)-5 alpha-spirostan-3 beta,12 alpha-diol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside and (25R)-spirost-5-en-3 beta,12 alpha-diol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, respectively. The stereostructure of jatropham dimer, the plain structure of which was presented previously, was confirmed by X-ray crystallographic analysis. The inhibitory activity on cyclic AMP phosphodiesterase of the steroidal saponins was evaluated. 相似文献
3.
Steroidal glycosides from the bulbs of Lilium dauricum. 总被引:2,自引:0,他引:2
The bulbs of Lilium dauricum yielded 11 compounds, including six new steroidal glycosides. The structures have been determined by spectral analysis and hydrolysis to be (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl-( 1----3)]- beta-D-glucopyranoside, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, (25R)-spirost-5-en-3 beta-ol (diosgenin) 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl- (1----3)]-beta-D-glucopyranoside, (25R)-3 beta,17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside, (25R)-3 beta, 17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L- arabinopyranosyl-(1----3)]-beta-D-glucopyranoside and (20R,22R)-3 beta,20,22-trihydroxy-5 alpha-cholestan-6-one (tenuifoliol) 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. The absolute configurations of C-20 and C-22 of tenuifoliol were further confirmed by detailed analysis of the NOE difference spectrum of the corresponding isopropylidene derivative. Several known compounds were also isolated and identified. 相似文献
4.
Spirostanol saponins of Allium porrum L. 总被引:3,自引:0,他引:3
An investigation of the extracts from bulbs of Allium porrum L. has led to the isolation of four spirostanol saponins. Two of them are new compounds and have been identified as: (25R)-5 alpha-spirostan-3 beta, 6 beta-diol 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O- beta -D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (3) and (25R)-5 alpha-spirostan-3 beta,6 beta-diol 3-O-{O-beta-D-glucopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->2)-O- [beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D- galactopyranoside} (4). The isolated compounds were evaluated for their antifungal activity. 相似文献
5.
Phytochemical examination of the fresh bulbs of Lilium speciosum forma vestale has led to the isolation of a new phenolic glycoside and a new steroidal saponin. The respective structures of the new compounds have been shown by spectral analysis to be 6'-O-feruloylsucrose and (25R,26R)-26-methoxyspirost-5-en-3 beta-o1 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. Several known phenolic glycosides and saponins have also been isolated and identified. 相似文献
6.
The structures of the new steroidal saponins (tentatively named YS-XI, -XII and -XIII) have been isolated from the caudex of Yucca gloriosa and characterized as 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-galactopyranosyl 5 beta- (25R)-spirostan-3 beta, 12 beta-diol, 3-O-beta-D-glucopyranosyl-(1----2)- [beta-D-glucopyranosyl-(1----3)]-beta-D-glucopyranosyl 5 beta- (25R)-spirostan-3 beta, 12 beta-diol and 3-O-beta-D-glucopyranosyl-(1----2)- beta-D-galactopyranosyl 5 beta-(25R)-spirostan-2 beta,3 beta,12 beta-triol, respectively. 相似文献
7.
Steroidal saponins from Smilax lebrunii. 总被引:5,自引:0,他引:5
Two new steroidal saponins, (25 R)-spirostan-3 beta-ol-6-one-3-O-[alpha-L-arabinopyranosyl (1----6)]-beta-D-glucopyranoside and (25 R)-spirostan-3 beta-ol-6-one-3-O-[beta-D-glucopyranosyl(1---4)] [alpha-L-arabinopyranosyl(1----6)]-beta-glucopyranoside, were isolated from the rhizomes of Smilax lebrunii. Their structures have been established by chemical and spectral methods. 相似文献
8.
Barile E Bonanomi G Antignani V Zolfaghari B Sajjadi SE Scala F Lanzotti V 《Phytochemistry》2007,68(5):596-603
Three saponins, named minutoside A (1), minutoside B (2), minutoside C (3), and two known sapogenins, alliogenin and neoagigenin, were isolated from the bulbs of Allium minutiflorum Regel. Elucidation of their structure was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry. The structures of the new compounds were identified as (25R)-furost-2alpha,3beta,6beta,22alpha,26-pentaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (1), (25S)-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranoside (2), and (25R)-furost-2alpha,3beta,5alpha,6beta,22alpha,26-esaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (3). The isolated compounds were evaluated for their antimicrobial activity. All the novel saponins showed a significant antifungal activity depending on their concentration and with the following rank: minutoside B>minutoside C>minutoside A. No appreciable antibacterial activity was recorded. The possible role of these saponins in plant-microbe interactions is discussed. 相似文献
9.
Eight new steroidal glycosides, tentatively named YS-VI, -VII, -VIII, -IX, -X, -XI, -XII and -XIII were isolated from the caudex of Yucca gloriosa along with P-1, YG-2 and YG-3 previously obtained from flowers. The structures of five of these compounds were elucidated as mexogenin 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-galactopyranoside (YS-VI), gloriogenin 3-O-beta-D-glucopyranosyl-(1----2)-[beta- D-glucopyranosyl-(1----3)]-beta-D-glucopyranoside (YS-VII) and 3-O-beta-D-glucopyranosyl-(1----2)-[beta-D-glucopyranosyl)-(1----3)]- beta-D-galactopyranoside (YS-VIII), manogenin 3-O-beta-lycotetraoside (YS-IX) and 3-O-alpha-L-rhamnopyranosyl-beta-lycotetraoside (YS-X), respectively, on the basis of chemical and spectral evidence. 相似文献
10.
From an ethanolic extract of the influorescence of Yucca aloifolia a new spirostanol glycoside has been isolated and characterized as 3-O[(alpha-L-rhamnopyranosyl(1----3)-beta-D-xylopyranosyl(1----2))(beta- D-glucopyranosyl(1----3)-beta-D-glucopyranosyl(1----3)-beta-D-glucopy ranosyl]-25R,5 alpha-spirostan-2 alpha, 3 beta-diol. 相似文献
11.
Four new triterpenoid saponins were isolated from the roots of Gypsophila paniculata and G. arrostii. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques, without having recourse to chemical degradation or modification. The saponins investigated are: 3-O-beta-D-galactopyranosyl-(1----2)-[beta-D-xylopyranosyl-(1----3)]-bet a-D- glucuronopyranosyl quillaic acid 28-O-beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----4)]-alph a- L-rhamnopyranosyl-(1----2)-beta-D-fucopyranoside; 3-O-beta-D-galactopyranosyl-(1----2)-[beta-D-xylopyranosyl-(1----3)]-bet a- D-glucuronopyranosyl quillaic acid 28-O-beta-D-arabinopyranosyl-(1----4)-beta-D-arabinopyranosyl++ +-(1----3)-beta-D- xylopyranosyl-(1----4)-alpha-L-rhamnopyranosyl-(1----2)-beta-D-fucopyran oside; 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucuronopyranosyl gypsogenin 28-O-beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----4)]-alph a- L-rhamnopyranosyl-(1----2)-beta-D-fucopyranoside; 3-O-beta-D-xylopyranosyl-(1----3)-[beta-D-galactopyranosyl-(1----2)]-bet a- D-glucuronopyranosyl gypsogenin 28-O-beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----4)-alpha -L- rhamnopyranosyl-(1----2)-beta-D-fucopyranoside. 相似文献
12.
Steroidal saponins from the rhizomes of Smilax menispermoidea. 总被引:1,自引:0,他引:1
Four steroidal saponins were isolated from the dried rhizomes of Smilax menispermoidea. One of them is new and its structure was established as (25S)spirost-5-en-3 beta,17 alpha-triol-3-O-[alpha-L-rhamnopyranosyl(1----2)] [alhpa-L-rhamnopyranosyl(1----4)]-beta-D-glucopyranoside using spectrometry and chemical methods, as well as comparison with three known steroidal saponins, dioscin, methyl protodioscin and pseudoprotodioscin. 相似文献
13.
E Candra K Matsunaga H Fujiwara Y Mimaki Y Sashida T Yamakuni Y Ohizumi 《Canadian journal of physiology and pharmacology》2001,79(11):953-958
Two steroidal saponins, tigogenin hexasaccharide-1 (TGHS-1, (25R)-5alpha-spirostan-3beta-yl 4-O-[2-0-[3-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-3-0-[4-0- (alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-D- galactopyranoside) and tigogenin hexasaccharide-2 (TGHS-2, (25R)-5alpha-spirostan-3beta-yl 4-O-[2-0-[3-0-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]-3-0-[4-0- (alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl]beta-D-galactopyranoside), were isolated from the fresh bulbs of Camassia cusickii. In murine leukemic L1210 cells, both compounds showed cytotoxicity with an EC50 value of 0.06 microM. The morphological observation revealed that TGHS-1 and TGHS-2 induced shrinkage in cell soma and chromatin condensation, suggesting apoptotic cell death. The cell death was confirmed to be apoptosis by Annexin V binding to phosphatidylserine in the cell membrane and excluding propidium iodide. A typical apoptotic DNA ladder and the cleavage of caspase-3 were observed after treatment with TGHS-1 and TGHS-2. In the presence of both the compounds, cells with sub-G1 DNA content were detected by flow cytometric analysis, indicating that TGHS-1 and TGHS-2 (each EC50 value of 0.1 microM) are the most powerful apoptotic saponins known. These results suggest that TGHS-1 and TGHS-2 induce apoptotic cell death through caspase-3 activation. 相似文献
14.
de Souza AM Lara Lda S Previato JO Lopes AG Caruso-Neves C da Silva BP Parente JP 《Zeitschrift für Naturforschung. C, Journal of biosciences》2004,59(5-6):432-436
Costus spicatus, used in Brazilian traditional medicine to expel kidney stones, contains steroidal saponins with different chemical characteristics. In spite of its popular utilization as potent diuretic, no scientific reports correlate this activity with the chemical constituents of the extract. Therefore, two steroidal saponins (3 beta,22 alpha,25R)-26-(beta-D-glucopyranosyloxy)-2-methoxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside (1) and (3 beta,22 alpha,25R)-spirostan-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside (1a), were isolated from the rhizomes of this plant and their effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that 1 and 1a inhibit specifically the Na+-ATPase activity. 相似文献
15.
Four new pregnane glycosides, stelmatocryptonoside A, B, C, and D (1-4), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral data, the structures of 1-4 were established as 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside; 3beta, 20-dihydroxy-pregn-5-en-20-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->2)-beta-D-digitalopyranoside; 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside; and 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside. This is the first report of pregnane glycosides with sugar chains linked at C-16 of the aglycone. 相似文献
16.
da Silva BP Parente JP 《Zeitschrift für Naturforschung. C, Journal of biosciences》2004,59(1-2):81-85
Two new steroidal saponins were isolated from the rhizomes of Costus spiralis Rosc. Their structures were established as (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (1) and (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (2). Their structural identifications were performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponins were evaluated for anti-inflammatory activity. 相似文献
17.
Triterpene saponins and iridoid glucosides from galium rivale 总被引:2,自引:0,他引:2
Three new glycosides of the oleanene-type triterpenes, rivalosides C-E (1-3), along with three known triterpene saponins, momordin IIb (4) and rivalosides A-B (5-6), and five known iridoid glucosides: monotropein, scandoside, deacetylasperulosidic acid, geniposidic acid and asperulosidic acid, were isolated from aerial parts of Galium rivale. The structures of the new compounds were elucidated by spectral methods and chemical means as 2alpha-acetoxy-3alpha, 19alpha-dihydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl-(1--> 6)-beta-D-glucopyranoside, 2alpha,3alpha, 19alpha-trihydroxy-olean- 12-en-28-oic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside and 3-O-beta-D-glucuronopyranosyl-24-hydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranoside, for rivalosides C-E, respectively. The taxonomic significance of the rivalosides in G. rivale was discussed. 相似文献
18.
Three steroidal saponins, racemosides A (1), B (2) and C (3), were isolated from the methanolic extract of the fruits of Asparagus racemosus, and characterized as (25S)-5beta-spirostan-3beta-ol-3-O-{beta-D- glucopyranosyl (1-->6)-[alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranoside}, (25S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside and (25S)-5beta-spirostan-3beta-ol-3-O-{alpha-L-rhamnopyranosyl-(1-->6)-[alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside}, respectively, by spectrometric analysis and some chemical strategies. 相似文献
19.
Virgaureasaponin 3, a 3,28-bisdesmosidic triterpenoid saponin from Solidago virgaurea. 总被引:1,自引:0,他引:1
A new 3,28-bisdesmosidic triterpenoid glycoside was isolated from the mixture of deacylated saponins from the aerial parts of Solidago virgaurea. The structure of virgaureasaponin 3 was determined as 3-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranosylpolygalacic++ + acid 28-O-beta-D-fucopyranosyl-(1----2)-alpha-L-rhamnopyranosyl-(1----3)-beta -D- xylopyranosyl-(1----4)-alpha-L-rhamnopyranosyl-(1----2)-beta-D-fucopyran oside mainly by various 2D NMR techniques. 相似文献
20.
Four cycloartane-type saponins, kahiricosides II-V (1-4), were isolated from the aerial parts of Astragalus kahiricus of Egyptian origin. Their structures were established as 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetraol-3-O-beta-D-glucopyranoside, 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetraol-3-O-(2'-O-acetyl)-beta-D-glucopyranoside, 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetraol-3-O-(6'-O-acetyl)-beta-D-glucopyranoside, and 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetraol-3-O-beta-D-glucopyranosyl-27-O-beta-D-glucopyranoside based on chemical and spectral evidences. All compounds exhibited very weak cytotoxicity against the A2780 ovarian cancer cell line. 相似文献