Four new and three known oleanane-type saponins have been isolated from the methanolic extract of Phryna ortegioides, a monotypic and endemic taxon of Caryophyllaceae.The structures of the new compounds were determined as gypsogenic acid 28-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (2), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-]-β-d-glucopyranosyl ester (3), 3-O-α-l-arabinofuranosyl-16α-hydroxyolean-12-en-23,28-dioic acid-28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (4). Their structures were established by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. Noteworthy, none of isolated compounds possesses as aglycone moiety gypsogenin, considered a marker of Caryophyllaceae family.The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. Only compound 6 showed a weak activity against A375 and DeFew cell lines with IC50 values of 77 and 52 μM, respectively. None of the other tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number. 相似文献
Two new saponins beshornin and beshornoside have been isolated from the methanolic extract of Beshorneria yuccoides leaves and their structures elucidated. Beshornin is 3-O-[α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl- (1 → 2)-[α-l-rhamnopyranosyl-(1 -+ 4)-P-D-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d- galactopyranosyl-(25R)-5α-spirostan-3β-ol, whereas beshornoside is 3-O-[α-l-rhamnopyranosyl-(1 → 4)- β-d)-glycopyranosyl-(1 → 2)]-[α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl- (1 → 4)-β-d-galactopyranosyl 26-O-[β-d]-glucopyranosyl-(25R)-5α-furostan-3β,22α,26-triol. 相似文献
Two new saponins, agavasaponin E and agavasaponin H have been isolated from the methanolic extract of Agave americana leaves and their structures elucidated. Agavasaponin E is 3-O-[β-d-xylopyranosyl-(1→2glc1)-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3glc 1)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-α-d-galactopyranosyl]-(25R)-5α-spirostan-12-on-3β-ol, whereas agavasaponin H is 3-O-[β-d-xylopyranosyl-(1→2 glc 1)-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3 glc 1)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl]-26-O-[β-d-glucopyranosyl]-(25R)-5α-furostan-12-on-3β,22α,26-triol. 相似文献
Partial, acid hydrolysis of the extracellular polysaccharide from Xanthomonas campestris gave products that were identified as cellobiose, 2-O-(β-d-glucopyranosyluronic acid)-d-mannose, O(β-d-glucopyranosyluronic acid)-(1→2)-O-α-d-mannopyranosyl-(1→3)-d-glucose, O-(β-d-glucopyranosyluronic acid)-(1→2)-O-α-d-mannopyranosyl-(1→3)-[O-β-d-glucopyranosyl-(1→4)]-d-glucose, and O-(β-d-glucopyranosyluronic acid)-(1→2)-O-α-d-mannopyranosyl-(1→3)-[O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-d-glucose. This and other evidence supports the following polysaccharide structure (1) which has been proposed independently by Jansson, Kenne, and Lindberg: 相似文献
Two new saponins, yuccoside C and protoyuccoside C, have been isolated from the methanolic extract of Yucca filamentosa root and their structures elucidated. Yuccoside C is 3-O-[α-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, whereas protoyuccoside C is 3-O-[α-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosy]-(25S)-5β-furostan-3β,22α,26-triol. 相似文献
8-Methoxycarbonyloctyl 2-azido-4,6-O-benzylidene-2-deoxy-β-d-mannopyranoside reacted with 2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl bromide to give a disaccharide from the which the glycosyl-acceptor 8-methoxycarbonyloctyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,4,-di-O-acetyl-α-l-rhamnopyranosyl)-β-d-manno pyranoside (19) was obtained. This glycosyl-acceptor with 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl chloride to give trisaccharide derivative 22 and with 2,3,6-tri-O-(α-2H2)benzyl-4-O-(2,3,4,6-tetra-O-(α-2H2)benzyl-α-d-glucopyranosyl)-α-d-glucopyranosyl chloride to give tetrasaccharide derivative 29. Deblocking of 22 yielded 8-methoxycarbonyloctyl O-(α-d-glucopyranosyl)-(1→3)-O-α-l-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-d-mannopyranoside and deblocking of 29 8-methoxycarbonyloctyle O-α-d-glucopyranosyl-(1→4)-O-α-d-glucopyranosyl-(1→3)-O-α-l-rhamnopyranosyl- (1→3)-2-acetamido-2-deoxy-β-d-mannopyranoside. Both oligosaccharides represent the “repeating unit” of the O-specific chain of the lipopolysaccharide from Aeromonas salmonicida. 相似文献
Five new steroidal saponins were isolated from the fruits of Tribulus terrestris. Their structures were fully established by spectroscopic and chemical analysis as (23S,25S)-5α-spirostane-24-one-3β,23-diol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (1), (24S,25S)-5α-spirostane-3β,24-diol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (2), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-2α,3β,22α,26-tetraol-3-O-{β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside} (3), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-en-2α,3β,26-triol-3-O-{β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside} (4), and 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-12-one-22-methoxy-3β,26-diol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (5). The isolated compounds were evaluated for cytostatic activity against HL-60 cells. 相似文献
Five triterpenoid saponins isolated from the flowers, the mature fruits and the leaves of Fatsia japonica were identified as 3-O-[β-d-glucopyranosyl(1→4)-β-d-glucopyranosyl]-hederagenin (1), 3-O-[β-d-glucopyranosyl-(1→4)-α-l-arabinopyranosyl]-oleanolic acid (2), 3-O-[α-l-arabinopyranosyl]-hederagenin (3), 3-O-[β-d-glucopyranosyl]-hederagenin (4) and 3-O-[β-d-glucopyranosyl(1→4)-α-l-arabinopyranosyl]-hederagenin (5). The saponins 1 and 2 are new, naturally occurring, triterpenoid saponins. The distribution of the five saponins in three parts of the plant was investigated. Saponins 2, 3 and 5 were present in the flowers, saponins 1, 3, 4 and 5 were in the mature fruits and saponins 2, 3, 4 and 5 were in the leaves. 相似文献
A bioassay-guided phytochemical analysis of the triterpene saponins from under ground parts of Gypsophila arrostii var. nebulosa allowed the isolation of two triterpene saponins; nebuloside A, B based on gypsogenin and quillaic acid aglycone. Two new oleanane type triterpenoid saponins (nebuloside A, B) and three known saponins (1–3) were isolated from the root bark of Gypsophila arrostii var. nebulosa. The structures of the two new compounds were elucidated as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside A) and 3-O-β-d-xylopyranosyl-(1→3)-[β-d-galactopyranosyl(1→3)-β-d-galactopyranosyl-(1→2)]-β-d-glucuronopyranosyl gypsogenin 28-O-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside B), on the basis of extensive spectral analysis and chemical evidence. Nebuloside A and B showed toxicity enhancing properties on saporin a type-I RIP without causing toxicity by themselves at 15 μg/mL. 相似文献
The two purple-membrane glycolipids O-β-d-glucopyranosyl- and O-β-d-galactopyranosyl-(1→6)-O-α-d-mannopyranosyl-(1→2)-O-α-d-glucopyranosyl-(1→1)-2, 3-di-O-phytanyl-sn-glycerol were prepared by coupling O-(2,3,4-tri-O-acetyl-α-d-mannopyranosyl)-(1→2)-O-(3,4,6-tri-O-acetyl-α-d-glucopyranosyl)-(1→1)-2, 3-di-O-phytanyl-sn-glycerol (9) with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide or 2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl bromide, respectively, followed by deacetylation. The glycolipid sulfate O-(β-d-glucopyranosyl 3-sulfate)-(1→6)-O-α-d-mannopyranosyl-(1→2)-O-α-d-glucopyranosyl-(1→1)-2,3-di-O-phytanyl-sn-glycerol was prepared by coupling of 9 with 2,4,6-tri-O-acetyl-3-O-trichloroethyloxycarbonyl-α-d-glucopyranosyl bromide in the presence of Hg(CN)2/HgBr2 followed by selective removal of the 3?-trichloroethyloxycarbonyl group, sulfation of HO-3?, and deacetylation. The suitably protected key-intermediate 9 could be prepared by two distinct approaches. 相似文献
Four cycloartane- (hareftosides A–D) and oleanane-type triterpenoids (hareftoside E) were isolated from Astragalus hareftae along with fifteen known compounds. Structures of the compounds were established as 3,6-di-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (1), 3,6,24-tri-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (2), 3-O-β-d-xylopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),25(S)-epoxycycloartane (3), 16-O-β-d-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), 3-O-[β-d-xylopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucuronopyranosyl]-soyasapogenol B (5) by the extensive use of 1D- and 2D-NMR experiments along with ESI-MS and HR-MS analyses. 相似文献
The structure of Entada saponin (ES)-III, one of the main saponins of Entada phaseoloides bark, was established to be 3-O-[β-d-xylopyranosyl (1 → 2)-α-l-arabinopyranosyl (1 → 6)] [β-l-glucopyranosyl (1 → 4)]-2-acetamido-2-deoxy-β-l-glucopyranosyl-28-O-[β-l-apiofuranosyl (1 → 3)-β-d-xylopyranosyl (1 → 2)] [(2-O-acetoxyl)-β-d-glucopyranosyl-(1 → 4)] (6 − O(R) (−)2,6-dimethyl-2-trans-2,7-octadienoyl)-β-d-glucopyranosyl echinocystic acid. 相似文献
Four novel 3,28-O-bisglycosidic triterpenoid saponins were isolated from the mature fruits of F. japonica. They were characterized as the 28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-β- d-glucopyranosides of 3-O-α-l-arabinopyranosyl echinocystic acid, 3-O-α-l-arabinopyranosyl hederagenin, 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosyl oleanolic acid and 3-O-β- d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosyl hederagenin respectively. 相似文献
4′-O-β-d-Glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure–activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-β-d-glucopyranoside (1), quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. 相似文献
Two new acylated triterpenoid saponins named pendulaosides A and B as well as the known phenolic compounds methyl gallate, gallic acid, 1,2,3,6-tera-O-galloyl-β-d-glucose and 1,2,3,4,6-penta-O-galloyl-β-d-glucose, were isolated from the seeds of Harpullia pendula. The structures of pendulaosides A and B were determined using extensive 1D and 2D NMR analysis and mass spectrometry as well as acid hydrolysis, as 3-O-β-d-glucopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→3)]-β-d-glucuronopyranosyl-22-O-angeloyl-3β,16α,22α,24β,28-pentahydroxylolean-12-ene and 3-O-β-d-glucopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→3)]-β-d-glucuronopyranosyl-16-O-(2-methylbutyroyl)-3β,16α,22α,24β,28-pentahydroxylolean-12-ene, respectively. To the best of our knowledge the two triterpene parts 22-O-angeloyl-3β,16α,22α,24β,28-pentahydroxylolean-12-ene and16-O-(2-methylbutyroyl)-3β,16α,22α,24β,28-pentahydroxylolean-12-ene have never been characterized before. The two isolated saponins were assayed for their in-vitro cytotoxic activity against the three human tumor cell lines HepG2, MCF7 and PC3. The results showed that pendulaoside A exhibited moderate activity on PC3 cell line with IC50value equal to 13.0 μM and weak activity on HepG2 cell line with IC50 value equal to 41.0 μM. Pendulaoside B proved to be inactive against the three used cell lines. 相似文献
3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. One-pot glycosylation and ‘inverse procedure’ technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl]oleanolic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester (3), 3-O-[α-l-rhamnopyranosyl]oleanolic acid 28-O-[α-l-rhamnopyranosyl- (1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester (4), 3-O-[α-l-rhamnopyranosyl]oleanolic acid 28-O-[α-l-rhamnopyranosyl] ester (5), and 3-O-[α-l-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(α-l-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. 相似文献
Two new tridesmosidic cycloartane-type triterpene glycosides (1 and 2) were isolated from the methanolic extract of the roots of Astragalus brachycalyx FISCHER (A. brachycalyx) along with ten (3–12) known cycloartane-type triterpene glycosides. Structures of the new compounds were established as 3-O-β-d-xylopyranosyl-6-O-β-d-glucopyranosyl-16-O-β-d-glucopyranosyl-3β,6α,16β,24(S)-25-pentahydroxycycloartane (1), 3-O-[α-l-arabinopyranosyl-(1→2)-β-d-xylopyranosyl]-6-O-β-d-glucopyranosyl-16-O-β-d-glucopyranosyl-3β,6α,16β,24(S)-25-pentahydroxycycloartane (2), by using 1D and 2D-NMR techniques and mass spectrometry.In vitro immunomodulatory effects and hemolytic activities of the new saponins (1 and 2) and acetylated form of 1 (1a) were studied together with the BuOH and MeOH extracts of Astragalus brachycalyx. The results have proven that tridesmosidic Astragalus cycloartanes are noteworthy immunomodulatory compounds via induction of cytokine production, namely IL-2 and IFN-γ. The test compounds also resulted slight hemolysis at very high doses substantiating a safer profile compared to the positive control QS-21. 相似文献
O-β-d-Galactopyranosyl-(1→4)-O-[α-l-fucopyranosyl-(1→3)]-d-glucose has been synthesised by reaction of benzyl 2,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-d-galactopyranosyl)-β-d-glucopyranoside with 2,3,4-tri-O-benzyl-α-l-fucopyranosyl bromide in the presence of mercuric bromide, followed by hydrogenolysis. Benzylation of benzyl 3′,4′-O-isopropylidene-β-lactoside, via tributylstannylation, in the presence of tetrabutylammonium bromide or N-methylimidazole, gave benzyl 2,6-di-O-benzyl-4-O-(6-O-benzyl-3,4-O-isopropylidene-β-d-galactopyranosyl)-β-d-glucopyranoside (6). α-Fucosylation of 6 in the presence of tetraethylammonium bromide provided either benzyl 2,6-di-O-benzyl-4-O-[6-O-benzyl-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-l-fucopyransoyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (13, 73%) or a mixture of 13 (42%) and benzyl 2,6-di-O-benzyl-4-O-[6-O-benzyl-3,4,-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-l-fucopyranosyl)-β-d- galactopyranosyl-3-O-(2,3,4-tri-O-benzyl-α-l-fucopyranosyl)-β-d-glucopyranoside (16, 34%). α-Fucosylation of 13 in the presence of mercuric bromide and 2,6-di-tert-butyl-4-methylpyridine gave 16 (73%). Hydrogenolysis and acid hydrolysis of 13 and 16 afforded O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→4)-d-glucose and O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→4)-O-[α-l-fucopyranosyl-(1→3)]-d-glucose, respectively. 相似文献
Three undescribed flavonol triglycosides, rhamnetin-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside (champaluangoside A), rhamnetin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-galactopyranoside (champaluangoside B) and rhamnocitrin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside (champaluangoside C), were isolated from Magnolia utilis in addition to eleven known compounds; quercetrin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside, oxytroflavoside G, magnoloside A, magnoloside M, magnoloside D, manglieside A, manglieside B, 1,2-di-O-β-d-glucopyranosyl-4-allylbebzene, syringrin, benzyl β-d-allopyranoside and (+)-syringaresinol-O-β-d-glucopyranoside. The structure elucidation of these compounds was based on analyses of physical and spectroscopic data. 相似文献
The structure of microphyllic acid, the main glycosidic acid from the ether soluble resin of Convolvulus microphyllus has been elucidated as the O-α-l-rhamnopyranosyl-(1 → 6)-[O-α-l-rhamopyranosyl -(1 → 4)]-O-β-d-glucopyranosyl-(1 → 3)-O-α-l5-rhamnopyranosyl-(1 → 3)-O-β-d-fucopyranoside of 11-hydroxypalmitic acid, using mainly GLC and mass spectrometry of the derivatized sugars. 相似文献