共查询到20条相似文献,搜索用时 125 毫秒
1.
Mariateresa Maldini Paola Montoro Ireneusz Kapusta Wieslaw Oleszek Sonia Piacente Cosimo Pizza 《Chromatographia》2009,70(11-12):1621-1626
Six secondary metabolites from the methanolic extract of Sweetia panamensis (Fabaceae) bark were isolated and characterised. Along with the pyrones desmethylangonine β-d-O-glucopyranoside and desmethylangonine β-d-O-glucopyranosyl-(1→6)-O-β-d-glucopyranoside, already reported in this species, 5-O-caffeoylquinic acid (chlorogenic acid), 4-O-caffeoylquinic acid, 3-O-caffeoylquinic acid and the isoflavonoid 5-O-methylgenistein 7-O-β-d-glucopyranoside were isolated for the first time from S. panamensis. Additionally, an LC-ESI-MS qualitative analysis was performed and an ultra performance liquid chromatography (UPLC) method was developed and validated for the determination of these compounds. The UPLC method was applied to the quantitative analysis of plant samples. Pyrones and caffeoylquinic acids resulted to be the main compounds in the extract; in particular desmethylangonine β-d-O-glucopyranosyl-(1→6)-O-β-d-glucopyranoside was the most abundant compound. 相似文献
2.
The reversed-phased HPLC analysis of the methanol extract of the pericarp of C. taliera Roxb. (Talipalm), a rare species of Arecaceae family, afforded a new steroidal glycoside, β-sitosterol-3-O-α-l-rhamnopyranosyl-(1→4)-β-d-xylopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (1). The structure of the compound was elucidated unequivocally by UV, IR, HR-ESI-MS, 1H and 13C NMR spectroscopic studies. 相似文献
3.
Qingchao Liu Tiantian Guo Dong Li Wenhong Li 《Research on Chemical Intermediates》2016,42(3):1611-1626
Two natural steroidal glycosides, diosgenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (1) and laxogenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2) with important cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines have been efficiently synthesized via straightforward sequential glycosylation reaction with the combined use of N-phenyltrifluoroacetimidates and trichloroacetimidates donors at room temperature. All structures of the synthesized new compounds were identified by 1H NMR, 13C NMR and HRMS spectra. 相似文献
4.
Lunli Xiang Lu Zhang Xuanqin Chen Xueshan Xia Rongtao Li 《Natural product research》2019,33(9):1349-1356
Investigation of the n-BuOH extract of the aerial parts of Elsholtzia bodinieri led to the isolation of two new ursane-type triterpenoid saponins, bodiniosides O (1) and P (2), along with five known saponins, rotungenoside (3), 3,28-O-bis-β-d-glucopyranosides of 19α-hydroxyarjunolic acid (4), oblonganosides I (5), rotungenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (6), and bodinioside M (7) isolated from the species. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-β-d-xylopyranosyl-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-β-d-xylopyranosyl-(1→6)-[β-d-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside and 3-O-β-d-xylopyranosyl-23-hydroxy-urs-12(13)-en-28-oic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside. Compounds 1 and 2 exhibited potent anti-HCV activities in vitro with a selective index of 30.63 and 9.08, respectively. 相似文献
5.
Abstract The proton and carbon nuclear magnetic resonance spectroscopic data for methyl 4-O-α-d-glucopyranosyl-[6-O-a-u-glucopyranosyl]-β-d-glucopyranoside (1), a model for the branch-point trisacch-aride of amylopectin, have been analysed using 2-D-heteronuclear correlated spectroscopy. Similar data are presented for the related disaccharide structures methyl β-d-maltopyranoside and β-d-isomal topyranoside. 相似文献
6.
7.
Abstract A carboxylate-containing pentasaccharide, methyl O-(β-d-galactopyranosyl)-(1→4)-O-(β-d-glucopyranosyl)-(1→6)-O-{3-O-[(S)-1-carboxyethyl]-β-d-galactopyranosyl-(1→4)-O}-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-β-d-galactopyranoside (27) was synthesized by block condensation of suitably protected donors and acceptors. Phenyl 3-O-benzyl-4,6-di-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside (17) was condensed with methyl 2,4,6-tri-O-benzyl-β-d-galactopyranoside (4) to afford a disaccharide, methyl O-(3-O-benzyl-4,6-di-O-chloroacetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (18). Removal of chloroacetyl groups gave 4,6-diol, methyl 0-(3-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (19), in which the primary hydroxy group (6-OH) was then selectively chloroacetylated to give methyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (20). This acceptor was then coupled with 2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-α-d-galactopyranosyl trichloroacetimidate (14) to afford a trisaccharide, methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-l-(methoxycarbonyl)ethyl]-β-d-galactopyranosyl}-(1→4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (21). Removal of the 6-O-chloroacetyl group in 21 gave 22, which was coupled with 4-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-2,3,6-tri-O-acetyl-α-d-glucopyranosyl trichloroacetimidate (23) to yield protected pentasaccharide 24. Standard procedures were used to remove acetyl groups and the phthalimido group, followed by N-acetylation, and debenzylation to yield pentasaccharide 27 and a hydrazide by-product (28) in a 5:1 ratio, respectively. Compound 27 contains a complete repeating unit of the capsular polysaccharide of type III group B Streptococcus in which terminal sialic acid is replaced by an (S)-1-carboxyethyl group. 相似文献
8.
Dai-Lin Liu Xue Zhang Yanmin Zhao Nai-Li Wang Xin-Sheng Yao 《Natural product research》2016,30(23):2694-2703
Three new triterpenoid saponins, ardisicrenoside O (1), ardisicrenoside P (2) and ardisicrenoside Q (3) together with three known compounds, 3β,16α-dihydroxy-30-methoxy-28, 30-epoxy-olean-12-en, cyclamiretin A 3-O-β-d-glucopyranosyl-(1→2) -α-l-arabinopyranoside and cyclamiretin A 3-O-β-d-glucopyranosyl-(1→4) -α-l-arabinopyranoside were isolated from the roots of Ardisia crenata Sims. Their structures were determined by one- and two-dimensional NMR techniques, including HSQC, HMBC and TOCSY experiments, as well as acid hydrolysis and GC analysis. All isolates were evaluated for the cytotoxic activities on two human cancer cell lines and compounds 3, 5 and 6 showed significant cytotoxicity. 相似文献
9.
Olivier Placide Noté Line Made Simo Joséphine Ngo Mbing Dominique Guillaume Christian Dominique Muller Dieudonné Emmanuel Pegnyemb 《Natural product research》2019,33(2):180-188
As a continuation of our interest in the study of triterpenoid saponins from Albizia zygia, phytochemical investigation of its stem barks led to the isolation of two new oleanane-type saponins, named zygiaosides C–D (1–2). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as, 3-O-[ β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (1) and 3- O-[β-d-glucopyranosyl-(1→2) -[ β-d-fucopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (2). 相似文献
10.
Yhiya M. Amen Amani M. Marzouk Mona G. Zaghloul Mohamed S. Afifi 《Natural product research》2015,29(6):511-517
A new acylated kaempferol glycoside, kaempferol 3-O-α-l-rhamnopyranosyl-(1 → 6)-O-[β-d-glucopyranosyl-(1 → 2)-4-O-acetyl-α-l-rhamnopyranosyl-(1 → 2)]-β-d-galactopyranoside, has been isolated from the leaves of Tipuana tipu (Benth.) Lillo growing in Egypt, along with three known flavonol glycosides, kaempferol 3-O-rutinoside, quercetin 3-O-rutinoside (rutin) and kaempferol 3-O-[α-l-rhamnopyranosyl-(1 → 6)]-[α-l-rhamnopyranosyl-(1 → 2]-β-d-glucopyranoside. Structure elucidation was achieved through different spectroscopic methods. Structure relationship with anti-inflammatory activity using carrageenin-induced rat paw oedema model is discussed. 相似文献
11.
Hai-Yang Wang Ke Liu Ru-Xia Wang San-Hai Qin Feng-Ling Wang 《Natural product research》2015,29(7):644-649
Two new triterpenoids and three 27-nor-triterpenoids were isolated from the stems (with bark) of Nauclea officinalis. Their structures were identified to be 2β,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid (1), 2β,3β,19α,23-tetrahydroxy-urs-12-en-28-O-[β-d-glucopyranosyl (1-2)-β-d-glucopyranosyl] ester (2), pyrocincholic acid 3β-O-α-l-rhamnopyranoside (3), pyrocincholic acid 3β-O-α-l-rhamnopyranosy1-28-O-β-d-glucopyranosyl ester (4), pyrocincholic acid 3β-O-α-l-rhamnopyranosy1-28-O-β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl ester (5) by spectroscopic methods including 1D, 2D NMR and HR-MS analyses. The cytotoxic activity of 1–5 against lung cancer A-549 cells was also investigated. 相似文献
12.
《Journal of carbohydrate chemistry》2013,32(5):385-409
A variety of sialyl-α-(2→3)-neolactotetraose (IV3NeuAcnLcOse4 or IV3NeuGcnLcOse4) derivatives (23, 31–37, 58–60) modified at C-2 of the GlcNAc residue have been synthesized. The phthalimido group at C-2 of GlcNAc in 2-(trimethylsilyl)ethyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside (5) was systematically converted to a series of acylamino groups, to give the per-O-benzylated trisaccharide acceptors (6–11). On the other hand, modification of the hydroxyl group at C-2 of the terminal Glc residue in 2-(trimethylsilyl)ethyl (4,6-O-benzylidene-β-d-glucopyranosyl)-(1→3)-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside (42) gave three different kinds of trisaccharide acceptors containing D-glucose (49), N-acetyl-d-mannosamine (50), and D-mannose (51) instead of the GlcNAc residue. Totally ten trisaccharide acceptors (5–11 and 49–51) were each coupled with sialyl-α-(2→3)-galactose donor 12 to afford the corresponding pentasaccharides (14–21 and 52–54) in good yields, respectively, which were then transformed into the target compounds. Acceptor specificity of the synthetic sialyl-α-(2→3)-neolactotetraose probes for the human α-(1→3)-fucosyltransferases, Fuc-TVII and Fuc-TVI, was examined. 相似文献
13.
Two new quercetin glycoside derivatives named quercetin-3-O-[2-O-trans-caffeoyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside] (1) and quercetin-3-O-[2-O-trans-caffeoyl-β-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside] (2) along with three known flavonoids, 5-hydroxy-6,7,3′,4′,5′-pentamethoxyflavone (3), 5,7-dihydroxy-8-methoxyflavone (4) and kaempferol 3-O-β-d-glucopyranoside (5), were isolated from the fruits of Gardenia jasminoides var. radicans. The structures of the new compounds were determined by means of extensive spectroscopic analysis (1D, 2D NMR and HR-ESI-MS), glycoside hydrolysis and sugar HPLC analysis after derivatisation. This is the first report on the isolation of a pair of compounds with α or β-l-rhamnopyranosyl configuration from plant and the first detail assignment of their NMR data. 相似文献
14.
From the ethanol extract of Selaginella moellendorffii Hieron., a new flavone O-glycoside and three known flavone C-glycosides have been isolated and identified as 5-carboxymethyl-4′-hydroxyflavone-7-O-β-D-glucopyranoside 1, 6,8-di-C-β-D-glueopyranosylapigenin 2, 6-C-[3-D-glucopyranosyl-8-C-β-D-xylopyranosyl apigenin 3, 6-C-B-D-xylopyranosyl-8-C-β-glucopyranosylapigenin 4, respectively. Their structures were elucidated by spectroscopic methods. 相似文献
15.
Kenji Hotta Tomoko Kawase Hideharu Ishida Makoto Kiso Akira Hasegawa 《Journal of carbohydrate chemistry》2013,32(7):961-975
Abstract A first total synthesis of a β-series ganglioside GQ1β (IV3Neu5Acα2, III6Neu5Acα2-Gg4Cer) is described. Regio- and stereoselective dimeric sialylation of the hydroxyl group at C-6 of the GalNAc residue in 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3-O-levulinyl-β-d-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-O-2,3,6-tri-O-benzyl-β-d-glucopyranoside (3) with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylono-1′,9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-d-glycero-d-galacto-2-nonulopyranosid]onate (4) using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as a promoter gave the desired pentasaccharide 5 containing α-glycosidically-linked dimeric sialic acids. This was transformed into the acceptor 6 by removal of the levulinyl group. Condensation of methyl O-[methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylono-1′,9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-d-glycero-d-galacto-2-nonulopyranosylonate]-(2→3)-2,4,6-tri-O-benzoyl-1-thio-β-d-galactopyranoside (7) with 6, using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, gave the desired octasaccharide derivative 8 in high yield. Compound 8 was converted into α-trichloroacetimidate 11, via reductive removal of the benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (12), gave the β-glycoside 13. Finally, 13 was transformed, via selective reduction of the azido group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside 15 in good yield. 相似文献
16.
Akihiko Kameyama Hideharu Ishida Makoto Kiso Akira Hasegawa 《Journal of carbohydrate chemistry》2013,32(5):641-654
Abstract The first total synthesis of tumor-associated glycolipid antigen, sialyl Lea, is described. Methylsulfenyl bromide-silver triflate-promoted coupling of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-β-d-glucopyranosyl)-(1→3)-O-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside (2) with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylonate)-(2→3)-2,4,6-tri-O-benzoyl-1-thio-β-d-galactopyranoside (3) afforded the pentasaccharide 4a and 5a in good yields. Glycosylation of 4a with methyl 2,3,4-tri-O-benzyl-1-thio-β-l-fucopyranoside (6) by use of N-iodosuccinimide (NIS) — trifluoromethanesulfonic acid (TfOH) as a promoter, gave the desired hexasaccharide 7. Compound 7 was converted into the α-trichloroacetimidate 10, via reductive removal of benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1, 3-diol (11), gave the β-glycoside 12. Finally, 12 was transformed, via selective reduction of the azide group, coupling with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title ganglioside 15 in good yield. 相似文献
17.
Abstract The primary structure of an elicitor-active oligosaccharide, LN-3, prepared from partially hydrolyzed algal laminaran was determined by means of the analyses of glycosyl-linkage, fragments by acetolysis, and glycosyl-sequence. The elicitor-active oligosaccharide, LN-3, is a pyridylaminated hepta-β-d-glucoside which was shown to have the following linear structure: β-d-Glcp(1→6)-β-d-Glcp(1→3)-β-d-Glcp(1→3)-β-d-Glcp(1→3)-β-d-Glcp(1→6)-β-d-Glcp(1→3)-Glc-PA. 相似文献
18.
Two new phenolic glycosides,2,3-dihydroxybenzoic acid methyl ester 3-O-β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside(1) and 2,5-dihydroxylbenzofuran 5-O-β-D-xylopyranosyl-(1-6)-O-β-D-glucopyranoside(2),were isolated as the minor chemical constituents from the roots of Gentiana rigescens,along with 15 known compounds.Their structures were elucidated by detailed spectroscopic analysis,including 1D,2D NMR and chemical method.All of these compounds were isolated for the first time from the title plant.Moreove... 相似文献
19.
Biao Zeng Guang-Da Liu Bao-Bao Zhang Shan-shan Wang Rui Ma Bei-Shan Zhong 《Natural product research》2016,30(9):1001-1008
A new triterpene saponin, 3β,16β,23α,28β,30β-pentahydroxyl-olean-11,13(18)-dien-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside, was named Clinoposaponin D (1), together with six known triterpene saponins, buddlejasaponin IVb (2), buddlejasaponin IVa (3), buddlejasaponin IV (4), clinopodisides D (5), 11α,16β,23,28-Tetrahydroxyolean-12-en-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside (6) and prosaikogenin A (7), and two known triterpenes, saikogenin A (8) and saikogenin F (9) were isolated from Clinopodium chinense (Benth.) O. Kuntze. Their structures were elucidated on the basis of 1D, 2D NMR and MS analysis. Meanwhile, the effects of all compounds on rabbit platelet aggregation and thrombin time (TT) were investigated in vitro. Compounds 4 and 7 had significant promoting effects on platelet aggregation with EC50 value at 53.4 and 12.2 μM, respectively. In addition, the highest concentration (200 μM) of compounds 2 and 9 shortened TT by 20.6 and 25.1%, respectively. 相似文献
20.
Koushik Mazumder Swarbhanu Sarkar Asish Kumar Sen 《Journal of carbohydrate chemistry》2013,32(9):673-685
The terminal disaccharide of the O-antigenic polysaccharide of Vibrio cholerae O37, 4-O-methyl-α-D-QuiNAc-(1→4)-α-d-QuiNAc, was synthesized as methyl glycoside involving glycosylation between glycosyl donor ethyl 2-azido-3-O-benzyl-2,6-dideoxy-4-O-methyl-6-iodo-1-thio-α-d-glucopyranoside and glycosyl acceptor methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-d-glucopyranoside. Dehalogenation, global deprotection, and reduction of the azide to amine were effected in one step by catalytic hydrogenation. It was followed by selective N-acetylation to give the desired deprotected disaccharide. 相似文献