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At least 1,207 records · Page 67Linked to original sources
PubMed1993

Karsoside and scropolioside D, two new iridoid glycosides from Scrophularia ilwensis.

Two new iridoid glycosides, karsoside [1] and scropolioside D [2], were isolated from the aerial parts of Scrophularia ilwensis. Their structures were elucidated on the basis of chemical and spectral data as 6'-O-(beta-D-xylopyranosyl)-methylcatalpol and 6-O-[(2",4"-di-O-acetyl-3"-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]- catalpol, respectively. Additionally, four known iridoids (aucubin, harpagide, 8-O-acetylharpagide, and ajugol), a phenylpropanoid glycoside (angoroside C), and two flavonoids (quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside) were isolated and identified.

Acetylation↗
PubMed1993

A novel amino acid glycoside and three amino acids from Allium sativum.

A novel amino acid glycoside (-)-N-(1'-deoxy-1'-beta-D-fructopyranosyl)-S-allyl-L-cysteine sulfoxide [1], was isolated from a hydrophilic extract of the leaves of Allium sativum (Alliaceae), together with three known compounds: (+)-S-allyl-L-cysteine sulfoxide [2],(+)-S-methyl-L-cysteine sulfoxide [3], and (+)-S-(trans-1-propenyl)-L-cysteine sulfoxide [4]. The latter two substances were isolated for the first time from garlic. The structure elucidation of 1 was performed by extensive chemical, spectroscopic (ir, fabms, 1D and 2D(1)H- and (13)C-nmr measurements) and chromatographic experiments. For the first time, detailed nmr data and the unambiguous assignment of all (13)C-nmr data for compounds 2-4 were reported. Compound 1, the amino acid glycoside, revealed a significant inhibition of in vitro platelet aggregation induced by ADP and epinephrine, whereas none of the amino acids tested displayed any activity.

Amino Acids↗
PubMed1993

Starfish saponins, Part 50. Steroidal glycosides from the Okinawan starfish Nardoa tuberculata.

This paper describes a complete analysis of the glycoside and polyhydroxysteroid constituents of the starfish Nardoa tuberculata, collected at Zampa, Okinawa, Japan. Besides a group of known non-sulfated steroidal diglycosides, halitylosides A [5], B [6], D [7], E [8], and F [9], and two known polyhydroxysteroids 10 and 11, N. tuberculata also contains four new sulfated steroidal glycosides 1-4 closely related to the previous halitylosides. The antifungal activities and the effects on the development of fertilized sea urchin eggs of some steroid components from this starfish were examined.

Animals↗
PubMed1996

Pyridine monoterpene alkaloid formation from iridoid glycosides. A novel PMTA dimer from geniposide.

New pyridine monoterpene alkaloids (PMTAs) have been synthesized from the iridoid glycosides 8-epi-loganin, cornin, and antirrinoside by treatment with beta-glucosidase and aqueous NH4-OAc. The PMTA from antirrinoside contained an 8-alpha-OAc group from the opened 7,8-epoxide moiety. Treatment of genipin, the aglycone of geniposide, with HCl(g) and NH3(g) yielded the PMTA racemigerine, a known plant isolate, in which the C=C-CH2OH side chain was converted to C=C-CH3. Reaction of geniposide with beta-glucosidase and aqueous NH4OAc led to oligomeric alkaloids, but at high dilution a dimer was obtained whose structure was formally that of a Diels-Alder adduct between racemigerine and a dihydropyridine. These biomimetic semisyntheses were analyzed in terms of reaction mechanisms and the relative paucity of known plant PMTAs in comparison with the multitudinous occurrence of their presumed iridoid glycoside precursors.

Glycosides↗
PubMed1997

Structural investigation of resin glycosides from Ipomoea lonchophylla.

A fraction from Ipomoea lonchophylla, which was toxic to mice, contained an inseparable mixture of resin glycosides with differing numbers of C5 ester groups on the hexasaccharide chain. After alkaline hydrolysis of the esters, the structure of the major component (1) was elucidated using high-field NMR spectroscopy, mass spectrometry, chemical studies, and comparison with known resin glycosides. Compound 1 was identified as 3,11-dihydroxytetradecanoic acid 11-O-beta-quinovopyranosyl-(1-->2)-beta-glucopyranosyl-(1-->3)- [alpha-rhamnopyranosyl- (1-->4)]-quinovopyranosyl-(1-->2)-beta-glucopyranosyl-(1-->2)-beta -fucopyranoside.

Animals↗
PubMed1998

Croton ruizianus: platelet proaggregating activity of two new pregnane glycosides.

The MeOH extract of the aerial parts of Croton ruizianus afforded two new pregnane glycosides 1 and 2, together with the morphinandienone alkaloids flavinantine (3) and O-methylflavinantine (4). Their structures were elucidated by NMR experiments including 1H-1H (1D TOCSY and 2D DQF-COSY) and 1H-13C (HSQC, HMBC) spectroscopy. The proaggregating activity of the MeOH extract and the isolates were evaluated. Although the MeOH extract and pregnane glycosides (at different doses) were found to promote platelet aggregation, flavinantine (3) and O-methylflavinantine (4) showed only slight activity. The ability of the MeOH extract and the four compounds to act synergistically with thrombin was also evaluated. All the tested compounds were successful in augmenting the aggregating effect of thrombin, although to different degrees.

Blood Platelets↗
PubMed1998

Gmelinosides A-L, twelve acylated iridoid glycosides from Gmelina arborea.

Besides the known iridoids 6-O-alpha-L-rhamnopyranosylcatalpol (1), 6-O-(3"-O-trans-feruloyl)-alpha-L-rhamnopyranosylcatalpol (14), 6-O-(2"-O-acetyl-3", 4"-O-di-trans-cinnamoyl)-alpha-L-rhamnopyranosylcatalpol (15) and the known phenylpropanoid glycosides verbascoside (acteoside) and martynoside, 12 new acylated iridoid glycosides named gmelinosides A-L (2-13) have been isolated from the leaves of Gmelina arborea. These compounds were structurally characterized using a variety of spectral methods.

Carbohydrate Sequence↗
PubMed1998

Phenylethanoid glycosides from Digitalis purpurea and Penstemon linarioides with PKCalpha-inhibitory activity.

In a continuation of our search for potential tumor inhibitors from plants, it was found that the CH2Cl2-MeOH (1:1) extracts from Digitalis purpurea and Penstemon linarioides both showed PKCalpha-inhibitory bioactivity. Bioassay-directed fractionation of the extract from D. purpurea yielded the new, weakly active phenylethanoid glycoside 2-(3-hydroxy-4-methoxy-phenyl)-ethyl-O-(alpha-L-rhamnosyl)-(1-->3) -O- (alpha-L-rhamnosyl)-(1-->6)-4-O-E-feruloyl-beta-D-glucopy ran oside (1) together with the four known compounds calceolarioside A (2), calceolarioside B (3), forsythiaside (4), and plantainoside D (5). The extract from P. linarioides yielded the three known glycosides leucosceptoside A (6), acteoside (7), and poliumoside (8), together with the iridoid plantarenaloside (9). All of the isolated compounds, except compound 9, showed inhibitory activity against PKCalpha with IC50 values (in microM) of 125 (1), 0.6 (2), 4.6 (3), 1.9 (4), 14.8 (5), 19.0 (6), 9.3 (7), and 24.4 (8).

Caffeic Acids↗
PubMed1998

Cycloartane triterpene glycosides from the roots of Astragalus brachypterus and Astragalus microcephalus.

Three new cycloartane-type triterpene glycosides, brachyosides A (1), B (3), and C (2), from the roots of Astragalus brachypterus and one new glycoside, cyclocephaloside II (4), from the roots of Astragalusmicrocephalus have been isolated together with five known saponins, astragalosides I, II, and IV, cyclocanthoside E, and cycloastragenol. The structures of the new compounds were established as 3-O-[beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl-6-O-beta-D-gluc opyranosyl-3beta,6alpha,16beta,24(S),25-pentahydrox ycycloartane (1), 3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-24-O-beta-D-glucop yranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxyc ycloartane (2), 20(R),24(S)-epoxy-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta , 25-tetrahydroxycycloartane (3), and 20(R), 24(S)-epoxy-3-O-(4'-O-acetyl)-beta-D-xylopyranosyl-6-O-beta-D-glucopy ranosyl-3beta,6alpha,16beta,25-tetrahydroxycycloart ane (4). For the structure elucidations, 1D- and 2D-NMR experiments and FABMS were used.

Carbohydrate Sequence↗
PubMed1999

Verbaspinoside, a new iridoid glycoside from Verbascum spinosum.

A new iridoid glycoside, verbaspinoside (1), was isolated from the aerial parts of Verbascum spinosum. Its structure was elucidated on the basis of chemical and spectral data as 6-O-[(2' '-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-catalpol. Additionally, three known iridoids (aucubin, catalpol, and ajugol) and three phenylpropanoid glycosides [acteoside, angoroside A (2), and angoroside C (3)] were isolated and identified.

Carbohydrate Conformation↗
PubMed1999

Novel isoflavone, cinnamic acid, and triterpenoid glycosides in soybean molasses.

Seven known isoflavones, genistein (4), daidzein (5), glycitein (6), formononetin (7), genistin (8), daidzin (9), and glycitein 7-O-beta-D-(6' '-O-acetylglucopyranoside) (10), ferulic acid, and two known saponin glycosides, soysaponin I (14) and soysaponin A2 (15), were isolated from soybean molasses. Several new compounds were also isolated and identified, including three isoflavones (1-3), two cinnamic acid ester glycosides (11) and (12), and a new saponin hexaglycoside (13). The structures of the new compounds were established on the basis of spectral data interpretation.

Carbohydrate Sequence↗
PubMed1999

Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium.

(3R)-O-beta-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-beta-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[beta-D-glucopyranosyl-(1-->6)-glucopyranosyl]oxy-2'-hydroxy-3', 6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-beta-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-beta-D-galactopyranoside (5), quercetin-3-O-beta-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-beta-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2''-O-galloyl)-beta-D-glucopyranoside (8), and quercetin-3-O-beta-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.

Carbohydrate Sequence↗
PubMed2000

Higher order and substituent chemical shift effects in the proton NMR of glycosides.

The full analysis of (1)H NMR spin systems and the charting of substituent chemical shifts offer great potential in the structure elucidation of glycosides. Due to the chiral nature of sugar residues, asymmetric induction causes diastereotopic shifts of aglycon resonance, while on the other hand aromatic substituent-induced shifts affect the sugar portion of the molecule. Therefore, it is possible to deduce critical structural information, such as the site of sugar linkage in bisdesmosides and oligoglycosides, through the analysis of exact chemical shifts, J patterns, and signal multiplicity. The potential of the method is demonstrated for three kaempferol bisdesmosides (1-3) by establishing the shift characteristics for 3-O-, 7-O-, and 6' '-O-glycosidation. Spectral simulation and soft-pulse 1D NMR turn out to be indispensable tools in the course of refined signal and structure assignment.

Arabidopsis↗
PubMed2000

Pregnane glycosides from Caralluma russeliana.

The aerial parts of Caralluma russeliana yielded four new pregnane glycosides, russeliosides A-D (1-4), in addition to a known flavone glycoside, luteolin 4'-O-beta-D-neohesperidoside. The structures of compounds 1-4 were elucidated using a combination of spectroscopic methods.

Glycosides↗
PubMed2000

Radical-mediated synthesis of alpha-C-glycosides based on N-acyl galactosamine.

[structure] C-Glycosides of N-acyl 2-amino-2-deoxygalactose (acyl = MeCO, CF(3)CO, t-BuOCO) are available in a stereoselective manner by trapping of an anomeric radical with an activated alkene. Using anomeric selenides, radical generation and trapping is carried out under conditions that avoid competitive reduction, and this chemistry has been applied to the synthesis of the novel C-glycoside analogue of O-benzyl alpha-D-GalNAc.

Alkenes↗
PubMed2001

Versatile 8-oxabicyclo[3.2.1]oct-6-en-3-one: stereoselective methodology for generating C-glycosides, delta-valerolactones, and polyacetate segments.

[figure: see text] A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta-valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported. Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

Acetates↗
PubMed2001

Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates.

[reaction: see text] Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries-like rearrangement. The rearrangement was stereo- and regiospecific, yielding only one C-glycoside product. C-Alkyl glycoside carbohydrate mimetics were generated by using silicon-derived C-nucleophiles and glycosyl phosphates.

Drug Design↗