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PubMed1988

Isolation and structural elucidation of three new pyridoxine-glycosides in rice bran.

Three new pyridoxine-glycosides were isolated from rice bran (10 kg) as colorless powder by various chromatographic techniques: compound A, 53 mg; compound B, 7.8 mg; compound C, 5.8 mg. Compound A was shown to consist of pyridoxine and glucose in a 1:2 molar ratio by beta-glucosidase hydrolysis, and by 1H-NMR and secondary ion mass spectrometry (SI-MS) data. On partial acid hydrolysis of the compound, cellobiose was liberated. Compound A showed the positive Gibbs color reaction, but the reaction was negative in the presence of boric acid. Thus, compound A was identified as 5'-O-(beta-cellobiosyl)pyridoxine. The 13C-NMR spectral data were compatible with this structure. Compounds B and C were proven to be triglucosides of pyridoxine by enzymic hydrolysis and SI-MS data. From the results of the Gibbs color reaction and partial hydrolyses which yielded compound A, compound B was concluded to be 4'-O-(beta-D-glucosyl)-5'-O-(beta-cellobiosyl)pyridoxine, and compound C to be 5'-O-(beta-glucotriosyl)pyridoxine in which a glucose molecule was bound to the cellobiosyl moiety of compound A through beta-glycosidic linkage.

Chromatography↗
PubMed1984

Specific cleavage of the glycosidic bond between the carbohydrate and ceramide portions in glycosphingolipids using trifluoroacetolysis.

A number of glycosphingolipids have been subjected to trifluoroacetolysis. Heating the glycosphingolipid at 100 degrees C for 48 h in mixtures of trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) varying from 1:1 to 1:100 (v/v) resulted in complete cleavage of the glycosidic bond between the carbohydrate and the unsaturated base of the ceramide. The fatty acid(s) linked to the amino group of sphingosine were also released by transamidation. The carbohydrate portion was stable under these conditions due to stabilization of the glycosidic bonds by the electronegative O-trifluoroacetyl groups. The 2-acetamido-2-deoxy-hexose units in the glycosphingolipids were converted into their N-trifluoroacetyl analogues. The N-trifluoroacetyl functions could be removed and the 2-acetamido-2-deoxy-hexoses could be reconstituted by N-acetylation.

Carbohydrates↗
PubMed1989

Cyclopentenoid cyanohydrin glycosides with unusual sugar residues.

The cyclopentenoid cyanohydrin glycosides passicapsin and passibiflorin have been identified as (1S, 4R)-1-(beta-D-glucopyranosyloxy)-4-(2,6-dideoxy-beta-D-xylo-hex o pyranosyloxy)-2-cyclopentene-1-carbonitrile and (1S, 4R)-1-(beta-D-glucopyranosyloxy)-4-(6-deoxy-beta-D-gulopyranosy loxy)-2- cyclopentene-1-carbonitrile, respectively, using one- and two-dimensional NMR spectroscopy, selective acid-catalysed cleavage of the glycosidic linkages of the deoxy sugars, and optical rotation data.

Carbohydrates↗
PubMed1996

Synthesis of kojitriose using silicon-tethered glycosidation.

Reaction of 3,4,6-tri-O-acetyl-beta-D-glucopyranosyl chloride (1) with potassium phenylselenate gave phenyl 3,4,6-tri-O-acetyl-1-seleno-alpha, beta-D-glucopyranoside (2) in 59% yield. Silylation of benzyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside (4) with ethyl 3,4,6-tri-O-benzyl-2-O-chlorodimethylsilyl-1-thio-beta -D-glucopyranoside gave benzyl 2-O-(3,4, 6-tri-O-benzyl-1-S-ethyl-1-thio-beta-D-glucopyranos-2-O-yldimet hylsilyl)-3,4,6,-tri-O-benzyl-beta-D-glucopyranoside (5) in 35% yield. Reaction of 5 with N-iodosuccinimide in nitromethane gave benzyl 2-O-(3,4, 6-tri-O-benzyl-alpha-D-glucopyranosyl)-3,4, 6-tri-O-benzyl-beta-D-glucopyranoside (6) in 45% yield. Chlorodimethylsilylation of phenyl 3,4, 6-tri-O-acetyl-1-seleno-alpha-D-glucopyranoside (2 alpha) and reaction with 6 gave benzyl 2-O-[2-O-(3,4,6 -tri-O-acetyl-1-Se-phenyl-1-seleno-alpha-D-glucopyranos-2-O-yld imethylsilyl) -3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3,4,6-tri-O-benzyl-beta-D- glucopyranoside (7) in 82% yield. Intramolecular glycosidation of 7 using N-iodosuccinimide in nitromethane gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl)-3, 4,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3, 4,6-tri-O-benzyl-beta-D-glucopyranoside (8) in 45% yield. Deprotection of 8 gave kojitriose (9) in quantitative yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzyl-alpha, beta-D-fructofuranose (10) with dimethyldichlorosilane and pyridine followed by reaction with ethyl 3,4, 6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (3) gave ethyl 2-O-(1,3,4,6-tetra-O-benzyl-alpha, beta-D-fructofuranosyloxydimethylsilyl)-3,4, 6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (11) in 85% yield. Chlorodimethylsilylation of 1,3,4, 6-tetra-O-benzoyl-alpha-D-fructofuranose (12) with dimethyldicholorosilane and triethylamine followed by reaction with phenyl 3,4, 6-tri-O-acetyl-1-thio-alpha-D-glucopyranoside (13) gave phenyl 2-O-(1,3,4, 6-tetra-O-benzoyl-alpha-D-fructofuranosyloxydimethylsilyl)-3, 4,6-tri-O-acetyl-1-thio-alpha-D-glucopyranoside (14) in 62% yield. Both 11 and 14 failed to undergo intramolecular glycosidation.

Glycosides↗
PubMed1989

Structural elucidation of aculeximycin. I. Further purification and glycosidic bond cleavage of aculeximycin.

A new insecticidal antibiotic, aculeximycin (ACM), was produced by an actinomycete identified as Streptosporangium albidum. ACM has been successfully isolated from culture filtrate by a combination of Diaion HP-20, Amberlite CG-50, reversed phase silica gel and Sephadex LH-20 chromatographies. It was found that ACM is a basic glycosidic antibiotic with a molecular weight of 1,672 including five monosaccharide units, three double bonds and a hemiketal ring by preliminary spectral analyses. Treatment of ACM with 1,8-diazabicyclo[5,4,0]undecene-7 caused a glycosidic bond cleavage to give aculexitriose, pseudoaglycones I and II.

Actinomycetales↗
PubMed1999

[Synthesis of Neu5Ac(alpha2-->6)[Gal(alpha1-->3)]GalNAcalpha and Neu5Ac(alpha2-->6)[Gal(beta1-->3)]GalNAcalpha trisaccharides as protected trifluoroacetamidopropyl glycosides].

Protected sialo-containing trisaccharides, fragments of oligosaccharide chains of mucin glycoproteins, were synthesized. Regioselective sialylation of the primary hydroxyl group of (3-fluoroacetamidopropyl)-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-ben zyl)-alpha -D-galactopyranosyl)-alpha-D-galactopyranoside with methyl ester of peracetyl-beta-ethylthioglycoside of N-acetylneuraminic acid in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid (or its trimethylsilyl ester) yielded 39 and 25% of alpha- and beta-sialyl-(2-->6)biosides, respectively. Catalytic hydrogenolysis of the azide and benzyl groups of the alpha-anomer followed by N- and O-acetylation gave target trifluoroacetamidopropyl glycoside, Neu5Ac(alpha 2-->6)[Gal(alpha 1-->3)]GalNAc alpha-OSp, as a peracetate. An analogous coupling of the sialyl donor with (3-fluoroacetamidopropyl)-2-acetamido-2-deoxy-3-O- (2,3,4,6-tetra-O-acetyl)-beta-D-galactopyranosyl)-alpha-D-galactopyranos ide affords acetylated trifluoroacetamidopropyl glycoside Neu5Ac(alpha 2-->6)[Gal(beta 1-->3)]GalNAc alpha-OSp in a yield of 15% and the corresponding Neu5Ac(beta 2-->6)-anomer in a yield of 12%. After O-deacetylation and N-detrifluoroacetylation, these sialylbiosides can be used as ligands in preparing neoglycoconjugates.

Carbohydrate Sequence↗
PubMed1999

Role of Ca2+ on uterine force stimulated by a glycoside from the root of Dalbergia saxatilis.

Uterine muscle contraction is dependent on external Ca2+ and Ca2+ release from cytoplasmic storage sites. In this study, the mechanism of Ca2+ mobilization in uterine muscle cells by glycoside, dalsaxini, isolated from the root of D. Saxatilis was investigated in the rat. Uterine muscle contractility stimulated by dalsaxin was concentration dependent (ED50 0.13 mg/ml) and was significantly attenuated (85%; P < 0.01) in Ca(2+)-free physiological solution and in solutions containing verapamil (0.06-0.48 mumol). The small transient contraction observed in Ca(2+)-free medium was further suppressed by caffeine (2 mmol) and completely abolished in solutions containing Lanthanum chloride [(La3+), 2 mmol]. Contractions stimulated by the glycoside were unaffected by amiloride (50-83 mumol) in Ca(2+)-free and Ca(2+)-containing media. Dalsaxin also altered the pattern of uterine contraction stimulated by high potassium depolarization from fast-phasic to a sustained but transient plateau. It is concluded that dalsaxin causes uterine muscle contraction by mobilizing external Ca2+ through predominantly a voltage-dependent Ca2+ channel.

Amiloride↗
PubMed2000

[Synthesis of disaccharide Neu5Gcalpha(2-6)GalNAcalpha as a spacer glycoside].

The first synthesis of the Neu5Gc analogue of SiaTn disaccharide, which can be detected in breast tumors by immunochemical methods, is reported. The regioselective sialylation of (3-trifluoroacetamidopropyl)-2-azido-2-deoxy-alpha-D-galactopyranoside with peracetate of the methyl ester of N-acetoxyacetylneuraminic acid beta-ethylthioglycoside in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid (or its trimethylsilyl ester) resulted in the derivatives of alpha- and beta-sialyl(2-->6)galactosaminide in 39 and 32% yields, respectively. The catalytic hydrogenolysis of the azido group and subsquent N- and O-acetylation of the alpha-anomer gave the trifluoroacetamidopropyl glycoside peracetate. Removal of the protective groups led to glycoside Neu5Gc alpha(2-->6)GalNAc alpha-O(CH2)3NH2. Using the Neu5Gc derivative with acetoxyacetyl groups at positions O9 and O4 as a donor increases the alpha-selectivity of sialylation to afford the alpha- and beta-anomers in 69 and 8% yields, respectively.

Biomarkers, Tumor↗
PubMed1975

Contribution of kidney basement membranes and collagen to the urinary excretion of hydroxylysyl glycosides.

Glucosyl-galactosyl-hydroxylysine and galactosyl-hydroxylysine are two substances present only in collagen and in basement membranes. The purpose of this study is to estimate to what extent the kidney contributes to urinary hydroxylysyl glycoside excretion. "In vitro" perfusion of isolated kidneys allows the measurement of hydroxylysyl glycosides independently of the important amount of interstitial collagen present in the whole body. It is shown that the kidney parenchyma contributes no more than 10 percent of the glycosylated hydroxylysine excreted in urine. GBM is not the only renal source of glucosyl-galactosyl-hydroxylysine in urine. Tubular basement membrane and intersitial collagen of kidney may contribute to the excretion by the isolated organ.

Animals↗
PubMed2002

Collagen markers deoxypyridinoline and hydroxylysine glycosides: pediatric reference data and use for growth prediction in growth hormone-deficient children.

BACKGROUND: In children and adolescents, markers of bone and collagen metabolism reflect the dynamics of skeletal growth and development. The aim of this study was to assess the relationship of the urinary collagen markers deoxypyridinoline (DPD) and hydroxylysine (Hyl) and its glycosides [galactosyl-Hyl (Gal-Hyl) and glucosyl-Gal-Hyl] with growth. METHODS: Urine samples from 240 apparently healthy children and adolescents (6-19 years; 124 girls) and from 51 prepubertal children with growth hormone (GH) deficiency (3-14 years; 14 girls) were analyzed. Urinary Hyl and its glycosides were quantified by HPLC, and DPD was assessed by chemiluminescence assay. Urinary concentrations of all markers were related to urinary creatinine. RESULTS: Multiple regression analysis revealed that only age and height velocity were independently associated with these markers in healthy children. In GH-deficient patients, the urinary excretion of both analytes after 4 weeks of GH therapy correlated significantly with the height increase during the first treatment year (r = 0.79 for Gal-Hyl; r = 0.70 for DPD; P <0.001 each). In a multivariate linear regression model using Gal-Hyl concentrations at 4 weeks, baseline concentrations of insulin-like growth factor 1 and height velocity after 3 months accounted for 80% of the variability in height gain during the first treatment year. A model using DPD concentrations at 4 weeks, in place of Gal-Hyl concentrations, as well as baseline concentrations of insulin-like growth factor 1 and height velocity after 3 months accounted for 83% of the variability. CONCLUSIONS: These urinary bone and collagen markers give some early indication of growth response, but the prediction of an individual marker is too imprecise to serve as a basis for clinical decisions. Markers of bone and collagen metabolism might be more useful as components of multivariate growth prediction models.

Adolescent↗
PubMed2002

Cardiovascular glycoside-like intoxication following ingestion of Thevetia nereifolia/peruviana seeds: a case report.

Some plants contain glycoside compounds which determine cardiovascular symptoms similar to those observed after acute toxic digoxin administration. The present case report involves a patient who showed important cardiovascular symptoms following the ingestion of Thevetia nereifolia/peruviana seeds. About 30 min after ingestion, a 65-year-old man presented with dizziness, giddiness, numbness and a burning sensation, diarrhea, sweating, vomiting and ECG changes. At the time of admission he presented with tremors; his body temperature was 37 degrees C, and blood analysis gave the following results: K 5.6 mEq/l, myoglobin 176 IU, troponin T 0.10 ng/ml, PO2 69 mmHg, PCO2 37.4 mmHg, pH 7.33, HCO3- 19.9 mEq/l, hemoglobin 14.8 g/dl, saturation 92.5%. Echocardiography showed a left ventricle with normal global and segmentary contractility. The following days, the patient showed a reduction, until total resolution, of the atrioventricular block and of the alterations of the ST segment. The ectopic beats also resolved; K value before discharge was 4.4 mEq/l. On the third day, the serum levels of digoxin were 0.15 ng/ml. This case report is important because it describes all the cardiovascular and non-cardiovascular signs of glycoside toxicity in an adult patient who accidentally swallowed only two seeds (non-fatal dose) of Thevetia.

Aged↗
PubMed1975

Interaction of heart glycosides and phenobarbital.

One week's administration of phenobarbital does not affect the disappearance of a single dose of digitalis glycosides from the serum of man. The increase of bile flow and of liver weight produced by phenobarbital in the rat is not further enhanced by glycosides. In case of acute digitalization, the enzyme inducing effect of barbiturates has probably no clinical significance.

Adolescent↗
PubMed2002

The effect of three bufadienolide cardiac glycosides on contraction of isolated rat jejunum.

Three cardiac glycosides were screened for pharmacological effects on isolated rat jejunum. The contraction of rat jejunum with epoxyscillirosidin, a non-cumulative bufadienolide, and cotyledoside and tyledoside D, both cumulative neurotoxic bufadienolides were compared with methacholine. The results indicate that all three bufadienolides cause contraction of jejunal smooth muscle. When combined with atropine (1 x 10(-6) M) the response of epoxyscillirosidin and tyledoside D decreased, indicating suppression of a cholinergic response caused by the cardiac glycosides.

Animals↗
PubMed2002

Polyphenols of Egyptian Rosaceae plants--two new flavonoid glycosides from Sanguisorba minor Scop.

Two new flavonol glycosides, 8-methoxyquercetin-3-O-beta-glucosyl-(1'"-2")-O-beta-glucoside and kaempferol-3-O-[2'"-galloyl-O-beta-glucosyl-(1'"-2")-O-beta-glucoside)], together with five known quercetin and kaempferol 3-O-mono-glycosides, were isolated and identified from the aerial parts of Sanguisorba minor Scop. (Rosaceae). All structures were determined by routine methods of analysis and confirmed mostly by negative ESI-MS, 1H- and 13C NMR.

Flavonoids↗
PubMed1976

Pharmacological studies of a new 4-aminosugar cardiac glycoside (ASI-222).

ASI-222,3beta-O-(4-amino-4,6-dideoxy-beta-d-galactopyranosyl) digitoxigenin, is a semi-synthetic cardiac glycoside patterned after a natural glycoside obtained from Cambodia. Effects of ASI-222 on contractile force in the isolated rabbit atria, cardiac contractile force, cardiac rate, ventricular excitability and functional refractory period in dogs, and acute toxicity in mice have been compared to those effects of ouabain. Both electrically driven and spontaneously beating atria demonstrated more rapid onset and greater maximum increases in contractile force with ASI-222 than with ouabain in equal bath concentrations. In the dog, ASI-222 increased cardiac contractile force more rapidly and at a lower cumulative dose than ouabain. Moreover, the maximum increase in contractile force obtained with ASI-222 was greater than that obtained with ouabain. The occurrence of ventricular ectopic beats was observed at a higher cumulative dose of ASI-222 than for ouabain. Also, ASI-222 produced a decrease in ventricular excitability and an increase in functional refractory period ot the ventricle. Ouabain, in the same molar dose, produced either no change or a slight increase in these parameters. Our data indicate that ASI-222 has a greater therapeutic index than ouabain. This difference may be partially explained by effects of ASI-222 on electrical properties of the heart.

Aminoglycosides↗
PubMed1992

[Selective long-range DEPT NMR technique and its application to structural study of glycoside].

This paper reports a new NMR technique: selective long-range DEPT. The result obtained showed that the technique can be used to assign NMR signal of 13C, 15N and 31P nuclei, and connect the spin systems separated by quaternary carbon or heteroatom. This paper deals mainly with applying the technique for determining the glycosidation position in aglycone moiety and sequence of sugar moiety in a natural glycoside.

Glycosides↗
PubMed1992

Antidiabetic effect of a glycoside of pelargonidin isolated from the bark of Ficus bengalensis Linn.

The antidiabetic effect of a dimethoxy derivative of perlargonidin 3-O-alpha-L rhamnoside (250 mg/kg, single dose study and 100 mg/kg/day long term study) isolated from the bark of Ficus bengalensis Linn. has been compared with that of glibenclamide (2 mg/kg and 0.5 mg/kg/day respectively) in moderately diabetic rats. The single dose glycoside treatment decreased fasting blood glucose by 19% and improved glucose tolerance by 29%. The corresponding effects of glibenclamide were 25% and 66% respectively over the control values. On one-month treatment the fasting blood glucose levels went down almost to half of the pretreatment levels in both the groups and their glucose tolerance improved by 41% in glibenclamide group and by 15% in glycoside treated group. Urine sugar decreased to traces in both the groups and they appeared healthy. In vitro studies showed that insulin secretion by beta-cells was more in presence of the pelargonidin derivative than in presence of a leucocyanidin derivative, reported to be a good anti-diabetic agent.

Animals↗
PubMed1992

[Phenyl glycosides from Curculigo orchioides].

One new phenyl glycoside and two new chlorophenyl glycosides were isolated from rhizomes of Curculigo orchioides (Chinese name: Xian Mao, Hypoxidaceae). Based on HRMS, FABMS, 1H-, 13C-NMR and other spectral data as well as chemical evidence, the structures of curculigoside B, curculigine B and C were elucidated to be 2-beta-D-glucopyranosyloxy-5-hydroxybenzyl-2'-methoxy-6'-hydroxybe nzoate (I),24-dichloro-3-methyl-5-methoxy-phenol-O-beta-D-apiofuranosyl (1-6)-beta-D-glucopyanoside (III) and 2,4,6-trichloro-3-methyl-5-methoxyphenol-O-beta-D-xylopyranosyl (1-6)-beta-D-glucopyranoside (IV), respectively.

Drugs, Chinese Herbal↗