Glucoside Research Articles

Análise dos teores de ácidos cianídrico e fítico em suplemento alimentar: multimistura

OBJETIVO: Este estudo objetivou quantificar o teor de ácido cianídrico em folhas de mandioca, que receberam tratamento prévio antes da secagem, e a concentração de ácido fítico na multimistura submetida à cocção úmida. MÉTODOS: Utilizou-se a multimistura produzida pela Pastoral da Criança da cidade de Pelotas (RS), constituída por: farelos de trigo (30%) e arroz (30%): farinhas de milho (15%) e trigo (10%); pós de casca de ovo (5%), de folha de mandioca (5%) e de sementes (5%, abóbora ou girassol). Foi realizada orientação ao fornecedor da folha de mandioca sobre a forma recomendada de preparo antes da secagem. RESULTADOS: O conteúdo de ácidos cianídrico e fitatos no suplemento alimentar foram respectivamente de 85mg.kg-1 e 35.90mg.100-1. CONCLUSÃO: Verificou-se que a mudança na forma de secagem das folhas de mandioca foi eficiente para a redução de glicosídeos cianogênicos, e que o processo de torrefação dos ingredientes foi suficiente para produzir a redução de ácido fítico da multimistura aos níveis preconizados pela legislação, não sendo observadas diferenças estatisticamente significantes quando comparadas as amostras que também foram tratadas com calor úmido.

Novel Neolignan from Penthorum chinense

Abstract A new neolignan (7′E)‐2′,4,8‐trihydroxy‐3‐methoxy‐2,4′‐epoxy‐8,5′‐neolign‐7′‐en‐7‐one (1) was isolated from the whole plants of Penthorum chinense Pursh, along with lupeol (2), betulinic acid (3), glyceryl monopalmitate (4), β‐sitosterol (5), palmitic acid (6), ursolic acid (7), 2β,3β,23‐trihydroxy‐urs‐12‐ene‐28‐oic acid (8), glyceryl monolaurate (9), scopoletin (10), (–)syringaresinol (11), 9,9′‐O‐diferuloyl‐(–)‐secoisolariciresionl (12), pinocembrin (13), apigenin (14), kaempferol (15), luteolin (16), β‐daucosterol (17), quercetin (18), 1‐O‐(β‐D‐glucopyranosyl)‐(2S, 2′R, 3R,4E,8E)‐2‐(2′‐hydroxyhexadecanoylamino)‐4,8‐octdecadiene‐1,3‐diol (19), gallic acid (20), pinocembrin‐7‐O‐β‐D‐glucoside (21), and quercetin‐3‐O‐β‐D‐glucoside (22). The structures of these compounds were elucidated on the basis of chemical and spectral evidence.

Inhibitory activity of stilbenes on Alzheimer’s β-amyloid fibrils in vitro

Polymerization of the amyloid β-peptide (Aβ) has been identified as one of the major characteristics of Alzheimer’s disease (AD). Thus, finding molecules to prevent the aggregation of Aβ could be of therapeutic value in AD. We describe an original routine in vitro assay to search for inhibitors of Aβ(25–35) fibril formation which uses UV–visible measurements and electron microscopy (EM). In particular, this routine assay was used to examine the effects of stilbenes, a well-known polyphenol class, as inhibitors of Aβ fibril formation. The inhibitory properties of resveratrol (RES), piceid (PIC), resveratrol diglucoside (DIG), piceatannol (PIA), astringine (AST), and viniferin (VIN) were characterized and compared. RES and PIC effectively and dose-dependently inhibited Aβ polymerization while other polyphenols exerted less inhibition. Although the mechanism of anti-amyloidogenic activity is still unknown, these results support the hypothesis that stilbenes could be of therapeutic value in AD.

Synthesis of the first deprotected indigo N-glycosides (blue sugars) by reductive glycosylation of dehydroindigo

The first deprotected indigo N-glycosides (blue sugars) have been prepared by reaction of dehydroindigo with in situ generated rhamnosyl, glucosyl and mannosyl iodide.

A Study of Performance Properties of Alkyl Poly(Glucoside) and Sodium Dodecylsulfate in their Mixed Systems

The interaction parameters and performance properties such as solubilizing capacity and foaming behaviour of the aqueous Alkyl poly (glucoside) (APG)-sodium dodecylsulfate (SDS) mixed surfactant system have been investigated. The critical micellar concentrations (cmcs) obtained by surface tension measurements revealed that there is a synergism between these two surfactants. Performance properties such as solubilizing capacity have been investigated by measuring the absorbance and the viscosity of solubilized polar oily materials like octanol, decanol, dodecanol. The solubilizing phenomenon exhibited by mixed surfactant systems showed better results than that of the individual surfactant system. The foaming capacity of Alkyl poly (glucoside) with Sodium dodecylsulfate showed highly stabilized foaming behaviour in both distilled water as well as in hard water (324 ppm).

Allelopathic effect of cyanogenic glucosides on Nemaguard peach seedlings.

To evaluate the allelopathic effects of cyanoglucosides on Nemaguard ( Prunus persica x Prunus davidiana ) seedlings, cultivated in 4.5 L polyethylene bags with soil mixture without history of peach crop were treated with 0, 500, 1000 and 2000 mg·L -1 of amygdalin, bitter almond seed extracts, adult Nemaguard root extracts and a combination of the last two treatments. In addition, Nemaguard seedlings were cultivated in allelopathic soil from an old peach orchard cultivated for 50 years and having an amygdalin content of 258,6 mg·L -1 (14,7 mg·L -1 of cyanide). The allelopathic effects were determined by plant height, trunk diameter, total dry matter and root length. The soil residual cyanide content in the soil was determined at the end of the trial. Results showed for all growth parameters analyzed an increasing and detrimental effect according to applied concentrations of amygdalin or plant extracts. A polynomic relationship y = -8·10L -0.7 x 2 + 0.0031x + 0.0546 (R 2 = 0.96) best explained the relation between the concentration (x) of amygdalin and the cyanide residues (y) obtained. Para evaluar los efectos alelopaticos de cianoglucosidos en Prunus , plantulas de durazneros Nemaguard ( Prunus persica x P. davidiana ), mantenidas en bolsas de polietileno de 4,5 L en una mezcla de suelo sin historial de cultivo de duraznero recibieron los siguientes tratamientos alelopaticos, 0, 500, 1.000 y 2.000 mg·L -1 de amigdalina, extractos de semillas de almendro amargo, extracto de raices de Nemaguard adultos y una combinacion de los dosultimos tratamientos. Ademas se incluyo un tratamiento con suelo alelopatico, obtenido de un huerto cultivado por 50 anos con durazneros y caracterizado por presentar 258,6 mg·L -1 de amigdalina (14,7 mg·L -1 de cianuro residual). Los efectos alelopaticos se determinaron por la altura y diametro de las plantulas, por el peso seco total y la longitud radical. Al termino de esta evaluacion se determino la concentracion residual de cianuro en el suelo. De acuerdo con los resultados obtenidos hubo un efecto adverso, estadisticamente significativo, para todos los parametros de crecimiento analizados, creciente de acuerdo a la dosis de amigdalina aplicada y dependiente del extracto vegetales ocupado. Una relacion polinomial y = -8 ·10 -0,7 x 2 + 0,0031x + 0,0546 (R 2 = 0,96) explico la relacion entre la concentracion de amigdalina y el cianuro residual.

The influence of vitamin B1 and zinc sulphate to the polysaccharide production of shiitake mushroom (Lentinus edodes) and the immunomodulatory test on lymphocyte cells of Balb/c mice

Mushroom had been used for a long time as medicine. Shiitake (Lentinus edodes) which is known as one kind mushroom of wood, has very large benefit and various advantages. Shiitake consist of polysaccharide, which is known as lentinan, arrange on shape β-1,3 glucan with β-1,3 and β-1,6 glucopyranoside having immunomodulatory properties. These properties are important for treatment of tumor and cancer. The purpose of this research is to increase polysaccharide production in shiitake by adding various concentration of vitamin B1 and 1 mMol zinc sulphate which are known as cofactor on enzymatic reaction of polysaccharide metabolism via pentose phosphate pathway. These cofactor are added on the media of primordial phase of shiitake cultures.The concentration of polysaccharide was determined by modified phenol sulphuric acid test (AOAC Official Method of Analysis No. 988.12) and the immunomodulatory test was conducted by employing lymphocyte cells and the proliferation of these cells was determined by MTT reduction method. The result showed that the maximum production of polysaccharide was reached by adding 8% of vitamin B1 and this was followed by the increase of lymphocyte cells proliferation activity. Key words: shiitake, vitamin B1, zinc sulphate, polysaccharide, lymphocyte, proliferation.

Structural elucidation of glucosides and triterpenes by API-ionspray MS and tandem MS/MS spectrometry

API-ionspray MS and tandem MS/MS techniques were utilized to elucidate the structures of eight natural products consisting of lithospermoside and its two acetates, syringin and its two acetates, and two triterpenes-acetyloleanolic acid and methyloleanoate. Lithospermoside, syringin, and oleanolic acid were isolated and identified previously from Thalictrum rugosum (Ranuncularceae), Magnolia grandiflora (Magnoliaceae), and Eugenia javanica Lam. (Myrtaceae), respectively, on the basis of UV, IR ,NMR,MS (EI, CI) and CD data. In this investigation, apparent protonated molecular (MH^+), ammonium-adducted molecular (MNH4^+), and alkali-metal-adducted molecular (MNa^+ and MK^+) ions in the Q1 Scan MS spectra, and prominent as well as diagnostic product ions for structural elucidation in the tandem MS/MS spectra were observed for all investigated natural products each in nanogram quantities of material.

Phalerin, a new benzophenoic glucoside isolated from the methanolic extract of Mahkota Dewa [Phaleria macrocarpa (scheff). Boerl.] leaves

Mahkota Dewa [Phaleria macrocarpa (Scheff). Boerl.] is used traditionally to treat cancers in Indonesia. Extract methanol of the leaves displayed a small LC50 value (63.16 μg/ml) on BST (Brine Shrimp Lethality test) assay; therefore a phytochemical study of this extract was undertaken. A new benzophenoic glucoside was isolated from the methanol extract and identified as 4,5-dihydroxy,4’-methoxybenzophenone-3-0-β-D-glucoside (Phalerin) based on its spectroscopic data. Phalerin was cytotoxic to myeloma cell line (NS-1) (in vitro) having IC50 of 83 μg/ml or 1.9 x 10-1 mM. Key words: Phaleria macrocarpa, Phalerin, myeloma

Light Quality Influences Indigo Precursors Production And Seed Germination In Isatis tinctoria L. And Isatis indigotica Fort.

Isatis tinctoria L. and Isatis indigotica Fort. are biennial herbaceous plants belonging to the family of Cruciferae that are used as a source of natural indigo and show several morphological and genetic differences. Production of indigo (indigotin) precursors, indican (indoxyl beta-D glucoside) and isatan B (indoxyl ketogluconate), together with seed germination ability were compared in Isatis tinctoria and Isatis indigotica grown under six different light conditions (darkness, white, red, far red, blue, yellow light) at 25 degrees C. Light quality influenced both germination and production of indigo precursors in the two Isatis species. Different responsiveness to far red and blue light was observed. Indeed, a detrimental effect on germination by blue and far red light was found in I. tinctoria only. Different amounts of isatan B were produced under red and far red light in the two Isatis species. In I. tinctoria, the level of main indigo precursor isatan B was maximal under red light and minimal under far red light. Whereas in I. indigotica far red light promoted a large accumulation of isatan B. The photon fluence rate dependency for white and yellow light responses showed that the accumulation of indigo precursors was differently influenced in the two Isatis species. In particular, both white and yellow light enhanced above 40 micromol m(-2) s(-1) the production of isatan B in I. indigotica while only white light showed a photon fluence dependency in I. tinctoria. These results suggest a different role played by the labile and stable phytochrome species (phyA and phyB) in the isatan B production in I. tinctoria and I. indigotica. I. indigotica, whose germination percentage was not influenced by light quality, demonstrated higher germination capability compared with I. tinctoria. In fact, I. tinctoria showed high frequency of germination in darkness and under light sources that establish high phytochrome photoequilibrium (red, white and yellow light). Germination in I. tinctoria was negatively affected by far red and blue light. I. indigotica seeds appear to be indifferent to canopy-like light (far red). Our results provide further insights on the distinct behaviour of I. tinctoria and I. indigotica that belong to two different genetic clusters and different original environments.

Content of Resveratrols as a Function of Red Wine Cultivar and of the Year Production (2000-2001-2002)

As a continuation of a previous research project, the variability of trans - and cis -resveratrol and their glucosides in red wines, from 14 different species of vine, was determined. The wine came from grapes grown on two plots of land at two separate locations differing in pedo-climatic conditions. The content of total resveratrol is between 1.55 and 16.76 mg/L with an average value of 6.71 mg/L. Moreover the results showed that trans - and cis -resveratrol are more correlated (r = 0.83) than trans - and cis -glucoside (r = 0.72), due to the uniformity of vinification treatments. The species of vine, having a higher mean content of total resveratrol, are: Refosco, Pinot Nero, Ciliegiolo, Montepulciano e Gaglioppo. The data, elaborated by multivariate statistical analyses (Principal Component Analysis and Discriminant Analysis), pointed out a good separation between the three vintages as a function of resveratrol content.

Effects of Some Yeast on Resveratrol Content During Alcoholic Fermentation

The variability of the content of four monomeric forms of resveratrol (3, 5,4’-trihydroxystilbene): trans and cis -resveratrol, , trans and cis -β-Dglucopyranoside in musts of Cagnulari grapes grown in northwest Sardinia, using different strains of the yeast Saccharomyces cerevisiae , was determined by HPLC at different stages of vinification. The first sample was taken after three days, the second 10 days after inoculation of the yeasts and the third after the samples had been stored for two months at 10°C. The data were elaborated by multivariate statistical analysis, considering the variability of the concentrations of the four stilbene forms at different times. The results showed that from the beginning of sampling the form of resveratrol present in the highest amounts was the glucosylated form, but this had already decreased significantly in the second sample. The decrease in the glucosylated forms was not, however, accompanied by a proportional increase in the free forms. In addition, some yeast strains were identified that do not substantially change the total content of the four monomeric forms of resveratol.

New Phenylpropanoid Glycoside from Boschniakia rossica

From the whole plant of Boschniakia rossica (Cham. et Schlech.) Fedtsch. et Flerov., a new phenylpropanoid glycoside (2) was isolated together with fourteen known compounds which include two phenylpropanoid glycosides [rossicaside B (1) and rossicaside A (3)], triandrin (4), boschniakinic acid (5),two iridoid glucosides [boschnaloside(6), 8-epideoxyloganic acid (7)], three triterpenoids [3-epioleanolic acid (8), 3-epiacetyloleanolic acid (9), oleanolic acid (10)], β-sito-sterol (11), and four iridoid aglycones [1,10-bisdeoxy-7,8-dihydrogenipin (12), 7-methyl-octahy-dro-cyclopenta [c]pyran-4-carboxylic acid (13), (1R) and (1S) 1-O-methyl-8-epideoxyloganic acid aglycone (14, 15)].

清酒中に含まれるα-エチルグルコシドの新たな機能性

[in Japanese]

COMPOSITION OF THE ESSENTIAL OIL OF LONICERA HETEROPHYLLA DECNE.

Aerial parts of the plant (250 g) were collected during flowering in April 2000 from Tehran province in Iran. The essential oil was obtained by steam distillation of air-dried aerial parts in an all-glass apparatus. The sample oil that was light yellow in color was dried over anhydrous sodium sulfate and stored under nitrogen in a sealed vial until required. The essential oil was examined by GC and GC/MS. The components of the oil were identified by comparison of their mass spectra to those of a computer library or with authentic compounds and confirmed by comparison of their retention indices, either those of authentic compounds or data published in the literature The essential oil obtained by hydro-distillation from aerial parts of Lonicera heterophyla was examined by GC and GC/MS. Eleven compounds were characterized representing of about 85% of the total components detected. The major components were linalool (61.7%), (E)-?-ocimene (10.2%), ?-terpinene (7.9%) and p-cumene (7.4%). Other compounds of appreciable amounts are a-terpinene (6.1%), dihydrolinalool (1.8%) and terpinenyl acetate (1.7%). A literature search did not reveal any reference to previous work on the essential oil of this species but immunocytochemical localization of polygalacturonic acid (pectin) and methyl-esterified pectin in the walls of pollen tubes of 20 species of flowering horticultural and crop plants (including Jasminum humile) grown in vitro has been investigated. In addition, a secoiridoid glucoside +AFs-10-cinnamoyloxyoleoside 7-methyl ester +AF0- of Jasminum humile var. revolutum has been reported.

Meroterpenes and C-Glucosylflavonoids from the Aerial Parts of Plumbago zeylanica

Two meroterpenes bakuchiol and 12-hydroxyisobakuchiol, and three C-glucosylflavonoids, saponaretin, isoorientin and isoaffinetin together with other constituents plumbagin, isoshinano-lone, xanthyletin, xanthoxyletin, psoralen, plumbagic acid, plumbagic acid butyl ester, β-sitosterol and β-sitosteryl glucoside have been isolated from the aerial part of Plumbago zeylanica. This is the first report of isolation of meroterpenes and C-glucosylflavonoids from Plumbago species.

Solution‐Phase Hexasaccharide Synthesis Using Glucosyl Iodides.

Oligosaccharides composed of 1,6-glucosyl residues have been prepared from glucosyl iodides. The reactions are highly stereoselective, giving the α-glycosides as the only isolated products in yield...

Four new glycosides from Pleurospermum franchetianum

Four new glycosides, pleurofranosides I-IV, together with eight known compounds were isolated from the whole plants of Pleurospermum franchetianum Hemsl. Based on the spectral data and chemical evidence, the structures of pleurofranosides I, II, III and IV were elucidated to be 16 g , 21 g , 23, 28-tetrahydroxyolean-12-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 2)- g - d -glucopyranoside, 13 g , 28-epoxy-16 g , 23-dihydroxyolean-11-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 4)-[ g - d -glucopyranosyl-(1 M 2)]- g - d -fucopyranoside, 13 g , 28-epoxy-16 g , 23-dihydroxyolean-11-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 4)-[ g - d -fucopyranosyl-(1 M 2)]- g - d -glucopyranoside and 13 g , 28-epoxy-16 g , 23-dihydroxyolean-11-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 3)-[ g - d -glucopyranosyl-(1 M 2)]- g - d -glucopyranoside. The known compounds identified were octadecyl caprate, g -sitosterol, (22 E , 20 S , 24 R )-5 f , 8 f -epidioxy-ergosta-6, 22-dien-3- g -ol, daucosterol, f -spinasterol-3- O - g - d -glucopyranoside, quercetin-3, 7-di- O - g - d -glucopyranoside, kaempferol-3, 7-di- O - f - l -rhamnopyranoside and kaempferol-3- O - g - d -glucopyranosyl-7- O - f - l -rhamnopyranoside, respectively.

SYNTHESIS OF SOME GLYCOSIDES OF PYRIDINONE DERIVATIVES

ABSTRACT Synthesis of 3-cyano-4,6-dimethylpyridin-2-one ribosides, glucosides or galactosides is described, as well as 3-cyano-6-methylpyridin-2-one ribosides, glucosides and galactosides.

Level of "cis-" and "trans-" Resveratrol and Their Glucosides as a Function of Different Cultivar of Red Wines.

Variability of trans - and cis -resveratrol and their glucosides in red wines, coming from 13 different species of vine grown on two parallel plots of land, different for pedo-climatic conditions, during three different vintages, was determined by HPLC. The data obtained were elaborated by multivariate statistical analyses (Principal Component Analysis and Discriminant Analysis). The results showed that trans - and cis -resveratrol are more correlated than transand cis -glucoside, due to the uniformity of vinification treatments. Furthermore, Principal Component Analysis pointed out a good separation among five types of wine (Pinot noir, Malbeck, Gaglioppo, Refosco and Ciliegiolo), coming from the same cultivars, which are also discriminated in the Discriminant Analysis as a function of resveratrol content. This would underline that the cultivar variable, almost for the five above mentioned cultivars, has a higher influence than the other factors in wine characterisation with respect to their content of resveratrol.