Showing papers on "Glucoside published in 2005"

Cassava plants with a depleted cyanogenic glucoside content in leaves and tubers. Distribution of cyanogenic glucosides, their site of synthesis and transport, and blockage of the biosynthesis by RNA interference technology.

Abstract: Transgenic cassava (Manihot esculenta Crantz, cv MCol22) plants with a 92% reduction in cyanogenic glucoside content in tubers and acyanogenic (<1% of wild type) leaves were obtained by RNA interference to block expression of CYP79D1 and CYP79D2, the two paralogous genes encoding the first committed enzymes in linamarin and lotaustralin synthesis. About 180 independent lines with acyanogenic (<1% of wild type) leaves were obtained. Only a few of these were depleted with respect to cyanogenic glucoside content in tubers. In agreement with this observation, girdling experiments demonstrated that cyanogenic glucosides are synthesized in the shoot apex and transported to the root, resulting in a negative concentration gradient basipetal in the plant with the concentration of cyanogenic glucosides being highest in the shoot apex and the petiole of the first unfolded leaf. Supply of nitrogen increased the cyanogenic glucoside concentration in the shoot apex. In situ polymerase chain reaction studies demonstrated that CYP79D1 and CYP79D2 were preferentially expressed in leaf mesophyll cells positioned adjacent to the epidermis. In young petioles, preferential expression was observed in the epidermis, in the two first cortex cell layers, and in the endodermis together with pericycle cells and specific parenchymatic cells around the laticifers. These data demonstrate that it is possible to drastically reduce the linamarin and lotaustralin content in cassava tubers by blockage of cyanogenic glucoside synthesis in leaves and petioles. The reduced flux to the roots of reduced nitrogen in the form of cyanogenic glucosides did not prevent tuber formation.

In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer.

Abstract: Quercetin and quercetin glycosides are widely consumed flavonoids found in many fruits and vegetables. These compounds have a wide range of potential health benefits, and understanding the bioavailability of flavonoids from foods is becoming increasingly important. This study combined an in vitro digestion, a lactase treatment and the Caco-2 cell model to examine quercetin and quercetin glucoside uptake from shallot and apple homogenates. The in vitro digestion alone significantly decreased quercetin aglycone recovery from the shallot digestate (p 0.05). Digestion increased the Caco-2 cell uptake of shallot quercetin-4'-glucoside by 2-fold when compared to the non-digested shallot. Despite the loss of quercetin from the digested shallot, the bioavailability of quercetin aglycone to the Caco-2 cells was the same in both the digested and non-digested shallot. Treatment with lactase increased quercetin recovery from the shallot digestate nearly 10-fold and decreased quercetin-4'-glucoside recovery by more than 100-fold (p < 0.05), but had no effect on quercetin recovery from apple digestates. Lactase treatment also increased shallot quercetin bioavailability to the Caco-2 cells approximately 14-fold, and decreased shallot quercetin-4'-glucoside bioavailability 23-fold (p < 0.05). These Caco-2 cells had lactase activity similar to that expressed by a lactose intolerant human. The increase in quercetin uptake following treatment with lactase suggests that dietary supplementation with lactase may increase quercetin bioavailability in lactose intolerant humans. Combining the digestion, the lactase treatment and the Caco-2 cell culture model may provide a reliable in vitro model for examining flavonoid glucoside bioavailability from foods.

Antioxidative Phenols and Phenolic Glycosides from Curculigo orchioides

Abstract: A new orcinol glucoside, orcinol-1-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3), was isolated from the rhizomes of Curculigo orchioides GAERTN., together with seven known compounds: orcinol glucoside (1), orcinol-1-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2), curculigoside (4), curculigoside B (5), curculigoside C (6), 2,6-dimethoxyl benzoic acid (7), and syringic acid (8). The structures of these compounds were elucidated using spectroscopic methods. The antioxidant activities of these isolated compounds were evaluated by colorimetric methods based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. All the compounds showed potent antioxidative activities and the structure-activity relationship is discussed.

Indole alkaloids and other constituents of Rauwolfia serpentina.

Abstract: From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, N(b)-methylajmaline (1), N(b)-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed.

Analysis of the Transport Activity of Barley Sucrose Transporter HvSUT1

Abstract: Localization studies indicate that barley (Hordeum vulgare) sucrose transporter HvSUT1 functions in sucrose uptake into seeds during grain filling. To further understand the physiological function of HvSUT1, we have expressed the HvSUT1 cDNA in Xenopus laevis oocytes and analyzed the transport activity by two-electrode voltage clamping. Consistent with a H(+)-coupled transport mechanism, sucrose induced large inward currents in HvSUT1-expressing oocytes with a K (0.5) of 3.8 mM at pH 5.0 and a membrane potential of -157 mV. Of 21 other sugars tested, four glucosides were also transported by HvSUT1. These glucosides were maltose, salicin (2-(hydroxymethyl) phenyl beta-D-glucoside), alpha-phenylglucoside and alpha-paranitrophenylglucoside. Kinetic analysis of transport of these substrates by HvSUT1 was performed and K (0.5) values were measured. The apparent affinity for all substrates was dependent on membrane potential and pH with lower K (0.5) values at lower external pH and more negative membrane potentials. HvSUT1 was more selective for alpha-glucosides over beta-glucosides than the Arabidopsis sucrose transporter AtSUC2. Several substrates transported by AtSUC2 (beta-phenylglucoside, beta-paranitrophenylglucoside, alpha-methylglucoside, turanose, and arbutin (hydroquinone beta-D-glucoside)) showed low or undetectable transport by HvSUT1. Of these, beta-paranitrophenylglucoside inhibited sucrose transport by HvSUT1 indicating that it interacts with the transporter while arbutin and alpha-methyl glucoside did not inhibit. The results demonstrate significant differences in substrate specificity between HvSUT1 and AtSUC2.

C-aryl glucoside sglt2 inhibitors and method for their production

Abstract: A compound of the formula (I) A method is also provided for treating diabetes and related diseases employing the above compound alone or in combination with another therapeutic agent.

Characterisation of the phenolic profile of Boerhaavia diffusa L. by HPLC-PAD-MS/MS as a tool for quality control.

Abstract: Phenolic acids and flavonols of nine leaf and three root samples of Boerhaavia diffusa L., collected at different locations and subjected to several drying procedures, were characterised by reversed-phase HPLC-PAD-ESI/MS for the first time. Ten phenolic compounds were identified: 3,4-dihydroxy-5-methoxycinnamoyl-rhamnoside, quercetin 3-O-rhamnosyl(1-->6)galactoside (quercetin 3-O-robinobioside), quercetin 3-O-(2"-rhamnosyl)-robinobioside, kaempferol 3-O-(2"-rhamnosyl)-robinobioside, 3,5,4'-trihydroxy-6,7-dimethoxyflavone 3-O-galactosyl(1-->2)glucoside [eupalitin 3-O-galactosyl(1-->2)glucoside], caffeoyltartaric acid, kaempferol 3-O-robinobioside, eupalitin 3-O-galactoside, quercetin and kaempferol. Quantification was achieved by HPLC-PAD and two phenolic patterns were found for the leaves, in which quercetin 3-O-robinobioside or quercetin 3-O-(2"-rhamnosyl)-robinobioside was the major compound. Caffeoyltartaric acid was only present in the root material where it represented the main phenolic constituent. The results obtained demonstrated that the geographical origin (particularly the nature of the soil), but not the drying process, influences the phenolic composition.

A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa.

Abstract: A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2-4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated.

A Phenol Glucoside, Uncommon Coumarins and Flavonoids from Pelargonium sidoides DC

Abstract: Structural examination of the metabolic pool of the aerial parts of Pelargonium sidoides DC has led to the isolation of two new metabolites, 4-allyl-2,5-dimethoxyphenol-1-β-D-gluco-pyranoside and 6,7-dihydroxycoumarin-8-sulfate, along with a series of uncommon compounds including (2R,3R)-(+)-dihydroquercetin-3-β-glucopyranoside, (2R,3R)-(+)-dihydrokaempferol-3-β-glucopyranoside, fraxetin-7-β-glucopyranoside, 7-methoxycoumarin-6-β-glucopyranoside, umckalin, orientin-2"-gallate, and isoorientin-2"-gallate. They are accompanied by the widespread isoorientin, orientin, fraxetin, (2R,3S)-epigallocatechin-3-gallate, gallic acid and protocatechuic acid. The structures of the compounds were established from spectroscopic studies. Determination of configurations was achieved by circular dichroism.

Use of malic acid glucosides as flavouring substances

Abstract: The invention relates to the use of a malic acid glucoside [2-(glucosyl)-butane-1,4-diacid] or of a physiologically acceptable salt of a malic acid glucoside as flavouring substance, in particular as umami flavouring substance and taste intensifier.

Secondary metabolites of Phlomis viscosa and their biological activities

Abstract: Further phytochemical studies on the aerial parts of Phlomis viscosa (Lamiaceae) led to the isolation of 24 compounds: 3 iridoid glycosides, 10 phenylethanoid glycosides, a megastigmane glycoside and a hydroquinone glycoside, as well as 2 lignan glucosides and 7 neolignan glucosides, 1 of which is new (17b). Compound 17b was obtained as a minor component of an inseparable mixture (2:1) of 2 neolignan glucosides (17a/b), and characterized as 3',4-O-dimethylcedrusin 9-O-b -glucopyranoside. Full NMR data of the known 8-O-4' neolignan glucoside, erythro-1-(4-O-b-glucopyranosyl-3-methoxyphenyl)- 2-{2-methoxyl-4-[1-(E)-propene-3-ol]-phenoxyl}-propane-1,3-diol (18) are also reported. All isolated compounds were screened for cell growth inhibition versus 3 tumor cell lines (MCF7, NCI-H460, and SF-268) and several phenylethanoid glycosides were found to possess weak antitumoral activity. The phenylethanoid glycosides were also evaluated for their free radical (DPPH) scavenging, antibacterial and antifungal activities. The free radical (DPPH) scavenging activities of verbascoside (4), isoacteoside (5), forsythoside B (10), myricoside (13) and samioside (14) were found to be comparable to that of dl-a -tocopherol. Compounds 4, 5, 10 and 14 (MIC: 500 m g/mL) as well as Leucosceptoside A (8) and 13 (MIC:1000 m g/mL) showed very weak activity against Gram (+) bacteria.

Red clover Trifolium pratense L. phytoestrogens: UV-B radiation increases isoflavone yield, and postharvest drying methods change the glucoside conjugate profiles.

Abstract: Isoflavone extracts of red clover Trifolium pratense L. (cv. Pawera) with dissimilar glucoside conjugate profiles were obtained by employing different postharvest drying methods. The most prominent isoflavones found were formononetin and biochanin A and their corresponding glucosides and malonyl glucoside esters. Postharvest freeze drying inhibited the conversion of the glycosides to the aglycones, while vacuum drying allowed for maximum conversion of the glycosides to their corresponding aglycones. Air drying produced a low level of the aglycones formononetin and biochanin A, and oven drying promoted decarboxylation of the malonyl glucosides to the acetyl glucosides. Exposure to enhanced UV-B radiation resulted in an increase in total formononetin and biochanin A isoflavone levels, indicating that harvest during a period of high ambient UV-B radiation may be appropriate for maximum yield. The levels of caffeic acid and flavonols also increased by about 40 and 250%, respectively, on exposure to enhanced U...

Unexpected behavior of coniferin in lignin biosynthesis of Ginkgo biloba L

Abstract: To gain insight into the behavior of monolignol glucoside in Ginkgo biloba L., we examined glucosides potentially involved in lignin biosynthetic pathway. Coniferin (coniferyl alcohol 4O-beta-D-glucoside) is a strong candidate for the storage form of monolignol. Coniferaldehyde glucoside may also have a role in lignin biosynthesis; this was examined with tracer experiments using labeled glucosides fed to stem segments. A series of tracer experiments showed that coniferin and coniferaldehyde glucoside were modified into coniferyl alcohol and then efficiently incorporated into lignin under the experimental conditions used. Interestingly, more than half of the administered coniferin underwent an oxidation to the aldehyde form before its aglycone; coniferyl alcohol was polymerized into lignin. This suggests that there is an alternative pathway for coniferin to enter the monolignol biosynthetic pathway, in addition to the direct pathway beginning with the deglucosylation of coniferin catalyzed by beta-glucosidase. Enzymatic assays revealed that coniferaldehyde glucoside was produced enzymatically from coniferin, and that coniferaldehyde glucoside can be deglucosylated to yield coniferaldehyde, which could be fated to become coniferyl alcohol . Albeit the findings cannot be taken as proof for the in-planta functioning, these results present a possibility for the existence of alternative pathway in which some of the stored coniferin is oxidized to coniferaldehyde glucoside, which is deglucosylated to generate coniferaldehyde that joins the monolignol biosynthesis pathway.

Amaranthin in feather cockscombs is synthesized via glucuronylation at the cyclo-DOPA glucoside step in the betacyanin biosynthetic pathway.

Abstract: Uridine 5′-diphosphate (UDP)-glucuronic acid: cyclo-DOPA 5-glucoside glucuronosyltransferase activity was detected in a crude extract prepared from the purple flowers of feather cockscombs. This suggests that the glucuronic acid moiety of amaranthin and its derivatives may be introduced at the cyclo-DOPA glucoside step, but not at the betanidin glucoside step.

Synthesis of guaiacol-alpha-D: -glucoside and curcumin-bis-alpha-D: -glucoside by an amyloglucosidase from Rhizopus.

Abstract: Guaiacol (2-methoxyphenol) and curcumin [1E,6E-1,7-di(4-hydroxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione] were converted into their corresponding glucosides using glucose and an amyloglucosidase from Rhizopus. Guaiacol-α-D-glucoside yields ranged from 3 to 52% with the highest at pH 7.0. Curcumin-bis-α-D-glucoside yields ranged from 3 to 48% with the highest at pH 4.0 with 50% (w/w D-glucose) of enzyme. The phenolic hydroxyl group of guaiacol and both phenolic hydroxyl groups of curcumin were glucosylated at the C1 carbon of α-D-glucose indicating that the enzymatic reaction is stereospecific. Both guaiacol-α-D-glucoside and curcumin-bis-α-D-glucosides had antioxidant activities.

Isoflavonoid production by adventitious-root cultures of Iris germanica (Iridaceae)

Abstract: We established the adventitious-root cultures of Iris germanica, a monocotyledonous plant known for isoflavonoid production. Irigenin (5,7,3′-trihydroxy-6,4′,5′-trimethoxyisoflavone) and iristectorigenin A (5,7,3′-trihydroxy-6,4′-dimethoxyisoflavone) along with their 7-O-β-D-glucosides, iridin and iristectorin A, respectively, were found as the major components in adventitious roots in the liquid medium, and the total isoflavone content was about 3.6 µmol per g fresh weight in 3-week-old cultures, which was much higher than the 0.7 µmol per g dry weight in the rhizome previously reported (Ali et al. 1983 Phytochemistry 22: 2061). Abiotic stress was applied by addition of 3 mM cupric chloride (CuCl2) to the liquid medium. The isoflavone glucoside content was increased during the initial 6 h of CuCl2 treatment, which was followed by a decrease; the aglycone level continued to increase throughout the 48 h of treatment. The decrease in glucoside content was negatively correlated with the increase in aglycone content between 6 and 48 h. The total isoflavone content (glucosides+aglycones) at 6 h after the start of CuCl2 treatment was 1.4-fold the initial value, and nearly the same content was maintained for 48 h. Thus, the main effect of CuCl2 treatment appeared to be the induction of hydrolysis of isoflavone glucosides. A cDNA of chalcone synthase was cloned, and the mRNA was expressed in the culture producing isoflavones.

A dihydroflavonol glucoside from Commiphora africana that mediates DNA strand scission.

Abstract: A crude CH2Cl2−MeOH extract prepared from Commiphora africana was found to mediate Cu2+-dependent relaxation of supercoiled plasmid DNA. Bioassay-guided fractionation of this extract was carried out and was monitored by the use of an in vitro DNA strand scission assay. The dihydroflavonol glucoside phellamurin (1) was identified as the active principle responsible for the DNA cleavage activity of the crude extract.

Synthesis of hydroquinone-α-glucoside by α-glucosidasefrom baker’s yeast

Abstract: Hydroquinone-α-glucoside was synthesised from hydroquinone and maltose as glucosyl donor by transglucosylation in a water system with α-glucosidase from baker’s yeast. Only one phenolic –OH group was α-anomer-selectively glucosylated. The optimum conditions for transglucosylation reaction were at 30 °C for 20 h with 50 mM hydroquinone and 1.5 M maltose in 100 mM sodium citrate/phosphate buffer at pH 5.5. The glucoside was obtained at 0.6 mg/ml with a 4.6% molar yield with respect to hydroquinone.

Generation of (E)-1-(2,3,6-Trimethylphenyl)buta-1,3-diene from C13-Norisoprenoid Precursors

Abstract: Three C13-norisoprenoid compounds, 3,6,9-trihydroxymegastigma-4,7-diene (6), 3,4,9-trihydroxymegastigma-5,7-diene (4), and the actinidols (8), have all been synthesized and subjected to acid hydrolysis. All three were shown to generate (E)-1-(2,3,6-trimethylphenyl)buta-1,3-diene (1) under wine conservation conditions. At 45 °C, approximately 4000−5000 ng/L of 1 was formed from 1.0 mg/L of precursor, after 173 days, while at 25 °C more wine-like amounts (200−600 ng/L) were observed. A glucoside, 4,5-dihydrovomifoliol-C9-β-d-glucopyranoside (9b), was isolated from grapevine leaves by multilayer coil countercurrent chromatography (MLCCC), and its stereochemistry was deduced as being (5R, 6S, 9R) by NMR and CD spectroscopy. Hydrolysis of this glucoside produced 1, but in quantities insufficient to account for the levels observed in wine. Keywords: TPB; SIDA; polyphenols; grapes; precursors; C13-norisoprenoids; MLCCC.