Paper Electrophoresis of Carbohydrates

Weigel, Helmut

doi:10.1016/s0096-5332(08)60240-4

Cited by 72 publications

(32 citation statements)

References 33 publications

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“…Since fluorescent derivatives of myo-inositol are so far known to occur only as IAA esters in seeds, but not in fully differentiated plants (2), this unknown compound was isolated with the traditional means of column chromatography from T. baccata. From (1,13). If one of these hydroxyl groups is blocked by a methyl group or by ester formation, electrophoretic mobility is reduced (Table I).…”

Section: Resultsmentioning

confidence: 99%

Isolation and Characterization of a Novel p-Coumaric Acid Ester of myo-Inositol from Needles of Taxus baccata

Dittrich¹,

Danböck²

1977

Plant Physiol.

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A novel derivative of myo-inositol was isolated from the needles of Taxus baccata and identified as p-coumaric acid ester. By means of its levorotatory optical activity and formation of a borate complex, the compound was designated tentatively as a 1L-4-p-coumaroyl-myo-inosi-tol. Chemotaxonomic investigations have shown this ester to be present in needles of 14 out of 34 tested species of gymnosperms. When 14C02 or 14C-myo-inositol were fed to young needles of T. baccata, there was a rapid incorporation of label in the p-coumaroyl ester, and a pulse-chase experiment indicated a substantial turnover of this compound over a 4-month period. Myo-inositol is a carbohydrate which occurs in all biological systems, since phosphatidylinositol is an essential component of membrane structure. A number of other myo-inositol derivatives such as phosphates, glycosides, methyl ethers, and esters of organic acids also occur in plants (2, 3, 8, 9). The dominant group of ester derivatives is the indoleacetic acid esters, found so far only in seeds, where they might constitute a storage form of IAA during germination and early stages of plant development (2). Besides these IAA derivatives, only one acetic acid ester of myo-inositol was described to occur in Campanula (9). During our investigation of myo-inositol metabolism in gymnosperms and in Taxus baccata in particular, we detected a novel derivative of myo-inositol, namely an ester of p-coumaric acid. Our purpose in this paper is to describe the isolation of this compound , the elucidation of its structure, and its tentative role in metabolism. MATERIALS AND METHODS Plant Material. All plants used in this investigation were obtained from the Botanical Garden Munich. Isolation of pCI.' Needles of T. baccata were freeze-dried, ground to a fine powder, and extracted with ethylacetate to remove resins and other lipophilic compounds, and then extracted with hot methanol until all carbohydrates and phenolic compounds were eluted. The extract was concentrated at 50 C under vacuum and the resulting brown syrup (100 ml) was subjected to column chromatography in five batches on micro-crystalline cellulose with acetone-water (9:1, v/v) as eluting solvent. Samples of the fractions were dried on filter paper and examined for a compound, whose pale blue fluorescence in UV light of 350 nm reversibly changed to a bright blue color after exposure to ammonia vapors. The cellulose column chromatography was repeated three times to improve separation; the com

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Section: Resultsmentioning

confidence: 99%

Isolation and Characterization of a Novel p-Coumaric Acid Ester of myo-Inositol from Needles of Taxus baccata

Dittrich¹,

Danböck²

1977

Plant Physiol.

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“…Presaponified compound 17, on the other hand, yielded only the acid spot (data not shown). The identity of the putative [14C]Gal was confirmed by paper chromatography in EPW (which resolves it from Glc; see Fry, 1988) and by electrophoresis in molybdate (which resolves it from galactitol and glucitol; see Weigel, 1963) (data not shown).…”

Section: Susceptibility To Borohydride Reductionmentioning

confidence: 91%

“…10H20, adjusted to pH 5.0 with dilute H2SO,J was used at 2 kV for 3 h (Weigel, 1963). In both cases, picric acid was used as the mobile marker; the immobile marker (used to correct for electro-endo-osmosis) was Glc.…”

Section: High-voltage Electrophoresismentioning

confidence: 99%

Novel O-D-Galacturonoyl Esters in the Pectic Polysaccharides of Suspension-Cultured Plant Cells

Brown

Fry

1993

Plant Physiol.

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(50% yield of CalA3 in 7.2 min at p H 11 and 25°C). One of the three galacturonate residues i n compound 17 was reducible to a galactose residue with sodium borohydride, indicating that that CalA residue was esterified, via its -COOH group, to a putative alcohol. Compound 17 had a higher mobility than CalA3 on paper chromatography, indicating that the putative alcohol was relatively nonpolar. The putative alcohol could not have been methanol because Driselase readily hydrolyzed mono-, di-, and trimethyl esters of CalA3 to yield free galacturonic acid. Another Driselase digestion product (compound 12) was a derivative of CalA3 that apparently possessed two nonpolar esterified substituents: one about as labile as i n compound 17, and the other approximately 10 times more stable. Compounds 12 and 17 could not be labeled by in vivo feeding of [U-'4C]cinnamate, suggesting that they were not phenolic conjugates. Similar but chromatographically distinguishable ~ronate-'~C-labeled esters were obtained by Driselase digestion of walls of cultured carrot (Daucus carota L.), Paul's Scarlet rose (Rosa sp.), and tall fescue (festuca arundinacea Schreber) cells. In spinach, the novel compounds constituted about 5% of the total galacturonate residues of the cell wall. The observations suggest that pectic polysaccharides are linked, via 0-D-galacturonoyl ester bonds, to relatively hydrophobic constituents of the primary cell wall. Their possible role in wall architecture is discussed.Pectic polysaccharides (pectins) usually make up about one-third of the dry weight of the primary cell walls of dicots; smaller amounts are present in the Gramineae. Pectins are rich in (1+4)-linked a-D-galacturonate residues and also contain a-L-arabinose, 0-D-galactose, a-L-rhamnose, and numerous minor sugar residues (O'Neill et al., 1990). Several noncarbohydrate substituents are linked to pectins via ester bonds involving both carboxy and hydroxy groups of the polysaccharide. For example, many of the galacturonate residues are carboxy-esterified to methanol (Deuel and Stutz, 1958), a variable proportion of the galacturonate residues are 0-acetylated (Komalavilas and Mort, 1989), and (especially in the Chenopodiaceae) a few of the Ara and Gal residues are 0-feruloylated and 0-p-coumaroylated (Fry, 1982a). 993Several observations are consistent with the hypothesis that some pectins are cross-linked within the wall matrix via ester bonds (Fry, 1986). For example, a proportion of the CDTA-and endopolygalacturonase-inextractable pectin can be extracted from the cell wall in cold aqueous Na2C03 (e.g. 0.5 M; Selvendran and O'Neill, 1987;Ishii et al., 1989;Renard et al., 1990), a reagent that would break many types of ester bond. Also, suspension-cultured tomato cells that had been adapted to growth in the presence of 2,6-dichlorobenzonitrile possessed abnormal cell walls almost lacking cellulose and xyloglucan but composed largely of pectins, which became water soluble after treatment with alkali (Shedletzky et al., 1990). However, this type of eviden...

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“…Recently, we have found that some diols can be enantioseparated by the ligand-exchange CE (LECE) with borate anion as a central ion of the chiral selector [18,19] with the knowledge that 1,2-and 1,3-diols form moderately stable borate ester complexes in a weakly alkaline aqueous solution [20][21][22][23], where free borate ion, monocyclic, and dicyclic (spirocyclic) complexes coexist in the solution [24,25]. By using (S)-3-amino-1,2-propanediol (SAP) as the 1,2-diol selector ligand, DL-pantothenic acid, which has a 1,3-diol structure, was successfully resolved by the LECE [16] and the enantioseparation mechanism was also investigated [26].…”

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confidence: 99%

Simultaneous chiral resolution of monosaccharides as 8‐aminonaphthalene‐1,3,6‐trisulfonate derivatives by ligand‐exchange CE using borate as a central ion of the chiral selector

et al. 2007

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Six reducing monosaccharides (mannose, galactose, fucose, glucose, xylose, and arabinose) were derivatized with 8-aminonaphthalene-1,3,6-trisulfonate (ANTS). Based on the chiral ligand-exchange principle using borate as a central ion of the chiral selector and (S)-3-amino-1,2-propanediol (SAP) as a chiral selector ligand, all of the six ANTS-monosaccharides were simultaneously enantioseparated using absorbance at 245 nm for detection. The optimum conditions for both high resolution and moderately short migration time consisted of 200 mM SAP-200 mM borate buffer (pH 9.2) containing 10% ACN as a BGE at 30 degrees C with an applied voltage of +30 kV. It was revealed that the proposed chiral ligand-exchange CE using the SAP-borate system was applicable to enantioseparation of not only diols but also polyols.

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Paper Electrophoresis of Carbohydrates

Cited by 72 publications

References 33 publications

Isolation and Characterization of a Novel p-Coumaric Acid Ester of myo-Inositol from Needles of Taxus baccata

Isolation and Characterization of a Novel p-Coumaric Acid Ester of myo-Inositol from Needles of Taxus baccata

Novel O-D-Galacturonoyl Esters in the Pectic Polysaccharides of Suspension-Cultured Plant Cells

Simultaneous chiral resolution of monosaccharides as 8‐aminonaphthalene‐1,3,6‐trisulfonate derivatives by ligand‐exchange CE using borate as a central ion of the chiral selector

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