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PLANT PHYSIOLOGY , Vol 103, Issue 3 993-999, Copyright © 1993 by American Society of Plant Biologists
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METABOLISM AND ENZYMOLOGY |
Novel O-D-Galacturonoyl Esters in the Pectic Polysaccharides of Suspension-Cultured Plant Cells
J. A. Brown and S. C. Fry
Daniel Rutherford Building, University of Edinburgh, The King's Buildings, Mayfield Road, Edinburgh EH9 3JH, United Kingdom
Driselase digestion of uronate-6-14C-labeled primary walls of cultured
spinach (Spinacia oleracea L.) cells yielded about 18 novel
uronate-containing compounds, most of which could be hydrolyzed by cold
dilute alkali to yield oligo-[14C]galacturonides. One typical Driselase
digestion product (compound 17) yielded [alpha]-(1->4) -D-
[14C]galacturonotriose (GalA3) upon very mild treatment with alkali (50%
yield of GalA3 in 7.2 min at pH 11 and 25[deg]C). One of the three
galacturonate residues in compound 17 was reducible to a galactose residue
with sodium borohydride, indicating that that GalA residue was esterified,
via its [mdash]COOH group, to a putative alcohol. Compound 17 had a higher
mobility than GalA3 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 GalA3 to yield free galacturonic acid. Another Driselase
digestion product (compound 12) was a derivative of GalA3 that apparently
possessed two nonpolar esterified substituents: one about as labile as in
compound 17, and the other approximately 10 times more stable. Compounds 12
and 17 could not be labeled by in vivo feeding of [U-14C]cinnamate,
suggesting that they were not phenolic conjugates. Similar but
chromatographically distinguishable uronate-14C-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 O-D-galacturonoyl ester bonds,
to relatively hydrophobic constituents of the primary cell wall. Their
possible role in wall architecture is discussed.
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