The Composition of an Aldobionic Acid From Flaxseed Mucilage

Anderson, E. C.; Crowder, J. A.

doi:10.1021/ja01372a044

Cited by 26 publications

(11 citation statements)

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“…Whereas RG I, or at least polymers containing L-Rha and D-GalA, are abundant in all plant mucilages (Smith and Montgomery, 1959), flax mucilage is a mixture of RG I and arabinoxylan. Ironically, flax provided the first evidence for the repeating dimer of the RG I backbone (Anderson and Crowder, 1930;Tipson et al, 1939), yet its side group constitution is remarkably different from the descriptions in textbooks and major reviews of (1/4)-b-D-galactans, branched and unbranched (1/5)-a-L-arabinans, and type I arabinogalactans, all attached invariably at the O-4 position of the L-rhamnosyl residues of the RG I backbone (Darvill et al, 1980;McCann and Roberts, 1991;Carpita and Gibeaut, 1993;Carpita and McCann, 2000). In flax mucilage RG I, L-Fuc and the rare sugar, L-Gal, are attached almost exclusively at the O-3, not the O-4, position.…”

Section: Discussionmentioning

confidence: 99%

“…Acidic hydrolysates of flax mucilage yielded primarily an aldobiouronic acid (Neville, 1912), shown later to be a dimer of D-GalA and L-Rha (Anderson and Crowder, 1930). Identification of this aldobiouronic acid as a-Dgalactosyluronic acid-(1/2)-L-rhamnose (Tipson et al, 1939) is the earliest report in the literature of the repeating unit of the backbone of RG I. Flax mucilage was found to be a surprisingly good source of the rare sugar L-Gal (Anderson, 1933), and L-Ara and D-Xyl were also identified as significant neutral sugars in its composition (Anderson and Lowe, 1947;Easterby and Jones, 1950). More recently, the flax mucilage was characterized as a mixture of neutral arabinoxylans and strongly acidic rhamnose-containing polymers (Muralikrishna et al, 1987;Cui et al, 1994;Fedeniuk and Biliaderis, 1994;Warrand et al, 2005aWarrand et al, , 2005b.…”

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Novel Rhamnogalacturonan I and Arabinoxylan Polysaccharides of Flax Seed Mucilage

2008

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The viscous seed mucilage of flax (Linum usitatissimum) is a mixture of rhamnogalacturonan I and arabinoxylan with novel side group substitutions. The rhamnogalacturonan I has numerous single nonreducing terminal residues of the rare sugar L-galactose attached at the O-3 position of the rhamnosyl residues instead of the typical O-4 position. The arabinoxylan is highly branched, primarily with double branches of nonreducing terminal L-arabinosyl units at the O-2 and O-3 positions along the xylan backbone. While a portion of each polysaccharide can be purified by anion-exchange chromatography, the side group structures of both polysaccharides are modified further in about one-third of the mucilage to form composites with enhanced viscosity. Our finding of the unusual side group structures for two well-known cell wall polysaccharides supports a hypothesis that plants make a selected few ubiquitous backbone polymers onto which a broad spectrum of side group substitutions are added to engender many possible functions. To this end, modification of one polymer may be accompanied by complementary modifications of others to impart functions to heterocomposites not present in either polymer alone.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

Novel Rhamnogalacturonan I and Arabinoxylan Polysaccharides of Flax Seed Mucilage

2008

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“…Davis et al (1990), using 'H-and 13C-NMR spectroscopy, showed that an RG from retted flax contains short side chains of (14)-linked p-D-Gal units attached at the 0-4 of the rhamnosyl units of RG. In contrast, the flax-seed mucilage is rich in L-Gal, rather than D-Gal (Anderson and Lowe, 1947). The mucilage is also enriched in Rha, GalA, and Xyl, -but linkage analyses have not been reported.…”

Section: Dlscusslonmentioning

confidence: 92%

Cell-Wall Polysaccharides of Developing Flax Plants

Gorshkova¹,

Wyatt²,

Salnikov³

et al. 1996

Plant Physiol.

145

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Flax (Linum usitatissimum L.) is an agronomically important source of natural fibers, especially in areas where cotton cannot be grown. The United States is a major producer of "linseed" oil from seeds of the flax plants, whereas about 80% of the flax in eastern Europe is cultivated for fiber, with two-thirds of that produced in Russia. In addition to their use in spinning and weaving into fabrics, these fine but durable fibers have many other commercial and environmental uses (Oosten, 1988). Studies of the chemical composition of the fiber cells have focused on investigations of the processed fibers and fibers in intact and "retted" plants, and attempts have been made to characterize some of the key alterations caused by an extensive processing that has an impact on fiber quality.The fibers originate from procambial cells in the protophloem (Esau, 1977). Bundles of about a dozen cells each encircle the vascular cylinder and produce thick cellulosic walls that nearly fill the lumen at maturity. Mature fibers contain 60 to 70% cellulose (Sharma, 1986;Morvan et al., 1989;Lozovaya et al., 1990). Although the remaining material is rich in pectin, the noncellulosic polysaccharides have not been fully characterized (Davis et al., 1990;McDougall et al., 1993). After harvest, the plants are retted (by dew retting in the field or by warm-water retting in factories), a process that helps to dissociate the bundles of fibers from other parts of the stem. Retting results in degradation of some pectins to free the fiber bundles from the pectinrich sheaths of the cortical cells. Microbial endopolygalacturonase (Chesson, 1979) or cultures of Erwinia carotovora (Morvan et al., 1989) can be used to mimic the retting process. Unlike cotton fibers, which grow as single epidermal hair cells, the strength and integrity of the flax fibers rely to a certain extent on preservation of the cell-cell cementing during the retting process.Morvan and colleagues (Morvan et al., 1989;Davis et al., 1990) provided data on the monosaccharide composition and the linkage structure of the chelator-soluble pectic polysaccharides of flax plants and unprocessed fibers. McDougall(l993) has examined the noncellulosic polysaccharides of processed fibers. Because of the limited and sometimes contradictory information on the structure of the noncellulosic polysaccharides that accumulate during fiber development and remain after processing, we have examined the soluble and pectic polysaccharides and crosslinking glycans from various organs of the developing flax plant. In addition, the cortical cells, phloem, and developing fibers are easily peeled away from the vascular cylinder and analyzed separately. These studies permitted us to compare and contrast the specific changes in polysaccharide constituents that accompany fiber and xylem development.Abbreviations: AG(P), arabinogalactan(pr0tein); D (in chemical formulas), deuterium; GalA, galacturonic acid; GLC-EIMS, GLCelectron impact mass spectrometry; Mezh, cv Mezheumok; Novo, cv Novotorzhskii; Psko, cv Psko...

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“…The mucilage on flax hull comprises about 8% of the seed weight. It is primarily a mixture of polysaccharides composed of D-galacturonic acid, L-rhamnose, L-galactose and D-xylose units (Anderson and Lowe 1974;Erskine and Jones 1957;Fedeniuk and Biliaderis 1994). Flax is increasingly being recommended as a component of a healthy diets (Anonymous 2002;Oliff 2004).…”

Section: Flaxmentioning

confidence: 99%