A caffeoyl-fatty acid-glycerol ester from wax associated with green cotton fibre suberin

Schmutz, Alain; Jenny, Titus A.; Ryser, Ulrich

doi:10.1016/s0031-9422(00)89721-6

Cited by 50 publications

(40 citation statements)

References 18 publications

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“…2C) shows that, at least in Arabidopsis, root waxes have characteristics common to the monomers released upon depolymerization of root suberin (Franke et al, 2006;Beisson et al, 2007) and is thus suggestive of a metabolic relationship with aliphatic suberin. The fact that in green-lint cotton fibers the wax composition reflects in part the suberin composition (Schmutz et al, 1993(Schmutz et al, , 1994(Schmutz et al, , 1996 and that the Arabidopsis root wax compounds, apart from the simple MAGs, have also been found in isolated periderm of potato (Schreiber et al, 2005), clearly supports this view.…”

Section: Relationships Between Root Waxes and Aliphatic Suberinmentioning

confidence: 70%

“…However, this is still considered hypothetical (Schmutz et al, 1994(Schmutz et al, , 1996Schreiber et al, 2005). Because suberin is deposited outside the plasma membrane, but under the primary cell wall, a direct physical association between wax and suberin implies an extracellular location.…”

Section: Relationships Between Root Waxes and Aliphatic Suberinmentioning

confidence: 99%

“…Suberin-associated waxes are considered major contributors to the barrier for water diffusion across suberized cell walls (Soliday et al, 1979), but other factors controlling permeability remain to be identified (Schreiber et al, 2005). Green cotton (Gossypium hirsutum) fibers contain suberin and a significant amount of suberin-like waxes, including 1-(22-caffeyloxydocosanoyl)-glycerol as a major component (Schmutz et al, 1994).…”

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confidence: 99%

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Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

et al. 2007

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The interface between plants and the environment is provided for aerial organs by epicuticular waxes that have been extensively studied. By contrast, little is known about the nature, biosynthesis, and role of waxes at the root-rhizosphere interface. Waxes isolated by rapid immersion of Arabidopsis (Arabidopsis thaliana) roots in organic solvents were rich in saturated C18-C22 alkyl esters of p-hydroxycinnamic acids, but also contained significant amounts of both a-and b-isomers of monoacylglycerols with C22 and C24 saturated acyl groups and the corresponding free fatty acids. Production of these compounds in root waxes was positively correlated to the expression of sn-glycerol-3-P acyltransferase5 (GPAT5), a gene encoding an acyltransferase previously shown to be involved in aliphatic suberin synthesis. This suggests a direct metabolic relationship between suberin and some root waxes. Furthermore, when ectopically expressed in Arabidopsis, GPAT5 produced very-longchain saturated monoacylglycerols and free fatty acids as novel components of cuticular waxes. The crystal morphology of stem waxes was altered and the load of total stem wax compounds was doubled, although the major components typical of the waxes found on wild-type plants decreased. These results strongly suggest that GPAT5 functions in vivo as an acyltransferase to a glycerol-containing acceptor and has access to the same pool of acyl intermediates and/or may be targeted to the same membrane domain as that of wax synthesis in aerial organs.

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Section: Relationships Between Root Waxes and Aliphatic Suberinmentioning

confidence: 70%

Section: Relationships Between Root Waxes and Aliphatic Suberinmentioning

confidence: 99%

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confidence: 99%

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Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

et al. 2007

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“…However, partial depolymerization studies with suberin have shown that a large portion of the ferulate is esterified to the terminal hydroxy group of long-and very-long-chain v-OHFAs (Graça and Pereira, 2000;Graça and Santos, 2006). Likewise, a 22-caffeyloxy-docosanoyl glycerol has been isolated from cotton (Gossypium hirsutum) fiber waxes (Schmutz et al, 1994). In these cases an v-hydroxylase must provide the aliphatic substrate for the hydroxycinnamoyl transferase.…”

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confidence: 99%

Identification of an Arabidopsis Feruloyl-Coenzyme A Transferase Required for Suberin Synthesis

et al. 2009

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All plants produce suberin, a lipophilic barrier of the cell wall that controls water and solute fluxes and restricts pathogen infection. It is often described as a heteropolymer comprised of polyaliphatic and polyaromatic domains. Major monomers include v-hydroxy and a,v-dicarboxylic fatty acids, glycerol, and ferulate. No genes have yet been identified for the aromatic suberin pathway. Here we demonstrate that Arabidopsis (Arabidopsis thaliana) gene AT5G41040, a member of the BAHD family of acyltransferases, is essential for incorporation of ferulate into suberin. In Arabidopsis plants transformed with the AT5G41040 promoter:YFP fusion, reporter expression is localized to cell layers undergoing suberization. Knockout mutants of AT5G41040 show almost complete elimination of suberin-associated ester-linked ferulate. However, the classic lamellar structure of suberin in root periderm of at5g41040 is not disrupted. The reduction in ferulate in at5g41040-knockout seeds is associated with an approximate stoichiometric decrease in aliphatic monomers containing v-hydroxyl groups. Recombinant AT5G41040p catalyzed acyl transfer from feruloyl-coenzyme A to v-hydroxyfatty acids and fatty alcohols, demonstrating that the gene encodes a feruloyl transferase. CYP86B1, a cytochrome P450 monooxygenase gene whose transcript levels correlate with AT5G41040 expression, was also investigated. Knockouts and overexpression confirmed CYP86B1 as an oxidase required for the biosynthesis of very-long-chain saturated a,v-bifunctional aliphatic monomers in suberin. The seed suberin composition of cyp86b1 knockout was surprisingly dominated by unsubstituted fatty acids that are incapable of polymeric linkages. Together, these results challenge our current view of suberin structure by questioning both the function of ester-linked ferulate as an essential component and the existence of an extended aliphatic polyester.

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“…A caffeoyl-fatty acid-glycerol ester was isolated from the wax of green cotton fibers (Schmutz et al, 1993(Schmutz et al, , 1994b, and evidence was presented indicating that glycerol is also an important constituent of cotton fiber suberin (Schmutz et al, 1993). The immediate significance of this finding was obvious: The aliphatic monomers of cotton fiber suberin can only form linear polymers on their own, whereas glycerol allows the formation of a three-dimensional crosslinked network, as suggested by the lamellar ultrastructure and insolubility of suberin.…”

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confidence: 99%

Glycerol Is a Suberin Monomer. New Experimental Evidence for an Old Hypothesis1

et al. 1999

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The monomer composition of the esterified part of suberin can be determined using gas chromatography-mass spectroscopy technology and is accordingly believed to be well known. However, evidence was presented recently indicating that the suberin of green cotton (Gossypium hirsutum cv Green Lint) fibers contains substantial amounts of esterified glycerol. This observation is confirmed in the present report by a sodium dodecyl sulfate extraction of membrane lipids and by a developmental study, demonstrating the correlated accumulation of glycerol and established suberin monomers. Corresponding amounts of glycerol also occur in the suberin of the periderm of cotton stems and potato (Solanum tuberosum) tubers. A periderm preparation of wound-healing potato tuber storage parenchyma was further purified by different treatments. As the purification proceeded, the concentration of glycerol increased at about the same rate as that of ␣, -alkanedioic acids, the most diagnostic suberin monomers. Therefore, it is proposed that glycerol is a monomer of suberins in general and can cross-link aliphatic and aromatic suberin domains, corresponding to the electrontranslucent and electron-opaque suberin lamellae, respectively. This proposal is consistent with the reported dimensions of the electron-translucent suberin lamellae.Suberin and cutin are insoluble, lipophilic biopolymers. Together with complex mixtures of soluble lipids, they form the protective layers of higher plants: the cuticle of the epidermis and the suberin layers of the periderm and the exodermis. These cell layers are diffusion barriers for water and other

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A caffeoyl-fatty acid-glycerol ester from wax associated with green cotton fibre suberin

Cited by 50 publications

References 18 publications

Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

Identification of an Arabidopsis Feruloyl-Coenzyme A Transferase Required for Suberin Synthesis

Glycerol Is a Suberin Monomer. New Experimental Evidence for an Old Hypothesis1

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