Structure and composition of aliphatic constituents of potato tuber skin (suberin)

Kolattukudy, P. E.; Agrawal, Vishwanath Prasad

doi:10.1007/bf02532176

Cited by 168 publications

(137 citation statements)

References 15 publications

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“…The gravimetric results from the overnight reaction were comparable to results from the 3 h reflux reaction (monomer 3, 27%, SD 3%; residue 1, 57%, SD 1%; water-soluble, 16%, SD 1%), which resulted in complete depolymerization of the ester-bound suberin according to FT-IR and solid state 13 C NMR (see below). These results are consistent with previously published information for potato suberin (5,15).…”

Section: Resultssupporting

confidence: 94%

Suberin of Potato (Solanum tuberosum Var. Nikola): Comparison of the Effect of Cutinase CcCut1 with Chemical Depolymerization

Järvinen¹,

Silvestre²,

Holopainen³

et al. 2009

J. Agric. Food Chem.

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Chemical and enzymatic depolymerizations of suberin isolated from potato peel (Solanum tuberosum var. Nikola) were performed under various conditions. Enzymatic hydrolysis with cutinase CcCut1 and chemical methanolysis with NaOMe of suberin yielded monomeric fragments, which were identified as TMS derivatives with GC-MS and GC-FID. The solid, hydrolysis-resistant residues were analyzed with solid state 13 C CPMAS NMR, FT-IR, and microscopic methods. Methanolysis released more CHCl 3 -soluble material than the cutinase treatment when determined gravimetrically. Interestingly, cutinase-catalyzed hydrolysis produced higher proportions of aliphatic monomers than hydrolysis with the NaOMe procedure when analyzed by GC in the form of TMS derivatives. Monomers released by the two methods were mainly R,ω-dioic acids and ω-hydroxy acids, but the ratios of the detected monomers were different, at 40.0 and 32.7% for methanolysis and 64.6 and 8.2% for cutinase, respectively. Thus, cutinase CcCut1 showed higher activity toward ester bonds of R,ω-dioic acids than toward the bonds of ω-hydroxy acids. The most abundant monomeric compounds were octadec-9-ene-1,18-dioic acid and 18-hydroxyoctadec-9-enoic acid, which accounted for ca. 37 and 28% of all monomers, respectively. The results of the analyses of the chemical and enzymatic hydrolysis products were supported by the spectroscopic analyses with FT-IR and CPMAS 13 C NMR together with the analysis of the microstructures of the hydrolysis residues by light and confocal microscopy.

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Section: Resultssupporting

confidence: 94%

Suberin of Potato (Solanum tuberosum Var. Nikola): Comparison of the Effect of Cutinase CcCut1 with Chemical Depolymerization

Järvinen¹,

Silvestre²,

Holopainen³

et al. 2009

J. Agric. Food Chem.

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“…GLC-MS analysis of purified dihydro-p-coumaryl alcohol and dihydroconiferyl alcohol as di-TMS and diacetate derivatives gave peaks whose retention times were identical to those of synthetic standards (dihydro-p-coumaryl alcohol:di-TMS, 5 ample is represented by the gas chromatogram of the acetylated phenolic fraction obtained from peach cutin (Fig. 2).…”

Section: Isolation Of Phenolic Compounds From Cutin and Suberin Aftermentioning

confidence: 84%

Evidence for Covalently Attached p-Coumaric Acid and Ferulic Acid in Cutins and Suberins

Riley¹,

Kolattukudy²

1975

Plant Physiol.

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144

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p-Couimaric acid (4-hydroxycinnamic acid) and ferulic acid (4-hydroxy-3-methoxycinnamic acid) have been identified as conistituen-ts of cutin. Their reduction products were isolated fromi a phenolic fraction released from the cutin of the fruits of apple, peach, pear, and two varieties of tomato and apple leaf by treatment with LiAlH4 or LiAlD4. They were identified by comlibined gas chromatography and mass spectrormetry. p-Cotimaric acid was present in all samples of cutill (0.07-O.5i3% by weight), whereas only peach and pear cutin con-tainied measuirable aniotunits of ferulic acid (0.007% and 0.035.%, respectively). Both p-coutnaric acid and ferulic acid were idenitified to be conistituients of the insoluble material recovered after partial hydrolysis (12-42% loss) of cutin in 1 M NaOH at 80 C. A significanit part (48%) of the p-coumlaric acid contain-ed inl tomato cutin was contained in the insoluible material recovered after partial degradation (7.4%) of this cutin with 0.01 m NaOH. These data indicate that these phenolic components are tightly (possibly covalently) bountid to ctutin. Similar analysis of the phenolic fractions froni the stuberins of potato, sweet potato, turnip, rutabaga, carrot, anid red beet revealed that they contained onily fertilic acid (0.0.5-0.22%). Ferulic acid was identified as a constituen-t of the insoluible m-laterial recovered after partial hv-drolvsis of potato and beet suberins (34% and 32% loss, respectively) in 1 m NaOH at 80 C. A major part (65%) of the fertulic acid conitain-ed in potato suberin was contained in the inisoluble inaterial recovered after partial (26.8% loss) degradation of this suberin with 0.01 M NaOH. Fertulic acid appears to be tightly (probably covalently) bound to suiberin.Cutin, the structural component of plant cuticle, is a polymer of hydroxy fatty acids (8). The common major components of this polymer are palmitic acid, 16-hydroxypalmitic acid, 10,16-dihydroxypalmitic acid, or its positional isomers, oleic acid, 18-hydroxyoleic acid, 18-hydroxy-9, 10-epoxystearic acid, and 9, 10, 18-trihydroxystearic acid. The composition of the aliphatic components of suberin from the underground parts of plants is somewhat similar to that of cutin; however, there are significant quantitative differences between the composition of these two types of protective polymers (5-8). One major difference appears to be that suberin preparations contain quite large proportions of phenolic materials, while cutin preparations contain very little phenolic compounds, although the phenolics which might be present in cutin preparations have not been examined. In this paper we report experimental evidence which strongly suggests that p-coumaric acid and 'or ferulic acid are covalently attached to cutin and suberin. MATERIALS AND METHODS Isolation of Phenolic Compounds from Cutin and Suberin afterLiAlH1 and LiAID4 Degradation. Powdered cutin from apple leaf and fruits of apple, tomato, peach, and pear were obtained as previously described (11). A 500 mg sample of each cutin...

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“…Third, according to the current working hypothesis concerning the structure of suberin (11), the vascular coating would be expected to have a phenolic domain even though the nature ofthe aromatic components ofthis suberin remains unclear. Thus, the vascular coating process should require the expression of the gene for the peroxidase involved in the polymerization of the aromatic components of suberin.…”

Section: Discussionmentioning

confidence: 99%

“…Depolymerization and analysis of the aliphatic components of suberin were as previously described (11). The lyophilized material was finely ground with a Wig-L-Bug amalgamator (Crescent Manufacturing) and extracted in a Soxhlet apparatus for 48 h with CHCl3 and a further 48 h with CH30H.…”

Section: Analysis Of Suberinmentioning

confidence: 99%

Chemical Characterization of Stress-Induced Vascular Coating in Tomato

Robb¹,

Lee²,

Mohan³

et al. 1991

Plant Physiol.

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Indirect evidence suggests that vascular coatings formed by plants in response to stress consist of suberin-like substances containing lipid and phenolic compounds. To provide more direct chemical evidence that coatings are suberin, we used a natural pathogen, Verticillium albo-atrum, or a stress-responsive hormone, abscisic acid, to induce coating in two isolines of tomato (Lycopersicon esculentum L. cultivar Craigella) that are resistant or susceptible to the pathogen. Using treated petioles that had been monitored cytologically, chemical depolymerization followed by combined gas-liquid chromatography-mass spectrometry analysis of alkane-a,w-diol levels confirmed the presence of suberin after induction of coating and showed quantitative differences between the isolines that correlated with cytological measurements of the coating response. Northem analysis of suberization-associated anionic peroxidase mRNA showed corresponding increases, and tissue blot analysis further indicated that induction of the mRNA was localized in the responding vascular bundles, as determined by suberin histochemistry. Taken together, these results provide chemical evidence that the coatings are mainly suberin. Stress, whether biotic or abiotic, frequently induces the vascular coating response in plants (for review see ref. 19). A recent study (25) ofearly interactions between the wilt fungus, Verticillium albo-atrum, and its tomato host indicated that the coating of xylem vessel walls involves the secretion and deposition of normal or modified cell wall components. The nature of the polymeric materials deposited on the cell wall remains unknown. Although pathogen-induced wall coatings have been variously designated as lignin, induced lignin, lignin-like, and suberin, and although most studies have not satisfactorily distinguished between lignification and suberization, in most cases the deposits probably result from suberization (9, 15). The same process also is known to be injuryinduced in all plant organs (5).According to the current model, suberin consists of an aromatic domain and an aliphatic domain that is probably attached to the aromatic domain (10). The phenolic monomers derived from the phenylpropanoid pathway are polym-

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Structure and composition of aliphatic constituents of potato tuber skin (suberin)

Cited by 168 publications

References 15 publications

Suberin of Potato (Solanum tuberosum Var. Nikola): Comparison of the Effect of Cutinase CcCut1 with Chemical Depolymerization

Suberin of Potato (Solanum tuberosum Var. Nikola): Comparison of the Effect of Cutinase CcCut1 with Chemical Depolymerization

Evidence for Covalently Attached p-Coumaric Acid and Ferulic Acid in Cutins and Suberins

Chemical Characterization of Stress-Induced Vascular Coating in Tomato

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