Isolation and identification of triglycerides and ester oligomers from partial degradation of potato suberin

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 2, 2010, Pages 1040-1045

  Wang, Weimin ^a   Tian, Shiying ^a   Stark, Ruth E ^a,b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b CITY COLLEGE OF NEW YORK   (United States)

Author keywords

2D NMR; MS; NMR; Polyester; Potato; Solanum tuberosum; Suberin; Triacylglycerol; Triglyceride

Indexed keywords

ESTER; LIPID; PLANT EXTRACT; SUBERIN; TRIACYLGLYCEROL;

ARTICLE; CHEMISTRY; ISOLATION AND PURIFICATION; PLANT TUBER; POTATO;

ESTERS; LIPIDS; PLANT EXTRACTS; PLANT TUBERS; SOLANUM TUBEROSUM; TRIGLYCERIDES;

SOLANUM TUBEROSUM;

EID: 74849091684     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf902854y     Document Type: Article

References (31)

1. Kolattukudy, P. E. Polyesters in higher plants, Adv. Biochem. Eng. Biotechnol 2001, 71, 1-49.
2. Bernards, M. A. Demystifying suberin. Can. J. Bot. 2002, 80, 227-240.
3. Graça, J.; Santos, S. Suberin: the biopolyester of plants' skin. Macromol. Biosci. 2007, 7, 128-135.
4. Franke, R.; Schreiber, L. Suberin-a biopolyester forming apoplastic plant interfaces. Curr. Opin. Plant Biol. 2007, 10, 252-259.
5. Jarvinen, R.; Silvestre, A.; Holopainen, U.; Nyyssoola, A.; Gil, A. M.; Neto, C. P.; Lehtinen, P.; Buchert, J.; Kaltia, S. Suberin of potato (Solanum tuberosum var. Nikola); comparison of the effect of cutinase CcCut1 hydrolysis with chemical depolymerization. J. Agric. Food Chem. 2009, 57, 9016-9027.
6. Mattinen, M.-L.; Filpponen, I.; Jarvinen, R.; Li, B.; Kallio, H.; Lehtinen, P.; Argyropoulos, D. Structure of the polyphenolic component of suberin isolated from, potato (Solanum tuberosum var. Nicola). J. Agric. Food Chem. 2009, 57, 9747-9753.
7. Schmutz, A.; Jenny, T.; Ryser, U. A caffeoyl-fatty acid-glycerol ester from wax associated with green cotton fibre suberin. Phytochemistry 1994, 36, 1343-1346.
8. Graça, J.; Pereira, H, Diglycerol alkenedioates in suberin: building units of a poly(acylglycerol) polyester, Biomacromolecules 2000, 1, 519-522.
9. Ribas, I.; Blasco, E. Investigaciones sobre el corcho. I. Sobre la existencia de glicerina. Ann. R. Soc. Esp. Fis. Quim. 1940, 36B, 141-147.
10. Graça, J.; Pereira, H. Suberin structure in potato periderm.: glycerol, long-chain monomers, and glyceryl and feruloyl dimers. J. Agric. Food Chem. 2000, 48, 5476-5483.
11. (11) Moire, L.; Schmutz, A.; Buchala, A.; Yan, B.; Stark, R. E.; Ryser, U. Glycerol is a suberin monomer. New experimental evidence for an old hypothesis, Plant Physiol. 1999, 119, 1137-1146. (Pubitemid 29388286)
12. (12) Graça, J.; Pereira, H. Methanolysis of bark suberins: analysis of glycerol and acid monomers, Phytochem. Anal. 2000, 11, 45-51. (Pubitemid 30047860)
13. Schmutz, A.; Jenny, T.; Amrhein, N.; Ryser, U. Caffeic acid and glycerol are constituents of the suberin layers in green cotton, fibres. Planta 1993, 189, 453-460.
14. Rosa, E.; Pereira, H. The effect of long-term treatment at 100-150 C on structure, chemical composition and compression behaviour of cork. Holzforschung 1994, 48, 226-232.
15. Bento, M.; Pereira, H.; Cunha, M.; Moutinho, A.; van den Berg, K.; Boon, J. Thermally assisted transmethylation gas chromatographymass spectrometry of suberin components in cork, from Quercus suber L. Phytochem. Anal. 1998, 9, 1-13.
16. (16) Bonaventura, G.; Beisson, F.; Ohlrogge, J.; Pollard, M, Analysis of the aliphatic monomer composition of polyesters associated with Arabidopsis epidermis: occurrence of octadeca-cis-6, cis-9-diene-1,18-dioate as the major component, Plant J. 2004, 920-930. (Pubitemid 40047631)
17. Pollard, M.; Beisson, F.; Li, Y.; Ohlrogge, J. Building lipid barriers: biosynthesis of cutin and suberin. Trends Plant Sci 2008, 13, 236-246.
18. Bernards, M. A.; Lewis, N. G. Alkyl ferulates in wound healing potato tubers, Phytochemistry 1992, 31, 3409-3412.
19. Pacchiano, R. A.; Sohn, W.; Chlanda, V. L.; Garbow, J. R.; Stark, R. E. Isolation, and spectral characterization, of plant cuticle polyesters. J. Agric. Food Chem. 1993, 41, 78-83.
20. Bernards, M, A.; Lopez, M. L.; Zajicek, J.; Lewis, N. G. Hydroxycinnamic acid-derived polymers constitute the polyaromatic domain of suberin. J. Biol. Chem. 1995, 270, 7382-7386.
21. Yan, B.; Stark, R. E. A WISE NMR approach to heterogeneous biopolymer mixtures: dynamics and domains in wounded potato tissues. Macromolecules 1998, 31, 2600-2605.
22. Muller, L. Sensitivity enhanced detection of weak nuclei using heteronuclear multiple quantum coherence. J. Am. Chem. Soc. 1979, 101, 4481-4484.
23. 13C assignments from, sensitivity-enhanced detection, of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 1986, 108, 2093-2094.
24. Tian, S.; Fang, X.; Wang, W.; Yu, B.; Cheng, X.; Qiu, F.; Mort, A. J.; Stark, R. E. Isolation and identification of oligomers from partial degradation of lime fruit cutin. J. Agric. Food Chem. 2008, 56, 10318-10325.
25. Mcintyre, D. The analysis of triglycerides in edible oils by APCILC/ MS. Agilent Appl. Note 2000, 5968-0878E.
26. Osman, S. F.; Irwin, P. L.; Fett, W. F.; O'Connor, J. V.; Parris, N. Preparation, isolation, and characterization, of cutin monomers and oligomers from, tomato peels. J. Agric. Food Chem. 1999, 47, 799-802.
27. Walton, T. J.; Kolattukudy, P. E. Determination of the structures of cutin monomers by a novel depolymerization procedure and combined gas chromatography and mass spectrometry, Biochemistry 1972, 11, 1885-1896.
28. Holloway, P. J. Cutins of Malus pumila fruits and leaves. Phytochemistry 1973, 12, 2913-2920.
29. Gerard, H. C.; Osman, S. F.; Fett, W. F.; Moreau, R. Separation, identification, and quantification of monomers from cutin polymers by high-performance liquid chromatography and evaporative light-scattering detection, Phytochem. Anal. 1992, 3, 139-144.
30. Fang, X.; Qiu, F.; Yan, B.; Wang, H.; Mort, A. J.; Stark, R. E. NMR studies of molecular structure in fruit cuticle polyesters, Phytochemistry 2001, 57, 1035-1042.
31. Bovey, F. A.; Jelinski, L. W.; Mirau, P. A. Nuclear Magnetic Resonance Spectroscopy; Academic Press: San Diego, 1988.