Extraction, structural characterisation and evaluation of hydroxycinnamate esters of orchard grass (Dactylis glomerata) as substrates for polyphenol oxidase

Phytochemistry

Volumn 69, Issue 16, 2008, Pages 2799-2806

  Parveen, Ifat ^a   Winters, Ana ^a   Threadgill, Michael D ^b   Hauck, Barbara ^a   Morris, Phillip ^a  

^a ABERYSTWYTH UNIVERSITY   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

Dactylis glomerata; Hydroxycinnamate esters; Hydroxycitric acid; Isocitric acid; Orchard grass; Polyphenol oxidase; Threonic acid

Indexed keywords

CATECHOL OXIDASE; COUMARIC ACID; ESTER; PHENOL DERIVATIVE;

ARTICLE; CHEMISTRY; DACTYLIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME SPECIFICITY; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METABOLISM;

CATECHOL OXIDASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARIC ACIDS; DACTYLIS; ESTERS; PHENOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTRATE SPECIFICITY;

DACTYLIS; DACTYLIS GLOMERATA;

EID: 56049105827     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.08.019     Document Type: Article

References (24)

1. Clifford M.N., Kellard B., and Birch G.G. Characterisation of chlorogenic acids by simultaneous isomerisation and transesterification with tetramethylammonium hydroxide. Food Chem. 33 (1989) 115-123
2. Clifford M.N., Wu W.G., and Kuhnert N. The chlorogenic acids of Hemerocallis. Food Chem. 95 (2006) 574-578
3. Corthout J., Pieters L., Claeys M., Vandenberghe D., and Vlietinck A. Antiviral caffeoyl esters from Spondias Mombin. Phytochemistry 31 (1992) 1979-1981
4. Crozier A. Methods in Polyphenol Analysis (2003), The Royal Society of Chemistry, Cambridge
5. Gowda L.R., and Paul B. Diphenol activation of the monophenolase and diphenolase activities of field bean (Dolchos lablab) polyphenol oxidase. J. Agric. Food Chem. 50 (2002) 1608-1614
6. Hahn R., and Nahrstedt A. Hydroxycinnamic acid derivatives, caffeoylmalic and new caffeoylaldonic acid esters, from Chelidonium majus. Planta. Medica. 59 (1993) 71-75
7. Hatcher D.W., and Kruger J.E. Distribution of polyphenol oxidase in flour millstreams of Canadian common wheat classes milled to 3 extraction rates. Cereal Chem. 70 (1993) 51-55
8. Hunt M.D., Eannetta N.T., Yu H.F., Newman S.M., and Steffens J.C. CDNA cloning and expression of potato polyphenol oxidase. Plant Mol. Biol. 21 (1993) 59-68
9. Lee D., Kang S.-J., Lee S.-H., Ro J., Lee K., and Kinghorn A.D. Phenolic compounds from the leaves of Cornus controversa. Phytochemistry 53 (2000) 405-407
10. Lee M.R.F., Colmenero J.D.O., Winters A.L., Scollan N.D., and Minchin F.R. Polyphenol oxidase activity in grass and its effect on plant-mediated lipolysis and proteolysis of Dactylis glomerata (orchard) in a simulated rumen environment. J. Sci. Food Agric. 86 (2006) 1503-1511
11. Marita, J.M., Hatfield, R.D., Brink, G.E., 2005. Polyphenol Oxidase Activity and In Vitro Proteolytic Inhibition in Grasses. XX International Grassland Congress 220.
12. Martinez M.V., and Whitaker J.R. The biochemistry and control of enzymatic browning. Trends. Food Sci. Technol. 6 (1995) 195-200
13. Mayer A.M. Polyphenol oxidases in plants and fungi: going places? A review. Phytochemistry 67 (2006) 2318-2331
14. Newman S.M., Eannetta N.T., Yu H.F., Prince J.P., Devicente M.C., Tanksley S.D., and Steffens J.C. Organization of the tomato polyphenol oxidase gene family. Plant Mol. Biol. 21 (1993) 1035-1051
15. Ozawa T., Nishikiori T., and Takino Y. Three new substituted cinnamoyl hydroxycitric acids from corn plant. Agric. Biol. Chem. 41 (1977) 359-367
16. Sarni-Manchado P., Cheynier V., and Moutounet M. Reactions of polyphenol oxidase generated caftaric acid o-quinone with malvidin 2-o-glocoside. Phytochemistry 45 (1997) 1365-1369
17. Siddiq M., Cash J.N., Sinha N.K., and Akhter P. Characterization and inhibition of polyphenol oxidase from pears. J. Food Biochem. 17 (1994) 327-337
18. Strack D., Leicht P., Bokern M., Wray V., and Grotjahn L. Hydroxycinnamic acid esters of isocitric acid: accumulation and enzymatic synthesis in Amaranthus Cruentus. Phytochemistry 26 (1987) 2919-2922
19. Sullivan M.L., and Hatfield R.D. Polyphenol oxidase and o-diphenols inhibit postharvest proteolysis in red clover and alfalfa. Crop Sci. 46 (2006) 662-670
20. Sun J., Jiang Y.M., Wei X.Y., Shi J., You Y.L., Liu H., Kakuda Y., and Zhao M. Identification of (-)-epicatechin as the direct substrate for polyphenol oxidase isolated from litchi pericarp. Food Res. Int. 39 (2006) 864-870
21. Swatsitang P., Tucker G., Robards K., and Jardine D. Isolation and identification of phenolic compounds in Citrus sinensis. Anal. Chim. Acta. 417 (2000) 231-240
22. Winters, A.L., Bryant, D.N., Gallagher, J.A., Lee, M.R.F., Minchin, F.R., Parveen, I, Theodorou, M.K., Morris, P., 2006. Biochemistry and molecular biology of polyphenol oxidases in grasses. International Conference on Polyphenols XXIII (22-25 August), University of Manitoba, Winnipeg, Canada.
23. Wong M.K., Dimick P.S., and Hammerstedt R.H. Extraction and high performance liquid-chromatographic enrichment of polyphenol oxidase from Theobroma-Cacao. J. Food Sci. 55 (1990) 1108-1111
24. Xu F., Geng Z.C., Sun J.X., Liu C.F., Ren J.L., Sun R.C., Fowler P., and Baird M.S. Fractional and structural characterization of hemicelluloses from perennial ryegrass (Lolium perenne) and orchard grass (Dactylis glomerata). Carbohydrate Res. 341 (2006) 2073-2082