Simultaneous analysis of free phytosterols/phytostanols and intact phytosteryl/phytostanyl fatty acid and phenolic acid esters in cereals

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 21, 2012, Pages 5330-5339

  Esche, Rebecca ^a   Barnsteiner, Andreas ^a   Scholz, Birgit ^a   Engel, Karl Heinz ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

cereals; solid phase extraction; sterols; steryl fatty acid ester; steryl phenolic acid ester

Indexed keywords

CEREALS; FATTY ACID ESTERS; PHENOLIC ACIDS; SOLID-PHASE EXTRACTION; STEROLS;

ALCOHOLS; ESTERIFICATION; ESTERS; GAS CHROMATOGRAPHY; GRAIN (AGRICULTURAL PRODUCT); LIPIDS; ORGANIC ACIDS; PHASE SEPARATION; PHENOLS; VEGETABLE OILS;

FATTY ACIDS;

ESTER; FATTY ACID; HYDROXYBENZOIC ACID DERIVATIVE; PHENOLIC ACID; PHYTOSTEROL; PLANT EXTRACT;

CEREAL; CHEMISTRY; MASS FRAGMENTOGRAPHY; REVIEW;

CEREALS; ESTERS; FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROXYBENZOIC ACIDS; PHYTOSTEROLS; PLANT EXTRACTS;

SECALE CEREALE; TRITICUM AESTIVUM; TRITICUM AESTIVUM SUBSP. SPELTA; ZEA MAYS;

EID: 84861596958     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf300878h     Document Type: Review

References (44)

1. Piironen, V.; Lindsay, D. G.; Miettinen, T. A.; Toivo, J.; Lampi, A.-M. Plant sterols: biosynthesis, biological function and their importance to human nutrition J. Sci. Food Agric. 2000, 80, 939-966
2. Brufau, G.; Canela, M. A.; Rafecas, M. Phytosterols: physiologic and metabolic aspects related to cholesterol-lowering properties Nutr. Res. (N.Y.) 2008, 28, 217-225
3. Calpe-Berdiel, L.; Escola-Gil, J. C.; Blanco-Vaca, F. New insights into the molecular actions of plant sterols and stanols in cholesterol metabolism Atherosclerosis 2009, 203, 18-31
4. Thompson, G. R.; Grundy, S. M. History and development of plant sterol and stanol esters for cholesterol-lowering purposes Am. J. Cardiol. 2005, 96, 3D-9D
5. Wang, T.; Hicks, K. B.; Moreau, R. Antioxidant activity of phytosterols, oryzanol, and other phytosterol conjugates J. Am. Oil Chem. Soc. 2002, 79, 1201-1206
6. Nyström, L.; Mäkinen, M.; Lampi, A.-M.; Piironen, V. Antioxidant activity of steryl ferulate extracts from rye and wheat bran J. Agric. Food Chem. 2005, 53, 2503-2510
7. Islam, M. S.; Murata, T.; Fujisawa, M.; Nagasaka, R.; Ushio, H.; Bari, A. M.; Hori, M.; Ozaki, H. Anti-inflammatory effects of phytosteryl ferulates in colitis induced by dextran sulphate sodium in mice Br. J. Pharmacol. 2008, 154, 812-824
8. Valsta, L. M.; Lemström, A.; Ovaskainen, M. L.; Lampi, A. M.; Toivo, J.; Korhonen, T.; Piironen, V. Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake Br. J. Nutr. 2004, 92, 671-678
9. Sioen, I.; Matthys, C.; Huybrechts, I.; Van Camp, J.; De Henauw, S. Consumption of plant sterols in Belgium: estimated intakes and sources of naturally occurring plant sterols and β-carotene Br. J. Nutr. 2011, 105, 960-966
10. Jiménez-Escrig, A.; Santos-Hidalgo, A. B.; Saura-Calixto, F. Common sources and estimated intake of plant sterols in the Spanish diet J. Agric. Food Chem. 2006, 54, 3462-3471
11. Määttä, K.; Lampi, A.-M.; Petterson, J.; Fogelfors, B. M.; Piironen, V.; Kamal-Eldin, A. Phytosterol content in seven oat cultivars grown at three locations in Sweden J. Sci. Food Agric. 1999, 79, 1021-1027
12. Nurmi, T.; Lampi, A.-M.; Nyström, L.; Piironen, V. Effects of environment and genotype on phytosterols in wheat in the HEALTHGRAIN diversity screen J. Agric. Food Chem. 2011, 58, 9314-9323
13. Piironen, V.; Toivo, J.; Lampi, A. M. Plant sterols in cereals and cereal products Cereal Chem. 2002, 79, 148-154
14. Harrabi, S.; St-Amand, A.; Sakouhi, F.; Sebei, K.; Kallel, H.; Mayer, P. M.; Boukhchina, S. Phytostanols and phytosterols distributions in corn kernel Food Chem. 2008, 111, 115-120
15. Jiang, Y.; Wang, T. Phytosterols in cereal by-products J. Am. Oil Chem. Soc. 2005, 82, 439-444
16. Ruibal-Mendieta, N. L.; Rozenberg, R.; Delacroix, D. L.; Petitjean, G.; Dekeyser, A.; Baccelli, C.; Marques, C.; Delzenne, N. M.; Meurens, M.; Habib-Jiwan, J.-L.; Quetin-Leclercq, J. Spelt (Triticum spelta L.) and winter wheat (Triticum aestivum L.) wholemeals have similar sterol profiles, as determined by quantitative liquid chromatography and mass spectrometry analysis J. Agric. Food Chem. 2004, 52, 4802-4807
17. Moreau, R. A.; Singh, V.; Hicks, K. B. Comparison of oil and phytosterol levels in germplasm accessions of corn, teosinte, and Job's tears J. Agric. Food Chem. 2001, 49, 3793-3795
18. Moreau, R. A.; Hicks, K. B. The composition of corn oil obtained by the alcohol extraction of ground corn J. Am. Oil Chem. Soc. 2005, 82, 809-815
19. Rocha, J. M.; Kalo, P. J.; Malcata, F. X. Neutral lipids in free, bound, and starch lipid extracts of flours, sourdough, and portuguese sourdough bread determined by NP-HPLC-ELSD Cereal Chem. 2011, 88, 400-408
20. Worthington, R. E.; Hitchcock, H. L. A method for the separation of seed oil steryl esters and free sterols: application to peanut and corn oils J. Am. Oil Chem. Soc. 1984, 61, 1085-1088
21. Verleyen, T.; Forcades, M.; Verhe, R.; Dewettinck, K.; Huyghebaert, A.; De Greyt, W. Analysis of free and esterified sterols in vegetable oils J. Am. Oil Chem. Soc. 2002, 79, 117-122
22. Gordon, M. H.; Miller, L. A. D. Development of steryl ester analysis for the detection of admixtures of vegetable oils J. Am. Oil Chem. Soc. 1997, 74, 505-510
23. Caboni, M. F.; Iafelice, G.; Pelillo, M.; Marconi, E. Analysis of fatty acid steryl esters in tetraploid and hexaploid wheats: identification and comparison between chromatographic methods J. Agric. Food Chem. 2005, 53, 7465-7472
24. Pelillo, M.; Iafelice, G.; Marconi, E.; Caboni, M. F. Identification of plant sterols in hexaploid and tetraploid wheats using gas chromatography with mass spectrometry Rapid Commun. Mass Spectrom. 2003, 17, 2245-2252
25. Phillips, K. M.; Ruggio, D. M.; Toivo, J. I.; Swank, M. A.; Simpkins, A. H. Free and esterified sterol composition of edible oils and fats J. Food Compos. Anal. 2002, 15, 123-142
26. Iafelice, G.; Verardo, V.; Marconi, E.; Caboni, M. F. Characterization of total, free and esterified phytosterols in tetraploid and hexaploid wheats J. Agric. Food Chem. 2009, 57, 2267-2273
27. Hakala, P.; Lampi, A.-M.; Ollilainen, V.; Werner, U.; Murkovic, M.; Wähälä, K.; Karkola, S.; Piironen, V. Steryl phenolic acid esters in cereals and their milling fractions J. Agric. Food Chem. 2002, 50, 5300-5307
28. Werner, U.; Lampi, A. M.; Ollilainen, V.; Piironen, V.; Murkovic, M. Analysis of steryl ferulates in rye as substances with cholesterol reducing capabilities Ernaehrung 2002, 26, 245-248
29. Nurmi, T.; Lampi, A.-M.; Nyström, L.; Turunen, M.; Piironen, V. Effects of genotype and environment on steryl ferulates in wheat and rye in the HEALTHGRAIN diversity screen J. Agric. Food Chem. 2010, 58, 9332-9340
30. Seitz, L. M. Stanol and sterol esters of ferulic and p -coumaric acids in wheat, corn, rye, and triticale J. Agric. Food Chem. 1989, 37, 662-667
31. Norton, R. A. Isolation and identification of steryl cinnamic acid derivatives from corn bran Cereal Chem. 1994, 71, 111-117
32. Miller, A.; Frenzel, T.; Schmarr, H.-G.; Engel, K.-H. Coupled liquid chromatography-gas chromatography for the rapid analysis of γ-oryzanol in rice lipids J. Chromatogr., A 2003, 985, 403-410
33. Barnsteiner, A.; Lubinus, T.; di Gianvito, A.; Schmid, W.; Engel, K.-H. GC-based analysis of plant stanyl fatty acid esters in enriched foods J. Agric. Food Chem. 2011, 59, 5204-5214
34. Horlacher, P.; Hietsch, D.; Albiez, W.; Timmermann, F.; Beck, K. World Intellectual Property Organization, http://www.wipo.int/patentscope/search/en/ WO2007101580 (accessed April 18, 2012).
35. Helm, R. F.; Ralph, J.; Hatfield, R. D. Synthesis of feruloylated and p -coumaroylated methyl glycosides Carbohydr. Res. 1992, 229, 183-194
36. Grabber, J. H.; Quideau, S.; Ralph, J. p -Coumaroylated syringyl units in maize lignin: implications for ether cleavage by thioacidolysis Phytochemistry 1996, 43, 1189-1194
37. Lu, F.; Ralph, J. Facile synthesis of 4-hydroxycinnamyl p -coumarates J. Agric. Food Chem. 1998, 46, 2911-2913
38. Höfle, G.; Steglich, W.; Vorbrüggen, H. 4-Dialkylaminopyridine als hochwirksame Acylierungskatalysatoren Angew. Chem. 1978, 90, 602-615
39. Chemische Analytik-Nachweis-, Erfassungs- und Bestimmungsgrenze unter Wiederholbedingungen-Begriffe, Verfahren, Auswertung. DIN 32645 2008-11.
40. Evershed, R. P.; Spooner, N.; Prescott, M. C.; Goad, L. J. Isolation and characterization of intact steryl ferulates from seeds J. Chromatogr. 1988, 440, 23-35
41. Norton, R. A. Quantitation of steryl ferulate and p -coumarate esters from corn and rice Lipids 1995, 30, 269-74
42. Nyström, L.; Moreau, R. A.; Lampi, A.-M.; Hicks, K. B.; Piironen, V. Enzymatic hydrolysis of steryl ferulates and steryl glycosides Eur. Food Res. Technol. 2008, 227, 727-733
43. Fenton, T. W.; Mueller, M. M.; Clandinin, D. R. Isomerization of some cinnamic acid derivatives J. Chromatogr. 1978, 152, 517-522
44. Hartley, R. D.; Jones, E. C. Effect of ultraviolet light on substituted cinnamic acids and the estimation of their cis and trans isomers by gas chromatography J. Chromatogr. 1975, 107, 213-218