Analysis Methods of Phytosterols

Analysis of Antioxidant-Rich Phytochemicals

Volumn , Issue , 2012, Pages 313-351

  Nyström, Laura ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Acylated steryl glycoside; Free sterol; Gammaoryzanol; Phytosterol; Plant sterol; Sterol conjugate; Steryl ester; Steryl ferulate; Steryl glycoside

Indexed keywords

EID: 84887147466     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118229378.ch10     Document Type: Chapter

References (96)

1. Abidi, S.L. 2001. Chromatographic analysis of plant sterols in foods and vegetable oils. J. Chromatogr. A. 935: 173-201.
2. Akihisa, T., Yasukawa, K., Yamaura, M., Ukiya, M., Kimura, Y., Shimizu, N., Arai, K. 2000. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects. J. Agric. Food Chem. 48: 2313-2319.
3. Akihisa, T., Ogihara, J., Kato, J., Yasukawa, K., Ukiya, M., Yamanouchi, S., Oishi, K. 2001. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 5: 507-512.
4. Aguilar-Garcia, C., Gavino, G., Baragano-Mosqueda, M., Hevia, P., Gavino, V.C. 2007. Correlation of tocopherol, tocotrienol, g-oryzanol and total polyphenol content in rice bran with different antioxidant capacity assays. Food Chem. 102: 1228-1232.
5. Awad, A.B., Fink, C.S. 2000. Phytosterols as anticancer dietary components: evidence and mechanism of action. J. Nutr. 130: 2127-2130.
6. Berger, A., Rein, D., Schafer, A., Monnard, I., Gremaud, G., Lambelet, P., Bertoli, C. 2005. Similar cholesterol-lowering properties of rice bran oil, with varied gammaoryzanol, in mildly hypercholesterolemic men. Eur. J. Nutr. 44: 163-173.
7. Berges, R.R., Windeler, J., Trampisch, H.J., Senge, T., Aeikens, B., Albrecht, J., Becker, C., Brundig, P., Dreyer, D., Kaldewey, W., Latka, H., Reek, A., Schneider, H.J., Schöter, P., Schumacher, C. 1995. Randomised, placebo-controlled, doubleblind clinical trial of b-sitosterol in patients with benign prostatic hyperplasia. Lancet 345: 1529-1532.
8. Bergman, C.J., Xu, Z. 2003. Genotype and environment effects on tocopherol, tocotrienol and g-oryzanol contents of Southern U. S. rice. Cereal Chem. 80: 446-449.
9. Bouic, P.J.D., Etsebeth, S., Liebenberg, R.W., Albrecht, C.F., Pegel, K., van Jaarsveld, P.P. 1996. Beta-sitosterol and beta-sitosterol glucoside stimulate human peripheral blood lymphocyte proliferation: Implications for their use as an immunomodulatory vitamin combination. Int. J. Immunopharmacol. 18: 693-700.
10. Bradford, P.G., Awad, A.B. 2010. Modulation of signal transduction in cancer cells by phytosterols. BioFactors 36: 241-247.
11. Bucci, R., Magri, A.D., Magri, A.L., Marini, F. 2003. Comparison of three spectrophotometric methods for the determination of gamma-oryzanol in rice bran oil. Anal. Bioanal. Chem. 375: 1254-1259.
12. Butsat, S., Siriamornpun, S. 2010. Antioxidant capacities and phenolic compounds of the husk, bran and endosperm of Thai rice. Food Chem. 119: 606-613.
13. Chigorimbo-Murefu, N.T.L., Riva, S., Burton, S.G. 2009. Lipase-catalyzed synthesis of esters of ferulic acid with natural compounds and evaluation of their antioxidant properties. J. Molec. Cat. B: Enzym. 56: 277-282.
14. Collins F.W., Fielder D.A., Sarr A. B., Redmond M. J., D Attilio, Robert Z. 2002. Process for the isolation, recovery and purification of nonpolar extractives, US Patent 6495140.
15. Diack, M., Saska M. 1994. Separation of vitamin E and g-oryzanols from rice bran by normal-phase chromatography. J. Am. Oil Chem. Soc. 71: 1211-1217.
16. EFSA, 2010. Scientific Opinion on the substantiation of health claims related to plant sterols and plant stanols and maintenance of normal blood cholesterol concentrations (ID 549, 550, 567, 713, 1234, 1235, 1466, 1634, 1984, 2909, 3140), and maintenance of normal prostate size and normal urination (ID 714, 1467, 1635) pursuant to Article 13(1) of Regulation (EC) No 1924/2006. EFSA J. 8: 1813.
17. Evershed, R.P., Goad, L.J. 1987. Capillary gas chromatography/mass spectrometry of cholesteryl esters with negative ammonia chemical ionization. Biomed. Environ. Mass Spectrom. 14: 131-140.
18. Evershed, R.P., Spooner, N., Prescott, M.C., Goad, L.J. 1988. Isolation and Characterization of intact steryl ferulates from seeds. J. Chromatogr. 440: 23-35.
19. Fang, N., Yu, S., Badger, T.H. 2003. Characterization of triterpene alcohol and steryl ferulates in rice bran using LC-MS/MS. J. Agric. Food Chem. 51: 3260-3267.
20. FDA, 2010. Proposed Rule: Food Labeling: Health Claim; Phytosterols and Risk of Coronary Heart Disease December 8, 2010. http://edocket.access.gpo.gov/2010/pdf/2010-30386.pdf
21. Galabov, A.S., Nikolaeva, L., Todorova, D., Milkova, T. 1998. Antiviral activity of cholesteryl esters of cinnamic acid derivatives. Z. Naturforsch. 53c: 883-887.
22. Gertz, C., Klostermann, S., Kochhar, S.P. 2000. Testing and comparing oxidative stability of vegetable oils and fats at frying temperature. Eur. J. Lipid Sci. Tech. 102: 543-551.
23. Goad, L.J., Akihisa, T. 1997. Analysis of Sterols. Blackie Academic and Professional, Chapman & Hall, London, Great Britain.
24. Gopala Krishna, A.G., Khatoon, S., Shiela, P.M., Sarmandal, C.V., Indira, T.N., Mishra, A. 2001. Effect of refining of crude rice bran oil on the retention of oryzanol in the refined oil. J. Am. Oil Chem. Soc. 78: 127-129.
25. Graf, E. 1992. Antioxidant potential of ferulic acid. Free Radic. Biol Med. 13: 435-448.
26. Gutierrez, A., del Rio, J.C. 2001. Gas chromatography/mass spectrometry demonstration of steryl glycosides in eucalypt wood, Kraft pulp and process liquids. Rapid Comm. Mass Spectrom. 15: 2515-2520.
27. Ha, T., Ko, S., Lee, S., Kim, H., Chung, S., Kim, S., Yoon, H., Kim, I. 2006. Changes in nutraceutical lipid components of rice at different degrees of milling. Eur. J. Lipid Sci. Tech. 108: 175-181.
28. Hakala, P., Lampi, A.-M., Ollilainen, V., Werner, U., Murkovic, M., Wähälä, K., Karkola, S., Piironen, V. 2002. Steryl phenolic acid esters in cereals and their milling fractions. J. Agric. Food Chem. 50: 5300-5307.
29. Huang, C.J., Xu, Z., Godber, J.S. 2009. Potential antioxidant activity of gammaoryzanol in rice bran as determined using an in vitro-mouse lymph axilliary endothelial model. Cereal Chem. 86: 679-684.
30. Islam, M.S., Murata, T., Fujisawa, M., Nagasaka, R., Ushio, H., Bari, A.M., Hori, M., Ozaki, H. 2008. Anti-inflammatory effects of phytosteryl ferulates in colitis induced by dextran sulphate sodium in mice. Br. J. Pharmacol. 154: 812-824.
31. Iwatsuki, K., Akihisa, T., Tokuda, H., Ukiya, M., Higashihara, H., Mukainaka, T., Iizuka, M., Hayashi, Y., Kimura, Y., Nishino, H. 2003. Sterol ferulates, sterols and 5-alk(en)ylresorcinols from wheat, rye, and corn bran oils and their inhibitory effects on Epstein-Barr virus activation. J. Agric. Food Chem. 51: 6683-6688.
32. Jones, P.J.H., AbuMweis, S.S. 2009. Phytosterols as functional food ingredients: linkages to cardiovascular disease and cancer. Curr. Opin. Clin. Nutr. Metab. Care 12: 147-151.
33. Juliano, C., Cossu, M., Alamanni, M.C., Piu, L. 2005. Antioxidant activity of gammaoryzanol: Mechanism of action and its effect on oxidative stability of pharmaceutical oils. Int. J. Pharmaceut. 299: 146-154.
34. Kamal-Eldin, A., Appelqvist, L.Å., Yousif, G., Iskander, G.M. 1992. Seed lipids of Sesamum indicum and related wild species in Sudan. The sterols. J. Sci. Food Agric. 59: 327-334.
35. Kamal-Eldin, A., Määttä, K., Toivo, J., Lampi, A., Piironen, V. 1998. Acid-catalyzed isomerization of fucosterol and D5-avenasterol. Lipids 33: 1073-1077.
36. Kesselmeier, J., Eichenberger, W., Urban, B. 1985. High performance liquid chromatography of molecular species from free sterols and steryl glycosides isolated from oat leaves and seeds. Plant Cell Physiol. 26: 463-471.
37. Kim, J.S., Suh, M.H., Yang, C.B., Lee, H.G. 2003. Effect of g-oryzanol on the flavor and oxidative stability of refrigerated cooked beef. J. Food Sci. 68: 2423-2429.
38. Kikuzaki, H., Hisamoto, M., Hirose, K., Akiyama, K., Taniguchi, H. 2002. Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem. 50: 2161-2168.
39. Kochhar, S.P. 2000. Stabilisation of frying oils with natural antioxidative components. Eur. J. Lipid Sci. Tech. 102: 552-559.
40. Khatoon, S., Gopala Krishna, A.G. 2004. Fat-soluble nutraceuticals and fatty acid composition of selected Indian rice varieties. J. Am. Oil Chem. Soc. 81: 939-943.
41. Kumar, R.R., Tiku, P.K., Prakash, V. 2009. Preferential extractability of g-oryzanol from dried soapstock using different solvents. J. Sci. Food Agric. 89: 195-200.
42. Lagarda, M.J., Garcia-Llatas, G., Farre, R. 2006. Analysis of phytosterols in foods. J. Pharmaceut. Biomed. Anal. 41: 1486-1496.
43. Lerma-Garcia, M.J., Herrero-Martinez, J.M., Simo-Alfonso, E.F., Mendonca, C.R.B., Ramis-Ramos, G. 2009. Composition, industrial processing and applications of rice bran g-oryzanol. Food Chem. 115: 389-404.
44. Lilitchan, S., Tangprawat, C., Aryusuk, K., Krisnangkura, S., Chokmoh, S., Krisnangkura, K. 2008. Partial extraction method for the rapid analysis of total lipid and g-oryzanol contents in rice bran. Food Chem. 106: 752-759.
45. Lin, X., Ma, L., Racette, S.B., Anderson Spearie, C.L., Ostlund, R.E. Jr.,. 2009. Phytosterol glycosides reduce cholesterol absorption in humans. Am. J. Phys. Gastroin. Liver Phys. 296: G931-G935.
46. Long, C.K.L., Lam, W.S., Chiu, L.C.M., Ooi, V.E.C., Sun, S.S.M., Wong, Y.-S. 2009. A rice bran polyphenol, cycloartenyl ferulate, elicits apoptosis in human colorectal adenocarcinoma SW480 and sensitizes metastatic SW620 cells to TRAIL-induced apoptosis. Biochem. Pharmacol. 77: 1487-1496.
47. Luo, H.-F., Li, Q., Yu, S., Badger, T.M., Fang, N. 2005. Cytotoxic hydroxylated triterpene alcohol ferulates from rice bran. J. Nat. Prod. 68: 94-97.
48. Marinova, E.M., Yanishlieva, N.V., Raneva, V.G., Todorova, D.I. 1998. Antioxidative action of the cholesteryl esters of ferulic and caffeic acids and their isomers. La Rivista Italiana Delle Sostanze Grasse. 75: 11-14.
49. Miller, A., Engel, K.H. 2006. Content of g-oryzanol and composition of steryl ferulates in brown rice (Oryza sativa L.) of European origin. J. Agric. Food Chem. 54: 8127-8133.
50. Moreau, R.A., Powell, M.J., Hicks, K.B. 1996. Extraction and quantitative analysis of oil from commercial corn fiber. J. Agric. Food Chem. 44: 2149-2154.
51. Moreau, R.A., Powell, M.J., Hicks, K.B., Norton, R.A. 1998. A Comparison of the levels of ferulate-phytosterol esters in corn and other seeds. In: Advances in Plant Lipid Research (Sanchez, J., Cerda-Olmedo, E., Martinez-Force, E.,Eds.) Universidad de Sevilla, Spain, pp. 472-474.
52. Moreau, R.A., Powell, M.J., Hicks, K.B. 2003a. Evaluation of a commercial enzymebased serum cholesterol test kit for analysis of phytosterol and phytostanol products. J. Agric. Food Chem. 51: 6663-6667.
53. Moreau, R.A., Powell, M.J., Singh, V. 2003b. Pressurized liquid extraction of polar and nonpolar lipids in corn and oats with hexane, methylene chloride, isopropanol and ethanol. J. Am. Oil Chem. Soc. 80: 1063-1067.
54. Moreau, R.A., Singh, V; Eckhoff, S.R., Powell, M.J., Hicks, K.B., Norton, R.A. 1999. Comparison of yield and composition of oil extracted from corn fiber and corn bran. Cereal Chem. 76: 449-451.
55. Moreau, R.A., Singh, V., Hicks, K.B. 2001. Comparison of oil and phytosterol levels in germplasm accessions of corn, teosinte, and job's tears. J. Agric. Food Chem. 49: 3793-3795.
56. Moreau, R.A., Whitaker, B.D., Hicks, K.B. 2002. Phytosterols, phytostanol, and their conjugates in foods: structural diversity, quantitative analysis, and health-promoting uses. Prog. Lipid Res. 41: 457-500.
57. Most, M.M., Tulley, R., Morales, S., Lefevre, M. 2005. Rice bran oil, not fiber, lowers cholesterol in humans. Am. J. Clin. Nutr. 81: 64-68.
58. Nagasaka, R., Shinoda, A., Ushio, H., Ohshima, T. 2008. g-Oryzanol in laminarian seaweeds (Abstract in English). Nippon Suisan Gakkaishi 74: 61-65.
59. Norton, R.A. 1995. Quantitation of steryl ferulate and p-coumarate esters from corn and rice. Lipids 30: 269-274.
60. Nurmi, T., Lampi, A., Nyström, L., Turunen, M., Piironen, V. 2010. Effects of genotype and environment on steryl ferulates in wheat and rye in the HEALTHGRAIN diversity screen. J. Agric. Food Chem. 58: 9332-9340.
61. Nyström, L., Achrenius, T., Lampi, A.-M., Moreau, R.A., Piironen, V. 2007a. A comparison of the antioxidant properties of steryl ferulates with tocopherol at high temperatures. Food Chem. 101: 947-954.
62. Nyström, L., Lampi, A.-M., Rita, H., Aura, A.-M., Oksman-Caldentey, K.-M., Piironen, V. 2007b. Effects of processing on availability of total plant sterols, steryl ferulates and steryl glycosides from wheat and rye bran. J. Agric. Food Chem. 55: 9059-9065.
63. Nyström, L., Mäkinen, M., Lampi, A.-M., Piironen, V. 2005. Antioxidant activity of steryl ferulate extracts from rye and wheat bran. J. Agric. Food Chem. 53: 2503-2510.
64. Nyström, L., Nurmi, T., Lampi, A.-M., Piironen, V. 2009. Chapter 2. Sterols. In: Analysis of Bioactive Components in Small Grain Cereals (Ward, J.L., Shewry, P. R.,Eds.) AACC Press, pp. 7-14.
65. Nyström, L., Paasonen, A., Lampi, A.-M., Piironen, V. 2007c. Total plant sterols, steryl ferulates and steryl glycosides in milling fractions of wheat and rye. J. Cereal Sci. 45: 106-115.
66. Nyström, L., Moreau, R.A., Lampi, A.-M., Hicks, K.B., Piironen V. 2008. Enzymatic hydrolysis of steryl ferulates and steryl glycosides. Eur. Food Res. Tech. 227: 727-733.
67. Ohtsubo, K., Suzuki, K., Yasui, Y., Kasumi, T. 2005. Bio-functional components in the processed pre-germinated brown rice by a twin-screw extruder. J. Food Comp. Anal. 18: 303-316.
68. Ostlund, R.E. Jr.,. 2002. Phytosterols in human nutrition. Ann. Rev. Nutr. 22: 533-549.
69. Parrado, J., Miramontes, E., Jover, M., Marquez, J.C., Angeles Mejias, M., Collantes De Teran, L., Absi, E., Bautista, J. 2003. Prevention of brain protein and lipid oxidation elicited by a water-soluble oryzanol enzymatic extract derived from rice bran. Eur. J. Nutr. 42: 307-314.
70. Pegel K.H. 1980. Sterolins and their use, U.S. Patent 4118379.
71. Piironen, V., Lampi, A.-M. 2004. Occurrence and levels of phytosterols in foods. In: Phytosterols as Functional Food Components and Nutraceuticals (Dutta, P.C., Ed.) CRC Press, Marcel Dekker Inc., New York, pp. 1-27.
72. Rahier, A., Benveniste, P. 1989. Mass spectral identification of phytosterols. In: Analysis of Sterols and Other Biologically Significant Steroids (Nes, W.D., Parish, E.J.,Eds.) Academic Press, San Diego, pp. 223-250.
73. Rogers,E.J., Rice, S.M., Nicolosi,R.J., Carpenter, D.R.;McClelland, C.A.;Romanczyk, L.J. Jr.,. 1993. Identification and quantification of g-oryzanol components and simultaneous assessment of tocols in rice bran oil. J. Am. Oil Chem. Soc. 70: 301-307.
74. Rohrer, C.A., Siebenmorgen, T.J. 2004. Nutraceutical concentrations within the bran of various rice kernel thickness fractions. Biosys. Eng. 88: 453-460.
75. Rong, N., Ausman, L.M. and Nicolosi, R.J. 1997. Oryzanol decreases cholesterol absorption and aortic fatty streaks in hamsters. Lipids 32: 303-309.
76. Seetharamaiah, G.S., Prabhakar, J.V. 1986. Oryzanol content of Indian rice bran oil and its extraction from soapstock. J. Food Sci. Tech. 23: 270-273.
77. Seitz, L.M. 1989. Stanol and sterol esters of ferulic and p-coumaric acids in wheat, corn, rye, and triticale. J. Agric. Food Chem. 37: 662-667.
78. Shen, J., Shao, X. 2005. A comparison of accelerated solvent extraction, Soxhlet extraction, and ultrasonic-assisted extraction for analysis of terpenoids and sterols in tobacco. Anal. Bioanal. Chem. 383: 1003-1008.
79. Smith, A.G., Brooks, C.J.W. 1976. Cholesterol oxidases: Properties and applications. Mini-Review. J. Steroid Biochem. 7: 705-713.
80. Stöggl, W., Huck, C., Wongyai, S., Scherz, H., Bonn, G. 2005. Simultaneous determination of carotenoids, tocopherols and, g-oryzanol in crude rice bran oil by liquid chromatography coupled to a diode array and mass spectrometric detection employing silica C30 stationary phases. J. Sep. Sci. 28: 1712-1718.
81. Tajima, K., Sakamoto, M., Okada, K., Mukai, K., Ishizu, K., Sakurai, H., Mori, H. 1983. Reaction of biological phenolic antioxidants with superoxide generated by cytochrome P-450 model system. Biochem. Biophys. Res. Comm. 115: 1002-1008.
82. Trautwein, E. A., Demonty, I. 2007. Phytosterols: natural compounds with established and emerging health benefits. Oleagineux, Corps Gras, Lipides 14: 259-266.
83. Waghorne, D., Ball, C.D. 1952. Semimicromethod for the determination of plant sterols. Anal. Chem. 24: 560-564.
84. Wang, T., Hicks, K.B., Moreau, R.A. 2002. Antioxidat activity of phytosterols, oryzanol, and other phytosterol conjugates. J. Am. Oil Chem. Soc. 79: 1201-1206.
85. Van Hoed, V., Depaemelaere, G., Vila Ayala, J., Santiwattana, P., Verhe, R., De Greyt, W. 2006. Influence of chemical refining on the major and minor components of rice bran oil. J. Am. Oil Chem. Soc. 83: 315-321.
86. van Rensburger, S.J., Daniels, W.M.U., van Zyl, J.M., Taljaard, J.J.F. 2002. A Comparative study of the effects of cholesterol, beta-sitosterol, beta-sitosterol glucoside, dehydro-epiandrosterone sulphate and melatonin on in vitro lipid peroxidation. Metab. Brain Dis. 15: 257-265.
87. Verleyen, T., Forcades, M., Verhe, R., Dewettinck, K., Huyghebaert, A., De Greyt, W. 2002. Analysis of free and esterified sterols in vegetable oils. J. Am. Oil Chem. Soc. 79: 117-122.
88. Winkler-Moser, J.K., Vaughn, S.F. 2009. Antioxidant activity of phytochemicals from distillers dried grain oil. J. Am. Oil Chem. Soc. 86: 1073-1082.
89. Wojciechowski, Z.A. 1991. Biochemistry of phytosterol conjugates. In: Physiology and Biochemistry of Sterols (Patterson, G.W., Nes, W.D.,Eds.) American Oil Chemists' Society, Champaign, Illinois, pp. 361-395.
90. Wu, Y.V., Norton, R.A. 2001. Enrichment of protein, starch, fat, and sterol ferulates from corn fiber by fine grinding and air classification. Ind. Crops Prod. 14: 135-138.
91. Xu, Z., Godber, J. S. 1999. Purification and identification of components of g-oryzanol in rice bran oil. J. Agric. Food Chem. 47: 2724-2728.
92. Xu, Z., Hua, N., Godber, J.S. 2001. Antioxidant activity of tocopherols, tocotrienols, and gamma-oryzanol components from rice bran against cholesterol oxidation accelerated by 2, 20-azobis(2-methylpropionamidine) dihydrochloride. J. Agric. Food Chem. 49: 2077-2081.
93. Yagi, K., Ohishi, N. 1979. Action of ferulic acid and its derivatives as antioxidants. J. Nutr. Sci. Vitaminol. 25: 127-130.
94. Yasukawa, K., Akihisa, T., Kimura, Y., Tamaura, T., Takido, M. 1998. Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in twostage carcinogenesis in mouse skin. Biol. Pharmaceut. Bull. 21: 1072-1076.
95. Zhou, M., Robards, K., Glennie-Holmes, M., Helliwell, S. 1999. Oat lipids. J. Am. Oil Chem. Soc. 76: 159-169.
96. Yoshida, K., Hirose, Y., Imai, Y., Kondo, T. 1989. Conformational analysis of cycloartenol, 24-methylenecycloartanol, and their derivatives. Agric. Biol. Chem. 53: 1901-1912.