Functionality of compounds contained in rice bran and their improvement

Nippon Shokuhin Kagaku Kogaku Kaishi

Volumn 59, Issue 7, 2012, Pages 301-318

  Taniguchi, Hisaji ^a   Hashimoto, Hiroyuki ^b   Hosoda, Asao ^a   Kometani, Takashi ^c   Tsuno, Takuo ^b   Adachi, Shuji ^d  

^a Industrial Technology Center of Wakayama   (Japan)

^b Tsuno Food Industrial Co Ltd   (Japan)

^c KINKI UNIVERSITY   (Japan)

^d KYOTO UNIVERSITY   (Japan)

Author keywords

oryzanol; Ceramide; Ferulic acid; Functionality; Health promotion; Inositol; Phytin; Protein; Rice bran; Sterol; Wax

Indexed keywords

ANIMALIA; BASIDIOMYCOTA;

EID: 84866900479     PISSN: 1341027X     EISSN: None     Source Type: Journal    
DOI: 10.3136/nskkk.59.301     Document Type: Review

References (92)

1. Taniguchi, H., Nomura, E., Tsuno, T., Minami, S., Kato, K. and Hayashi, C., Method of manufacturing ferulic acid. U. S. Patent 5, 288, 902, Feb. 22, 1994.
2. Taniguchi, H., Hosoda, A., Tsuno, T., Maruta, Y. and E. Nomura, Preparation of ferulic acid and its application for the synthesis of cancer chemopreventive agents. Anticancer Res., 19, 3757-3761 (1999).
3. Han, B. S., Park, C. B., Takasuka, N., Naito, A., Sekine, K., Nomura, E., Taniguchi, H., Tsuno, T. and Tsuda, H., A ferulic acid derivative, ethyl 3-(4,-geranyloxy-3-methoxyphenyl)-2-propenoate, as a new candidate chemopreventive agent for colon carcinogenesis in the rat. Jpn. J. Cancer Res., 92, 404-409 (2001). (Pubitemid 32427776)
4. Fujita, A., Sasaki, H., Doi, A., Okamoto, K., Matsuno, S., Furuta, H., Nishi, M., Nakao, T., Tsuno, T., Taniguchi, H. and Nanjo, K., Ferulic acid prevents pathological and functional abnormalities of the kidney in Otsuka Long-Evans Tokushima Fatty diabetic rats. Diabetes Research and Clinical Practice, 79, 11-17 (2008).
5. Kikuzaki, H., Hisamoto, M., Hirose, K., Akiyama, K. and Taniguchi, H., Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem., 50, 2161-2168 (2002). (Pubitemid 34260027)
6. Tsuno, T., Maruta, Y., Hosoda, A., Nomura, E. and Taniguchi, H., Preparation of a novel thermally stable UV absorbent from natural resources. ITE Lett., 2, 808-811 (2001).
7. Hosoda, A., Nomura, E., Mizuno, K. and Taniguchi, H., Preparation of a 1, 6-di-O-feruloyl-myo-inositol derivative: an efficient method for introduction of ferulic acid to 1, 6-vicinal hydroxy groups of myo-inositol. J. Org. Chem., 66, 7199-7201 (2001). (Pubitemid 32983114)
8. http://beta.irri.org/solutions/index.php?option=com-content&task= view&id=250 (Nov. 9th, 2011).
9. http://www.e-stat.go.jp/SG1/estat/List do? lid=000001061500 (Nov. 9th, 2011).
10. Yuki, E. and Ishikawa, Y., Tocopherol contents of nine vegetable frying oils, and their changes under simulated deep-fat frying conditions. J. Am. Oil Chem. Soc, 53, 673-676 (1976).
11. Nicolosi, R. J., Ausma, L. M. and Hegsted, D. M., Rice bran oil lowers serum total and low density lipoprotein cholesterol and Apo B levels in non-human primates. Atherosclerosis, 88, 133-142 (1991).
12. Sierra, S., Lara-Villoslada, F., Olivares, M., Jimenez, J., Boza, J. and Xaus, J., Increased immune response in mice consuming rice bran oil Eur. J. Nutr., 44, 509-516 (2005). (Pubitemid 41752642)
13. Hsieh, R., Lien, L., Lin, S., Chen, C., Cheng, H. and Chen, H., Alleviation of oxidative damage in multiple tissues in rats with Streptozotocin-induced diabetes by rice bran oil supplementation. Ann. N. Y. Acad. Sci., 1042, 365-371 (2005). (Pubitemid 40967658)
14. Fujiwara, S., Sakurai, S., Sugimoto, I. and Awata, N., Absorption and metabolism of gamma-oryzanol in rats. Chem. Pharm. Bull., 31, 645-652 (1983).
15. Khuwijitjaru, P., Yuenyong, T., Pongsawatmanit, R. and Adachi, S., Degradation kinetics of gamma-oryzanol in purified rice bran oil during thermal oxidation. J. Oleo Sci., 58, 491-497 (2009).
16. Islam, M. S., Murata, T., Fujisawa, M., Nagasaka, R., Ushio, H., Bari, A. M., Hori, M. and Ozaki, H., Anti-inflammatory effects of phytosteryl ferulates in colitis induced by dextran sulphate sodium in mice. Br. J. Pharmacol., 154, 812-824 (2008). (Pubitemid 351821588)
17. Okajima K., Major components of rice bran, thiamine, gamma-oryzanol and gamma-aminobutyric acid increase insulin-like growth factor-I production through sensory neuron activation; the molecular mechanism (s) and biological effects. Abstracts of the Second International Symposium on Rice and Disease Prevention, p. 44 (2008).
18. Warth, A. H., "The Chemistry and Technology of Waxes", Reinhold Publishing Corp., New York, p. 241 (1956).
19. Pollard, A., Chibnall, A. C. and Piper, S. H., The isolation of n-octacosanol from wheat wax. Biochem. J., 27, 1889-1893 (1933).
20. Cureton, T. K., "The Physiological Effect of Wheat Germ Oil in Human in Exercise", ed. by C. C. Thomas, Springfield, IL (1972).
21. Taylor, J. C., Rapport, L. and Lockwood, G. B., Octacosanol in human health. Nutrition, 19, 192-195 (2003). (Pubitemid 36194488)
22. Kato, S., Karino, K.-I., Hasegawa, S., Nagasawa, J., Nagasaki, A., Eguchi, M., Ichinose, T., Tago, K., Okumori, H., Hamatani, K., Takahashi, M., Ogasawara, J., Masushige, S. and Hasegawa T., Octacosanol affects lipid metabolism in rats fed on a high-fat diet. Br. J. Nutr., 73(3), 433-441 (1995).
23. Arruzazabala, M. L., Carbajal, D., Mas, R., Garcia M. and Fraga V., Effects of policosanol on platelet aggregation in rats. Thromb. Res., 69, 321-327 (1993). (Pubitemid 23080708)
24. Stusser, R., Batista, J., Padron, R., Sosa, F and Pereztol, O., Long-term therapy with policosanol improves treadmill exercise-ECG testing performance of coronary heart disease patients. Int. J. Clin. Pharmacol. Ther., 36, 469-473 (1998). (Pubitemid 28430231)
25. Singh, D. K., Li, L. and Porter, T. D., Policosanol inhibits cholesterol synthesis in hepatoma cells by activation of AMP-kinase. J. Pharmacol. Exp. Ther., 318, 1020-1026 (2006). (Pubitemid 44268306)
26. Thippeswamy, G., Sheela, M. L. and Salimath, B. P., Octacosanol isolated from Tinospora cordifolia downregulates VEGF gene expression by inhibiting nuclear translocation of NF-kB and its DNA binding activity. Eur. J. Pharmacol, 588, 141-150 (2008).
27. Serbinova E., Kagan, V., Han, D. and Packer, L., Free radical recycling and intramembrane mobility in the antioxidant properties of alpha-tocopherol and alpha-tocotrienol. Free Radic. Biol Med, 10, 263-275 (1991). (Pubitemid 121003898)
28. Grases, F., Simonet, B. M., Vucenik, I., Prieto, R. M., Costa-Bauzá, A., March, J. G and Shamsuddin, A. M., Absorption and excretion of orally administered inositol hexaphosphate (IP-6 or phytate) in humans. BioFactors, 15, 53-61 (2001). (Pubitemid 34014664)
29. Bohn, L., Meyer, A. S. and Rasmussen, S. K., Phytate: impact on environment and human nutrition. A challenge for molecular breeding. J. Zheijang Univ. Sci. B, 9, 165-191 (2008). (Pubitemid 351447794)
30. Vucenik, I. and Shamsuddin, A. M., Protection against cancer by dietary IP6 and inositol. Nutri. Cancer, 55, 109-125 (2006). (Pubitemid 44719624)
31. Ogasa, K., Kuboyama M., Kiyosawa I, Suzuki, T. and Itoh, M., The content of free and bound inositol in human and cow's milk J. Nutr. Sci. Vitaminol., 21(2), 129-135 (1975).
32. Clements, R. S., Jr. and Darnell, B., myo-Inositol content of common foods, development of a high-myo-inositol diet. Am. J. Clin. Nutr., 33, 1954-1967 (1980).
33. Lam, S., McWilliams, A., IeRiche, J., MacAulay, C., Wattenberg, L. and Szabo, E., A phase I study of myo-inositol for lung cancer chemoprevention. Cancer Epidemiol Biomarkers Prev., 15, 1526-1531 (2006). (Pubitemid 44299327)
34. Maeba, R., Hara, H., Ishikawa H., Hayashi, S., Yoshimura, N., Kusano, J., Takeoka, Y., Yasuda, D., Okazaki, T., Kinoshita, M. and Teramoto, T., myo-Inositol treatment increases serum plasmalogens and decreases small dense LDL, particularly in hyperlipidemic subjects with metabolic syndrome. J. Nutr. Sci. Vitaminol., 54, 196-202 (2008). (Pubitemid 352008302)
35. Benjamin, J., Levine, J., Fux, M., Aviv, A., Levy, D. and Belmaker, R. H., Double-blind, placebo-controlled, crossover trial of inositol treatment for panic disorder. Am. J. Psychiatry, 152, 1084-1086 (1995).
36. Palatnik, A., Frolov, K., Fux, M. and Benjamin, J., Double-blind, controlled, crossover trial of inositol versus fluvoxamine for the treatment of panic disorder. J. Clin. Phychopharmacol., 21(3), 335-339 (2001). (Pubitemid 32452940)
37. Fux, M., Levine, J., Aviv, A. and Belmaker, R. H., Inositol treatment of obsessive-compulsive disorder. Am. J. Psychiatry, 153, 1219-1221 (1996). (Pubitemid 26299846)
38. Levine, J., Barak, Y., Gonzalves, M., Szor, H., Elizur, A., Kofman, O. and Belmaker, R. H., Double-blind, controlled trial of inositol treatment of depression. Am. J. Psychiatry, 152, 792-794 (1995).
39. Levine, J., Barak, Y., Kofman, O. and Belmaker, R H., Follow-up and relapse analysis of an inositol study of depression. Isr. J. Psychiatry Relat. Sci., 32, 14-21 (1995).
40. Adams, R. and Bockstahler, T. E., Preparation and reactions of o-hydroxycinnamic acids and esters. J. Am. Chem. Soc., 74, 5346-5348 (1952).
41. Johnson, J. R., In "Organic reactions", John Wiley & Sons, Inc.: New York, 1942; Vol. 1, Chapter 8, pp. 250-251.
42. Heck, R. F. and Nolley, J. P. Jr., Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styrylhalides. J. Org. Chem., 37, 2320-2322 (1972).
43. Heck, R. F., Palladium-catalyzed vinylation of organic halides. Org. React. 27, 345-390 (1982).
44. Fujimaki, M., Tsugita, T. and Kurata, T., Fractionation and identification of volatile acids and phenols in the steam distillate of rice bran. Agric. Biol. Chem., 41, 1721-1725 (1977). (Pubitemid 8219510)
45. Smart, M. G. and O'Brien, T. P., Observations on the scutellum. III. Ferulic acid as a component of the cell wall in wheat and barley. Aust. J. Plant Physiol., 6, 485-491 (1971).
46. Fulche, R. G., O'Brien, T. P. and Lee, J. W., Studies on the aleurone layer I. Oonventional and fluorescence microscopy of the cell wall with emphasis on phenol-carbohydrate complexes in wheat. Aust. J. Biol. Sci., 25, 23-34 (1972).
47. Pussayanawin, V., Wetzel, D. L. and Fulcheeer, R. G., Fluorescence detection and measurement of ferulic acid in wheat milling fractions by microscopy and HPLC. J. Agric. Food Chem., 36(3), 515-520 (1988).
48. Wetzel, D. L., Pussayawin, V. and Fulcher, R. G., Determination of ferulic acid in grain by HPLC and microspectro-fluorimetry. Dev. Food Sci., 17, 409-426 (1988).
49. Pussayanawin, V. and Wetzel D. L, High-performance liquid chromatographic determination of ferulic acid in wheat milling fractions as a measure of bran contamination. J. Chromatogr., 391, 243-255 (1987).
50. Cherney, D. J. R., Patterson, J. A., Cherney, J. H. and Axtell, J. D., Fibre and soluble phenolic monomer composition of morphological components of sorghum stover. J. Sci. Food Agric., 54, 645-649 (1991).
51. Ishii, T. and Tobita, T., Structural characterization of feruloyl oligosaccharides from spinach-leaf cell walls. Carbohydr. Res., 248, 179-190 (1993). (Pubitemid 23302976)
52. Fry, S. C., Phenolic components of the primary cell wall. Feruloylated disaccharides of D-galactose and L-arabinose from spinach polysaccharide. Biochem. J., 203, 493-504 (1982).
53. Terao, J., Karasawa, H., Arai, H., Nagao, A., Suzuki, T. and Takama, K., Peroxyl radical scavenging activity of caffeic acid and its related phenolic compounds in solution. Biosci. Biotechnol. Biochem., 57, 1204-1205 (1993).
54. Marinova, E. M. and Yanishlieva, N. V., Effect of temperature on the antioxidative action of inhibitors in lipid autoxidation. J. Sci. Food Agric, 60, 313-318 (1992).
55. Kahnt, G, Trans-cis-equilibrium of hydroxycinnamic acids during irradiation of aqueous solutions at different pH. Phytochem., 6, 755-758 (1967).
56. You, Y., Park, J., Yoon, H. G., Lee, Y. H., Hwang, K., Lee, J., Kim, K., Lee, K. W., Shim S. and Jun, W., Stimulatory effects of ferulic acid on endurance exercise capacity in mice. Biosci. Biotechnol. Biochem., 73, 1392-1397 (2009).
57. Hatfield, R. D., Helm, R. F and Ralph, J., Synthesis of methyl 5-O-trans-feruloyl-a-L-arabinofuranoside and its use as a substrate to assess feruloyl esterase activity. Anal. Biochem., 194, 25-33 (1991).
58. Yoshida, Y., Kimura, Y. and Adachi, S., Thermal inactivation of immobilized lipase in 1-alcohols. J. Biosci. Bioeng, 102, 66-68 (2006). (Pubitemid 44354444)
59. Kawamura, Y., Nakanishi, K. and Matsuno, R., Stability of immobilized α-chymotrypsin. Biotechnol. Bioeng, 23, 488-490 (1981).
60. Yoshida, Y., Kimura, Y., Kadota, M., Tsuno, T. and Adachi, S., Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature. Biotechnol. Lett, 28, 1471-1474 (2006). (Pubitemid 44367009)
61. Matsuo, T., Kobayashi, T., Kimura, T., Hosoda, A., Taniguchi, H. and Adachi, S., Continuous synthesis of glyceryl ferulate using immobilized Candida antarctica lipase. J. Oleo Sci., 57, 375-380 (2008).
62. Kobayashi, T., Matsuo, T., Kimura, Y. and Adachi, S., Thermal stability of immobilized lipase from Candida antarctica in glycerols with various water contents at elevated temperatures. J. Am. Oil Chem. Soc., 85, 1041-1044 (2008).
63. Tsuchiyama, M., Sakamoto, T., Fujita, T., Murata, S. and Kawasaki, H., Esterification of ferulic acid with polyols using a ferulic acid esterase from Aspergillus niger. Biochim. Biophys. Acta - Gen. Subj., 1760, 1071-1079 (2006). (Pubitemid 43867930)
64. Matsuo, T., Kobayashi, T., Kimura, Y., Tsuchiyama, M., Oh, T., Sakamoto, T. and Adachi, S., Synthesis of glyceryl ferulate by immobilized ferulic acid esterase. Biotechnol. Lett, 30, 2151-2156 (2008).
65. Fang, X., Shima, M., Kadata, M., Tsuno, T. and Adachi, S., Suppressive effect of alkyl ferulate on the oxidation of linoleic acid. Biosci. Biotechnol. Biochem., 70, 457-461 (2006). (Pubitemid 43289428)
66. Fang, X., Kikuchi, S., Shima, M., Kadata, M., Tsuno, T. and Adachi, S., Suppressive effect of alkyl ferulate on the oxidation of microencapsulated linoleic acid. Eur. J. Lipid Sci. Technol., 108, 97-102 (2006).
67. Terada, Y., Kometani, T., Nishimura, T., Takii, H. and Okada, S., Prevention of hesperidin crystal formation in canned mandarin orange syrup and clarified orange juice by hesperidin glycosides. Food Sci. Technol. Int., 1, 29-33 (1995).
68. Kometani, T., Nishimura, T., Nakae, T., Takii, H. and Okada, S., A method for preparation of soluble carthamin, red pigment from aafflower, using glycosyl hesperidin. Food Sci. Technol. Res., 5, 265-270 (1999). (Pubitemid 129607591)
69. Kim, M., Kometani, T., Okada, S., Shimizu, M., Permiation of hesperidin glycosides across Caco-2cell monolayers via the paracellular pathway. Biosci. Biotechnol Biochem., 63, 2183-2188 (1999). (Pubitemid 129549043)
70. Nakae, T., Kometani, T., Nishimura, T., Takii, H. and Okada, S., Preparation of glyceroglycolipids from pumpkin and their effects on polymorphic transformation of cocoa butter. Food Sci. Technol. Res., 5, 263-268 (2000).
71. Nakae, T., Kometani, T., Nishimura, T., Takii, H. and Okada, S., Effect of glycolipid fraction on fat bloom in dark and milk chocolates. Food Sci. Technol. Res., 5, 269-274 (2000).
72. Nakae, T., Kometani, T., Nishimura, T., Takii, H. and Okada, S., Effects of glyceroglycolipids prepared from various natural materials on polymorphic transformation of cocoa butter. Food Sci. Technol. Res., 5, 320-323 (2000).
73. Kometani, T., Terada Y., Nishimura, T., Takii, H. and Okada, S., Transglycosylation to hesperidin by cyclodextrin glucanotransferase from an alkalophilic Bacillus species in alkaline pH and properties of hesperidin glycosides. Biosci. Biotechnol. Biochem., 58, 1990-1994 (1994).
74. Zhao, Z., Egashira, Y. and Sanada H., Ferulic acid sugar esters are recovered in rat plasma and urine mainly as the sulfoglucuronide of ferulic acid. J. Nutr., 133, 1355-1361 (2003). (Pubitemid 36548706)
75. Gupta, S., Sukhija P. S. and Bhatia I. S., Role of phenolics and phospholipids as antioxidants for ghee. Milchwissenschaf, 34, 205-206 (1979).
76. Mori, H., Kawabata K, Yoshimi, N, Tanaka, T, Murakami, T., Okada, T. and Murai, H., Chemopreventive effects of ferulic acid on oral and rice germ on large bowel carcinogenesis. Anticancer Res., 19, 3775-3778 (1999).
77. Hudson, E. A., Dinh, P. A., Kokubun, T., Simmonds, M. S. and Gescher, A. C., Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells. Cancer Epidemiol Biomarkers Prev., 9, 1163-1170 (2000).
78. Jung, E. H., Kim, S. R., Hwang, I. K. and Ha, T. Y., Hypoglycemic effects of a phenolic acid fraction of rice bran and ferulic acid in C57BL/KsJ-db/db mice. J. Agric. Food Chem., 55, 9800-9804 (2007).
79. Ardiansyah, Ohsaki, Y., Shirakawa, H, Koseki, T. and Komai, M., Novel effects of a single administration of ferulic acid on the regulation of blood pressure and the hepatic lipid metabolic profile in stroke-prone spontaneously hypertensive. J. Agric. Food Chem., 56, 2825-2830 (2008). (Pubitemid 351685231)
80. Jin, Y., Yan, E. Z., Fan, Y., Zong, Z. H, Qi, Z. M. and Li, Z., Sodium ferulate prevents amyloid-beta-induced neurotoxicity through suppression of p38 MAPK and upregulation of ERK-1/2 and Akt/protein kinase B in rat hippocampus. Acta Pharmacol. Sin., 26, 943-951 (2005). (Pubitemid 41153214)
81. Yan, J. J., Cho, J. Y., Kim, H. S., Kim, K. L., Jung, S., Huh, S. O., Suh, H. W., Kim, Y. H. and Song, D. K., Protection against beta-amyloid peptide toxicity in vivo with long-term administration of ferulic acid. Br. J. Pharmacol, 133, 89-96 (2001).
82. Wiboonsirikul, J., Kimura, Y., Kadota, M., Morita, H., Tsuno, T. and Adachi, S., Properties of extracts from defatted rice bran by its subcritical water treatment. J. Agric. Food Chem., 55, 8759-8765 (2007). (Pubitemid 350013124)
83. Hata, S., Wiboonsirikul, J., Maeda A., Kimura Y. and Adachi, S., Extraction of defatted rice bran by subcritical water treatment. Biochem. Eng J., 40, 44-53 (2008).
84. Wiboonsirikul, J., Kimura, Y., Kanaya Y., Tsuno, T. and Adachi, S., Production and characterization of functional substances from a by-product of rice bran oil and protein production by a compressed hot water treatment. Biosci. Biotechnol. Biochem., 72, 384-392 (2008). (Pubitemid 351353672)
85. Wiboonsirikul, J., Hata, S., Kimura, Y., Tsuno, T. and Adachi, S., Production of functional substances from black rice bran by its treatment in subcritical water. LWT-Food Sci. Technol, 40, 1732-1740 (2007). (Pubitemid 47058514)
86. Wiboonsirikul, J., Khuwijitjaru, P., Kimura Y., Morita, H., Tsuno, T. and Adachi, S., Production optimization of the extract with high phenolic content and radical scavenging activity from defatted rice bran by subcritical water treatment Jpn. J. Food. Eng., 8, 311-315 (2007).
87. Wiboonsirikul, J., Sakai, Y., Hosoda A., Morita, H., Kimura, Y, Taniguchi, H, Tsuno, T. and Adachi, S., Mutagenicity of the extract from defatted rice bran by subcritical water treatment. Jpn. J. Food Eng., 9, 75-78 (2008).
88. Khuwijitjaru, P., Nualchan, P. and Adachi, S., Foaming and emulsifying properties of rice bran extracts obtained by subcritical water treatment. Silpakorn U. Sci. Technol. J., 1, 7-12 (2007).
89. Jeyashoke, N., Chiou, T.-Y, Neoh, T. L., Murayama Y., Kobayashi, T. and Adachi, S., Effect of temperature-rising rate on the antioxidative ability of the defatted rice bran extract obtained by subcritical water treatment. Food Sci. Technol. Res., 16, 197-200 (2010).
90. Murayama, Y., Neoh, T. L., Kobayashi, T. and Adachi, S., Production of emulsifying and antioxidative substances from defatted rice bran by two-step subcritical water treatment Jpn. J. Food Eng., 10, 107-114 (2009).
91. Wiboonsirikul, J., Nakazawa R., Kobayashi, T., Morita H., Tsuno, T. and Adachi, S., Suppression of the oxidation of methyl linoleate encapsulated with the extract from defatted rice bran by a compressed hot water treatment. Eur. Food Res. Technol, 228, 109-114 (2008).
92. Habeych, E., van der Goot, A. J., Boom, R and Adachi, S., Compatibilization of starch-zein blends under shear flow. Abstract of 5th International Symposium on Food Rheology and Structure, Zurich (2009).