Triterpene alcohol and sterol ferulates from rice bran and their anti- inflammatory effects

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 6, 2000, Pages 2313-2319

  Akihisa, Toshihiro ^a   Yasukawa, Ken ^a   Yamaura, Miho ^a   Ukiya, Motohiko ^a   Kimura, Yumiko ^a   Shimizu, Naoto ^b   Arai, Koichi ^c  

^a NIHON UNIVERSITY   (Japan)

^b YOKOGAWA ANALYTICAL SYSTEMS INC   (Japan)

^c MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

Author keywords

Antiedema; Rice bran; Sterol; TPA induced ear edema; Trans and cis feruloyl esters; Triterpene alcohol

Indexed keywords

ALCOHOL DERIVATIVE; ANTIINFLAMMATORY AGENT; COUMARIC ACID; FERULIC ACID; PHORBOL 13 ACETATE 12 MYRISTATE; STEROL; TRITERPENE;

ANIMAL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BRAN; CHEMISTRY; CRYSTALLIZATION; DERIVATIZATION; EDEMA; EXTRACTION; FEMALE; IATROGENIC DISEASE; ISOLATION AND PURIFICATION; MOUSE; MOUSE STRAIN; PROMOTER REGION; RICE; STRUCTURE ACTIVITY RELATION;

ALCOHOLS; ANIMALS; ANTI-INFLAMMATORY AGENTS; COUMARIC ACIDS; EDEMA; FEMALE; MICE; MICE, INBRED ICR; ORYZA SATIVA; STEROLS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRADECANOYLPHORBOL ACETATE; TRITERPENES;

EID: 0033946944     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf000135o     Document Type: Article

References (30)

1. Akihisa, T.; Yasukawa, K.; Kasahara, Y. Triterpenoids from the flowers of Compositae and their anti-inflammatory effects. Curr. Topics Phytochem. 1997, 1, 137-144.
2. Arín, M. J.; Díez, M. T.; Resines, J. A. High-performance liquid chromatographic determination of phenolic acids isolated from plants. J. Liq. Chromatogr. 1995, 18, 4183-4192.
3. Diack, M.; Saska, M. Separation of vitamin E and γ-oryzanols from rice bran by normal-phase chromatography. J. Am. Oil Chem. Soc. 1994, 71, 1211-1217.
4. Endo, T.; Ueno, K.; Inaba, Y. Studies on the ferulates contained in rice bran oil. I. Analysis of the ferulates by means of GLC and TLC. J. Jpn. Oil Chem. Soc. 1968, 17, 344-348.
5. 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.
6. Goad, L. J.; Akihisa, T. Analysis of Sterols; Blackie Academic and Professional: London, 1997.
7. 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.
8. Kahlon, T. S.; Saunders: R. M.; Sayre, R. N.; Chow, F. I.; Chiu, M. M.; Betschart, A. A. Cholesterol-lowering effects of rice bran and rice bran oil fractions in hypercholesterolemic hamsters. Cereal Chem. 1992, 69, 485-489.
9. Kahlon, T. S.; Chow, F. I.; Sayre, R. N. Cholesterol-lowering properties of rice bran. Cereal Foods World 1994, 39, 99-103.
10. Kawanishi, K.; Hashimoto, Y. Long chain esters of Virola species. Phytochemistry 1982, 26, 749-752.
11. Kokpol, U.; Chavasiri, W. Taraxeryl cis-p-hydroxycinnamate, a novel taraxeryl from Rhizophora apiculata. J. Nat. Prod. 1990, 53, 953-955.
12. Kondo, Y.; Nakajima, K.; Nozoe, S.; Suzuki, S. Isolation of ovulatory-active substances from crops of Job's Tears (Coix lacryma-jobi L. var. ma-yuen Stapf). Chem. Pharm. Bull. 1988, 36, 3147-3152.
13. Norton, R. A. Quantitation of steryl ferulate and p-coumarate esters from corn and rice. Lipids 1995, 30, 269-274.
14. Otsuka, H.; Kashima, N.; Nakamoto, K. A neolignan glycoside and acylated iridoid glucosides from stem bark of Alangium platanifolium. Phytochemistry 1996, 42, 1435-1438.
15. Rogers E. J.; Rice, S. M.; Nicolosi, R. J.; Carpenter, D. R.; McClelland, C. A.; Romanczyk, L. J., Jr. Identification and quantitation of γ-oryzanol components and simultaneous assessment of tocols in rice bran oil. J. Am. Oil Chem. Soc. 1993, 70, 301-307.
16. Seetharamaiah, G. S.; Chandrasekhara, N. Effect of oryzanol on fructose induced hypertriglyceridaemia in rats. Indian J. Med. Res. 1988, 88, 278-281.
17. 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.
18. Shinomiya, M.; Morisaki, N.; Matsuoka, N.; Izumi, S.; Saito, Y.; Kumagai, A.; Mitani, K.; Morita, S. Effects of γ-oryzanol on lipid metabolism in rats fed high-cholesterol diet. Tohoku J. Exp. Med. 1983, 141, 191-197.
19. Sugano, M.; Tsuji, E. Rice bran oil and human health. Biomed. Environm. Sci. 1996, 9, 242-246.
20. Sugano, M.; Tsuji, E. Rice bran oil and cholesterol metabolism. Am. Soc. Nutr. Sci. 1997, 17, 521S-524S.
21. Sugano, M.; Koba, K.; Tsuji, E. Health benefits of rice bran oil. Anticancer Res. 1999, 19, 3651-3658.
22. Tamura, T.; Sakaedani, N.; Matsumoto, T. Isolation of dihydro-β-sitosteryl ferulate from corngerm oil. Nippon Kagaku Zasshi 1958, 79, 1011-1014.
23. Tamura, T.; Takeda, M.; Murakami, K.; Yoshida, A.; Matsumoto, T. On some ferulates. J. Jpn. Oil Chem. Soc. 1962, 11, 454-458.
24. Tanaka, A. Separation and quantitative analysis of ferulates in rice bran oil by thin-layer chromatography. J. Jpn. Oil Chem. Soc. 1971, 20, 792-797.
25. Tanaka, A.; Kato, A. Mass spectra of several ferulates. J. Jpn. Oil Chem. Soc. 1975, 24, 570-574.
26. Van Boven, M.; Daenens, P.; Tytgat, J.; Cokelaere, M. Determination of simmondsins and simmondsin ferulates in jojoba meal and feed by high-performance liquid chromatography. J. Agric. Food Chem. 1996, 44, 2239-2243.
27. Yasukawa, K.; Takido, M.; Matsumoto, T.; Takeuchi, M., Nakagawa, S. Sterol and triterpene derivatives from plants inhibit the effects of a tumor promoter, and sitosterol and betulinic acid inhibit tumor formation in mouse skin two-stage carcinogenesis. Oncology 1991, 48, 72-76.
28. Yasukawa, K.; Akihisa, T. Anti-inflammatory and antitumorpromoting activities of sterols, triterpene alcohols and their derivatives. Recent Res. Devel. Oil Chem. 1997, 1, 115-125.
29. Yasukawa, K.; Akihisa, T.; Kimura, Y.; Tamura, T.; Takido, M. Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in two-stage carcinogenesis in mouse skin. Biol. Pharm. Bull. 1998, 21, 1072-1076.
30. Yoshino, G.; Kazumi, T.; Amano, M.; Tateiwa, M.; Yamasaki, T.; Takashima, S.; Iwai, M.; Hatanaka, H.; Baba, S. Effects on gamma-oryzanol on hyperlipidemic subjects. Curr. Therap. Res. 1989, 45, 543-552.