Sterol Ferulates, Sterols, and 5-Alk(en)ylresorcinols from Wheat, Rye, and Corn Bran Oils and Their Inhibitory Effects on Epstein-Barr Virus Activation

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 23, 2003, Pages 6683-6688

  Iwatsuki, Kenji ^a   Akihisa, Toshihiro ^b   Tokuda, Harukuni ^c   Ukiya, Motohiko ^b   Higashihara, Hiroshi ^c   Mukainaka, Teruo ^c   Iizuka, Masao ^b   Hayashi, Yoshiharu ^a   Kimura, Yumiko ^b   Nishino, Hoyoku ^c  

^a K Lab for Intell Med Remote Serv   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

Author keywords

5 alk(en)ylresorcinol; Antitumor promoter; Corn bran; Epstein Barr virus early antigen; Rye bran; Sterol; Sterol ferulate; Wheat bran

Indexed keywords

2 METHYLLATHOSTEROL FERULATE; 24 METHYLCHOLESTANOL FERULATE; 24 METHYLCHOLESTEROL; 24 METHYLCHOLESTEROL FERULATE; 24 METHYLENECHOLESTANOL FERULATE; 5 HENICOSYLRESORCINOL; 5 N (14' NONADECENYL)RESORCINOL; 5 N (2' OXO 14' HENEICOSENYL)RESORCINOL; 5 N (2' OXOHENEICOSYL)RESORCINOL; 5 N HEPTADECYLRESORCINOL; 5 N PENTACOSYLRESORCINOL; 5 N TRICOSYLRESORCINOL; 5 NONADECYLRESORCINOL; CORN BRAN OIL; EARLY ANTIGEN; RESORCINOL DERIVATIVE; RYE BRAN OIL; SCHOTTENOL; SCHOTTENOL FERULATE; SITOSTANOL; SITOSTEROL; SITOSTEROL FERULATE; STEROL; STEROL DERIVATIVE; STEROL FERULATE; STIGMASTANOL FERULATE; STIGMASTEROL; UNCLASSIFIED DRUG; UNINDEXED DRUG; VEGETABLE OIL; WHEAT OIL;

ARTICLE; CORN; CRYSTALLIZATION; DRUG ISOLATION; EPSTEIN BARR VIRUS; LIPID ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; RYE; VIRUS ACTIVATION; VIRUS INHIBITION; WHEAT BRAN;

CEREALS; COUMARIC ACIDS; HERPESVIRUS 4, HUMAN; PHYTOSTEROLS; PLANT OILS; RESORCINOLS; SECALE CEREALE; TRITICUM; VIRUS ACTIVATION; ZEA MAYS;

HUMAN HERPESVIRUS 4; SECALE CEREALE; TRITICUM AESTIVUM; ZEA MAYS;

EID: 0242362642     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf030371+     Document Type: Article

References (23)

1. Akihisa, T.; Yasukawa, K. Antitumor-promoting and anti-inflammatory activities of triterpenoids and sterols from plants and fungi. In Studies in Natural Products Chemistry, Vol. 25, Bioactive Natural Products (Part F); Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, The Netherlands, 2001; pp 43-87.
2. Akihisa, T.; Yasukawa, K.; Yamaura, M.; Ukiya, M.; Kimura, Y.; Shimizu, N.; Arai, K. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects. J. Agric. Food Chem. 2000, 48, 2313-2319.
3. 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, 1072-1078.
4. Goad, L. J.; Akihisa, T. Analysis of Sterols; Blackie Academic and Professional: London, U.K., 1997.
5. Cirigottis, K. A.; Cleaver, L.; Corrie, J. E. T.; Grasby, R. G.; Green, G. H.; Mock, J.; Nimgirawath, S.; Read, R. W.; Ritchie, E.; Taylor, W. C.; Vadasz, A.; Webb, W. R. G. Chemical studies of the Proteceae. VII. An examination of the woods of 17 species for 5-alk(en)ylresorcinol derivatives. Aust. J. Chem. 1974, 27, 345-355.
6. Suzuki, Y.; Esumi, Y.; Uramoto, M.; Kono, Y.; Sakurai, A. Structural analyses of carbon chains in 5-alk(en)ylresorcinols of rye and wheat whole flour by tandem mass spectrometry. Biosci., Biotechnol., Biochem. 1997, 61, 480-486.
7. Seitz, L. M. Identification of 5-(2-oxoalkyl)resorcinols and 5-(2-oxoalkenyl)resorcinols in wheat and rye grains. J. Agric. Food Chem. 1992, 40, 1541-1546.
8. Shibahara, A.; Yamamoto, K.; Nakayama, T.; Kajimoto, G. Rapid determination of double bond position in monounsaturated fatty acids by GC-MS and its application to fatty acid analysis. J. Jpn. Oil Chem. Soc. 1985, 34, 618-625.
9. Takaishi, Y.; Ujita, K.; Tokuda, H.; Nishino, H.; Iwashima, A.; Fujita, T. Inhibitory effects of dihydroagarofuran sesquiterpenes on Epstein-Barr virus activation. Cancer Lett. 1992, 65, 19-26.
10. 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.
11. Hakala, P.; Lampi, A.-M.; Ollilainen, V.; Werner, U.; Murkovic, M.; Wähälä, K.; Karkola, S.; Phronen, V. Steryl phenolic acid esters in cereals and their milling fractions. J. Agric. Food Chem. 2002, 50, 5300-5307.
12. Norton, R. A. Isolation and identification of steryl cinnamic acid derivatives from corn bran. Cereal Chem. 1994, 71, 111-117.
13. Norton, R. A. Quantitation of steryl ferulate and p-coumarate esters from corn and rice. Lipids 1995, 30, 269-274.
14. Moreau, R. A.; Singh, V.; Eckhoff, S. R.; Powell, M. J.; Hicks, K. B.; Norton, R. A. Cereal Chem. 1999, 76, 449-451.
15. Verdeal, K.; Lorenz, K. Alkylresorcinols in wheat, rye, and triticale. Cereal Chem. 1977, 54, 475-483.
16. Gohil, S.; Pettersson, D.; Salomonsson, A.-C.; Åman, P. Analysis of alkyl- and alkenylresorcinols in triticale, wheat and rye. J. Sci. Food Agric. 1988, 45, 43-52.
17. Kozubek, A. Isolation of 5-n-alkyl, 5-n-alkyl- and 5-n-alkdienyl-resorcinol homologs from rye grains. Acta Aliment. Pol. 1985, 9, 185-198.
18. Kozubek, A.; Tyman, J. H. P. Cereal grain 5-alk(en)ylresorcinolic lipids: mono and dienoic homologues are present in rye grains. Chem. Phys. Lipids 1995, 78, 29-35.
19. Murakami, A.; Ohigashi, H.; Koshimizu, K. Anti-tumor promotion with food phytochemicals: A strategy for cancer chemoprevention. Biosci., Biotechnol., Biochem. 1999, 60, 1-8.
20. Awad, A. B.; Fink, C. S. Phytosterols as anticancer dietary components: evidence and mechanism of action. J. Nutr. 2000, 130, 2127-2130.
21. Raicht, R. F.; Cohen, B. I.; Fazzini, E.; Sarwal, A.; Takahashi, M. Protective effect of plant sterols against chemically-induced colon tumor in rats. J. Cancer Res. 1980, 40, 403-405.
22. Awad, A. B.; Gan, Y.; Fink, C. S. Effect of β-sitosterol, a plant sterol, on growth, protein phosphatase 2A and phospholipids D in LNCaP cells. Nutr. Cancer 2000, 36, 74-78.
23. Awad, A. B.; Down, A. C.; Fink, C. S. Inhibition of growth and stimulation of apoptosis by β-sitosterol treatment of MDA-MB-231 human breast cancer cells in culture. Int. J. Mol. Med. 2000, 5, 541-546.