Advertisement

Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat bran

  • Seong Su Hong
  • Joa Sub Oh
Original Article Bioactive Materials

Abstract

Chromatographic separation of ethanol extract of wheat bran led to the isolation of five 5-alk(en)ylresorcinols, four aliphatic compounds, and one phenolic glycoside. These were, respectively: 5-n-heptadecylresorcinol (1), 5-n-14′-(Z)-heneicosylresorcinol (2), 5-n-nonadecylresorcinol (3), 5-n-heneicosylresorcinol (4), 5-n-tricosylresorcinol (5), 1-O-(9Z,12Z,15Z-octadecatrienoate) glycerol (6), 2-linoleoylglycerol (7), 1-O-(9Z,12Z-octadecatrienoate)glycerol (8), pinellic acid (9), and tachioside (10). Their structures were determined by 1D- & 2D-NMR and mass spectroscopy data analysis. The inhibitory effects of isolated constituents on the release of β-hexosaminidase from RBL-2H3 cells were examined. Inhibition was shown by 5-n-nonadecylresorcinol (3), 5-n-heneicosylresorcinol (4), pinellic acid (9), and tachioside (10).

Keywords

5-alk(en)ylresorcinol β-hexosaminidase RBL-2H3 cells wheat bran 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ahn NH, Ripperger H, Schmidt J, Porzel A, Sung TV, and Adam G (1996) Resorcinol derivatives from two Ardisia species. Planta Med 62, 479–480.CrossRefGoogle Scholar
  2. Baublis AJ, Clydesdale FM, and Decker EA (2000) Antioxidants in wheatbased breakfast cereals. Cereal Food World 45, 71–74.Google Scholar
  3. Brindzova L, Zalibera M, Jakubik T, Mikulasova M, Takacsova M, Mosovska S, and Rapta R (2009) Antimutagenic and Radical Scavenging Activity of Wheat Bran. Cereal Res Commun 37, 45–55.CrossRefGoogle Scholar
  4. Chang J and Inui T (2005) Novel phenolic glycoside dimer and trimer from the whole herb of Pyrola rotundifolia. Chem Pharm Bull 53, 1051–1053.CrossRefGoogle Scholar
  5. Choi SJ, Min YD, Lee SO, Yang CM, Nam JH, Lee KH, Jang KU, Lee JH, and Lee KR (2004) Phytochemical constituents of Saussurea nutans Nakai. Korean J Pharmacogn 35, 35–40.Google Scholar
  6. Choi SP, Kang MY, and Nam SH (2005) Inhibitory Activity of Pigmented Rice Bran Extract to the Allergic Inflammation in Basophilic Cell Line and Peritoneal Mast Cells. J Korean Soc Appl Biol Chem 48, 315–321.Google Scholar
  7. Čukelj N, Jakasa I, Sarajlija H, Novotni D, and Duška Ćurić (2011) Identification and quantification of lignans in wheat bran by gas chromatography-electron capture detection. Talanta 84, 127–132.CrossRefGoogle Scholar
  8. Huang H, Tong X, Deng H, Fu L, and Zhang R (2008) Inhibition of the antigen-induced activation of RBL-2H3 cells by gab2 siRNA. Cell Mol Immunol 5, 433–438.CrossRefGoogle Scholar
  9. Inoshiri S, Sasaki M, Kohda H, Otsuka H, and Yamasaki K (1987) Aromatic glycosides from Berchemia racemosa. Phytochemistry 26, 2811–2814.CrossRefGoogle Scholar
  10. Iwatsuki K, Akihisa T, Tokuda H, Ukiya M, Higashihara H, Mukainaka T, Iizuka M, Hayashi Y, Kimura Y, and 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.CrossRefGoogle Scholar
  11. Jung CM, Kwon HC, Choi SJ, Lee JH, Lee DJ, Ryu SN, and Lee KR (2000) Phytochemical constituents of Ainsliaea acerifolia. Korean J Pharmacogn 31, 125–129.Google Scholar
  12. Kim JS, Shim SH, Xu YN, Kang SS, Son KH, Chang HW, Kim HP, and Bae K (2004) Phenolic Glycosides from Pyrola japonica. Chem Pharm Bull 52, 714–717.CrossRefGoogle Scholar
  13. Kim JS, Yean, MH, Seo HK, Lee JH, and Kang SS (2009) Phytochemical studies on Lonicera caulis (2) — aliphatic and phenolic compounds. Korean J Pharmacogn 40, 326–333.Google Scholar
  14. Lee E, Choi EJ, Cheong H, Kim YR, Ryu SY, and Kim KM (1999) Antiallergic actions of the leaves of Castanea crenata and isolation of an active component responsible for the inhibition of mast cell degranulation. Arch Pharm Res 22, 320–323.CrossRefGoogle Scholar
  15. Maes C and Delcour JA (2002) Structural characterization of water-extractable and water-unextractable arabinoxylans in wheat bran. J Cereal Sci 35, 315–326.CrossRefGoogle Scholar
  16. Marone G, Galli SJ, and Kitamura Y (2002) Probing the roles of mast cells and basophils in natural and acquired immunity, physiology and disease. Trends Immunol 23, 425–427.CrossRefGoogle Scholar
  17. Marquardt DL and Wasserman SI (1983) Modulation of rat serosal mast cell biochemistry by in vivo dexamethasone administration. J Immunol 131, 934–939.Google Scholar
  18. Morikawa T, Xu F, Matsuda H, and Yoshikawa M (2010) Structures of novel norstilbene dimer, longusone A, and three new stilbene dimers, longusols A, B, and C, with antiallergic and radical scavenging activities from Egyptian natural medicine Cyperus longus. Chem Pharm Bull 58, 1379–1385.CrossRefGoogle Scholar
  19. Qu H, Madl RL, Takemoto DJ, Baybutt RC, and Wang W (2005) Lignans are involved in the antitumor activity of wheat bran in colon cancer SW480 cells. Nutr Cancer 135, 598–602.Google Scholar
  20. Reddy BS, Hirose Y, Cohen LA, Simi B, Cooma I, and Rao CV (2000) Preventive potential of wheat bran fractions against experimental colon carcinogenesis: implications for human colon cancer prevention. Cancer Res 60, 4792–4797.Google Scholar
  21. Schwartz LB, Lewis RA, Seldin D, and Austen KF (1981) Acid hydrolases and tryptase from secretory granules of dispersed human lung mast cells. J Immunol 126, 1290–1294.Google Scholar
  22. Suzuki Y, Esumi Y, Uramoto M, Kono Y, and Sakurai A (1997) Structural analyses of carbon chains in 5-alk(en)ylresorcinols of rye and wheat whole flour by tandom mass spectrometry. Biosci Biotech Biochem 61, 480–486.CrossRefGoogle Scholar
  23. Swaroop A, Sinha AK, Chawla R, Arora R, Sharma RK, and Kumar JK (2005) Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol: A novel triglyceride from berries of Hippophae rhamnoides. Chem Pharm Bull 53, 1021–1024.CrossRefGoogle Scholar
  24. Wang J, Sun B, Cao Y, and Tian Y (2009) Protein glycation inhibitory activity of wheat bran feruloyl oligosaccharides. Food Chemistry 112, 350–353.CrossRefGoogle Scholar
  25. Wang Q, Yuan D, Matsuda H, and Yoshikawa M (2007) Inhibitory effects of Rheum officinale and anthraquinone aglycones on antigen-induced degranulation in RBL-2H3 cells. Asian J Trad Med 2, 189–197.Google Scholar
  26. Yuan X, Wang J, and Yao H (2005) Antioxidant activity of feruloylated oligosaccharides from wheat bran. Food Chemistry 90, 759–764.CrossRefGoogle Scholar

Copyright information

© The Korean Society for Applied Biological Chemistry 2012

Authors and Affiliations

  1. 1.Natural Products Research InstituteGyeonggi Institute of Science & Technology PromotionSuwonRepublic of Korea
  2. 2.College of PharmacyDankook UniversityCheonanRepublic of Korea

Personalised recommendations