Isolation of 5-(Hydroxymethyl)Furfural from Lycium chinense and its Inhibitory Effect on the Chemical Mediator Release by Basophilic Cells

Abstract

The effect of hot water extracts of Lycium chinense fruits (LCF) on the β-hexosaminidase (β-hexo) release by IgE sensitized BSA stimulated rat basophilic leukemia (RBL-2H3) cells was investigated. The ethylacetate (EtOAc) layer of the extract has shown an inhibitory effect on β-hexo release from RBL-2H3 cells at the antigen antibody binding stage. The water (H₂O) fraction (EFW) of the chloroform (CHCl₃) extract from the EtOAc layer also inhibited β-hexo release at the same stage in a dose-dependent manner. With column chromatography preparation, proton and carbon nuclear magnetic resonance (¹H and ¹³C NMR) spectra, electron ionization mass spectrometer (EI‐MS) spectra, and high-performance liquid chromatography (HPLC) analysis, the active component was determined to be 5-(hydroxymethyl)furfural (5-HMF). Thus, the 5-HMF showed an inhibitory effect on β-hexo release at the antigen-antibody binding stage and the antibody-receptor binding stage. Furthermore, 5-HMF suppressed [Ca²⁺]i influx in the IgE-sensitized BSA-stimulated RBL-2H3 cells. Our results show that 5-HMF may be useful for the treatment or prevention of type I allergic diseases.

Key words

anti‐allergic - basophile - β‐hexosaminidase - 5‐(hydroxymethyl)furfural - Lycium chinense - Solanaceae - RBL‐2H3

References

• 1 Harrison L F. Landscape plants for eastern North America, 2nd edition. New York; John Wiley & Sons, Inc. 1997
• 2 Pottérat O. Goji (Lycium barbarum and L. chinense): phytochemistry, pharmacology and safety in the perspective of traditional uses and recent popularity.  Planta Med. 2010;  76 7-19
• 3 Li Q Y. Healthy functions and medicinal prescriptions of Lycium barbarum (Gou Ji Zi). Beijing; Jindun Press 2001: 1-16
• 4 Hsu H Y, Yang J J, Ho Y H, Lin C C. Difference in the effects of radioprotection between aerial and root parts of Lycium chinense.  J Ethnopharmacol. 1999;  64 101-108
• 5 Xiao P G, Xing S T, Wang L W. Immunological aspects of Chinese medicinal plants as antiageing drugs.  J Ethnopharmacol. 1993;  38 167-175
• 6 Li Y X, Li Y, Qian Z J, Kim M M, Kim S K. In vitro antioxidant activity of 5-HMF isolated from marine red alga Laurencia undulata in free-radical-mediated oxidative systems.  J Microbiol Biotechnol. 2009;  19 1319-1327
• 7 Kim K J, Kim Y M, Kim H Y, Ro J Y, Jeoung D. Inhibitory mechanism of anti-allergic peptides in RBL2H3 cells.  Eur J Pharmacol. 2008;  581 191-203
• 8 Beaven M A, Metzger H. Signal transduction by Fc receptors: the FcεRI case.  Immunol Today. 1993;  14 222-226
• 9 Schroeder J T, Kagey-Sobotka A, Lichtenstein L M. The role of the basophil in allergy inflammation.  Allergy. 1995;  50 463-472
• 10 Matsuda H, Morikawa T, Ueda K, Managi H, Yoshikawa M. Structural requirement of flavonoids for inhibition of antigen-induced degranulation, TNF-α and IL-4 production from RBL-2H3 cells.  Bioorg Med Chem. 2002;  10 3123-3128
• 11 Jeuring H J, Kuppers F J E M. High performance liquid chromatography of furfural and hydroxymethylfurfural in sprits and honey.  J Assoc Off Anal Chem. 1980;  63 1215-1218
• 12 Janzowski C V, Glaab E, Samimi J S, Eisenbrand G. 5-Hydroxymethylfurfural: assessment of mutagenicity, DNA-damaging potential and reactivity towards cellular glutathione.  Food Chem Toxicol. 2000;  38 801-809
• 13 Pichler N, Michael M. Determination of 5-Hydroxymethyl-2-furaldehyd (HMF) in sweet wine and balsamic vinegar.  News and References Archives. 2004;  11-22
• 14 Ulbricht R J, Northup S J, Thomas J A. A review of 5-hydroxymethylfurfural (HMF) in parenteral solutions.  Fundam Appl Toxicol. 1984;  4 843-853
• 15 Abdulmalik O, Safo M K, Chen Q K, Yang J S, Brugnara C, Ohene-Frempong K, Abraham D J, Asakura T. 5-Hydroxymethyl-2-furfural modifies intracellular sickle haemoglobin and inhibits sickling of red blood cells.  Brit J Haematol. 2005;  128 552-561
• 16 Matsuda E, Yoshizawa Y, Yokosawa Y, Watanabe N, Kawaii S, Murofushi N. Effects of Eucommia ulmoides Oliver leaf extract on 3T3-L1 differentiation into adipocytes.  J Nat Med. 2006;  60 126-129
• 17 Mossman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
• 18 Yamada P, Zarrouk M, Kawasaki K, Isoda H. Inhibitory effect of various Tunisian olive oils on chemical mediator release and cytokine production by basophilic cells.  J Ethnopharmacol. 2008;  116 279-287
• 19 Aase F, Arna S. Dantrolene prevents glutamate cytotoxicity and Ca⁺² release from intracellular stores in cultured cerebral cornical neurons.  J Neurochem. 1991;  56 1075-1078
• 20 Sugisawa A, Umegaki K. Physiological concentration of (−)-epigallocatechin-3-O-gallate (EGCg) prevent chromosomal damage induced by reactive oxygen species in WIL2-NS cells.  J Nutr. 2002;  132 1836-1839
• 21 Ding X, Wang M Y, Yao Y X, Li G Y, Cai B C. Protective effect of 5-hydroxymethylfurfural derived from processed Fructus Corni on human hepatocyte LO2 injured by hydrogen peroxide and its mechanism.  J Ethnopharmacol. 2010;  128 373-376
• 22 Surh Y J, Tannenbaum S R. Activation of the maillard reaction product 5-(hydroxymethyl) furfural to strong mutagens via allylic sulfonation and chlorination.  Chem Res Toxicol. 1994;  7 313-318
• 23 Durling L J K, Busk L, Hellman B E. Evaluation of the DNA damaging effect of the heat-induced food toxicant 5-hydroxymethylfurfural (HMF) in various cell lines with different activities of sulfotransferases.  Food Chem Toxicol. 2009;  47 880-884
• 24 Ohmi K, Kiyokawa N, Takeda T, Fujimoto J. Human microvascular endothelial cells are strongly sensitive to Shiga toxins.  Biochem Biophys Res Commun. 1998;  251 137-141
• 25 Severin I, Dumonta C, Jondeau-Cabatona A, Graillota V, Chagnon M C. Genotoxic activities of the food contaminant 5-hydroxymethylfurfural using different in vitro bioassays.  Toxicol Lett. 2010;  192 189-194
• 26 Safo M K, Abdulmalik O, Danso-Danquah R, Burnett J C, Nokuri S, Joshi G S, Musayev F N, Asakura T, Abraham D J. Structural basis for the potent antisickling effect of a novel class of five-membered heterocyclic aldehydic compounds.  J Med Chem. 2004;  47 4665-4676
• 27 Saracoglu I, Inoue M, Calis I, Ogihara Y. Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants Phlomis armeniaca and Scutellaria salviifolia.  Biol Pharm Bull. 1995;  18 1396-1400
• 28 Shinohara K, Kong Z L, Miwa M, Tsushida T, Kurogi M, Kitamura Y, Murakami H. Effects of mutagens on the viability and some enzymes of a serum free cultured human histiocytic lymphoma cell line, U-937.  Agric Biol Chem. 1990;  54 373-380
• 29 Novak N, Kraft S, Bieber T. IgE receptors.  Curr Opin Immunol. 2001;  13 721-726
• 30 Oka T, Sato K, Hori M, Ozaki H, Karaki H. FcεRI cross-linking-induced actin assembly mediates calcium signalling in RBL-2H3 mast cells.  Br J Pharmacol. 2002;  136 837-846
• 31 Kim Y, Lee Y S, Hahn J H, Choe J, Kwon H J, Ro J Y, Jeoung D. Hyaluronic acid targets CD44 and inhibits FcεRI signaling involving PKCδ, Rac1, ROS, and MAPK to exert anti-allergic effect.  Mol Immunol. 2008;  45 2537-2547
• 32 Suzuki M, Nakamura T, Iyoki S, Fujiwara A, Watanabe Y, Mohri K, Isobe K, Ono K, Yano S. Elucidation of anti-allergic activities of curcumin-related compounds with a special reference to their anti-oxidative activities.  Biol Pharm Bull. 2005;  28 1438-1443
• 33 Considine D M. Chemical and process technology encyclopedia, 2nd edition. New York; McGraw-Hill Book Co. Press 1974: 539
• 34 Budavari S. The Merck index, 11th edition. Rahway; Merck & Co., Inc. Press 1989: 767
• 35 Ukeda H, Goto Y, Sawamura M, Kusunose H, Kamikado H, Kamei T. Reduction of tetrazolium salt XTT with UHT-treated milk: its relationship with the extent of heat-treatment and storage conditions.  Food Sci Technol lnt. 1995;  1 52-57
• 36 Orak H H. Evaluation of antioxidant activity, colour and some nutritional characteristics of pomegranate (Punica granatum L.) juice and its sour concentrate processed by conventional evaporation.  Int J Food Sci Nutr. 2009;  60 1-11