Abstract
In an ongoing search of compounds from natural sources that exhibit anti-allergic properties, 3 flavonoids were isolated from the ethyl acetatefraction of methanol extracts of gujeolcho (Chrysanthemum zawadskii var. latilobum), with guided histamine release inhibitory effects. The isolated compounds were identified as eriodictyol-7-O-β-d-glucuronide, 5,7-dihydroxy-4-chromene, and 6-methoxyluteolin based on spectroscopic evidences including NMR and MS spectra. These results suggest that gujeolcho extracts and 3 compounds would be candidates as therapeutic or preventive agents for allergic reaction.
Similar content being viewed by others
References
Beaven MA, Metzer H. Signal transduction by Fc receptors: The FcɛRI case. Immunol. Today 14: 222–226 (1993)
Drombrowicz DV, Flamand KK, Brigman BH, Koller JP, Kinet JP. Abolition of anaphylaxis by targeted distruption of the high affinity immunoglobulin E receptor ɛ chain gene. Cell 75: 969–976 (1993)
Kinet JP, Blank U, Brini A, Jouvin MH, Kuster H, Mejan O, Ra C. The high affinity receptor for immunoglobulin E: A target for therapy of allergic diseases. Int. Arch. Aller. A. Imm. 94: 51–55 (1991)
Kinet JP. The high affinity IgE receptor (FcɛRI): From physiology to pathology. Annu. Rev. Immunol. 17: 931–972 (1999)
Kwon HS, Ha TJ, Hwang SW, Jin YM, Nam SH, Park KH, Yang MS. Cytotoxic flavonoids from the whole plants of Chrysanthemum zawadskii Herbich var. latilobum Kitamura. J. Life Sci. 16: 746–749 (2006)
Seo JY, Lim SS, Park JA, Lim JS, Kim HJ, Kang HJ, Yoon Park JH, Kim JS. Protection by Chrysanthemum zawadskii extract from liver damage of mice caused by carbon tetrachloride is maybe mediated by modulation of QR activity. Nutr. Res. Pract. 4: 93–98 (2010)
Singh RP, Agrawal P, Yim DS, Agarwal C, Agarwal R. Acacetin inhibits cell growth and cell cycle progression, and induces apoptosis in human prostate cancer cells: Structure-activity relationship with linarin and linarin acetate. Carcinogenesis 26: 845–854 (2005)
Kim YY, Lee SY, Yim DS. Biological activities of linarin from Chrysanthemum zawadskii var latilobum. J. Pharm. Soc. Korea 45: 604–610 (2001)
Hsu YL, Kuo PL, Lin CC. Acacetin inhibits the proliferation of HepG2 by blocking cell cycle progression and inducing apoptosis. Biochem. Pharmacol. 67: 823–829 (2004)
Kim YY, Lee SY, Yim DS. Biological activities of linarin from Chrysanthemum zawadskii var. latilobum. Yakhak Hoeji 45: 604–610 (2001)
Han S, Sung KH, Yim D, Lee S, Lee CK, Ha NJ, Kim K. The effect of linarin on LPS-induced cytokine production and nitric oxide inhibition in murine macrophage cell line RAW264.7. Arch. Pharm. Res. 25: 170–177 (2002)
Han LK, Sumiyoshi M, Zheng YN, Okuda H, Kimura Y. Antiobesity action of Salix matsudana leaves (Part 2). Isolation of antiobesity effectors from polyphenol fractions of Salix matsudana. Phytother. Res. 17: 1195–1198 (2003)
Middleton EJ. Effect of plant flavonoids on immune and inflammatory cell function. Adv. Exp. Med. Biol. 439: 175–182 (1998)
Itoh T, Ohguchi K, Iinuma M, Nozawa Y, Akao Y. Inhibitory effects of polymethoxy flavones isolated from citrus reticulate on degranulation in rat basophilic leukemia RBL-2H3: Enhanced inhibition by their combination. Bioorg. Med. Chem. 16: 7592–7598 (2008)
Segawa S, Yasui K, Takata Y, Kurihara T, Kaneda H, Watari J. Flavonoid glycosides extracted from hop (Hummulus lupulus L.) as inhibitor of chemical mediator release from human basophilic KU812 cells. Biosci. Biotech. Bioch. 70: 2990–2997 (2006)
Tachibana H, Sunada Y, Miyase T, Sano M, Maeda-Yamamoto M, Yamada K. Identification of a methylated tea catechin as an inhibitor of degranulation in human basophilic KU812 cells. Biosci. Biotech. Bioch. 64: 452–454 (2000)
Fujimura Y, Tachibana H, Maeda-Yamamoto M, Miyase T, Sano M, Yamada K. Antiallergic tea catechin, (-)-epigallocatechin-3-O-(3-Omethyl)-gallate, suppresses FcɛRI expression in human basophilic KU812 cells. J. Agr. Food Chem. 50: 5729–5734 (2002)
Li Y, Lee SH, Le QT, Kim MM, Kim SK. Anti-allergic effects of phlorotannins on histamine release via binding inhibition between IgE and FcɛRI. J. Agr. Food Chem. 56: 12073–12080 (2008)
Shim SY, Choi JS, Byun DS. Kaempferol isolated from Nelumbo nucifera stamens negatively regulates FcepsilonRI expression in human basophilic KU812F cells. J. Microbiol. Biotechn. 19: 155–160 (2009)
Shim SY, Choi JS, Byun DS. Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on FcɛRI expression. Bioorg. Med. Chem. 17: 4734–4739 (2009)
Shim SY, Byun DS. Inhibitory effects of Chrysanthemum zawadsaki ethanolic extract on FcɛRI α chain expression. Korean J. Food Sci. Technol. 43: 220–223 (2011)
Shore PA, Burkhalter A, Cohn VH, Victor HC. A method for the fluorometric assay of histamine in tissues. J. Pharmacol. Exp. Ther. 127: 182–186 (1959)
Ringl A, Prinz S, Huefner A, Kurzmann M, Kopp B. Chemosystematic value of flavonoids from Crataegus×macrocarpa (Rosaceae) with special emphasis on (R)- and (S)-eriodictyol-7-Oglucuronide and luteolin-7-O-glucuronide. Chem. Biodivers. 4: 154–162 (2007)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shim, SY., Kang, HS., Sun, HJ. et al. Isolation and identification of flavonoids from Gujeolcho (Chrysanthemum zawadskii var. latilobum) as inhibitor of histamine release. Food Sci Biotechnol 21, 613–617 (2012). https://doi.org/10.1007/s10068-012-0079-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10068-012-0079-0