Abstract
Two new acetophenone glucosides, 2,6-dihydroxy-4-methoxyacetophenone 3-C-β-D-glucoside (1) and 2,6-dihydroxy-4-methoxyacetophenone 3-C-β-D-(6′-O-galloyl)glucoside (2), together with three known compounds, eugenin (3), 8-C-glucosylnoreugenin (4), and gallic acid (5) were isolated from the EtOAc soluble fraction of the MeOH extract of clove buds (Syzygium aromaticum). Of these, compound 2 showed significant prolyl endopeptidase inhibitory activity with IC50 value of 17.2±1.1 μM, suggesting it may have potential use against memory impairment and cognitive decline.
This is a preview of subscription content, log in via an institution to check access.
References
Coxon DT, Curtis RF, Price KR, and Levett G (1973) Abnormal metabolites produced by Daucus carota roots stored under conditions of stress. Phytochemistry 12, 1881–1885.
Lagow B (2004) PDR for herbal medicines. In Clove Syzygium aromaticum, (3rd ed.), pp. 204–208. Thomson PDR, Montvale, NJ, USA.
Lee JH, Lee SY, Lee KS, Jang HJ, Lee KH, Hahn TR, and Paik YS (2004) Prolyl endopeptidase inhibitors from the leaves of Ginkgo biloba. Planta Med 70, 1228–1230.
Lee KG and Shibamoto T (2001) Antioxidant property of aroma extract from clove buds (Syzygium aromaticum L. Merr. et Perry). Food Chem 74, 443–448.
Okamura N, Hine N, Tateyama Y, Nakazawa M, Fujioka T, Mihashi K, and Yagi A (1998) Five chromones from Aloe vera leaves. Phytochemistry 49, 219–223.
Park YS, Jang HJ, and Paik YS (2005) Prolyl endopeptidase inhibitory activity of ursolic and oleanolic acids from corni fructus. Agric Chem Biotechnol 48, 207–212.
Park YS, Jang HJ, Lee KH, Hahn TR, and Paik YS (2006) Prolyl endopeptidase inhibitory activity of unsaturated fatty acids. J Agric Food Chem 54, 1238–1242.
Tanaka T, Orii Y, Nonaka G, and Nishioka I (1993) Tannins and related compounds. CXXIII. Chromone, acetophenone and phenylpropanoid glycosides and their galloyl and/or hexahydroxydiphenoyl esters from the leaves of Syzygium aromaticum Merr. et Perry. Chem Pharm Bull 41, 1232–1237.
Tuntiwachwuttikul P, Phansa P, Pootaeng-on Y, and Taylor WC (2006) Chromones from the branches of Harrisonia perforate. Chem Pharm Bull 54, 44–47.
Yoshimoto T, Walter R, and Tsuru D (1980) Proline-specific endopeptidase from Flavobacterium. Purification and properties. J Biol Chem 255, 4786–4792.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Han, AR., Paik, YS. Identification and PEP inhibitory activity of acetophenone glucosides from the clove buds (Syzygium aromaticum). J. Korean Soc. Appl. Biol. Chem. 53, 847–851 (2010). https://doi.org/10.3839/jksabc.2010.129
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.3839/jksabc.2010.129