DOI QR코드

DOI QR Code

Antioxidant and Prolyl Endopeptidase Inhibitory Capacities of Chromone C-glucosides from the Clove Buds (Syzygium aromaticum)

  • Han, Ah-Reum (Department of Applied Chemistry and Plant Metabolism Research Center, Kyung Hee University) ;
  • Paik, Young-Sook (Department of Applied Chemistry and Plant Metabolism Research Center, Kyung Hee University)
  • Received : 2012.07.30
  • Accepted : 2012.08.17
  • Published : 2012.09.30

Abstract

Four chromone derivatives (1-4) were isolated from the clove buds (Syzygium aromaticum). Of these, two chromone C-glucosides (1 and 2) showed significant PEP inhibition with $IC_{50}$ values of $1.48{\pm}0.02$ and $1.74{\pm}0.03{\mu}M$ and $K_i$ values of $0.27{\pm}0.02$ and $0.50{\pm}0.05{\mu}M$, respectively. They also exhibited strong antioxidant capacities against the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid diammonium salt radical system with $EC_{50}$ values of $4.13{\pm}0.04$ and $4.79{\pm}0.03{\mu}M$, respectively.

Keywords

References

  1. Coxon DT, Curtis RF, Price KR, and Levett G (1973) Abnormal metabolites produced by Daucus carota roots stored under conditions of stress. Phytochemistry 12, 1881-5. https://doi.org/10.1016/S0031-9422(00)91505-X
  2. Han AR and Paik YS (2010) Identification and PEP inhibitory activity of acetophenone glycosides from the clove buds (Syzygium aromaticum). J Korean Soc Appl Biol Chem 53, 847-51. https://doi.org/10.3839/jksabc.2010.129
  3. Kalinin AV and Snieckus V (1998) 4,6-Dimethoxy-3,7-dimethylcoumarin from Colchicum decaisnei. Total synthesis by carbamoyl Baker- Venkataraman rearrangement and structural revision to isoeugenitin methyl ether. Tetrahedron Lett 39, 4999-5002. https://doi.org/10.1016/S0040-4039(98)00978-2
  4. Lagow B (2004) PDR for herbal medicines. In Clove Syzygium aromaticum, (3rd ed.), pp. 204-8, Thomson PDR, USA.
  5. Lee JH, Lee SY, Lee KS, Jang HJ, Lee KH, Hahn TR et al. (2004) Prolyl endopeptidase inhibitors from the leaves of Ginkgo biloba. Planta Med 70, 1228-30. https://doi.org/10.1055/s-2004-835856
  6. Lee KG and Shibamoto T (2001) Antioxidant property of aroma extract from clove buds [Syzygium aromaticum (L.) Merr. et Perry]. Food Chem 74, 443-8. https://doi.org/10.1016/S0308-8146(01)00161-3
  7. Park YS, Jang HJ, and Paik YS (2005) Prolyl endopeptidase inhibitory activity of ursolic and oleanolic acids from corni fructus. Agric Chem Biotechnol 48, 207-12.
  8. 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, 1238-42. https://doi.org/10.1021/jf052521h
  9. 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, 1232-7. https://doi.org/10.1248/cpb.41.1232
  10. 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, 1232-7. https://doi.org/10.1248/cpb.41.1232

Cited by

  1. Synthesis, Photophysical, Electrochemical Studies, and Antioxidant Properties of Fluorescein-Linked Glycodendrimers vol.5, pp.9, 2016, https://doi.org/10.1002/ajoc.201600286
  2. Prolyl Endopeptidase Inhibitory Activity of Two Styrylpyranones from Phellinus linteus vol.56, pp.3, 2012, https://doi.org/10.3839/jabc.2013.029
  3. Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features vol.26, pp.24, 2012, https://doi.org/10.3390/molecules26247646