Microbiology and Biotechnology Letters (한국미생물·생명공학회지)

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
권호 표지
DOI QR코드

DOI QR Code

Isolation and Characterization of α-glucosidase Inhibitors from Euonymus alatus

화살나무(Euonymus alatus)로 부터 α-glucosidase 저해 물질의 분리 및 동정

  • Kim, Shin-Duk (Department of Chemical and Biological Engineering, Seokyeong University)
  • 김신덕 (서경대학교화학생명공학과)
  • Received : 2017.10.16
  • Accepted : 2017.12.19
  • Published : 2017.12.28
Download PDF
⟨ Previous Next ⟩

Abstract

${\alpha}$-glucosidase inhibitory compounds (1-4) in a 50% methanol extract of Euonymus alatus were isolated by activity-based fractionations and the structures determined on the basis of chemical and spectral characterization techniques such as $^1H$ and $^{13}C$ nuclear magnetic resonance spectroscopy, $^1H-^1H$ correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC). The compounds 1-4 belong to flavonols and exhibited potent inhibitory activities against ${\alpha}$-glucosidase, with $IC_{50}$ values of 25.3, 17.1, 47.3, and $35.1{\mu}M$, respectively. All the isolated compounds were more potent than the positive control acarbose. This is the first report describing the potential hypoglycemic effect of Euonymus alatus through ${\alpha}$-glucosidase inhibition and identification of its active components.

화살나무 가지로부터 activity based fractionation에 의해 ${\alpha}$-glucosidase 저해 활성 물질 compound 1-4을 분리하였고, $^1H$ NMR, $^{13}C$ NMR, $^1H-^1H$ COSY와 HMBC 등의 spectral data에 의해 구조를 결정하였다. Compound 1-4는 모두 flavonol 물질로 ${\alpha}$-glucosidase에 대해 $IC_{50}$ 값이 각각 25.3, 17.1, 47.3과 $35.1{\mu}M$로 positive control로 사용한 acarbose 보다 강한 활성을 나타내었다. 화살나무의 혈당 저하 기능의 유효성분으로 처음 동정된 Compound 1-4는 ${\alpha}$-glucosidase에만 특이적 활성을 갖는 물질로 당뇨병 치료제로의 개발 가능성이 높은 물질로 사료된다.

Keywords

References

  1. Heacock PM, Hertzler SR, Williams JA, Wolf BW. 2005. Effects of a medical food containing an herbal ${\alpha}$-glucosidase inhibitor on postprandial glycemia and insulinemia in healthy adults. J. Am. Diet. Assoc. 105: 65-71.
  2. Chapel C, Garcia C, Roingeard P, Zitzmann N, Dubuisson J, Dwek A, et al. 2006. Antiviral effect of ${\alpha}$-glucosidase inhibitors on viral morphogenesis and binding properties of the hepatitis C viruslike particles. J. Gen. Virol. 87: 861-871. https://doi.org/10.1099/vir.0.81503-0
  3. Goss PE, Baker MA, Carver JP, Dennis JW. 1995. Inhibitors of carbohydrate processing: a new class of anticancer agents. Clin. Cancer Res. 1: 935-944.
  4. Asano N. 2003. Glycosidase inhibitors: Update and perspectives on practical use. Glycobiology 13: 93R-104R. https://doi.org/10.1093/glycob/cwg090
  5. Yang Z, Wang Y, Wang Y, Zhang Y. 2012. Bioassay-guided screening and isolation of ${\alpha}$-glucosidase and tyrosinase inhibitors from leaves of Morus alba. Food Chem. 131: 617-625. https://doi.org/10.1016/j.foodchem.2011.09.040
  6. Wang SM, Han JJ, Ma K, Jin T, Bao L, Pei Y, et al. 2014. New ${\alpha}$- glucosidase inhibitors with p-terphenyl skeleton from the mushroom Hydnellum concrescens. Fitoterapia 98: 149-155. https://doi.org/10.1016/j.fitote.2014.07.019
  7. Park SH, Ko SK, Chung SH. 2005. Euonymus alatus prevents the hyperglycemia and hyperlipidemia induced by high-fat diet in ICR mice. J. Ethnopharmacol. 102: 326-335. https://doi.org/10.1016/j.jep.2005.06.041
  8. Markham KR. 1982. Techniques of flavonoid identification, pp. 23-29. Academic Press, London.
  9. Kim S. 2013. ${\alpha}$-Glucosidase inhibitor from Buthus martensi Karsch, Food Chem. 136: 297-300. https://doi.org/10.1016/j.foodchem.2012.08.063
  10. Sakakibara H, Honda Y, Nakagawa S, Ashida H, Kanazawa K. 2003. Simultaneous determination of all polyphenols in vegetables, fruits, and teas. J. Agric. Food Chem. 51: 571-581. https://doi.org/10.1021/jf020926l
  11. Agrawal PK. 1992. NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochem. 31: 3307- 3330. https://doi.org/10.1016/0031-9422(92)83678-R
  12. Harborne JB, Williams CA. 1994. Flavone and flavonol glycosides, pp 290-295. In Harborne JB (ed), The Flavonoids: Advances in research since 1986. Chapman & Hall, London.
  13. Madikizela B, Aderogba M, Staden JV. 2013. Isolation and characterization of antimicrobial constituents of Searsia chirindensis L. (Anacardiaceae) leaf extracts. J. Ethnopharmacol. 150: 609-613. https://doi.org/10.1016/j.jep.2013.09.016
  14. Toda M, Kawabata J, Kasai T. 2000. ${\alpha}$-Glucosidase inhibitors from clove (Syzgium aromaticum). Biosci. Biotechnol. Biochem. 64: 294-298. https://doi.org/10.1271/bbb.64.294
  15. Niwa T, Doi U, Osawa T. 2003. Inhibitory activity of corn-derived bisamide compounds against ${\alpha}$-glucosidase. J. Agric. Food Chem. 51: 90-94. https://doi.org/10.1021/jf020758x
  16. Peng X, Zhang G, Liao Y, Gong D. 2016. Inhibitory kinetics and mechanism of Kaemferol on ${\alpha}$-glucosidase. Food Chem. 190: 207-215. https://doi.org/10.1016/j.foodchem.2015.05.088
  17. Asano N. 2003. Glycosidase inhibitors: update and perspectives on practical use. Glycobiology 13: 93R-104R. https://doi.org/10.1093/glycob/cwg090
  18. Jacob GS. 1995. Glycosylation inhibitors in biology and medicine. Curr. Opin. Struct. Biol. 5: 605-611. https://doi.org/10.1016/0959-440X(95)80051-4