Journal of Microbiology and Biotechnology

  • 제27권11호
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  • Pages.1916-1924
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  • 2017
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  • 1017-7825(pISSN)
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  • 1738-8872(eISSN)
한국미생물·생명공학회 (The Korean Society for Microbiology and Biotechnology)
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Glycosylation Enhances the Physicochemical Properties of Caffeic Acid Phenethyl Ester

  • Moon, Keum-Ok (Department of Microbiology, Pusan National University) ;
  • Park, Soyoon (Department of Microbiology, Pusan National University) ;
  • Joo, Myungsoo (School of Korean Medicine, Pusan National University) ;
  • Ha, Ki-Tae (School of Korean Medicine, Pusan National University) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Institute of Life Sciences & Resources, Kyung Hee University) ;
  • Park, Cheon-Seok (Graduate School of Biotechnology and Institute of Life Sciences & Resources, Kyung Hee University) ;
  • Cha, Jaeho (Department of Microbiology, Pusan National University)
  • 투고 : 2017.06.08
  • 심사 : 2017.09.04
  • 발행 : 2017.11.28
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초록

In this study, we synthesized a glycosylated derivative of caffeic acid phenethyl ester (CAPE) using the amylosucrase from Deinococcus geothermalis with sucrose as a substrate and examined its solubility, chemical stability, and anti-inflammatory activity. Nuclear magnetic resonance spectroscopy showed that the resulting glycosylated CAPE (G-CAPE) was the new compound caffeic acid phenethyl ester-4-O-${\alpha}-{\small{D}}$-glucopyranoside. G-CAPE was 770 times more soluble than CAPE and highly stable in Dulbecco's modified Eagle's medium and buffered solutions, as estimated by its half-life. The glycosylation of CAPE did not significantly affect its anti-inflammatory activity, which was assessed by examining lipopolysaccharide-induced nitric oxide production and using a nuclear factor erythroid 2-related factor 2 reporter assay. Furthermore, a cellular uptake experiment using high-performance liquid chromatography analysis of the cell-free extracts of RAW 264.7 cells demonstrated that G-CAPE was gradually converted to CAPE within the cells. These results demonstrate that the glycosylation of CAPE increases its bioavailability by helping to protect this vital molecule from chemical or enzymatic oxidation, indicating that G-CAPE is a promising candidate for prodrug therapy.

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