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Microbiology and Biotechnology Letters

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Microbial Biotechnology  |  Whole Cell Biocatalysis and Bioprocess Engineering

Microbiol. Biotechnol. Lett.

Received: March 10, 2022; Revised: April 13, 2022

Synthesis of α-cichoriin using Deinococcus geothermalis amylosucrase and its antiproliferative effect

Keumok Moon 1, Hyun Su Park 2, Areum Lee 3, Jugyeong Min 3, Yunjung Park 3 and Jaeho Cha 1, 3*

1Microbiological Resource Research Institute, Pusan National University, Busan 46241, Republic of Korea, 2Manufacturing Divisional Group, Cellario, Inc., Incheon 22014, Republic of Korea, 3Department of Microbiology, Pusan National University, Busan 46241, Republic of Korea

Correspondence to :
Jaeho Cha, 2 Busandaehak-ro 63beon-gil, Geumjeong-gu, Busan 46241, Republic of Korea [46241]
Tel : 0515102196, Fax : 0515141778, E-mail : jhcha@pusan.ac.kr

Abstract

Glycosylation of aesculetin was performed using amylosucrase from the hyperthermophilic bacterium Deinococcus geothermalis DSM 11300 to improve the solubility and biological activity of aesculetin. A newly synthesized aesculetin glycoside was identified as α-cichoriin (aesculetin 7-α-D-glucoside) by nuclear magnetic resonance analysis. The solubility of α-cichoriin was 11 times higher than that of aesculetin because of the attached glucose moiety. Aesculetin and α-cichoriin had no significant effect on the proliferation of normal cells, such as RAW 264.7, but they showed a cell proliferation inhibitory effect on B16F10 melanoma cells. Unlike treatment with aesculetin and α-cichoriin, aesculin (aesculetin 6-β-D-glucoside) showed no antiproliferative activity in B16F10 cells. Based on the molecular structures of aesculin and α-cichoriin, the position where glucose binds to aesculetin and the anomeric configuration between glucose and aesculetin are thought to be important for exerting an antiproliferative effect on the B16F10 cell line. Based on these results, we propose that α-cichoriin, the α-glycosylated form of aesculetin, may serve as a model for developing phytochemical analogs with therapeutic potential for the treatment of diseases associated with tumor cell proliferation without cytotoxicity to normal cells.

Keywords: aesculetin, α-cichoriin, amylosucrase, transglycosylation, antiproliferative activity

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