Inhibitory activity of 4-O-benzoyl-3′-O-(O-Methylsinapoyl)sucrose from polygala tenuifolia on Escherichia coli β-Glucuronidase

Jang Hoon Kim; Le Ba Vinh; Mok Hur; Sung Cheol Koo; Woo Tae Park; Youn Ho Moon; Yoon Jeong Lee; Young Ho Kim; Yun Chan Huh; Seo Young Yang

doi:10.4014/jmb.2108.08004

Inhibitory activity of 4-O-benzoyl-3′-O-(O-Methylsinapoyl)sucrose from polygala tenuifolia on Escherichia coli β-Glucuronidase

Jang Hoon Kim
, Le Ba Vinh
, Mok Hur
, Sung Cheol Koo
, Woo Tae Park
, Youn Ho Moon
, Yoon Jeong Lee
, Young Ho Kim
, Yun Chan Huh
, Seo Young Yang

Department of Biology Education

United States Food and Drug Administration
Vietnamese Academy of Science and Technology
Chungnam National University

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Bacterial β-glucuronidase in the intestine is involved in the conversion of 7-ethyl-10-hydroxycamptochecin glucuronide (derived from irinotecan) to 7-ethyl-10-hydroxycamptothecin, which causes intestinal bleeding and diarrhea (side effects of anti-cancer drugs). Twelve compounds (1-12) from Polygala tenuifolia were evaluated in terms of β-glucuronidase inhibition in vitro. 4-O-Benzoyl-3′-O-(O-methylsinapoyl) sucrose (C3) was highly inhibitory at low concentrations. C3 (an uncompetitive inhibitor) exhibited a k_i value of 13.4 μM; inhibitory activity increased as the substrate concentration rose. Molecular simulation revealed that C3 bound principally to the Gln158-Tyr160 enzyme loop. Thus, C3 will serve as a lead compound for development of new βglucuronidase inhibitors.

Original language	English
Pages (from-to)	1576-1582
Number of pages	7
Journal	Journal of Microbiology and Biotechnology
Volume	31
Issue number	11
DOIs	https://doi.org/10.4014/jmb.2108.08004
State	Published - 28 Nov 2021

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Molecular simulation
Polygala tenuifolia
Uncompetitive inhibitor
β-glucuronidase

Access to Document

10.4014/jmb.2108.08004

Cite this

@article{ef3c44c4a5294f7c964ceef2cbdba195,

title = "Inhibitory activity of 4-O-benzoyl-3′-O-(O-Methylsinapoyl)sucrose from polygala tenuifolia on Escherichia coli β-Glucuronidase",

abstract = "Bacterial β-glucuronidase in the intestine is involved in the conversion of 7-ethyl-10-hydroxycamptochecin glucuronide (derived from irinotecan) to 7-ethyl-10-hydroxycamptothecin, which causes intestinal bleeding and diarrhea (side effects of anti-cancer drugs). Twelve compounds (1-12) from Polygala tenuifolia were evaluated in terms of β-glucuronidase inhibition in vitro. 4-O-Benzoyl-3′-O-(O-methylsinapoyl) sucrose (C3) was highly inhibitory at low concentrations. C3 (an uncompetitive inhibitor) exhibited a ki value of 13.4 μM; inhibitory activity increased as the substrate concentration rose. Molecular simulation revealed that C3 bound principally to the Gln158-Tyr160 enzyme loop. Thus, C3 will serve as a lead compound for development of new βglucuronidase inhibitors.",

keywords = "Molecular simulation, Polygala tenuifolia, Uncompetitive inhibitor, β-glucuronidase",

author = "Kim, \{Jang Hoon\} and Vinh, \{Le Ba\} and Mok Hur and Koo, \{Sung Cheol\} and Park, \{Woo Tae\} and Moon, \{Youn Ho\} and Lee, \{Yoon Jeong\} and Kim, \{Young Ho\} and Huh, \{Yun Chan\} and Yang, \{Seo Young\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2021 by the authors. Licensee KMB. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.",

year = "2021",

month = nov,

day = "28",

doi = "10.4014/jmb.2108.08004",

language = "English",

volume = "31",

pages = "1576--1582",

journal = "Journal of Microbiology and Biotechnology",

issn = "1017-7825",

publisher = "Korean Society for Microbiolog and Biotechnology",

number = "11",

}

TY - JOUR

T1 - Inhibitory activity of 4-O-benzoyl-3′-O-(O-Methylsinapoyl)sucrose from polygala tenuifolia on Escherichia coli β-Glucuronidase

AU - Kim, Jang Hoon

AU - Vinh, Le Ba

AU - Hur, Mok

AU - Koo, Sung Cheol

AU - Park, Woo Tae

AU - Moon, Youn Ho

AU - Lee, Yoon Jeong

AU - Kim, Young Ho

AU - Huh, Yun Chan

AU - Yang, Seo Young

N1 - Publisher Copyright: Copyright © 2021 by the authors. Licensee KMB. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.

PY - 2021/11/28

Y1 - 2021/11/28

N2 - Bacterial β-glucuronidase in the intestine is involved in the conversion of 7-ethyl-10-hydroxycamptochecin glucuronide (derived from irinotecan) to 7-ethyl-10-hydroxycamptothecin, which causes intestinal bleeding and diarrhea (side effects of anti-cancer drugs). Twelve compounds (1-12) from Polygala tenuifolia were evaluated in terms of β-glucuronidase inhibition in vitro. 4-O-Benzoyl-3′-O-(O-methylsinapoyl) sucrose (C3) was highly inhibitory at low concentrations. C3 (an uncompetitive inhibitor) exhibited a ki value of 13.4 μM; inhibitory activity increased as the substrate concentration rose. Molecular simulation revealed that C3 bound principally to the Gln158-Tyr160 enzyme loop. Thus, C3 will serve as a lead compound for development of new βglucuronidase inhibitors.

AB - Bacterial β-glucuronidase in the intestine is involved in the conversion of 7-ethyl-10-hydroxycamptochecin glucuronide (derived from irinotecan) to 7-ethyl-10-hydroxycamptothecin, which causes intestinal bleeding and diarrhea (side effects of anti-cancer drugs). Twelve compounds (1-12) from Polygala tenuifolia were evaluated in terms of β-glucuronidase inhibition in vitro. 4-O-Benzoyl-3′-O-(O-methylsinapoyl) sucrose (C3) was highly inhibitory at low concentrations. C3 (an uncompetitive inhibitor) exhibited a ki value of 13.4 μM; inhibitory activity increased as the substrate concentration rose. Molecular simulation revealed that C3 bound principally to the Gln158-Tyr160 enzyme loop. Thus, C3 will serve as a lead compound for development of new βglucuronidase inhibitors.

KW - Molecular simulation

KW - Polygala tenuifolia

KW - Uncompetitive inhibitor

KW - β-glucuronidase

UR - https://www.scopus.com/pages/publications/85120683224

U2 - 10.4014/jmb.2108.08004

DO - 10.4014/jmb.2108.08004

M3 - Article

C2 - 34528918

AN - SCOPUS:85120683224

SN - 1017-7825

VL - 31

SP - 1576

EP - 1582

JO - Journal of Microbiology and Biotechnology

JF - Journal of Microbiology and Biotechnology

IS - 11

ER -

Inhibitory activity of 4-O-benzoyl-3′-O-(O-Methylsinapoyl)sucrose from polygala tenuifolia on Escherichia coli β-Glucuronidase

Abstract

UN SDGs

Keywords

Access to Document

Other files and links

Fingerprint

Cite this