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

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

4 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

Keywords

Molecular simulation
Polygala tenuifolia
Uncompetitive inhibitor
β-glucuronidase

UN SDGs

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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.",

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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}",

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year = "2021",

month = nov,

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doi = "10.4014/jmb.2108.08004",

language = "English",

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journal = "Journal of Microbiology and Biotechnology",

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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

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DO - 10.4014/jmb.2108.08004

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AN - SCOPUS:85120683224

SN - 1017-7825

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ER -

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

Abstract

Keywords

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