<i>β</i>-Glucuronidase inhibitory activity of bromophenol isolated from red alga <i>Grateloupia lancifolia</i>

The Han Nguyen; Patrick Achiever Blamo Jr; Xiaoyong Liu; Thi Van Anh Tran; Sang Moo Kim; The Han Nguyen; Patrick Achiever Blamo Jr; Xiaoyong Liu; Thi Van Anh Tran; Sang Moo Kim

doi:10.3934/agrfood.2021032

AIMS Agriculture and Food

2021, Volume 6, Issue 2: 551-559. doi: 10.3934/agrfood.2021032

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Research article

β-Glucuronidase inhibitory activity of bromophenol isolated from red alga Grateloupia lancifolia

1.
Faculty of Food Technology, Nha Trang University, 02 Nguyen Dinh Chieu Street, Nha Trang City, Khanh Hoa, Vietnam
2.
Haizhibao Deutschland GmbH, Heiliggeistgasse 28, 85354 Freising Munish, Germany
3.
Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh City, 41 Dinh Tien Hoang Street, Ho Chi Minh City, Vietnam
4.
Department of Marine Food Science and Technology, Gangneung-Wonju National University, 7 Jukheon-gil, Gangneung 25457, Republic of Korea

Received: 02 December 2020 Accepted: 24 February 2021 Published: 25 April 2021

The human gastrointestinal (GI) tract plays an important role in disease and health. The overexpression of β-glucuronidase, an enzyme produced in the gastrointestinal tract, has been found to cause the retoxification of potentially damaging substances already detoxified by liver glucuronidation. Thus, β-glucuronidase has been implicated in a number of diseases including colon cancer, liver disease and Crohn's disease. This study investigated β-glucuronidase inhibitory activity of a bromophenol purified from the red alga Grateloupia lancifolia. Using an assay-guided fractionation technique, a bromophenol, bis(2, 3-dibromo-4, 5-dihydroxybenzyl) ether, a bromophenol, was isolated from the red alga G. lancifolia. Its structure was elucidated on the basis of extensive 1D- and 2D-NMR studies, high resolution EI-MS analysis and comparisons with literature data. Bis(2, 3-dibromo-4, 5-dihydroxybenzyl) ether showed potent β-glucuronidase inhibitory activity. The IC₅₀ and K_I values of bromophenol against E. coli β-glucuronidase were 0.54 and 0.53 mM, respectively. This bromophenol inhibited β-glucuronidase competitively and was stable at pH 2 up to 40 min at 37 ℃.
- β-glucuronidase inhibitor,
- bromophenol,
- Grateloupia lancifolia
Citation: The Han Nguyen, Patrick Achiever Blamo Jr, Xiaoyong Liu, Thi Van Anh Tran, Sang Moo Kim. β-Glucuronidase inhibitory activity of bromophenol isolated from red alga Grateloupia lancifolia[J]. AIMS Agriculture and Food, 2021, 6(2): 551-559. doi: 10.3934/agrfood.2021032

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Abstract

The human gastrointestinal (GI) tract plays an important role in disease and health. The overexpression of β-glucuronidase, an enzyme produced in the gastrointestinal tract, has been found to cause the retoxification of potentially damaging substances already detoxified by liver glucuronidation. Thus, β-glucuronidase has been implicated in a number of diseases including colon cancer, liver disease and Crohn's disease. This study investigated β-glucuronidase inhibitory activity of a bromophenol purified from the red alga Grateloupia lancifolia. Using an assay-guided fractionation technique, a bromophenol, bis(2, 3-dibromo-4, 5-dihydroxybenzyl) ether, a bromophenol, was isolated from the red alga G. lancifolia. Its structure was elucidated on the basis of extensive 1D- and 2D-NMR studies, high resolution EI-MS analysis and comparisons with literature data. Bis(2, 3-dibromo-4, 5-dihydroxybenzyl) ether showed potent β-glucuronidase inhibitory activity. The IC₅₀ and K_I values of bromophenol against E. coli β-glucuronidase were 0.54 and 0.53 mM, respectively. This bromophenol inhibited β-glucuronidase competitively and was stable at pH 2 up to 40 min at 37 ℃.

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