Xanthine Oxidase Inhibition and Anti-LDL Oxidation by Prenylated Isoflavones from Flemingia philippinensis Root
Xanthine oxidase is a frontier enzyme to produce oxidants, which leads to inflammation in the blood. Prenylated isoflavones from were found to display potent inhibition against xanthine oxidase (XO). All isolates ( - ) inhibited XO enzyme with IC ranging 7.8~36.4 μM. The most active isoflavones ( -...
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| creator | Kim, Jeong Yoon Wang, Yan Li, Zuo Peng Baiseitova, Aizhamal Ban, Yeong Jun Park, Ki Hun |
| description | Xanthine oxidase is a frontier enzyme to produce oxidants, which leads to inflammation in the blood. Prenylated isoflavones from
were found to display potent inhibition against xanthine oxidase (XO). All isolates (
-
) inhibited XO enzyme with IC
ranging 7.8~36.4 μM. The most active isoflavones (
-
, IC
= 7.8~14.8 μM) have the structural feature of a catechol motif in B-ring. Inhibitory behaviors were disclosed as a mixed type I mode of inhibition with
<
. Binding affinities to XO enzyme were evaluated. Fluorescence quenching effects agreed with inhibitory potencies (IC
s). The compounds (
-
) also showed potent anti-LDL oxidation effects in the thiobarbituric acid-reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. The compound
protected LDL oxidation with 0.7 μM in TBARS assay, which was 40-fold more active than genistein (IC
= 30.4 μM). |
| doi_str_mv | 10.3390/molecules25133074 |
| format | Article |
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were found to display potent inhibition against xanthine oxidase (XO). All isolates (
-
) inhibited XO enzyme with IC
ranging 7.8~36.4 μM. The most active isoflavones (
-
, IC
= 7.8~14.8 μM) have the structural feature of a catechol motif in B-ring. Inhibitory behaviors were disclosed as a mixed type I mode of inhibition with
<
. Binding affinities to XO enzyme were evaluated. Fluorescence quenching effects agreed with inhibitory potencies (IC
s). The compounds (
-
) also showed potent anti-LDL oxidation effects in the thiobarbituric acid-reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. The compound
protected LDL oxidation with 0.7 μM in TBARS assay, which was 40-fold more active than genistein (IC
= 30.4 μM).</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules25133074</identifier><identifier>PMID: 32640700</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>anti-LDL oxidation ; Antioxidants ; Atherosclerosis ; Bone density ; Catechol ; Chromatography, Liquid ; Copper - chemistry ; Copper compounds ; Electrophoretic mobility ; Enzyme Inhibitors - chemistry ; Enzymes ; Fabaceae - chemistry ; Flemingia philippinensis ; Fluorescence ; Genistein ; Inhibitory Concentration 50 ; Isoflavones ; Isoflavones - analysis ; Isoflavones - chemistry ; Isoflavones - isolation & purification ; Isoflavones - pharmacology ; Kinetics ; Lag time ; Legumes ; Lipoproteins, LDL - metabolism ; Low density lipoprotein ; Mass Spectrometry ; Metabolites ; Oxidants ; Oxidation ; Oxidation effects ; Oxidation-Reduction ; Oxidative stress ; Oxidizing agents ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; Plant Roots - chemistry ; prenylated isoflavones ; Prenylation ; Thiobarbiturates - chemistry ; Thiobarbituric acid ; Uric acid ; Xanthine oxidase ; Xanthine Oxidase - antagonists & inhibitors ; Xanthine Oxidase - metabolism ; xanthine oxidase inhibition</subject><ispartof>Molecules (Basel, Switzerland), 2020-07, Vol.25 (13), p.3074</ispartof><rights>2020. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c493t-63114e808bd07c109596388190bbfff6cc3d9c5ff297c2c500508e4ac74e5283</citedby><cites>FETCH-LOGICAL-c493t-63114e808bd07c109596388190bbfff6cc3d9c5ff297c2c500508e4ac74e5283</cites><orcidid>0000-0003-2817-1648 ; 0000-0002-1549-8978</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7411605/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7411605/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2102,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32640700$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Jeong Yoon</creatorcontrib><creatorcontrib>Wang, Yan</creatorcontrib><creatorcontrib>Li, Zuo Peng</creatorcontrib><creatorcontrib>Baiseitova, Aizhamal</creatorcontrib><creatorcontrib>Ban, Yeong Jun</creatorcontrib><creatorcontrib>Park, Ki Hun</creatorcontrib><title>Xanthine Oxidase Inhibition and Anti-LDL Oxidation by Prenylated Isoflavones from Flemingia philippinensis Root</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Xanthine oxidase is a frontier enzyme to produce oxidants, which leads to inflammation in the blood. Prenylated isoflavones from
were found to display potent inhibition against xanthine oxidase (XO). All isolates (
-
) inhibited XO enzyme with IC
ranging 7.8~36.4 μM. The most active isoflavones (
-
, IC
= 7.8~14.8 μM) have the structural feature of a catechol motif in B-ring. Inhibitory behaviors were disclosed as a mixed type I mode of inhibition with
<
. Binding affinities to XO enzyme were evaluated. Fluorescence quenching effects agreed with inhibitory potencies (IC
s). The compounds (
-
) also showed potent anti-LDL oxidation effects in the thiobarbituric acid-reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. The compound
protected LDL oxidation with 0.7 μM in TBARS assay, which was 40-fold more active than genistein (IC
= 30.4 μM).</description><subject>anti-LDL oxidation</subject><subject>Antioxidants</subject><subject>Atherosclerosis</subject><subject>Bone density</subject><subject>Catechol</subject><subject>Chromatography, Liquid</subject><subject>Copper - chemistry</subject><subject>Copper compounds</subject><subject>Electrophoretic mobility</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzymes</subject><subject>Fabaceae - chemistry</subject><subject>Flemingia philippinensis</subject><subject>Fluorescence</subject><subject>Genistein</subject><subject>Inhibitory Concentration 50</subject><subject>Isoflavones</subject><subject>Isoflavones - analysis</subject><subject>Isoflavones - chemistry</subject><subject>Isoflavones - isolation & purification</subject><subject>Isoflavones - pharmacology</subject><subject>Kinetics</subject><subject>Lag time</subject><subject>Legumes</subject><subject>Lipoproteins, LDL - metabolism</subject><subject>Low density lipoprotein</subject><subject>Mass Spectrometry</subject><subject>Metabolites</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidation effects</subject><subject>Oxidation-Reduction</subject><subject>Oxidative stress</subject><subject>Oxidizing agents</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Roots - chemistry</subject><subject>prenylated isoflavones</subject><subject>Prenylation</subject><subject>Thiobarbiturates - chemistry</subject><subject>Thiobarbituric acid</subject><subject>Uric acid</subject><subject>Xanthine oxidase</subject><subject>Xanthine Oxidase - antagonists & inhibitors</subject><subject>Xanthine Oxidase - metabolism</subject><subject>xanthine oxidase inhibition</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>DOA</sourceid><recordid>eNplkVtrFDEUxwdRbK1-AF8k4PPoyW0yeRFKa3VhoSJ98C1kctnNMpOMSba4395pt5YWn87hXH7n8m-a9xg-USrh85RGZ_ajK4RjSkGwF80pZgRaCky-fOKfNG9K2QEQzDB_3ZxQ0jEQAKdN-qVj3Ybo0PWfYHVxaBW3YQg1pIh0tOg81tCuL9fH_H14OKAf2cXDqKuzaFWSH_Vtiq4gn9OErkY3hbgJGs3bMIZ5XuixhIJ-plTfNq-8Hot792DPmpurrzcX39v19bfVxfm6NUzS2nYUY-Z66AcLwmCQXHa077GEYfDed8ZQKw33nkhhiOEAHHrHtBHMcdLTs2Z1xNqkd2rOYdL5oJIO6j6Q8kbpXIMZnRKDl5ZTsFze_avvPQfhBMNDD76DbmF9ObLm_TA5a1ysWY_PoM8zMWzVJt2qhYE74Avg4wMgp997V6rapX2Oy_mKMEKYYETQpQofq0xOpWTnHydgUHdyq__kXno-PF3tseOfvvQv8oWpJA</recordid><startdate>20200706</startdate><enddate>20200706</enddate><creator>Kim, Jeong Yoon</creator><creator>Wang, Yan</creator><creator>Li, Zuo Peng</creator><creator>Baiseitova, Aizhamal</creator><creator>Ban, Yeong Jun</creator><creator>Park, Ki Hun</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0003-2817-1648</orcidid><orcidid>https://orcid.org/0000-0002-1549-8978</orcidid></search><sort><creationdate>20200706</creationdate><title>Xanthine Oxidase Inhibition and Anti-LDL Oxidation by Prenylated Isoflavones from Flemingia philippinensis Root</title><author>Kim, Jeong Yoon ; Wang, Yan ; Li, Zuo Peng ; Baiseitova, Aizhamal ; Ban, Yeong Jun ; Park, Ki Hun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-63114e808bd07c109596388190bbfff6cc3d9c5ff297c2c500508e4ac74e5283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>anti-LDL oxidation</topic><topic>Antioxidants</topic><topic>Atherosclerosis</topic><topic>Bone density</topic><topic>Catechol</topic><topic>Chromatography, Liquid</topic><topic>Copper - chemistry</topic><topic>Copper compounds</topic><topic>Electrophoretic mobility</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzymes</topic><topic>Fabaceae - chemistry</topic><topic>Flemingia philippinensis</topic><topic>Fluorescence</topic><topic>Genistein</topic><topic>Inhibitory Concentration 50</topic><topic>Isoflavones</topic><topic>Isoflavones - analysis</topic><topic>Isoflavones - chemistry</topic><topic>Isoflavones - isolation & purification</topic><topic>Isoflavones - pharmacology</topic><topic>Kinetics</topic><topic>Lag time</topic><topic>Legumes</topic><topic>Lipoproteins, LDL - metabolism</topic><topic>Low density lipoprotein</topic><topic>Mass Spectrometry</topic><topic>Metabolites</topic><topic>Oxidants</topic><topic>Oxidation</topic><topic>Oxidation effects</topic><topic>Oxidation-Reduction</topic><topic>Oxidative stress</topic><topic>Oxidizing agents</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Roots - chemistry</topic><topic>prenylated isoflavones</topic><topic>Prenylation</topic><topic>Thiobarbiturates - chemistry</topic><topic>Thiobarbituric acid</topic><topic>Uric acid</topic><topic>Xanthine oxidase</topic><topic>Xanthine Oxidase - antagonists & inhibitors</topic><topic>Xanthine Oxidase - metabolism</topic><topic>xanthine oxidase inhibition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Jeong Yoon</creatorcontrib><creatorcontrib>Wang, Yan</creatorcontrib><creatorcontrib>Li, Zuo Peng</creatorcontrib><creatorcontrib>Baiseitova, Aizhamal</creatorcontrib><creatorcontrib>Ban, Yeong Jun</creatorcontrib><creatorcontrib>Park, Ki Hun</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Jeong Yoon</au><au>Wang, Yan</au><au>Li, Zuo Peng</au><au>Baiseitova, Aizhamal</au><au>Ban, Yeong Jun</au><au>Park, Ki Hun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Xanthine Oxidase Inhibition and Anti-LDL Oxidation by Prenylated Isoflavones from Flemingia philippinensis Root</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2020-07-06</date><risdate>2020</risdate><volume>25</volume><issue>13</issue><spage>3074</spage><pages>3074-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Xanthine oxidase is a frontier enzyme to produce oxidants, which leads to inflammation in the blood. Prenylated isoflavones from
were found to display potent inhibition against xanthine oxidase (XO). All isolates (
-
) inhibited XO enzyme with IC
ranging 7.8~36.4 μM. The most active isoflavones (
-
, IC
= 7.8~14.8 μM) have the structural feature of a catechol motif in B-ring. Inhibitory behaviors were disclosed as a mixed type I mode of inhibition with
<
. Binding affinities to XO enzyme were evaluated. Fluorescence quenching effects agreed with inhibitory potencies (IC
s). The compounds (
-
) also showed potent anti-LDL oxidation effects in the thiobarbituric acid-reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. The compound
protected LDL oxidation with 0.7 μM in TBARS assay, which was 40-fold more active than genistein (IC
= 30.4 μM).</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>32640700</pmid><doi>10.3390/molecules25133074</doi><orcidid>https://orcid.org/0000-0003-2817-1648</orcidid><orcidid>https://orcid.org/0000-0002-1549-8978</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | anti-LDL oxidation Antioxidants Atherosclerosis Bone density Catechol Chromatography, Liquid Copper - chemistry Copper compounds Electrophoretic mobility Enzyme Inhibitors - chemistry Enzymes Fabaceae - chemistry Flemingia philippinensis Fluorescence Genistein Inhibitory Concentration 50 Isoflavones Isoflavones - analysis Isoflavones - chemistry Isoflavones - isolation & purification Isoflavones - pharmacology Kinetics Lag time Legumes Lipoproteins, LDL - metabolism Low density lipoprotein Mass Spectrometry Metabolites Oxidants Oxidation Oxidation effects Oxidation-Reduction Oxidative stress Oxidizing agents Plant Extracts - chemistry Plant Extracts - pharmacology Plant Roots - chemistry prenylated isoflavones Prenylation Thiobarbiturates - chemistry Thiobarbituric acid Uric acid Xanthine oxidase Xanthine Oxidase - antagonists & inhibitors Xanthine Oxidase - metabolism xanthine oxidase inhibition |
| title | Xanthine Oxidase Inhibition and Anti-LDL Oxidation by Prenylated Isoflavones from Flemingia philippinensis Root |
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