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Antioxidant capacity of 12 major soybean isoflavones and their bioavailability under simulated digestion and in human intestinal Caco-2 cells
[Display omitted] •Acetyl conjugate of isoflavones in the intestinal digestion had the lowest stability.•Isoflavone aglycones had the highest permeability and cellular accumulation.•Glycitein had the lowest permeability and cellular accumulation among 12 isoflavones.•Caco-2 cells can use acetyl and...
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Published in: | Food chemistry 2022-04, Vol.374, p.131493, Article 131493 |
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creator | Kim, Mi-Seon Jung, Young Sung Jang, Davin Cho, Chi Heung Lee, Sang-Hoon Han, Nam Soo Kim, Dae-Ok |
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•Acetyl conjugate of isoflavones in the intestinal digestion had the lowest stability.•Isoflavone aglycones had the highest permeability and cellular accumulation.•Glycitein had the lowest permeability and cellular accumulation among 12 isoflavones.•Caco-2 cells can use acetyl and malonyl conjugates of isoflavones in intact form.
Soy isoflavones (SIs) show various health benefits, such as antioxidant and estrogenic effects. It is important to understand the bioaccessibility and bioavailability of SIs due to the close relation to their bioactivities. In this study, the antioxidant capacity, bioaccessibility, and bioavailability of 12 SIs were evaluated using radical-scavenging methods, simulations of human digestion, and Caco-2 cells in Transwell, respectively. All SIs were stable (91.1–99.2%) under gastric digestion conditions compared with the control (100%), whereas acetyl and malonyl conjugates were unstable (38.5% and 65.5%, respectively) under small intestinal digestion conditions. SI aglycones showed higher permeability (7–15 times) and cellular accumulation (8.8 times) than their glucosides. A small amount of SI conjugates was intact in the cell and in the basolateral side of each Transwell. These results suggest that SI conjugates, especially malonyl and acetyl forms, have incidental bioactivity after being metabolized to aglycones inside the cell. |
doi_str_mv | 10.1016/j.foodchem.2021.131493 |
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•Acetyl conjugate of isoflavones in the intestinal digestion had the lowest stability.•Isoflavone aglycones had the highest permeability and cellular accumulation.•Glycitein had the lowest permeability and cellular accumulation among 12 isoflavones.•Caco-2 cells can use acetyl and malonyl conjugates of isoflavones in intact form.
Soy isoflavones (SIs) show various health benefits, such as antioxidant and estrogenic effects. It is important to understand the bioaccessibility and bioavailability of SIs due to the close relation to their bioactivities. In this study, the antioxidant capacity, bioaccessibility, and bioavailability of 12 SIs were evaluated using radical-scavenging methods, simulations of human digestion, and Caco-2 cells in Transwell, respectively. All SIs were stable (91.1–99.2%) under gastric digestion conditions compared with the control (100%), whereas acetyl and malonyl conjugates were unstable (38.5% and 65.5%, respectively) under small intestinal digestion conditions. SI aglycones showed higher permeability (7–15 times) and cellular accumulation (8.8 times) than their glucosides. A small amount of SI conjugates was intact in the cell and in the basolateral side of each Transwell. These results suggest that SI conjugates, especially malonyl and acetyl forms, have incidental bioactivity after being metabolized to aglycones inside the cell.</description><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2021.131493</identifier><identifier>PMID: 34802809</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antioxidants ; Bioaccessibility ; Biological Availability ; Caco-2 Cells ; Cellular accumulation ; Digestion ; Digestion stability ; Glycine max ; Humans ; Isoflavone conjugate ; Isoflavones ; Permeability ; Transwell system</subject><ispartof>Food chemistry, 2022-04, Vol.374, p.131493, Article 131493</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-46372d88d3154d7735e950c620e9932c8f2d18e75ed815a790f967b200add5283</citedby><cites>FETCH-LOGICAL-c368t-46372d88d3154d7735e950c620e9932c8f2d18e75ed815a790f967b200add5283</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34802809$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Mi-Seon</creatorcontrib><creatorcontrib>Jung, Young Sung</creatorcontrib><creatorcontrib>Jang, Davin</creatorcontrib><creatorcontrib>Cho, Chi Heung</creatorcontrib><creatorcontrib>Lee, Sang-Hoon</creatorcontrib><creatorcontrib>Han, Nam Soo</creatorcontrib><creatorcontrib>Kim, Dae-Ok</creatorcontrib><title>Antioxidant capacity of 12 major soybean isoflavones and their bioavailability under simulated digestion and in human intestinal Caco-2 cells</title><title>Food chemistry</title><addtitle>Food Chem</addtitle><description>[Display omitted]
•Acetyl conjugate of isoflavones in the intestinal digestion had the lowest stability.•Isoflavone aglycones had the highest permeability and cellular accumulation.•Glycitein had the lowest permeability and cellular accumulation among 12 isoflavones.•Caco-2 cells can use acetyl and malonyl conjugates of isoflavones in intact form.
Soy isoflavones (SIs) show various health benefits, such as antioxidant and estrogenic effects. It is important to understand the bioaccessibility and bioavailability of SIs due to the close relation to their bioactivities. In this study, the antioxidant capacity, bioaccessibility, and bioavailability of 12 SIs were evaluated using radical-scavenging methods, simulations of human digestion, and Caco-2 cells in Transwell, respectively. All SIs were stable (91.1–99.2%) under gastric digestion conditions compared with the control (100%), whereas acetyl and malonyl conjugates were unstable (38.5% and 65.5%, respectively) under small intestinal digestion conditions. SI aglycones showed higher permeability (7–15 times) and cellular accumulation (8.8 times) than their glucosides. A small amount of SI conjugates was intact in the cell and in the basolateral side of each Transwell. These results suggest that SI conjugates, especially malonyl and acetyl forms, have incidental bioactivity after being metabolized to aglycones inside the cell.</description><subject>Antioxidants</subject><subject>Bioaccessibility</subject><subject>Biological Availability</subject><subject>Caco-2 Cells</subject><subject>Cellular accumulation</subject><subject>Digestion</subject><subject>Digestion stability</subject><subject>Glycine max</subject><subject>Humans</subject><subject>Isoflavone conjugate</subject><subject>Isoflavones</subject><subject>Permeability</subject><subject>Transwell system</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkEFu2zAQRYmiQeO4vULAC8gdkpJI7RoYbVogQDbJmhiRo5qGRBqibNSHyJ0j1U23WQ0wmPf_4DF2K2AjQNRf95suJe92NGwkSLERSpSN-sBWwmhVaNDyI1uBAlMYUdbX7CbnPQBIEOYTu1alAWmgWbGXuziF9Cd4jBN3eEAXpjNPHReSD7hPI8_p3BJGHnLqejylSJlj9HzaURh5GxKeMPTYhn4hj9HTzITh2ONEnvvwm_LcEP8yIfLdcVjC4rSsI_Z8iy4Vkjvq-_yZXXXYZ_ryb67Z84_vT9ufxcPj_a_t3UPhVG2moqyVlt4Yr0RVeq1VRU0FrpZATaOkM530wpCuyBtRoW6ga2rdSgD0vpJGrVl9yXVjynmkzh7GMOB4tgLs4tfu7Ztfu_i1F78zeHsBD8d2IP8fexM6H3y7HND8_inQaLMLFB35MJKbrE_hvY5XBbmRNQ</recordid><startdate>20220416</startdate><enddate>20220416</enddate><creator>Kim, Mi-Seon</creator><creator>Jung, Young Sung</creator><creator>Jang, Davin</creator><creator>Cho, Chi Heung</creator><creator>Lee, Sang-Hoon</creator><creator>Han, Nam Soo</creator><creator>Kim, Dae-Ok</creator><general>Elsevier Ltd</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></search><sort><creationdate>20220416</creationdate><title>Antioxidant capacity of 12 major soybean isoflavones and their bioavailability under simulated digestion and in human intestinal Caco-2 cells</title><author>Kim, Mi-Seon ; Jung, Young Sung ; Jang, Davin ; Cho, Chi Heung ; Lee, Sang-Hoon ; Han, Nam Soo ; Kim, Dae-Ok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-46372d88d3154d7735e950c620e9932c8f2d18e75ed815a790f967b200add5283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Antioxidants</topic><topic>Bioaccessibility</topic><topic>Biological Availability</topic><topic>Caco-2 Cells</topic><topic>Cellular accumulation</topic><topic>Digestion</topic><topic>Digestion stability</topic><topic>Glycine max</topic><topic>Humans</topic><topic>Isoflavone conjugate</topic><topic>Isoflavones</topic><topic>Permeability</topic><topic>Transwell system</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Mi-Seon</creatorcontrib><creatorcontrib>Jung, Young Sung</creatorcontrib><creatorcontrib>Jang, Davin</creatorcontrib><creatorcontrib>Cho, Chi Heung</creatorcontrib><creatorcontrib>Lee, Sang-Hoon</creatorcontrib><creatorcontrib>Han, Nam Soo</creatorcontrib><creatorcontrib>Kim, Dae-Ok</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Mi-Seon</au><au>Jung, Young Sung</au><au>Jang, Davin</au><au>Cho, Chi Heung</au><au>Lee, Sang-Hoon</au><au>Han, Nam Soo</au><au>Kim, Dae-Ok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant capacity of 12 major soybean isoflavones and their bioavailability under simulated digestion and in human intestinal Caco-2 cells</atitle><jtitle>Food chemistry</jtitle><addtitle>Food Chem</addtitle><date>2022-04-16</date><risdate>2022</risdate><volume>374</volume><spage>131493</spage><pages>131493-</pages><artnum>131493</artnum><issn>0308-8146</issn><eissn>1873-7072</eissn><abstract>[Display omitted]
•Acetyl conjugate of isoflavones in the intestinal digestion had the lowest stability.•Isoflavone aglycones had the highest permeability and cellular accumulation.•Glycitein had the lowest permeability and cellular accumulation among 12 isoflavones.•Caco-2 cells can use acetyl and malonyl conjugates of isoflavones in intact form.
Soy isoflavones (SIs) show various health benefits, such as antioxidant and estrogenic effects. It is important to understand the bioaccessibility and bioavailability of SIs due to the close relation to their bioactivities. In this study, the antioxidant capacity, bioaccessibility, and bioavailability of 12 SIs were evaluated using radical-scavenging methods, simulations of human digestion, and Caco-2 cells in Transwell, respectively. All SIs were stable (91.1–99.2%) under gastric digestion conditions compared with the control (100%), whereas acetyl and malonyl conjugates were unstable (38.5% and 65.5%, respectively) under small intestinal digestion conditions. SI aglycones showed higher permeability (7–15 times) and cellular accumulation (8.8 times) than their glucosides. A small amount of SI conjugates was intact in the cell and in the basolateral side of each Transwell. These results suggest that SI conjugates, especially malonyl and acetyl forms, have incidental bioactivity after being metabolized to aglycones inside the cell.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>34802809</pmid><doi>10.1016/j.foodchem.2021.131493</doi></addata></record> |
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subjects | Antioxidants Bioaccessibility Biological Availability Caco-2 Cells Cellular accumulation Digestion Digestion stability Glycine max Humans Isoflavone conjugate Isoflavones Permeability Transwell system |
title | Antioxidant capacity of 12 major soybean isoflavones and their bioavailability under simulated digestion and in human intestinal Caco-2 cells |
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