Loading…

Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells

Sesamin, a representative sesame lignan, has health-promoting activities. Sesamin is converted into catechol derivatives and further into their glucuronides or sulfates in vivo, whereas the biological activities of sesamin metabolites remain unclear. We examined the inhibitory effects of sesamin met...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 2019-07, Vol.67 (27), p.7640-7649
Main Authors: Abe-Kanoh, Naomi, Kunimoto, Yumi, Takemoto, Daisuke, Ono, Yoshiko, Shibata, Hiroshi, Ohnishi, Kohta, Kawai, Yoshichika
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953
cites cdi_FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953
container_end_page 7649
container_issue 27
container_start_page 7640
container_title Journal of agricultural and food chemistry
container_volume 67
creator Abe-Kanoh, Naomi
Kunimoto, Yumi
Takemoto, Daisuke
Ono, Yoshiko
Shibata, Hiroshi
Ohnishi, Kohta
Kawai, Yoshichika
description Sesamin, a representative sesame lignan, has health-promoting activities. Sesamin is converted into catechol derivatives and further into their glucuronides or sulfates in vivo, whereas the biological activities of sesamin metabolites remain unclear. We examined the inhibitory effects of sesamin metabolites on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage-like J774.1 cells and found that a monocatechol derivative SC1, (7α,7′α,8α,8′α)-3,4-dihydroxy-3′,4′-methylenedioxy-7,9′:7′,9-diepoxylignane, has a much higher activity than sesamin and other metabolites. The inhibitory effects of SC1 glucuronides were time-dependently enhanced, associated with the intracellular accumulation of SC1 and the methylated form. SC1 glucuronides and SC1 attenuated the expression of inducible NO synthase (iNOS) and upstream interferon-β (IFN-β) in the LPS-stimulated macrophages. The inhibitory effects of SC1 glucuronides against NO production were canceled by the β-glucuronidase inhibitor and enhanced by the catechol-O-methyltransferase inhibitor. Our results suggest that SC1 glucuronides exert the anti-inflammatory effects by inhibiting the IFN-β/iNOS signaling through macrophage-mediated deconjugation.
doi_str_mv 10.1021/acs.jafc.8b07227
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2204693859</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2204693859</sourcerecordid><originalsourceid>FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953</originalsourceid><addsrcrecordid>eNp1kc2O0zAUhS0EYjoDe1bISxak2ElcO8tRKcOggVkU1pFjXzcuiRP8I01fixeYN-CZcGlhx8rS1fmOz70HoVeULCkp6TupwnIvjVqKjvCy5E_QgrKSFIxS8RQtSNYUgq3oBboMYU8IEYyT5-iiIg2jFSUL9LiFIEfr8FpGUP004JshqeQnZzUEvHkAH_G1i7awzgxyHGWc_AFvjAEVA-4OeJvm2UMI1u3wrYvgDWQa__qJpdN5opOy3QD4i43eKnz_kI3x9uBiLwPkD05wJmLvp7Tr8XtQk9unnYzHaY72WSo_zb3cQTHY74A_cV4vKV7DMIQX6JmRQ4CX5_cKffuw-br-WNzd39yur-8KWZMyFlxLke_DG00ll6apgRqtOsGpaoCB7jqtGRFGi6rjTQWspistq0qwfLOqYdUVenPynf30I0GI7WiDygmkgymFtixJvWqyvslScpLm1CF4MO3s7Sj9oaWkPdbW5traY23tubaMvD67p24E_Q_421MWvD0J_qBT8i4v-3-_39iRqE4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2204693859</pqid></control><display><type>article</type><title>Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Abe-Kanoh, Naomi ; Kunimoto, Yumi ; Takemoto, Daisuke ; Ono, Yoshiko ; Shibata, Hiroshi ; Ohnishi, Kohta ; Kawai, Yoshichika</creator><creatorcontrib>Abe-Kanoh, Naomi ; Kunimoto, Yumi ; Takemoto, Daisuke ; Ono, Yoshiko ; Shibata, Hiroshi ; Ohnishi, Kohta ; Kawai, Yoshichika</creatorcontrib><description>Sesamin, a representative sesame lignan, has health-promoting activities. Sesamin is converted into catechol derivatives and further into their glucuronides or sulfates in vivo, whereas the biological activities of sesamin metabolites remain unclear. We examined the inhibitory effects of sesamin metabolites on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage-like J774.1 cells and found that a monocatechol derivative SC1, (7α,7′α,8α,8′α)-3,4-dihydroxy-3′,4′-methylenedioxy-7,9′:7′,9-diepoxylignane, has a much higher activity than sesamin and other metabolites. The inhibitory effects of SC1 glucuronides were time-dependently enhanced, associated with the intracellular accumulation of SC1 and the methylated form. SC1 glucuronides and SC1 attenuated the expression of inducible NO synthase (iNOS) and upstream interferon-β (IFN-β) in the LPS-stimulated macrophages. The inhibitory effects of SC1 glucuronides against NO production were canceled by the β-glucuronidase inhibitor and enhanced by the catechol-O-methyltransferase inhibitor. Our results suggest that SC1 glucuronides exert the anti-inflammatory effects by inhibiting the IFN-β/iNOS signaling through macrophage-mediated deconjugation.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.8b07227</identifier><identifier>PMID: 30951310</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of agricultural and food chemistry, 2019-07, Vol.67 (27), p.7640-7649</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953</citedby><cites>FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953</cites><orcidid>0000-0002-5091-9133</orcidid></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/30951310$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abe-Kanoh, Naomi</creatorcontrib><creatorcontrib>Kunimoto, Yumi</creatorcontrib><creatorcontrib>Takemoto, Daisuke</creatorcontrib><creatorcontrib>Ono, Yoshiko</creatorcontrib><creatorcontrib>Shibata, Hiroshi</creatorcontrib><creatorcontrib>Ohnishi, Kohta</creatorcontrib><creatorcontrib>Kawai, Yoshichika</creatorcontrib><title>Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Sesamin, a representative sesame lignan, has health-promoting activities. Sesamin is converted into catechol derivatives and further into their glucuronides or sulfates in vivo, whereas the biological activities of sesamin metabolites remain unclear. We examined the inhibitory effects of sesamin metabolites on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage-like J774.1 cells and found that a monocatechol derivative SC1, (7α,7′α,8α,8′α)-3,4-dihydroxy-3′,4′-methylenedioxy-7,9′:7′,9-diepoxylignane, has a much higher activity than sesamin and other metabolites. The inhibitory effects of SC1 glucuronides were time-dependently enhanced, associated with the intracellular accumulation of SC1 and the methylated form. SC1 glucuronides and SC1 attenuated the expression of inducible NO synthase (iNOS) and upstream interferon-β (IFN-β) in the LPS-stimulated macrophages. The inhibitory effects of SC1 glucuronides against NO production were canceled by the β-glucuronidase inhibitor and enhanced by the catechol-O-methyltransferase inhibitor. Our results suggest that SC1 glucuronides exert the anti-inflammatory effects by inhibiting the IFN-β/iNOS signaling through macrophage-mediated deconjugation.</description><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kc2O0zAUhS0EYjoDe1bISxak2ElcO8tRKcOggVkU1pFjXzcuiRP8I01fixeYN-CZcGlhx8rS1fmOz70HoVeULCkp6TupwnIvjVqKjvCy5E_QgrKSFIxS8RQtSNYUgq3oBboMYU8IEYyT5-iiIg2jFSUL9LiFIEfr8FpGUP004JshqeQnZzUEvHkAH_G1i7awzgxyHGWc_AFvjAEVA-4OeJvm2UMI1u3wrYvgDWQa__qJpdN5opOy3QD4i43eKnz_kI3x9uBiLwPkD05wJmLvp7Tr8XtQk9unnYzHaY72WSo_zb3cQTHY74A_cV4vKV7DMIQX6JmRQ4CX5_cKffuw-br-WNzd39yur-8KWZMyFlxLke_DG00ll6apgRqtOsGpaoCB7jqtGRFGi6rjTQWspistq0qwfLOqYdUVenPynf30I0GI7WiDygmkgymFtixJvWqyvslScpLm1CF4MO3s7Sj9oaWkPdbW5traY23tubaMvD67p24E_Q_421MWvD0J_qBT8i4v-3-_39iRqE4</recordid><startdate>20190710</startdate><enddate>20190710</enddate><creator>Abe-Kanoh, Naomi</creator><creator>Kunimoto, Yumi</creator><creator>Takemoto, Daisuke</creator><creator>Ono, Yoshiko</creator><creator>Shibata, Hiroshi</creator><creator>Ohnishi, Kohta</creator><creator>Kawai, Yoshichika</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5091-9133</orcidid></search><sort><creationdate>20190710</creationdate><title>Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells</title><author>Abe-Kanoh, Naomi ; Kunimoto, Yumi ; Takemoto, Daisuke ; Ono, Yoshiko ; Shibata, Hiroshi ; Ohnishi, Kohta ; Kawai, Yoshichika</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abe-Kanoh, Naomi</creatorcontrib><creatorcontrib>Kunimoto, Yumi</creatorcontrib><creatorcontrib>Takemoto, Daisuke</creatorcontrib><creatorcontrib>Ono, Yoshiko</creatorcontrib><creatorcontrib>Shibata, Hiroshi</creatorcontrib><creatorcontrib>Ohnishi, Kohta</creatorcontrib><creatorcontrib>Kawai, Yoshichika</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abe-Kanoh, Naomi</au><au>Kunimoto, Yumi</au><au>Takemoto, Daisuke</au><au>Ono, Yoshiko</au><au>Shibata, Hiroshi</au><au>Ohnishi, Kohta</au><au>Kawai, Yoshichika</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2019-07-10</date><risdate>2019</risdate><volume>67</volume><issue>27</issue><spage>7640</spage><epage>7649</epage><pages>7640-7649</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>Sesamin, a representative sesame lignan, has health-promoting activities. Sesamin is converted into catechol derivatives and further into their glucuronides or sulfates in vivo, whereas the biological activities of sesamin metabolites remain unclear. We examined the inhibitory effects of sesamin metabolites on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage-like J774.1 cells and found that a monocatechol derivative SC1, (7α,7′α,8α,8′α)-3,4-dihydroxy-3′,4′-methylenedioxy-7,9′:7′,9-diepoxylignane, has a much higher activity than sesamin and other metabolites. The inhibitory effects of SC1 glucuronides were time-dependently enhanced, associated with the intracellular accumulation of SC1 and the methylated form. SC1 glucuronides and SC1 attenuated the expression of inducible NO synthase (iNOS) and upstream interferon-β (IFN-β) in the LPS-stimulated macrophages. The inhibitory effects of SC1 glucuronides against NO production were canceled by the β-glucuronidase inhibitor and enhanced by the catechol-O-methyltransferase inhibitor. Our results suggest that SC1 glucuronides exert the anti-inflammatory effects by inhibiting the IFN-β/iNOS signaling through macrophage-mediated deconjugation.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>30951310</pmid><doi>10.1021/acs.jafc.8b07227</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-5091-9133</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0021-8561
ispartof Journal of agricultural and food chemistry, 2019-07, Vol.67 (27), p.7640-7649
issn 0021-8561
1520-5118
language eng
recordid cdi_proquest_miscellaneous_2204693859
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T17%3A41%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sesamin%20Catechol%20Glucuronides%20Exert%20Anti-inflammatory%20Effects%20by%20Suppressing%20Interferon%20%CE%B2%20and%20Inducible%20Nitric%20Oxide%20Synthase%20Expression%20through%20Deconjugation%20in%20Macrophage-like%20J774.1%20Cells&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Abe-Kanoh,%20Naomi&rft.date=2019-07-10&rft.volume=67&rft.issue=27&rft.spage=7640&rft.epage=7649&rft.pages=7640-7649&rft.issn=0021-8561&rft.eissn=1520-5118&rft_id=info:doi/10.1021/acs.jafc.8b07227&rft_dat=%3Cproquest_cross%3E2204693859%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a402t-7da822779d1a7af94e1fdcb871c9e5edbbdd508fd83b793e5416da33850083953%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2204693859&rft_id=info:pmid/30951310&rfr_iscdi=true