Metabolic stability and inhibitory effect of O-methylated theaflavins on H2O2-induced oxidative damage in human HepG2 cells
Seven new O-methylated theaflavins (TFs) were synthesized by using O-methyltransferase from an edible mushroom. Using TFs and O-methylated TFs, metabolic stability in pooled human liver S9 fractions and inhibitory effect on H 2 O 2 -induced oxidative damage in human HepG2 cells were investigated. In...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2014, Vol.78 (7), p.1140-1146 |
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| container_issue | 7 |
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| container_title | Bioscience, biotechnology, and biochemistry |
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| creator | Tanaka, Yoshihisa Kirita, Masanobu Abe, Yuko Miyata, Satoshi Tagashira, Motoyuki Kanda, Tomomasa Maeda-Yamamoto, Mari |
| description | Seven new O-methylated theaflavins (TFs) were synthesized by using O-methyltransferase from an edible mushroom. Using TFs and O-methylated TFs, metabolic stability in pooled human liver S9 fractions and inhibitory effect on H
2
O
2
-induced oxidative damage in human HepG2 cells were investigated. In O-methylation of theaflavin 3′-O-gallate (TF3′G), metabolic stability was potentiated by an increase in the number of introduced methyl groups. O-methylation of TF3,3′G did not affect metabolic stability, which was likely because of a remaining 3-O-galloyl group. The inhibitory effect on oxidative damage was assessed by measuring the viability of H
2
O
2
-damaged HepG2 cells treated with TFs and O-methylated TFs. TF3,3′G and O-methylated TFs increased cell viabilities significantly compared with DMSO, which was the compound vehicle (p |
| doi_str_mv | 10.1080/09168451.2014.917268 |
| format | Article |
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2
O
2
-induced oxidative damage in human HepG2 cells were investigated. In O-methylation of theaflavin 3′-O-gallate (TF3′G), metabolic stability was potentiated by an increase in the number of introduced methyl groups. O-methylation of TF3,3′G did not affect metabolic stability, which was likely because of a remaining 3-O-galloyl group. The inhibitory effect on oxidative damage was assessed by measuring the viability of H
2
O
2
-damaged HepG2 cells treated with TFs and O-methylated TFs. TF3,3′G and O-methylated TFs increased cell viabilities significantly compared with DMSO, which was the compound vehicle (p < 0.05), and improved to approximately 100%. Only TF3′G did not significantly increase cell viability. It was suggested that the inhibitory effect on H
2
O
2
-induced oxidative damage was potentiated by O-methylation or O-galloylation of TFs.
Seven new O-methylated theaflavins (3-9) were synthesized. Metabolic stability and inhibitory effect of O-methylated theaflavins on H
2
O
2
-induced oxidative damage in human HepG2 cells were investigated.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1080/09168451.2014.917268</identifier><identifier>PMID: 25229848</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>Biflavonoids - chemical synthesis ; Biflavonoids - chemistry ; Biflavonoids - metabolism ; Biflavonoids - pharmacology ; black tea ; Catechin - chemical synthesis ; Catechin - chemistry ; Catechin - metabolism ; Catechin - pharmacology ; Drug Stability ; Hep G2 Cells ; Humans ; Hydrogen Peroxide - pharmacology ; metabolic stability ; Methylation ; O-methylated theaflavin ; oxidative damage ; Oxidative Stress - drug effects ; Oxygen - chemistry ; polyphenol</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2014, Vol.78 (7), p.1140-1146</ispartof><rights>2014 Japan Society for Bioscience, Biotechnology, and Agrochemistry 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c449t-688d7cb7c8353a3d57738710436072b67db2736e8b193f9afc5e9e40e4f6f28b3</citedby><cites>FETCH-LOGICAL-c449t-688d7cb7c8353a3d57738710436072b67db2736e8b193f9afc5e9e40e4f6f28b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25229848$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tanaka, Yoshihisa</creatorcontrib><creatorcontrib>Kirita, Masanobu</creatorcontrib><creatorcontrib>Abe, Yuko</creatorcontrib><creatorcontrib>Miyata, Satoshi</creatorcontrib><creatorcontrib>Tagashira, Motoyuki</creatorcontrib><creatorcontrib>Kanda, Tomomasa</creatorcontrib><creatorcontrib>Maeda-Yamamoto, Mari</creatorcontrib><title>Metabolic stability and inhibitory effect of O-methylated theaflavins on H2O2-induced oxidative damage in human HepG2 cells</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>Seven new O-methylated theaflavins (TFs) were synthesized by using O-methyltransferase from an edible mushroom. Using TFs and O-methylated TFs, metabolic stability in pooled human liver S9 fractions and inhibitory effect on H
2
O
2
-induced oxidative damage in human HepG2 cells were investigated. In O-methylation of theaflavin 3′-O-gallate (TF3′G), metabolic stability was potentiated by an increase in the number of introduced methyl groups. O-methylation of TF3,3′G did not affect metabolic stability, which was likely because of a remaining 3-O-galloyl group. The inhibitory effect on oxidative damage was assessed by measuring the viability of H
2
O
2
-damaged HepG2 cells treated with TFs and O-methylated TFs. TF3,3′G and O-methylated TFs increased cell viabilities significantly compared with DMSO, which was the compound vehicle (p < 0.05), and improved to approximately 100%. Only TF3′G did not significantly increase cell viability. It was suggested that the inhibitory effect on H
2
O
2
-induced oxidative damage was potentiated by O-methylation or O-galloylation of TFs.
Seven new O-methylated theaflavins (3-9) were synthesized. Metabolic stability and inhibitory effect of O-methylated theaflavins on H
2
O
2
-induced oxidative damage in human HepG2 cells were investigated.</description><subject>Biflavonoids - chemical synthesis</subject><subject>Biflavonoids - chemistry</subject><subject>Biflavonoids - metabolism</subject><subject>Biflavonoids - pharmacology</subject><subject>black tea</subject><subject>Catechin - chemical synthesis</subject><subject>Catechin - chemistry</subject><subject>Catechin - metabolism</subject><subject>Catechin - pharmacology</subject><subject>Drug Stability</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Hydrogen Peroxide - pharmacology</subject><subject>metabolic stability</subject><subject>Methylation</subject><subject>O-methylated theaflavin</subject><subject>oxidative damage</subject><subject>Oxidative Stress - drug effects</subject><subject>Oxygen - chemistry</subject><subject>polyphenol</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkM1u1DAURi0EokPLGyDkJZtM_ZfYWSFUQYvUajZ0bTn2NWOUxIPtFCJenkRpWaKufOV7vs_WQegdJXtKFLkkLW2UqOmeESr2LZWsUS_QjnIhq6YV8iXarUi1MmfoTc4_CFkuavoanbGasVYJtUN_7qCYLvbB4rwMoQ9lxmZ0OIzH0IUS04zBe7AFR48P1QDlOPemgMPlCMb35iGMGccR37ADq8LoJrvs4u_gTAkPgJ0ZzHdY6vBxGsyCwemaYQt9ny_QK2_6DG8fz3N0_-Xzt6ub6vZw_fXq021lhWhL1SjlpO2kVbzmhrtaSq4kJYI3RLKuka5jkjegOtpy3xpva2hBEBC-8Ux1_Bx92HpPKf6cIBc9hLz-wIwQp6xp3fBWMSXVgooNtSnmnMDrUwqDSbOmRK_a9ZN2vWrXm_Yl9v7xhakbwP0LPXlegMsNiNPpuZUft0QYfUyD-RVT73Qxcx-TT2a0IWv-34a_JpWfCA</recordid><startdate>2014</startdate><enddate>2014</enddate><creator>Tanaka, Yoshihisa</creator><creator>Kirita, Masanobu</creator><creator>Abe, Yuko</creator><creator>Miyata, Satoshi</creator><creator>Tagashira, Motoyuki</creator><creator>Kanda, Tomomasa</creator><creator>Maeda-Yamamoto, Mari</creator><general>Taylor & Francis</general><general>Oxford University Press</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>7X8</scope></search><sort><creationdate>2014</creationdate><title>Metabolic stability and inhibitory effect of O-methylated theaflavins on H2O2-induced oxidative damage in human HepG2 cells</title><author>Tanaka, Yoshihisa ; Kirita, Masanobu ; Abe, Yuko ; Miyata, Satoshi ; Tagashira, Motoyuki ; Kanda, Tomomasa ; Maeda-Yamamoto, Mari</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c449t-688d7cb7c8353a3d57738710436072b67db2736e8b193f9afc5e9e40e4f6f28b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Biflavonoids - chemical synthesis</topic><topic>Biflavonoids - chemistry</topic><topic>Biflavonoids - metabolism</topic><topic>Biflavonoids - pharmacology</topic><topic>black tea</topic><topic>Catechin - chemical synthesis</topic><topic>Catechin - chemistry</topic><topic>Catechin - metabolism</topic><topic>Catechin - pharmacology</topic><topic>Drug Stability</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Hydrogen Peroxide - pharmacology</topic><topic>metabolic stability</topic><topic>Methylation</topic><topic>O-methylated theaflavin</topic><topic>oxidative damage</topic><topic>Oxidative Stress - drug effects</topic><topic>Oxygen - chemistry</topic><topic>polyphenol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tanaka, Yoshihisa</creatorcontrib><creatorcontrib>Kirita, Masanobu</creatorcontrib><creatorcontrib>Abe, Yuko</creatorcontrib><creatorcontrib>Miyata, Satoshi</creatorcontrib><creatorcontrib>Tagashira, Motoyuki</creatorcontrib><creatorcontrib>Kanda, Tomomasa</creatorcontrib><creatorcontrib>Maeda-Yamamoto, Mari</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tanaka, Yoshihisa</au><au>Kirita, Masanobu</au><au>Abe, Yuko</au><au>Miyata, Satoshi</au><au>Tagashira, Motoyuki</au><au>Kanda, Tomomasa</au><au>Maeda-Yamamoto, Mari</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metabolic stability and inhibitory effect of O-methylated theaflavins on H2O2-induced oxidative damage in human HepG2 cells</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2014</date><risdate>2014</risdate><volume>78</volume><issue>7</issue><spage>1140</spage><epage>1146</epage><pages>1140-1146</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>Seven new O-methylated theaflavins (TFs) were synthesized by using O-methyltransferase from an edible mushroom. Using TFs and O-methylated TFs, metabolic stability in pooled human liver S9 fractions and inhibitory effect on H
2
O
2
-induced oxidative damage in human HepG2 cells were investigated. In O-methylation of theaflavin 3′-O-gallate (TF3′G), metabolic stability was potentiated by an increase in the number of introduced methyl groups. O-methylation of TF3,3′G did not affect metabolic stability, which was likely because of a remaining 3-O-galloyl group. The inhibitory effect on oxidative damage was assessed by measuring the viability of H
2
O
2
-damaged HepG2 cells treated with TFs and O-methylated TFs. TF3,3′G and O-methylated TFs increased cell viabilities significantly compared with DMSO, which was the compound vehicle (p < 0.05), and improved to approximately 100%. Only TF3′G did not significantly increase cell viability. It was suggested that the inhibitory effect on H
2
O
2
-induced oxidative damage was potentiated by O-methylation or O-galloylation of TFs.
Seven new O-methylated theaflavins (3-9) were synthesized. Metabolic stability and inhibitory effect of O-methylated theaflavins on H
2
O
2
-induced oxidative damage in human HepG2 cells were investigated.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>25229848</pmid><doi>10.1080/09168451.2014.917268</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2014, Vol.78 (7), p.1140-1146 |
| issn | 0916-8451 1347-6947 |
| language | eng |
| recordid | cdi_pubmed_primary_25229848 |
| source | MEDLINE; Oxford University Press Journals All Titles (1996-Current); Freely Accessible Japanese Titles; EZB-FREE-00999 freely available EZB journals |
| subjects | Biflavonoids - chemical synthesis Biflavonoids - chemistry Biflavonoids - metabolism Biflavonoids - pharmacology black tea Catechin - chemical synthesis Catechin - chemistry Catechin - metabolism Catechin - pharmacology Drug Stability Hep G2 Cells Humans Hydrogen Peroxide - pharmacology metabolic stability Methylation O-methylated theaflavin oxidative damage Oxidative Stress - drug effects Oxygen - chemistry polyphenol |
| title | Metabolic stability and inhibitory effect of O-methylated theaflavins on H2O2-induced oxidative damage in human HepG2 cells |
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