Glucosyloxybenzyl Eucomate Derivatives from Vanda teres Stimulate HaCaT Cytochrome c Oxidase
Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratin...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2011-05, Vol.74 (5), p.949-955 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Simmler, Charlotte Antheaume, Cyril André, Patrice Bonté, Frédéric Lobstein, Annelise |
| description | Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect on cytochrome c oxidase activity, implicated in mitochondrial respiratory function and cellular energy production. Eucomic acid (1) and vandateroside II (3) increased cytochrome c oxidase activity and/or expression, without enhancing cellular mitochondrial content. These two V. teres biomarkers apparently contributed to stimulate respiratory functions in keratinocytes. Since aging and its pathologies may be ascribed to a decline in mitochondrial functions, these biomarkers have the potential to become new natural ingredients for antiaging preparations to remedy age-related disorders such as skin aging. |
| doi_str_mv | 10.1021/np1006636 |
| format | Article |
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Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect on cytochrome c oxidase activity, implicated in mitochondrial respiratory function and cellular energy production. Eucomic acid (1) and vandateroside II (3) increased cytochrome c oxidase activity and/or expression, without enhancing cellular mitochondrial content. These two V. teres biomarkers apparently contributed to stimulate respiratory functions in keratinocytes. Since aging and its pathologies may be ascribed to a decline in mitochondrial functions, these biomarkers have the potential to become new natural ingredients for antiaging preparations to remedy age-related disorders such as skin aging.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np1006636</identifier><identifier>PMID: 21510636</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Biological and medical sciences ; Electron Transport Complex IV - drug effects ; Electron Transport Complex IV - metabolism ; General pharmacology ; Glucosides - chemistry ; Glucosides - isolation & purification ; Glucosides - pharmacology ; Humans ; Iridoid Glucosides - chemistry ; Iridoid Glucosides - isolation & purification ; Iridoid Glucosides - pharmacology ; Keratinocytes - drug effects ; Malates - chemistry ; Malates - isolation & purification ; Malates - pharmacology ; Medical sciences ; Mitochondria - metabolism ; Molecular Structure ; Orchidaceae - chemistry ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Stems - chemistry ; Thailand</subject><ispartof>Journal of natural products (Washington, D.C.), 2011-05, Vol.74 (5), p.949-955</ispartof><rights>Copyright © 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-e222c3c947d33694f18a2bf72ec3ccaed213cbb070aa47903e4f172a0c3df8f53</citedby><cites>FETCH-LOGICAL-a344t-e222c3c947d33694f18a2bf72ec3ccaed213cbb070aa47903e4f172a0c3df8f53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np1006636$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np1006636$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24198967$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21510636$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Simmler, Charlotte</creatorcontrib><creatorcontrib>Antheaume, Cyril</creatorcontrib><creatorcontrib>André, Patrice</creatorcontrib><creatorcontrib>Bonté, Frédéric</creatorcontrib><creatorcontrib>Lobstein, Annelise</creatorcontrib><title>Glucosyloxybenzyl Eucomate Derivatives from Vanda teres Stimulate HaCaT Cytochrome c Oxidase</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect on cytochrome c oxidase activity, implicated in mitochondrial respiratory function and cellular energy production. Eucomic acid (1) and vandateroside II (3) increased cytochrome c oxidase activity and/or expression, without enhancing cellular mitochondrial content. These two V. teres biomarkers apparently contributed to stimulate respiratory functions in keratinocytes. Since aging and its pathologies may be ascribed to a decline in mitochondrial functions, these biomarkers have the potential to become new natural ingredients for antiaging preparations to remedy age-related disorders such as skin aging.</description><subject>Biological and medical sciences</subject><subject>Electron Transport Complex IV - drug effects</subject><subject>Electron Transport Complex IV - metabolism</subject><subject>General pharmacology</subject><subject>Glucosides - chemistry</subject><subject>Glucosides - isolation & purification</subject><subject>Glucosides - pharmacology</subject><subject>Humans</subject><subject>Iridoid Glucosides - chemistry</subject><subject>Iridoid Glucosides - isolation & purification</subject><subject>Iridoid Glucosides - pharmacology</subject><subject>Keratinocytes - drug effects</subject><subject>Malates - chemistry</subject><subject>Malates - isolation & purification</subject><subject>Malates - pharmacology</subject><subject>Medical sciences</subject><subject>Mitochondria - metabolism</subject><subject>Molecular Structure</subject><subject>Orchidaceae - chemistry</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Stems - chemistry</subject><subject>Thailand</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EtLw0AUBeBBFK3VhX9AshFxEb0zk2SSpcRHBcGF1ZUQbiY3mJJHnUmK8dc70mo3ri4cPs6Fw9gJh0sOgl-1Sw4QRTLaYRMeCvAjEOEumwCPpC_jKDhgh9YuAEBCEu6zA8FDDs5P2Nt9PejOjnX3OebUfo21d-uCBnvybshUK-yrFVmvNF3jvWJboNeTccFzXzVD_cNmmOLcS8e-0-9Okae9p8-qQEtHbK_E2tLx5k7Zy93tPJ35j0_3D-n1o48yCHqfhBBa6iRQhZRREpQ8RpGXSpBLNVIhuNR5DgoQA5WAJEeUQNCyKOMylFN2vu5dmu5jINtnTWU11TW21A02i5UKIBagnLxYS206aw2V2dJUDZox45D9bJn9bens6aZ1yBsq_uTveA6cbQBajXVpsNWV3bqAJ3ESqa1DbbNFN5jWjfHPw2_RZIgE</recordid><startdate>20110527</startdate><enddate>20110527</enddate><creator>Simmler, Charlotte</creator><creator>Antheaume, Cyril</creator><creator>André, Patrice</creator><creator>Bonté, Frédéric</creator><creator>Lobstein, Annelise</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>IQODW</scope><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>20110527</creationdate><title>Glucosyloxybenzyl Eucomate Derivatives from Vanda teres Stimulate HaCaT Cytochrome c Oxidase</title><author>Simmler, Charlotte ; Antheaume, Cyril ; André, Patrice ; Bonté, Frédéric ; Lobstein, Annelise</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-e222c3c947d33694f18a2bf72ec3ccaed213cbb070aa47903e4f172a0c3df8f53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Biological and medical sciences</topic><topic>Electron Transport Complex IV - drug effects</topic><topic>Electron Transport Complex IV - metabolism</topic><topic>General pharmacology</topic><topic>Glucosides - chemistry</topic><topic>Glucosides - isolation & purification</topic><topic>Glucosides - pharmacology</topic><topic>Humans</topic><topic>Iridoid Glucosides - chemistry</topic><topic>Iridoid Glucosides - isolation & purification</topic><topic>Iridoid Glucosides - pharmacology</topic><topic>Keratinocytes - drug effects</topic><topic>Malates - chemistry</topic><topic>Malates - isolation & purification</topic><topic>Malates - pharmacology</topic><topic>Medical sciences</topic><topic>Mitochondria - metabolism</topic><topic>Molecular Structure</topic><topic>Orchidaceae - chemistry</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Stems - chemistry</topic><topic>Thailand</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Simmler, Charlotte</creatorcontrib><creatorcontrib>Antheaume, Cyril</creatorcontrib><creatorcontrib>André, Patrice</creatorcontrib><creatorcontrib>Bonté, Frédéric</creatorcontrib><creatorcontrib>Lobstein, Annelise</creatorcontrib><collection>Pascal-Francis</collection><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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Simmler, Charlotte</au><au>Antheaume, Cyril</au><au>André, Patrice</au><au>Bonté, Frédéric</au><au>Lobstein, Annelise</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glucosyloxybenzyl Eucomate Derivatives from Vanda teres Stimulate HaCaT Cytochrome c Oxidase</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2011-05-27</date><risdate>2011</risdate><volume>74</volume><issue>5</issue><spage>949</spage><epage>955</epage><pages>949-955</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect on cytochrome c oxidase activity, implicated in mitochondrial respiratory function and cellular energy production. Eucomic acid (1) and vandateroside II (3) increased cytochrome c oxidase activity and/or expression, without enhancing cellular mitochondrial content. These two V. teres biomarkers apparently contributed to stimulate respiratory functions in keratinocytes. Since aging and its pathologies may be ascribed to a decline in mitochondrial functions, these biomarkers have the potential to become new natural ingredients for antiaging preparations to remedy age-related disorders such as skin aging.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>21510636</pmid><doi>10.1021/np1006636</doi><tpages>7</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | Biological and medical sciences Electron Transport Complex IV - drug effects Electron Transport Complex IV - metabolism General pharmacology Glucosides - chemistry Glucosides - isolation & purification Glucosides - pharmacology Humans Iridoid Glucosides - chemistry Iridoid Glucosides - isolation & purification Iridoid Glucosides - pharmacology Keratinocytes - drug effects Malates - chemistry Malates - isolation & purification Malates - pharmacology Medical sciences Mitochondria - metabolism Molecular Structure Orchidaceae - chemistry Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Stems - chemistry Thailand |
| title | Glucosyloxybenzyl Eucomate Derivatives from Vanda teres Stimulate HaCaT Cytochrome c Oxidase |
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