Identification of nobiletin metabolites in mouse urine.
Identifieur interne : 002536 ( Main/Exploration ); précédent : 002535; suivant : 002537Identification of nobiletin metabolites in mouse urine.
Auteurs : Shiming Li [États-Unis] ; Zhenyu Wang ; Shengmin Sang ; Mou-Tuan Huang ; Chi-Tang HoSource :
- Molecular nutrition & food research [ 1613-4125 ] ; 2006.
English descriptors
- KwdEn :
- Animals, Antioxidants, Chromatography (methods), Chromatography, High Pressure Liquid, Citrus sinensis (chemistry), Female, Flavones (metabolism), Flavones (urine), Fruit (chemistry), Glucuronic Acid (metabolism), Magnetic Resonance Spectroscopy, Methylation, Mice, Spectrometry, Mass, Electrospray Ionization, Sulfates (metabolism).
- MESH :
- chemical , metabolism : Flavones, Glucuronic Acid, Sulfates.
- chemical , urine : Flavones.
- chemical : Antioxidants.
- chemistry : Citrus sinensis, Fruit.
- methods : Chromatography.
- Animals, Chromatography, High Pressure Liquid, Female, Magnetic Resonance Spectroscopy, Methylation, Mice, Spectrometry, Mass, Electrospray Ionization.
Abstract
Nobiletin, a major component of citrus polymethoxyflavones, has many potential significant health benefits. While the biological activities of nobiletin have been widely reported, its in vitro and in vivo metabolic fate has been rarely studied. To explore the biotransformation mechanism of nobiletin we conducted an investigation into its metabolic profile in mouse urine, by various analytical techniques. Due to sample amount limitations for isolating and characterizing an individual metabolite, two possible nobiletin metabolites were prepared in a similar multi-step organic synthetic route: 3'-hydroxy-5,6,7,8,4'-pentamethoxyflavone (3'-demethylnobiletin) and 4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone (4'-demethylnobiletin). Normal phase (silica gel) and C(18) reverse phase chromatography, as well as liquid chromatography-mass spectrometry-mass spectrometry, were employed in the separation of 3'-demethylnobiletin and 4'-demethylnobiletin, however, without success due to the structural similarities of these mono-demethylated nobiletins. Using a chiral packed column eluted under supercritical fluid chromatography (SFC) conditions, a clear separation was achieved. Thus, by comparing the SFC profiles of metabolite mixtures with the synthesized standard compounds, the major nobiletin metabolite of mouse urine is identified as 4'-demethylnobiletin, whereas 3'-demethylnobiletin is a minor metabolite. In this study, the concentration of 4'-demethylnobiletin in mouse urine is 28.9 microg/mL.
DOI: 10.1002/mnfr.200500214
PubMed: 16521176
Affiliations:
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Sang</name></author><author><name sortKey="Huang, Mou Tuan" sort="Huang, Mou Tuan" uniqKey="Huang M" first="Mou-Tuan" last="Huang">Mou-Tuan Huang</name></author><author><name sortKey="Ho, Chi Tang" sort="Ho, Chi Tang" uniqKey="Ho C" first="Chi-Tang" last="Ho">Chi-Tang Ho</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2006">2006</date><idno type="RBID">pubmed:16521176</idno><idno type="pmid">16521176</idno><idno type="doi">10.1002/mnfr.200500214</idno><idno type="wicri:Area/PubMed/Corpus">000C36</idno><idno type="wicri:Area/PubMed/Curation">000C36</idno><idno type="wicri:Area/PubMed/Checkpoint">000C36</idno><idno type="wicri:Area/Ncbi/Merge">000476</idno><idno type="wicri:Area/Ncbi/Curation">000476</idno><idno type="wicri:Area/Ncbi/Checkpoint">000476</idno><idno type="wicri:doubleKey">1613-4125:2006:Li S:identification:of:nobiletin</idno><idno type="wicri:Area/Main/Merge">002636</idno><idno 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Shengmin" sort="Sang, Shengmin" uniqKey="Sang S" first="Shengmin" last="Sang">Shengmin Sang</name></author><author><name sortKey="Huang, Mou Tuan" sort="Huang, Mou Tuan" uniqKey="Huang M" first="Mou-Tuan" last="Huang">Mou-Tuan Huang</name></author><author><name sortKey="Ho, Chi Tang" sort="Ho, Chi Tang" uniqKey="Ho C" first="Chi-Tang" last="Ho">Chi-Tang Ho</name></author></analytic><series><title level="j">Molecular nutrition & food research</title><idno type="ISSN">1613-4125</idno><imprint><date when="2006" type="published">2006</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antioxidants</term><term>Chromatography (methods)</term><term>Chromatography, High Pressure Liquid</term><term>Citrus sinensis (chemistry)</term><term>Female</term><term>Flavones (metabolism)</term><term>Flavones (urine)</term><term>Fruit (chemistry)</term><term>Glucuronic Acid (metabolism)</term><term>Magnetic Resonance Spectroscopy</term><term>Methylation</term><term>Mice</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Sulfates (metabolism)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Flavones</term><term>Glucuronic Acid</term><term>Sulfates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="urine" xml:lang="en"><term>Flavones</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Antioxidants</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Citrus sinensis</term><term>Fruit</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chromatography</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Chromatography, High Pressure Liquid</term><term>Female</term><term>Magnetic Resonance Spectroscopy</term><term>Methylation</term><term>Mice</term><term>Spectrometry, Mass, Electrospray Ionization</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Nobiletin, a major component of citrus polymethoxyflavones, has many potential significant health benefits. While the biological activities of nobiletin have been widely reported, its in vitro and in vivo metabolic fate has been rarely studied. To explore the biotransformation mechanism of nobiletin we conducted an investigation into its metabolic profile in mouse urine, by various analytical techniques. Due to sample amount limitations for isolating and characterizing an individual metabolite, two possible nobiletin metabolites were prepared in a similar multi-step organic synthetic route: 3'-hydroxy-5,6,7,8,4'-pentamethoxyflavone (3'-demethylnobiletin) and 4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone (4'-demethylnobiletin). Normal phase (silica gel) and C(18) reverse phase chromatography, as well as liquid chromatography-mass spectrometry-mass spectrometry, were employed in the separation of 3'-demethylnobiletin and 4'-demethylnobiletin, however, without success due to the structural similarities of these mono-demethylated nobiletins. Using a chiral packed column eluted under supercritical fluid chromatography (SFC) conditions, a clear separation was achieved. Thus, by comparing the SFC profiles of metabolite mixtures with the synthesized standard compounds, the major nobiletin metabolite of mouse urine is identified as 4'-demethylnobiletin, whereas 3'-demethylnobiletin is a minor metabolite. In this study, the concentration of 4'-demethylnobiletin in mouse urine is 28.9 microg/mL.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>New Jersey</li></region><settlement><li>New Brunswick (New Jersey)</li></settlement><orgName><li>Université Rutgers</li></orgName></list><tree><noCountry><name sortKey="Ho, Chi Tang" sort="Ho, Chi Tang" uniqKey="Ho C" first="Chi-Tang" last="Ho">Chi-Tang Ho</name><name sortKey="Huang, Mou Tuan" sort="Huang, Mou Tuan" uniqKey="Huang M" first="Mou-Tuan" last="Huang">Mou-Tuan Huang</name><name sortKey="Sang, Shengmin" sort="Sang, Shengmin" uniqKey="Sang S" first="Shengmin" last="Sang">Shengmin Sang</name><name sortKey="Wang, Zhenyu" sort="Wang, Zhenyu" uniqKey="Wang Z" first="Zhenyu" last="Wang">Zhenyu Wang</name></noCountry><country name="États-Unis"><region name="New Jersey"><name sortKey="Li, Shiming" sort="Li, Shiming" uniqKey="Li S" first="Shiming" last="Li">Shiming Li</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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