Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis.
Identifieur interne : 000927 ( Ncbi/Checkpoint ); précédent : 000926; suivant : 000928Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis.
Auteurs : Hang Xiao [États-Unis] ; Chung S. Yang ; Shiming Li ; Huanyu Jin ; Chi-Tang Ho ; Trusha PatelSource :
- Molecular nutrition & food research [ 1613-4133 ] ; 2009.
English descriptors
- KwdEn :
- Anticarcinogenic Agents (pharmacology), Antioxidants (pharmacology), Apoptosis (drug effects), Cell Division (drug effects), Cell Line, Tumor, Citrus sinensis (chemistry), Flavones (chemistry), Flavones (isolation & purification), Flavones (pharmacology), Flavonoids (pharmacology), Fruit (chemistry), Humans, Hydroxylation, Lung Neoplasms (pathology), Structure-Activity Relationship.
- MESH :
- chemical , chemistry : Flavones.
- chemical , isolation & purification : Flavones.
- chemical , pharmacology : Anticarcinogenic Agents, Antioxidants, Flavones, Flavonoids.
- chemistry : Citrus sinensis, Fruit.
- drug effects : Apoptosis, Cell Division.
- pathology : Lung Neoplasms.
- Cell Line, Tumor, Humans, Hydroxylation, Structure-Activity Relationship.
Abstract
Polymethoxyflavones (PMFs) are almost exclusively found in the Citrus genus, particularly in the peels of sweet orange (Citrus sinensis L. Osbeck) and mandarin (C. reticulate Blanco). We studied the effects of two major PMFs, namely, nobiletin and 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF), and two major monodemethylated PMFs, namely 5-hydroxy-3,7,8,3',4'-pentamethoxyflavone (5HPMF), and 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone (5HHMF), on the growth of human lung cancer H1299, H441, and H460 cells. Monodemethylated PMFs were much more potent in growth inhibition of lung cancer cells than their permethoxylated counterpart PMFs. In H1299 cells, cell cycle analyses further revealed that monodemethylated PMFs caused significant increase in sub-G0/G1 phase, suggesting possible role of apoptosis in the growth inhibition observed, whereas the permethoxylated counterpart PMFs did not affect cell cycle distribution at same concentrations tested. These results strongly suggested that the phenolic group is essential for the growth inhibitory activity of monodemethylated PMFs. Further studies in H1299 cells demonstrated that monodemethylated PMFs downregulated oncogenic proteins, such as iNOS, COX-2, Mcl-1, and K-ras, as well as induced apoptosis evidenced by activation of caspase-3 and cleavage of PARP. Our results provide rationale to develop orange peel extract enriched with monodemethylated PMFs into value-added nutraceutical products for cancer prevention.
DOI: 10.1002/mnfr.200800057
PubMed: 19065586
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis.</title><author><name sortKey="Xiao, Hang" sort="Xiao, Hang" uniqKey="Xiao H" first="Hang" last="Xiao">Hang Xiao</name><affiliation wicri:level="4"><nlm:affiliation>Department of Food Science, University of Massachusetts, Amherst, MA 01003, USA. hangxiao@foodsci.umass.edu</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Food Science, University of Massachusetts, Amherst, MA 01003</wicri:regionArea><placeName><region type="state">Massachusetts</region><settlement type="city">Amherst (Massachusetts)</settlement></placeName><orgName type="university">Université du Massachusetts</orgName></affiliation></author><author><name sortKey="Yang, Chung S" sort="Yang, Chung S" uniqKey="Yang C" first="Chung S" last="Yang">Chung S. Yang</name></author><author><name sortKey="Li, Shiming" sort="Li, Shiming" uniqKey="Li S" first="Shiming" last="Li">Shiming Li</name></author><author><name sortKey="Jin, Huanyu" sort="Jin, Huanyu" uniqKey="Jin H" first="Huanyu" last="Jin">Huanyu Jin</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><author><name sortKey="Patel, Trusha" sort="Patel, Trusha" uniqKey="Patel T" first="Trusha" last="Patel">Trusha Patel</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2009">2009</date><idno type="RBID">pubmed:19065586</idno><idno type="pmid">19065586</idno><idno type="doi">10.1002/mnfr.200800057</idno><idno type="wicri:Area/PubMed/Corpus">000976</idno><idno type="wicri:Area/PubMed/Curation">000976</idno><idno type="wicri:Area/PubMed/Checkpoint">000976</idno><idno type="wicri:Area/Ncbi/Merge">000927</idno><idno type="wicri:Area/Ncbi/Curation">000927</idno><idno type="wicri:Area/Ncbi/Checkpoint">000927</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis.</title><author><name sortKey="Xiao, Hang" sort="Xiao, Hang" uniqKey="Xiao H" first="Hang" last="Xiao">Hang Xiao</name><affiliation wicri:level="4"><nlm:affiliation>Department of Food Science, University of Massachusetts, Amherst, MA 01003, USA. hangxiao@foodsci.umass.edu</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Food Science, University of Massachusetts, Amherst, MA 01003</wicri:regionArea><placeName><region type="state">Massachusetts</region><settlement type="city">Amherst (Massachusetts)</settlement></placeName><orgName type="university">Université du Massachusetts</orgName></affiliation></author><author><name sortKey="Yang, Chung S" sort="Yang, Chung S" uniqKey="Yang C" first="Chung S" last="Yang">Chung S. Yang</name></author><author><name sortKey="Li, Shiming" sort="Li, Shiming" uniqKey="Li S" first="Shiming" last="Li">Shiming Li</name></author><author><name sortKey="Jin, Huanyu" sort="Jin, Huanyu" uniqKey="Jin H" first="Huanyu" last="Jin">Huanyu Jin</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><author><name sortKey="Patel, Trusha" sort="Patel, Trusha" uniqKey="Patel T" first="Trusha" last="Patel">Trusha Patel</name></author></analytic><series><title level="j">Molecular nutrition & food research</title><idno type="eISSN">1613-4133</idno><imprint><date when="2009" type="published">2009</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anticarcinogenic Agents (pharmacology)</term><term>Antioxidants (pharmacology)</term><term>Apoptosis (drug effects)</term><term>Cell Division (drug effects)</term><term>Cell Line, Tumor</term><term>Citrus sinensis (chemistry)</term><term>Flavones (chemistry)</term><term>Flavones (isolation & purification)</term><term>Flavones (pharmacology)</term><term>Flavonoids (pharmacology)</term><term>Fruit (chemistry)</term><term>Humans</term><term>Hydroxylation</term><term>Lung Neoplasms (pathology)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Flavones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Flavones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anticarcinogenic Agents</term><term>Antioxidants</term><term>Flavones</term><term>Flavonoids</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Citrus sinensis</term><term>Fruit</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Apoptosis</term><term>Cell Division</term></keywords><keywords scheme="MESH" qualifier="pathology" xml:lang="en"><term>Lung Neoplasms</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line, Tumor</term><term>Humans</term><term>Hydroxylation</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Polymethoxyflavones (PMFs) are almost exclusively found in the Citrus genus, particularly in the peels of sweet orange (Citrus sinensis L. Osbeck) and mandarin (C. reticulate Blanco). We studied the effects of two major PMFs, namely, nobiletin and 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF), and two major monodemethylated PMFs, namely 5-hydroxy-3,7,8,3',4'-pentamethoxyflavone (5HPMF), and 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone (5HHMF), on the growth of human lung cancer H1299, H441, and H460 cells. Monodemethylated PMFs were much more potent in growth inhibition of lung cancer cells than their permethoxylated counterpart PMFs. In H1299 cells, cell cycle analyses further revealed that monodemethylated PMFs caused significant increase in sub-G0/G1 phase, suggesting possible role of apoptosis in the growth inhibition observed, whereas the permethoxylated counterpart PMFs did not affect cell cycle distribution at same concentrations tested. These results strongly suggested that the phenolic group is essential for the growth inhibitory activity of monodemethylated PMFs. Further studies in H1299 cells demonstrated that monodemethylated PMFs downregulated oncogenic proteins, such as iNOS, COX-2, Mcl-1, and K-ras, as well as induced apoptosis evidenced by activation of caspase-3 and cleavage of PARP. Our results provide rationale to develop orange peel extract enriched with monodemethylated PMFs into value-added nutraceutical products for cancer prevention.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Massachusetts</li></region><settlement><li>Amherst (Massachusetts)</li></settlement><orgName><li>Université du Massachusetts</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="Jin, Huanyu" sort="Jin, Huanyu" uniqKey="Jin H" first="Huanyu" last="Jin">Huanyu Jin</name><name sortKey="Li, Shiming" sort="Li, Shiming" uniqKey="Li S" first="Shiming" last="Li">Shiming Li</name><name sortKey="Patel, Trusha" sort="Patel, Trusha" uniqKey="Patel T" first="Trusha" last="Patel">Trusha Patel</name><name sortKey="Yang, Chung S" sort="Yang, Chung S" uniqKey="Yang C" first="Chung S" last="Yang">Chung S. Yang</name></noCountry><country name="États-Unis"><region name="Massachusetts"><name sortKey="Xiao, Hang" sort="Xiao, Hang" uniqKey="Xiao H" first="Hang" last="Xiao">Hang Xiao</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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