Inhibitory Effects of Zingiber officinale Roscoe Derived Components on Aldose Reductase Activity in Vitro and in Vivo
Ginger (Zingiber officinale Roscoe) continues to be used as an important cooking spice and herbal medicine around the world. Scientific research has gradually verified the antidiabetic effects of ginger. Especially gingerols, which are the major components of ginger, are known to improve diabetes in...
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Veröffentlicht in: | Journal of agricultural and food chemistry 2006-09, Vol.54 (18), p.6640-6644 |
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description | Ginger (Zingiber officinale Roscoe) continues to be used as an important cooking spice and herbal medicine around the world. Scientific research has gradually verified the antidiabetic effects of ginger. Especially gingerols, which are the major components of ginger, are known to improve diabetes including the effect of enhancement against insulin-sensitivity. Aldose reductase inhibitors have considerable potential for the treatment of diabetes, without increased risk of hypoglycemia. The assay for aldose reductase inhibitors in ginger led to the isolation of five active compounds including 2-(4-hydroxy-3-methoxyphenyl)ethanol (2) and 2-(4-hydroxy-3-methoxyphenyl)ethanoic acid (3). Compounds 2 and 3 were good inhibitors of recombinant human aldose reductase, with IC50 values of 19.2 ± 1.9 and 18.5 ± 1.1 μM, respectively. Furthermore, these compounds significantly suppressed not only sorbitol accumulation in human erythrocytes but also lens galactitol accumulation in 30% of galactose-fed cataract rat model. A structure−activity relationship study revealed that the applicable side alkyl chain length and the presence of a C3 OCH3 group in the aromatic ring are essential features for enzyme recognition and binding. These results suggested that it would contribute to the protection against or improvement of diabetic complications for a dietary supplement of ginger or its extract containing aldose reductase inhibitors. Keywords: Zingiber officinale; ginger; aldose reductase inhibitor; erythrocyte; sorbitol; galactosemia; diabetes |
doi_str_mv | 10.1021/jf061599a |
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Scientific research has gradually verified the antidiabetic effects of ginger. Especially gingerols, which are the major components of ginger, are known to improve diabetes including the effect of enhancement against insulin-sensitivity. Aldose reductase inhibitors have considerable potential for the treatment of diabetes, without increased risk of hypoglycemia. The assay for aldose reductase inhibitors in ginger led to the isolation of five active compounds including 2-(4-hydroxy-3-methoxyphenyl)ethanol (2) and 2-(4-hydroxy-3-methoxyphenyl)ethanoic acid (3). Compounds 2 and 3 were good inhibitors of recombinant human aldose reductase, with IC50 values of 19.2 ± 1.9 and 18.5 ± 1.1 μM, respectively. Furthermore, these compounds significantly suppressed not only sorbitol accumulation in human erythrocytes but also lens galactitol accumulation in 30% of galactose-fed cataract rat model. A structure−activity relationship study revealed that the applicable side alkyl chain length and the presence of a C3 OCH3 group in the aromatic ring are essential features for enzyme recognition and binding. These results suggested that it would contribute to the protection against or improvement of diabetic complications for a dietary supplement of ginger or its extract containing aldose reductase inhibitors. Keywords: Zingiber officinale; ginger; aldose reductase inhibitor; erythrocyte; sorbitol; galactosemia; diabetes</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf061599a</identifier><identifier>PMID: 16939321</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject><![CDATA[Aldehyde Reductase - antagonists & inhibitors ; aldo0se reductase ; Animals ; Aroma and flavouring agent industries ; Benzene Derivatives - isolation & purification ; Biological and medical sciences ; carbohydrate content ; carbohydrate metabolism ; Carboxylic Acids - isolation & purification ; cataract ; diabetes ; enzyme activity ; enzyme inhibition ; enzyme inhibitors ; Enzyme Inhibitors - isolation & purification ; Enzyme Inhibitors - pharmacology ; erythrocytes ; Erythrocytes - drug effects ; Erythrocytes - metabolism ; eye lens ; Food industries ; Fundamental and applied biological sciences. Psychology ; galactitol ; Galactitol - metabolism ; ginger ; ginger root ; Humans ; Lens, Crystalline - drug effects ; Lens, Crystalline - metabolism ; Male ; medicinal properties ; oxidoreductases ; Phenylethyl Alcohol - analogs & derivatives ; Phenylethyl Alcohol - isolation & purification ; Rats ; Rats, Wistar ; Recombinant Proteins ; sorbitol ; Sorbitol - metabolism ; structure-activity relationships ; Zingiber officinale ; Zingiber officinale - chemistry]]></subject><ispartof>Journal of agricultural and food chemistry, 2006-09, Vol.54 (18), p.6640-6644</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-becbb0027f4cdb1349c7f29bacb2b861b95b8543a0dcc98e7c5d7b1c4c3113903</citedby><cites>FETCH-LOGICAL-a405t-becbb0027f4cdb1349c7f29bacb2b861b95b8543a0dcc98e7c5d7b1c4c3113903</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/jf061599a$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf061599a$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18083084$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16939321$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kato, Atsushi</creatorcontrib><creatorcontrib>Higuchi, Yasuko</creatorcontrib><creatorcontrib>Goto, Hirozo</creatorcontrib><creatorcontrib>Kizu, Haruhisa</creatorcontrib><creatorcontrib>Okamoto, Tadashi</creatorcontrib><creatorcontrib>Asano, Naoki</creatorcontrib><creatorcontrib>Hollinshead, Jackie</creatorcontrib><creatorcontrib>Nash, Robert J</creatorcontrib><creatorcontrib>Adachi, Isao</creatorcontrib><title>Inhibitory Effects of Zingiber officinale Roscoe Derived Components on Aldose Reductase Activity in Vitro and in Vivo</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Ginger (Zingiber officinale Roscoe) continues to be used as an important cooking spice and herbal medicine around the world. Scientific research has gradually verified the antidiabetic effects of ginger. Especially gingerols, which are the major components of ginger, are known to improve diabetes including the effect of enhancement against insulin-sensitivity. Aldose reductase inhibitors have considerable potential for the treatment of diabetes, without increased risk of hypoglycemia. The assay for aldose reductase inhibitors in ginger led to the isolation of five active compounds including 2-(4-hydroxy-3-methoxyphenyl)ethanol (2) and 2-(4-hydroxy-3-methoxyphenyl)ethanoic acid (3). Compounds 2 and 3 were good inhibitors of recombinant human aldose reductase, with IC50 values of 19.2 ± 1.9 and 18.5 ± 1.1 μM, respectively. Furthermore, these compounds significantly suppressed not only sorbitol accumulation in human erythrocytes but also lens galactitol accumulation in 30% of galactose-fed cataract rat model. A structure−activity relationship study revealed that the applicable side alkyl chain length and the presence of a C3 OCH3 group in the aromatic ring are essential features for enzyme recognition and binding. These results suggested that it would contribute to the protection against or improvement of diabetic complications for a dietary supplement of ginger or its extract containing aldose reductase inhibitors. Keywords: Zingiber officinale; ginger; aldose reductase inhibitor; erythrocyte; sorbitol; galactosemia; diabetes</description><subject>Aldehyde Reductase - antagonists & inhibitors</subject><subject>aldo0se reductase</subject><subject>Animals</subject><subject>Aroma and flavouring agent industries</subject><subject>Benzene Derivatives - isolation & purification</subject><subject>Biological and medical sciences</subject><subject>carbohydrate content</subject><subject>carbohydrate metabolism</subject><subject>Carboxylic Acids - isolation & purification</subject><subject>cataract</subject><subject>diabetes</subject><subject>enzyme activity</subject><subject>enzyme inhibition</subject><subject>enzyme inhibitors</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>erythrocytes</subject><subject>Erythrocytes - drug effects</subject><subject>Erythrocytes - metabolism</subject><subject>eye lens</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>galactitol</subject><subject>Galactitol - metabolism</subject><subject>ginger</subject><subject>ginger root</subject><subject>Humans</subject><subject>Lens, Crystalline - drug effects</subject><subject>Lens, Crystalline - metabolism</subject><subject>Male</subject><subject>medicinal properties</subject><subject>oxidoreductases</subject><subject>Phenylethyl Alcohol - analogs & derivatives</subject><subject>Phenylethyl Alcohol - isolation & purification</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Recombinant Proteins</subject><subject>sorbitol</subject><subject>Sorbitol - metabolism</subject><subject>structure-activity relationships</subject><subject>Zingiber officinale</subject><subject>Zingiber officinale - chemistry</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0c1vFCEUAHBiNHZbPfgPKBdNPIzCMMzAcbP2K1k_YltjvBBgoLLOwgrMxv3vpc6kvXjikffjwXsA8AKjdxjV-P3GohZTzuUjsMC0RhXFmD0GC1SSFaMtPgLHKW0QQox26Ck4wi0nnNR4AcZL_9Mpl0M8wFNrjc4JBgt_OH_rlIkltk47LwcDv4akg4EfTHR708NV2O6CN_7ugIfLoQ-pGNOPOssSLXV2e5cP0Hn4zeUYoPT9tNmHZ-CJlUMyz-f1BNycnV6vLqr15_PL1XJdyQbRXCmjlSpNdLbRvcKk4bqzNVdSq1qxFitOFaMNkajXmjPTadp3CutGE4wJR-QEvJnq7mL4PZqUxdYlbYZBehPGJFrGUNeytsC3E9QxpBSNFbvotjIeBEbibsbifsbFvpyLjmpr-gc5D7WA1zOQScvBRum1Sw-OIUYQa4qrJudSNn_u8zL-Em1HOiquv1wJ9L35uL7gZ-JT8a8mb2UQ8jaWmjdXNcIE4fLE7l_F-Wapk9iEMZaPS_9p4S-CAKkr</recordid><startdate>20060906</startdate><enddate>20060906</enddate><creator>Kato, Atsushi</creator><creator>Higuchi, Yasuko</creator><creator>Goto, Hirozo</creator><creator>Kizu, Haruhisa</creator><creator>Okamoto, Tadashi</creator><creator>Asano, Naoki</creator><creator>Hollinshead, Jackie</creator><creator>Nash, Robert J</creator><creator>Adachi, Isao</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><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>20060906</creationdate><title>Inhibitory Effects of Zingiber officinale Roscoe Derived Components on Aldose Reductase Activity in Vitro and in Vivo</title><author>Kato, Atsushi ; Higuchi, Yasuko ; Goto, Hirozo ; Kizu, Haruhisa ; Okamoto, Tadashi ; Asano, Naoki ; Hollinshead, Jackie ; Nash, Robert J ; Adachi, Isao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-becbb0027f4cdb1349c7f29bacb2b861b95b8543a0dcc98e7c5d7b1c4c3113903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Aldehyde Reductase - antagonists & inhibitors</topic><topic>aldo0se reductase</topic><topic>Animals</topic><topic>Aroma and flavouring agent industries</topic><topic>Benzene Derivatives - isolation & purification</topic><topic>Biological and medical sciences</topic><topic>carbohydrate content</topic><topic>carbohydrate metabolism</topic><topic>Carboxylic Acids - isolation & purification</topic><topic>cataract</topic><topic>diabetes</topic><topic>enzyme activity</topic><topic>enzyme inhibition</topic><topic>enzyme inhibitors</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>erythrocytes</topic><topic>Erythrocytes - drug effects</topic><topic>Erythrocytes - metabolism</topic><topic>eye lens</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>galactitol</topic><topic>Galactitol - metabolism</topic><topic>ginger</topic><topic>ginger root</topic><topic>Humans</topic><topic>Lens, Crystalline - drug effects</topic><topic>Lens, Crystalline - metabolism</topic><topic>Male</topic><topic>medicinal properties</topic><topic>oxidoreductases</topic><topic>Phenylethyl Alcohol - analogs & derivatives</topic><topic>Phenylethyl Alcohol - isolation & purification</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Recombinant Proteins</topic><topic>sorbitol</topic><topic>Sorbitol - metabolism</topic><topic>structure-activity relationships</topic><topic>Zingiber officinale</topic><topic>Zingiber officinale - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kato, Atsushi</creatorcontrib><creatorcontrib>Higuchi, Yasuko</creatorcontrib><creatorcontrib>Goto, Hirozo</creatorcontrib><creatorcontrib>Kizu, Haruhisa</creatorcontrib><creatorcontrib>Okamoto, Tadashi</creatorcontrib><creatorcontrib>Asano, Naoki</creatorcontrib><creatorcontrib>Hollinshead, Jackie</creatorcontrib><creatorcontrib>Nash, Robert J</creatorcontrib><creatorcontrib>Adachi, Isao</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><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 agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kato, Atsushi</au><au>Higuchi, Yasuko</au><au>Goto, Hirozo</au><au>Kizu, Haruhisa</au><au>Okamoto, Tadashi</au><au>Asano, Naoki</au><au>Hollinshead, Jackie</au><au>Nash, Robert J</au><au>Adachi, Isao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibitory Effects of Zingiber officinale Roscoe Derived Components on Aldose Reductase Activity in Vitro and in Vivo</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2006-09-06</date><risdate>2006</risdate><volume>54</volume><issue>18</issue><spage>6640</spage><epage>6644</epage><pages>6640-6644</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Ginger (Zingiber officinale Roscoe) continues to be used as an important cooking spice and herbal medicine around the world. Scientific research has gradually verified the antidiabetic effects of ginger. Especially gingerols, which are the major components of ginger, are known to improve diabetes including the effect of enhancement against insulin-sensitivity. Aldose reductase inhibitors have considerable potential for the treatment of diabetes, without increased risk of hypoglycemia. The assay for aldose reductase inhibitors in ginger led to the isolation of five active compounds including 2-(4-hydroxy-3-methoxyphenyl)ethanol (2) and 2-(4-hydroxy-3-methoxyphenyl)ethanoic acid (3). Compounds 2 and 3 were good inhibitors of recombinant human aldose reductase, with IC50 values of 19.2 ± 1.9 and 18.5 ± 1.1 μM, respectively. Furthermore, these compounds significantly suppressed not only sorbitol accumulation in human erythrocytes but also lens galactitol accumulation in 30% of galactose-fed cataract rat model. A structure−activity relationship study revealed that the applicable side alkyl chain length and the presence of a C3 OCH3 group in the aromatic ring are essential features for enzyme recognition and binding. These results suggested that it would contribute to the protection against or improvement of diabetic complications for a dietary supplement of ginger or its extract containing aldose reductase inhibitors. Keywords: Zingiber officinale; ginger; aldose reductase inhibitor; erythrocyte; sorbitol; galactosemia; diabetes</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16939321</pmid><doi>10.1021/jf061599a</doi><tpages>5</tpages></addata></record> |
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subjects | Aldehyde Reductase - antagonists & inhibitors aldo0se reductase Animals Aroma and flavouring agent industries Benzene Derivatives - isolation & purification Biological and medical sciences carbohydrate content carbohydrate metabolism Carboxylic Acids - isolation & purification cataract diabetes enzyme activity enzyme inhibition enzyme inhibitors Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology erythrocytes Erythrocytes - drug effects Erythrocytes - metabolism eye lens Food industries Fundamental and applied biological sciences. Psychology galactitol Galactitol - metabolism ginger ginger root Humans Lens, Crystalline - drug effects Lens, Crystalline - metabolism Male medicinal properties oxidoreductases Phenylethyl Alcohol - analogs & derivatives Phenylethyl Alcohol - isolation & purification Rats Rats, Wistar Recombinant Proteins sorbitol Sorbitol - metabolism structure-activity relationships Zingiber officinale Zingiber officinale - chemistry |
title | Inhibitory Effects of Zingiber officinale Roscoe Derived Components on Aldose Reductase Activity in Vitro and in Vivo |
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