Extraction and identification of three major aldose reductase inhibitors from Artemisia montana
Aldose reductase inhibitors (ARIs) provide an important therapeutic and preventive opportunity against hyperglycemia associated diabetic complications. The methanolic extracts of 12 species from the genus Artemisia exhibited significant in vitro rat lens AR (RLAR) inhibitory activities with IC50 val...
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| Veröffentlicht in: | Food and chemical toxicology 2011-02, Vol.49 (2), p.376-384 |
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| creator | Jung, Hyun Ah Islam, M.D. Nurul Kwon, Yong Soo Jin, Seong Eun Son, You Kyung Park, Jin Ju Sohn, Hee Sook Choi, Jae Sue |
| description | Aldose reductase inhibitors (ARIs) provide an important therapeutic and preventive opportunity against hyperglycemia associated diabetic complications. The methanolic extracts of 12 species from the genus Artemisia exhibited significant in vitro rat lens AR (RLAR) inhibitory activities with IC50 values ranging from 0.51 to 13.45μg/mL (quercetin, 0.64μg/mL). Since the whole plant of Artemisia montana showed the highest RLAR inhibitory activity, bioassay-guided fractionation was performed to obtain ethyl acetate and n-butanol fractions. Repeated column chromatography of two active fractions, yielded fifteen compounds, including four chlorogenic acids (3,5-di-O-caffeoylquinic acid, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid), six flavonoids (apigenin, luteolin, quercetin, isoquercitrin, hyperoside, luteolin 7-rutinoside), and five coumarins (umbelliferone, scoparone, scopoletin, esculetin, and scopolin); their structures were confirmed by spectroscopic methods. 3,5-Di-O-caffeoylquinic acid and chlorogenic acid, as well as test flavonoids, displayed the most potent RLAR inhibitory activities with IC50 values ranging from 0.19 to 5.37μM. Furthermore, the HPLC profiles of the ethyl acetate and n-butanol fractions indicated that 3,5-di-O-caffeoylquinic acid, chlorogenic acid, and hyperoside, as major compounds, might play crucial roles in RLAR inhibition. The results suggest that A. montana and three key AR inhibitors therein would clearly be potential candidates as therapeutic or preventive agents for diabetic complications. |
| doi_str_mv | 10.1016/j.fct.2010.11.012 |
| format | Article |
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The methanolic extracts of 12 species from the genus Artemisia exhibited significant in vitro rat lens AR (RLAR) inhibitory activities with IC50 values ranging from 0.51 to 13.45μg/mL (quercetin, 0.64μg/mL). Since the whole plant of Artemisia montana showed the highest RLAR inhibitory activity, bioassay-guided fractionation was performed to obtain ethyl acetate and n-butanol fractions. Repeated column chromatography of two active fractions, yielded fifteen compounds, including four chlorogenic acids (3,5-di-O-caffeoylquinic acid, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid), six flavonoids (apigenin, luteolin, quercetin, isoquercitrin, hyperoside, luteolin 7-rutinoside), and five coumarins (umbelliferone, scoparone, scopoletin, esculetin, and scopolin); their structures were confirmed by spectroscopic methods. 3,5-Di-O-caffeoylquinic acid and chlorogenic acid, as well as test flavonoids, displayed the most potent RLAR inhibitory activities with IC50 values ranging from 0.19 to 5.37μM. Furthermore, the HPLC profiles of the ethyl acetate and n-butanol fractions indicated that 3,5-di-O-caffeoylquinic acid, chlorogenic acid, and hyperoside, as major compounds, might play crucial roles in RLAR inhibition. The results suggest that A. montana and three key AR inhibitors therein would clearly be potential candidates as therapeutic or preventive agents for diabetic complications.</description><identifier>ISSN: 0278-6915</identifier><identifier>EISSN: 1873-6351</identifier><identifier>DOI: 10.1016/j.fct.2010.11.012</identifier><identifier>PMID: 21092751</identifier><identifier>CODEN: FCTOD7</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>aldehyde reductase ; Aldehyde Reductase - antagonists & inhibitors ; Aldose reductase ; Animals ; apigenin ; Artemisia ; Artemisia - chemistry ; Artemisia montana ; Biological and medical sciences ; Caffeoylquinic acid ; chlorogenic acid ; Compositae ; diabetic complications ; ethyl acetate ; Flavonoids - chemistry ; Flavonoids - pharmacology ; fractionation ; General pharmacology ; high performance liquid chromatography ; HPLC ; hyperglycemia ; Hyperoside ; Inhibitory Concentration 50 ; isoquercitrin ; Lens, Crystalline - enzymology ; luteolin ; Medical sciences ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; quercetin ; Rats ; Republic of Korea ; scopoletin ; spectroscopy ; umbelliferones</subject><ispartof>Food and chemical toxicology, 2011-02, Vol.49 (2), p.376-384</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-39994173e41d49dfc33f64faa9e4d6e96c2207450fb0002beda2906f2c65fcac3</citedby><cites>FETCH-LOGICAL-c438t-39994173e41d49dfc33f64faa9e4d6e96c2207450fb0002beda2906f2c65fcac3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0278691510006708$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23834919$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21092751$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jung, Hyun Ah</creatorcontrib><creatorcontrib>Islam, M.D. Nurul</creatorcontrib><creatorcontrib>Kwon, Yong Soo</creatorcontrib><creatorcontrib>Jin, Seong Eun</creatorcontrib><creatorcontrib>Son, You Kyung</creatorcontrib><creatorcontrib>Park, Jin Ju</creatorcontrib><creatorcontrib>Sohn, Hee Sook</creatorcontrib><creatorcontrib>Choi, Jae Sue</creatorcontrib><title>Extraction and identification of three major aldose reductase inhibitors from Artemisia montana</title><title>Food and chemical toxicology</title><addtitle>Food Chem Toxicol</addtitle><description>Aldose reductase inhibitors (ARIs) provide an important therapeutic and preventive opportunity against hyperglycemia associated diabetic complications. The methanolic extracts of 12 species from the genus Artemisia exhibited significant in vitro rat lens AR (RLAR) inhibitory activities with IC50 values ranging from 0.51 to 13.45μg/mL (quercetin, 0.64μg/mL). Since the whole plant of Artemisia montana showed the highest RLAR inhibitory activity, bioassay-guided fractionation was performed to obtain ethyl acetate and n-butanol fractions. Repeated column chromatography of two active fractions, yielded fifteen compounds, including four chlorogenic acids (3,5-di-O-caffeoylquinic acid, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid), six flavonoids (apigenin, luteolin, quercetin, isoquercitrin, hyperoside, luteolin 7-rutinoside), and five coumarins (umbelliferone, scoparone, scopoletin, esculetin, and scopolin); their structures were confirmed by spectroscopic methods. 3,5-Di-O-caffeoylquinic acid and chlorogenic acid, as well as test flavonoids, displayed the most potent RLAR inhibitory activities with IC50 values ranging from 0.19 to 5.37μM. Furthermore, the HPLC profiles of the ethyl acetate and n-butanol fractions indicated that 3,5-di-O-caffeoylquinic acid, chlorogenic acid, and hyperoside, as major compounds, might play crucial roles in RLAR inhibition. The results suggest that A. montana and three key AR inhibitors therein would clearly be potential candidates as therapeutic or preventive agents for diabetic complications.</description><subject>aldehyde reductase</subject><subject>Aldehyde Reductase - antagonists & inhibitors</subject><subject>Aldose reductase</subject><subject>Animals</subject><subject>apigenin</subject><subject>Artemisia</subject><subject>Artemisia - chemistry</subject><subject>Artemisia montana</subject><subject>Biological and medical sciences</subject><subject>Caffeoylquinic acid</subject><subject>chlorogenic acid</subject><subject>Compositae</subject><subject>diabetic complications</subject><subject>ethyl acetate</subject><subject>Flavonoids - chemistry</subject><subject>Flavonoids - pharmacology</subject><subject>fractionation</subject><subject>General pharmacology</subject><subject>high performance liquid chromatography</subject><subject>HPLC</subject><subject>hyperglycemia</subject><subject>Hyperoside</subject><subject>Inhibitory Concentration 50</subject><subject>isoquercitrin</subject><subject>Lens, Crystalline - enzymology</subject><subject>luteolin</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><subject>quercetin</subject><subject>Rats</subject><subject>Republic of Korea</subject><subject>scopoletin</subject><subject>spectroscopy</subject><subject>umbelliferones</subject><issn>0278-6915</issn><issn>1873-6351</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU-PFCEQxYnRuOPqB_CifTGeZqSAppt42mzWP8kmHnTPpAYKl0l3swKz0W8v44x60xNQ-VXV4z3GngPfAAf9ZrcJrm4EP7xhw0E8YCsYB7nWsoeHbMXFMK61gf6MPSllxzkfYNCP2ZkAbsTQw4rZq-81o6sxLR0uvouelhpDdPirlEJXbzNRN-Mu5Q4nnwp1mfzeVWy3uNzGbawply7kNHcXudIcS8RuTkvFBZ-yRwGnQs9O5zm7eXf15fLD-vrT-4-XF9drp-RY19IYo2CQpMAr44OTMmgVEA0pr8loJwQfVM_Dtv1CbMmjMFwH4XQfHDp5zl4f597l9G1Ppdomw9E04UJpX-youRy56OH_pBolKClEI-FIupxKyRTsXY4z5h8WuD0EYHe2BWAPAVgA2wJoPS9O0_fbmfyfjt-ON-DVCcDicAoZFxfLX06OUhkwjXt55AImi19zY24-t0095zAobngj3h4Jar7eR8q2uEiLIx8zNVk-xX8I_QnYN6zH</recordid><startdate>20110201</startdate><enddate>20110201</enddate><creator>Jung, Hyun Ah</creator><creator>Islam, M.D. Nurul</creator><creator>Kwon, Yong Soo</creator><creator>Jin, Seong Eun</creator><creator>Son, You Kyung</creator><creator>Park, Jin Ju</creator><creator>Sohn, Hee Sook</creator><creator>Choi, Jae Sue</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7U7</scope><scope>C1K</scope></search><sort><creationdate>20110201</creationdate><title>Extraction and identification of three major aldose reductase inhibitors from Artemisia montana</title><author>Jung, Hyun Ah ; Islam, M.D. Nurul ; Kwon, Yong Soo ; Jin, Seong Eun ; Son, You Kyung ; Park, Jin Ju ; Sohn, Hee Sook ; Choi, Jae Sue</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-39994173e41d49dfc33f64faa9e4d6e96c2207450fb0002beda2906f2c65fcac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>aldehyde reductase</topic><topic>Aldehyde Reductase - antagonists & inhibitors</topic><topic>Aldose reductase</topic><topic>Animals</topic><topic>apigenin</topic><topic>Artemisia</topic><topic>Artemisia - chemistry</topic><topic>Artemisia montana</topic><topic>Biological and medical sciences</topic><topic>Caffeoylquinic acid</topic><topic>chlorogenic acid</topic><topic>Compositae</topic><topic>diabetic complications</topic><topic>ethyl acetate</topic><topic>Flavonoids - chemistry</topic><topic>Flavonoids - pharmacology</topic><topic>fractionation</topic><topic>General pharmacology</topic><topic>high performance liquid chromatography</topic><topic>HPLC</topic><topic>hyperglycemia</topic><topic>Hyperoside</topic><topic>Inhibitory Concentration 50</topic><topic>isoquercitrin</topic><topic>Lens, Crystalline - enzymology</topic><topic>luteolin</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>quercetin</topic><topic>Rats</topic><topic>Republic of Korea</topic><topic>scopoletin</topic><topic>spectroscopy</topic><topic>umbelliferones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jung, Hyun Ah</creatorcontrib><creatorcontrib>Islam, M.D. Nurul</creatorcontrib><creatorcontrib>Kwon, Yong Soo</creatorcontrib><creatorcontrib>Jin, Seong Eun</creatorcontrib><creatorcontrib>Son, You Kyung</creatorcontrib><creatorcontrib>Park, Jin Ju</creatorcontrib><creatorcontrib>Sohn, Hee Sook</creatorcontrib><creatorcontrib>Choi, Jae Sue</creatorcontrib><collection>AGRIS</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><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Food and chemical toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jung, Hyun Ah</au><au>Islam, M.D. Nurul</au><au>Kwon, Yong Soo</au><au>Jin, Seong Eun</au><au>Son, You Kyung</au><au>Park, Jin Ju</au><au>Sohn, Hee Sook</au><au>Choi, Jae Sue</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Extraction and identification of three major aldose reductase inhibitors from Artemisia montana</atitle><jtitle>Food and chemical toxicology</jtitle><addtitle>Food Chem Toxicol</addtitle><date>2011-02-01</date><risdate>2011</risdate><volume>49</volume><issue>2</issue><spage>376</spage><epage>384</epage><pages>376-384</pages><issn>0278-6915</issn><eissn>1873-6351</eissn><coden>FCTOD7</coden><abstract>Aldose reductase inhibitors (ARIs) provide an important therapeutic and preventive opportunity against hyperglycemia associated diabetic complications. The methanolic extracts of 12 species from the genus Artemisia exhibited significant in vitro rat lens AR (RLAR) inhibitory activities with IC50 values ranging from 0.51 to 13.45μg/mL (quercetin, 0.64μg/mL). Since the whole plant of Artemisia montana showed the highest RLAR inhibitory activity, bioassay-guided fractionation was performed to obtain ethyl acetate and n-butanol fractions. Repeated column chromatography of two active fractions, yielded fifteen compounds, including four chlorogenic acids (3,5-di-O-caffeoylquinic acid, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid), six flavonoids (apigenin, luteolin, quercetin, isoquercitrin, hyperoside, luteolin 7-rutinoside), and five coumarins (umbelliferone, scoparone, scopoletin, esculetin, and scopolin); their structures were confirmed by spectroscopic methods. 3,5-Di-O-caffeoylquinic acid and chlorogenic acid, as well as test flavonoids, displayed the most potent RLAR inhibitory activities with IC50 values ranging from 0.19 to 5.37μM. Furthermore, the HPLC profiles of the ethyl acetate and n-butanol fractions indicated that 3,5-di-O-caffeoylquinic acid, chlorogenic acid, and hyperoside, as major compounds, might play crucial roles in RLAR inhibition. The results suggest that A. montana and three key AR inhibitors therein would clearly be potential candidates as therapeutic or preventive agents for diabetic complications.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>21092751</pmid><doi>10.1016/j.fct.2010.11.012</doi><tpages>9</tpages></addata></record> |
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| subjects | aldehyde reductase Aldehyde Reductase - antagonists & inhibitors Aldose reductase Animals apigenin Artemisia Artemisia - chemistry Artemisia montana Biological and medical sciences Caffeoylquinic acid chlorogenic acid Compositae diabetic complications ethyl acetate Flavonoids - chemistry Flavonoids - pharmacology fractionation General pharmacology high performance liquid chromatography HPLC hyperglycemia Hyperoside Inhibitory Concentration 50 isoquercitrin Lens, Crystalline - enzymology luteolin Medical sciences Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - chemistry Plant Extracts - pharmacology quercetin Rats Republic of Korea scopoletin spectroscopy umbelliferones |
| title | Extraction and identification of three major aldose reductase inhibitors from Artemisia montana |
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