Isolation and Characterization of Structurally Novel Antimutagenic Flavonoids from Spinach (Spinacia oleracea)
Thirteen compounds, isolated from spinach (Spinacia oleracea), acted as antimutagens against the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in Salmonella typhimurium TA 98. The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extr...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2001-06, Vol.49 (6), p.2767-2773 |
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| creator | Edenharder, Rudolf Keller, Gernot Platt, Karl L Unger, Klaus K |
| description | Thirteen compounds, isolated from spinach (Spinacia oleracea), acted as antimutagens against the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in Salmonella typhimurium TA 98. The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extract of dry spinach (commercial product) after removal of lipophilic compounds such as chlorophylls and carotenoids by solid-phase extraction (SPE). Pure active compounds were identified by instrumental analysis including FT-IR, 1H and 13C NMR, UV−vis spectroscopy, and mass spectrometry. All of these compounds were flavonoids and related compounds that could be attributed to five groups: (A, methylenedioxyflavonol glucuronides) 5,3‘-dihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 1), 5,2‘,3‘-trihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 2), 5-hydroxy-3‘,4‘-dimethoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 3); (B, flavonol glucuronides) 5,6,3‘-trihydroxy-7,4‘-dimethoxyflavonol 3-O-β-glucuronide (compound 4), 5,6-dihydroxy-7,3‘,4‘-trimethoxyflavonol 3-O-β-glucuronide (compound 5); (C, flavonol disaccharides) 5,6,4‘-trihydroxy-7,3‘-dimethoxyflavonol 3-O-disaccharide (compound 6), 5,6,3‘,4‘-tetrahydroxy-7-methoxyflavonol 3-O-disaccharide (compounds 7 and 8); (D, flavanones) 5,8,4‘-trihydroxyflavanone (compound 9), 7,8,4‘-trihydroxyflavanone (compound 10); (E, flavonoid-related compounds) compounds 11, 12, and 13 with incompletely elucidated structures. The yield of compound 1 was 0.3%, related to dry weight, whereas the yields of compounds 2−13 ranged between 0.017 and 0.069%. IC50 values (antimutagenic potencies) of the flavonol glucuronides ranged between 24.2 and 58.2 μM, whereas the flavonol disaccharides (compounds 7 and 8), the flavanones (compounds 9 and 10), and the flavonoid-related glycosidic compounds 11−13 were only weakly active. The aglycons of compounds 7 and 8, however, were potent antimutagens (IC50 = 10.4 and 13.0 μM, respectively). Keywords: Spinach; 2-amino-3-methylimidazo[4,5-f]quinoline; flavonoids; antimutagenic activity; Salmonella/reversion assay |
| doi_str_mv | 10.1021/jf0013712 |
| format | Article |
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The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extract of dry spinach (commercial product) after removal of lipophilic compounds such as chlorophylls and carotenoids by solid-phase extraction (SPE). Pure active compounds were identified by instrumental analysis including FT-IR, 1H and 13C NMR, UV−vis spectroscopy, and mass spectrometry. All of these compounds were flavonoids and related compounds that could be attributed to five groups: (A, methylenedioxyflavonol glucuronides) 5,3‘-dihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 1), 5,2‘,3‘-trihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 2), 5-hydroxy-3‘,4‘-dimethoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 3); (B, flavonol glucuronides) 5,6,3‘-trihydroxy-7,4‘-dimethoxyflavonol 3-O-β-glucuronide (compound 4), 5,6-dihydroxy-7,3‘,4‘-trimethoxyflavonol 3-O-β-glucuronide (compound 5); (C, flavonol disaccharides) 5,6,4‘-trihydroxy-7,3‘-dimethoxyflavonol 3-O-disaccharide (compound 6), 5,6,3‘,4‘-tetrahydroxy-7-methoxyflavonol 3-O-disaccharide (compounds 7 and 8); (D, flavanones) 5,8,4‘-trihydroxyflavanone (compound 9), 7,8,4‘-trihydroxyflavanone (compound 10); (E, flavonoid-related compounds) compounds 11, 12, and 13 with incompletely elucidated structures. The yield of compound 1 was 0.3%, related to dry weight, whereas the yields of compounds 2−13 ranged between 0.017 and 0.069%. IC50 values (antimutagenic potencies) of the flavonol glucuronides ranged between 24.2 and 58.2 μM, whereas the flavonol disaccharides (compounds 7 and 8), the flavanones (compounds 9 and 10), and the flavonoid-related glycosidic compounds 11−13 were only weakly active. The aglycons of compounds 7 and 8, however, were potent antimutagens (IC50 = 10.4 and 13.0 μM, respectively). Keywords: Spinach; 2-amino-3-methylimidazo[4,5-f]quinoline; flavonoids; antimutagenic activity; Salmonella/reversion assay</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0013712</identifier><identifier>PMID: 11409964</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antimutagenic Agents - classification ; Antimutagenic Agents - isolation & purification ; Biological and medical sciences ; Carcinogenesis, carcinogens and anticarcinogens ; Chromatography, High Pressure Liquid ; Flavonoids - classification ; Flavonoids - isolation & purification ; Foods and miscellaneous ; Medical sciences ; Mutagens ; Quinolines ; Salmonella typhimurium ; Spinacia oleracea - chemistry ; Structure-Activity Relationship ; Tumors</subject><ispartof>Journal of agricultural and food chemistry, 2001-06, Vol.49 (6), p.2767-2773</ispartof><rights>Copyright © 2001 American Chemical Society</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a378t-abd653667f1b0aa77d6e9ccccb18361d44438b0fd4872f11c3e98973e0b1f09f3</citedby><cites>FETCH-LOGICAL-a378t-abd653667f1b0aa77d6e9ccccb18361d44438b0fd4872f11c3e98973e0b1f09f3</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/jf0013712$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0013712$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1047070$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11409964$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Edenharder, Rudolf</creatorcontrib><creatorcontrib>Keller, Gernot</creatorcontrib><creatorcontrib>Platt, Karl L</creatorcontrib><creatorcontrib>Unger, Klaus K</creatorcontrib><title>Isolation and Characterization of Structurally Novel Antimutagenic Flavonoids from Spinach (Spinacia oleracea)</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Thirteen compounds, isolated from spinach (Spinacia oleracea), acted as antimutagens against the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in Salmonella typhimurium TA 98. The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extract of dry spinach (commercial product) after removal of lipophilic compounds such as chlorophylls and carotenoids by solid-phase extraction (SPE). Pure active compounds were identified by instrumental analysis including FT-IR, 1H and 13C NMR, UV−vis spectroscopy, and mass spectrometry. All of these compounds were flavonoids and related compounds that could be attributed to five groups: (A, methylenedioxyflavonol glucuronides) 5,3‘-dihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 1), 5,2‘,3‘-trihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 2), 5-hydroxy-3‘,4‘-dimethoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 3); (B, flavonol glucuronides) 5,6,3‘-trihydroxy-7,4‘-dimethoxyflavonol 3-O-β-glucuronide (compound 4), 5,6-dihydroxy-7,3‘,4‘-trimethoxyflavonol 3-O-β-glucuronide (compound 5); (C, flavonol disaccharides) 5,6,4‘-trihydroxy-7,3‘-dimethoxyflavonol 3-O-disaccharide (compound 6), 5,6,3‘,4‘-tetrahydroxy-7-methoxyflavonol 3-O-disaccharide (compounds 7 and 8); (D, flavanones) 5,8,4‘-trihydroxyflavanone (compound 9), 7,8,4‘-trihydroxyflavanone (compound 10); (E, flavonoid-related compounds) compounds 11, 12, and 13 with incompletely elucidated structures. The yield of compound 1 was 0.3%, related to dry weight, whereas the yields of compounds 2−13 ranged between 0.017 and 0.069%. IC50 values (antimutagenic potencies) of the flavonol glucuronides ranged between 24.2 and 58.2 μM, whereas the flavonol disaccharides (compounds 7 and 8), the flavanones (compounds 9 and 10), and the flavonoid-related glycosidic compounds 11−13 were only weakly active. The aglycons of compounds 7 and 8, however, were potent antimutagens (IC50 = 10.4 and 13.0 μM, respectively). Keywords: Spinach; 2-amino-3-methylimidazo[4,5-f]quinoline; flavonoids; antimutagenic activity; Salmonella/reversion assay</description><subject>Antimutagenic Agents - classification</subject><subject>Antimutagenic Agents - isolation & purification</subject><subject>Biological and medical sciences</subject><subject>Carcinogenesis, carcinogens and anticarcinogens</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Flavonoids - classification</subject><subject>Flavonoids - isolation & purification</subject><subject>Foods and miscellaneous</subject><subject>Medical sciences</subject><subject>Mutagens</subject><subject>Quinolines</subject><subject>Salmonella typhimurium</subject><subject>Spinacia oleracea - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Tumors</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFu1DAQBmALgehSOPACyAeQ2kPKzDqJnWO1tFCpBcQu4mhNHJt6ydorO6koT09QVoUDvtjyfPo1-hl7iXCGsMS3WweAQuLyEVtgtYSiQlSP2QKmYaGqGo_Ys5y3AKAqCU_ZEWIJTVOXCxaucuxp8DFwCh1f3VIiM9jkf82f0fH1kEYzjIn6_p5_jHe25-dh8LtxoO82eMMve7qLIfouc5fijq_3PpC55SfzwxOPvZ1iLZ0-Z08c9dm-ONzH7OvlxWb1obj-9P5qdX5dkJBqKKjt6krUtXTYApGUXW0bM50WlaixK8tSqBZcVyq5dIhG2EY1Ulho0UHjxDE7nXNNijkn6_Q--R2le42g_3SmHzqb7KvZ7sd2Z7u_8lDSBF4fAGVDvUsUjM__JJYSJEysmJnPg_35MKb0Q9dSyEpvPq_1l1XzTd28a_Rm8m9mTybrbRxTmBr5z36_AXoPj6g</recordid><startdate>20010601</startdate><enddate>20010601</enddate><creator>Edenharder, Rudolf</creator><creator>Keller, Gernot</creator><creator>Platt, Karl L</creator><creator>Unger, Klaus K</creator><general>American Chemical Society</general><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></search><sort><creationdate>20010601</creationdate><title>Isolation and Characterization of Structurally Novel Antimutagenic Flavonoids from Spinach (Spinacia oleracea)</title><author>Edenharder, Rudolf ; Keller, Gernot ; Platt, Karl L ; Unger, Klaus K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a378t-abd653667f1b0aa77d6e9ccccb18361d44438b0fd4872f11c3e98973e0b1f09f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Antimutagenic Agents - classification</topic><topic>Antimutagenic Agents - isolation & purification</topic><topic>Biological and medical sciences</topic><topic>Carcinogenesis, carcinogens and anticarcinogens</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Flavonoids - classification</topic><topic>Flavonoids - isolation & purification</topic><topic>Foods and miscellaneous</topic><topic>Medical sciences</topic><topic>Mutagens</topic><topic>Quinolines</topic><topic>Salmonella typhimurium</topic><topic>Spinacia oleracea - chemistry</topic><topic>Structure-Activity Relationship</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Edenharder, Rudolf</creatorcontrib><creatorcontrib>Keller, Gernot</creatorcontrib><creatorcontrib>Platt, Karl L</creatorcontrib><creatorcontrib>Unger, Klaus K</creatorcontrib><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><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Edenharder, Rudolf</au><au>Keller, Gernot</au><au>Platt, Karl L</au><au>Unger, Klaus K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation and Characterization of Structurally Novel Antimutagenic Flavonoids from Spinach (Spinacia oleracea)</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2001-06-01</date><risdate>2001</risdate><volume>49</volume><issue>6</issue><spage>2767</spage><epage>2773</epage><pages>2767-2773</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Thirteen compounds, isolated from spinach (Spinacia oleracea), acted as antimutagens against the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in Salmonella typhimurium TA 98. The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extract of dry spinach (commercial product) after removal of lipophilic compounds such as chlorophylls and carotenoids by solid-phase extraction (SPE). Pure active compounds were identified by instrumental analysis including FT-IR, 1H and 13C NMR, UV−vis spectroscopy, and mass spectrometry. All of these compounds were flavonoids and related compounds that could be attributed to five groups: (A, methylenedioxyflavonol glucuronides) 5,3‘-dihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 1), 5,2‘,3‘-trihydroxy-4‘-methoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 2), 5-hydroxy-3‘,4‘-dimethoxy-6,7-methylenedioxyflavonol 3-O-β-glucuronide (compound 3); (B, flavonol glucuronides) 5,6,3‘-trihydroxy-7,4‘-dimethoxyflavonol 3-O-β-glucuronide (compound 4), 5,6-dihydroxy-7,3‘,4‘-trimethoxyflavonol 3-O-β-glucuronide (compound 5); (C, flavonol disaccharides) 5,6,4‘-trihydroxy-7,3‘-dimethoxyflavonol 3-O-disaccharide (compound 6), 5,6,3‘,4‘-tetrahydroxy-7-methoxyflavonol 3-O-disaccharide (compounds 7 and 8); (D, flavanones) 5,8,4‘-trihydroxyflavanone (compound 9), 7,8,4‘-trihydroxyflavanone (compound 10); (E, flavonoid-related compounds) compounds 11, 12, and 13 with incompletely elucidated structures. The yield of compound 1 was 0.3%, related to dry weight, whereas the yields of compounds 2−13 ranged between 0.017 and 0.069%. IC50 values (antimutagenic potencies) of the flavonol glucuronides ranged between 24.2 and 58.2 μM, whereas the flavonol disaccharides (compounds 7 and 8), the flavanones (compounds 9 and 10), and the flavonoid-related glycosidic compounds 11−13 were only weakly active. The aglycons of compounds 7 and 8, however, were potent antimutagens (IC50 = 10.4 and 13.0 μM, respectively). Keywords: Spinach; 2-amino-3-methylimidazo[4,5-f]quinoline; flavonoids; antimutagenic activity; Salmonella/reversion assay</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11409964</pmid><doi>10.1021/jf0013712</doi><tpages>7</tpages></addata></record> |
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| subjects | Antimutagenic Agents - classification Antimutagenic Agents - isolation & purification Biological and medical sciences Carcinogenesis, carcinogens and anticarcinogens Chromatography, High Pressure Liquid Flavonoids - classification Flavonoids - isolation & purification Foods and miscellaneous Medical sciences Mutagens Quinolines Salmonella typhimurium Spinacia oleracea - chemistry Structure-Activity Relationship Tumors |
| title | Isolation and Characterization of Structurally Novel Antimutagenic Flavonoids from Spinach (Spinacia oleracea) |
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