A New DNA-Intercalative Cytotoxic Allylic Xanthone from Swertia corymbosa
Phytochemical investigation of the CHCl3 fraction of Swertia corymbosa resulted in the isolation of a new 3‐allyl‐2,8‐dihydroxy‐1,6‐dimethoxy‐9H‐xanthen‐9‐one (1), along with four known xanthones, gentiacaulein (3), norswertianin (4), 1,3,6,8‐tetrahydroxyxanthone (5), and 1,3‐dihydroxyxanthone (6)....
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| Veröffentlicht in: | Chemistry & biodiversity 2015-03, Vol.12 (3), p.358-370 |
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| creator | Uvarani, Chokkalingam Arumugasamy, Karuppannan Chandraprakash, Kumarasamy Sankaran, Mathan Ata, Athar Mohan, Palathurai Subramaniam |
| description | Phytochemical investigation of the CHCl3 fraction of Swertia corymbosa resulted in the isolation of a new 3‐allyl‐2,8‐dihydroxy‐1,6‐dimethoxy‐9H‐xanthen‐9‐one (1), along with four known xanthones, gentiacaulein (3), norswertianin (4), 1,3,6,8‐tetrahydroxyxanthone (5), and 1,3‐dihydroxyxanthone (6). Structure of compound 1 was elucidated with the aid of IR, UV, NMR, and MS data, and chemical transformation via new allyloxy xanthone derivative (2). Compounds 1–6 exhibited various levels of antioxidant and anti‐α‐glucosidase activities. Absorption and fluorescence spectroscopic studies on 1–6 indicated that these compounds could interact with calf thymus DNA (CT‐DNA) through intercalation and with bovine serum albumin (BSA) in a static quenching process. Compound 1 was found to be significantly cytotoxic against human cancer cell lines HeLa, HCT116, and AGS, and weakly active against normal NIH 3T3 cell line. |
| doi_str_mv | 10.1002/cbdv.201400055 |
| format | Article |
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Structure of compound 1 was elucidated with the aid of IR, UV, NMR, and MS data, and chemical transformation via new allyloxy xanthone derivative (2). Compounds 1–6 exhibited various levels of antioxidant and anti‐α‐glucosidase activities. Absorption and fluorescence spectroscopic studies on 1–6 indicated that these compounds could interact with calf thymus DNA (CT‐DNA) through intercalation and with bovine serum albumin (BSA) in a static quenching process. Compound 1 was found to be significantly cytotoxic against human cancer cell lines HeLa, HCT116, and AGS, and weakly active against normal NIH 3T3 cell line.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.201400055</identifier><identifier>PMID: 25766909</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject><![CDATA[alpha-Glucosidases - metabolism ; Animals ; Anti-α-glucosidase activity ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Antioxidant activity ; Antioxidants - chemistry ; Antioxidants - isolation & purification ; Antioxidants - pharmacology ; Cattle ; Cell Line, Tumor ; Cytotoxic activity ; Cytotoxicity ; Deoxyribonucleic acid ; DNA ; DNA - metabolism ; Glycoside Hydrolase Inhibitors - chemistry ; Glycoside Hydrolase Inhibitors - isolation & purification ; Glycoside Hydrolase Inhibitors - pharmacology ; Humans ; Intercalating Agents - chemistry ; Intercalating Agents - isolation & purification ; Intercalating Agents - pharmacology ; Mice ; Neoplasms - drug therapy ; NIH 3T3 Cells ; Plant Extracts - chemistry ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; Protein binding ; Swertia ; Swertia - chemistry ; Swertia corymbosa ; Xanthones ; Xanthones - chemistry ; Xanthones - isolation & purification ; Xanthones - pharmacology]]></subject><ispartof>Chemistry & biodiversity, 2015-03, Vol.12 (3), p.358-370</ispartof><rights>Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich</rights><rights>Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.</rights><rights>Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zurich</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5105-c348699fec90c9f9a71f48eb168597a95a54ec5659d04584d7222d524b4e2ed33</citedby><cites>FETCH-LOGICAL-c5105-c348699fec90c9f9a71f48eb168597a95a54ec5659d04584d7222d524b4e2ed33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.201400055$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.201400055$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25766909$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Uvarani, Chokkalingam</creatorcontrib><creatorcontrib>Arumugasamy, Karuppannan</creatorcontrib><creatorcontrib>Chandraprakash, Kumarasamy</creatorcontrib><creatorcontrib>Sankaran, Mathan</creatorcontrib><creatorcontrib>Ata, Athar</creatorcontrib><creatorcontrib>Mohan, Palathurai Subramaniam</creatorcontrib><title>A New DNA-Intercalative Cytotoxic Allylic Xanthone from Swertia corymbosa</title><title>Chemistry & biodiversity</title><addtitle>Chemistry & Biodiversity</addtitle><description>Phytochemical investigation of the CHCl3 fraction of Swertia corymbosa resulted in the isolation of a new 3‐allyl‐2,8‐dihydroxy‐1,6‐dimethoxy‐9H‐xanthen‐9‐one (1), along with four known xanthones, gentiacaulein (3), norswertianin (4), 1,3,6,8‐tetrahydroxyxanthone (5), and 1,3‐dihydroxyxanthone (6). Structure of compound 1 was elucidated with the aid of IR, UV, NMR, and MS data, and chemical transformation via new allyloxy xanthone derivative (2). Compounds 1–6 exhibited various levels of antioxidant and anti‐α‐glucosidase activities. Absorption and fluorescence spectroscopic studies on 1–6 indicated that these compounds could interact with calf thymus DNA (CT‐DNA) through intercalation and with bovine serum albumin (BSA) in a static quenching process. Compound 1 was found to be significantly cytotoxic against human cancer cell lines HeLa, HCT116, and AGS, and weakly active against normal NIH 3T3 cell line.</description><subject>alpha-Glucosidases - metabolism</subject><subject>Animals</subject><subject>Anti-α-glucosidase activity</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Antioxidant activity</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - isolation & purification</subject><subject>Antioxidants - pharmacology</subject><subject>Cattle</subject><subject>Cell Line, Tumor</subject><subject>Cytotoxic activity</subject><subject>Cytotoxicity</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA - metabolism</subject><subject>Glycoside Hydrolase Inhibitors - chemistry</subject><subject>Glycoside Hydrolase Inhibitors - isolation & purification</subject><subject>Glycoside Hydrolase Inhibitors - pharmacology</subject><subject>Humans</subject><subject>Intercalating Agents - chemistry</subject><subject>Intercalating Agents - isolation & purification</subject><subject>Intercalating Agents - pharmacology</subject><subject>Mice</subject><subject>Neoplasms - drug therapy</subject><subject>NIH 3T3 Cells</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>Protein binding</subject><subject>Swertia</subject><subject>Swertia - chemistry</subject><subject>Swertia corymbosa</subject><subject>Xanthones</subject><subject>Xanthones - chemistry</subject><subject>Xanthones - isolation & purification</subject><subject>Xanthones - pharmacology</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0UtP4zAUBWBrBBpes2WJIrFhk2I7tmMvSztABRTxGGBnOc6NCCQxY6eU_HtSFSo0G2Z1r6zvHsk6CO0SPCAY00Ob5a8DignDGHP-A20SQWhMpMRrqz2lG2grhKfe9-_yJ9qgPBVCYbWJJsNoCvNoPB3Gk6YFb01l2vIVolHXuta9lTYaVlVX9fPBNO2jayAqvKujmzn4tjSRdb6rMxfMDlovTBXg18fcRn-Of9-OTuPzy5PJaHgeW04wj23CpFCqAKuwVYUyKSmYhIwIyVVqFDecgeWCqxwzLlmeUkpzTlnGgEKeJNvoYJn74t3fGYRW12WwUFWmATcLmgghKeM0Vf9DGSVYYtLT_X_ok5v5pv_IQlEuREJprwZLZb0LwUOhX3xZG99pgvWiD73oQ6_66A_2PmJnWQ35in8W0AO1BPOygu6bOD06Gt99DY-Xt2Vo4W11a_yzFmmScn0_PdHXV-MLyY_PNEveAY1Io0g</recordid><startdate>201503</startdate><enddate>201503</enddate><creator>Uvarani, Chokkalingam</creator><creator>Arumugasamy, Karuppannan</creator><creator>Chandraprakash, Kumarasamy</creator><creator>Sankaran, Mathan</creator><creator>Ata, Athar</creator><creator>Mohan, Palathurai Subramaniam</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><scope>7ST</scope><scope>7U6</scope><scope>C1K</scope></search><sort><creationdate>201503</creationdate><title>A New DNA-Intercalative Cytotoxic Allylic Xanthone from Swertia corymbosa</title><author>Uvarani, Chokkalingam ; Arumugasamy, Karuppannan ; Chandraprakash, Kumarasamy ; Sankaran, Mathan ; Ata, Athar ; Mohan, Palathurai Subramaniam</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5105-c348699fec90c9f9a71f48eb168597a95a54ec5659d04584d7222d524b4e2ed33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>alpha-Glucosidases - metabolism</topic><topic>Animals</topic><topic>Anti-α-glucosidase activity</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Antioxidant activity</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - isolation & purification</topic><topic>Antioxidants - pharmacology</topic><topic>Cattle</topic><topic>Cell Line, Tumor</topic><topic>Cytotoxic activity</topic><topic>Cytotoxicity</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA - metabolism</topic><topic>Glycoside Hydrolase Inhibitors - chemistry</topic><topic>Glycoside Hydrolase Inhibitors - isolation & purification</topic><topic>Glycoside Hydrolase Inhibitors - pharmacology</topic><topic>Humans</topic><topic>Intercalating Agents - chemistry</topic><topic>Intercalating Agents - isolation & purification</topic><topic>Intercalating Agents - pharmacology</topic><topic>Mice</topic><topic>Neoplasms - drug therapy</topic><topic>NIH 3T3 Cells</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>Protein binding</topic><topic>Swertia</topic><topic>Swertia - chemistry</topic><topic>Swertia corymbosa</topic><topic>Xanthones</topic><topic>Xanthones - chemistry</topic><topic>Xanthones - isolation & purification</topic><topic>Xanthones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uvarani, Chokkalingam</creatorcontrib><creatorcontrib>Arumugasamy, Karuppannan</creatorcontrib><creatorcontrib>Chandraprakash, Kumarasamy</creatorcontrib><creatorcontrib>Sankaran, Mathan</creatorcontrib><creatorcontrib>Ata, Athar</creatorcontrib><creatorcontrib>Mohan, Palathurai Subramaniam</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uvarani, Chokkalingam</au><au>Arumugasamy, Karuppannan</au><au>Chandraprakash, Kumarasamy</au><au>Sankaran, Mathan</au><au>Ata, Athar</au><au>Mohan, Palathurai Subramaniam</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A New DNA-Intercalative Cytotoxic Allylic Xanthone from Swertia corymbosa</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chemistry & Biodiversity</addtitle><date>2015-03</date><risdate>2015</risdate><volume>12</volume><issue>3</issue><spage>358</spage><epage>370</epage><pages>358-370</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>Phytochemical investigation of the CHCl3 fraction of Swertia corymbosa resulted in the isolation of a new 3‐allyl‐2,8‐dihydroxy‐1,6‐dimethoxy‐9H‐xanthen‐9‐one (1), along with four known xanthones, gentiacaulein (3), norswertianin (4), 1,3,6,8‐tetrahydroxyxanthone (5), and 1,3‐dihydroxyxanthone (6). Structure of compound 1 was elucidated with the aid of IR, UV, NMR, and MS data, and chemical transformation via new allyloxy xanthone derivative (2). Compounds 1–6 exhibited various levels of antioxidant and anti‐α‐glucosidase activities. Absorption and fluorescence spectroscopic studies on 1–6 indicated that these compounds could interact with calf thymus DNA (CT‐DNA) through intercalation and with bovine serum albumin (BSA) in a static quenching process. Compound 1 was found to be significantly cytotoxic against human cancer cell lines HeLa, HCT116, and AGS, and weakly active against normal NIH 3T3 cell line.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><pmid>25766909</pmid><doi>10.1002/cbdv.201400055</doi><tpages>13</tpages></addata></record> |
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| ispartof | Chemistry & biodiversity, 2015-03, Vol.12 (3), p.358-370 |
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| subjects | alpha-Glucosidases - metabolism Animals Anti-α-glucosidase activity Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Antioxidant activity Antioxidants - chemistry Antioxidants - isolation & purification Antioxidants - pharmacology Cattle Cell Line, Tumor Cytotoxic activity Cytotoxicity Deoxyribonucleic acid DNA DNA - metabolism Glycoside Hydrolase Inhibitors - chemistry Glycoside Hydrolase Inhibitors - isolation & purification Glycoside Hydrolase Inhibitors - pharmacology Humans Intercalating Agents - chemistry Intercalating Agents - isolation & purification Intercalating Agents - pharmacology Mice Neoplasms - drug therapy NIH 3T3 Cells Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology Protein binding Swertia Swertia - chemistry Swertia corymbosa Xanthones Xanthones - chemistry Xanthones - isolation & purification Xanthones - pharmacology |
| title | A New DNA-Intercalative Cytotoxic Allylic Xanthone from Swertia corymbosa |
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