Cytotoxic xanthones from the roots of Mesua ferrea L
Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2019-01, Vol.157, p.64-70 |
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| creator | Chukaew, Arnon Saithong, Saowanit Chusri, Sasitorn Limsuwan, Surasak Watanapokasin, Ramida Voravuthikunchai, Supayang P. Chakthong, Suda |
| description | Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xanthones were elucidated based on spectroscopic methods. 5-Hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone were also confirmed by X-ray diffraction data. In addition, the isolated compounds were determined for antibacterial, antioxidant and cytotoxic activities. The known 1,5,6-trihydroxyxanthone showed cytotoxicity against A375, PC-3 and HaCaT cell lines with IC50 values of 5.73 μg/mL, 5.93 μg/mL and 8.94 μg/mL, respectively.
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•Five previously undescribed xanthones were purified from Mesua ferrea.•5-Hydroxy-1,6,7-trimethoxyxanthone exhibited weak antibacterial activity against S. aureus ATCC 23235.•1,5,6-Trihydroxyxanthone showed potent cytotoxicity against A375, PC-3 and HaCaT cell lines. |
| doi_str_mv | 10.1016/j.phytochem.2018.10.008 |
| format | Article |
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[Display omitted]
•Five previously undescribed xanthones were purified from Mesua ferrea.•5-Hydroxy-1,6,7-trimethoxyxanthone exhibited weak antibacterial activity against S. aureus ATCC 23235.•1,5,6-Trihydroxyxanthone showed potent cytotoxicity against A375, PC-3 and HaCaT cell lines.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2018.10.008</identifier><identifier>PMID: 30368220</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - pharmacology ; Calophyllaceae ; Cell Line, Tumor ; Cytotoxic activity ; Humans ; Inhibitory Concentration 50 ; Magnoliopsida - chemistry ; Mesua ferrea L ; Plant Roots - chemistry ; Xanthones ; Xanthones - chemistry ; Xanthones - pharmacology</subject><ispartof>Phytochemistry (Oxford), 2019-01, Vol.157, p.64-70</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c437t-8b6c5bd2d4d19a88c20b68147e6b7668fc417b9e660c0fa9124568ef6c11b42e3</citedby><cites>FETCH-LOGICAL-c437t-8b6c5bd2d4d19a88c20b68147e6b7668fc417b9e660c0fa9124568ef6c11b42e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2018.10.008$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30368220$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chukaew, Arnon</creatorcontrib><creatorcontrib>Saithong, Saowanit</creatorcontrib><creatorcontrib>Chusri, Sasitorn</creatorcontrib><creatorcontrib>Limsuwan, Surasak</creatorcontrib><creatorcontrib>Watanapokasin, Ramida</creatorcontrib><creatorcontrib>Voravuthikunchai, Supayang P.</creatorcontrib><creatorcontrib>Chakthong, Suda</creatorcontrib><title>Cytotoxic xanthones from the roots of Mesua ferrea L</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xanthones were elucidated based on spectroscopic methods. 5-Hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone were also confirmed by X-ray diffraction data. In addition, the isolated compounds were determined for antibacterial, antioxidant and cytotoxic activities. The known 1,5,6-trihydroxyxanthone showed cytotoxicity against A375, PC-3 and HaCaT cell lines with IC50 values of 5.73 μg/mL, 5.93 μg/mL and 8.94 μg/mL, respectively.
[Display omitted]
•Five previously undescribed xanthones were purified from Mesua ferrea.•5-Hydroxy-1,6,7-trimethoxyxanthone exhibited weak antibacterial activity against S. aureus ATCC 23235.•1,5,6-Trihydroxyxanthone showed potent cytotoxicity against A375, PC-3 and HaCaT cell lines.</description><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Calophyllaceae</subject><subject>Cell Line, Tumor</subject><subject>Cytotoxic activity</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Magnoliopsida - chemistry</subject><subject>Mesua ferrea L</subject><subject>Plant Roots - chemistry</subject><subject>Xanthones</subject><subject>Xanthones - chemistry</subject><subject>Xanthones - pharmacology</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkD1PwzAQhi0EoqXwF8AjS8LZSWxnrCq-pCIWmC3HOSupmrrYCWr_PakKXZlOuns_dA8hdwxSBkw8rNJts--9bbBLOTA1blMAdUamTMksySTAOZkCZCwpc84n5CrGFQAUhRCXZJJBJhTnMCX5Yozp_a61dGc2feM3GKkLvqN9gzR430fqHX3DOBjqMAQ0dHlNLpxZR7z5nTPy-fT4sXhJlu_Pr4v5MrF5JvtEVcIWVc3rvGalUcpyqIRiuURRSSGUszmTVYlCgAVnSsbzQih0wjJW5RyzGbk_5m6D_xow9rpro8X12mzQD1FzxkUJpSzZKJVHqQ0-xoBOb0PbmbDXDPQBmV7pEzJ9QHY4jMhG5-1vyVB1WJ98f4xGwfwowPHV7xaDjrbFjcW6DWh7Xfv235Ife0qAPA</recordid><startdate>201901</startdate><enddate>201901</enddate><creator>Chukaew, Arnon</creator><creator>Saithong, Saowanit</creator><creator>Chusri, Sasitorn</creator><creator>Limsuwan, Surasak</creator><creator>Watanapokasin, Ramida</creator><creator>Voravuthikunchai, Supayang P.</creator><creator>Chakthong, Suda</creator><general>Elsevier Ltd</general><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>201901</creationdate><title>Cytotoxic xanthones from the roots of Mesua ferrea L</title><author>Chukaew, Arnon ; Saithong, Saowanit ; Chusri, Sasitorn ; Limsuwan, Surasak ; Watanapokasin, Ramida ; Voravuthikunchai, Supayang P. ; Chakthong, Suda</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c437t-8b6c5bd2d4d19a88c20b68147e6b7668fc417b9e660c0fa9124568ef6c11b42e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Calophyllaceae</topic><topic>Cell Line, Tumor</topic><topic>Cytotoxic activity</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Magnoliopsida - chemistry</topic><topic>Mesua ferrea L</topic><topic>Plant Roots - chemistry</topic><topic>Xanthones</topic><topic>Xanthones - chemistry</topic><topic>Xanthones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chukaew, Arnon</creatorcontrib><creatorcontrib>Saithong, Saowanit</creatorcontrib><creatorcontrib>Chusri, Sasitorn</creatorcontrib><creatorcontrib>Limsuwan, Surasak</creatorcontrib><creatorcontrib>Watanapokasin, Ramida</creatorcontrib><creatorcontrib>Voravuthikunchai, Supayang P.</creatorcontrib><creatorcontrib>Chakthong, Suda</creatorcontrib><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>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chukaew, Arnon</au><au>Saithong, Saowanit</au><au>Chusri, Sasitorn</au><au>Limsuwan, Surasak</au><au>Watanapokasin, Ramida</au><au>Voravuthikunchai, Supayang P.</au><au>Chakthong, Suda</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic xanthones from the roots of Mesua ferrea L</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2019-01</date><risdate>2019</risdate><volume>157</volume><spage>64</spage><epage>70</epage><pages>64-70</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xanthones were elucidated based on spectroscopic methods. 5-Hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone were also confirmed by X-ray diffraction data. In addition, the isolated compounds were determined for antibacterial, antioxidant and cytotoxic activities. The known 1,5,6-trihydroxyxanthone showed cytotoxicity against A375, PC-3 and HaCaT cell lines with IC50 values of 5.73 μg/mL, 5.93 μg/mL and 8.94 μg/mL, respectively.
[Display omitted]
•Five previously undescribed xanthones were purified from Mesua ferrea.•5-Hydroxy-1,6,7-trimethoxyxanthone exhibited weak antibacterial activity against S. aureus ATCC 23235.•1,5,6-Trihydroxyxanthone showed potent cytotoxicity against A375, PC-3 and HaCaT cell lines.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30368220</pmid><doi>10.1016/j.phytochem.2018.10.008</doi><tpages>7</tpages></addata></record> |
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| subjects | Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology Calophyllaceae Cell Line, Tumor Cytotoxic activity Humans Inhibitory Concentration 50 Magnoliopsida - chemistry Mesua ferrea L Plant Roots - chemistry Xanthones Xanthones - chemistry Xanthones - pharmacology |
| title | Cytotoxic xanthones from the roots of Mesua ferrea L |
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