A New Flavanone Glycoside from the Dried Immature Fruits of Poncirus trifoliata
A new flavanone glycoside, (2R)-5-hydroxy-4′-methoxyflavanone-7-O-{β-glucopyranosyl-(1→2)-β-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). Th...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2007/08/01, Vol.55(8), pp.1270-1273 |
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| container_title | Chemical & Pharmaceutical Bulletin |
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| creator | Han, Ah-Reum Kim, Jong-Bin Lee, Jun Nam, Joo-Won Lee, Ik-Soo Shim, Chang-Koo Lee, Kyung-Tae Seo, Eun-Kyoung |
| description | A new flavanone glycoside, (2R)-5-hydroxy-4′-methoxyflavanone-7-O-{β-glucopyranosyl-(1→2)-β-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E2 (PGE2) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells. |
| doi_str_mv | 10.1248/cpb.55.1270 |
| format | Article |
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The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E2 (PGE2) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.55.1270</identifier><identifier>PMID: 17666859</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Cell Survival - drug effects ; Dinoprostone - biosynthesis ; Flavanones - chemistry ; Flavanones - pharmacology ; Fruit - chemistry ; Glycosides - chemistry ; Glycosides - isolation & purification ; Glycosides - pharmacology ; interleukin-6 ; Interleukin-6 - antagonists & inhibitors ; Interleukin-6 - biosynthesis ; Lipopolysaccharides - antagonists & inhibitors ; Lipopolysaccharides - toxicity ; Macrophages - drug effects ; Macrophages - metabolism ; Magnetic Resonance Spectroscopy ; Mice ; new flavanone ; Poncirus - chemistry ; Poncirus trifoliata ; Prostaglandin Antagonists - pharmacology ; prostaglandin E2 ; Reverse Transcriptase Polymerase Chain Reaction ; RNA, Messenger - biosynthesis ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet ; Tetrazolium Salts ; Thiazoles</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2007/08/01, Vol.55(8), pp.1270-1273</ispartof><rights>2007 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2007</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c622t-706c59e3df8e330eeb6d74ddcf92702deaca9a96af19ccff73d73fedb29d7ebf3</citedby><cites>FETCH-LOGICAL-c622t-706c59e3df8e330eeb6d74ddcf92702deaca9a96af19ccff73d73fedb29d7ebf3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17666859$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Ah-Reum</creatorcontrib><creatorcontrib>Kim, Jong-Bin</creatorcontrib><creatorcontrib>Lee, Jun</creatorcontrib><creatorcontrib>Nam, Joo-Won</creatorcontrib><creatorcontrib>Lee, Ik-Soo</creatorcontrib><creatorcontrib>Shim, Chang-Koo</creatorcontrib><creatorcontrib>Lee, Kyung-Tae</creatorcontrib><creatorcontrib>Seo, Eun-Kyoung</creatorcontrib><creatorcontrib>Ewha Romans University</creatorcontrib><creatorcontrib>cCollege of Pharmacy and Research Institute of Drug Development</creatorcontrib><creatorcontrib>bCollege of Pharmacy</creatorcontrib><creatorcontrib>Kyung-Hee University</creatorcontrib><creatorcontrib>College of Pharmacy</creatorcontrib><creatorcontrib>aCollege of Pharmacy and Center for Cell Signaling & Drug Discovery Research</creatorcontrib><creatorcontrib>dDepartment of Pharmaceutics</creatorcontrib><creatorcontrib>Chonnam National University</creatorcontrib><creatorcontrib>Seoul National University</creatorcontrib><title>A New Flavanone Glycoside from the Dried Immature Fruits of Poncirus trifoliata</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A new flavanone glycoside, (2R)-5-hydroxy-4′-methoxyflavanone-7-O-{β-glucopyranosyl-(1→2)-β-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E2 (PGE2) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.</description><subject>Animals</subject><subject>Cell Survival - drug effects</subject><subject>Dinoprostone - biosynthesis</subject><subject>Flavanones - chemistry</subject><subject>Flavanones - pharmacology</subject><subject>Fruit - chemistry</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - isolation & purification</subject><subject>Glycosides - pharmacology</subject><subject>interleukin-6</subject><subject>Interleukin-6 - antagonists & inhibitors</subject><subject>Interleukin-6 - biosynthesis</subject><subject>Lipopolysaccharides - antagonists & inhibitors</subject><subject>Lipopolysaccharides - toxicity</subject><subject>Macrophages - drug effects</subject><subject>Macrophages - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mice</subject><subject>new flavanone</subject><subject>Poncirus - chemistry</subject><subject>Poncirus trifoliata</subject><subject>Prostaglandin Antagonists - pharmacology</subject><subject>prostaglandin E2</subject><subject>Reverse Transcriptase Polymerase Chain Reaction</subject><subject>RNA, Messenger - biosynthesis</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Tetrazolium Salts</subject><subject>Thiazoles</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkEFv1DAQhS0EokvhxB1Z4ohSJnZsJzeqwpZKFeUAZ8uxx6xXSbzYCaj_Hm-ztJcZS_P5vZlHyNsaLmrWtB_tob8QorwVPCObmjeqEozx52QDAF3FuORn5FXOewAmQPGX5KxWUspWdBtyd0m_4V-6HcwfM8UJ6fVwb2MODqlPcaTzDunnFNDRm3E085KQbtMS5kyjp9_jZENaMp1T8HEIZjavyQtvhoxvTv2c_Nx--XH1tbq9u765urytrGRsrhRIKzrkzrfIOSD20qnGOeu7cgZzaKzpTCeNrztrvVfcKe7R9axzCnvPz8n7VfeQ4u8F86z3cUlTsdR1I6GBRjZtoT6slE0x54ReH1IYTbrXNehjeLqEp4XQx_AK_e6kufQjuif2lFYBtitQpsGaIU5DmPDJ2WZldzgGzQCUBhACWg0cHuSPhUsleS2L0KdVaJ9n8wsfnUyagx3w_1btWh5-P452Jmmc-D_nuZho</recordid><startdate>20070801</startdate><enddate>20070801</enddate><creator>Han, Ah-Reum</creator><creator>Kim, Jong-Bin</creator><creator>Lee, Jun</creator><creator>Nam, Joo-Won</creator><creator>Lee, Ik-Soo</creator><creator>Shim, Chang-Koo</creator><creator>Lee, Kyung-Tae</creator><creator>Seo, Eun-Kyoung</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>20070801</creationdate><title>A New Flavanone Glycoside from the Dried Immature Fruits of Poncirus trifoliata</title><author>Han, Ah-Reum ; Kim, Jong-Bin ; Lee, Jun ; Nam, Joo-Won ; Lee, Ik-Soo ; Shim, Chang-Koo ; Lee, Kyung-Tae ; Seo, Eun-Kyoung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c622t-706c59e3df8e330eeb6d74ddcf92702deaca9a96af19ccff73d73fedb29d7ebf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Cell Survival - drug effects</topic><topic>Dinoprostone - biosynthesis</topic><topic>Flavanones - chemistry</topic><topic>Flavanones - pharmacology</topic><topic>Fruit - chemistry</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - isolation & purification</topic><topic>Glycosides - pharmacology</topic><topic>interleukin-6</topic><topic>Interleukin-6 - antagonists & inhibitors</topic><topic>Interleukin-6 - biosynthesis</topic><topic>Lipopolysaccharides - antagonists & inhibitors</topic><topic>Lipopolysaccharides - toxicity</topic><topic>Macrophages - drug effects</topic><topic>Macrophages - metabolism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mice</topic><topic>new flavanone</topic><topic>Poncirus - chemistry</topic><topic>Poncirus trifoliata</topic><topic>Prostaglandin Antagonists - pharmacology</topic><topic>prostaglandin E2</topic><topic>Reverse Transcriptase Polymerase Chain Reaction</topic><topic>RNA, Messenger - biosynthesis</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Tetrazolium Salts</topic><topic>Thiazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Ah-Reum</creatorcontrib><creatorcontrib>Kim, Jong-Bin</creatorcontrib><creatorcontrib>Lee, Jun</creatorcontrib><creatorcontrib>Nam, Joo-Won</creatorcontrib><creatorcontrib>Lee, Ik-Soo</creatorcontrib><creatorcontrib>Shim, Chang-Koo</creatorcontrib><creatorcontrib>Lee, Kyung-Tae</creatorcontrib><creatorcontrib>Seo, Eun-Kyoung</creatorcontrib><creatorcontrib>Ewha Romans University</creatorcontrib><creatorcontrib>cCollege of Pharmacy and Research Institute of Drug Development</creatorcontrib><creatorcontrib>bCollege of Pharmacy</creatorcontrib><creatorcontrib>Kyung-Hee University</creatorcontrib><creatorcontrib>College of Pharmacy</creatorcontrib><creatorcontrib>aCollege of Pharmacy and Center for Cell Signaling & Drug Discovery Research</creatorcontrib><creatorcontrib>dDepartment of Pharmaceutics</creatorcontrib><creatorcontrib>Chonnam National University</creatorcontrib><creatorcontrib>Seoul National University</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Ah-Reum</au><au>Kim, Jong-Bin</au><au>Lee, Jun</au><au>Nam, Joo-Won</au><au>Lee, Ik-Soo</au><au>Shim, Chang-Koo</au><au>Lee, Kyung-Tae</au><au>Seo, Eun-Kyoung</au><aucorp>Ewha Romans University</aucorp><aucorp>cCollege of Pharmacy and Research Institute of Drug Development</aucorp><aucorp>bCollege of Pharmacy</aucorp><aucorp>Kyung-Hee University</aucorp><aucorp>College of Pharmacy</aucorp><aucorp>aCollege of Pharmacy and Center for Cell Signaling & Drug Discovery Research</aucorp><aucorp>dDepartment of Pharmaceutics</aucorp><aucorp>Chonnam National University</aucorp><aucorp>Seoul National University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A New Flavanone Glycoside from the Dried Immature Fruits of Poncirus trifoliata</atitle><jtitle>Chemical & Pharmaceutical Bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2007-08-01</date><risdate>2007</risdate><volume>55</volume><issue>8</issue><spage>1270</spage><epage>1273</epage><pages>1270-1273</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A new flavanone glycoside, (2R)-5-hydroxy-4′-methoxyflavanone-7-O-{β-glucopyranosyl-(1→2)-β-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E2 (PGE2) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>17666859</pmid><doi>10.1248/cpb.55.1270</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Cell Survival - drug effects Dinoprostone - biosynthesis Flavanones - chemistry Flavanones - pharmacology Fruit - chemistry Glycosides - chemistry Glycosides - isolation & purification Glycosides - pharmacology interleukin-6 Interleukin-6 - antagonists & inhibitors Interleukin-6 - biosynthesis Lipopolysaccharides - antagonists & inhibitors Lipopolysaccharides - toxicity Macrophages - drug effects Macrophages - metabolism Magnetic Resonance Spectroscopy Mice new flavanone Poncirus - chemistry Poncirus trifoliata Prostaglandin Antagonists - pharmacology prostaglandin E2 Reverse Transcriptase Polymerase Chain Reaction RNA, Messenger - biosynthesis Spectrophotometry, Infrared Spectrophotometry, Ultraviolet Tetrazolium Salts Thiazoles |
| title | A New Flavanone Glycoside from the Dried Immature Fruits of Poncirus trifoliata |
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