Norfriedelins A–C with Acetylcholinesterase Inhibitory Activity from Acerola Tree (Malpighia emarginata)
Three novel norfriedelanes, A–C (1–3), were isolated from the branches and roots of Malpighia emarginata. Their structures and absolute configurations were determined by 1D and 2D NMR techniques and X-ray crystallographic analysis. Norfriedelin A (possessing an α-oxo-β-lactone group) and norfriedeli...
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| Veröffentlicht in: | Organic letters 2013-04, Vol.15 (7), p.1580-1583 |
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| container_issue | 7 |
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| container_title | Organic letters |
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| creator | Liu, Jie-Qing Peng, Xing-Rong Li, Xu-Yang Li, Ting-Zhao Zhang, Wei-Ming Shi, Lei Han, Jiang Qiu, Ming-Hua |
| description | Three novel norfriedelanes, A–C (1–3), were isolated from the branches and roots of Malpighia emarginata. Their structures and absolute configurations were determined by 1D and 2D NMR techniques and X-ray crystallographic analysis. Norfriedelin A (possessing an α-oxo-β-lactone group) and norfriedelin B (with a keto-lactone group) showed acetylcholinesterase inhibitory effects with the IC50 values of 10.3 and 28.7 μM, respectively. |
| doi_str_mv | 10.1021/ol4003702 |
| format | Article |
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Their structures and absolute configurations were determined by 1D and 2D NMR techniques and X-ray crystallographic analysis. Norfriedelin A (possessing an α-oxo-β-lactone group) and norfriedelin B (with a keto-lactone group) showed acetylcholinesterase inhibitory effects with the IC50 values of 10.3 and 28.7 μM, respectively.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol4003702</identifier><identifier>PMID: 23484960</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cholinesterase Inhibitors - chemistry ; Cholinesterase Inhibitors - isolation & purification ; Cholinesterase Inhibitors - pharmacology ; Crystallography, X-Ray ; Inhibitory Concentration 50 ; Malpighiaceae - chemistry ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Triterpenes - pharmacology</subject><ispartof>Organic letters, 2013-04, Vol.15 (7), p.1580-1583</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-221991ac1d5312914f598a8f5ef50b399748bf06f0c58e0f21cdbc65e70a491a3</citedby><cites>FETCH-LOGICAL-a315t-221991ac1d5312914f598a8f5ef50b399748bf06f0c58e0f21cdbc65e70a491a3</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/ol4003702$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol4003702$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23484960$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Jie-Qing</creatorcontrib><creatorcontrib>Peng, Xing-Rong</creatorcontrib><creatorcontrib>Li, Xu-Yang</creatorcontrib><creatorcontrib>Li, Ting-Zhao</creatorcontrib><creatorcontrib>Zhang, Wei-Ming</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><creatorcontrib>Han, Jiang</creatorcontrib><creatorcontrib>Qiu, Ming-Hua</creatorcontrib><title>Norfriedelins A–C with Acetylcholinesterase Inhibitory Activity from Acerola Tree (Malpighia emarginata)</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Three novel norfriedelanes, A–C (1–3), were isolated from the branches and roots of Malpighia emarginata. Their structures and absolute configurations were determined by 1D and 2D NMR techniques and X-ray crystallographic analysis. Norfriedelin A (possessing an α-oxo-β-lactone group) and norfriedelin B (with a keto-lactone group) showed acetylcholinesterase inhibitory effects with the IC50 values of 10.3 and 28.7 μM, respectively.</description><subject>Cholinesterase Inhibitors - chemistry</subject><subject>Cholinesterase Inhibitors - isolation & purification</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Crystallography, X-Ray</subject><subject>Inhibitory Concentration 50</subject><subject>Malpighiaceae - chemistry</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EouWx4AdQNkjtImA7cR7LquJRqcCmrCPHGTeunLjYKSg7_oE_5Etw1dIVqxnNnLm6cxG6IviWYErujI4xjlJMj9CQMBqFKWb0-NAneIDOnFthTPwkP0UDGsVZnCd4iFYvxkqroAKtWhdMfr6-p8Gn6upgIqDrtaiNX4DrwHIHwaytVak6Y3u_79SH6vpAWtNsaWs0DxYWIBg9c71Wy1rxABpul6rlHR9foBPJtYPLfT1Hbw_3i-lTOH99nE0n85BHhHUhpSTPCRekYhGhOYklyzOeSQaS4TLK8zTOSokTiQXLAEtKRFWKhEGKeewPo3M02umurXnfeOtFo5wArXkLZuMKEjEWp2lGmEfHO1RY45wFWayt8o77guBiG21xiNaz13vZTdlAdSD_svTAzQ7gwhUrs7Gt__IfoV_56IBk</recordid><startdate>20130405</startdate><enddate>20130405</enddate><creator>Liu, Jie-Qing</creator><creator>Peng, Xing-Rong</creator><creator>Li, Xu-Yang</creator><creator>Li, Ting-Zhao</creator><creator>Zhang, Wei-Ming</creator><creator>Shi, Lei</creator><creator>Han, Jiang</creator><creator>Qiu, Ming-Hua</creator><general>American Chemical Society</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>20130405</creationdate><title>Norfriedelins A–C with Acetylcholinesterase Inhibitory Activity from Acerola Tree (Malpighia emarginata)</title><author>Liu, Jie-Qing ; Peng, Xing-Rong ; Li, Xu-Yang ; Li, Ting-Zhao ; Zhang, Wei-Ming ; Shi, Lei ; Han, Jiang ; Qiu, Ming-Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-221991ac1d5312914f598a8f5ef50b399748bf06f0c58e0f21cdbc65e70a491a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Cholinesterase Inhibitors - chemistry</topic><topic>Cholinesterase Inhibitors - isolation & purification</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Crystallography, X-Ray</topic><topic>Inhibitory Concentration 50</topic><topic>Malpighiaceae - chemistry</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Jie-Qing</creatorcontrib><creatorcontrib>Peng, Xing-Rong</creatorcontrib><creatorcontrib>Li, Xu-Yang</creatorcontrib><creatorcontrib>Li, Ting-Zhao</creatorcontrib><creatorcontrib>Zhang, Wei-Ming</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><creatorcontrib>Han, Jiang</creatorcontrib><creatorcontrib>Qiu, Ming-Hua</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Jie-Qing</au><au>Peng, Xing-Rong</au><au>Li, Xu-Yang</au><au>Li, Ting-Zhao</au><au>Zhang, Wei-Ming</au><au>Shi, Lei</au><au>Han, Jiang</au><au>Qiu, Ming-Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Norfriedelins A–C with Acetylcholinesterase Inhibitory Activity from Acerola Tree (Malpighia emarginata)</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-04-05</date><risdate>2013</risdate><volume>15</volume><issue>7</issue><spage>1580</spage><epage>1583</epage><pages>1580-1583</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Three novel norfriedelanes, A–C (1–3), were isolated from the branches and roots of Malpighia emarginata. Their structures and absolute configurations were determined by 1D and 2D NMR techniques and X-ray crystallographic analysis. Norfriedelin A (possessing an α-oxo-β-lactone group) and norfriedelin B (with a keto-lactone group) showed acetylcholinesterase inhibitory effects with the IC50 values of 10.3 and 28.7 μM, respectively.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23484960</pmid><doi>10.1021/ol4003702</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - isolation & purification Cholinesterase Inhibitors - pharmacology Crystallography, X-Ray Inhibitory Concentration 50 Malpighiaceae - chemistry Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology |
| title | Norfriedelins A–C with Acetylcholinesterase Inhibitory Activity from Acerola Tree (Malpighia emarginata) |
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