Officimalonic acids A−H, lanostane triterpenes from the fruiting bodies of Fomes officinalis
Phytochemical investigation of the methanolic extract of the fruiting bodies of Fomes officinalis led to the isolation of eight 24-methyl-lanostane triterpenes named officimalonic acids A−H, along with one known lanostane triterpene. Their structures were elucidated based on the analysis of spectros...
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description | Phytochemical investigation of the methanolic extract of the fruiting bodies of Fomes officinalis led to the isolation of eight 24-methyl-lanostane triterpenes named officimalonic acids A−H, along with one known lanostane triterpene. Their structures were elucidated based on the analysis of spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism. Officimalonic acid A represents a previously unknown triterpene type with a 24-methyl-7(8 → 9)abeo-lanostane skeleton, and all of the compounds possessed a malonate half-ester moiety at C-3. Anti-inflammatory assay revealed that officimalonic acids D, E, G, H, and fomitopsin A showed potent inhibitory effects (IC50 = 5.1–8.9 μM) on nitric oxide production in lipopolysaccharide-induced RAW264.7 cells. Officimalonic acids E, G, H showed moderate cytotoxicity against H460, HepG2 and BGC-823 human cell lines.
Eight 24-methyl-lanostane triterpenes, officimalonic acids A−H, were isolated and identified from the fruiting bodies of Fomes officinalis. Some of them showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells. [Display omitted]
•Eight 24-methyl-lanostane triterpenes were isolated and identified from fruiting bodies of Fomes officinalis.•One of them has a 24-methyl-7(8 → 9)abeo-lanostane skeleton.•All of the compounds possessed a malonate half-ester moiety.•Some of the compounds showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells. |
doi_str_mv | 10.1016/j.phytochem.2016.05.004 |
format | Article |
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Eight 24-methyl-lanostane triterpenes, officimalonic acids A−H, were isolated and identified from the fruiting bodies of Fomes officinalis. Some of them showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells. [Display omitted]
•Eight 24-methyl-lanostane triterpenes were isolated and identified from fruiting bodies of Fomes officinalis.•One of them has a 24-methyl-7(8 → 9)abeo-lanostane skeleton.•All of the compounds possessed a malonate half-ester moiety.•Some of the compounds showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2016.05.004</identifier><identifier>PMID: 27216472</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Anti-inflammatory ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - isolation & purification ; Anti-Inflammatory Agents - pharmacology ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Coriolaceae - chemistry ; Crystallography, X-Ray ; Cytotoxicity ; Drug Screening Assays, Antitumor ; Fomes officinalis ; Fruiting Bodies, Fungal - chemistry ; Hep G2 Cells ; Humans ; Inhibitory Concentration 50 ; Lanostane triterpene ; Lanosterol - analogs & derivatives ; Lanosterol - chemistry ; Lanosterol - isolation & purification ; Lanosterol - pharmacology ; Mice ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Polyporaceae ; Structure-Activity Relationship ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Triterpenes - pharmacology</subject><ispartof>Phytochemistry (Oxford), 2016-10, Vol.130, p.193-200</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c437t-6f73e9fb358a0a69c5a66f2fc8b1d8526c8a6a731c92eda493e5efe0333c761e3</citedby><cites>FETCH-LOGICAL-c437t-6f73e9fb358a0a69c5a66f2fc8b1d8526c8a6a731c92eda493e5efe0333c761e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0031942216300930$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27216472$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Jianxin</creatorcontrib><creatorcontrib>Li, Liya</creatorcontrib><creatorcontrib>Zhong, Jialiang</creatorcontrib><creatorcontrib>Tohtaton, Zeynep</creatorcontrib><creatorcontrib>Ren, Qing</creatorcontrib><creatorcontrib>Han, Li</creatorcontrib><creatorcontrib>Huang, Xueshi</creatorcontrib><creatorcontrib>Yuan, Tao</creatorcontrib><title>Officimalonic acids A−H, lanostane triterpenes from the fruiting bodies of Fomes officinalis</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Phytochemical investigation of the methanolic extract of the fruiting bodies of Fomes officinalis led to the isolation of eight 24-methyl-lanostane triterpenes named officimalonic acids A−H, along with one known lanostane triterpene. Their structures were elucidated based on the analysis of spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism. Officimalonic acid A represents a previously unknown triterpene type with a 24-methyl-7(8 → 9)abeo-lanostane skeleton, and all of the compounds possessed a malonate half-ester moiety at C-3. Anti-inflammatory assay revealed that officimalonic acids D, E, G, H, and fomitopsin A showed potent inhibitory effects (IC50 = 5.1–8.9 μM) on nitric oxide production in lipopolysaccharide-induced RAW264.7 cells. Officimalonic acids E, G, H showed moderate cytotoxicity against H460, HepG2 and BGC-823 human cell lines.
Eight 24-methyl-lanostane triterpenes, officimalonic acids A−H, were isolated and identified from the fruiting bodies of Fomes officinalis. Some of them showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells. [Display omitted]
•Eight 24-methyl-lanostane triterpenes were isolated and identified from fruiting bodies of Fomes officinalis.•One of them has a 24-methyl-7(8 → 9)abeo-lanostane skeleton.•All of the compounds possessed a malonate half-ester moiety.•Some of the compounds showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells.</description><subject>Animals</subject><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - isolation & purification</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Coriolaceae - chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fomes officinalis</subject><subject>Fruiting Bodies, Fungal - chemistry</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Lanostane triterpene</subject><subject>Lanosterol - analogs & derivatives</subject><subject>Lanosterol - chemistry</subject><subject>Lanosterol - isolation & purification</subject><subject>Lanosterol - pharmacology</subject><subject>Mice</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Polyporaceae</subject><subject>Structure-Activity Relationship</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFO3DAQhq2qqCy0rwA59tCkYzu2k-MKlVIJiUu51vI6465XSbzYXiTeoGcekSfBy1KunGY088_8-j9Czik0FKj8vmm264cc7BqnhpVBA6IBaD-QBe0Ur7kC-EgWAJzWfcvYMTlJaQMAQkj5iRwzxahsFVuQPzfOeesnM4bZ28pYP6Rq-fTv8epbNZo5pGxmrHL0GeMWZ0yVi2Gq8hpLs_PZz3-rVRh8WQRXXYbppdm_nM3o02dy5MyY8MtrPSW3lz9-X1zV1zc_f10sr2vbcpVr6RTH3q246AwY2VthpHTM2W5Fh04waTsjjeLU9gwH0_YcBToEzrlVkiI_JV8Pf7cx3O0wZT35ZHEsETDskqYdFVxRxqFI1UFqY0gpotPbWPLHB01B7-HqjX6Dq_dwNQhd4JbLs1eT3WrC4e3uP80iWB4EWKLee4w6WY-zxcFHtFkPwb9r8gxvMpGE</recordid><startdate>201610</startdate><enddate>201610</enddate><creator>Han, Jianxin</creator><creator>Li, Liya</creator><creator>Zhong, Jialiang</creator><creator>Tohtaton, Zeynep</creator><creator>Ren, Qing</creator><creator>Han, Li</creator><creator>Huang, Xueshi</creator><creator>Yuan, Tao</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>201610</creationdate><title>Officimalonic acids A−H, lanostane triterpenes from the fruiting bodies of Fomes officinalis</title><author>Han, Jianxin ; Li, Liya ; Zhong, Jialiang ; Tohtaton, Zeynep ; Ren, Qing ; Han, Li ; Huang, Xueshi ; Yuan, Tao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c437t-6f73e9fb358a0a69c5a66f2fc8b1d8526c8a6a731c92eda493e5efe0333c761e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - isolation & purification</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Coriolaceae - chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fomes officinalis</topic><topic>Fruiting Bodies, Fungal - chemistry</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Lanostane triterpene</topic><topic>Lanosterol - analogs & derivatives</topic><topic>Lanosterol - chemistry</topic><topic>Lanosterol - isolation & purification</topic><topic>Lanosterol - pharmacology</topic><topic>Mice</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Polyporaceae</topic><topic>Structure-Activity Relationship</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Jianxin</creatorcontrib><creatorcontrib>Li, Liya</creatorcontrib><creatorcontrib>Zhong, Jialiang</creatorcontrib><creatorcontrib>Tohtaton, Zeynep</creatorcontrib><creatorcontrib>Ren, Qing</creatorcontrib><creatorcontrib>Han, Li</creatorcontrib><creatorcontrib>Huang, Xueshi</creatorcontrib><creatorcontrib>Yuan, Tao</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>Han, Jianxin</au><au>Li, Liya</au><au>Zhong, Jialiang</au><au>Tohtaton, Zeynep</au><au>Ren, Qing</au><au>Han, Li</au><au>Huang, Xueshi</au><au>Yuan, Tao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Officimalonic acids A−H, lanostane triterpenes from the fruiting bodies of Fomes officinalis</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2016-10</date><risdate>2016</risdate><volume>130</volume><spage>193</spage><epage>200</epage><pages>193-200</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Phytochemical investigation of the methanolic extract of the fruiting bodies of Fomes officinalis led to the isolation of eight 24-methyl-lanostane triterpenes named officimalonic acids A−H, along with one known lanostane triterpene. Their structures were elucidated based on the analysis of spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism. Officimalonic acid A represents a previously unknown triterpene type with a 24-methyl-7(8 → 9)abeo-lanostane skeleton, and all of the compounds possessed a malonate half-ester moiety at C-3. Anti-inflammatory assay revealed that officimalonic acids D, E, G, H, and fomitopsin A showed potent inhibitory effects (IC50 = 5.1–8.9 μM) on nitric oxide production in lipopolysaccharide-induced RAW264.7 cells. Officimalonic acids E, G, H showed moderate cytotoxicity against H460, HepG2 and BGC-823 human cell lines.
Eight 24-methyl-lanostane triterpenes, officimalonic acids A−H, were isolated and identified from the fruiting bodies of Fomes officinalis. Some of them showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells. [Display omitted]
•Eight 24-methyl-lanostane triterpenes were isolated and identified from fruiting bodies of Fomes officinalis.•One of them has a 24-methyl-7(8 → 9)abeo-lanostane skeleton.•All of the compounds possessed a malonate half-ester moiety.•Some of the compounds showed potent inhibitory effects on NO production in LPS-induced RAW264.7 cells.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>27216472</pmid><doi>10.1016/j.phytochem.2016.05.004</doi><tpages>8</tpages></addata></record> |
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subjects | Animals Anti-inflammatory Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - isolation & purification Anti-Inflammatory Agents - pharmacology Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Coriolaceae - chemistry Crystallography, X-Ray Cytotoxicity Drug Screening Assays, Antitumor Fomes officinalis Fruiting Bodies, Fungal - chemistry Hep G2 Cells Humans Inhibitory Concentration 50 Lanostane triterpene Lanosterol - analogs & derivatives Lanosterol - chemistry Lanosterol - isolation & purification Lanosterol - pharmacology Mice Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Polyporaceae Structure-Activity Relationship Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology |
title | Officimalonic acids A−H, lanostane triterpenes from the fruiting bodies of Fomes officinalis |
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