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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Veröffentlicht in:Phytochemistry (Oxford) 2016-10, Vol.130, p.193-200
Hauptverfasser: Han, Jianxin, Li, Liya, Zhong, Jialiang, Tohtaton, Zeynep, Ren, Qing, Han, Li, Huang, Xueshi, Yuan, Tao
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container_start_page 193
container_title Phytochemistry (Oxford)
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creator Han, Jianxin
Li, Liya
Zhong, Jialiang
Tohtaton, Zeynep
Ren, Qing
Han, Li
Huang, Xueshi
Yuan, Tao
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
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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><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 &amp; purification ; Anti-Inflammatory Agents - pharmacology ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation &amp; 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 &amp; derivatives ; Lanosterol - chemistry ; Lanosterol - isolation &amp; purification ; Lanosterol - pharmacology ; Mice ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Polyporaceae ; Structure-Activity Relationship ; Triterpenes - chemistry ; Triterpenes - isolation &amp; 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. 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[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 &amp; purification</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation &amp; 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 &amp; derivatives</subject><subject>Lanosterol - chemistry</subject><subject>Lanosterol - isolation &amp; 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 &amp; 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 &amp; purification</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation &amp; 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 &amp; 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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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