Azaphilones with protein tyrosine phosphatase inhibitory activity isolated from the fungus Aspergillus deflectus
Six undescribed azaphilones, deflectins C1-C3, deflectins D1-D2, and deflectin E, along with five known azaphilones were obtained from a solid culture of the wild fungus Aspergillus deflectus NCC0415. Their structures were determined by HRESIMS, NMR and ECD analyses, together with the GIAO 13C NMR c...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2020-02, Vol.170, p.112224-112224, Article 112224 |
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| creator | Huo, Changhong Lu, Xinhua Zheng, Zhihui Li, Yeying Xu, Yan Zheng, Haizhou Niu, Yuanchen |
| description | Six undescribed azaphilones, deflectins C1-C3, deflectins D1-D2, and deflectin E, along with five known azaphilones were obtained from a solid culture of the wild fungus Aspergillus deflectus NCC0415. Their structures were determined by HRESIMS, NMR and ECD analyses, together with the GIAO 13C NMR calculation method. All compounds displayed strong or moderate inhibitory activity against protein tyrosine phosphatases SHP2 and PTP1B. Structure-activity relationship analysis of these azaphilones suggested that the length of the ketone aliphatic side chain would affect their SHP2 and PTP1B inhibitory activity. In addition, the presence of a Δ8(12) double bond on γ-lactone ring and the presence of CH3-2’ in fatty chains may increase their inhibitory activity.
Eleven deflectin-type azaphilones isolated from the fungus Aspergillus deflectus NCC0415 displayed potent inhibitory activity against SHP2 and PTP1B. [Display omitted]
•Six undescribed azaphilones were isolated from a fungus Aspergillus deflectus.•GIAO 13C NMR calculation established the absolute configuration of azaphilones.•Azaphilones were inhibitors of protein tyrosine phosphatases SHP2 and PTP1B.•Bioactivities and SAR analysis of these azaphilones were presented. |
| doi_str_mv | 10.1016/j.phytochem.2019.112224 |
| format | Article |
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Eleven deflectin-type azaphilones isolated from the fungus Aspergillus deflectus NCC0415 displayed potent inhibitory activity against SHP2 and PTP1B. [Display omitted]
•Six undescribed azaphilones were isolated from a fungus Aspergillus deflectus.•GIAO 13C NMR calculation established the absolute configuration of azaphilones.•Azaphilones were inhibitors of protein tyrosine phosphatases SHP2 and PTP1B.•Bioactivities and SAR analysis of these azaphilones were presented.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2019.112224</identifier><identifier>PMID: 31812919</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject><![CDATA[Aspergillus - chemistry ; Aspergillus deflectus Fennell & Raper ; Azaphilones ; Benzopyrans - chemistry ; Benzopyrans - isolation & purification ; Benzopyrans - pharmacology ; Deflectin-type ; Dose-Response Relationship, Drug ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - isolation & purification ; Enzyme Inhibitors - pharmacology ; Humans ; Molecular Structure ; Moniliaceae ; Phytochemicals - chemistry ; Phytochemicals - isolation & purification ; Phytochemicals - pharmacology ; Pigments, Biological - chemistry ; Pigments, Biological - isolation & purification ; Pigments, Biological - pharmacology ; Protein tyrosine phosphatase inhibitor ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism ; Structure-Activity Relationship]]></subject><ispartof>Phytochemistry (Oxford), 2020-02, Vol.170, p.112224-112224, Article 112224</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c371t-66264d6f1a11e746903bcb55f1c08c518a473d675fa0cba67dea6cb2824ec61d3</citedby><cites>FETCH-LOGICAL-c371t-66264d6f1a11e746903bcb55f1c08c518a473d675fa0cba67dea6cb2824ec61d3</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.2019.112224$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31812919$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huo, Changhong</creatorcontrib><creatorcontrib>Lu, Xinhua</creatorcontrib><creatorcontrib>Zheng, Zhihui</creatorcontrib><creatorcontrib>Li, Yeying</creatorcontrib><creatorcontrib>Xu, Yan</creatorcontrib><creatorcontrib>Zheng, Haizhou</creatorcontrib><creatorcontrib>Niu, Yuanchen</creatorcontrib><title>Azaphilones with protein tyrosine phosphatase inhibitory activity isolated from the fungus Aspergillus deflectus</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Six undescribed azaphilones, deflectins C1-C3, deflectins D1-D2, and deflectin E, along with five known azaphilones were obtained from a solid culture of the wild fungus Aspergillus deflectus NCC0415. Their structures were determined by HRESIMS, NMR and ECD analyses, together with the GIAO 13C NMR calculation method. All compounds displayed strong or moderate inhibitory activity against protein tyrosine phosphatases SHP2 and PTP1B. Structure-activity relationship analysis of these azaphilones suggested that the length of the ketone aliphatic side chain would affect their SHP2 and PTP1B inhibitory activity. In addition, the presence of a Δ8(12) double bond on γ-lactone ring and the presence of CH3-2’ in fatty chains may increase their inhibitory activity.
Eleven deflectin-type azaphilones isolated from the fungus Aspergillus deflectus NCC0415 displayed potent inhibitory activity against SHP2 and PTP1B. [Display omitted]
•Six undescribed azaphilones were isolated from a fungus Aspergillus deflectus.•GIAO 13C NMR calculation established the absolute configuration of azaphilones.•Azaphilones were inhibitors of protein tyrosine phosphatases SHP2 and PTP1B.•Bioactivities and SAR analysis of these azaphilones were presented.</description><subject>Aspergillus - chemistry</subject><subject>Aspergillus deflectus Fennell & Raper</subject><subject>Azaphilones</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - isolation & purification</subject><subject>Benzopyrans - pharmacology</subject><subject>Deflectin-type</subject><subject>Dose-Response Relationship, Drug</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Moniliaceae</subject><subject>Phytochemicals - chemistry</subject><subject>Phytochemicals - isolation & purification</subject><subject>Phytochemicals - pharmacology</subject><subject>Pigments, Biological - chemistry</subject><subject>Pigments, Biological - isolation & purification</subject><subject>Pigments, Biological - pharmacology</subject><subject>Protein tyrosine phosphatase inhibitor</subject><subject>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors</subject><subject>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism</subject><subject>Structure-Activity Relationship</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFu1DAQhi0EokvhFcBHLlk8duIkx1VFAakSFzhbjj1pZpXEwXaKwtOTakuvnGYO3z-j_2PsA4gjCNCfzsdl2HJwA05HKaA9AkgpyxfsAE2tClUL8ZIdhFBQtKWUV-xNSmchRFVp_ZpdKWhAttAe2HL6Y5eBxjBj4r8pD3yJISPNPG8xJJqRL0NIy2CzTchpHqijHOLGrcv0QHnjlMJoM3rexzDxPCDv1_l-TfyUFoz3NI777rEf0eU1vWWvejsmfPc0r9nP288_br4Wd9-_fLs53RVO1ZALraUuve7BAmBd6laoznVV1YMTjaugsWWtvK6r3grXWV17tNp1spElOg1eXbOPl7t7n18rpmwmSg7H0c4Y1mSkkrIRqqnaHa0vqNsbp4i9WSJNNm4GhHnUbc7mWbd51G0uuvfk-6cnazehf87987sDpwuAe9UHwmiSI5wdeoq7DuMD_ffJX6YgmNQ</recordid><startdate>202002</startdate><enddate>202002</enddate><creator>Huo, Changhong</creator><creator>Lu, Xinhua</creator><creator>Zheng, Zhihui</creator><creator>Li, Yeying</creator><creator>Xu, Yan</creator><creator>Zheng, Haizhou</creator><creator>Niu, Yuanchen</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>202002</creationdate><title>Azaphilones with protein tyrosine phosphatase inhibitory activity isolated from the fungus Aspergillus deflectus</title><author>Huo, Changhong ; Lu, Xinhua ; Zheng, Zhihui ; Li, Yeying ; Xu, Yan ; Zheng, Haizhou ; Niu, Yuanchen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c371t-66264d6f1a11e746903bcb55f1c08c518a473d675fa0cba67dea6cb2824ec61d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aspergillus - chemistry</topic><topic>Aspergillus deflectus Fennell & Raper</topic><topic>Azaphilones</topic><topic>Benzopyrans - chemistry</topic><topic>Benzopyrans - isolation & purification</topic><topic>Benzopyrans - pharmacology</topic><topic>Deflectin-type</topic><topic>Dose-Response Relationship, Drug</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Moniliaceae</topic><topic>Phytochemicals - chemistry</topic><topic>Phytochemicals - isolation & purification</topic><topic>Phytochemicals - pharmacology</topic><topic>Pigments, Biological - chemistry</topic><topic>Pigments, Biological - isolation & purification</topic><topic>Pigments, Biological - pharmacology</topic><topic>Protein tyrosine phosphatase inhibitor</topic><topic>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors</topic><topic>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huo, Changhong</creatorcontrib><creatorcontrib>Lu, Xinhua</creatorcontrib><creatorcontrib>Zheng, Zhihui</creatorcontrib><creatorcontrib>Li, Yeying</creatorcontrib><creatorcontrib>Xu, Yan</creatorcontrib><creatorcontrib>Zheng, Haizhou</creatorcontrib><creatorcontrib>Niu, Yuanchen</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>Huo, Changhong</au><au>Lu, Xinhua</au><au>Zheng, Zhihui</au><au>Li, Yeying</au><au>Xu, Yan</au><au>Zheng, Haizhou</au><au>Niu, Yuanchen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Azaphilones with protein tyrosine phosphatase inhibitory activity isolated from the fungus Aspergillus deflectus</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2020-02</date><risdate>2020</risdate><volume>170</volume><spage>112224</spage><epage>112224</epage><pages>112224-112224</pages><artnum>112224</artnum><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Six undescribed azaphilones, deflectins C1-C3, deflectins D1-D2, and deflectin E, along with five known azaphilones were obtained from a solid culture of the wild fungus Aspergillus deflectus NCC0415. Their structures were determined by HRESIMS, NMR and ECD analyses, together with the GIAO 13C NMR calculation method. All compounds displayed strong or moderate inhibitory activity against protein tyrosine phosphatases SHP2 and PTP1B. Structure-activity relationship analysis of these azaphilones suggested that the length of the ketone aliphatic side chain would affect their SHP2 and PTP1B inhibitory activity. In addition, the presence of a Δ8(12) double bond on γ-lactone ring and the presence of CH3-2’ in fatty chains may increase their inhibitory activity.
Eleven deflectin-type azaphilones isolated from the fungus Aspergillus deflectus NCC0415 displayed potent inhibitory activity against SHP2 and PTP1B. [Display omitted]
•Six undescribed azaphilones were isolated from a fungus Aspergillus deflectus.•GIAO 13C NMR calculation established the absolute configuration of azaphilones.•Azaphilones were inhibitors of protein tyrosine phosphatases SHP2 and PTP1B.•Bioactivities and SAR analysis of these azaphilones were presented.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>31812919</pmid><doi>10.1016/j.phytochem.2019.112224</doi><tpages>1</tpages></addata></record> |
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| subjects | Aspergillus - chemistry Aspergillus deflectus Fennell & Raper Azaphilones Benzopyrans - chemistry Benzopyrans - isolation & purification Benzopyrans - pharmacology Deflectin-type Dose-Response Relationship, Drug Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Humans Molecular Structure Moniliaceae Phytochemicals - chemistry Phytochemicals - isolation & purification Phytochemicals - pharmacology Pigments, Biological - chemistry Pigments, Biological - isolation & purification Pigments, Biological - pharmacology Protein tyrosine phosphatase inhibitor Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism Structure-Activity Relationship |
| title | Azaphilones with protein tyrosine phosphatase inhibitory activity isolated from the fungus Aspergillus deflectus |
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