Cytotoxic sesquiterpenoid dimers from the resin of Commiphora myrrha Engl
Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs, were isolated from the resin of Commiphora myrrha Engl.. The structures of the undescribed compounds were elucidated based on a comprehensive analysis of spectroscopic data (NMR, UV, IR, and MS), and...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2022-12, Vol.204, p.113443, Article 113443 |
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| creator | Wang, Chao-Chao Liang, Nai-Yun Xia, Hui Wang, Rong-Ye Zhang, Yun-Feng Huo, Hui-Xia Zhao, Yun-Fang Song, Yue-Lin Zheng, Jiao Tu, Peng-Fei Li, Jun |
| description | Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs, were isolated from the resin of Commiphora myrrha Engl.. The structures of the undescribed compounds were elucidated based on a comprehensive analysis of spectroscopic data (NMR, UV, IR, and MS), and the absolute configurations were defined by comparing the experimental and calculated ECD spectra as well as by performing X-ray crystallographic analysis. All the isolated dimeric sesquiterpenoids feature a 7-oxabicyclo [2.2.1] hept-2-ene moiety formed by the [4 + 2] cycloaddition of two sesquiterpenoids. Commiphomyrones C and G and commiphoratone D showed cytotoxic activity against the HGC-27 cell line with IC50 values of 22.76, 25.01, and 27.51 μM, respectively.
Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs were isolated from the resin of Commiphora myrrha Engl. [Display omitted]
•Seven undescribed sesquiterpenoid dimers were obtained from Commiphora myrrha Engl..•All the structures with absolute configurations were completely determined.•The isolated compounds exhibited cytotoxic effects. |
| doi_str_mv | 10.1016/j.phytochem.2022.113443 |
| format | Article |
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Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs were isolated from the resin of Commiphora myrrha Engl. [Display omitted]
•Seven undescribed sesquiterpenoid dimers were obtained from Commiphora myrrha Engl..•All the structures with absolute configurations were completely determined.•The isolated compounds exhibited cytotoxic effects.</description><identifier>ISSN: 0031-9422</identifier><identifier>ISSN: 1873-3700</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2022.113443</identifier><identifier>PMID: 36169037</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Burseraceae ; Commiphomyrones A – G ; Commiphora myrrha Engl ; Cytotoxicity ; Sesquiterpenoid dimers</subject><ispartof>Phytochemistry (Oxford), 2022-12, Vol.204, p.113443, Article 113443</ispartof><rights>2022 Elsevier Ltd</rights><rights>Copyright © 2022 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c286t-60270f67ac5d1979d668eb0786f71e4dc6ddb8002913521ec27e7def98a338f73</citedby><cites>FETCH-LOGICAL-c286t-60270f67ac5d1979d668eb0786f71e4dc6ddb8002913521ec27e7def98a338f73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0031942222003594$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36169037$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Chao-Chao</creatorcontrib><creatorcontrib>Liang, Nai-Yun</creatorcontrib><creatorcontrib>Xia, Hui</creatorcontrib><creatorcontrib>Wang, Rong-Ye</creatorcontrib><creatorcontrib>Zhang, Yun-Feng</creatorcontrib><creatorcontrib>Huo, Hui-Xia</creatorcontrib><creatorcontrib>Zhao, Yun-Fang</creatorcontrib><creatorcontrib>Song, Yue-Lin</creatorcontrib><creatorcontrib>Zheng, Jiao</creatorcontrib><creatorcontrib>Tu, Peng-Fei</creatorcontrib><creatorcontrib>Li, Jun</creatorcontrib><title>Cytotoxic sesquiterpenoid dimers from the resin of Commiphora myrrha Engl</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs, were isolated from the resin of Commiphora myrrha Engl.. The structures of the undescribed compounds were elucidated based on a comprehensive analysis of spectroscopic data (NMR, UV, IR, and MS), and the absolute configurations were defined by comparing the experimental and calculated ECD spectra as well as by performing X-ray crystallographic analysis. All the isolated dimeric sesquiterpenoids feature a 7-oxabicyclo [2.2.1] hept-2-ene moiety formed by the [4 + 2] cycloaddition of two sesquiterpenoids. Commiphomyrones C and G and commiphoratone D showed cytotoxic activity against the HGC-27 cell line with IC50 values of 22.76, 25.01, and 27.51 μM, respectively.
Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs were isolated from the resin of Commiphora myrrha Engl. [Display omitted]
•Seven undescribed sesquiterpenoid dimers were obtained from Commiphora myrrha Engl..•All the structures with absolute configurations were completely determined.•The isolated compounds exhibited cytotoxic effects.</description><subject>Burseraceae</subject><subject>Commiphomyrones A – G</subject><subject>Commiphora myrrha Engl</subject><subject>Cytotoxicity</subject><subject>Sesquiterpenoid dimers</subject><issn>0031-9422</issn><issn>1873-3700</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAURS0EglL4C-CRJeXZbmxnRBVfEhILzFZqvxBXdRzsFNF_T6oWVqa3nHuv3iHkmsGMAZO3q1nfbodoWwwzDpzPGBPzuTgiE6aVKIQCOCYTAMGKas75GTnPeQUAZSnlKTkTkskKhJqQ58VYM8Rvb2nG_LnxA6Yeu-gddT5gyrRJMdChRZow-47Ghi5iCL5vY6pp2KbU1vS--1hfkJOmXme8PNwpeX-4f1s8FS-vj8-Lu5fCci2HQgJX0EhV29KxSlVOSo1LUFo2iuHcWencUgPwiomSM7RcoXLYVLoWQjdKTMnNvrdP8XODeTDBZ4vrdd1h3GTDFdOVZFWpR1TtUZtizgkb0ycf6rQ1DMzOo1mZP49m59HsPY7Jq8PIZhnQ_eV-xY3A3R7A8dUvj8lk67Gz6HxCOxgX_b8jPxgSiIU</recordid><startdate>202212</startdate><enddate>202212</enddate><creator>Wang, Chao-Chao</creator><creator>Liang, Nai-Yun</creator><creator>Xia, Hui</creator><creator>Wang, Rong-Ye</creator><creator>Zhang, Yun-Feng</creator><creator>Huo, Hui-Xia</creator><creator>Zhao, Yun-Fang</creator><creator>Song, Yue-Lin</creator><creator>Zheng, Jiao</creator><creator>Tu, Peng-Fei</creator><creator>Li, Jun</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>202212</creationdate><title>Cytotoxic sesquiterpenoid dimers from the resin of Commiphora myrrha Engl</title><author>Wang, Chao-Chao ; Liang, Nai-Yun ; Xia, Hui ; Wang, Rong-Ye ; Zhang, Yun-Feng ; Huo, Hui-Xia ; Zhao, Yun-Fang ; Song, Yue-Lin ; Zheng, Jiao ; Tu, Peng-Fei ; Li, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c286t-60270f67ac5d1979d668eb0786f71e4dc6ddb8002913521ec27e7def98a338f73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Burseraceae</topic><topic>Commiphomyrones A – G</topic><topic>Commiphora myrrha Engl</topic><topic>Cytotoxicity</topic><topic>Sesquiterpenoid dimers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Chao-Chao</creatorcontrib><creatorcontrib>Liang, Nai-Yun</creatorcontrib><creatorcontrib>Xia, Hui</creatorcontrib><creatorcontrib>Wang, Rong-Ye</creatorcontrib><creatorcontrib>Zhang, Yun-Feng</creatorcontrib><creatorcontrib>Huo, Hui-Xia</creatorcontrib><creatorcontrib>Zhao, Yun-Fang</creatorcontrib><creatorcontrib>Song, Yue-Lin</creatorcontrib><creatorcontrib>Zheng, Jiao</creatorcontrib><creatorcontrib>Tu, Peng-Fei</creatorcontrib><creatorcontrib>Li, Jun</creatorcontrib><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>Wang, Chao-Chao</au><au>Liang, Nai-Yun</au><au>Xia, Hui</au><au>Wang, Rong-Ye</au><au>Zhang, Yun-Feng</au><au>Huo, Hui-Xia</au><au>Zhao, Yun-Fang</au><au>Song, Yue-Lin</au><au>Zheng, Jiao</au><au>Tu, Peng-Fei</au><au>Li, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic sesquiterpenoid dimers from the resin of Commiphora myrrha Engl</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2022-12</date><risdate>2022</risdate><volume>204</volume><spage>113443</spage><pages>113443-</pages><artnum>113443</artnum><issn>0031-9422</issn><issn>1873-3700</issn><eissn>1873-3700</eissn><abstract>Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs, were isolated from the resin of Commiphora myrrha Engl.. The structures of the undescribed compounds were elucidated based on a comprehensive analysis of spectroscopic data (NMR, UV, IR, and MS), and the absolute configurations were defined by comparing the experimental and calculated ECD spectra as well as by performing X-ray crystallographic analysis. All the isolated dimeric sesquiterpenoids feature a 7-oxabicyclo [2.2.1] hept-2-ene moiety formed by the [4 + 2] cycloaddition of two sesquiterpenoids. Commiphomyrones C and G and commiphoratone D showed cytotoxic activity against the HGC-27 cell line with IC50 values of 22.76, 25.01, and 27.51 μM, respectively.
Seven undescribed sesquiterpenoid dimers, commiphomyrones A – G, together with three known analogs were isolated from the resin of Commiphora myrrha Engl. [Display omitted]
•Seven undescribed sesquiterpenoid dimers were obtained from Commiphora myrrha Engl..•All the structures with absolute configurations were completely determined.•The isolated compounds exhibited cytotoxic effects.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>36169037</pmid><doi>10.1016/j.phytochem.2022.113443</doi></addata></record> |
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| subjects | Burseraceae Commiphomyrones A – G Commiphora myrrha Engl Cytotoxicity Sesquiterpenoid dimers |
| title | Cytotoxic sesquiterpenoid dimers from the resin of Commiphora myrrha Engl |
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