Anti-inflammatory labdane diterpenoids from Leonurus japonicus Houtt
Seven undescribed labdane diterpenoids, japonicones A-G, were isolated from the aerial parts of Leonurus japonicus Houtt. Japonicones C-G contained two keto carbonyl groups in their structures attached to C-3 and C-7, which are rare for labdane diterpenoids. The structures and absolute configuration...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2020-05, Vol.173, p.112223-112223, Article 112223 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Yang, Biao Hu, Yumei Cheng, Ningbo Su, Zhenzhen Zhong, Yan Cao, Zeyu Cao, Liang Huang, Wenzhe Wang, Zhenzhong Xiao, Wei |
| description | Seven undescribed labdane diterpenoids, japonicones A-G, were isolated from the aerial parts of Leonurus japonicus Houtt. Japonicones C-G contained two keto carbonyl groups in their structures attached to C-3 and C-7, which are rare for labdane diterpenoids. The structures and absolute configurations of japonicones A-G were established by means of spectroscopic analyses (HRESIMS, 1D and 2D NMR, and ECD). Their anti-inflammatory activities were evaluated by measuring their inhibitory effects on PGE2 production in LPS-stimulated RAW264.7 macrophages. Japonicones A-D and G showed inhibition of PGE2 production with IC50 values in the range of 8.62–30.71 μM (the positive control paracetamol showed an IC50 = 5.79 μM).
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•Seven undescribed labdane diterpenoids were isolated from the aerial parts of Leonurus japonicus Houtt.•Their structures and absolute configurations were established by means of spectroscopic analyses.•Compounds 1−4, and 7 showed inhibition of PGE2 production with IC50 values in the range of 8.62−30.71 μM. |
| doi_str_mv | 10.1016/j.phytochem.2019.112223 |
| format | Article |
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•Seven undescribed labdane diterpenoids were isolated from the aerial parts of Leonurus japonicus Houtt.•Their structures and absolute configurations were established by means of spectroscopic analyses.•Compounds 1−4, and 7 showed inhibition of PGE2 production with IC50 values in the range of 8.62−30.71 μM.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2019.112223</identifier><identifier>PMID: 32113063</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-inflammatory ; Anti-Inflammatory Agents ; Diterpenes ; Labdane diterpenoids ; Lamiaceae ; Leonurus ; Leonurus japonicus houtt ; Magnetic Resonance Spectroscopy ; Molecular Structure</subject><ispartof>Phytochemistry (Oxford), 2020-05, Vol.173, p.112223-112223, Article 112223</ispartof><rights>2020 Elsevier Ltd</rights><rights>Copyright © 2020 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c371t-c51225adb24cd806ce3c1e9382d4edf806055a2167f858c38ee74677da2f4a313</citedby><cites>FETCH-LOGICAL-c371t-c51225adb24cd806ce3c1e9382d4edf806055a2167f858c38ee74677da2f4a313</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.2019.112223$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32113063$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Biao</creatorcontrib><creatorcontrib>Hu, Yumei</creatorcontrib><creatorcontrib>Cheng, Ningbo</creatorcontrib><creatorcontrib>Su, Zhenzhen</creatorcontrib><creatorcontrib>Zhong, Yan</creatorcontrib><creatorcontrib>Cao, Zeyu</creatorcontrib><creatorcontrib>Cao, Liang</creatorcontrib><creatorcontrib>Huang, Wenzhe</creatorcontrib><creatorcontrib>Wang, Zhenzhong</creatorcontrib><creatorcontrib>Xiao, Wei</creatorcontrib><title>Anti-inflammatory labdane diterpenoids from Leonurus japonicus Houtt</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Seven undescribed labdane diterpenoids, japonicones A-G, were isolated from the aerial parts of Leonurus japonicus Houtt. Japonicones C-G contained two keto carbonyl groups in their structures attached to C-3 and C-7, which are rare for labdane diterpenoids. The structures and absolute configurations of japonicones A-G were established by means of spectroscopic analyses (HRESIMS, 1D and 2D NMR, and ECD). Their anti-inflammatory activities were evaluated by measuring their inhibitory effects on PGE2 production in LPS-stimulated RAW264.7 macrophages. Japonicones A-D and G showed inhibition of PGE2 production with IC50 values in the range of 8.62–30.71 μM (the positive control paracetamol showed an IC50 = 5.79 μM).
[Display omitted]
•Seven undescribed labdane diterpenoids were isolated from the aerial parts of Leonurus japonicus Houtt.•Their structures and absolute configurations were established by means of spectroscopic analyses.•Compounds 1−4, and 7 showed inhibition of PGE2 production with IC50 values in the range of 8.62−30.71 μM.</description><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents</subject><subject>Diterpenes</subject><subject>Labdane diterpenoids</subject><subject>Lamiaceae</subject><subject>Leonurus</subject><subject>Leonurus japonicus houtt</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</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>eNqFkMtOwzAQRS0EoqXwC5AlmwQ_EiddVuVRpEpsYG259kR1lMTBdpD697hK6ZbVjEb3ztw5CD0QnBFM-FOTDftDsGoPXUYxWWaEUErZBZqTqmQpKzG-RHOMGUmXOaUzdON9gzEuCs6v0YxRQhjmbI6eV30wqenrVnadDNYdklbutOwh0SaAG6C3RvukdrZLtmD70Y0-aeRge6Nit7FjCLfoqpath7tTXaCv15fP9Sbdfry9r1fbVLGShFQVMWQh9Y7mSleYK2CKwJJVVOeg6ziJ-SQlvKyrolKsAihzXpZa0jqXjLAFepz2Ds5-j-CD6IxX0LYxrh29oIwv80ijyqO0nKTKWe8d1GJwppPuIAgWR4SiEWeE4ohQTAij8_50ZNx1oM--P2ZRsJoEEF_9MeCEVwZ6Bdo4UEFoa_498gs_z4bU</recordid><startdate>202005</startdate><enddate>202005</enddate><creator>Yang, Biao</creator><creator>Hu, Yumei</creator><creator>Cheng, Ningbo</creator><creator>Su, Zhenzhen</creator><creator>Zhong, Yan</creator><creator>Cao, Zeyu</creator><creator>Cao, Liang</creator><creator>Huang, Wenzhe</creator><creator>Wang, Zhenzhong</creator><creator>Xiao, Wei</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>202005</creationdate><title>Anti-inflammatory labdane diterpenoids from Leonurus japonicus Houtt</title><author>Yang, Biao ; Hu, Yumei ; Cheng, Ningbo ; Su, Zhenzhen ; Zhong, Yan ; Cao, Zeyu ; Cao, Liang ; Huang, Wenzhe ; Wang, Zhenzhong ; Xiao, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c371t-c51225adb24cd806ce3c1e9382d4edf806055a2167f858c38ee74677da2f4a313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents</topic><topic>Diterpenes</topic><topic>Labdane diterpenoids</topic><topic>Lamiaceae</topic><topic>Leonurus</topic><topic>Leonurus japonicus houtt</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Biao</creatorcontrib><creatorcontrib>Hu, Yumei</creatorcontrib><creatorcontrib>Cheng, Ningbo</creatorcontrib><creatorcontrib>Su, Zhenzhen</creatorcontrib><creatorcontrib>Zhong, Yan</creatorcontrib><creatorcontrib>Cao, Zeyu</creatorcontrib><creatorcontrib>Cao, Liang</creatorcontrib><creatorcontrib>Huang, Wenzhe</creatorcontrib><creatorcontrib>Wang, Zhenzhong</creatorcontrib><creatorcontrib>Xiao, Wei</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>Yang, Biao</au><au>Hu, Yumei</au><au>Cheng, Ningbo</au><au>Su, Zhenzhen</au><au>Zhong, Yan</au><au>Cao, Zeyu</au><au>Cao, Liang</au><au>Huang, Wenzhe</au><au>Wang, Zhenzhong</au><au>Xiao, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-inflammatory labdane diterpenoids from Leonurus japonicus Houtt</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2020-05</date><risdate>2020</risdate><volume>173</volume><spage>112223</spage><epage>112223</epage><pages>112223-112223</pages><artnum>112223</artnum><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Seven undescribed labdane diterpenoids, japonicones A-G, were isolated from the aerial parts of Leonurus japonicus Houtt. Japonicones C-G contained two keto carbonyl groups in their structures attached to C-3 and C-7, which are rare for labdane diterpenoids. The structures and absolute configurations of japonicones A-G were established by means of spectroscopic analyses (HRESIMS, 1D and 2D NMR, and ECD). Their anti-inflammatory activities were evaluated by measuring their inhibitory effects on PGE2 production in LPS-stimulated RAW264.7 macrophages. Japonicones A-D and G showed inhibition of PGE2 production with IC50 values in the range of 8.62–30.71 μM (the positive control paracetamol showed an IC50 = 5.79 μM).
[Display omitted]
•Seven undescribed labdane diterpenoids were isolated from the aerial parts of Leonurus japonicus Houtt.•Their structures and absolute configurations were established by means of spectroscopic analyses.•Compounds 1−4, and 7 showed inhibition of PGE2 production with IC50 values in the range of 8.62−30.71 μM.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>32113063</pmid><doi>10.1016/j.phytochem.2019.112223</doi><tpages>1</tpages></addata></record> |
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| subjects | Anti-inflammatory Anti-Inflammatory Agents Diterpenes Labdane diterpenoids Lamiaceae Leonurus Leonurus japonicus houtt Magnetic Resonance Spectroscopy Molecular Structure |
| title | Anti-inflammatory labdane diterpenoids from Leonurus japonicus Houtt |
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