Sophaloseedlines A—G: Diverse Matrine‐Based Alkaloids from Sophora alopecuroides with Potential Anti‐Hepatitis B Virus Activities
Main observation and conclusion Sophaloseedlines A—G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, a...
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| Veröffentlicht in: | Chinese journal of chemistry 2021-09, Vol.39 (9), p.2555-2562 |
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| creator | Luo, Ding Wu, Zhong‐Nan Zhang, Ji‐Hui Lin, Qiang Chen, Neng‐Hua Chen, Si Tang, Qing Zhan, Zhao‐Chun Fan, Chun‐Lin Li, Yao‐Lan Wang, Guo‐Cai Zhang, Yu‐Bo |
| description | Main observation and conclusion
Sophaloseedlines A—G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).
Sophaloseedlines A‐G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine). |
| doi_str_mv | 10.1002/cjoc.202100279 |
| format | Article |
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Sophaloseedlines A—G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).
Sophaloseedlines A‐G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.202100279</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Alkaloids ; Anti‐HBV activity ; Biological activity ; Circular dichroism ; Crystallography ; Dichroism ; Hepatitis ; Hepatitis B ; Lamivudine ; Matrine‐based alkaloid ; Seeds ; Sophora alopecuroides ; Structure elucidation ; Viruses</subject><ispartof>Chinese journal of chemistry, 2021-09, Vol.39 (9), p.2555-2562</ispartof><rights>2021 SIOC, CAS, Shanghai and Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3179-9395f4be264e8f38dcdcccfe1b3e0af0494e48ea058849e691efb487b5c668f83</citedby><cites>FETCH-LOGICAL-c3179-9395f4be264e8f38dcdcccfe1b3e0af0494e48ea058849e691efb487b5c668f83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcjoc.202100279$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcjoc.202100279$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Luo, Ding</creatorcontrib><creatorcontrib>Wu, Zhong‐Nan</creatorcontrib><creatorcontrib>Zhang, Ji‐Hui</creatorcontrib><creatorcontrib>Lin, Qiang</creatorcontrib><creatorcontrib>Chen, Neng‐Hua</creatorcontrib><creatorcontrib>Chen, Si</creatorcontrib><creatorcontrib>Tang, Qing</creatorcontrib><creatorcontrib>Zhan, Zhao‐Chun</creatorcontrib><creatorcontrib>Fan, Chun‐Lin</creatorcontrib><creatorcontrib>Li, Yao‐Lan</creatorcontrib><creatorcontrib>Wang, Guo‐Cai</creatorcontrib><creatorcontrib>Zhang, Yu‐Bo</creatorcontrib><title>Sophaloseedlines A—G: Diverse Matrine‐Based Alkaloids from Sophora alopecuroides with Potential Anti‐Hepatitis B Virus Activities</title><title>Chinese journal of chemistry</title><description>Main observation and conclusion
Sophaloseedlines A—G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).
Sophaloseedlines A‐G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).</description><subject>Alkaloids</subject><subject>Anti‐HBV activity</subject><subject>Biological activity</subject><subject>Circular dichroism</subject><subject>Crystallography</subject><subject>Dichroism</subject><subject>Hepatitis</subject><subject>Hepatitis B</subject><subject>Lamivudine</subject><subject>Matrine‐based alkaloid</subject><subject>Seeds</subject><subject>Sophora alopecuroides</subject><subject>Structure elucidation</subject><subject>Viruses</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhSMEEqWwMltiTrETx4nZSoEWVFQkfsQWuc616pLWwU5bdevGysAT9klwVAQj07XP_c650gmCU4I7BOPoXE6N7EQ4aj4p3wtahBEappgl-_6NMQkZpq-HwZFz0wZJI9YKPh5NNRGlcQBFqefgUHe7-epfoCu9BOsA3Yvaen27-bwUDgrULd88rguHlDUz1NiNFchrFciF9RufsdL1BD2YGua1FiXq-uEDBlCJWtfaoUv0ou3C35K1XnoF3HFwoETp4ORntoPnm-un3iAcjvq3ve4wlDFJechjnig6hohRyFScFbKQUiog4xiwUJhyCjQDgZMsoxwYJ6DGNEvHiWQsU1ncDs52uZU17wtwdT41Czv3J_MoYSSmvhXuqc6OktY4Z0HlldUzYdc5wXnTb96Unf-W7Q18Z1jpEtb_0HnvbtT7834D_LqI3A</recordid><startdate>202109</startdate><enddate>202109</enddate><creator>Luo, Ding</creator><creator>Wu, Zhong‐Nan</creator><creator>Zhang, Ji‐Hui</creator><creator>Lin, Qiang</creator><creator>Chen, Neng‐Hua</creator><creator>Chen, Si</creator><creator>Tang, Qing</creator><creator>Zhan, Zhao‐Chun</creator><creator>Fan, Chun‐Lin</creator><creator>Li, Yao‐Lan</creator><creator>Wang, Guo‐Cai</creator><creator>Zhang, Yu‐Bo</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>202109</creationdate><title>Sophaloseedlines A—G: Diverse Matrine‐Based Alkaloids from Sophora alopecuroides with Potential Anti‐Hepatitis B Virus Activities</title><author>Luo, Ding ; Wu, Zhong‐Nan ; Zhang, Ji‐Hui ; Lin, Qiang ; Chen, Neng‐Hua ; Chen, Si ; Tang, Qing ; Zhan, Zhao‐Chun ; Fan, Chun‐Lin ; Li, Yao‐Lan ; Wang, Guo‐Cai ; Zhang, Yu‐Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3179-9395f4be264e8f38dcdcccfe1b3e0af0494e48ea058849e691efb487b5c668f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkaloids</topic><topic>Anti‐HBV activity</topic><topic>Biological activity</topic><topic>Circular dichroism</topic><topic>Crystallography</topic><topic>Dichroism</topic><topic>Hepatitis</topic><topic>Hepatitis B</topic><topic>Lamivudine</topic><topic>Matrine‐based alkaloid</topic><topic>Seeds</topic><topic>Sophora alopecuroides</topic><topic>Structure elucidation</topic><topic>Viruses</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Ding</creatorcontrib><creatorcontrib>Wu, Zhong‐Nan</creatorcontrib><creatorcontrib>Zhang, Ji‐Hui</creatorcontrib><creatorcontrib>Lin, Qiang</creatorcontrib><creatorcontrib>Chen, Neng‐Hua</creatorcontrib><creatorcontrib>Chen, Si</creatorcontrib><creatorcontrib>Tang, Qing</creatorcontrib><creatorcontrib>Zhan, Zhao‐Chun</creatorcontrib><creatorcontrib>Fan, Chun‐Lin</creatorcontrib><creatorcontrib>Li, Yao‐Lan</creatorcontrib><creatorcontrib>Wang, Guo‐Cai</creatorcontrib><creatorcontrib>Zhang, Yu‐Bo</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Ding</au><au>Wu, Zhong‐Nan</au><au>Zhang, Ji‐Hui</au><au>Lin, Qiang</au><au>Chen, Neng‐Hua</au><au>Chen, Si</au><au>Tang, Qing</au><au>Zhan, Zhao‐Chun</au><au>Fan, Chun‐Lin</au><au>Li, Yao‐Lan</au><au>Wang, Guo‐Cai</au><au>Zhang, Yu‐Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sophaloseedlines A—G: Diverse Matrine‐Based Alkaloids from Sophora alopecuroides with Potential Anti‐Hepatitis B Virus Activities</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2021-09</date><risdate>2021</risdate><volume>39</volume><issue>9</issue><spage>2555</spage><epage>2562</epage><pages>2555-2562</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>Main observation and conclusion
Sophaloseedlines A—G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).
Sophaloseedlines A‐G (1—7), seven new matrine‐based alkaloids along with two known analogues, were isolated from the seeds of Sophora alopecuroides. The new structures were determined based on extensive spectroscopic data, electronic circular dichroism calculations, and X‐ray crystallography. Notably, sophaloseedline A (1) represents a novel rearranged 6(5→17)‐abeo‐matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton. The hypothetical biosynthetic pathways for sophaloseedlines A—F were proposed based on co‐existing precursors. Additionally, all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus, and new alkaloids 1 and 2 displayed more potent activities than those of matrine (a parent alkaloid of title plant) and positive control (lamivudine).</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.202100279</doi><tpages>8</tpages></addata></record> |
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| subjects | Alkaloids Anti‐HBV activity Biological activity Circular dichroism Crystallography Dichroism Hepatitis Hepatitis B Lamivudine Matrine‐based alkaloid Seeds Sophora alopecuroides Structure elucidation Viruses |
| title | Sophaloseedlines A—G: Diverse Matrine‐Based Alkaloids from Sophora alopecuroides with Potential Anti‐Hepatitis B Virus Activities |
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