(+)-/(−)-Angelignanine, a pair of neolignan enantiomers with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head
A pair of 2,7′-cyclo-8,9′-neolignan enantiomers with an unprecedented carbon skeleton and hypnotic effect were isolated and structurally characterized from an aqueous extract of the Angelica sinensis root heads (guitou). Biogenetically, the carbon skeleton is postulated from coupling between ferulic...
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| Veröffentlicht in: | Chinese chemical letters 2021-05, Vol.32 (5), p.1657-1659 |
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| creator | Chen, Youzhe Guo, Qinglan Xu, Chengbo Zhu, Chenggen Zhang, Jianjun Shi, Jiangong |
| description | A pair of 2,7′-cyclo-8,9′-neolignan enantiomers with an unprecedented carbon skeleton and hypnotic effect were isolated and structurally characterized from an aqueous extract of the Angelica sinensis root heads (guitou). Biogenetically, the carbon skeleton is postulated from coupling between ferulic acid and coniferyl alcohol.
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A pair of neolignan enantiomers with an unprecedented carbon skeleton, (+)-/(−)-angelignanine [(+)-/(−)-1], was isolated as minor components of an aqueous extract of the Angelica sinensis root heads (guitou). Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism (CD) exciton chirality method as well as electronic CD quantum calculations. The enantiomers represent the first 2,7′-cyclo-8,9′-neolignans, of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed. In an in vivo test, both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg (i.g.). |
| doi_str_mv | 10.1016/j.cclet.2020.11.067 |
| format | Article |
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[Display omitted]
A pair of neolignan enantiomers with an unprecedented carbon skeleton, (+)-/(−)-angelignanine [(+)-/(−)-1], was isolated as minor components of an aqueous extract of the Angelica sinensis root heads (guitou). Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism (CD) exciton chirality method as well as electronic CD quantum calculations. The enantiomers represent the first 2,7′-cyclo-8,9′-neolignans, of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed. In an in vivo test, both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg (i.g.).</description><identifier>ISSN: 1001-8417</identifier><identifier>EISSN: 1878-5964</identifier><identifier>DOI: 10.1016/j.cclet.2020.11.067</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>(+)-/(−)-Angelignanine ; 2,7′-Cyclo-8,9′-neolignan ; Angelica sinensis ; Neolignan ; Umbelliferae</subject><ispartof>Chinese chemical letters, 2021-05, Vol.32 (5), p.1657-1659</ispartof><rights>2021</rights><rights>Copyright © Wanfang Data Co. Ltd. All Rights Reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c335t-48af096ab4479c5300b3378f1b377ed7c13818d1d76bd6156058fdaf1a3375cd3</citedby><cites>FETCH-LOGICAL-c335t-48af096ab4479c5300b3378f1b377ed7c13818d1d76bd6156058fdaf1a3375cd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.wanfangdata.com.cn/images/PeriodicalImages/zghxkb/zghxkb.jpg</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.cclet.2020.11.067$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Chen, Youzhe</creatorcontrib><creatorcontrib>Guo, Qinglan</creatorcontrib><creatorcontrib>Xu, Chengbo</creatorcontrib><creatorcontrib>Zhu, Chenggen</creatorcontrib><creatorcontrib>Zhang, Jianjun</creatorcontrib><creatorcontrib>Shi, Jiangong</creatorcontrib><title>(+)-/(−)-Angelignanine, a pair of neolignan enantiomers with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head</title><title>Chinese chemical letters</title><description>A pair of 2,7′-cyclo-8,9′-neolignan enantiomers with an unprecedented carbon skeleton and hypnotic effect were isolated and structurally characterized from an aqueous extract of the Angelica sinensis root heads (guitou). Biogenetically, the carbon skeleton is postulated from coupling between ferulic acid and coniferyl alcohol.
[Display omitted]
A pair of neolignan enantiomers with an unprecedented carbon skeleton, (+)-/(−)-angelignanine [(+)-/(−)-1], was isolated as minor components of an aqueous extract of the Angelica sinensis root heads (guitou). Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism (CD) exciton chirality method as well as electronic CD quantum calculations. The enantiomers represent the first 2,7′-cyclo-8,9′-neolignans, of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed. In an in vivo test, both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg (i.g.).</description><subject>(+)-/(−)-Angelignanine</subject><subject>2,7′-Cyclo-8,9′-neolignan</subject><subject>Angelica sinensis</subject><subject>Neolignan</subject><subject>Umbelliferae</subject><issn>1001-8417</issn><issn>1878-5964</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9UcFOGzEUXFUgFWi_oBffCqIb_OLdtXPggBAUJCQu9Gx57efEIbFT24HAF3Dm2M_jS3C6nLnYT6OZN_ZMVf0AOgIK3cl8pPUC82hMxwWBEe34l2oPBBd1O-manTJTCrVogH-t9lOaUzoWgnV71b_D46P65PDt5fWoPvNTXLipV955_EUUWSkXSbDEYxhwguXILiwxJvLo8owUbO1XETUa9BkN0Sr2wZN0j-VBZbAxLLcs9XeNYZ0IbnJUOm_X5hmSwVMrkoqnTy6RGEImM1TmW7Vr1SLh94_7oPpzeXF3flXf3P6-Pj-7qTVjba4boSyddKpvGj7RLaO0Z4wLCz3jHA3XwAQIA4Z3vemg7WgrrFEWVKG12rCD6uew91F5q_xUzsM6-uIon6ezzX1fQgXaUqCFyQamjiGliFauoluq-CSBym0Rci7_FyG3RUgAWYooqtNBheUTDw6jTNqhL4m5kluWJrhP9e8_AZSN</recordid><startdate>20210501</startdate><enddate>20210501</enddate><creator>Chen, Youzhe</creator><creator>Guo, Qinglan</creator><creator>Xu, Chengbo</creator><creator>Zhu, Chenggen</creator><creator>Zhang, Jianjun</creator><creator>Shi, Jiangong</creator><general>Elsevier B.V</general><general>State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medico,Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China</general><scope>AAYXX</scope><scope>CITATION</scope><scope>2B.</scope><scope>4A8</scope><scope>92I</scope><scope>93N</scope><scope>PSX</scope><scope>TCJ</scope></search><sort><creationdate>20210501</creationdate><title>(+)-/(−)-Angelignanine, a pair of neolignan enantiomers with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head</title><author>Chen, Youzhe ; Guo, Qinglan ; Xu, Chengbo ; Zhu, Chenggen ; Zhang, Jianjun ; Shi, Jiangong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c335t-48af096ab4479c5300b3378f1b377ed7c13818d1d76bd6156058fdaf1a3375cd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>(+)-/(−)-Angelignanine</topic><topic>2,7′-Cyclo-8,9′-neolignan</topic><topic>Angelica sinensis</topic><topic>Neolignan</topic><topic>Umbelliferae</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Youzhe</creatorcontrib><creatorcontrib>Guo, Qinglan</creatorcontrib><creatorcontrib>Xu, Chengbo</creatorcontrib><creatorcontrib>Zhu, Chenggen</creatorcontrib><creatorcontrib>Zhang, Jianjun</creatorcontrib><creatorcontrib>Shi, Jiangong</creatorcontrib><collection>CrossRef</collection><collection>Wanfang Data Journals - Hong Kong</collection><collection>WANFANG Data Centre</collection><collection>Wanfang Data Journals</collection><collection>万方数据期刊 - 香港版</collection><collection>China Online Journals (COJ)</collection><collection>China Online Journals (COJ)</collection><jtitle>Chinese chemical letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Youzhe</au><au>Guo, Qinglan</au><au>Xu, Chengbo</au><au>Zhu, Chenggen</au><au>Zhang, Jianjun</au><au>Shi, Jiangong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(+)-/(−)-Angelignanine, a pair of neolignan enantiomers with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head</atitle><jtitle>Chinese chemical letters</jtitle><date>2021-05-01</date><risdate>2021</risdate><volume>32</volume><issue>5</issue><spage>1657</spage><epage>1659</epage><pages>1657-1659</pages><issn>1001-8417</issn><eissn>1878-5964</eissn><abstract>A pair of 2,7′-cyclo-8,9′-neolignan enantiomers with an unprecedented carbon skeleton and hypnotic effect were isolated and structurally characterized from an aqueous extract of the Angelica sinensis root heads (guitou). Biogenetically, the carbon skeleton is postulated from coupling between ferulic acid and coniferyl alcohol.
[Display omitted]
A pair of neolignan enantiomers with an unprecedented carbon skeleton, (+)-/(−)-angelignanine [(+)-/(−)-1], was isolated as minor components of an aqueous extract of the Angelica sinensis root heads (guitou). Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism (CD) exciton chirality method as well as electronic CD quantum calculations. The enantiomers represent the first 2,7′-cyclo-8,9′-neolignans, of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed. In an in vivo test, both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg (i.g.).</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.cclet.2020.11.067</doi><tpages>3</tpages></addata></record> |
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| identifier | ISSN: 1001-8417 |
| ispartof | Chinese chemical letters, 2021-05, Vol.32 (5), p.1657-1659 |
| issn | 1001-8417 1878-5964 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete; Alma/SFX Local Collection |
| subjects | (+)-/(−)-Angelignanine 2,7′-Cyclo-8,9′-neolignan Angelica sinensis Neolignan Umbelliferae |
| title | (+)-/(−)-Angelignanine, a pair of neolignan enantiomers with an unprecedented carbon skeleton from an aqueous extract of the Angelica sinensis root head |
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