Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid
Tetrahydroberberine (systematic name: 9,10‐dimethoxy‐5,8,13,13a‐tetrahydro‐6H‐benzo[g][1,3]benzodioxolo[5,6‐a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is obser...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2015-04, Vol.71 (4), p.262-265 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
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| creator | Pingali, Subramanya Donahue, James P. Payton‐Stewart, Florastina |
| description | Tetrahydroberberine (systematic name: 9,10‐dimethoxy‐5,8,13,13a‐tetrahydro‐6H‐benzo[g][1,3]benzodioxolo[5,6‐a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. The intermolecular hydrogen bonds that play an apparent role in crystal packing are 1,3‐benzodioxole –CH2...OCH3 and –OCH3...OCH3 interactions between neighboring molecules. |
| doi_str_mv | 10.1107/S2053229615004076 |
| format | Article |
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A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. 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Section C, Crystal structure communications</title><addtitle>Acta Crystallogr C Struct Chem</addtitle><description>Tetrahydroberberine (systematic name: 9,10‐dimethoxy‐5,8,13,13a‐tetrahydro‐6H‐benzo[g][1,3]benzodioxolo[5,6‐a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. The intermolecular hydrogen bonds that play an apparent role in crystal packing are 1,3‐benzodioxole –CH2...OCH3 and –OCH3...OCH3 interactions between neighboring molecules.</description><subject>Alkalinity</subject><subject>alkaloid</subject><subject>Alkaloids</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - pharmacology</subject><subject>Aromatic compounds</subject><subject>Berberine Alkaloids - chemistry</subject><subject>Berberine Alkaloids - pharmacology</subject><subject>berberine derivative</subject><subject>biological activity</subject><subject>canadine</subject><subject>crystal structure</subject><subject>Crystallization</subject><subject>Crystallography</subject><subject>Crystallography, X-Ray</subject><subject>Crystals</subject><subject>C—H...O hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Inversions</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Molecules</subject><subject>Names</subject><subject>Pharmacology</subject><subject>quinolizidine core</subject><subject>tetrahydroberberine</subject><issn>2053-2296</issn><issn>0108-2701</issn><issn>2053-2296</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9LAzEQxYMottR-AC-y4MWD1ZmkSXaPpfgPCx6sh56WbDZpt6ZNzXaV_fZubRXRQ2FghsdvHsw8Qk4RrhBBXj9T4IzSRCAH6IMUB6S9kXob7fDX3CLdspwDACLlUuIxaVEeM0Fj2iajsVkHNavz4DMTmiqW5jJS0WqmwkJp7_y00Mq5OlJ6XbybaKnWVfgSvNZVaPhppNyrcr7IT8iRVa403V3vkJfbm_Hwvjd6unsYDkY93ZeM9bjNQebMZgJlZqyyQlnNBFIBkMUZGgOg-pprahK0Cc9Qc2qllhjnlvYt65CLre8q-LfKlOt0UZTaOKeWxldlipIzjihkvB8VIomZRGANev4HnfsqLJtDNlRME4mMNxRuKR18WQZj01UoFirUKUK6CSb9F0yzc7ZzrrKFyX82vmNogGQLfBTO1Psd08FkSB8nDJp3fgIJuJgN</recordid><startdate>201504</startdate><enddate>201504</enddate><creator>Pingali, Subramanya</creator><creator>Donahue, James P.</creator><creator>Payton‐Stewart, Florastina</creator><general>International Union of Crystallography</general><general>Wiley Subscription Services, Inc</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201504</creationdate><title>Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid</title><author>Pingali, Subramanya ; Donahue, James P. ; Payton‐Stewart, Florastina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4733-5fd07d3fb617befaf6afc3612600b8b1ee00a4c5c2e91f95b1c52f7c718df24f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkalinity</topic><topic>alkaloid</topic><topic>Alkaloids</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - pharmacology</topic><topic>Aromatic compounds</topic><topic>Berberine Alkaloids - chemistry</topic><topic>Berberine Alkaloids - pharmacology</topic><topic>berberine derivative</topic><topic>biological activity</topic><topic>canadine</topic><topic>crystal structure</topic><topic>Crystallization</topic><topic>Crystallography</topic><topic>Crystallography, X-Ray</topic><topic>Crystals</topic><topic>C—H...O hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Inversions</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Molecules</topic><topic>Names</topic><topic>Pharmacology</topic><topic>quinolizidine core</topic><topic>tetrahydroberberine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pingali, Subramanya</creatorcontrib><creatorcontrib>Donahue, James P.</creatorcontrib><creatorcontrib>Payton‐Stewart, Florastina</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Acta crystallographica. 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Section C, Crystal structure communications</jtitle><addtitle>Acta Crystallogr C Struct Chem</addtitle><date>2015-04</date><risdate>2015</risdate><volume>71</volume><issue>4</issue><spage>262</spage><epage>265</epage><pages>262-265</pages><issn>2053-2296</issn><issn>0108-2701</issn><eissn>2053-2296</eissn><eissn>1600-5759</eissn><abstract>Tetrahydroberberine (systematic name: 9,10‐dimethoxy‐5,8,13,13a‐tetrahydro‐6H‐benzo[g][1,3]benzodioxolo[5,6‐a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. 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| ispartof | Acta crystallographica. Section C, Crystal structure communications, 2015-04, Vol.71 (4), p.262-265 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete; Alma/SFX Local Collection |
| subjects | Alkalinity alkaloid Alkaloids Alkaloids - chemistry Alkaloids - pharmacology Aromatic compounds Berberine Alkaloids - chemistry Berberine Alkaloids - pharmacology berberine derivative biological activity canadine crystal structure Crystallization Crystallography Crystallography, X-Ray Crystals C—H...O hydrogen bonding Hydrogen bonds Inversions Molecular Conformation Molecular Structure Molecules Names Pharmacology quinolizidine core tetrahydroberberine |
| title | Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid |
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