Microbial Transformation of Rubijervine
Preparative-scale fermentation of rubijervine (1), the known 22,26-epiminocholestane Veratrum alkaloid, with Cunninghamella echinulata ATCC 9244 has resulted in the isolation of the new metabolites 7α-hydroxyrubijervine (2) and solanid-5-ene-3β,12α-diol-1-one (3). Structure elucidation of these meta...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2002, Vol.50(11), pp.1427-1429 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Sayed, Khalid A. El Dunbar, D. Chuck |
| description | Preparative-scale fermentation of rubijervine (1), the known 22,26-epiminocholestane Veratrum alkaloid, with Cunninghamella echinulata ATCC 9244 has resulted in the isolation of the new metabolites 7α-hydroxyrubijervine (2) and solanid-5-ene-3β,12α-diol-1-one (3). Structure elucidation of these metabolites was based primarily on 1D- and 2D-NMR analyses. The microbe C. echinulata ATCC 9244 was able to metabolize rings A and B of rubijervine but failed to metabolize rings C, D or its N-containing side chain, a finding which is analogous to the results of previous fermentation studies of steroidal alkaloids. |
| doi_str_mv | 10.1248/cpb.50.1427 |
| format | Article |
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El ; Dunbar, D. Chuck</creator><creatorcontrib>Sayed, Khalid A. El ; Dunbar, D. Chuck</creatorcontrib><description>Preparative-scale fermentation of rubijervine (1), the known 22,26-epiminocholestane Veratrum alkaloid, with Cunninghamella echinulata ATCC 9244 has resulted in the isolation of the new metabolites 7α-hydroxyrubijervine (2) and solanid-5-ene-3β,12α-diol-1-one (3). Structure elucidation of these metabolites was based primarily on 1D- and 2D-NMR analyses. The microbe C. echinulata ATCC 9244 was able to metabolize rings A and B of rubijervine but failed to metabolize rings C, D or its N-containing side chain, a finding which is analogous to the results of previous fermentation studies of steroidal alkaloids.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.50.1427</identifier><identifier>PMID: 12419903</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>7α-hydroxyrubijervine ; Antihypertensive Agents - chemistry ; Antihypertensive Agents - pharmacokinetics ; biocatalysis ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Biotransformation - physiology ; Cunninghamella - metabolism ; Cunninghamella echinulata ; Fermentation ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Medical sciences ; Methods. Procedures. Technologies ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. 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El</creatorcontrib><creatorcontrib>Dunbar, D. Chuck</creatorcontrib><title>Microbial Transformation of Rubijervine</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Preparative-scale fermentation of rubijervine (1), the known 22,26-epiminocholestane Veratrum alkaloid, with Cunninghamella echinulata ATCC 9244 has resulted in the isolation of the new metabolites 7α-hydroxyrubijervine (2) and solanid-5-ene-3β,12α-diol-1-one (3). Structure elucidation of these metabolites was based primarily on 1D- and 2D-NMR analyses. The microbe C. echinulata ATCC 9244 was able to metabolize rings A and B of rubijervine but failed to metabolize rings C, D or its N-containing side chain, a finding which is analogous to the results of previous fermentation studies of steroidal alkaloids.</description><subject>7α-hydroxyrubijervine</subject><subject>Antihypertensive Agents - chemistry</subject><subject>Antihypertensive Agents - pharmacokinetics</subject><subject>biocatalysis</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Biotransformation - physiology</subject><subject>Cunninghamella - metabolism</subject><subject>Cunninghamella echinulata</subject><subject>Fermentation</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Methods. Procedures. Technologies</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>rubijervine</subject><subject>solanid-5-ene-3β,12α-diol-1-one</subject><subject>Veratrum alkaloid</subject><subject>Veratrum Alkaloids - chemistry</subject><subject>Veratrum Alkaloids - pharmacokinetics</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkF1LwzAUhoMoOqdX3stA1AvpzHfbSx1-wUSQeR1O00QzunYmreC_N2VlA2-Sw8mT8yYPQmcETwnl2a1eF1MRa07TPTQijKeJoJTtoxHGOE8ok-wIHYewxJgKnLJDdBTvkTzHbISuX532TeGgmiw81ME2fgWta-pJYyfvXeGWxv-42pygAwtVMKfDPkYfjw-L2XMyf3t6md3NEy0ZaRPIJCUsY4ZJW5bGcsm5xCzNDWQmYzonnGgQkBELtqC4TGPXCCgFBQKyYGN0tZm79s13Z0KrVi5oU1VQm6YLKqVS4kzkEbz4By6bztfxbYr0kTzNeE_dbKj4yRC8sWrt3Qr8ryJY9fZUtKdErKO9SJ8PM7tiZcodO-iKwOUAQNBQ2WhMu7DjOBOc5n3s_YZbhhY-zRYA3zpdmW0oGdY-fXf4BV6Zmv0BEjCNJQ</recordid><startdate>20021101</startdate><enddate>20021101</enddate><creator>Sayed, Khalid A. El</creator><creator>Dunbar, D. Chuck</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20021101</creationdate><title>Microbial Transformation of Rubijervine</title><author>Sayed, Khalid A. El ; Dunbar, D. Chuck</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c631t-a8621383e36fddef464460379ea8e83c9141ca5a81fafb20d7e83e5ad52a1a6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>7α-hydroxyrubijervine</topic><topic>Antihypertensive Agents - chemistry</topic><topic>Antihypertensive Agents - pharmacokinetics</topic><topic>biocatalysis</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Biotransformation - physiology</topic><topic>Cunninghamella - metabolism</topic><topic>Cunninghamella echinulata</topic><topic>Fermentation</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Methods. Procedures. Technologies</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>rubijervine</topic><topic>solanid-5-ene-3β,12α-diol-1-one</topic><topic>Veratrum alkaloid</topic><topic>Veratrum Alkaloids - chemistry</topic><topic>Veratrum Alkaloids - pharmacokinetics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sayed, Khalid A. El</creatorcontrib><creatorcontrib>Dunbar, D. Chuck</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sayed, Khalid A. El</au><au>Dunbar, D. Chuck</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microbial Transformation of Rubijervine</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2002-11-01</date><risdate>2002</risdate><volume>50</volume><issue>11</issue><spage>1427</spage><epage>1429</epage><pages>1427-1429</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Preparative-scale fermentation of rubijervine (1), the known 22,26-epiminocholestane Veratrum alkaloid, with Cunninghamella echinulata ATCC 9244 has resulted in the isolation of the new metabolites 7α-hydroxyrubijervine (2) and solanid-5-ene-3β,12α-diol-1-one (3). Structure elucidation of these metabolites was based primarily on 1D- and 2D-NMR analyses. The microbe C. echinulata ATCC 9244 was able to metabolize rings A and B of rubijervine but failed to metabolize rings C, D or its N-containing side chain, a finding which is analogous to the results of previous fermentation studies of steroidal alkaloids.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>12419903</pmid><doi>10.1248/cpb.50.1427</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 7α-hydroxyrubijervine Antihypertensive Agents - chemistry Antihypertensive Agents - pharmacokinetics biocatalysis Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotransformation - physiology Cunninghamella - metabolism Cunninghamella echinulata Fermentation Fundamental and applied biological sciences. Psychology General pharmacology Medical sciences Methods. Procedures. Technologies Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments rubijervine solanid-5-ene-3β,12α-diol-1-one Veratrum alkaloid Veratrum Alkaloids - chemistry Veratrum Alkaloids - pharmacokinetics |
| title | Microbial Transformation of Rubijervine |
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