New Sesquiterpene α-Methylene Lactones from the Egyptian Plant Jasonia candicans
Extracts of the plant Jasonia candicans possess antimicrobial activity. ET2O/MeOH extracts were subjected to liquid chromatography, and several sesquiterpenes were isolated and identified including the known compounds confertin [1], 4,11(13)-eudesmadien-12-oic acid [2], and 11-eudesmen-4-ol [3]. Two...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1993-08, Vol.56 (8), p.1276-1280 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Ahmed, Ahmed A Mahmoud, Ahmed A Williams, Howard J Scott, A. Ian Reibenspies, Joseph H Mabry, Tom J |
| description | Extracts of the plant Jasonia candicans possess antimicrobial activity. ET2O/MeOH extracts were subjected to liquid chromatography, and several sesquiterpenes were isolated and identified including the known compounds confertin [1], 4,11(13)-eudesmadien-12-oic acid [2], and 11-eudesmen-4-ol [3]. Two new diol alpha-methylene lactone antimicrobial agents were identified from nmr and mass spectral data and X-ray crystallography as (4 alpha, 5 alpha, 8 beta, 10 beta)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide [4] and (4 alpha, 5 alpha, 8 beta, 10 alpha)-4,10-dihydroxyl-1,11 (13)-guaidien-12,8-olide[5], which differ in stereochemistry at the C-10 tertiary alcohol center. |
| doi_str_mv | 10.1021/np50098a011 |
| format | Article |
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Ian ; Reibenspies, Joseph H ; Mabry, Tom J</creator><creatorcontrib>Ahmed, Ahmed A ; Mahmoud, Ahmed A ; Williams, Howard J ; Scott, A. Ian ; Reibenspies, Joseph H ; Mabry, Tom J</creatorcontrib><description>Extracts of the plant Jasonia candicans possess antimicrobial activity. ET2O/MeOH extracts were subjected to liquid chromatography, and several sesquiterpenes were isolated and identified including the known compounds confertin [1], 4,11(13)-eudesmadien-12-oic acid [2], and 11-eudesmen-4-ol [3]. Two new diol alpha-methylene lactone antimicrobial agents were identified from nmr and mass spectral data and X-ray crystallography as (4 alpha, 5 alpha, 8 beta, 10 beta)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide [4] and (4 alpha, 5 alpha, 8 beta, 10 alpha)-4,10-dihydroxyl-1,11 (13)-guaidien-12,8-olide[5], which differ in stereochemistry at the C-10 tertiary alcohol center.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np50098a011</identifier><identifier>PMID: 8229012</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>ANTIMICROBIAL PROPERTIES ; Biological and medical sciences ; COMPOSITAE ; EGIPTO ; EGYPT ; EGYPTE ; EXTRACTOS VEGETALES ; EXTRAIT D'ORIGINE VEGETALE ; General pharmacology ; LACTONAS ; LACTONE ; LACTONES ; Lactones - chemistry ; Lactones - isolation & purification ; Medical sciences ; MOLECULAR STRUCTURE ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; PLANT EXTRACTS ; Plant Extracts - analysis ; Plants, Medicinal - chemistry ; PROPIEDADES ANTIMICROBIANAS ; PROPRIETE ANTIMICROBIENNE ; PURIFICACION ; PURIFICATION ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; SESQUITERPENOIDE ; SESQUITERPENOIDS ; SESQUITERPENOS ; STRUCTURE</subject><ispartof>Journal of natural products (Washington, D.C.), 1993-08, Vol.56 (8), p.1276-1280</ispartof><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a402t-869e425d44cbcd16dd4c40f55c0d36738cdbef8e84fcf2d4c17b02361c8eb1743</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np50098a011$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np50098a011$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27065,27913,27914,56727,56777</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4897998$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8229012$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ahmed, Ahmed A</creatorcontrib><creatorcontrib>Mahmoud, Ahmed A</creatorcontrib><creatorcontrib>Williams, Howard J</creatorcontrib><creatorcontrib>Scott, A. Ian</creatorcontrib><creatorcontrib>Reibenspies, Joseph H</creatorcontrib><creatorcontrib>Mabry, Tom J</creatorcontrib><title>New Sesquiterpene α-Methylene Lactones from the Egyptian Plant Jasonia candicans</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Extracts of the plant Jasonia candicans possess antimicrobial activity. ET2O/MeOH extracts were subjected to liquid chromatography, and several sesquiterpenes were isolated and identified including the known compounds confertin [1], 4,11(13)-eudesmadien-12-oic acid [2], and 11-eudesmen-4-ol [3]. Two new diol alpha-methylene lactone antimicrobial agents were identified from nmr and mass spectral data and X-ray crystallography as (4 alpha, 5 alpha, 8 beta, 10 beta)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide [4] and (4 alpha, 5 alpha, 8 beta, 10 alpha)-4,10-dihydroxyl-1,11 (13)-guaidien-12,8-olide[5], which differ in stereochemistry at the C-10 tertiary alcohol center.</description><subject>ANTIMICROBIAL PROPERTIES</subject><subject>Biological and medical sciences</subject><subject>COMPOSITAE</subject><subject>EGIPTO</subject><subject>EGYPT</subject><subject>EGYPTE</subject><subject>EXTRACTOS VEGETALES</subject><subject>EXTRAIT D'ORIGINE VEGETALE</subject><subject>General pharmacology</subject><subject>LACTONAS</subject><subject>LACTONE</subject><subject>LACTONES</subject><subject>Lactones - chemistry</subject><subject>Lactones - isolation & purification</subject><subject>Medical sciences</subject><subject>MOLECULAR STRUCTURE</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>PLANT EXTRACTS</subject><subject>Plant Extracts - analysis</subject><subject>Plants, Medicinal - chemistry</subject><subject>PROPIEDADES ANTIMICROBIANAS</subject><subject>PROPRIETE ANTIMICROBIENNE</subject><subject>PURIFICACION</subject><subject>PURIFICATION</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>SESQUITERPENOIDE</subject><subject>SESQUITERPENOIDS</subject><subject>SESQUITERPENOS</subject><subject>STRUCTURE</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFu1DAQhi0EKtvCiRsSUg4IDigwdpzEPqKlpaAFFrY9W44zblOyTmo7KvtYvAjPhKusVhy4jDX6Pv0a_4Q8o_CWAqPv3FgCSKGB0gdkQUsGeQWsfEgWQKsiL0TFH5PjEG4AoABZHpEjwZgEyhbk-1e8yzYYbqcuoh_RYfbnd_4F4_Wuv19W2sTBYcisH7ZZvMbs9Go3xk67bN1rF7PPOgyu05nRru3SCE_II6v7gE_37wm5PDu9WJ7nq28fPy3fr3LNgcVcVBI5K1vOTWNaWrUtNxxsWRpoi6ouhGkbtAIFt8ayBGndACsqagQ2tObFCXk1545-uJ0wRLXtgsE-XYXDFFRdQQmS10l8M4vGDyF4tGr03Vb7naKg7gtU_xSY7Bf72KnZYntw940l_nLPdTC6t14704WDxoWspRRJy2etCxF_HbD2P1X6XF2qi_VG_Vien61XrFAfkv989q0elL7yKfJyIzmjvJYJvp6hNkHdDJN3qdj_Xv8XqAScdw</recordid><startdate>19930801</startdate><enddate>19930801</enddate><creator>Ahmed, Ahmed A</creator><creator>Mahmoud, Ahmed A</creator><creator>Williams, Howard J</creator><creator>Scott, A. Ian</creator><creator>Reibenspies, Joseph H</creator><creator>Mabry, Tom J</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><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>7X8</scope></search><sort><creationdate>19930801</creationdate><title>New Sesquiterpene α-Methylene Lactones from the Egyptian Plant Jasonia candicans</title><author>Ahmed, Ahmed A ; Mahmoud, Ahmed A ; Williams, Howard J ; Scott, A. Ian ; Reibenspies, Joseph H ; Mabry, Tom J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a402t-869e425d44cbcd16dd4c40f55c0d36738cdbef8e84fcf2d4c17b02361c8eb1743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>ANTIMICROBIAL PROPERTIES</topic><topic>Biological and medical sciences</topic><topic>COMPOSITAE</topic><topic>EGIPTO</topic><topic>EGYPT</topic><topic>EGYPTE</topic><topic>EXTRACTOS VEGETALES</topic><topic>EXTRAIT D'ORIGINE VEGETALE</topic><topic>General pharmacology</topic><topic>LACTONAS</topic><topic>LACTONE</topic><topic>LACTONES</topic><topic>Lactones - chemistry</topic><topic>Lactones - isolation & purification</topic><topic>Medical sciences</topic><topic>MOLECULAR STRUCTURE</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>PLANT EXTRACTS</topic><topic>Plant Extracts - analysis</topic><topic>Plants, Medicinal - chemistry</topic><topic>PROPIEDADES ANTIMICROBIANAS</topic><topic>PROPRIETE ANTIMICROBIENNE</topic><topic>PURIFICACION</topic><topic>PURIFICATION</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>SESQUITERPENOIDE</topic><topic>SESQUITERPENOIDS</topic><topic>SESQUITERPENOS</topic><topic>STRUCTURE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ahmed, Ahmed A</creatorcontrib><creatorcontrib>Mahmoud, Ahmed A</creatorcontrib><creatorcontrib>Williams, Howard J</creatorcontrib><creatorcontrib>Scott, A. Ian</creatorcontrib><creatorcontrib>Reibenspies, Joseph H</creatorcontrib><creatorcontrib>Mabry, Tom J</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><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>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ahmed, Ahmed A</au><au>Mahmoud, Ahmed A</au><au>Williams, Howard J</au><au>Scott, A. Ian</au><au>Reibenspies, Joseph H</au><au>Mabry, Tom J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Sesquiterpene α-Methylene Lactones from the Egyptian Plant Jasonia candicans</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1993-08-01</date><risdate>1993</risdate><volume>56</volume><issue>8</issue><spage>1276</spage><epage>1280</epage><pages>1276-1280</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Extracts of the plant Jasonia candicans possess antimicrobial activity. ET2O/MeOH extracts were subjected to liquid chromatography, and several sesquiterpenes were isolated and identified including the known compounds confertin [1], 4,11(13)-eudesmadien-12-oic acid [2], and 11-eudesmen-4-ol [3]. Two new diol alpha-methylene lactone antimicrobial agents were identified from nmr and mass spectral data and X-ray crystallography as (4 alpha, 5 alpha, 8 beta, 10 beta)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide [4] and (4 alpha, 5 alpha, 8 beta, 10 alpha)-4,10-dihydroxyl-1,11 (13)-guaidien-12,8-olide[5], which differ in stereochemistry at the C-10 tertiary alcohol center.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>8229012</pmid><doi>10.1021/np50098a011</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 1993-08, Vol.56 (8), p.1276-1280 |
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| subjects | ANTIMICROBIAL PROPERTIES Biological and medical sciences COMPOSITAE EGIPTO EGYPT EGYPTE EXTRACTOS VEGETALES EXTRAIT D'ORIGINE VEGETALE General pharmacology LACTONAS LACTONE LACTONES Lactones - chemistry Lactones - isolation & purification Medical sciences MOLECULAR STRUCTURE Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments PLANT EXTRACTS Plant Extracts - analysis Plants, Medicinal - chemistry PROPIEDADES ANTIMICROBIANAS PROPRIETE ANTIMICROBIENNE PURIFICACION PURIFICATION Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification SESQUITERPENOIDE SESQUITERPENOIDS SESQUITERPENOS STRUCTURE |
| title | New Sesquiterpene α-Methylene Lactones from the Egyptian Plant Jasonia candicans |
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