21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa
Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21bet...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2008-02, Vol.69 (4), p.1057-1064 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Cáceres-Castillo, David Mena-Rejón, Gonzalo J Cedillo-Rivera, Roberto Quijano, Leovigildo |
| description | Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant. |
| format | Article |
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They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant.</description><identifier>ISSN: 0031-9422</identifier><identifier>PMID: 18061220</identifier><language>eng</language><publisher>England</publisher><subject>Hippocrateaceae - chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oleanolic Acid - analogs & derivatives ; Oleanolic Acid - chemistry ; Oleanolic Acid - isolation & purification ; Pentacyclic Triterpenes - chemistry ; Pentacyclic Triterpenes - isolation & purification ; Plant Bark - chemistry ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Ursolic Acid</subject><ispartof>Phytochemistry (Oxford), 2008-02, Vol.69 (4), p.1057-1064</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18061220$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cáceres-Castillo, David</creatorcontrib><creatorcontrib>Mena-Rejón, Gonzalo J</creatorcontrib><creatorcontrib>Cedillo-Rivera, Roberto</creatorcontrib><creatorcontrib>Quijano, Leovigildo</creatorcontrib><title>21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant.</description><subject>Hippocrateaceae - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Oleanolic Acid - analogs & derivatives</subject><subject>Oleanolic Acid - chemistry</subject><subject>Oleanolic Acid - isolation & purification</subject><subject>Pentacyclic Triterpenes - chemistry</subject><subject>Pentacyclic Triterpenes - isolation & purification</subject><subject>Plant Bark - chemistry</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Ursolic Acid</subject><issn>0031-9422</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1j0tLxDAURrNQnHH0L0hX7gI3j6bpchjUCgNuZl_yuIVKHzFJYfrvLTiuvs3h45w7sgcQjNaS8x15TOkbAMpSqQeyYxoU4xz25MiZxWxos_o4X1c6D2gmMyHNa8Aixz5jDDhhKro4j0XThzC7aDKaAq8Oh2SeyH1nhoTPtz2Qy_vb5dTQ89fH5-l4pqGUQL33Risn685pIWQNFe_AgefaWwDJtROVYnUHwhrnLCq-eSsUrEJVSqvFgbz-3YY4_yyYcjv2aRMYNtl5SW0FQrFKlxv4cgMXO6JvQ-xHE9f2v1n8AqbeUXQ</recordid><startdate>200802</startdate><enddate>200802</enddate><creator>Cáceres-Castillo, David</creator><creator>Mena-Rejón, Gonzalo J</creator><creator>Cedillo-Rivera, Roberto</creator><creator>Quijano, Leovigildo</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>200802</creationdate><title>21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa</title><author>Cáceres-Castillo, David ; Mena-Rejón, Gonzalo J ; Cedillo-Rivera, Roberto ; Quijano, Leovigildo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p540-ddda86c49fc83349072f0c0d28db00428c37619f03baccbe629426e317e654b83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Hippocrateaceae - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Oleanolic Acid - analogs & derivatives</topic><topic>Oleanolic Acid - chemistry</topic><topic>Oleanolic Acid - isolation & purification</topic><topic>Pentacyclic Triterpenes - chemistry</topic><topic>Pentacyclic Triterpenes - isolation & purification</topic><topic>Plant Bark - chemistry</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Ursolic Acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cáceres-Castillo, David</creatorcontrib><creatorcontrib>Mena-Rejón, Gonzalo J</creatorcontrib><creatorcontrib>Cedillo-Rivera, Roberto</creatorcontrib><creatorcontrib>Quijano, Leovigildo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cáceres-Castillo, David</au><au>Mena-Rejón, Gonzalo J</au><au>Cedillo-Rivera, Roberto</au><au>Quijano, Leovigildo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2008-02</date><risdate>2008</risdate><volume>69</volume><issue>4</issue><spage>1057</spage><epage>1064</epage><pages>1057-1064</pages><issn>0031-9422</issn><abstract>Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant.</abstract><cop>England</cop><pmid>18061220</pmid><tpages>8</tpages></addata></record> |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Hippocrateaceae - chemistry Magnetic Resonance Spectroscopy Molecular Structure Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemistry Oleanolic Acid - isolation & purification Pentacyclic Triterpenes - chemistry Pentacyclic Triterpenes - isolation & purification Plant Bark - chemistry Triterpenes - chemistry Triterpenes - isolation & purification Ursolic Acid |
| title | 21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa |
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