Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda
Three new oleanane-type triterpene saponins (1-3), named grandibracteosides A-C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR exp...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2005-06, Vol.68 (6), p.897-903 |
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| creator | Krief, S Thoison, O Sevenet, T Wrangham, R.W Lavaud, C |
| description | Three new oleanane-type triterpene saponins (1-3), named grandibracteosides A-C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance. |
| doi_str_mv | 10.1021/np049576i |
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The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np049576i</identifier><identifier>PMID: 15974615</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject><![CDATA[Albizia ; Albizia grandibracteata ; Albizzia - chemistry ; Animals ; anthranilic acid ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; chemical structure ; Drug Screening Assays, Antitumor ; Ecology, environment ; Feeding Behavior ; General pharmacology ; grandibracteosides ; Humans ; KB Cells ; Life Sciences ; Medical sciences ; Molecular Structure ; oleanane ; Oleanolic Acid - analogs & derivatives ; Oleanolic Acid - chemistry ; Oleanolic Acid - isolation & purification ; Oleanolic Acid - pharmacology ; ortho-Aminobenzoates - chemistry ; ortho-Aminobenzoates - isolation & purification ; ortho-Aminobenzoates - pharmacology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; plant extracts ; Plant Leaves - chemistry ; Plants, Medicinal - chemistry ; Plasmodium falciparum - drug effects ; Primates - physiology ; Saponins - chemistry ; Saponins - isolation & purification ; Saponins - pharmacology ; spectral analysis ; stereochemistry ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Triterpenes - pharmacology ; triterpenoid saponins ; Tumor Cells, Cultured ; Uganda]]></subject><ispartof>Journal of natural products (Washington, D.C.), 2005-06, Vol.68 (6), p.897-903</ispartof><rights>2005 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-3814-7641</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16934015$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15974615$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00256552$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Krief, S</creatorcontrib><creatorcontrib>Thoison, O</creatorcontrib><creatorcontrib>Sevenet, T</creatorcontrib><creatorcontrib>Wrangham, R.W</creatorcontrib><creatorcontrib>Lavaud, C</creatorcontrib><title>Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Three new oleanane-type triterpene saponins (1-3), named grandibracteosides A-C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance.</description><subject>Albizia</subject><subject>Albizia grandibracteata</subject><subject>Albizzia - chemistry</subject><subject>Animals</subject><subject>anthranilic acid</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Ecology, environment</subject><subject>Feeding Behavior</subject><subject>General pharmacology</subject><subject>grandibracteosides</subject><subject>Humans</subject><subject>KB Cells</subject><subject>Life Sciences</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>oleanane</subject><subject>Oleanolic Acid - analogs & derivatives</subject><subject>Oleanolic Acid - chemistry</subject><subject>Oleanolic Acid - isolation & purification</subject><subject>Oleanolic Acid - pharmacology</subject><subject>ortho-Aminobenzoates - chemistry</subject><subject>ortho-Aminobenzoates - isolation & purification</subject><subject>ortho-Aminobenzoates - pharmacology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>Plant Leaves - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Primates - physiology</subject><subject>Saponins - chemistry</subject><subject>Saponins - isolation & purification</subject><subject>Saponins - pharmacology</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><subject>triterpenoid saponins</subject><subject>Tumor Cells, Cultured</subject><subject>Uganda</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90E1vEzEQBmALgWgoHPgDsBdAHBY866_4GCqgSJFAbSK4WeNdb2rY7G7tTUX59QxJKDcutjTzePxqGHsK_A3wCt72I5dWGR3vsRmoipeaV-o-m3HQohRzLU_Yo5y_c84Ft-ohOwFljdSgZiysUpxCGkM_xKbIOA597Avsp6uEfexwCrlo07AtFp2PvyIWG6o30Sesp4ATFl3AGzKx34Q8habwt8WY4nb_kCatN8TxMXvQYpfDk-N9ytYf3q_Ozsvl54-fzhbLspVCTCVynGNde7BzCgheSVNj2wAieN82spFaCa5URR3dmGAqq02w3gPCXNhKnLLXh7lX2Ll9jHTrBozufLF0f2qcFqNpwA2QfXWwYxqudxTebWOuQ9dhH4ZddsaA4aCUIPnyv1IbqzUXluCzI9z5bWjuEvxdN4EXR4C5xq6lXdYx_3PaCsn3rjy4SDv9edfH9IM-E0a51ZdLt1Tf4Ou7C-kuyD8_-BYHh5tEM9eXFQfBgQ4LXPwGGGSmLA</recordid><startdate>20050601</startdate><enddate>20050601</enddate><creator>Krief, S</creator><creator>Thoison, O</creator><creator>Sevenet, T</creator><creator>Wrangham, R.W</creator><creator>Lavaud, C</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>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-3814-7641</orcidid></search><sort><creationdate>20050601</creationdate><title>Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda</title><author>Krief, S ; Thoison, O ; Sevenet, T ; Wrangham, R.W ; Lavaud, C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f433t-a0a8accb1985971b547cafd1aa1bbfd4d46530552b546d7e72967e9bb1a183923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Albizia</topic><topic>Albizia grandibracteata</topic><topic>Albizzia - chemistry</topic><topic>Animals</topic><topic>anthranilic acid</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Ecology, environment</topic><topic>Feeding Behavior</topic><topic>General pharmacology</topic><topic>grandibracteosides</topic><topic>Humans</topic><topic>KB Cells</topic><topic>Life Sciences</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>oleanane</topic><topic>Oleanolic Acid - analogs & derivatives</topic><topic>Oleanolic Acid - chemistry</topic><topic>Oleanolic Acid - isolation & purification</topic><topic>Oleanolic Acid - pharmacology</topic><topic>ortho-Aminobenzoates - chemistry</topic><topic>ortho-Aminobenzoates - isolation & purification</topic><topic>ortho-Aminobenzoates - pharmacology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>Plant Leaves - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Primates - physiology</topic><topic>Saponins - chemistry</topic><topic>Saponins - isolation & purification</topic><topic>Saponins - pharmacology</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><topic>triterpenoid saponins</topic><topic>Tumor Cells, Cultured</topic><topic>Uganda</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krief, S</creatorcontrib><creatorcontrib>Thoison, O</creatorcontrib><creatorcontrib>Sevenet, T</creatorcontrib><creatorcontrib>Wrangham, R.W</creatorcontrib><creatorcontrib>Lavaud, C</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>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krief, S</au><au>Thoison, O</au><au>Sevenet, T</au><au>Wrangham, R.W</au><au>Lavaud, C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2005-06-01</date><risdate>2005</risdate><volume>68</volume><issue>6</issue><spage>897</spage><epage>903</epage><pages>897-903</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Three new oleanane-type triterpene saponins (1-3), named grandibracteosides A-C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>15974615</pmid><doi>10.1021/np049576i</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-3814-7641</orcidid></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2005-06, Vol.68 (6), p.897-903 |
| issn | 0163-3864 1520-6025 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Albizia Albizia grandibracteata Albizzia - chemistry Animals anthranilic acid Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences chemical structure Drug Screening Assays, Antitumor Ecology, environment Feeding Behavior General pharmacology grandibracteosides Humans KB Cells Life Sciences Medical sciences Molecular Structure oleanane Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemistry Oleanolic Acid - isolation & purification Oleanolic Acid - pharmacology ortho-Aminobenzoates - chemistry ortho-Aminobenzoates - isolation & purification ortho-Aminobenzoates - pharmacology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals plant extracts Plant Leaves - chemistry Plants, Medicinal - chemistry Plasmodium falciparum - drug effects Primates - physiology Saponins - chemistry Saponins - isolation & purification Saponins - pharmacology spectral analysis stereochemistry Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology triterpenoid saponins Tumor Cells, Cultured Uganda |
| title | Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda |
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