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Isolation and structures of avicins D and G: in vitro tumor-inhibitory saponins derived from Acacia victoriae

Two new saponins named avicins D (1) and G (2) were isolated from the seed pods of the desert legume plant Acacia victoriae. The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked...

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Published in:	Journal of natural products (Washington, D.C.) D.C.), 2003-06, Vol.66 (6), p.779-783
Main Authors:	Jayatilake, G.S, Freeberg, D.R, Liu, Z, Richheimer, S.L, Blake, M.E, Bailey, D.T, Haridas, V, Gutterman, J.U
Format:	Article
Language:	English
Subjects:	Acacia Acacia - chemistry Acacia victoriae acacie acid acid hydrolysis apoptosis Arizona avicins basic hydrolysis biochemical pathways Biological and medical sciences carboxylic acids cell lines chemical structure cytotoxicity Drug Screening Assays, Antitumor Fabaceae General pharmacology glycosides Humans Jurkat Cells legumes Medical sciences Molecular Structure monosaccharides monoterpenoids Nuclear Magnetic Resonance, Biomolecular oligosaccharides Oligosaccharides - chemistry Oligosaccharides - isolation & purification Oligosaccharides - pharmacology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals plant extracts Plants, Medicinal - chemistry prosaponins quinovose saponins Saponins - chemistry Saponins - isolation & purification Saponins - pharmacology seeds spectral analysis sugars Terpenes - chemistry Terpenes - isolation & purification Terpenes - pharmacology triterpenoid saponins Tumor Cells, Cultured - drug effects
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container_start_page	779
container_title	Journal of natural products (Washington, D.C.)
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creator	Jayatilake, G.S Freeberg, D.R Liu, Z Richheimer, S.L Blake, M.E Bailey, D.T Haridas, V Gutterman, J.U
description	Two new saponins named avicins D (1) and G (2) were isolated from the seed pods of the desert legume plant Acacia victoriae. The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked to C-21 comprised of two monoterpene carboxylic acids and a quinovose moiety. Both compounds exhibited potent cytotoxicity (apoptosis) against human T-cell leukemia (Jurkat cells) in vitro.
doi_str_mv	10.1021/np020400v
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The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked to C-21 comprised of two monoterpene carboxylic acids and a quinovose moiety. Both compounds exhibited potent cytotoxicity (apoptosis) against human T-cell leukemia (Jurkat cells) in vitro.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np020400v</identifier><identifier>PMID: 12828461</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acacia ; Acacia - chemistry ; Acacia victoriae ; acacie acid ; acid hydrolysis ; apoptosis ; Arizona ; avicins ; basic hydrolysis ; biochemical pathways ; Biological and medical sciences ; carboxylic acids ; cell lines ; chemical structure ; cytotoxicity ; Drug Screening Assays, Antitumor ; Fabaceae ; General pharmacology ; glycosides ; Humans ; Jurkat Cells ; legumes ; Medical sciences ; Molecular Structure ; monosaccharides ; monoterpenoids ; Nuclear Magnetic Resonance, Biomolecular ; oligosaccharides ; Oligosaccharides - chemistry ; Oligosaccharides - isolation & purification ; Oligosaccharides - pharmacology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; plant extracts ; Plants, Medicinal - chemistry ; prosaponins ; quinovose ; saponins ; Saponins - chemistry ; Saponins - isolation & purification ; Saponins - pharmacology ; seeds ; spectral analysis ; sugars ; Terpenes - chemistry ; Terpenes - isolation & purification ; Terpenes - pharmacology ; triterpenoid saponins ; Tumor Cells, Cultured - drug effects</subject><ispartof>Journal of natural products (Washington, D.C.), 2003-06, Vol.66 (6), p.779-783</ispartof><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14924823$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12828461$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jayatilake, G.S</creatorcontrib><creatorcontrib>Freeberg, D.R</creatorcontrib><creatorcontrib>Liu, Z</creatorcontrib><creatorcontrib>Richheimer, S.L</creatorcontrib><creatorcontrib>Blake, M.E</creatorcontrib><creatorcontrib>Bailey, D.T</creatorcontrib><creatorcontrib>Haridas, V</creatorcontrib><creatorcontrib>Gutterman, J.U</creatorcontrib><title>Isolation and structures of avicins D and G: in vitro tumor-inhibitory saponins derived from Acacia victoriae</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Two new saponins named avicins D (1) and G (2) were isolated from the seed pods of the desert legume plant Acacia victoriae. The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked to C-21 comprised of two monoterpene carboxylic acids and a quinovose moiety. Both compounds exhibited potent cytotoxicity (apoptosis) against human T-cell leukemia (Jurkat cells) in vitro.</description><subject>Acacia</subject><subject>Acacia - chemistry</subject><subject>Acacia victoriae</subject><subject>acacie acid</subject><subject>acid hydrolysis</subject><subject>apoptosis</subject><subject>Arizona</subject><subject>avicins</subject><subject>basic hydrolysis</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>carboxylic acids</subject><subject>cell lines</subject><subject>chemical structure</subject><subject>cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fabaceae</subject><subject>General pharmacology</subject><subject>glycosides</subject><subject>Humans</subject><subject>Jurkat Cells</subject><subject>legumes</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>monosaccharides</subject><subject>monoterpenoids</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>oligosaccharides</subject><subject>Oligosaccharides - chemistry</subject><subject>Oligosaccharides - isolation & purification</subject><subject>Oligosaccharides - pharmacology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>Plants, Medicinal - chemistry</subject><subject>prosaponins</subject><subject>quinovose</subject><subject>saponins</subject><subject>Saponins - chemistry</subject><subject>Saponins - isolation & purification</subject><subject>Saponins - pharmacology</subject><subject>seeds</subject><subject>spectral analysis</subject><subject>sugars</subject><subject>Terpenes - chemistry</subject><subject>Terpenes - isolation & purification</subject><subject>Terpenes - pharmacology</subject><subject>triterpenoid saponins</subject><subject>Tumor Cells, Cultured - drug effects</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNpF0DtvFDEUBWALgcgmUPAHwA10A9evedCFJYRIK4GUjZBorDseGwwz9sb2rMi_Z8IuUN3ifPcUh5BnDF4z4OxN2AEHCbB_QFZMcahq4OohWQGrRSXaWp6Q05x_AICATj0mJ4y3vJU1W5HpKscRi4-BYhhoLmk2ZU420-go7r3xIdP3f7LLt9QHuvclRVrmKabKh---9yWmO5pxF8O9HWzyeztQl-JEzw0aj8uPWZBH-4Q8cjhm-_R4z8jNh4vt-mO1-XR5tT7fVE7UqlQMoEcjnBRuaDploHWNVb0zEns1iJZjbwCQsZbXYJxpUDXM1s4pkD13XJyRV4feXYq3s81FTz4bO44YbJyzboRchmjEAp8f4dxPdtC75CdMd_rvQAt4eQSYDY4uYTA-_3ey47Ll90XVwflc7K9_Oaafum5Eo_T287X-uubbzbp7p78s_sXBO4wav6Wl8-aaAxPAQHWq7sRvKRSNnw</recordid><startdate>20030601</startdate><enddate>20030601</enddate><creator>Jayatilake, G.S</creator><creator>Freeberg, D.R</creator><creator>Liu, Z</creator><creator>Richheimer, S.L</creator><creator>Blake, M.E</creator><creator>Bailey, D.T</creator><creator>Haridas, V</creator><creator>Gutterman, J.U</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></search><sort><creationdate>20030601</creationdate><title>Isolation and structures of avicins D and G: in vitro tumor-inhibitory saponins derived from Acacia victoriae</title><author>Jayatilake, G.S ; Freeberg, D.R ; Liu, Z ; Richheimer, S.L ; Blake, M.E ; Bailey, D.T ; Haridas, V ; Gutterman, J.U</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f365t-100bac3f43fd795c08f7e5bfc4ab5d382abc00a118260cfc7a571e6ff504b2f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Acacia</topic><topic>Acacia - chemistry</topic><topic>Acacia victoriae</topic><topic>acacie acid</topic><topic>acid hydrolysis</topic><topic>apoptosis</topic><topic>Arizona</topic><topic>avicins</topic><topic>basic hydrolysis</topic><topic>biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>carboxylic acids</topic><topic>cell lines</topic><topic>chemical structure</topic><topic>cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fabaceae</topic><topic>General pharmacology</topic><topic>glycosides</topic><topic>Humans</topic><topic>Jurkat Cells</topic><topic>legumes</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>monosaccharides</topic><topic>monoterpenoids</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>oligosaccharides</topic><topic>Oligosaccharides - chemistry</topic><topic>Oligosaccharides - isolation & purification</topic><topic>Oligosaccharides - pharmacology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. 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Nat. Prod</addtitle><date>2003-06-01</date><risdate>2003</risdate><volume>66</volume><issue>6</issue><spage>779</spage><epage>783</epage><pages>779-783</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Two new saponins named avicins D (1) and G (2) were isolated from the seed pods of the desert legume plant Acacia victoriae. The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked to C-21 comprised of two monoterpene carboxylic acids and a quinovose moiety. Both compounds exhibited potent cytotoxicity (apoptosis) against human T-cell leukemia (Jurkat cells) in vitro.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>12828461</pmid><doi>10.1021/np020400v</doi><tpages>5</tpages></addata></record>
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source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	Acacia Acacia - chemistry Acacia victoriae acacie acid acid hydrolysis apoptosis Arizona avicins basic hydrolysis biochemical pathways Biological and medical sciences carboxylic acids cell lines chemical structure cytotoxicity Drug Screening Assays, Antitumor Fabaceae General pharmacology glycosides Humans Jurkat Cells legumes Medical sciences Molecular Structure monosaccharides monoterpenoids Nuclear Magnetic Resonance, Biomolecular oligosaccharides Oligosaccharides - chemistry Oligosaccharides - isolation & purification Oligosaccharides - pharmacology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals plant extracts Plants, Medicinal - chemistry prosaponins quinovose saponins Saponins - chemistry Saponins - isolation & purification Saponins - pharmacology seeds spectral analysis sugars Terpenes - chemistry Terpenes - isolation & purification Terpenes - pharmacology triterpenoid saponins Tumor Cells, Cultured - drug effects
title	Isolation and structures of avicins D and G: in vitro tumor-inhibitory saponins derived from Acacia victoriae
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