Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring
Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2005-02, Vol.68 (2), p.194-197 |
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| container_issue | 2 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 68 |
| creator | Kim, E.J Suh, K.M Kim, D.H Jung, E.J Seo, C.S Son, J.K Woo, M.H McLaughlin, J.L |
| description | Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines. |
| doi_str_mv | 10.1021/np040184l |
| format | Article |
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Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np040184l</identifier><identifier>PMID: 15730242</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>4-hydroxytrilobin ; acetogenins ; Animals ; anticarcinogenic activity ; Artemia - drug effects ; Asimina - chemistry ; Asimina triloba ; asimitrin ; Biological and medical sciences ; Cell Line, Tumor ; cell lines ; chemical analysis ; cytotoxicity ; Drug Screening Assays, Antitumor ; Electron Transport Complex I - antagonists & inhibitors ; furans ; Furans - chemistry ; Furans - isolation & purification ; Furans - pharmacology ; General pharmacology ; Humans ; lactones ; Lactones - chemistry ; Lactones - isolation & purification ; Lactones - pharmacology ; Maryland ; Medical sciences ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; plant extracts ; seeds ; Seeds - chemistry ; spectral analysis ; stereochemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2005-02, Vol.68 (2), p.194-197</ispartof><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16614086$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15730242$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, E.J</creatorcontrib><creatorcontrib>Suh, K.M</creatorcontrib><creatorcontrib>Kim, D.H</creatorcontrib><creatorcontrib>Jung, E.J</creatorcontrib><creatorcontrib>Seo, C.S</creatorcontrib><creatorcontrib>Son, J.K</creatorcontrib><creatorcontrib>Woo, M.H</creatorcontrib><creatorcontrib>McLaughlin, J.L</creatorcontrib><title>Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.</description><subject>4-hydroxytrilobin</subject><subject>acetogenins</subject><subject>Animals</subject><subject>anticarcinogenic activity</subject><subject>Artemia - drug effects</subject><subject>Asimina - chemistry</subject><subject>Asimina triloba</subject><subject>asimitrin</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>cell lines</subject><subject>chemical analysis</subject><subject>cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Electron Transport Complex I - antagonists & inhibitors</subject><subject>furans</subject><subject>Furans - chemistry</subject><subject>Furans - isolation & purification</subject><subject>Furans - pharmacology</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>lactones</subject><subject>Lactones - chemistry</subject><subject>Lactones - isolation & purification</subject><subject>Lactones - pharmacology</subject><subject>Maryland</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>seeds</subject><subject>Seeds - chemistry</subject><subject>spectral analysis</subject><subject>stereochemistry</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>eNp90M1u1DAQB3ALgei2cOAFwBfKhcD4M8mxqoAiVQXU9hzNJuOtIbG3dha6L8EzY7oL3DiNNP7pP55h7JmANwKkeBvWoEE0enzAFsJIqCxI85AtQFhVqcbqA3aY81cAUNCax-xAmFqB1HLBfp5kP_k5-cAxDFxXN9shxbtt6Yxx6cNrHugHX_qI_ey_U0EhBuwpbjIvZY4rCj5k7lKc-HxDPBMNmUfH74MD8l0S8nXMmXL2YcWxBOZqpjnh_Ti3SRh4-cPqCXvkcMz0dF-P2PX7d1enZ9X5pw8fT0_OK6eUmiscloMRhqxtrCAyPfag6kFq6jVR49qWgAYSUindomp0TVaSk6IZoNVGqCP2ape7TvF2Q3nuJp97GkcMv1fr6lqU6HKsIo__K22tTWulLvD5Hm6WEw3dOvkJ07b7c-sCXu4B5h5HV3buff7nrBUaGltctXM-z3T39x3TtzJM1aa7-nzZ1RdfNJxp210U_2LnHcYOV6lkXl9KEAqgbRvTtOoXdDSn3w</recordid><startdate>20050201</startdate><enddate>20050201</enddate><creator>Kim, E.J</creator><creator>Suh, K.M</creator><creator>Kim, D.H</creator><creator>Jung, E.J</creator><creator>Seo, C.S</creator><creator>Son, J.K</creator><creator>Woo, M.H</creator><creator>McLaughlin, J.L</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>20050201</creationdate><title>Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring</title><author>Kim, E.J ; Suh, K.M ; Kim, D.H ; Jung, E.J ; Seo, C.S ; Son, J.K ; Woo, M.H ; McLaughlin, J.L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f333t-adbd515e66861ee5cac037d24ec4ee8f99e0ede123349a3847e62ef218d094513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>4-hydroxytrilobin</topic><topic>acetogenins</topic><topic>Animals</topic><topic>anticarcinogenic activity</topic><topic>Artemia - drug effects</topic><topic>Asimina - chemistry</topic><topic>Asimina triloba</topic><topic>asimitrin</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>cell lines</topic><topic>chemical analysis</topic><topic>cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Electron Transport Complex I - antagonists & inhibitors</topic><topic>furans</topic><topic>Furans - chemistry</topic><topic>Furans - isolation & purification</topic><topic>Furans - pharmacology</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>lactones</topic><topic>Lactones - chemistry</topic><topic>Lactones - isolation & purification</topic><topic>Lactones - pharmacology</topic><topic>Maryland</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>seeds</topic><topic>Seeds - chemistry</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, E.J</creatorcontrib><creatorcontrib>Suh, K.M</creatorcontrib><creatorcontrib>Kim, D.H</creatorcontrib><creatorcontrib>Jung, E.J</creatorcontrib><creatorcontrib>Seo, C.S</creatorcontrib><creatorcontrib>Son, J.K</creatorcontrib><creatorcontrib>Woo, M.H</creatorcontrib><creatorcontrib>McLaughlin, J.L</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><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, E.J</au><au>Suh, K.M</au><au>Kim, D.H</au><au>Jung, E.J</au><au>Seo, C.S</au><au>Son, J.K</au><au>Woo, M.H</au><au>McLaughlin, J.L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2005-02-01</date><risdate>2005</risdate><volume>68</volume><issue>2</issue><spage>194</spage><epage>197</epage><pages>194-197</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>15730242</pmid><doi>10.1021/np040184l</doi><tpages>4</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | 4-hydroxytrilobin acetogenins Animals anticarcinogenic activity Artemia - drug effects Asimina - chemistry Asimina triloba asimitrin Biological and medical sciences Cell Line, Tumor cell lines chemical analysis cytotoxicity Drug Screening Assays, Antitumor Electron Transport Complex I - antagonists & inhibitors furans Furans - chemistry Furans - isolation & purification Furans - pharmacology General pharmacology Humans lactones Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Maryland Medical sciences Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals plant extracts seeds Seeds - chemistry spectral analysis stereochemistry |
| title | Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring |
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