Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase
Three new eudesmane type sesquiterpenoid lindenanolides E (1), F (2) and G (3), and two new aporphine alkaloid lindechunines A (18) and B (20) were isolated from roots of Lindera chunii MERR., together with seven known sesquiterpenes including a new naturally-occurring lindenanolide H (4) and eight...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2002, Vol.50(9), pp.1195-1200 |
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| creator | Zhang, Chao-feng Nakamura, Norio Tewtrakul, Supinya Hattori, Masao Sun, Qi-shi Wang, Zheng-tao Fujiwara, Tamio |
| description | Three new eudesmane type sesquiterpenoid lindenanolides E (1), F (2) and G (3), and two new aporphine alkaloid lindechunines A (18) and B (20) were isolated from roots of Lindera chunii MERR., together with seven known sesquiterpenes including a new naturally-occurring lindenanolide H (4) and eight known aporphine alkaloids. The structures of these compounds were determined by spectroscopic means. Of the isolated compounds, hernandonine (14), laurolistine (16), 7-oxohernangerine (17) and lindechunine A (18) showed significant anti-human immunodeficiency virus type 1 (HIV-1) integrase activity with IC50 values of 16.3, 7.7, 18.2 and 21.1 μM, respectively. The major alkaloids presented in the roots of L. chunii were quantitatively analyzed by an HPLC method. |
| doi_str_mv | 10.1248/cpb.50.1195 |
| format | Article |
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The structures of these compounds were determined by spectroscopic means. Of the isolated compounds, hernandonine (14), laurolistine (16), 7-oxohernangerine (17) and lindechunine A (18) showed significant anti-human immunodeficiency virus type 1 (HIV-1) integrase activity with IC50 values of 16.3, 7.7, 18.2 and 21.1 μM, respectively. The major alkaloids presented in the roots of L. chunii were quantitatively analyzed by an HPLC method.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.50.1195</identifier><identifier>PMID: 12237535</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; aporphine alkaloid ; Chromatography, High Pressure Liquid ; HIV Integrase - chemistry ; HIV Integrase Inhibitors - chemistry ; HIV Integrase Inhibitors - isolation & purification ; HIV Integrase Inhibitors - pharmacology ; HIV-1 integrase ; Lauraceae ; Lindera - chemistry ; Lindera chunii ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Models, Molecular ; Molecular Conformation ; Plant Extracts - chemistry ; Plant Roots - chemistry ; sesquiterpene ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; Spectrophotometry, Ultraviolet</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2002, Vol.50(9), pp.1195-1200</ispartof><rights>2002 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2002</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c497t-bea33d0bbd539197e71564f8bdc6edaa28507e5d1cb8e60f360fd886d86a553f3</citedby><cites>FETCH-LOGICAL-c497t-bea33d0bbd539197e71564f8bdc6edaa28507e5d1cb8e60f360fd886d86a553f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,1877,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12237535$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Chao-feng</creatorcontrib><creatorcontrib>Nakamura, Norio</creatorcontrib><creatorcontrib>Tewtrakul, Supinya</creatorcontrib><creatorcontrib>Hattori, Masao</creatorcontrib><creatorcontrib>Sun, Qi-shi</creatorcontrib><creatorcontrib>Wang, Zheng-tao</creatorcontrib><creatorcontrib>Fujiwara, Tamio</creatorcontrib><title>Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Three new eudesmane type sesquiterpenoid lindenanolides E (1), F (2) and G (3), and two new aporphine alkaloid lindechunines A (18) and B (20) were isolated from roots of Lindera chunii MERR., together with seven known sesquiterpenes including a new naturally-occurring lindenanolide H (4) and eight known aporphine alkaloids. The structures of these compounds were determined by spectroscopic means. Of the isolated compounds, hernandonine (14), laurolistine (16), 7-oxohernangerine (17) and lindechunine A (18) showed significant anti-human immunodeficiency virus type 1 (HIV-1) integrase activity with IC50 values of 16.3, 7.7, 18.2 and 21.1 μM, respectively. The major alkaloids presented in the roots of L. chunii were quantitatively analyzed by an HPLC method.</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>aporphine alkaloid</subject><subject>Chromatography, High Pressure Liquid</subject><subject>HIV Integrase - chemistry</subject><subject>HIV Integrase Inhibitors - chemistry</subject><subject>HIV Integrase Inhibitors - isolation & purification</subject><subject>HIV Integrase Inhibitors - pharmacology</subject><subject>HIV-1 integrase</subject><subject>Lauraceae</subject><subject>Lindera - chemistry</subject><subject>Lindera chunii</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Roots - chemistry</subject><subject>sesquiterpene</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkMtLAzEQh4Motj5O3mVB8CKryWazj5ulqC0UPPi4hmwy203dZtskK_S_N7VVwcNkBubjY_JD6ILgW5KkxZ1cVbcszKRkB2hIaJrHLEnoIRpijMs4oRkdoBPnFhgnDOf0GA1I2OeMsiFqXsCte-3BrsCAi4RR0aj9EG2nlYtq2y2jmTYKrIhk0xutv4nXBrSNpqbRlfad3UQj6fWn9nprmAttnI8m0_eYBMbD3AoHZ-ioFq2D830_RW-PD6_jSTx7fpqOR7NYpmXu4woEpQpXlWK0JGUOOWFZWheVkhkoIZIifAGYIrIqIMM1DaWKIlNFJhijNT1F1zvvynbrHpznS-0ktK0w0PWO5wkugzMP4NU_cNH11oTbOEkzTNMiLUmgbnaUtJ1zFmq-snop7IYTzLfx8xA_Z2EO8Qf6cu_sqyWoP3afdwDud8DCeTGHX0BYr2ULP7Jy92ydf6tGWA6GfgHdNpfE</recordid><startdate>20020901</startdate><enddate>20020901</enddate><creator>Zhang, Chao-feng</creator><creator>Nakamura, Norio</creator><creator>Tewtrakul, Supinya</creator><creator>Hattori, Masao</creator><creator>Sun, Qi-shi</creator><creator>Wang, Zheng-tao</creator><creator>Fujiwara, Tamio</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20020901</creationdate><title>Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase</title><author>Zhang, Chao-feng ; Nakamura, Norio ; Tewtrakul, Supinya ; Hattori, Masao ; Sun, Qi-shi ; Wang, Zheng-tao ; Fujiwara, Tamio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c497t-bea33d0bbd539197e71564f8bdc6edaa28507e5d1cb8e60f360fd886d86a553f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>aporphine alkaloid</topic><topic>Chromatography, High Pressure Liquid</topic><topic>HIV Integrase - chemistry</topic><topic>HIV Integrase Inhibitors - chemistry</topic><topic>HIV Integrase Inhibitors - isolation & purification</topic><topic>HIV Integrase Inhibitors - pharmacology</topic><topic>HIV-1 integrase</topic><topic>Lauraceae</topic><topic>Lindera - chemistry</topic><topic>Lindera chunii</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Roots - chemistry</topic><topic>sesquiterpene</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Chao-feng</creatorcontrib><creatorcontrib>Nakamura, Norio</creatorcontrib><creatorcontrib>Tewtrakul, Supinya</creatorcontrib><creatorcontrib>Hattori, Masao</creatorcontrib><creatorcontrib>Sun, Qi-shi</creatorcontrib><creatorcontrib>Wang, Zheng-tao</creatorcontrib><creatorcontrib>Fujiwara, Tamio</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Chao-feng</au><au>Nakamura, Norio</au><au>Tewtrakul, Supinya</au><au>Hattori, Masao</au><au>Sun, Qi-shi</au><au>Wang, Zheng-tao</au><au>Fujiwara, Tamio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2002-09-01</date><risdate>2002</risdate><volume>50</volume><issue>9</issue><spage>1195</spage><epage>1200</epage><pages>1195-1200</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Three new eudesmane type sesquiterpenoid lindenanolides E (1), F (2) and G (3), and two new aporphine alkaloid lindechunines A (18) and B (20) were isolated from roots of Lindera chunii MERR., together with seven known sesquiterpenes including a new naturally-occurring lindenanolide H (4) and eight known aporphine alkaloids. The structures of these compounds were determined by spectroscopic means. Of the isolated compounds, hernandonine (14), laurolistine (16), 7-oxohernangerine (17) and lindechunine A (18) showed significant anti-human immunodeficiency virus type 1 (HIV-1) integrase activity with IC50 values of 16.3, 7.7, 18.2 and 21.1 μM, respectively. The major alkaloids presented in the roots of L. chunii were quantitatively analyzed by an HPLC method.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>12237535</pmid><doi>10.1248/cpb.50.1195</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology aporphine alkaloid Chromatography, High Pressure Liquid HIV Integrase - chemistry HIV Integrase Inhibitors - chemistry HIV Integrase Inhibitors - isolation & purification HIV Integrase Inhibitors - pharmacology HIV-1 integrase Lauraceae Lindera - chemistry Lindera chunii Magnetic Resonance Spectroscopy Mass Spectrometry Models, Molecular Molecular Conformation Plant Extracts - chemistry Plant Roots - chemistry sesquiterpene Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology Spectrophotometry, Ultraviolet |
| title | Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase |
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