Chemical Constituents of Avicennia alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues
Three new naphthoquinones and their analogues, named avicequinone-A (1), -B (2), -C (3), and avicenol-A (4), -B (5), -C (6), respectively, were isolated from the stem bark of Avicennia alba (Avicenniaceae) collected in Singapore, and their structures were elucidated by means of spectral methods.Gill...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2000/03/01, Vol.48(3), pp.339-343 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | ITO, Chihiro KATSUNO, Shinya KONDO, Yuichi TAN, Hugh T.-W. FURUKAWA, Hiroshi |
| description | Three new naphthoquinones and their analogues, named avicequinone-A (1), -B (2), -C (3), and avicenol-A (4), -B (5), -C (6), respectively, were isolated from the stem bark of Avicennia alba (Avicenniaceae) collected in Singapore, and their structures were elucidated by means of spectral methods.Gillan and co-workers have proposed that the structures of the new phytoalexins isolated from Avicennia marina are 1, 2-naphthoquinones 8 and 9. Our synthetic and spectrometric studies showed that these structures should be revised respectively to 1, 4-naphthoquinones 2 and 3, named avicequinone-B and -C by us. |
| doi_str_mv | 10.1248/cpb.48.339 |
| format | Article |
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Our synthetic and spectrometric studies showed that these structures should be revised respectively to 1, 4-naphthoquinones 2 and 3, named avicequinone-B and -C by us.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.48.339</identifier><identifier>PMID: 10726853</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Analytical, structural and metabolic biochemistry ; Aromatic and heterocyclic compounds ; Avicennia alba ; Avicenniaceae ; avicenol ; avicequinone ; Biological and medical sciences ; Fundamental and applied biological sciences. Psychology ; Heterocyclic compounds, pigments ; Magnetic Resonance Spectroscopy ; naphthoquinone ; Naphthoquinones - chemistry ; Naphthoquinones - isolation & purification ; Other biological molecules ; phytoalexin ; Plant Epidermis - chemistry ; Plants, Medicinal - chemistry ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2000/03/01, Vol.48(3), pp.339-343</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>2000 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2000</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c502t-c828efab383167e866f08f7ee2ef3fa6fa5fcc179b817d0a3689b3ce735620a33</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1342020$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10726853$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>ITO, Chihiro</creatorcontrib><creatorcontrib>KATSUNO, Shinya</creatorcontrib><creatorcontrib>KONDO, Yuichi</creatorcontrib><creatorcontrib>TAN, Hugh T.-W.</creatorcontrib><creatorcontrib>FURUKAWA, Hiroshi</creatorcontrib><title>Chemical Constituents of Avicennia alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Three new naphthoquinones and their analogues, named avicequinone-A (1), -B (2), -C (3), and avicenol-A (4), -B (5), -C (6), respectively, were isolated from the stem bark of Avicennia alba (Avicenniaceae) collected in Singapore, and their structures were elucidated by means of spectral methods.Gillan and co-workers have proposed that the structures of the new phytoalexins isolated from Avicennia marina are 1, 2-naphthoquinones 8 and 9. Our synthetic and spectrometric studies showed that these structures should be revised respectively to 1, 4-naphthoquinones 2 and 3, named avicequinone-B and -C by us.</description><subject>Analytical, structural and metabolic biochemistry</subject><subject>Aromatic and heterocyclic compounds</subject><subject>Avicennia alba</subject><subject>Avicenniaceae</subject><subject>avicenol</subject><subject>avicequinone</subject><subject>Biological and medical sciences</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heterocyclic compounds, pigments</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>naphthoquinone</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - isolation & purification</subject><subject>Other biological molecules</subject><subject>phytoalexin</subject><subject>Plant Epidermis - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU9v1DAQxS0EokvhwgdAkUAckHbxn8R2jquoQKWqHCjnaOIdN15l7cV2Cnx73GZFERePrPebeaN5hLxmdMN4rT-a47Cp9UaI9glZMVGrdcO5eEpWlNJ2zYUUZ-RFSntKeUOVeE7OGFVc6kasyK9uxIMzMFVd8Cm7PKPPqQq22t45g947qGAaYFNdpjBBdsFX4HfVtxxnk-dYGi-m2bjdIpW-a_xZXcNxzGP4MTsfPKaHjpsRXay2HqZwO2N6SZ5ZmBK-OtVz8v3TxU33ZX319fNlt71am4byvDaaa7QwCC2YVKiltFRbhcjRCgvSQmONYaodNFM7CkLqdhAGlWgkL19xTt4vc4-x7IMp9weXDE4TeAxz6hVtNaesLeDb_8B9mGNZN_WsllRwJVVTqA8LZWJIKaLtj9EdIP7uGe3v0-hLGn0pJY0CvzmNnIcD7v5Bl_MX4N0JgFQysBG8cemREzWnnBasW7B9ynCLf3WI2ZkJ7y1Z2-gH2-Up7o_qCLFHL_4AHOOqyw</recordid><startdate>20000301</startdate><enddate>20000301</enddate><creator>ITO, Chihiro</creator><creator>KATSUNO, Shinya</creator><creator>KONDO, Yuichi</creator><creator>TAN, Hugh T.-W.</creator><creator>FURUKAWA, Hiroshi</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><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>20000301</creationdate><title>Chemical Constituents of Avicennia alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues</title><author>ITO, Chihiro ; KATSUNO, Shinya ; KONDO, Yuichi ; TAN, Hugh T.-W. ; FURUKAWA, Hiroshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c502t-c828efab383167e866f08f7ee2ef3fa6fa5fcc179b817d0a3689b3ce735620a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Analytical, structural and metabolic biochemistry</topic><topic>Aromatic and heterocyclic compounds</topic><topic>Avicennia alba</topic><topic>Avicenniaceae</topic><topic>avicenol</topic><topic>avicequinone</topic><topic>Biological and medical sciences</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heterocyclic compounds, pigments</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>naphthoquinone</topic><topic>Naphthoquinones - chemistry</topic><topic>Naphthoquinones - isolation & purification</topic><topic>Other biological molecules</topic><topic>phytoalexin</topic><topic>Plant Epidermis - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ITO, Chihiro</creatorcontrib><creatorcontrib>KATSUNO, Shinya</creatorcontrib><creatorcontrib>KONDO, Yuichi</creatorcontrib><creatorcontrib>TAN, Hugh T.-W.</creatorcontrib><creatorcontrib>FURUKAWA, Hiroshi</creatorcontrib><collection>Pascal-Francis</collection><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>ITO, Chihiro</au><au>KATSUNO, Shinya</au><au>KONDO, Yuichi</au><au>TAN, Hugh T.-W.</au><au>FURUKAWA, Hiroshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Constituents of Avicennia alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2000-03-01</date><risdate>2000</risdate><volume>48</volume><issue>3</issue><spage>339</spage><epage>343</epage><pages>339-343</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Three new naphthoquinones and their analogues, named avicequinone-A (1), -B (2), -C (3), and avicenol-A (4), -B (5), -C (6), respectively, were isolated from the stem bark of Avicennia alba (Avicenniaceae) collected in Singapore, and their structures were elucidated by means of spectral methods.Gillan and co-workers have proposed that the structures of the new phytoalexins isolated from Avicennia marina are 1, 2-naphthoquinones 8 and 9. Our synthetic and spectrometric studies showed that these structures should be revised respectively to 1, 4-naphthoquinones 2 and 3, named avicequinone-B and -C by us.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>10726853</pmid><doi>10.1248/cpb.48.339</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Analytical, structural and metabolic biochemistry Aromatic and heterocyclic compounds Avicennia alba Avicenniaceae avicenol avicequinone Biological and medical sciences Fundamental and applied biological sciences. Psychology Heterocyclic compounds, pigments Magnetic Resonance Spectroscopy naphthoquinone Naphthoquinones - chemistry Naphthoquinones - isolation & purification Other biological molecules phytoalexin Plant Epidermis - chemistry Plants, Medicinal - chemistry Spectrophotometry, Infrared Spectrophotometry, Ultraviolet |
| title | Chemical Constituents of Avicennia alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues |
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