Lignans of Chamaecyparis obtusa
Heartwood of Chamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan,hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartw...
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| Veröffentlicht in: | Journal of wood science 2001-01, Vol.47 (6), p.476-482 |
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| container_title | Journal of wood science |
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| creator | Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.) Choi, D.H Mikame, K Okunishi, T Suzuki, S Ohashi, H Umezawa, T Shimada, M |
| description | Heartwood of Chamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan,hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans - xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and matairesinol (11) - were isolated from young shoots of Chamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2,4, 5, 7, 9, 10, and 11) were isolated from this plant for the first time. Chiral high-performance liquid chromatographic analysis showed that 8, 9, 10, and 11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of 8 are discussed. |
| doi_str_mv | 10.1007/BF00767901 |
| format | Article |
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(Kyoto Univ., Uji (Japan). Wood Research Inst.) ; Choi, D.H ; Mikame, K ; Okunishi, T ; Suzuki, S ; Ohashi, H ; Umezawa, T ; Shimada, M</creator><creatorcontrib>Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.) ; Choi, D.H ; Mikame, K ; Okunishi, T ; Suzuki, S ; Ohashi, H ; Umezawa, T ; Shimada, M</creatorcontrib><description>Heartwood of Chamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan,hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans - xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and matairesinol (11) - were isolated from young shoots of Chamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2,4, 5, 7, 9, 10, and 11) were isolated from this plant for the first time. Chiral high-performance liquid chromatographic analysis showed that 8, 9, 10, and 11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of 8 are discussed.</description><identifier>ISSN: 1435-0211</identifier><identifier>EISSN: 1611-4663</identifier><identifier>DOI: 10.1007/BF00767901</identifier><language>eng</language><publisher>Tokyo: Springer</publisher><subject>Agronomy. Soil science and plant productions ; Biological and medical sciences ; CHAMAECYPARIS OBTUSA ; Chemical constitution ; Economic plant physiology ; EXTRACTS ; Fundamental and applied biological sciences. Psychology ; HEARTWOOD ; LIGNANS ; MASS SPECTROMETRY ; NMR SPECTROSCOPY ; Plant physiology and development</subject><ispartof>Journal of wood science, 2001-01, Vol.47 (6), p.476-482</ispartof><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13436435$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.)</creatorcontrib><creatorcontrib>Choi, D.H</creatorcontrib><creatorcontrib>Mikame, K</creatorcontrib><creatorcontrib>Okunishi, T</creatorcontrib><creatorcontrib>Suzuki, S</creatorcontrib><creatorcontrib>Ohashi, H</creatorcontrib><creatorcontrib>Umezawa, T</creatorcontrib><creatorcontrib>Shimada, M</creatorcontrib><title>Lignans of Chamaecyparis obtusa</title><title>Journal of wood science</title><description>Heartwood of Chamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan,hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans - xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and matairesinol (11) - were isolated from young shoots of Chamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2,4, 5, 7, 9, 10, and 11) were isolated from this plant for the first time. Chiral high-performance liquid chromatographic analysis showed that 8, 9, 10, and 11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of 8 are discussed.</description><subject>Agronomy. Soil science and plant productions</subject><subject>Biological and medical sciences</subject><subject>CHAMAECYPARIS OBTUSA</subject><subject>Chemical constitution</subject><subject>Economic plant physiology</subject><subject>EXTRACTS</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HEARTWOOD</subject><subject>LIGNANS</subject><subject>MASS SPECTROMETRY</subject><subject>NMR SPECTROSCOPY</subject><subject>Plant physiology and development</subject><issn>1435-0211</issn><issn>1611-4663</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><recordid>eNotTz1PwzAUtBBIlMLCjujCaHjPz7GTEaKWD0WCAeboxR8lqE2juAz991gqy93pdDrdCXGNcI8A9uFpldHYCvBEzNAgSm0MnWatqZCgEM_FRUo_kKW2NBO3Tb8eeEiLXVzU37zl4A4jT302uv1v4ktxFnmTwtU_z8XXavlZv8jm_fm1fmxkVAR7WXbeaeagfPTgjVZcOeehpE6Rj4ABrS08mIoqJobQmUpry4VlMsp4prm4O_aOnBxv4sSD61M7Tv2Wp0OLpMnkCzl3c8xF3rW8zkPbtw-V7wCQLUr6AyjYR4A</recordid><startdate>20010101</startdate><enddate>20010101</enddate><creator>Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.)</creator><creator>Choi, D.H</creator><creator>Mikame, K</creator><creator>Okunishi, T</creator><creator>Suzuki, S</creator><creator>Ohashi, H</creator><creator>Umezawa, T</creator><creator>Shimada, M</creator><general>Springer</general><scope>FBQ</scope><scope>IQODW</scope></search><sort><creationdate>20010101</creationdate><title>Lignans of Chamaecyparis obtusa</title><author>Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.) ; Choi, D.H ; Mikame, K ; Okunishi, T ; Suzuki, S ; Ohashi, H ; Umezawa, T ; Shimada, M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f230t-8bdc4aae2dfd0d642a9ccd083b23df01e1775d06939a3a0eb69447a57a3626da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Biological and medical sciences</topic><topic>CHAMAECYPARIS OBTUSA</topic><topic>Chemical constitution</topic><topic>Economic plant physiology</topic><topic>EXTRACTS</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HEARTWOOD</topic><topic>LIGNANS</topic><topic>MASS SPECTROMETRY</topic><topic>NMR SPECTROSCOPY</topic><topic>Plant physiology and development</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.)</creatorcontrib><creatorcontrib>Choi, D.H</creatorcontrib><creatorcontrib>Mikame, K</creatorcontrib><creatorcontrib>Okunishi, T</creatorcontrib><creatorcontrib>Suzuki, S</creatorcontrib><creatorcontrib>Ohashi, H</creatorcontrib><creatorcontrib>Umezawa, T</creatorcontrib><creatorcontrib>Shimada, M</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><jtitle>Journal of wood science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Takaku, N. (Kyoto Univ., Uji (Japan). Wood Research Inst.)</au><au>Choi, D.H</au><au>Mikame, K</au><au>Okunishi, T</au><au>Suzuki, S</au><au>Ohashi, H</au><au>Umezawa, T</au><au>Shimada, M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lignans of Chamaecyparis obtusa</atitle><jtitle>Journal of wood science</jtitle><date>2001-01-01</date><risdate>2001</risdate><volume>47</volume><issue>6</issue><spage>476</spage><epage>482</epage><pages>476-482</pages><issn>1435-0211</issn><eissn>1611-4663</eissn><abstract>Heartwood of Chamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan,hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans - xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and matairesinol (11) - were isolated from young shoots of Chamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2,4, 5, 7, 9, 10, and 11) were isolated from this plant for the first time. Chiral high-performance liquid chromatographic analysis showed that 8, 9, 10, and 11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of 8 are discussed.</abstract><cop>Tokyo</cop><pub>Springer</pub><doi>10.1007/BF00767901</doi><tpages>7</tpages></addata></record> |
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; SpringerLink Journals - AutoHoldings |
| subjects | Agronomy. Soil science and plant productions Biological and medical sciences CHAMAECYPARIS OBTUSA Chemical constitution Economic plant physiology EXTRACTS Fundamental and applied biological sciences. Psychology HEARTWOOD LIGNANS MASS SPECTROMETRY NMR SPECTROSCOPY Plant physiology and development |
| title | Lignans of Chamaecyparis obtusa |
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