Neodictyoprolenol and Dictyoprolenol, the Possible Biosynthetic Intermediates of Dictyopterenes, in the Japanese Brown Algae Dictyopteris
Neodictyoprolenol [(-)-(3 S )-(1,5 Z, 8Z)-undecatrien-3-ol] and dictyoprolenol [ (-) - ( 3 S ) - (1,5 Z , 8Z )-undecadien-3-ol]), which had been proposed as possible biosynthetic intermediates of the sex pheromones of marine brown algae such as dictyopterene B [(-)-trans-1- ((1'E,3' Z )-he...
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| Veröffentlicht in: | Zeitschrift für Naturforschung C. A journal of biosciences 2001-01, Vol.56 (1), p.6-12 |
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| container_title | Zeitschrift für Naturforschung C. A journal of biosciences |
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| creator | Yamamoto, Yuuko Akakabe, Yoshihiko M atsui, Kenji Shimizu, Hiroshi Kajiwara, Tadahiko |
| description | Neodictyoprolenol [(-)-(3 S )-(1,5 Z, 8Z)-undecatrien-3-ol] and dictyoprolenol [ (-) - ( 3 S ) - (1,5 Z , 8Z )-undecadien-3-ol]), which had been proposed as possible biosynthetic intermediates of the sex pheromones of marine brown algae such as dictyopterene B [(-)-trans-1- ((1'E,3' Z )-hexadienyl)-2-vinylcyclopropane], D ' [(+ )-6 -((1' Z )-butenyl)-1,4 -cycloheptadiene] and C' [(+ )-6-butyl-1,4-cycloheptadiene], were again identified in the essential oils from Dictyopteris prolifera, D. latiscula, and in D. undulata, together with the C11-related volatile compounds such as neodictyoprolene, dictyoprolene and dictyopterenes. Incubation of D. prolifela preparation with racemic neodictyoprolenol and dictyoprolenol as substrates showed (S)-enantioselective decreases of the added substrates and increases in dictyopterenes. From these results, a possible pathway to form dictyopterenes is discussed. |
| doi_str_mv | 10.1515/znc-2001-1-202 |
| format | Article |
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Incubation of D. prolifela preparation with racemic neodictyoprolenol and dictyoprolenol as substrates showed (S)-enantioselective decreases of the added substrates and increases in dictyopterenes. From these results, a possible pathway to form dictyopterenes is discussed.</description><identifier>ISSN: 0939-5075</identifier><identifier>EISSN: 1865-7125</identifier><identifier>DOI: 10.1515/znc-2001-1-202</identifier><identifier>PMID: 11302216</identifier><language>eng</language><publisher>Germany: Verlag der Zeitschrift für Naturforschung</publisher><subject>Cycloheptanes - chemistry ; Cycloheptanes - metabolism ; Dictyopteris,Volatile Compounds ; Fatty Alcohols - chemistry ; Fatty Alcohols - metabolism ; Molecular Conformation ; Molecular Structure ; Phaeophyceae - chemistry ; Phaeophyceae - metabolism ; Pheromones ; Pheromones - chemistry</subject><ispartof>Zeitschrift für Naturforschung C. 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A journal of biosciences</title><addtitle>Z Naturforsch C J Biosci</addtitle><description>Neodictyoprolenol [(-)-(3 S )-(1,5 Z, 8Z)-undecatrien-3-ol] and dictyoprolenol [ (-) - ( 3 S ) - (1,5 Z , 8Z )-undecadien-3-ol]), which had been proposed as possible biosynthetic intermediates of the sex pheromones of marine brown algae such as dictyopterene B [(-)-trans-1- ((1'E,3' Z )-hexadienyl)-2-vinylcyclopropane], D ' [(+ )-6 -((1' Z )-butenyl)-1,4 -cycloheptadiene] and C' [(+ )-6-butyl-1,4-cycloheptadiene], were again identified in the essential oils from Dictyopteris prolifera, D. latiscula, and in D. undulata, together with the C11-related volatile compounds such as neodictyoprolene, dictyoprolene and dictyopterenes. Incubation of D. prolifela preparation with racemic neodictyoprolenol and dictyoprolenol as substrates showed (S)-enantioselective decreases of the added substrates and increases in dictyopterenes. From these results, a possible pathway to form dictyopterenes is discussed.</description><subject>Cycloheptanes - chemistry</subject><subject>Cycloheptanes - metabolism</subject><subject>Dictyopteris,Volatile Compounds</subject><subject>Fatty Alcohols - chemistry</subject><subject>Fatty Alcohols - metabolism</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Phaeophyceae - chemistry</subject><subject>Phaeophyceae - metabolism</subject><subject>Pheromones</subject><subject>Pheromones - chemistry</subject><issn>0939-5075</issn><issn>1865-7125</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1UDtPwzAYtBCIlsfKiDwxEfAjThqJhTdFCBhgtlzbKa5Su9iJUPkH_Gu-0iJgYDr7dHf67hDao-SICiqO373OGCE0owBsDfXpoBBZSZlYR31S8SoTpBQ9tJXShBBeiFJsoh6lnDBGiz76uLfBON3OwyyGxvrQYOUNvvhDHeL2xeLHkJIbNRafuZDmHqjWaTz0rY1Ta5xqbcKh_rYCa71Nh9j5L_etmin4gzuGN49Pm7Gyv7Qu7aCNWjXJ7q5wGz1fXT6d32R3D9fD89O7TOeCtFnO6tqoqhZVbpUpRUlzoxQ3tC6gLSdc54oPVMEHFStKrY3mo5yNCNEDLnLG-TY6WOZCu9fOplZOXdK2aeC80CVZlkQslgLh0VKoIzSPtpaz6KYqziUlcjG-hPHlYnxJARgY9lfJ3QgW-ZGv1gbByVLwphrobOw4dnN4yEnooofS_ySLAqDgn7V0lvI</recordid><startdate>20010101</startdate><enddate>20010101</enddate><creator>Yamamoto, Yuuko</creator><creator>Akakabe, Yoshihiko</creator><creator>M atsui, Kenji</creator><creator>Shimizu, Hiroshi</creator><creator>Kajiwara, Tadahiko</creator><general>Verlag der Zeitschrift für Naturforschung</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>7X8</scope></search><sort><creationdate>20010101</creationdate><title>Neodictyoprolenol and Dictyoprolenol, the Possible Biosynthetic Intermediates of Dictyopterenes, in the Japanese Brown Algae Dictyopteris</title><author>Yamamoto, Yuuko ; Akakabe, Yoshihiko ; M atsui, Kenji ; Shimizu, Hiroshi ; Kajiwara, Tadahiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c450t-42ffda9f594ead75714daa3d1f6939303c4a38a6389267ccdc3b42b00c8354233</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Cycloheptanes - chemistry</topic><topic>Cycloheptanes - metabolism</topic><topic>Dictyopteris,Volatile Compounds</topic><topic>Fatty Alcohols - chemistry</topic><topic>Fatty Alcohols - metabolism</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Phaeophyceae - chemistry</topic><topic>Phaeophyceae - metabolism</topic><topic>Pheromones</topic><topic>Pheromones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, Yuuko</creatorcontrib><creatorcontrib>Akakabe, Yoshihiko</creatorcontrib><creatorcontrib>M atsui, Kenji</creatorcontrib><creatorcontrib>Shimizu, Hiroshi</creatorcontrib><creatorcontrib>Kajiwara, Tadahiko</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Zeitschrift für Naturforschung C. 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A journal of biosciences</jtitle><addtitle>Z Naturforsch C J Biosci</addtitle><date>2001-01-01</date><risdate>2001</risdate><volume>56</volume><issue>1</issue><spage>6</spage><epage>12</epage><pages>6-12</pages><issn>0939-5075</issn><eissn>1865-7125</eissn><abstract>Neodictyoprolenol [(-)-(3 S )-(1,5 Z, 8Z)-undecatrien-3-ol] and dictyoprolenol [ (-) - ( 3 S ) - (1,5 Z , 8Z )-undecadien-3-ol]), which had been proposed as possible biosynthetic intermediates of the sex pheromones of marine brown algae such as dictyopterene B [(-)-trans-1- ((1'E,3' Z )-hexadienyl)-2-vinylcyclopropane], D ' [(+ )-6 -((1' Z )-butenyl)-1,4 -cycloheptadiene] and C' [(+ )-6-butyl-1,4-cycloheptadiene], were again identified in the essential oils from Dictyopteris prolifera, D. latiscula, and in D. undulata, together with the C11-related volatile compounds such as neodictyoprolene, dictyoprolene and dictyopterenes. Incubation of D. prolifela preparation with racemic neodictyoprolenol and dictyoprolenol as substrates showed (S)-enantioselective decreases of the added substrates and increases in dictyopterenes. From these results, a possible pathway to form dictyopterenes is discussed.</abstract><cop>Germany</cop><pub>Verlag der Zeitschrift für Naturforschung</pub><pmid>11302216</pmid><doi>10.1515/znc-2001-1-202</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Cycloheptanes - chemistry Cycloheptanes - metabolism Dictyopteris,Volatile Compounds Fatty Alcohols - chemistry Fatty Alcohols - metabolism Molecular Conformation Molecular Structure Phaeophyceae - chemistry Phaeophyceae - metabolism Pheromones Pheromones - chemistry |
| title | Neodictyoprolenol and Dictyoprolenol, the Possible Biosynthetic Intermediates of Dictyopterenes, in the Japanese Brown Algae Dictyopteris |
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