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首页> 外文期刊>Proceedings of the National Academy of Sciences of the United States of America >DE NOVO BIOSYNTHESIS OF THE AGGREGATION PHEROMONE COMPONENTS IPSENOL AND IPSDIENOL BY THE PINE BARK BEETLES IPS PARACONFUSUS LANIER AND IPS PINI (SAY) (COLEOPTERA SCOLYTIDAE)
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DE NOVO BIOSYNTHESIS OF THE AGGREGATION PHEROMONE COMPONENTS IPSENOL AND IPSDIENOL BY THE PINE BARK BEETLES IPS PARACONFUSUS LANIER AND IPS PINI (SAY) (COLEOPTERA SCOLYTIDAE)

机译：松树皮甲虫IPS PARACONFUSUS LANIER和IPS PINI（SAY）的新合成生物信息素成分IPSENOL和IPSDIENOL（SOLE）（COLEOPTERA SCOLYTIDAE）

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摘要

The California five-spined ips, Ips paraconfusus Lanier, produces the myrcene-derived acyclic monoterpene alcohols ipsenol (2-methyl-6-methylene-7-octen-4-ol) and ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) as components of its aggregation pheromone, The pine engraver beetle, Ips pini (Say), produces only ipsdienol. Previous studies have shown that myrcene, a monoterpene in the pines colonized by these beetles, is a direct precursor to these pheromone components, In vivo radiolabeling studies reported here showed that male I, paraconfusus incorporated [1-C-14]acetate into ipsenol, ipsdienol, and amitinol (trans-2-methyl-6-methylene-3,7-octadien-2-ol), while male I. pini incorporated [1-C-14]acetate into ipsdienol and amitinol, Females of these species produced neither labeled nor unlabeled pheromone components. The purified radiolabeled monoterpene alcohols from males were identified by comparison of their HPLC and GC retention times with those of unlabeled standards, HPLC-purified fractions containing the individual radiolabeled components were analyzed by CC-MS and were shown to include only the pure alcohols, To further confirm that ipsdienol and ipsenol were radiolabeled, diastereomeric ester derivatives of the isolated alcohols were synthesized and analyzed by HPLC and GC-MS, After derivatization of the radiolabeled alcohols, the HPLC analysis demonstrated expected shifts in retention times with conservation of naturally occurring stereochemistry, The results provide direct evidence for de novo biosynthesis of ipsenol, ipsdienol and amitinol by bark beetles. [References: 39]
机译：加利福尼亚州的五纺ips，parapsusus Lanier，生产月桂烯衍生的无环单萜醇ipsenol（2-甲基-6-亚甲基-7-辛烯-4-醇）和ipsdienol（2-甲基-6-亚甲基-2， 7-octadien-4-ol）作为其聚集信息素的成分，松雕刻甲虫Ips pini（Say）仅产生ipsdienol。先前的研究表明，月桂烯是由这些甲虫定居的松树中的单萜，是这些信息素成分的直接前体。此处的体内放射标记研究显示，雄性I副配偶体将[1-C-14]乙酸酯掺入艾普森， ipsdienol和amitinol（反式-2-甲基-6-亚甲基-3,7-octadien-2-ol），而雄性Pin。I.将[1-C-14]乙酸酯掺入ipsdienol和Amitinol中，这些物种的雌性产生既没有标记也没有未标记的信息素成分。通过比较雄性的纯化的放射性标记的单萜醇与未标记的标准品的HPLC和GC保留时间，鉴定了含有单个放射性标记成分的HPLC纯化馏分，并通过CC-MS分析，结果表明仅包含纯醇，进一步确认已对ipsdienol和ipsenol进行了放射性标记，合成了分离出的醇的非对映体酯衍生物，并通过HPLC和GC-MS进行了分析。在将放射性标记的醇衍生化之后，HPLC分析表明保留时间的预期变化与自然立体化学的保留有关，结果为树皮甲虫从头开始生物合成ipsenol，ipsdienol和Amitinol提供了直接的证据。 [参考：39]

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