Determination by HPLC fluorescence analysis of the natural enantiomers of sex pheromones in the New World screwworm fly, Cochliomyia hominivorax
Determination by HPLC fluorescence analysis of the natural enantiomers of sex pheromones in the New World screwworm fly, Cochliomyia hominivorax
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高效液相色谱荧光分析法测定新世界螺旋蝇 Cochliomyia hominivorax 性信息素的天然对映体
DOI：
10.1111/j.1365-2915.2008.00781.x
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发表时间：
2009
影响因子：
1.9
通讯作者：
D. Berkebile
中科院分区：
文献类型：
--
作者：
K. Akasaka;D. Carlson;T. Ohtaka;H. Ohrui;K. Mori;D. Berkebile
摘要 针对雄性新大陆螺旋虫 Cochliomyia hominivorax (Coquerel) 果蝇的六种外消旋合成候选性信息素化合物的生物测定表明，与其他四种异构体乙酰氧基二十烷和较大的脂肪族酮相比，6-乙酰氧基-19-甲基二十烷和 7-乙酰氧基-15-甲基二十烷具有最有效的生物活性。由于所有这些甲基支链化合物都具有两个不对称碳和四种可能的对映体，因此天然对映体的表征至关重要。天然性信息素的两种最具生物活性的异构体的所有四种对映体均被合成用于生物测定。用不同的荧光试剂水解和衍生这些对映体，然后进行柱切换高效液相色谱。使用在低于环境温度下保持的两个不同极性的连接反相柱可以很好地分离每种对映体。这种应用于天然材料的分析是成功的，因为在最近定殖的雌性果蝇的提取物中检测到了(6R,19R)-6-乙酰氧基-19-甲基正二十烷，以及(7R,15R)-和(7R,15S)-7-乙酰氧基-15-甲基正二十烷。
Abstract Bioassays of six racemic synthesized candidate sex pheromone compounds against male New World screwworm Cochliomyia hominivorax (Coquerel) flies showed that the most potent bioactivity was found with 6‐acetoxy‐19‐methylnonacosane and 7‐acetoxy‐15‐methylnonacosane compared with four other isomeric acetoxy nonacosanes and a larger aliphatic ketone. As all these methyl‐branched compounds have two asymmetric carbons and four possible enantiomers, characterization of the natural enantiomers was essential. All four enantiomers for the two most bioactive isomers of the natural sex pheromone were synthesized for bioassay. Hydrolysis and derivatization of these enantiomers with different fluorescent reagents was followed by column‐switched high‐performance liquid chromatography. The use of two linked, reversed‐phase columns of different polarity held at sub‐ambient temperatures allowed good separation of each enantiomer. This analysis applied to natural material was successful, as (6R,19R)‐6‐acetoxy‐19‐methylnonanocosane, and (7R,15R)‐ and (7R,15S)‐7‐acetoxy‐15‐methylnonanocosane were detected in extracts of recently colonized female flies.