Cilek J E, Ikediobi C O, Hallmon C F, Johnson R, Onyeozili E N, Farah S M, Mazu T, Latinwo L M, Ayuk-Takem L, Berniers U R
John A. Mulrennan, Sr. Public Health Entomology Research & Education Center, College of Engineering Sciences, Technology, and Agriculture, Florida A&M University, 4000 Frankford Avenue, Panama City, FL 32405, USA.
J Am Mosq Control Assoc. 2011 Sep;27(3):256-62. doi: 10.2987/10-6097.1.
The compound 1-octen-3-ol is a known attractant of some mosquito species, which has led to the hypothesis that olfactory stimulation by this alkenol may be associated with the following structural elements: a terminal site of unsaturation or high electron density; a structural capability for hydrogen bonding, e.g., -OH, -NH2, NHR, NR2, etc.; a saturated hydrocarbon chain of a certain minimum length; and a certain relative distance between the region of high electron density and the alcohol (or other hydrogen-bonding) functional group. Using this logic, we synthesized 20 alkenol analogs based on the octenol double-bonded carbon skeleton. The attraction of female Aedes albopictus and Culex quinquefasciatus to these analogs was compared with 1-octen-3-ol as a standard in semi-field trials. For both species, collections from Mosquito Magnet-X (MMX) suction traps baited with the alkenol analogs in the absence of carbon dioxide were not significantly different from octenol-only baited traps, with the exception of (Z)-3-hepten-1-ol which collected significantly more Ae. albopictus. In the presence of CO2, most of the collections from traps baited with an alkenol were considerably increased for both species but not different from octenol plus CO2, with the exception of Ae. albopictus where (Z)-3-decen-1-ol, (Z)-4-hexen-1-ol, 7-octen-2-ol, and 8-nonen-3-ol significantly depressed trap catches. Although no clearly identifiable structure-activity relationship could be determined from our collected data, we did find that MMX traps baited with carbon dioxide and 4-penten-2-ol or (E)-2-decen-4-ol significantly enhanced Cx. quinquefasciatus collections up to nearly 3-fold compared with octenol plus carbon dioxide.
化合物1-辛烯-3-醇是一些蚊虫种类已知的引诱剂,这引发了一种假说,即这种链烯醇引起的嗅觉刺激可能与以下结构要素有关:不饱和末端位点或高电子密度;氢键形成的结构能力,例如-OH、-NH2、NHR、NR2等;一定最小长度的饱和烃链;以及高电子密度区域与醇(或其他氢键形成)官能团之间的特定相对距离。基于这种逻辑,我们以辛烯醇双键碳骨架为基础合成了20种链烯醇类似物。在半野外试验中,将白纹伊蚊和致倦库蚊雌蚊对这些类似物的吸引力与作为标准的1-辛烯-3-醇进行了比较。对于这两个物种,在没有二氧化碳的情况下,用链烯醇类似物诱饵的灭蚊磁场-X(MMX)吸捕器捕获的蚊虫与仅用辛烯醇诱饵的捕蚊器相比没有显著差异,但(Z)-3-庚烯-1-醇捕获的白纹伊蚊明显更多。在有二氧化碳的情况下,两个物种用链烯醇诱饵的捕蚊器捕获的大多数蚊虫数量都大幅增加,但与辛烯醇加二氧化碳的情况没有差异,不过白纹伊蚊对(Z)-3-癸烯-1-醇、(Z)-4-己烯-1-醇、7-辛烯-2-醇和8-壬烯-3-醇的捕获量显著降低。尽管从我们收集的数据中无法确定明确的构效关系,但我们确实发现,用二氧化碳和4-戊烯-2-醇或(E)-2-癸烯-4-醇诱饵的MMX捕蚊器捕获的致倦库蚊数量与辛烯醇加二氧化碳相比显著增加了近三倍。