Submitted to: Natural Product Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/21/2014
Publication Date: 10/21/2014
Citation: Khanna, H., Chauhan, K.R. 2014. Biobased Lactams as Novel Arthropod Repellents. Natural Product Communications. 9:1671-1672.
Interpretive Summary: The plant in the mint family known as catnip produces certain volatile chemicals (nepetalactones) which belong to a class of compounds known as cyclopentanoid monoterpenes. Nepetalactones could be important building blocks for the synthesis of natural product pesticides. However because of their complex synthesis and limited availability as natural products, their use as synthetic precursors is limited. We have developed an easy and simple synthetic method to obtain nepetalactam and analogues cyclic monoterpenes in useable quantities by utilizing nepetalactones, which we had isolated from catnip oil. Availability of these compounds is proving very useful in the quantitative structure activity relationship studies of the arthropod pest control candidates and may ultimately help in the identification of new class of pest control agents for scientists and pest management companies.
Technical Abstract: Cyclopentanoid monoterpenes like nepetalactones derived from catnip are an attractive source of volatile repellents against arthropods. Formal studies documenting the role played by the stereochemical elements on the monoterpene skeleton towards mosquito repellency are lacking. In this study we present the synthesis and activity of two isomers, cis, trans and trans, cis-nepetalactams towards Aedes aegypti. Nepetalactams are the nitrogen analogs of nepetalactones and belong to a yet unexplored class of cyclopentanoid monoterpenes. Individual stereoisomers of alkylated dihydronepetalactams that contained an additional chiral center, 5S/5R cis, trans-dihydronepetalactams and 5S/5R trans, cis-dihydronepetalactams were also prepared and tested against Ae. aegypti to analyze the effect of an additional chiral center has on deterrence activity of the individual isomers.