Cactoblastis cactorum is an invasive insect currently inhabiting the southeastern part of the United States. Its western migration poses a threat to its host, the Optunia cactus, which is a staple food crop in Mexico. We have previously shown that chemical signaling between individual larvae is essential for their survival and have determined that a family of compounds present in the mandibular glands of the larvae is responsible for this activity. Preliminary analysis of this bioactive fraction by HPLC and NMR indicated the presence of about 20 structurally related acylcyclohexane diones with fatty acid-like side chains. To firmly establish the length and degree of unsaturation of the side chains, the compounds were analyzed by LC-MS. Although the position of the alkene unsaturation could not be determined by fragmentation of the native compounds, the structures of the compounds were established by comparing the MS/MS CID fragmentation patterns of epoxide derivatives of representative synthetic compounds with epoxide derivatives of the compounds isolated from the animal.

Structure determination of a family of bioactive lipids isolated from the larvae of the Argentine cactus moth, Cactoblastis cactorum

253rd National Meeting (2017)

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