Parectadial: A Monoterpene Produced by a Madagascar Walkingstick Insect

1. Parectadial: A Monoterpene Produced by a Madagascar Walkingstick Insect Aaron T. Dosseya, Spencer S. Walseb, Oskar V. Conlec, and Arthur S. Edisond a Dept. of Biochem. and Molecular Biology, UF, Gainesville, FL 32610-0245 b Center for Medical, Agricultural and Veterinary Entomology, USDA-ARS, Gainesville, FL 32604 c Goldbachweg 24, 87538 Bolsterlang, Germany d McKnight Brain Institute, UF, Gainesville, FL 32611 and the NHMFL Many insects produce defensive chemicals to protect themselves against predators. Discovery of the structure of these compounds improves our understanding of the insect’s chemical ecology, and many naturally occurring biological chemicals also have important applications in agriculture or human health. One of the limiting factors in natural product identification is the sensitivity of NMR, and this study is another demonstration of the significant advantages that we have gained from the NHMFL 1-mm high temperature superconducting probe (Brey et al., JMR 179, 290-3, 2006). Parectatosoma mocquerysi is a rare walkingstick found in Madagascar, and its spray causes reddening and blistering when it hits exposed skin. Our external collaborator, Oskar Conle (Bolsterlang, Germany), is an expert in walkingsticks from around the world. He collected P. mocquerysi in Madagascar and then started rearing the animals in his lab in Germany. He sent us a small sample from 5-6 sprays, and Dr. Aaron Dossey, a postdoctoral associate in the Edison lab, and colleagues at the USDA labs determined that P. mocquerysi secretes glucose and a novel monoterpene that we named parectadial. Parectadial is similar in structure to perillyl alcohol and perillaldehyde, two natural products produced in plants that have multiple activities including the ability to kill or inhibit the growth of cancer cells. We tested parectadial, and in preliminary experiments it also inhibits or kills two different human cancer cell lines. We have obtained a provisional patent on the material and are pursuing more extensive testing. Female Parectatosoma mocquerysi. Photo by Oskar Conle. Parectadial. The S-isomer is the absolute configuration of the natural product. The structure was determined from the spray of 5-6 Parectatosoma mocquerysi animals using the 1-mm HTS probe. Dossey, A. T.; Walse, S. S.; Conle, O. V.; Edison, A. S., J. Nat. Prod. 70, 1335-1338 (2007)