Parectadial: A Monoterpene Produced by a Madagascar Walkingstick Insect

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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, German
y d McKnight Brain Institute, UF, Gainesville, F
L 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 insects 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 rar
e 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 s
tructure 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)