Parectadial, a monoterpenoid from the defensive spray of Parectatosoma mocquerysi.
The defensive secretion of Parectatosoma mocquerysi, a walkingstick insect from Madagascar, was determined to contain glucose, water, and a new monoterpene, parectadial, (4S)-(3-oxoprop-1-en-2-yl)cyclohex-1-enecarbaldehyde. Here, we describe the elucidation of parectadial's molecular structure and absolute configuration via microsample NMR technology, GC-MS, CD, chiral GC-FID, and synthesis from enantiomerically pure (S)- and (R)-perillaldehyde. This work demonstrates the value of walkingstick insects as sources of new bioactive compounds and provides an analytical framework for identifying such substances.
Department of Biochemistry and Molecular Biology, University of Florida, Gainesville, Florida 32610, USA.
Aaron T
AT
Dossey
Spencer S
SS
Walse
Oskar V
OV
Conle
Arthur S
AS
Edison
D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D007313:Insecta / Q000737:chemistry* / Q000378:metabolism; D008270:Madagascar; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D039821:Monoterpenes; C523224:parectadial; C033342:perillaldehyde