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.
Dossey
Aaron T
AT
Department of Biochemistry and Molecular Biology, University of Florida, Gainesville, Florida 32610, USA.
Walse
Spencer S
SS
Conle
Oskar V
OV
Edison
Arthur S
AS
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