Chemical identification of defensive secretion of stick insect,Megacrania tsudai Shiraki

Abstract

Volatile constituents of the defensive secretion of the stick insect,Megacrania tsudai Shiraki, in Taiwan have been analyzed by gas chromatography-mass spectrometry (GC-MS). In addition to the major component, actinidine, three more minor components of the secretion are identified as boschniakine and two stereoisomers of 1-acetyl-3-methylcyclopentane by comparing GC retention times with the authentic samples and synthetic compounds. Other components are also tentatively assigned as derivatives of actinidine.

Alkaloids in Animals

“…Actinidine (20) also found in some beetles (see above) is the major volatile constituent of the defensive secretion of a stick insect, Megacrania tsudai (Phasmida) from Taiwan (Ho and Chow, 1993). Mature males of the locust Schistocerca gregaria (Orthoptera, Acrididae) secrete as a volatile il Lpyrroline responsible for the maturation-accelerating effect observed in the males of their species.…”

Defensive Spiroketals from Asceles glaber (Phasmatodea): Absolute Configuration and Effects on Ants and Mosquitoes

“…However, many species produce a chemical spray from a pair of tegumental glands in their prothorax when disturbed (Bedford 1978; Dossey 2010; Dossey 2011; Scudder 1876) (and references therein). The chemical composition of defensive sprays from only a few species has been analyzed (Bouchard et al 1997; Chow and Lin 1986; Dossey 2011; Dossey et al 2009; Dossey et al 2007; Dossey et al 2006; Eisner et al 1997; Ho and Chow 1993; Meinwald et al 1962; Prescott et al 2009; Schmeda-Hirschmann 2006; Schneider 1934; Smith et al 1979). Besides the various secondary metabolites, glucose has been reported in the defensive sprays of A. buprestoides ,(Dossey et al 2006), P. schultei (Dossey et al 2006), P. mocquerysi (Dossey et al 2007), P. westwoodii (Dossey et al 2009) and M. nigrosulfurea (Prescott et al 2009).…”

Alkyldimethylpyrazines in the Defensive Spray of Phyllium westwoodii: A First for Order Phasmatodea

“…However, the chemical composition of defensive sprays from only a few species has been analyzed to date (Bouchard et al 1997; Chow and Lin 1986; Dossey et al 2007; Dossey et al 2006; Eisner et al 1997; Eisner 1965; Ho and Chow 1993; Meinwald et al 1962; Schmeda-Hirschmann 2006; Schneider 1934; Smith et al 1979). The first analysis of a phasmid defensive spray was published in 1934 on Agathemera crassa (Schneider 1934) (referred to by Schneider as Paradoxomorpha crassa ).…”

“…A. buprestoides produces at least three stereoisomers of a monoterpene first identified by Meinwald et al in 1962 and named anisomorphal (Meinwald et al 1962). Since then, other phasmids have been shown to produce monoterpenes such as: iridodoal ( Graeffea crouani ) (Smith et al 1979), nepetalactone ( Graeffea crouani ) (Smith et al 1979), actinidine ( Megacrania alpheus (Chow and Lin 1986) and Megacrania tsudai (Ho and Chow 1993)), limonene ( Sipyloidea sipylus ) (Bouchard et al 1997), parectadial (a novel monoterpene first identified from the phasmid Parectatosoma mocquerysi (Dossey et al 2007)), dolichodial (isomer of anisomorphal found in young A. buprestoides (Dossey et al 2008)), peruphasmal (isomer of anisomorphal from Peruphasma schultei ) (Dossey et al 2006), and others as minor components (Bouchard et al 1997; Ho and Chow 1993). In addition to monoterpenes, 4-methyl-1-hepten-3-one (as mentioned above) (Schmeda-Hirschmann 2006) and quinoline (from Oreophoetes peruana ) (Eisner et al 1997) have also been found in phasmid insect defense gland sprays.…”