T. Ando et al., SEX-PHEROMONE OF JAPANESE GIANT LOOPER, ASCOTIS-SELENARIA-CRETACEA - IDENTIFICATION AND FIELD-TESTS, Journal of chemical ecology, 23(10), 1997, pp. 2413-2423
The Japanese giant looper, Ascotis selenaria cretacea, is a serious de
foliator of tea gardens in Japan. GC-MS analysis of the virgin female
extract confirmed the presence of (Z,Z)-6,9-cis-3,4-epoxynonadecadiene
. This compound had attracted male moths in a previous random screenin
g test using C-17-C-23 epoxydienes synthesized in a racemic form. Furt
her GC and HPLC analyses with chiral columns showed that the natural p
heromone was composed of 3S,4R and 3R,4S isomers in a ratio of 53:47,
although the field evaluation revealed stronger activity of the pure 3
R,4S epoxide than of other enantiomeric mixtures. This result indicate
s that the sexual communication system of this Japanese subspecies dif
fers from that of the species in Israel, which is selectively attracte
d to an isomer with the opposite configuration. Interestingly, the 3S,
4R epoxide attracted another geometric male, Alcis angulifera, in our
field tests, (Z,Z,Z)-3,6-9-Nonadecatriene, a parent olefinic compound
of the epoxy pheromone, was also identified in the gland extract of A.
s. cretacea, but its effect on the attractive activity of the epoxide
was not assured in field tests. The amount of the triene increased in
the virgin female during photophase and also after decapitation. The
epoxy component completely disappeared after decapitation, but could b
e increased by an injection of subesophageal ganglion extract. The dat
a suggest that the triene is a biosynthetic precursor of the epoxide a
nd that a neuropeptide hormone (PBAN) regulates the epoxydation.