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Bombykal a Second Pheromone Component of the Silkworm Moth Bombyx mori L.

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Bombykal, a Second Pheromone Component of the
Silkworm Moth Bombyx mori L.
By Gerhard Kasang, Karl Ernst Kaissling, Otto Vostrowsky,
and Hans Jurgen Bestmann[*l
Dedicated to Professor AdoY Butenandt on the occasion of
his 75th birthday
In 1959 Butenandt et al. reported the isolation and elucidation of the structure of the first insect sex attractant[']. The
compound concerned was (E)-1O,(Z)-12-hexadecadien-l-ol
(bombykol), which is secreted from the abdominal glands
(sacculi laterales) of the female silkworm moth Bombyx mori
L. and serves as an attractant only to the male members
of the same species. It has hitherto been assumed that
bombykol was the only pheromone that played a role in
the chemical communication system between the different
sexes of the species Bombyx mori['I.
Electrophysiological assay of single cells of the olfactory
hairs of the male animals showed, however, that only one
of the two morphologically different receptor
was responsive to bombykol, whereas the female's scent excited both
This pointed to the presence of a second pheromone
component. It was then found that the cell type not excited
by bombykol was respon~ive[~l
to (El-1O,(Z)-12-hexadecadien1-a1 (b~mbykal)[~l,
a compound recently synthesized in our
laboratories. This finding prompted us to search for signs
of the presence of bombykal in the glands of the female
animal of Bombyx mori[6J.We have now succeeded in demonstrating the presence of bombykal in extracts from the abdominal glands of female silk worm moths which were bred
in Taiwan and Italy.
The abdominal tips excised from 460 freshly emerged female
silkworm moths were together extracted with benzene. The
concentrated extract was purified and separated by preparative
thin-layer chromatography on silica gel. The zones corresponding to bombykal and bombykol (Rf=0.53 and 0.29, hexane/ethyl methyl ketone = 80: 20) were
and eluted
with chloroform/ethanol (99 :1). The fractions thus obtained
were evaporated to dryness, dissolved in heptane (30 pl), and
gas chromatographically analyzed (4 m stainless steel column
'/s" ID, 3 % SE-30 on chromosorb W-AW-DMCS 80/100
mesh, 200"C, isothermal). The results are shown in Table
1.
Table 1. Content of bombykal and bombyk01[~'in the extract from 460
abdominal tips excised from female silkworm moths[91.
Compound
Bombykal
Bombykol
Retention
time
[min]
Total
amount
Content per
gland
Proportion
[%I
lngl
[%I
5.6
6.8
7
90
15.2
195.7
7.2
92.8
The retention times of the natural bombykal and bombykol
were identical with those of the synthetic compounds['~.The
GC analyses of the two fractions were repeated on a 50 m
thin-film glass capillary (0.32mm ID, OV 101) coupled to
a mass spectrometer["] (70eV, EI spectrum, 2.5 s/scan). The
retention times of natural and synthetic bombykal and bom-
[*I Prof. Dr. H. J. Bestmann, Dr. 0. Vostrowsky
lnstitut f i r Organische Chemie der Universitat Erlangen-Niirnberg
Henkestr. 42, D-8520 Erlangen (Germany)
Dr. G. Kasang, Dr. K. E. Kaissling
Max-Planck-Institut fur Verhaltensphysiologie
D-8131 Seewiesen iiber Starnberg (Germany)
60
bykol were once again identical (co-chromatography), being
19.90 and 22.30 min, respectively (splitless injection, 5 min
25 "C, 80 to 220°C, 8"/min). The mass spectrum of the fraction
with t ~ 19.90min
=
was identical with the spectrum of synthetic
bombykal [m/e=236 (M+, 6%), 235 (M+-H, 2%), 192
(M+-CH3CH0, 0.9%), 67 (100%) and 44 (CH3CHO+,
30 %)I.
The fact that bombykal is present in the abdominal glands
of the female Bombyx mori and that the antennae of the
male have specific and highly-sensitive receptor cells for this
compound proves that bombykal is a second pheromone component of the silkworm moth. At the same time it shows
that also Bombyx mori, the classical "pet" of pheromone
research[', "1, uses a multicomponent system for communication between the sexes, as has been found to be the case
for numerous other species of Lepidoptera[''! The ratio of
the components of such a pheromone complex is decisive
for its mode of action and species ~pecificity~'~!
Received: October 11, 1977 [Z 879 IE]
revised: November 30, 1977
German version: Angew. Chem. 90,74 (1978)
CAS Registry number:
Bombykal, 63024-98-6
[l] A. Butenandt, R. Beckman, D. Stamm, E. Hecker, 2. Naturforsch. 814,
283 (1959).
121 Cf. also F. Anders, E. Bayer, Biol. Zentralbl. 78, 584 (1959).
131 R. A. Steinbrecht, Z. Zellforsch. 139, 533 (1973).
141 K. E. Kaissling, H. J . Bestmann, G . Kassang, 0.Vostrowsky, Nature,
in press.
[5] H . J. Bestmann, 0. Vostrowsky, H . Paulus, ii! Bilfmann, W Stransky,
Tetrahedron Lett. 1977, 121.
[6] Bombykal has also been found to be a possible intermediate in the
enzymic inactivation of bombykol on the male antennae: G. Kasang,
Int. Congr. Biochem., Hamburg, July 25-31, 1976.
171 G . Kasang, G . Gofdner, N . Weiss, J. Chromatogr. 59, 393 (1971).
[8] For the electrophysiologically determined content of bombykol in the
scent glands cf. R . A . Steinbrecht, Vergl. Physiol. 48, 341 (1964).
191 Due to losses during extraction and purification, which amounted to
about 50 % in the case of bombykal, we can not rule out the presence
of very small amounts of other stereoisomers of the aldehyde in the
scent glands.
[lo] Finnigan 3200E Quadrupole Mass Spectrometer with Finnigan 6000
Data System.
[ l l ] D. Schneider, J. Insect Physiol. 8, 15 (1962).
[12] M . Siluerstein in M . Beroza: Pest Management with Insect Sex Attractants, ACS Symp. Ser. No. 23. American Chemical Society, Washington
1970.
[13] H . J. Bestmann, Conference of the Dtsch. Ges. Fettwissenschaft, Wiirzburg, September 20-23,1977.-Cf.
also the results of field experiments
with mixtures of (Z)- and (E)-alkenol acetates and with alkenols and
alkenals: 3. A. Klun, 0 . L. Chapman, K . C. Mattes, P . ii! Wojtkowski,
M . Beroza, P . E. Sonnet, Science 181, 661 (1973); A. K . Minks, S .
Voerman, Entomol. Exp. Appl. 16, 541 (1973); C. R. Gentry, M . Beroza,
J . L. Blythe, B. A . Bierl, J. Econ. Entomol. 67, 607 (1974); C. J. Sanders,
Environ. Entomol. 5 , 868 (1976).
Triptycenophanes-Synthesis via "Double Nonbenzylic
Sulfone Pyrolysis""1
By Fritz Vogtle and Philippe Koo Tze Mew"]
The tricyclic molecular skeleton ( 1 ), called "paddlane"[21,
has been the object of numerous synthetic studies which have
been partly successful in only isolated cases ( 2 ) , (3), (4)12a-c1.
[*] Prof. Dr. F. Vogtle, Dip].-Chem. P. Koo Tze Mew
Institut fur Organische Chemie und Biochemie der Universitat
Gerhard-Domagk-Strasse 1, D-5300 Bonn (Germany)
Angew. Chem. lnt. Ed. Engl. 17 (1978) No. 1
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