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Identification of methyl farnesoate from in vitro culture of the retrocerebral complex of adult females of the moth Heliothis virescens LepidopteraNoctuidae and its conversion to juvenile hormone III.

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Teal and Proveaux
Archives of Insect Biochemistry and Physiology 61:98–105 (2006)
Identification of Methyl Farnesoate From In Vitro
Culture of the Retrocerebral Complex of Adult Females
of the Moth, Heliothis virescens (Lepidoptera: Noctuidae)
and Its Conversion to Juvenile Hormone III
P.E.A. Teal* and A.T. Proveaux
Gas chromatographic-mass spectral analysis of extracts obtained from in vitro culture of isolated retrocerebral complexes
obtained from adult females of the moth Heliothis virescens resulted in identification of methyl farnesoate as well as juvenile
hormone III (JH III) but not JH III acid. Inhibition of JH biosynthesis by incubation of tissue in synthetic Manduca sexta
allatostatin (Manse-AST, p Glu-Val-Arg-Phe-Arg-Gln-Cys-Tyr-Phe-Asn-Pro-Ile-Ser-Cys-Phe-COOH) reduced production of these
chemicals to negligible levels. However, incubation of tissue in the presence of Manse-AST plus farnesol resulted in production
of significant amounts of both methyl farnesoate and JH III. Tissue incubated in the presence of Manse-AST plus methyl
farnesoate produced only JH III. The results indicated that methyl farnesoate is naturally produced by the corpora allata of
adult females of Heliothis virescens÷ However, tissue incubated in the presence of Manse-AST plus JH III acid also produced JH
III in amounts equivalent to that produced by tissue incubated with methyl farnesoate. Thus, both methyl farnesoate and JH III
acid could serve as a precursor for biosynthesis of JH III. Arch. Insect Biochem. Physiol. 61:98–105, 2006.
Wiley-Liss, Inc.
Published 2006
KEYWORDS : juvenile hormone biosynthesis; methyl farnesoate; Lepidoptera
coordination of reproductive competence with
sexual behavior in female moths.
All insects produce the JH homolog methyl
Juvenile hormones (JH) are required for vitel-
logenesis in adult female Lepidoptera (Cusson et
al., 1994; Satyanarayana et al., 1992; Zeng et al.,
dienoate (JH III). Biosynthesis of the sesquiterpene
1997). Consequently, female reproductive compe-
skeleton of JH III has been studied in detail and is
tence depends on production of JH. Indeed, among
apparently common to all insects (see Schooley
some species, pheromone biosynthesis, mating,
and Baker, 1985, and references therein). Interest-
and ovarian development are delayed until critical
ingly, Lepidoptera are unique in that they also syn-
levels of JH are produced (Cusson et al., 1994;
thesize other homologs of JH formed by variable
Gadenne, 1993; Picimbon et al., 1994). Thus, JH
substitution of the methyl moieties at positions 3,
acts as one of the critical hormones regulating the
7, and/or 11 of the carbon skeleton with ethyl
Center for Medical, Agricultural and Veterinary Entomology, USDA-ARS, Gainesville, Florida
Use of a trade, firm, or corporation name in this publication is for information and convenience of the reader. Such use does not constitute official endorsement or
approval by the United States Department of Agriculture or the Agriculture Research Service of any product or service to the exclusion of others that may be
*Correspondence to: Peter E.A . Teal, CMAVE-USDA-ARS, 1700 SW 23 DR., PO BOX 14565, Gainesville, FL, 32604. E-mail: [email protected]
Received 30 June 2005; Accepted 20 August 2005
Published 2006 Wiley-Liss, Inc.
This article is a US Government work and, as such, is in the public domain in the United States of America.
DOI: 10.1002/arch.20104
Published online in Wiley InterScience (
Archives of Insect Biochemistry and Physiology
February 2006
doi: 10.1002/arch.
Production of Methyl Farnesoate by Moths
groups. The most common of these higher forms
following reports the identification of MF from ex-
tracts of incubations of isolated CA-CC complexes
3,7,11-trimethyl-2,6-tridecadienoate (JH II) and
and adult females of the tobacco budworm moth,
(2 E ,6 E ,10 cis )-(10 R ,11 S )-10,11-epoxy-7-
Heliothis virescens and the conversion of MF to JH
of JH, methyl (2
ethyl-3,11-dimethyl-2,6-tridecadienoate (JH I) are
III by the retrocerebral complexes (RCs).
produced by adult female Lepidoptera (Baker et
al., 1985; Edwards et al., 1995; Lessman et al.,
1989; Roller et al., 1967, Shu et al., 1997).
The terminal steps in JH biosynthesis, which result in epoxidization and esterification of the acid
analogs, are well documented in Orthoptera and
Dictyoptera (Schooley and Baker, 1985, and references therein). In these orders, farnesoic acid is first
acted upon by methyl transferase in the presence
of S-adenosyl-methionine (SAM) to form methyl
farnesoate (MF), which is then acted upon by an
epoxidase in the presence of O2 to form JH III.
These terminal steps are less well understood in
Lepidoptera. Studies using homogenates of the corpora cardiaca (CC)-corpora allata (CA) from adult
females of the tobacco hornworm moth, Manduca
sexta, showed that MF was formed when homogenates were incubated with farnesoic acid in the
absence of NADPH (Reibstein et al., 1976). However, when NADPH was included no detectable
amounts of MF were found, instead JH III was produced (Reibstein et al., 1976). Indeed, when tissue homogenates were incubated with labeled MF
plus NADPH no label was incorporated into JH
III. These results suggest strongly that epoxidation
of farnesoic acid, homofarnesoate, and dihomofarnesoate precedes esterification in Lepidoptera.
However, liquid chromatographic analysis of extracts from in vitro incubations of isolated CA from
adult females of Pseudaletia unipuncta resulted in
recovery of a radiolabeled product(s) that eluted
prior to that of MF (Cusson et al., 1991). These
authors suggested that the unidentified labeled
product(s) were methyl homofarnesoate (MHF)
Capillary GC\GC-MS grade ethyl acetate, hexane, and methanol were from Burdick and Jackson and 18 megohm water was obtained from a
Milli Q UVplus® water purification system. Tissue
culture medium 199 containing Hank’s salts and
glutamine was obtained from Gibco (Gaithersburg,
MD). Manse-AST was custom synthesized at the
Interdisciplinary Center for Biotechnology Research, Protein Core Facility (University of Florida).
The peptide was purified by reversed phase liquid
chromatography as described elsewhere (Abernathy
et al., 1996) and assessed to be ~97% pure by analytical reversed phase liquid chromatography, mass
spectroscopy, and amino acid analysis.
acetate (farnesyl acetate, FA) and (E,E)-farnesol
were purchased from Aldrich (Milwaukee, WI).
Synthetic JH I, II, and III were gifts from D. A.
Schooley (University of Nevada, Reno, NV) and
MF was a gift from S. Tobe (University of Toronto,
Toronto, ON). These synthetics were purified by
liquid chromatography using a Rheodyne 7125®
injector, a Kratos Spectraflow 400® pump, and a
Waters 410® differential refractometer using an
Adsorbosil® silica column (250
4.6 mm, 5-
particles) eluted with 5% ethyl acetate in hexane
(flow = 1.5 ml/min). Mass spectral analysis of purified sesquiterpenes indicated that all were at least
98% pure and that MF and FA did not contain any
and methyl dihomofarnesoate (MDHF), the non-
of the JH homologs. JH III acid was synthesized
epoxidized methyl ester analogs of JH II and JH I,
by saponification of JH III. JH III, dissolved in
which are the major JH homologs produced by
methanol, was added drop-wise to an equal vol-
these female moths. If this were so, then Lepidoptera
ume of 2M KOH and the mixture was stirred over-
could employ MF, MDHF, and MHF as precursors
night at 25 C. The reaction mixture was neutralized
for the epoxidase and, thus, JH biosynthesis could
with 1M HCl and extracted with hexane. The aque-
proceed as in the Orthoptera and Dictyoptera. The
ous phase, containing JH III acid, was applied to a
Archives of Insect Biochemistry and Physiology
February 2006
doi: 10.1002/arch.
Teal and Proveaux
solid phase extraction column (Alltech C18 Extract-
to minimize tissue damage. In some studies, RCs
Clean™, 500 mg packing) that had been precondi-
were placed in 30
2% Ficoll 400, 72 mg/ml CaCl2, and 0.6 mM so-
followed by 8 ml of water. After application of the
dium acetate and 0.6 mM sodium propionate with
JH III acid extract, the column was washed with 4
or without 10 nM Manse-AST in a conical amber
ml of water and the JH III acid eluted with 1 ml of
vial (Teal, 2001). In other studies, some RCs were
60% acetonitrile in water. The JH III acid fraction
incubated for 24 h in media containing 10 nM
was diluted with an equal volume of water and
Manse-AST and 0.1
further purified by liquid chromatography under
acid. In these cases, farnesol or JH III acid was first
gradient conditions using an Adsorbosil® C18 col-
dissolved in a solution of medium 199 containing
umn (250
4.6 mm, 5-
of medium 199 containing
mM of either farnesol or JH III
particles) and detec-
10% acetone and appropriate amounts of this so-
tion with a Kratos Spectra Flow 757® variable
lution were added to the incubation medium prior
wavelength detector set at 210 nm. The column was
to adding tissues. Tissue was incubated at 25 C in
eluted using a linear gradient of 30% acetonitrile
the dark on a rotary shaker (80 rpm) for 24 h.
to 70% acetonitrile in water over 40 min at 1 ml/
Incubations were stopped by the addition of 50
min using a Kratos Spectra Flow 430® gradient
each of first methanol and then hexane contain-
former. Under these conditions, JH III acid eluted
ing 10 pg/
at 24 min and JH III at 33 min. The fraction con-
vortexed at 3,200 rpm for 2 min, centrifuged at
taining JH III acid was diluted by addition of an
equal volume of water and extracted with an equal
organic layer removed. The aqueous layer was ex-
volume of hexane, to remove any residual apolar
tracted two additional times with 50
contaminants, prior to extraction three times with
The organic fractions were combined in a clean
equal volumes of dichloromethane to extract the
vial and concentrated under N2 to approximately
JH III acid. Analysis of the dichloromethane frac-
ml FA as internal standard. Samples were
for 5 min, to break the emulsion, and the
ml of hexane.
ml prior to mass spectral analysis.
tion by GC-Mass spectroscopy indicated that the
To determine if JH III acid was produced by tis-
acid was free of JH III. An aliquot of the acid was
sue incubated with FOH, we incubated and extracted
dissolved in methanol and derivatized to the me-
tissues as above. However, we reserved the metha-
thyl ester by addition of six times the volume of
nol/water extract, which would contain the JH III
hexanes containing 2M trimethylsilyldiazomethane
acid, and diluted it by addition of 100
(Aldrich) and stirring for 1 h. Analysis of the
This was then subjected to reversed phase liquid
derivatized sample indicated that 98 % had been
chromatography using a YMC™ ODS-AQ column
esterified to JH III.
150 mm, 3-
ml of water.
particles). The column was
eluted using a linear gradient from 20–70% methanol in water over 40 min at a flow rate of 200
min. We collected the fraction corresponding to the
Female TBW moths were obtained as pupae
elution volume of JH III acid and subjected this to
from North Carolina State University. Adults, trans-
esterification with trimethylsilyldiazomethane. The
ferred to cages upon eclosion and before the wings
esterified sample was analyzed by GC-MS for the
had expanded, were provided with a 5% sucrose
presence of JH III.
solution soaked onto commercial cotton balls and
held under a normal photoperiod of 12:12 (L:D)
h at 26
Mass Spectral Analysis
± 2°C and 60 ± 5% relative humidity until
use. The RCs, containing the CA-CC, of females
Extracts of incubations of RCs were analyzed
were dissected from the head under tissue culture
by chemical ionization mass spectroscopy (MS)
medium 199. No attempt was made to separate
using a Finnigan-Matt ITS 40® ion trap mass spec-
the corpora allata from the corpora cardiaca so as
trometer (MS) interfaced to a Varian Star 3400®
Archives of Insect Biochemistry and Physiology
February 2006
doi: 10.1002/arch.
Production of Methyl Farnesoate by Moths
gas chromatograph having a cool-on-column injector as described elsewhere (Teal et al., 2000).
The analytical column, a 30 m
0.25 mm (id)
mm film thickness) (J&W) was interfaced to a 10 m ´ 0.25 mm (id) uncoated, de-
Description of Cleavage Assignments Resulting in Generation
of Diagnostic Ions Used for Quantitation of MF When Analyzed by
Chemical Ionization Mass Spectroscopy Using and Ion Trap Mass
DB5-MS® (0.1
activated fused silica retention gap, and a 10 cm
0.5 mm (id) length of uncoated, deactivated
fused silica in the injector. Conditions of chro-
Ion no.
Ion description
Mass to
Ion 1 – CH 3OH (from ester)
Ion 2 – CO (from ester)
C 10H17 O2 (ester portion after scission
matography were: initial injector temperature =
Ion 4 – CH 3OH
C 9H13 (common terpene fragment)
at 170 C/min to 270 C; initial column tempera-
Ion 5 – CO
ture = 40 C for 5 min; column temperature in-
creased at 5 C/min to 210 C; He carrier gas linear
flow velocity = 24 cm/sec; GC-MS transfer line
between C7 and C8)
40 C for 30 sec; injector temperature increased
Mean ion intensity as a percentage of the base peak (n = 5 replicates at 50 pg/
Base peak.
temperature = 230 C. Under these conditions,
farnesyl acetate eluted at 32.3, JH III at 33.8, JH
II at 35.4, and JH I at 37.3 min, respectively. The
MS was operated in the chemical ionization (CI)
In an earlier work (Teal et al., 2001), we identi-
mode using isobutane as reagent gas (mass ac-
fied JH I, II, and III from extracts of incubations
quisition range = 60–350 amu; scan rate = 1 sec).
of the RC from female TBWs and employed both
Identification of JH homologs was based on com-
Manse-AST and allatotropin (Manduca sexta form)
parison of fragmentation patterns (60–300 amu)
and retention indexes of compounds eluting during analysis of natural product samples with those
of synthetic standards. Quantification of amounts
of JH III and MF was based on ion intensities of
six diagnostic ions for each compound (JH III m/e = 235, 217, 189, 147, 125, 111) and was accomplished as described by Teal et al. (2000). For
MF, we used the following ions: m/e 251 = M+1;
m/e 219 = M+1-CH3OH (ester); m/e 191 = M+1CH3OH-CO (ester); m/e 169 = scission between
C7 and C8 yielding C10H17O2 (ester end of molecule); m/e 137 = scission between C7 and C8
to study the biosynthesis of JH in 3-day-old females. In the present study, we assessed initially
the capacity of isolated CA-CC complexes from 0-,
1-, and 2-day-old TBW females to produce JH III
in the presence or absence of Manse-AST. Very little
JH III was produced by retrocerebral complexes
from 0-day-old females and incubation of tissue
from females of this age in Manse-AST had no effect on JH III production relative to controls (Fig.
1). However, incubation of CA-CC complexes from
Manse-AST resulted in significant inhibition of JH
III production compared to controls in which no
Manse-AST was added to the incubation medium
yielding C 10H 17O2 - CH3OH (ester); m/e 109 =
(Fig. 1). The amount of JH III produced by tissue
scission between C7 and C8 yielding C10H17O2 -
from 2-day-old females incubated in Manse-AST
CH3OH - CO (ester) (Table 1). These ions plus
was about fourfold lower than the controls. How-
m/e = 121 (C9H13), a common fragment ion for
ever, 43-fold less JH III was produced by tissues
terpenes, have been described from analysis of
from 1-day-old females incubated in Manse-AST
electron impact spectra (Liedtke and Djerassi,
with respect to controls. In fact, the amount of JH
1972) although the intensities of the fragments
III produced by tissue from 1-day-old females in-
found in our studies were different because we
cubated in Manse-AST was no different from that
used chemical ionization and an ion trap ms
produced by day-0 females. Rescue studies by
rather than double-focusing and quadrupole in-
Kramer et al. (1991) on Manduca sexta and Teal
struments used by Liedtke and Djerassi (1972).
(2001) on TBW provided strong evidence that
Archives of Insect Biochemistry and Physiology
February 2006
doi: 10.1002/arch.
Teal and Proveaux
In addition to JH III, we also found another
compound in all extracts from tissue incubated
with FOH. This compound was not present in extracts from control tissues incubated in Manse-AST
alone and had a chromatographic retention index
and mass spectrum identical to synthetic MF (Fig.
2). Amounts of JH III and MF from extracts of tissues incubated in Masne-AST plus FOH are shown
in Figure 3. To determine if MF was produced without addition of precursor (FOH) or Manse-AST to
the medium, we incubated RC complexes from 2day-old females in just medium 199 for 24 h. Ex-
Fig. 1.
Comparison of mean amounts (
tracts of these tissues were found to contain MF
present in extracts obtained from cultures of RCs of 0-, 1-,
and 2-day-old females incubated in the presence or absence of Manse-AST. Means capped by the same letters
(Fig. 4) although the amounts were very small
compared to those of JH III. Nonetheless, the data
proved conclusively that MF was naturally pro-
are not significantly different in a Fisher’s Least Significant Difference test (
P = 0.05) (n = 5/treatment).
Manse-AST acts prior to formation of FOH because
in both studies the inhibitory effects of Manse-AST
on JH biosynthesis could be overcome by addition
of exogenous FOH to the incubation medium. Additionally, studies have provided evidence that
Manse-AST acts after the production of acetyl- and
propionyl-CoA (Teal et al., 2001). Thus, it may be
that the difference in amounts of JH III synthesized
by tissues from 1- and 2-day-old females incubated
in Manse-AST reflects differences in the amount of
stored precursors like mevalonate or isopentenyl
pyrophosphate required for production of FOH.
We chose to use 1-day-old females for studies in
which we tracked the fate of exogenous precursors
of JH III because tissue from these females was capable of de novo synthesis of JH III in the absence
of Manse-AST but could be significantly inhibited
from producing significant amounts of JH III by addition of Manse-AST to the incubation medium. Extraction of RC complexes and media from 1-day-old
females incubated in the presence of Manse-AST
plus FOH resulted in recovery of significantly more
JH III (28.9
1.2 fmol/h, n = 5) than was recov-
Fig. 2.
Comparison of chemical ionization mass spectra
(isobutane reagent gas) of naturally produced (upper spectrum) and synthetic (lower spectrum) methyl farnesoate.
ered from extracts of control preparations in which
Diagnostic ions used for identification and quantification
only Manse-AST was added to the medium (mean
are shown above ions of interest and fragments yielding
= 4.7
± 1.1 fmol/h, n = 5; t = 3.29, 8 df).
the ions are given in Table 1.
Archives of Insect Biochemistry and Physiology
February 2006
doi: 10.1002/arch.
Production of Methyl Farnesoate by Moths
cubated tissue from 1-day-old females in the presence of Manse-AST plus MF. This resulted in production of significant amounts of JH III but no
farnesal nor FOH was identified (Fig. 5). Interestingly, performing the same experiment but substituting JH III acid for MF resulted in a similar increase
in JH III production relative to controls (Fig. 5)
and no MF was found in these samples. These results suggest strongly that the methyl transferase
involved in the esterification step in JH III biosynthesis has no specificity for either farnesoic acid
or JH III acid, although it apparently does have
Fig. 3.
Comparison of mean amounts (
specificity for the sesquiterpene acid analogs of the
of methyl
farnesoate and JH III produced by RCs from 1-day-old
females incubated with Manse-AST plus farnesol (n = 6
JH homologs (Reibstein et al., 1976).
To determine if JH acid was produced in detectable amounts, we incubated glands in Manse-AST
plus FOH as usual but we reserved the methanolic
extract that would contain JH III acid. The diluted
duced by the corporal allata of females incubated
methanolic extract was then chromatographed us-
in culture medium. The production of MF by
ing a narrow bore reversed phase LC column and
homogenates of the CA complexes from adult fe-
the fraction corresponding to JH acid was collected
males of the tobacco hornworm moth has been
and derivatized to JH III with trimethylsylil diazo-
documented (Reibstein et al., 1976). However, no
methane. Mass spectral analysis of this fraction
measurable JH III was found when [ H]-MF was
did not result in our detection of JH III although
incubated in Graces medium with 5 mM NADPH
we injected amounts equivalent to 350–500 h of
plus the homogenate (Reibstein et al., 1976). To
determine if MF was converted to JH III by iso-
Our results show conclusively that MF is pro-
lated, but otherwise intact, RC complexes, we in-
Fig. 5.
±SE) of JH III pro-
Comparison of mean amounts (
duced by RC’s of 1-day-old females incubated in the presFig. 4.
Comparison of mean amounts (
of methyl
ence of only Manse-AST or Manse-AST + FOH or Manse-AST
farnesoate and JH III extracted from incubations of RCs
+ MF or Manse-AST + JH III acid. Means capped by the
of 2-day-old females incubated in only culture medium
same letter are not different in a Fisher’s Least Significant
(n = 6 replicates).
Difference test (
Archives of Insect Biochemistry and Physiology
P = 0.05) (n = 6 replicates per treatment).
February 2006
doi: 10.1002/arch.
Teal and Proveaux
duced during the conversion of FOH to JH III by
application of a pseudopeptide mimic of a pheromon-
isolated RCs of adult female TBW moths. Addition-
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bations suggests that the acid is not produced by
these females. It is possible that epoxidization of
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incubations in which we saturated the system with
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heliothis, complex, virescens, identification, farnesoate, retrocerebral, iii, vitro, adults, methyl, moth, lepidopteranoctuidae, female, culture, juvenile, hormone, conversion
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