Comparative Biochemistry and Physiology Part B 132 (2002) 375–380

Phospholipid and triacylglycerol fatty acid composition of major life

stages of sunn pest, Eurygaster integriceps (Heteroptera:
Scutelleridae)
Mehmet Bashana,*, Halit Akbasa, Kadir Yurdakocb
a
Department of Biology, Science and Art Faculty, University of Dicle, 21280 Diyarbakir, Turkey
b
¨ 35160 Izmir, Turkey
Department of Chemistry, Science and Art Faculty, University of Dokuz Eylul,

Received 14 June 2001; received in revised form 25 January 2002; accepted 8 February 2002

Abstract

Phospholipid and triacylglycerol fatty acid compositions of whole animals from all life stages of Eurygaster integriceps,
including eggs, nymphs, pre-diapausing adults and diapausing adults, were determined. The fatty acid composition of
total lipids of their food, wheat, was also determined. The major components of the insects and their food were the
expected C16 and C18 saturated and unsaturated fatty acids. Since fatty acid compositions of third-stadium nymphs
were not similar to the profiles of their food, most likely, dietary fatty acids are modified by the insect. The fact is that
the food does not provide C20 polyunsaturated fatty acids, but the insect tissue lipids include these components. We
suggest biosynthesis of the C20 components by elongationydesaturation of C18:2ny6, an abundant component of the
diets. We also show differences in fatty acid profiles from each of the life stages. 䊚 2002 Elsevier Science Inc. All
rights reserved.

Keywords: Phospholipid; Triacylglycerol; Fatty acid compositions; Sunn pests; Eurygaster integriceps

1. Introduction to lipid storage and mobilization in insects. Also

Understanding fat metabolism in insects increas-
es our knowledge of insect metabolism and
expands our appreciation of the ways in which
different organisms have solved common biochem-
ical problems. In many ways, fat metabolism in
insects is less complex than in vertebrates, so
insects can serve as a viable models system for
understanding fundamental aspects of fat metabo-
lism (Canavoso et al., 2001).
More recently, Arrese et al. (2001) have written
a review about lipid storage and mobilization in
insects. In this review, they have presented a few
of what we consider to be interesting areas related
*Corresponding author.
E-mail address: mbashan@dicle.edu.tr (M. Bashan).
Canavoso et al. (2001) have presented a broad
overview of fat metabolism in insects. They sum-
marize the state of understanding of the require-
ments for the major lipids in the diet and then
describe in detail the insect lipid transport system.
Fatty acids assume broad biological signifi-
cance, with important roles in three general areas.
First, lipid energy reserves, generally stored as
saturated and monounsaturated fatty acids, are
deployed in development, hibernation and loco-
motion. Secondly, fatty acids form essential parts
of the cellular structure as components of cellular
phospholipids (PLs), particularly in biomembra-
nes. Thirdly, certain polyunsaturated fatty acids
(PUFAs), specifically 20:3ny6, 20:4ny6 and
20:5ny3 act in regulatory roles, as substrates for
the biosynthesis of prostaglandins and other eicos-

1096-4959/02/$ - see front matter 䊚 2002 Elsevier Science Inc. All rights reserved.
PII: S 1 0 9 6 - 4 9 5 9 Ž 0 2 . 0 0 0 4 5 - 3
376 M. Bashan et al. / Comparative Biochemistry and Physiology Part B 132 (2002) 375–380
anoids. With respect to insects, studies of the
biology and biochemistry of fatty acids have
revealed completely new insights, such as the de
novo biosynthesis of C18 and C20 PUFAs (Stan-
ley-Samuelson et al., 1988; Stanley, 2000).
Insects have been thought to exhibit a broad
similarity in fatty acid compositions, generally
made up of C16 and C18 saturated, monounsatur-
ated and polyunsaturated components (Fast, 1970;
Thompson, 1973). More recent work, however,
reveals an increasing number of exceptions to the
general pattern. Stanley-Samuelson and Dadd
(1983) postulated that virtually all insects have
C20 PUFAs in their tissue lipids, although these
long-chain components are present in very low
proportions of total fatty acids. Aquatic insects
stand out with very high proportions ()20%) of
20:4ny6 and 20:5ny3 in their tissue lipids (Han-
son et al., 1985). Most dipterans are characterized
by high proportions of 16:1 (Thompson, 1973).
The dipteran pattern of high 16:1 was also seen in
two heteropterans, the chinch bugs Blissus leucop-
terus leucopterus and B. iowensis (Spike et al.,
1991).
We considered the question of whether the
pattern of high 16:1 proportions in chinch bugs
occurs in other heteropterans by determining the
fatty acid compositions in the sunn pest, Eurygas-
ter integriceps, a wide-spread heteropteran pest of
considerable economic impact in Turkey, Russia,
Iraq, Syria, Bulgaria and Iran. Here we report that
E. integriceps is similar to the chinch bug and
dipteran pattern, with high proportions of 16:1.
2. Materials and methods
2.1. Insects
E. integriceps migrate to Karacadag mountain
from Diyarbakir for overwintering. The height of
Karacadag is 1919 m, where conditions are not
humid, and it has a peculiar steppe vegetation.
The insects complete their diapause stage under
plants such as Astragalus spp. and Acantholimon
spp., which are widely distributed in this area.
When the surrounding temperature reaches to 15
8C, they migrate from overwintering localities to
wheat fields around Diyarbakir and cause damage
feeding on wheat throughout the plant’s
development.
Eggs, nymphs and new-generation (pre-dia-
pause) adults of E. integriceps were collected
throughout April and May (1998) from wheat
fields in Diyarbakir, Turkey. Diapausing adults
were collected in January and February (1998)
from fields in Karacadag, Turkey. Whole insects
were used in all analyses.
2.2. Lipid analysis
The insects were processed for lipid extraction
and analysis following the methods described by
Howard and Stanley (1990). Total lipids were
extracted by homogenizing groups of four adult
insects to 20 nymphs per sample in chloroformy
methanol (2:1, vyv; Bligh and Dyer, 1959). Four-
gram samples of fresh wheat grain, the natural
diet, were similarly extracted. Autoxidation of
unsaturated components was minimized by adding
50 ml of 2% butylated hydroxytoluene in chloro-
form to each sample during the extraction process.
The total lipid extracts were dried under a stream
of N2, and PL and triacylglycerol (TG) fractions
were isolated by thin-layer chromatography
(TLC), using Silica Gel G TLC plates (20=20
cm, 0.25-mm thick). After applying the total lipid
extracts, the TLC plates were developed in petro-
leum ether: diethyl etheryacetic acid (80:20:1, vy
v). Lipid fractions were made visible by spraying
the TLC plates with 29,79-dichlorofluorescein
(Supelco, Supelco Park, PA, USA), and PL and
TG fractions were identified by corresponding
standards.
The PL and TG fractions were scraped into
reaction vials, and the associated fatty acids were
transmethylated by refluxing the fractions in acid-
ified methanol for 90 min at 85 8C. The fatty acid
methyl esters (FAMEs) were extracted from the
reaction vials three times with hexane, and
concentrated.
The FAMEs were analyzed on gas chromatog-
raphy using a Ati Unicam 610 gas chromatograph
equipped with a SP-2330 capillary column (0.25
mm=30 M, 0.2 mm film thickness, Supelco), a
flame ionization detector and an Unicam 4815
recording integrator. The separations were con-
ducted with temperature programming from 180
to 200 8C at 5 8Cymin, after an initial 2-min hold.
FAMEs were identified by comparisons of reten-
tion times with authentic standards (Sigma Chem-
ical Co., St. Louis, MO, USA).
Statistical analysis included ANOVA to deter-
mine variability, F-tests to identify treatment
effects, and least significant difference and stu-
 M. Bashan et al. / Comparative Biochemistry and Physiology Part B 132 (2002) 375–380 377

Table 1
Fatty acid compositions, as proportions of total fatty acids, in phospholipids prepared from total lipid extracts of whole Eurygaster
integriceps at the indicated life stages*

Fatty acid Egg Nymph NGA male NGA female Diapausing male Diapausing female
(ns5) (ns5) (ns5) (ns5) (ns5) (ns5)
14:0** 1.67 (0.10) a 3.97 (0.21) b 0.19 (0.07) c 0.37 (0.12) d 2.74 (0.17) a 0.92 (0.14) e
15:0 0.81 (0.21) a 0.80 (0.06) a 0.76 (0.19) a 0.52 (0.18) b 0.82 (0.10) a 0.44 (0.13) b
16:0 14.36 (0.32) a 19.87 (0.22) b 12.63 (0.54) a 11.64 (0.52) a 17.19 (0.53) b 25.17 (0.50) c
16:1 12.39 (0.29) a 9.40 (0.22) b 10.80 (0.27) b 10.27 (0.49) b 13.16 (0.42) a 16.93 (0.48) c
17:0 0.98 (0.08) a 1.09 (0.08) a 1.10 (0.10) a 1.21 (0.09) a 0.74 (0.08) b 0.55 (0.16) b
18:0 13.76 (0.30) a 12.10 (0.55) a 10.59 (0.31) b 10.10 (0.28) b 10.36 (0.29) b 8.46 (0.37) c
18:1 19.26 (0.40) a 19.36 (0.42) a 25.39 (0.50) b 25.51 (0.52) b 29.50 (0.63) c 35.90 (0.49) d
18:2 34.83 (0.62) a 29.42 (0.58) b 33.72 (0.61) a 36.25 (0.64) a 20.84 (0.51) c 9.68 (0.32) d
18:3ny6 0.17 (0.04) a 0.66 (0.05) b 0.45 (0.13) c 0.32 (0.10) c 0.52 (0.14) c 0.23 (0.07) a
18:3ny3 1.73 (0.11) a 2.51 (0.15) b 1.80 (0.09) a 1.60 (0.07) a 1.99 (0.08) a 0.40 (0.09) c
20:1ny9 – 0.69 (0.07) a 1.45 (0.06) b 1.11 (0.04) b 1.03 (0.05) b 0.29 (0.10) c
20:2ny6 – 0.24 (0.07) a 0.24 (0.08) a 0.38 (0.08) b 0.19 (0.04) a 0.21 (0.08) a
20:3ny6 – 0.23 (0.08) a 0.18 (0.05) a 0.13 (0.04) b 0.21 (0.02) a 0.24 (0.04) a
20:4ny6 – 0.17 (0.05) a 0.16 (0.06) a 0.12 (0.03) b 0.18 (0.03) a 0.15 (0.05) a
20:5ny3 – 0.58 (0.19) a 0.52 (0.18) a 0.43 (0.15) a 0.53 (0.06) a 0.52 (0.11) a
Values are mean (standard deviation).
*
Abbrevations: NGAsNew-generation adult; nsnumber of individual analyses.
**
Means followed by the same letter are not significantly different (P)0.05).

dent’s t-tests to identify significant differences
between groups.
3. Results
3.1. Fatty acid composition: influence of life stage
and gender
The fatty acid compositions of PLs and TGs
prepared from eggs, nymphs, pre-diapause adults
and diapause adults are given in Tables 1 and 2.
While the usual fatty acid components are present
in all stages, we draw attention to 16:1, which
made up 9–17% of PL fatty acids and 16–25%
of TG fatty acids. Aside from 16:1, 16:0, 18:0,
18:1 and 18:2ny6 were major components of the
PL and TG fractions. Low proportions of eicosa-
noid precursor C20 PUFAs were present in all
samples except the eggs.
3.2. Fatty acid profiles of nymphs and their diet
(wheat)
The fatty acid compositions of PLs and TGs
prepared from whole third-stadium larvae, and the
total fatty acid composition of wheat on which the
nymphs were fed, are presented in Table 3. The
major components in wheat include 12:0, 14:0,
16:0, 16:1, 18:0, 18:1, 18:2ny6 and 18:3ny3. We
note important differences between insect fatty
acid profiles and their dietary profiles. In particu-
lar, the wheat had higher proportions of 18:3ny3
(13 vs. 3%), but lower proportions of 18:2ny6
compared to PLs (17 vs. 32%).
We also note evidence for biosynthesis of C20
PUFAs from their dietary C18 counterparts. The
PL fatty acids of the nymphs included 20:2ny6,
20:3ny6, 20:4ny6 and 20:5ny3, which are char-
acteristically absent from plant lipids.
4. Discussion
The major PL and TG fatty acid components
prepared from all life stages of E. integriceps
include the usual 16:0, 16:1, 18:0, 18:1 and
18:2ny6, which have been recorded from virtually
all insect tissue lipid studies (Fast, 1970). The E.
integriceps fatty acid profiles stand out from the
general insect patterns with high proportions of
16:1, as seen in many dipterans (Thompson,
1973), and three other heteropterans, two chinch
bug species (Spike et al., 1991), and a closely
related sunn pest, E. maura (Kilincer et al., 1987).
However, other heteropterans do not express the
unusual pattern of high 16:1 proportions (Fast,
1970; Thompson, 1973). Hence, we recognize a
group of insects, all characterized by high propor-
tions of 16:1.
Although it remains difficult to assign a biolog-
ical significance to the 16:1, we may speculate on
378 M. Bashan et al. / Comparative Biochemistry and Physiology Part B 132 (2002) 375–380

Table 2
Fatty acid compositions, as proportions of total fatty acids, in triacylglycerols prepared from total lipid extracts of whole Eurygaster
integriceps at the indicated life stages*

Fatty acid Egg Nymph NGA male NGA female Diapausing male Diapausing female
(ns5) (ns5) (ns5) (ns5) (ns5) (ns5)
12:0** 5.66 (0.24) a 2.64 (0.17) b 1.12 (0.10) c 1.06 (0.08) c 1.38 (0.09) c 1.16 (0.09) c
14:0 14.64 (0.53) a 12.76 (0.59) a 3.09 (0.17) b 2.28 (0.15) b 3.33 (0.23) b 3.25 (0.26) b
15:0 0.31 (0.09) a 0.20 (0.03) a 0.63 (0.09) b 0.71 (0.07) b 0.31 (0.07) a 0.23 (0.06) a
16:0 16.13 (0.33) a 23.50 (0.38) b 23.68 (0.24) b 22.07 (0.23) b 26.87 (0.19) b 23.80 (0.43) b
16:1 16.21 (0.32) a 21.54 (0.37) b 25.27 (0.20) b 22.88 (0.22) b 23.06 (0.21) b 23.99 (0.38) b
17:0 1.16 (0.07) a 1.13 (0.09) a 1.21 (0.13) a 1.16 (0.09) a 0.43 (0.07) b 0.32 (0.07) b
18:0 3.80 (0.17) a 6.07 (0.17) b 3.08 (0.18) a 5.32 (0.16) b 4.26 (0.24) a 5.86 (0.28) b
18:1 30.94 (0.56) a 15.79 (0.39) b 25.69 (0.62) c 29.58 (0.53) a 31.36 (0.73) a 30.68 (0.62) a
18:2 8.97 (0.23) a 11.22 (0.53) b 14.65 (0.26) c 12.28 (0.23) b 7.63 (0.20) d 9.09 (0.39) a
18:3ny6 0.22 (0.06) a 0.69 (0.04) b 0.52 (0.18) b 0.41 (0.19) c – –
18:3ny3 1.23 (0.12) a 1.56 (0.12) a 0.66 (0.09) b 1.73 (0.29) a 0.82 (0.11) b 1.04 (0.22) a
20:1ny9 0.73 (0.06) a 2.88 (0.16) b 0.42 (0.05) c 0.52 (0.21) c 0.53 (0.08) c 0.62 (0.20) a
Values are mean (standard deviation).
*
Abbrevations: NGAsNew-generation adult; nsnumber of individual analyses.
**
Means followed by the same letter are not significantly different (P)0.05).

its presence in the lipids of a few species. Many
insect pheromones are derived from fatty acids
(Stanley-Samuelson et al., 1988), and the high
proportions of 16:1 in some species may represent
a substrate for pheromone biosynthesis. Analysis
of sunn pest and chinch bug pheromones can
illuminate this possibility.
We note the presence of odd-chain fatty acids
in our analyses. These components are rarely
recorded in studies of insect tissue fatty acids.
Odd-chain fatty acids are reported for PLs from
the mealworm beetle, Tenebrio molitor (Howard
and Stanley, 1990), from the cicada Tibicen deal-
batus (Stanley-Samuelson et al., 1990) and from
the chinch bugs mentioned earlier (Spike et al.,
1991). We conclude that odd-chain fatty acids are
fairly common components of insect lipids, the
meaning of which is still not understood.

Table 3
Proportions of fatty acids, as percentage of total fatty acids, in the phospholipid and triacylglycerol fractions of total lipid extracts from
third instar nymphs of Eurygaster integriceps and their respective nymphal diets

Fatty acid Phospholipid Triacylglycerol Nymphal diet total

(ns5) (ns5) fatty acids
(ns5)
12: 0* – 2.14 (0.18) a 8.61 (0.51) b
14: 0 4.02 (0.23) a 15.66 (0.52) b 9.39 (0.55) c
15: 0 0.62 (0.08) a 0.21 (0.07) b –
16: 0 18.48 (0.35) a 23.82 (0.49) b 22.65 (0.56) b
16: 1 7.58 (0.21) a 20.63 (0.45) b 5.31 (0.24) c
17: 0 1.20 (0.08) a 1.28 (0.08) a –
18: 0 14.08 (0.51) a 5.46 (0.23) b 11.90 (0.53) a
18: 1 17.62 (0.35) a 16.82 (0.32) a 12.05 (0.54) b
18: 2ny6 31.95 (0.59) a 10.03 (0.46) b 16.87 (0.49) c
18: 3ny6 0.73 (0.07) a 0.53 (0.11) b –
18: 3ny3 3.56 (0.19) a 2.72 (0.15) a 13.20 (0.45) b
20: 1ny9 1.02 (0.05) a 0.73 (0.09) b –
20: 2ny6 0.19 (0.04) a – –
20: 3ny6 0.13 (0.03) a – –
20: 4ny6 0.18 (0.05) a – –
20: 5ny3 0.43 (0.10) a – –
Values are mean (standard deviation). n: number of individual analyses.
*
Means followed by the same letter are not significantly different (P)0.05).
 M. Bashan et al. / Comparative Biochemistry and Physiology Part B 132 (2002) 375–380
Our analyses of the PL fractions reveal the
presence of low proportions of C20 PUFAs. This
is an emerging pattern in insect fatty acid studies,
in which C20 PUFAs seem to make up very low
proportions of the tissue lipids of terrestrial insects.
Especially low proportions were recorded in stud-
ies of house flies, Musca domestica (Wakayama
et al., 1985), mealworm beetles, T. molitor, and
two species of cicada, T. dealbatus (Stanley-
Samuelson et al., 1990) and Magicicada septen-
decim (Hoback et al., 1999). These findings
support our view that virtually all insects include
C20 PUFAs in their lipids, albeit in very low
proportions.
With respect to herbivorous insects, the low
proportions of C20 PUFAs in insect tissue lipids
also provide evidence that insects are able to
biosynthesize C20 PUFAs from their C18 counter-
parts. Biosynthesis of C20 PUFAs is thought to
proceed through a series of elongation and desa-
turation reactions. For example, 18:2ny6 might
be desaturated to 18:3ny6, then elongated to
20:3ny6 and finally desaturated to 20:4ny6. Such
pathways were first investigated in the cricket
Teleogryllus commodus, using radioactive 18:2ny
6 as substrate (Stanley-Samuelson and Loher,
1983; Jurenka et al., 1988). Similar approaches
showed that several species are competent to
synthesize C20 PUFAs, including the waxmoth,
Galleria mellonella (Stanley-Samuelson and Dadd,
1984) and the cockroach, Periplaneta americana
(Jurenka et al., 1987). Beyond these direct studies,
analyses of insect tissue lipids and their corre-
sponding diets have provided substantial evidence
for the elongationydesaturation pathways in other
species, including the gypsy moth, Lymantria dis-
par (Stanley-Samuelson et al., 1992). Stanley
(2000) proposed these pathways for all insects.
The data reported here for E. integriceps support
this view. As expected from plant lipid biochem-
istry, the wheat diets of these insects do not provide
C20 PUFAs (Harwood and Russell, 1984). We
infer that the C20 components recorded in analysis
of the sunn pest are synthesized from 18:2ny6.
The biological significance of C20 PUFAs, par-
ticularly in terrestrial insects where these compo-
nents occur in very low proportions, is related to
the biosynthesis of prostaglandins and other eicos-
anoids. The roles of eicosanoids in the biology of
insects and other invertebrates are gaining increas-
ing attention (Stanley, 2000). So far, eicosanoid
actions in insect immunity, reproduction, and Mal-
379
pighian tubule physiology have been documented
(Stanley, 2000). We anticipate the discovery of
additional eicosanoid actions in insects, all of
which draws increased attention to the presence
and metabolism of C20 PUFAs.
Dietary fatty acids are converted to stored TAG
in the fat body, an analogous to vertebrate adipose
tissue and liver, and then mobilized to support
metabolic needs (Canavoso et al., 2001; Arrese et
al., 2001). New-generation adults of sunn pest
feed on wheat and store lipids in spring. During
the diapause period, these lipid stores are used to
support the energy demands of insects that hiber-
nate. A comparison of the fatty acid composition
of the wheat and the insect indicates that E.
integriceps alter the composition of fatty acids in
the natural food by biosynthesis. E. integriceps
characteristically have high proportions of 16:1.
This characteristic feature of E. integriceps fatty
acid profiles is not substantially modified by
wheat, natural food of insect. We think that this
component is probably synthesized from palmitic
acid by desaturation of the ny9 carbon.
Insects can also modify their fatty acid compo-
sition in response to changes in environmental
conditions. For example, the fatty acid composi-
tions of the southwestern cornborer, Diatrea gran-
diosella and the silk worm, Bombyx mori (Azuma
et al., 1989; Shimizu, 1992) changed with the
onset of diapause. Here, we note differences in
fatty acid compositions of pre-diapause and dia-
pause sunn pests. In particular, diapausing adults
had lower proportions of 18:2ny6, their major
PUFA. These results are in agreement with those
found for another heteropteran, Pyrrhocoris apte-
rus (Hodkova´ et al., 1999). We speculate that
these changes represent metabolic adaptation to
the colder temperatures of winter. Although the
point has not been investigated in detail for E.
integriceps, many ectothermic organisms respond
to seasonal changes in environmental temperatures
by modifying the fatty acid compositions of struc-
tural lipids, particularly PLs, that make up cell
membranes (Hazel, 1995).
Acknowledgments
This study was supported by TUBITAK (The
Scientific and Technical Research Council of Tur-
key). This is project number TBAG-1651. We
thank Dr David W. Stanley (University of Nebras-
ka–Lincoln) for his help with this project.
380 M. Bashan et al. / Comparative Biochemistry and Physiology Part B 132 (2002) 375–380
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