Journal of Chemical Ecology, Vol. 15, No. 1, 1989

CHEMICAL COMPOSITION AND FUNCTION OF METAPLEURAL GLAND SECRETION OF THE ANT, Crematogaster deformis SMITH (HYMENOPTERA: MYRMICINAE) l

A.B.

ATTYGALLE, H.J.

2 B. S I E G E L , 2 O . V O S T R O W S K Y ,

BESTMANN,

2 and U. MASCHWITZ

2

3

2hlstitute for Organic Chemistry University of Erlangen-Narnberg Henkestrasse 42, D-8520, Erlangen, F.R.G. 3blstitute for Zoology University of Frankfurt Siesmayerstrasse 70, D-6000, Frankfurt, F.R.G. (Received August 18, 1987; accepted November 25, 1987)

Abstract--The secretion of the hypertrophied metapleural gland of the ant Crematogaster deformis contains a mixture of phenols, consisting mainly of 3-propylphenol, 3-pentylphenol, 3,4-dihydro-8-hydroxy-3-methylisocoumatin (mellein), 5-propylresorcinol, and 5-pentylresorcinol. The secretion is released, as a repellent, when the highly vulnerable petiolar-postpetiolar region of the abdomen is attacked by enemy ants. In addition, small amounts of the secretion are released regularly to serve as an antiseptic, which is considered the original function of the gland. The secretion also has some insecticidal properties. Key Words--Crematogaster deformis, Hymenoptera, Myrmicinae, ant, defensive allomone, repellent, metapleural gland, 3-propylphenoi, 3-pentylphenol, 3,4-dihydro-8-hydroxy-3-methylisocoumarin, mellein, 5-propylresorcinol, 5-pentylresorcinol.

Presented at the Fourth Annual Meeting of the International Society of Chemical Ecology, July 13-17, 1987, Hull, England.

317 0098-0331/89/0100-0317$06.00/0 © 1989PlenumPublishingCorporation

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ATTYGALLEET AL. INTRODUCTION

The exocrine glands of ants are known to produce a remarkable variety of compounds, and extensive investigations have been carded out on their glandular chemistry (Attygalle and Morgan, 1984). However, the metapleural glands located in the thorax, although found in most ants, have received little attention. In the few species that have been studied, only carboxylic acids have been identified. Some of these acids show antibiotic properties (Maschwitz et al., 1970; Schildknecht and Koob, 1970, 1971). Crematogaster deformis possesses a relatively enlarged metapleural gland, similar to other species of Crematogaster belonging to the subgenus Physocrema. It had been indicated that the secretions of this gland are used to repel enemies (Maschwitz, 1974). Here, we describe in detail the chemical composition and function of the glandular secretion. For the first time, a unique mixture of phenols, hitherto not described from any arthropod source, has been found.

METHODS AND MATERIALS

Sources of bisect Materials. A large colony of C. deformis was dwelling in an inaccessible hole in a tree near the Gombak Valley Field Study Centre of the University of Malaya. A few artificial feeding sites made of honey-water mixtures were provided nearby. Polymorphic workers, which were day-active, were attracted in great numbers within a short time to these sites. The ants were caught, kept in moistened plastic containers, and observed from time to time for 10 days. When the ants were loosely held by the thorax region, with a pair of forceps, they released their metapleural gland secretion. These droplets were withdrawn by glass capillaries (Morgan and Tyler, 1977) and sealed in larger capillaries for later examinations. A colony of C. scutellaris was collected in southern France. Its secretions were isolated and sealed in the same way as described for C. deformis. Gas Chromatography (GC). Gas chromatography was carried out on a Hewlett-Packard 5890 instrument fitted with a 25-m x 0.22-mm fused-silica capillary column coated with SE-54. The oven was held at 60°C for 2 min and programmed at 6°C/min to 260°C. Further analysis was performed on a United Technologies-Packard 438A instrument equipped with a 25-m x 0.22-mm fused-silica column coated with SP-2340. The oven was kept at 60°C for 4 min and increased at 4°C/min to 195°C. The samples dissolved in hexane were chromatographed by splitless injection. Micropreparative gas chromatography was performed on a Hewlett-Packard 5750 instrument fitted with a 2-m x 4-mm glass column packed with 4%

METAPLEURAL GLAND SECRETION

319

OV-17 on 80-100 mesh Gas Chrom Q. The effluent was split 99:1 (trap-FID) by an all-glass splitter (Baker et al., 1976). The glandular secretion, dissolved in CS2, was injected and the effluent volumes corresponding to each major component were trapped in metal U-tubes cooled in Dry Ice. The material trapped was washed directly with CDCI 3 (400/zl) into NMR sample tubes (5 mm) and 400 MHz FT-NMR spectra were measured by a JEOL JNM GX-400 instrument. Gas Chromatography-Mass Spectrometry (GC-MS). The identification of the major components was achieved by GC-MS. A Finnigan 9502 gas chromatograph, fitted with a Grob-type split-splitless injector, linked to a Finnigan 3200E quadrupole mass spectrometer with a Data System 6000 was used. A fused-silica capillary column (SE-54, 25 m x 0.22 mm) was directly coupled to the mass spectrometer. The carrier gas was helium at 1 ml/min. The oven was held at room temperature for 4 min and programmed at 6°C/min to 260°C. Acetylation of Extract. The metapleural gland extract in hexane (5/~I) was mixed with an ethereal solution (5/zl) containing 5 % acetic anhydride and 5 % pyridine. The mixture was left overnight and examined by GC and GC-MS. Chemicals. 5-Propylresorcinol was kindly provided by Prof. Ayer (University of Alberta). Small samples of mellein were sent by Prof. Moil (University of Tokyo) and Dr. Brophy (University of New South Wales). 5Pentylresorcinol (olivetol) was purchased from Aldrich Chemicals. 3-Propylphenol (peak 1) was synthesized by a Wittig reaction of ethylidenetriphenylphosphorane with 3-methoxybenzaldehyde. The 3-(l-propenyl)anisole thus obtained [yield 79%, bp 120-130°C/15 torr, kugelrohr (128129°C/20 torr, Hudson and Robinson, 1941)] was hydrogenated to 3-propylanisole [yield 68%, bp 110-120°C/20 torr, kugelrohr (92°C/11 tort, Parkes, 1948)] using 5% Pd/C as catalyst, and the latter was hydrolyzed with acetic acid-HBr to give 3-propylphenol, peak 1 [yield 15%, bp 80-90°C/20 torr, kugelrohr (100-102°C/6-7 torr, Hartung and Crossley, 1934), mass and [IH]NMR spectra in Table I]. 3-Pentylphenol (peak 2) was synthesized by a similar procedure, using butylidenetriphenylphosphorane for carbonyl olefination. The 3-(1-pentenyl)anisole formed [yield 84%, bp 73-76°C/0.01 torr (92-99°C/1 torr, Alles et al., 1942)] was hydrogenated to 3-pentylanisole [yield 92 %, bp 70-72°C/0.05 torr (97-98°C/3 torr, Alles et al., 1942)] and subsequently hydrolyzed to 3pentylphenol (peak 2) [yield 82%, bp 69-72°C/0.05 torr (99-100°C/1 torr, Alles et al., 1942), mass and [~H]NMR spectra in Table 1]. Behavioral Studies. In order to study the attacking behavior of C. deformis, a worker of Oecophylla smaragdina was placed in an assembly of C. deformis at a honey-water feeding site. Similarly, the defence behavior was studied by placing a C. deformis ant at an assembly of O. smaragdina. The latter species was selected as the test ant species because it occupies the same habitat

3-Pentylphenol

Mellein

5-Propylresorcinol

5-Pentylresorcinol

2

3

4

5

180(M ÷, 22), 138(11), 137(11), 125(6), 124(100), 123(28), 69(9), 67(7)

178(M +, I00), 160(43), 149(17), 135(17), 134(88), t33(12), 132(19), 121(5), 106(22), 105(15), 104(22), 78(20), 77(16), 51(12) 152(M+, 49), 137(14), 124(100), 123(51), 67(18), 69(20)

164(M +, 17), 121(13), 108(100), 107(68), 106(16), 91(9), 77(29)

136(M +, 30), 135(8), I08(50), I07(I00), 106(29), 94(6), 91(8), 77(39)

Natural product

194(M +, 0), 152(97), 137(12), 123(37), 124(80), 51(22), 43(100) 264(M ÷, 4), 222(17), 180(95), 138(36), 137(17), 124(100), 123(68), 43(91)

206(M ÷. 3), 164(24), 122(9), 121(12), 108(100), 107(59), 91(10), 77(31), 43(45) 220(M +, 0), 178(86), 160(49), 149(13), 134(100), 133(27), 106(20), 105(27), 104(25), 78(33), 77(48), 51(43), 43(92)

178(M +, 7), 137(7), 136(74), 121(17), 108(68), 107(100), 106(24), 94(7). 91(13), 77(35), 43(50)

Acetylated product

0.87 (3H, t, J = 7.0 Hz), 2.47 (2H, t, J = 7.8 Hz), 5.20 (IH, broad s), 6.17 (IH, t, J = 2.3 Hz), 6.25 (2H, d, J = 2.2 Hz)

c

1.51 (3H, d, J = 6.4 Hz), 2.91 (2H, d, J = 7.0 Hz), 4.72 (IH, 6 lines), 6.66 (1H, d, J = 0.9 Hz), 6.68 (IH, d, J = 0.9 Hz), 7.39 (IH, t), I1.01 (1H, s)

c

0.93 (3H, t. J = 7.3 Hz), 2.53 (2H, t, J = 7.4 Hz), 4.90 (IH, s), 6.63 (IH, d, J = 8.0 Hz), 6.64 (1H, s), 6.75 (IH, d, J = 7.6 Hz), 7.14 (IH, I, 7.6 Hz)

NMR h [8]

"The peak numbers refer to Figure 1. All the compounds identified showed identical retention times to those given by authentic samples, on SE-54 and SP-2340 columns. h400 MHz FT-NMR spectra were recorded using about 10 to 20-~g samples. Signals not given were masked by impurity peaks. "Material available was insufficient for a satisfactory NMR spectrum.

3-Propylphenol

Identification

1

Peak"

Mass spectral data m/z (%)

TABLE I. CHEMICAL COMPOSITION OF METAPLEURAL GLAND SECRETION OF C. deformis: SUMMARY OF ANALYTICAL EVIDENCE FOR STRUCTURE ASSIGNMENT

c)

)-

O

321

METAPLEURAL GLAND SECRETION

and is considered an important competitor of C. deformis. The repellent effect of the metapleural gland secretion was studied by offering isolated thoraces of C. deformis, or chopped grasshopper parts smeared with one gland-equivalent of the secretion, to an assembly of O. smaragdina at a feeding site. The behavior of the ants was observed for 20 rain after placing each lure. Similarly, grasshopper parts smeared with 1 izl of 3-pentylphenol, or honey-water containing 1, 0.1, 0.01, or 0% 3-pentylphenol, were offered to colonies of O. smaragdina and Pheidole sp. Likewise, 2 gland-equivalents of the secretion were applied to individual mealworm larvae (Tenebrio molitor), which were offered to an European pied flycatcher (Ficedula hypoclea). In order to study the toxic effects of the secretion, either 1 gland-equivalent of the metapleural gland secretion or 1 ~1 of 3-pentylphenol was applied, by a glass capillary, onto the gaster or head of O. smaragdina workers. Thirty ants were subjected to each treatment and observed for 20 hr. The release of alarm behavior was investigated by presenting crashed body parts, such as a head, excised mandibular glands, thorax, or gaster, on a piece of filter paper, near a feeding site of C. deformis. The ants were observed for 1 min after each stimulus was presented. The experiment was repeated six times for each stimulus.

RESULTS

Release of Glandular Secretions. The workers of C. deformis, which were kept in closed containers, released small quantities of their metapleural gland secretion even when they were not being disturbed. The secretion is released from the orifices of the reservoirs, which have no closing mechanism. The presence of the secretion could be recognized by its characteristic tarlike smell, when the lid of the container was opened. When an ant was loosely held, with a pair of forceps, by its antenna, leg, or head, sometimes the release of minute quantities of the metapleural secretion could be observed. However, when the ant was gripped directly by the thorax, or gaster, a large colorless or somewhat violet droplet appeared at the gland orifice. Due to the lipophilic nature of the secretion, it soon spread over the cuticle around the orifice. When the ants were treated more roughly, seized by the head or legs, they released their very sticky brownish-red-colored Dufour gland contents and tried to smear the secretion on the pair of forceps by which they were held. Chemical Analysis of Secretion. The metapleural gland secretion withdrawn into glass capillaries had a strong phenolic smell. The analysis of the extract by gas chromatography revealed the presence of five major components (Figure 1). The highly polar nature of these components was evident from the

322

ATTYGALLE ET AL.

OH OH Ho~Pen

OH [~Pen

OH

HO~PP

\ J o

1'2

min

2~

3;

FIG. 1. Volatiles in the metapleural gland secretion of C. deformis. Chromatogram obtained on a 25-m x 0.22-mm fused-silica capillary column coated with SE-54. Oven temperature was held at 60°C for 2 min and programmed at 6°C/min to 260°C. The sample in hexane was introduced by splitless injection. Peak numbers refer to those in Table 1.

large shifts in retention times observed when a chromatogram obtained on a nonpolar column (SE-54) was compared to one on a polar column (SP-2340). All five components showed much longer retention times on the polar column. Complete mass spectra were obtained by GC-MS for all components, and satisfactory N M R spectra were recorded for the three major compounds. The results are summarized in Table 1. In order to verify the presence o f phenols, the mixture was acetylated. Components 1, 2, 4, and 5 underwent complete acetylation, and new peaks corresponding to the products appeared in the chromatogram. The peak 3 was only partially acetylated under the conditions used. The GC-MS analysis of the acetylated mixture showed that components 1, 2, and 3 were monoacetylated, while 4 and 5 were diacetylated. The degree o f change in the retention times also indicated this. The mass spectrum of peak 2 was identical to that known for 3-pentyl-

M E T A P L E U R A L G L A N D SECRETION

323

phenol (Gorfinkel et al., 1969). Both 2- and 4-pentylphenols have the base peak at m/z 107; only the 3-pentylphenol shows the base peak at m/z 108. Although the spectrum of peak 1 was very similar to those from 2-propylphenol and 4propylphenol (Stenhagen et al., 1974), there were significant differences. For example, the spectrum of peak 1 has a significant peak at m/z 121 (13%) which is absent in those of 2- and 4-propylphenots. Also, the peak at m/z 108 is more prominent in the natural product (50%) than those of 2- and 4-isomers (less than 8%). It appeared that such a prominent even-mass ion at m/z 108 can arise only from a 3-isomer. The pentyl and higher derivatives studied by Gorfinkel et al. (1969) show a similar behavior. In fact, if the alkyl group is pentyl or larger, the m/z 108 peak becomes the base peak. The NMR spectrum (Table 1) could establish that the peak 1 is a n-propyl compound and not an isopropyl derivative. 3-Propylphenol was synthesized, and it was chromatographically and spectroscopically identical to the natural product. Peak 3 could be identified immediately by its mass spectrum, which was congruent with that known for 3,4-dihydro-8-hydroxy-3-methylisocoumarin (mellein) (Brand et al., 1973). The mass and NMR spectra (Table 1) and the retention time of an authentic sample were identical to those from the natural compound. To be consistent with mass spectroscopic and acetylation results, peak 5 must be a pentylresorcinol. According to the deductions of Occolowitz (1964), only the 1,3,5-isomer of such a compound can yield an even-mass ion at m/z 124. The properties of an authentic sample of 5-pentylresorcinol matched well with those of the natural product. By analogy, peak 4 was suspected to be 5propylresorcinol, which was later proved correct by comparison with an authentic sample. The absolute amount of the phenols present per ant varied widely from 2 to 20/zg per sample. Although the relative amounts of compounds also showed a broad variation, the chromatogram shown in Figure 1 can be considered typical. The mixture of phenols found seems characteristic to the species C. deformis. For example, such phenols were not detected in the metapleural glands of C. scutellaris or C. borneensis (Attygalle, Fiala, and Maschwitz, unpublished observations). Defensive and Attacking Behavior. The attacking behavior of C. deformis could be studied by introducing an alien ant, such as O. smaragdina or Diacamma rugosa, into a large assembly of C. deformis workers at a feeding site. The workers attacked the alien instantly and bit into its body appendages. Spread-eagled by this attack, the alien was unable to move, and in this posture it was dragged along the recruitment trail. The use of metapleural or Dufour g!and secretions was not observed during these attacks. On the other hand, when a worker of C. deformis was placed in an assembly of O. smaragdina, it

324

ATTYGALLE ET AL.

too was attacked immediately, either by biting into the body appendages or the body itself. When two or more workers of O. smaragdina got hold of the appendages, they pulled and spread-eagled the C. deformis worker, immobilizing it in such a way that it was unable to use its defensive glands. Subsequently, it was killed slowly by other ants that reinforced the attack. However, if the attackers initially bit into the head or neck region, C. deformis could bend its highly mobile gaster tip forward and smear the attacker with sticky Dufour gland secretion. In 10 of 15 such attacks observed, the contaminated O. smaragdina worker stopped the attack and began to clean itself. On the contrary, if the attackers first bit into the posterior thorax, the coxae, the petiolar region, or the proximal gaster region, C. deformis released, in defense, its metapleural gland secretions. This immediately stopped the attack. In 18 of 20 cases observed, the contaminated O. smaragdina workers immediately started an intensive and prolonged cleaning process. They wiped their heads on the ground and cleaned their mouth-parts with their legs. The strong repellent effect of the metapleural gland secretion was also evident when we placed isolated thoraces of C. deformis, or chopped grasshopper parts, smeared with the secretion, at a feeding site of O. smaragdina. While the uncontaminated parts were carried away instantly at the first contact, no objects smelling of the metapleural secretion were taken. Similar results were obtained with grasshopper parts contaminated with 3-pentylphenol. Likewise, honey-water containing 1 or 0.1% 3-pentylphenol was refused by Pheidole sp., while untreated solutions were consumed by hundreds of ants. However, a 0.01% solution was also accepted. O. smaragdina refused even the uncontaminated solutions. Moreover, the secretion did not manifest any repellent effect when contaminated mealworm larvae were offered to a European pied flycatcher. The bird consumed six mealworms, one after the other, without any hesitation. Besides the repellent effects, the secretion also shows some toxicity to insects. Table 2 shows the results obtained by treating workers of O. smaragdina with the secretion of C. deformis or 3-pentylphenol. TABLE 2. MORTALITY CAUSED BY METAPLEURALGLAND SECRETION AND 3-PENTYLPHENOL a

Number of dead ants counted after treating with Part of O. smaragdina subjected to treatment Head Gaster

1 Metapleural gland equivalent of C. deformis.

1 t~l of 3-pentylphenol

Control (water)

16 6

8 30

0 0

"30 Workersof O. smaragdinawere subjected to each treatment and observed for 20 hr.

325

METAPLEURAL GLAND SECRETION

TABLE 3. ALARM BEHAVIOR RELEASED IN ITS WORKERS BY CRUSHED BODY PARTS OF

C. deformis ~ Crushed body part presented

Total number of ants showing alarm behavior'

Head

2 Excised mandibular glands

Thorax

252

230

24

Gaster 27

Controlh 23

"The ants were observed for 1 rain, after presenting each stimulus on a piece of filter paper to an assembly of C. deformis workers near a feeding site. bA piece of filter paper. "The total number, after repeating each presentation six times. Although the metapleural secretion has repellent and some toxic effects towards insects, it has no alarm pheromone properties. Alarm behavior (i.e., fast movements, attraction, opening of the mandibles, and biting behavior) was exclusively released by the mandibular gland secretion (Table 3). DISCUSSION The metapleural glands are found in most ants. As far as is known from the few species that have been analyzed, the glandular secretion contains certain carboxylic acids that show antibiotic and antiseptic properties. These acids are supposed to act as topical antiseptics that suppress the growth of fungi and bacteria on the body surface of the adults and brood, and on the nest material (Maschwitz et al., 1970; Maschwitz, 1974; Schildknecht and Koob, 1971; Hrlldobler and Engel-Siegel, 1984). C. deformis regularly releases small amounts of its phenolic metapleural gland secretion to maintain its body and nest hygiene. The bactericidal effect of phenols is well known. The presence of an alkyl chain tends to increase lipid solubility, and from the investigations conducted by Ayer et al. (1983), it is clear that the bactericidal activity increases, up to a certain point, as the length of the side chain increases. Phenols, very similar to those found in the gland are often used in proprietory antiseptics. The phenolic compounds, except mellein, identified in C. deformis, have been reported from biological sources only on rare occasions. 3-Propylphenol is an attractant for tsetse flies and has been isolated in the urine of the host buffalo (Hassanali et al., 1986). It is also found in tobacco smoke (Arrendale, 1984). 3-Propylresorcinol has been found in a lichen (Chamy et al., 1985), and it has been claimed to be present in oakmoss extracts (Gavin and Tabacchi,

326

ATTYGALLE ET AL.

1975); however, the published mass spectrum does not correspond to ours obtained from an authentic sample. Long-chain alkyl phenols and resorcinols are characteristic of the oils of Anacardiaceae (Bestmann et al., 1987; Skopp et al., 1987; Occolowitz, 1964). The only similar compound known from ants is 5-methylresorcinol (orcinol) (Blum et al., 1982a) Mellein is a fairly ubiquitous compound with antibiotic properties. It was first found as a fungal metabolite (Ayer and Shewchuk, 1986, and references therein), and later its presence was shown in ants (Brand et al., 1973; Brophy et al., 1981; Bellas and H611dobler, 1985), termites (Blum et al., 1982b), and moths (Baker et al., 1981; Nishida et al., 1982; Kunesch et al., 1987). Producing an antibiotic secretion may be the sole primary function of the metapleural gland secretion in ants having a "normal-sized" gland; however, at least in those species possessing a hypertrophied (exceptionally enlarged) gland, additional functions can be expected. C. deformis has such an enlarged gland, and this hypertrophic development is accompanied by chemical specialization. None of the phenols found in this unique mixture, except mellein, has been previously isolated from any arthropod source. From our observations it is clear that C. deformis uses this secretion also as a defensive allomone. In fact, this secondary function is the more important role of the secretion. The strong-smelling secretion has a powerful repellent, and even toxic, effect against enemy ants. The slender petiolar-postpetiolar region of C. deformis is highly vulnerable to enemy attacks of biting. The metapleural secretion exclusively provides the chemical defense of this region. The head-neck region, body appendages, and gaster tip of the workers are protected by the defensive secretions from the hypertrophied Dufour gland. This secretion can be applied, at the aforementioned body regions, employing the gaster, which is highly mobile. A highly mobile gaster is a characteristic feature of the genus Crematogaster. Thus, C. deformis is protected by a two-gland chemical defense system, which has, however, not taken over the alarm function. The alarm pheromone is produced in the mandibular gland. In contrast, in C. (Physocrema) inflata, it is produced in the metapleural gland (Maschwitz, 1974). The injecting part of the sting of C. deformis is atrophied, similar to those in other species of Crema-

togaster. It appears that a change has occurred, during phyletic development, from a more primitive system of injecting the hydrophilic venom from the poison gland, to a more advanced defense system using surface-active lipophilic secretions of the Dufour gland. The lipophilic and highly sticky Dufour gland secretion can entangle the enemy. The metapleural secretion is repellent, or sometimes even lethal, to the enemy. Such " n e w " chemical weapons employing surface-active aUomones are common in higher Formicidae (Buschinger and Maschwitz, 1986). Although venom gland secretions of ants are often potent toxicants, the injection of the venom into the body of the enemy, ant is very

327

METAPLEURAL GLAND SECRETION

difficult, if not impossible, especially w h e n the opponent is highly mobile, small, or mass-attacking. For fighting against such an e n e m y , an instantly applicable repellent or a sticky fluid, such as those utilized by C. deformis, is much more effective. F u r t h e r m o r e , the petiolar region o f m y r m i c i n e and some other ants are usually protected against biting ants by small but sharp epinotal spines. These spines, found in most other Crematogaster species, are lacking in C. deformis because the petiolar region is well-protected by the metapleural gland secretion. A similar d e v e l o p m e n t can be seen in C. inflata. It also lacks epinotal spines and produces a sticky gluelike defensive secretion in its enormously enlarged metapleural gland (Maschwitz, 1974). The genus Crematogaster demonstrates an astonishing variety in its defensive chemistry and biology and will be the subject of further investigations. Acknowledgments--We thank Prof. K. Moil. (University of Tokyo), Prof. W.A. Ayer (University of Alberta), and Dr. J.J. Brophy (University of New South Wales) for small samples of chemicals. We also thank Dr. W. Bauer and R. Waibel for their help in obtaining spectra. The financial support of the Deutsche Forschungsgemeinschaft is gratefully acknowledged.

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Chemical composition and function of metapleural gland secretion of the ant,Crematogaster deformis smith (hymenoptera: Myrmicinae).

The secretion of the hypertrophied metapleural gland of the antCrematogaster deformis contains a mixture of phenols, consisting mainly of 3-propylphen...
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