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Identification of an Alarm Pheromone in the Ant Crematogaster peringueyi
Abstract
Chemical alarm communication commonly occurs among the social Hymenoptera, particularly among the more highly organized species in which the number of workers per colony is large (Maschwitz 1964). Several of the pheromones concerned with this alarm communication have been chemically identified, but the number identified is small compared with the large number of social Hymenoptera in which they must occur, even after allowance is made for an evident lack of specificity between related species. We report the identification of octan-3-one as the major component of an alarm pheromone complex from the heads of Crematogaster peringueyi Emery. This ketone has not previously been identified as an alarm pheromone in any species of social insect.
... When crushed heads of C mimosae or. C negriceps were presented to either species on the tree, the ants displayed alarm behavior like thai described for C peringueyi (Crewe et al. 1969). No response was obtained when other body parts were used. ...
... Comparably, also octan-3-one has been reported from the secretions of various insects, in particular from the mandibular glands of myrmicine ants (e.g., Crewe et al 1969). ...
While considerable knowledge on the chemistry of the scent gland secretions from the opilionid suborders Laniatores and Cyphophthalmi has been compiled, it is the Palpatores (Eupnoi and Dyspnoi) where chemical data are scarce. In particular, the Dyspnoi have remained nearly unstudied, mainly due to their reported general reluctance to release secretions as well as to the phenomenon of production of insoluble-and inaccessible-solid secretion. We here show that at least certain nemastomatid Dyspnoi, namely all three species of genus Carinostoma, indeed produce a volatile secretion, comprising octan-3-one, 6-methyl-5-hepten-2-one and acetophenone in species-specific combinations. In all Carinostoma spp., these volatiles are embedded in a semi-volatile, naphthoquinone matrix (mainly 1,4-naphthoquinone and 6-methyl-1,4-naphthoquinone). In detail, acetophenone and traces of naphthoquinones characterize the secretions of Carinostoma carinatum. A mixture of octan-3-one, 6-methyl-5-hepten-2-one and large amounts of naphthoquinones were found in C. elegans, and 6-methyl-5-hepten-2-one together with small amounts of naphthoquinones in the secretions of C. ornatum. So far, exclusively naphthoquinones had been reported from a single dyspnoan hitherto studied, Paranemastoma quadripunctatum.
Possible pheromonal components identified from the sting apparatus, mandibular gland and Nasonov gland of worker honeybees (Apis mellifera) were tested in an attempt to elucidate their function. Other chemicals known to affect behaviour were also tested. The components iso-pentyl acetate and n-octyl acetate from the sting, and 2-heptanone from the mandibular glands, repelled bees and diminished Nasonov gland exposure (scenting); 1-pentanol and (Z)-11-eicosen-1-ol from the sting diminished scenting; iso-pentyl acetate, n-butyl acetate, 2-nonanol and 1-pentanol, all from the sting, and 2-heptanone, released stinging. The alarm pheromones 2-heptanol and 3-octanone (from certain stingless bees and ants) inhibited scenting, and the former also repelled bees and released aggression. The chemicals iso-butyl acetate, sec-butyl acetate and n-pentyl acetate diminished scenting, and the insect repellents dimethyl phthalate and diethyl toluamide diminished stinging. Many of the chemicals from the honeybee sting apparatus failed to elicit a response, and their function remains unknown.
Ants, in the majority of subfamilies, are capable of stinging; in many cases, the reactions of human beings to such stings are severe enough to require immediate medical treatment. Because of their virtual ubiquity, ants constitute arthropods of considerable medical importance, although their role in inflicting stings is often unrecognized because of their relative inconspicuousness vis-à-vis flying hymenopterans such as bees and wasps. In all probability the venom arsenals of ants are highly varied but in addition, these insects also possess other exocrine glands which can be discharged during defensive encounters.
Pheromone sind Wirkstoffe, die ein Tier, speziell ein Insekt, nach außen abgibt und die auf andere Individuen der gleichen Art einwirken. Der Name ist vom griechischen „pherein” (übertragen) und „horman” (erregen, anregen) abgeleitet. Zu den Pheromonen zählen Sexuallockstoffe, Alarmstoffe, „Versammlungspheromone” u.a. Viele dieser Stoffe wirken bereits in überaus niedriger Konzentration. Unter den Insektenpheromonen befinden sich auffallend viele Derivate langkettiger, wenig verzweigter Kohlenwasserstoffe.
Using high-boiling 1,3-dimethoxybenzene instead of the normally applied low-boiling solvents, it is possible to characterize volatile compounds in insects by combined gas chromatography/mass spectrometry within a short time using small amounts of starting material. The occurrence of 3-octanon and 3-octanol in Cremastogaster scutellaris and C. ashmedi has been shown by this method. Only 200 ant heads were used.
The chemical composition of the tergal gland secretion was investigated in five species of cockroaches Blattella germanica, Supella supellectilium, Leucophaea maderae, Nauphoeta cinnerea, and Periplaneta americana). In all species the secretion is a mixture of proteins and volatile products.In Blaberoidea (four species) the tergal glands are present only in adult males and play a part during mating. We find four to eight proteins (several are glycoproteins) and 10 volatile products: myristic, palmitic, and oleic acids; benzothiazol, two isomers of nonylphenol, two isomers of hydroxybenzylic alcohol, dimethyl and trimethyl-naphthalene. Their percentages vary according to the species.In P. americana the tergal glands are present in adults of both sexes and in all larvae. Proteins are more numerous in larvae (6) than in adults (3) Several are glycoproteins. One of these proteins has a mol. wt of 10300. Two of the glycoproteins have been isolated, their mol. wt are 5600 and 6800. In adult females we find 6 volatile products: 2 and 3 pentanone, 3 octanone, and 3 isomers of methyl cyclohexanone. In adult males only 3: 2 and 3 pentanone, 3 octanone and in larvae only 2 and 3 pentanone. The function of all these products is discussed.
The mandibular gland secretion of the myrmicine ant, Myrmica brevinodis, was investigated and found to contain principally four components. Two of these components were major and two minor. The major components were identified as 3-octanone (1·6 μg/gland) and 3-octanol (0·7 μg/gland). Both compounds elicited alarm reactions in workers of M. brevinodis. The two minor components were identified as methyl-branched 3-octanones, but the position of the branching was not determined.
1.
The identification of the novel natural products, 6-methyl-3-octanone and 3-nonanone in extracts obtained from the mandibular glands of Myrmica brevinodis is reported. These compounds accompany the compounds 3-octanone and 3-octanol which have already been identified from this extract.
2.
Both 6-methyl-3-octanone and 3-nonanone were found to be capable of releasing alarm behaviour in M. brevinodis.
3.
The distribution of these compounds in the alarm pheromones of six North American and four European species of Myrmica was determined.
4.
A gas chromatographic comparison of the extracts of various species of Myrmica indicated that seven of the ten species gave very similar chromatograms (Fig. 1) which differ only in the ratios of the two major constituents 3-octanone and 3-octanol (Table 3). The remaining three species produce chromatograms so different from those of the majority, that they are easily set apart. The implications of these results for behavioural and taxonomic studies are discussed.
Two different manifestations of alarm behavioursensu stricto are distinguished inCremastogaster scutellaris.1.
General frenzy alarm in aggregations of workers inside and outside the nest. The behaviour of this type involves scattering of the aggregated workers and expanding the area of excitment.
2.
Alarm on a trail. This type of alarm pattern shows concentration around the alarm center.
In pheromone experiments the former type of alarm is released by exhibiting the worker's abdominal secretion, whereas the latter alarm is induced by pheromones from the mandibular gland. The behavioural pattern of this latter kind of alarm was analysed from cinematographic records. A quantitative bioassay has been established. The major components of the mandibular gland secretion, 3-octanone and 3-octanol yield an incomplete alarm reaction. Hence the synergistic involvement of its minor components, not yet identified, is assumed to be resoonsible for the release of full alarm behavior. The volatile substances of the mandibular secretion are found in rather low concentration as a permanent component of the nest odour. Their concentration is, however, not increased during intensive frenzy alarm activity in the nest, but non-identical substances, presumabely discharged from the abdominal secretion, appear in significant quantity. The mandibular gland secretion hence is assumed to be released only with the biting act in this species.
The enantiomeric composition of 3-octanol produced by the ants,Crematogaster castanea Forel andC. liengmei F. Smith, as a component of their alarm pheromone complex, has been determined to beS-(+)-3-octanol by gas chromatography of the diastereomericS-(+)-3-octanylR-(+)-trans-chrysanthemates.
Chemical analysis of the mandibular gland secretion of seven ant species in the tribe Tetramoriini showed that 3-octanone was the major component in Tetramorium sericeiventre (70%), T. caespitum (71%) and T. guineense (87%), and 3-octanol in Decamorium uelense (96%). 2-Undecanol, was the major component in T. termitobium (80%), but in two members of the subgenus Xiphomyrmex, T. angulinode and an unidentified species (D), the sesquiterpene furan, perillen, was predominant (91% and 98% respectively). Ants in this subgenus also contained 2-nonanol, 2-undecanol and 2-undecanone in their mandibular glands.
Chirality is a phenomenon that pervades the life on the Earth and has a tremendous importance for our daily lives. Many pharmaceuticals, agrochemicals, food additives, pheromones, fragrances and cosmetics are chiral. Chiral compounds play an essential role in biological systems, mainly for chemical communication among living organisms, serving as sex pheromones, aggregation pheromones, alarm pheromones, trail pheromones, attractants or repellent agents. This review summarizes our current knowledge of the biologically relevant chiral aliphatic hydroxy compounds, which are divided into eight classes according to their chemical structure: primary alcohols, secondary alcohols, tertiary alcohols, glycols and diols, hydroxy ketones, hydroxy carboxylic acids, hydroxy carboxylic esters and hydroxy amines. Information on biological functions and practical applications is summarized for each class. This information could be of interest to chemists, biochemists, biologists and pharmacists. A review with 475 references.
Pheromones are substances which are secreted to the outside by an animal, especially an insect, and received by a second individual of the same species, in which they release a specific reaction, for example, a definite behavior or developmental process. The name is derived from the Greek pherein (to bear, transmit) and hormon (impel, excite). Pheromones include, inter alia, sex attractants, warning substances, and “aggregation pheromones”. Many of these substances are effective at very low concentration. The insect pheromones are predominantly derivatives of long-chain, slightly branched hydrocarbons.
The defensive chemistry of two species of ants from Brunei in the genus Crematogaster (Physocrema group) has been investigated. Ants in this group release a white secretion from hypertrophied metapleural glands on their thorax when they are disturbed. Previously, one species in this group has been shown to produce alkylphenols and alkylresorcinols. In the present investigation, similar compounds along with salicylic acids and resorcylic acids that are anacardic acid and olivetolic acid homologs, respectively, are described from two species. The structures of these compounds were suggested by their spectroscopic data and confirmed by direct comparison with synthetic samples. Some of these compounds occur in lichens and have well documented physiological activities.
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