Anastrephin and epianastrephin, novel lactone components isolated from the sex pheromone blend of male caribbean and mexican fruit flies

Battiste, Merle A.; Strękowski, Lucjan; Vanderbilt, David P.; Visnick, Melean; King, Roy W.; Nation, James L.

doi:10.1016/s0040-4039(00)87958-7

Cited by 64 publications

(35 citation statements)

References 5 publications

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“…In spite of several unsuccessful attempts for trapping volatiles from male A. fraterculus, it was possible to identify the monoterpenes limonene, which has been reported only for A. ludens, and cis-ß-ocimene, reported only for A. suspensa. Both lactones (anastrephin and epianastrephin) here reported for A. fraterculus are also present in A. ludens and A. suspensa 3,6,14 . Analysis of the mass spectra from the liquid sample of salivary glands of male A. fraterculus led to the identification of two isomers of a sesquiterpene hydrocarbon and one lactone, (Z,E)-α-farnesene, (E,Z)-α-farnesene and (E,E)-suspensolide respectively.…”

Section: Discussionsupporting

confidence: 63%

“…Volatile compounds produced by males have previously been identified only from A. ludens and A. suspensa. Pheromone components of male flies of these two species were obtained from whole body extracts, abdominal extracts and by aeration [2][3][4][5][6][7] . Males A. ludens and A. suspensa release different proportions of the same three sesquiterpene hydrocarbons: α-farnesene, ß-bisabolene and α-transbergamotene.…”

Section: Introductionmentioning

confidence: 99%

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Volatile substances from male Anastrepha fraterculus wied. (Diptera: Tephritidae): identification and behavioural activity

Lima

House

Nascimento

2001

J. Braz. Chem. Soc.

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Substâncias voláteis produzidas por machos do gênero Anastrepha foram isoladas previamente de A. ludens e A. suspensa. Ambas as espécies acasalam no período da tarde, liberam compostos similares em diferentes proporções e apenas diferem na produção de monoterpenos. Quando estão em chamamento, os machos de A. fraterculus liberam dois isômeros do sesquiterpeno α-farnesene, três lactonas (anastrefin, epianastrefin e (E,E)-suspensolídeo) e dois monoterpenos (limoneno e (Z)-ß-ocimeno). As glândulas salivares dimórficas dos machos produzem e/ou armazenam os mesmos isômeros do α-farnesene e suspensolídeo, e quatro pirazinas. Dois desses compostos foram previamente isolados de machos de A. ludens e A. suspensa. Em bioensaios, as glândulas salivares de machos de A. fraterculus atraíram as fêmeas virgens e sexualmente ativas. No entanto, as fêmeas sexualmente imaturas não mostraram atividade comportamental.Volatile compounds produced by calling males of Anastrepha species have previously been reported from A. ludens and A. suspensa. Both species mate in the afternoon, release a similar range of compounds in different proportions, and only differ in the production of monoterpenes. When calling, male A. fraterculus releases two isomers of the sesquiterpene α-farnesene, three lactones (anastrephin, epianastrephin and (E,E)-suspensolide), and two monoterpenes (limonene and (Z)-ß-ocimene). The dimorphic male salivary glands produce and/or store the same isomers of α-farnesene and suspensolide, and four pyrazines. Two of these compounds have been previously reported from male A. ludens and A. suspensa. Salivary glands from virgin calling male A. fraterculus showed behavioural activity when bioassayed with virgin mature female flies, but immature females were not attracted.

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Section: Discussionsupporting

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Volatile substances from male Anastrepha fraterculus wied. (Diptera: Tephritidae): identification and behavioural activity

Lima

House

Nascimento

2001

J. Braz. Chem. Soc.

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“…Recent bioassays, in fact, demonstrated that male OS is highly attractive to conspecific males and virgin females (16). Two diastereomeric trans-fused g-lactones, epianastrephin (ES) and anastrephin (AS) (collectively ES/AS) (3,16,17), were identified as aggregation pheromones since they emanated for weeks from male OS and proved to be critical for attraction (Figure 1(a)). …”

Section: Introductionmentioning

confidence: 99%

Environmentally regulated abiotic release of volatile pheromones from the sugar-based oral secretions of caribflies

Walse

Alborn

Teal

2008

Green Chemistry Letters and Reviews

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We report an abiotic mechanism for the emission of volatile insect pheromones that is controlled by environmentally induced change in the physicochemical properties of the sugar-based release matrix. Male Anastrepha suspensa (Loew) (caribflies) mark mating sites on leaf surfaces by depositing oral secretions that contain sugar, as well as, g-hydroxy acid and g-lactone forms of the diastereomeric aggregation pheromones, epianastrephin and anastrephin. The g-hydroxy acids extend emission over many days via aqueous equilibrium with the thermodynamically less preferred, but more volatile, g-lactones (Â100:1). A kinetic model, which supports a g-lactone diffusion-limited rate, was generated and tested by measuring the effect of temperature and humidity under fixed and ambient atmospheric inputs, respectively. Results show that pheromone release from the markings occurs with a periodicity that parallels relative humidity and complements the daily pattern of the caribflies' reproductive and aggregative activity. This study provides an example of a physicochemical-based inter-organism communication strategy that has been mechanistically linked to the abiotic environmental processing of volatile chemical signals. The exploitation of this natural connectivity will spur environmentally sustainable chemistries, particularly pheromone-based alternatives to insecticide application.

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“…Pheromones released by males in leks play prominent roles in attraction of females to leks and, when coupled with auditory signals, maximize the probability of females finding and landing in the vicinity of male leks (Perdomo et al, 1975(Perdomo et al, , 1976Webb et al, 1983;Heath et al, 1993;Landolt et al, 1992;Sivinski et al, 1994). To date nine compounds including (Z)-3-nonenol and (Z,Z)-3,6-nonadienol (Nation, 1983); anastrephin (trans-hexahydro-trans-4,7α-dimethyl-4-vinyl-2-(3H)-benzofuranone) and epianastrephin (trans-hexahydro-cis-4,7α-dimethyl-4-vinyl-2-(3H)-benzofuranone) (Battiste et al, 1983); suspensolide ((E,E)-4,8-dimethyl-3,8-decadien-10-olide) ; β-bisabolene (Tumlinson, 1988;Nation, 1991), E,E-α-farnesene (Rocca et al, 1992), (Z)-β-ocimene (Tumlinson, 1988;Nation, 1991), and α-trans-bergamotene (Rocca et al, 1992) have been identified from male-produced volatiles that are attractive to females. Volatile compounds are mainly released from the mouth and anus of male flies, but some volatiles may also be released directly from the cuticle (Nation, 1990(Nation, , 1991.…”

Section: Introductionmentioning

confidence: 99%

Sex pheromone components in oral secretions and crop of male caribbean fruit flies, Anastrepha suspensa (Loew)

Teal¹

2001

Arch Insect Biochem Physiol

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Chemical analysis of hexane extracts of the oral secretions from male Caribbean fruit flies, Anastrepha suspensa, resulted in identification of pheromone components including: anastrephin, epianastrephin, suspensolide, beta-bisabolene, and alpha-farnesene in a ratio of 63:396:4:8:1. Extracts of the crop from male flies contained these same components. No pheromone was detected in the extracts of female oral secretions. Bioassay of the oral secretions indicated that females were attracted to oral secretions from males but not from females. The amounts of anastrephin and epianastrephin in male oral secretions changed with age and time of the day, and were correlated with the amounts of volatile pheromone components released by male flies. The amounts of suspensolide, beta-bisabolene, and alpha-farnesene in the crop tissue were greater than those in the crop liquid, while amounts of anastrephin and epianastrephin in the crop tissue and crop liquid changed during the day. Generally, the amounts of suspensolide and beta-bisabolene decreased, and the amounts of anastrephin and epianastrephin increased from 9 am to 6 pm in both crop tissue and crop liquid. The amounts of anastrephin and epianastrephin from crop tissue or crop liquid incubated with suspensolide were significantly higher than those of control. The data show that oral secretions deposited on leaves by males contained terpenoid pheromone components that attract females and that suspensolide was converted to anastrephin and epianastrephin by enzymatic degradation in the crop of male flies.

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Anastrephin and epianastrephin, novel lactone components isolated from the sex pheromone blend of male caribbean and mexican fruit flies

Cited by 64 publications

References 5 publications

Volatile substances from male Anastrepha fraterculus wied. (Diptera: Tephritidae): identification and behavioural activity

Volatile substances from male Anastrepha fraterculus wied. (Diptera: Tephritidae): identification and behavioural activity

Environmentally regulated abiotic release of volatile pheromones from the sugar-based oral secretions of caribflies

Sex pheromone components in oral secretions and crop of male caribbean fruit flies, Anastrepha suspensa (Loew)

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