Chemical Compounds from Female and Male Rectal Pheromone Glands of the Guava Fruit Fly, Bactrocera correcta

Zhang, Xiu-ge; Wei, Cheng-Mei; Miao, J. C.; Zhang, Xiaojiao; Wei, Bo; Dong, Wen-Xia; Chun, Xiao

doi:10.3390/insects10030078

Cited by 13 publications

(13 citation statements)

References 29 publications

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“…A full listing of the compounds identified in rectal gland extracts and emissions of B. tryoni is provided in Table 1. Twenty two compounds were detected in rectal gland extracts and headspace collections of sexually mature virgin female B. tryoni, including five amides (6, 7, 9, 10 and 12), six spiroacetals (13)(14)(15)(16)(17)(18) and eleven esters (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29). Of these, 19 compounds were detected in the headspace.…”

Section: Resultsmentioning

confidence: 99%

Sampling technique biases in the analysis of fruit fly volatiles: a case study of Queensland fruit fly

Noushini

Park

Jamie

et al. 2020

Sci Rep

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Diverse methods have been used to sample insect semiochemicals. Sampling methods can differ in efficiency and affinity and this can introduce significant biases when interpreting biological patterns. We compare common methods used to sample tephritid fruit fly rectal gland volatiles (‘pheromones’), focusing on Queensland fruit fly, Bactrocera tryoni. Solvents of different polarity, n-hexane, dichloromethane and ethanol, were compared using intact and crushed glands. Polydimethylsiloxane, polydimethylsiloxane/divinylbenzene and polyacrylate were compared as adsorbents for solid phase microextraction. Tenax-GR and Porapak Q were compared as adsorbents for dynamic headspace sampling. Along with compounds previously reported for B. tryoni, we detected five previously unreported compounds in males, and three in females. Dichloromethane extracted more amides while there was no significant difference between the three solvents in extraction of spiroacetals except for (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane for which n-hexane extracted higher amount than both dichloromethane and ethanol. Ethanol failed to contain many of the more volatile compounds. Crushed rectal gland samples provided higher concentrations of extracted compounds than intact rectal gland samples, but no compounds were missed in intact samples. Of solid phase microextraction fibers, polyacrylate had low affinity for spiroacetals, ethyl isobutyrate and ethyl-2-methylbutanoate. Polydimethylsiloxane was more efficient for spiroacetals while type of fiber did not affect the amounts of amides and esters. In dynamic headspace sampling, Porapak was more efficient for ethyl isobutyrate and spiroacetals, while Tenax was more efficient for other esters and amides, and sampling time was a critical factor. Biases that can be introduced by sampling methods are important considerations when collecting and interpreting insect semiochemical profiles.

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Section: Resultsmentioning

confidence: 99%

Sampling technique biases in the analysis of fruit fly volatiles: a case study of Queensland fruit fly

Noushini

Park

Jamie

et al. 2020

Sci Rep

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“…(E,E)-2-Ethyl-8-methyl-1,7-dioxaspiro[5.5]undecane has been previously reported as part of male emanations of B. nigrotibialis, Bactrocera halfordiae (Tryon), B. dorsalis, B. kirki, Bactrocera latifrons (Hendel) and Bactrocera occipitalis (Bezzi) as well as female emanations of B. tryoni and B. musae (Perkins et al 1990b;Symonds et al 2009;Benelli et al 2014;El-Sayed et al 2019;Noushini et al 2019). 2-Propyl-8-methyl-1,7-dioxaspiro[5.5]undecane has been identified in n-pentane extracts of the abdomen of female B. tryoni (Booth et al 2006 (Canale et al 2015;El-Sayed et al 2019;Zhang et al 2019). Of these, ethyl caprate and methyl palmitate have been reported as attractants for both B. oleae males and females (Canale et al 2015).…”

Section: Discussionmentioning

confidence: 99%

Rectal gland exudates and emissions of Bactrocera bryoniae: chemical identification, electrophysiological and pheromonal functions

et al. 2020

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Bactrocera bryoniae is a polyphagous and economically significant fruit fly found in Indonesia, Papua New Guinea and Australia. To understand chemical-mediated sexual communication, and the potential for novel pheromone-based attractants for monitoring and mass-trapping of B. bryoniae, rectal gland exudates and emissions from sexually mature males and females were investigated. Gas chromatography-mass spectrometry showed that male rectal glands contained six compounds, of which 1,7-dioxaspiro [5,5]undecane elicited electroantennographic (EAD) and electropalpographic (EPD) responses in both sexes, ethyl 3-acetoxybutanoate elicited EPD responses in both sexes, N-(3-methylbutyl)acetamide elicited EAD response from males and 4-hydroxy-1,7-dioxaspiro[5.5]undecane elicited EAD responses in males and females and EPD responses in females. Female rectal glands contained 23 compounds with the esters ethyl laurate and ethyl myristate as major components. Amongst the female rectal gland constituents, ethyl laurate, ethyl myristate and ethyl palmitate elicited EAD responses in males and females, N-(3-methylbutyl)acetamide elicited EAD responses in males only, (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane elicited EAD responses in males and EPD responses in females, and 2,7-dimethyl-1,6-dioxaspiro[4.5] decane, (E,E)-2-ethyl-7-methyl-1,6-dioxaspiro[4.5]decane, (E,E)-2-ethyl-8-methyl-1,7-dioxaspiro[5.5]undecane, (Z,Z)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane, (E,E)-2-propyl-8-methyl-1,7-dioxaspiro[5.5]undecane and ethyl caprate elicited EPD responses in females only. Y-tube bioassays indicated that male rectal gland extracts and headspace volatiles attracted females and males, while female rectal gland extracts and headspace volatiles only attracted males. The results suggest that ethyl 3-acetoxybutanoate, 1,7-dioxaspiro [5,5]undecane and 4-hydroxy-1,7-dioxaspiro[5.5]undecane may be components of male-produced sex pheromone in B. bryoniae while (E,E)-2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, N-(3-methylbutyl) acetamide, ethyl laurate, ethyl myristate and ethyl palmitate may be components of female-produced sex pheromone. Ethyl 3-acetoxybutanoate, N-(3-methylbutyl) acetamide, 1,7-dioxaspiro [5,5]undecane and 4-hydroxy-1,7-dioxaspiro[5.5]undecane may be components of male aggregation pheromone. These findings contribute to the understanding of pheromone communication in B. bryoniae and provide a foundation for developing pheromone-based monitoring and control methods.

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“…In order to identify electrophysiologically active components present in the emissions of each sex, we used gas chromatography-electroantennogram detection (GC-EAD) and gas chromatography-electropalpogram detection (GC-EPD) to test the responses of male and female antennae and maxillary palps to the emissions of male and female rectal glands. The rectal gland contents were tested for attraction of the opposite and same sex using y-maze olfactometers [49][50][51].…”

Section: Introductionmentioning

confidence: 99%

Attraction and Electrophysiological Response to Identified Rectal Gland Volatiles in Bactrocera frauenfeldi (Schiner)

et al. 2020

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Bactrocera frauenfeldi (Schiner) (Diptera: Tephritidae) is a polyphagous fruit fly pest species that is endemic to Papua New Guinea and has become established in several Pacific Islands and Australia. Despite its economic importance for many crops and the key role of chemical-mediated sexual communication in the reproductive biology of tephritid fruit flies, as well as the potential application of pheromones as attractants, there have been no studies investigating the identity or activity of rectal gland secretions or emission profiles of this species. The present study (1) identifies the chemical profile of volatile compounds produced in rectal glands and released by B. frauenfeldi, (2) investigates which of the volatile compounds elicit an electroantennographic or electropalpographic response, and (3) investigates the potential function of glandular emissions as mate-attracting sex pheromones. Rectal gland extracts and headspace collections from sexually mature males and females of B. frauenfeldi were analysed by gas chromatography-mass spectrometry. Male rectal glands contained (E,E)-2-ethyl-8-methyl-1,7-dioxaspiro [5.5]undecane as a major component and (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane as a moderate component. Minor components included palmitoleic acid, palmitic acid, and ethyl oleate. In contrast, female rectal glands contained (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane and ethyl laurate as major components, ethyl myristate and ethyl palmitoleate as moderate components, and 18 minor compounds including amides, esters, and spiroacetals. Although fewer compounds were detected from the headspace collections of both males and females than from the gland extractions, most of the abundant chemicals in the rectal gland extracts were also detected in the headspace collections. Gas chromatography coupled electroantennographic detection found responses to (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane from the antennae of both male and female B. frauenfeldi. Responses to (E,E)-2-ethyl-8-methyl-1,7-dioxaspiro[5.5]undecane were elicited from the antennae of females but not males. The two spiroacetals also elicited electropalpographic responses from both male and female B. frauenfeldi. Ethyl caprate and methyl laurate, found in female rectal glands, elicited responses in female antennae and palps, respectively. Y-maze bioassays showed that females were attracted to the volatiles from male rectal glands but males were not. Neither males nor females were attracted to the volatiles from female rectal glands. Our findings suggest (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane and (E,E)-2-ethyl-8-methyl-1,7-dioxaspiro[5.5]undecane as components of a sex-attracting pheromone in B. frauenfeldi.

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Chemical Compounds from Female and Male Rectal Pheromone Glands of the Guava Fruit Fly, Bactrocera correcta

Cited by 13 publications

References 29 publications

Sampling technique biases in the analysis of fruit fly volatiles: a case study of Queensland fruit fly

Sampling technique biases in the analysis of fruit fly volatiles: a case study of Queensland fruit fly

Rectal gland exudates and emissions of Bactrocera bryoniae: chemical identification, electrophysiological and pheromonal functions

Attraction and Electrophysiological Response to Identified Rectal Gland Volatiles in Bactrocera frauenfeldi (Schiner)

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