(1R,2S,6R)-Papayanol, Aggregation Pheromone of the Guava Weevil,Conotrachelus psidii

Palacio-Cortés, Angela María; Valente, Fabrício Iglesias; Saad, Emir B.; Tröger, Armin; Francke, Wittko; Zarbin, Paulo H. G.

doi:10.5935/0103-5053.20150040

Cited by 5 publications

(10 citation statements)

References 2 publications

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“…The supply of the host plant and not apple pieces in the entrainment chambers during the volatile collection stimulates the pheromone production from male adults. This phenomenon has been reported in other curculionidae species such as A. grandis (Dickens, 1989), Anthonomus musculus (Szendrei et al, 2011), Rynchophorus phoencis (Jaffé et al, 1993), R. palmarum (Oehlschlager et al, 1992), Pissodes strobi, Pissodes approximatus (Booth et al, 1983) and, recently, by Conotrachelus psiidi (Palacio-Cortés et al, 2015).…”

Section: Discussionsupporting

confidence: 58%

Identification of male-produced aggregation pheromone of the curculionid beetle Acrotomopus atropunctellus

Rodriguez

Perez

Nazareno

2016

Bull. Entomol. Res.

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The sugarcane stem weevil, Acrotomopus atropunctellus (Boheman) (Curculionidae: Molytinae: Cholini) is an important economic pest from the Northwestern region of Argentina. Analyses of the headspace volatiles produced by separated males and females revealed one male-specific compound. Its structural identification is reported here in using gas chromatography coupled with mass spectroscopy analysis and chemical micro-reactions. Besides, two laboratory olfactometry assays allowed us to propose 6-methyl-5-hepten-2-one (sulcatone) as an aggregation pheromone for this insect, being attractive to both conspecific males and females. This compound is reported for the first time as involved in the Curculionidae family communication.

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Section: Discussionsupporting

confidence: 58%

Identification of male-produced aggregation pheromone of the curculionid beetle Acrotomopus atropunctellus

Rodriguez

Perez

Nazareno

2016

Bull. Entomol. Res.

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“…Although the taxonomically related species C. psidii and C. dimidiatus have the same eating habits, the compounds P-OL [36] and P-AL [10] were identified only in males of C. psidii while we found P-OL both in males and females of C. dimidiatus. Then, we directed additional efforts of our research to confirm the release of P-OL by both females and males of the weevil under study, to find differences at a biochemical level between C. dimidiatus and C. psidii.…”

Section: Aggregation Pheromones Papayanol and Papayanalcontrasting

confidence: 45%

Profile of Terpenoid Compounds Mediating a Plant‐Herbivore Interaction: Screening by Static Headspace Solid‐Phase Microextraction‐Gas Chromatography/Q‐ToF Mass Spectrometry

García-Díaz

Trejo

Tafoya

et al. 2020

Chemistry & Biodiversity

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Conotrachelus dimidiatus (Coleoptera: Curculionidae) interacts with immature guava fruits (Psidium guajava L.) for feed, sleep, mate and oviposit. Determination of the volatile organic compounds (VOCs) emitted by the insect and immature fruits can help improve understanding of plant-insect and intraspecific insect interactions between females and males of C. dimidiatus. Daytime fruit setting emissions of immature guava consist mainly of limonene, caryophyllene, and aromadendrene. In addition to the host's volatiles, the aim of this study was to assess the VOCs released by the insect. Static headspace-solid phase microextraction (SHS-SPME), combined with gas chromatography/quadrupole time of flight mass spectrometry (GC/Q-ToF-MS), allowed the identification of the C 10 terpenoids: grandlure I, II, II, IV, grandisoic acid, papayanol and papayanal bioactive compounds released by female and male C. dimidiatus under laboratory conditions. These chemical compounds are candidates for the preparation of a lure formulation.

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“…4(A)), in agreement with those results reported by for Brazilian C. psidii. 12) The minor male-specific compound 4, showed a fragmentation pattern very similar to that of (1R,2S,6R)-papayanol by mass spectrometry (Fig. 3(B) and (D)), suggesting in the first instance the presence Table 1.…”

Section: Resultsmentioning

confidence: 70%

“…To this regard, it has been reported that the response of an insect to a specific volatile compound is significantly influenced by its concentration. 23) The study carried out by Palacio-Cortés et al 12) with Brazilian population of C. psidii showed that synthetic papayanol (100 μg/ml) did not attract insects without host plant volatiles. However, the authors did not use papayanal in their treatments, contrasting with the results here presented for Colombian population.…”

Section: Discussionmentioning

confidence: 98%

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(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevil Conotrachelus psidii (Coleoptera: Curculionidae)

Romero-Frías

Murata²,

Bento

et al. 2016

Bioscience, Biotechnology, and Biochemistry

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The guava weevil, Conotrachelus psidii is an aggressive pest of guava (Psidium guajava L.) that causes irreparable damages inside the fruit. The volatile compounds of male and female insects were separately collected by headspace solid-phase microextraction or with dynamic headspace collection on a polymer sorbent, and comparatively analyzed by GC-MS. (1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane (papayanol), and (1R,2S,6R)-2,6-dimethyl-3-oxabicyclo[4.2.0]octane-2-carbaldehyde (papayanal) were identified (ratio of 9:1, respectively) as male-specific guava weevil volatiles. Papayanal structure was confirmed by comparison of spectroscopic (EIMS) and chromatographic (retention time) data with those of the synthetic pure compound. The behavioral response of the above-mentioned compounds was studied in a Y-tube olfactometer bioassay, and their role as aggregation pheromone candidate components was suggested in this species.

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(1R,2S,6R)-Papayanol, Aggregation Pheromone of the Guava Weevil,Conotrachelus psidii

Cited by 5 publications

References 2 publications

Identification of male-produced aggregation pheromone of the curculionid beetle Acrotomopus atropunctellus

Identification of male-produced aggregation pheromone of the curculionid beetle Acrotomopus atropunctellus

Profile of Terpenoid Compounds Mediating a Plant‐Herbivore Interaction: Screening by Static Headspace Solid‐Phase Microextraction‐Gas Chromatography/Q‐ToF Mass Spectrometry

(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevil Conotrachelus psidii (Coleoptera: Curculionidae)

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