(1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane, a New Volatile Released by Males of the Papaya Borer Pseudopiazurus obesus (Col.: Curculionidae)

Zarbin, Paulo H. G.; Moreira, Marcos A. B.; Haftmann, Jenny; Tröger, Armin; Franke, Stephan; Kopf, Jürgen; Mori, Kenji; Francke, Wittko

doi:10.1021/ol100074q

Cited by 11 publications

(10 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15) The enantiomeric purity of (1R,2S)-grandisol was estimated GC analysis on a chiral capillary column to be 94% e.e. Then, (1R,2S,6R)-papayanol was obtained by reaction of (1R,2S)-grandisol with m-chloroperbenzoic acid (Tokyo Chemical Industry Co., Tokyo, Japan) as previously described by Zarbin et al 16) The minor (1R,2R,6R)-papayanol was removed by chromatography over silica gel. To oxidize papayanol to its aldehyde (papayanal), tetrapropylammonium perruthenate (76.0 mg, 0.216 mmol) (Tokyo Chemical Industry Co., Tokyo, Japan) was added in three portions to a mixture of (1R,2S,6R)-papayanol (94% e.e.)…”

Section: Synthesis Of (1r2s6r)-papayanol and (1r2s6r)papayanalmentioning

confidence: 99%

(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

View full text Add to dashboard Cite

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.

show abstract

Section: Synthesis Of (1r2s6r)-papayanol and (1r2s6r)papayanalmentioning

confidence: 99%

(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

View full text Add to dashboard Cite

show abstract

“…The gas chromatographic analysis of SHS‐SPME samples of C. dimidiatus showed various compounds as grandisol (GI) and grandlures, which until now have been reported as aggregation pheromone of other species of Curculionidae. GI has been isolated from other curculionid beetles, such as papaya weevil Pseudopiazurus obesus (Boheman), [27,28] bark weevil Pissodes spp., [29] and the soybean stalk weevil Sternechus subsignatus [24] . Grandlure II is also a pheromone of the strawberry blossom weevil [23] .…”

Section: Resultsmentioning

confidence: 99%

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

View full text Add to dashboard Cite

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.

show abstract

“…5) were confirmed by the co-injection of authentic standards on two other GC-columns (RTX-wax and HP-1). With the exception of compounds B and G, the male-specific compounds extracted from S. subsignatus have been found to be aggregation pheromone components in several other species in the family Curculionidae, such Pseudopiazurus obesus (Zarbin et al, 2007b(Zarbin et al, , 2010, Anthonomus eugenii (Eller et al, 1994), A. grandis (Tumlinson et al, 1969), A. rubi (Innocenzi et al, 2001), Curculio caryae (Hedin et al, 1997), Bothynoderes punctiventris (Tóth et al, 2007), and Pissodes spp. (Booth et al, 1983;Philips et al, 1984).…”

Section: Resultsmentioning

confidence: 99%

Identification of Male-Produced Aggregation Pheromone of the Curculionid Beetle Sternechus subsignatus

2012

Self Cite

View full text Add to dashboard Cite

Analyses of the headspace volatiles produced by males and females of Sternechus subsignatus Boheman (Coleoptera: Curculionidae) revealed seven male-specific compounds. The major component was (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, and the minor components were 1-(2'-hydroxyethyl)-1-methyl-2-isopropenylcyclobutane (grandisol), 7-methyl-3-methyleneoct-6-en-1-ol, (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol, (Z)- and (E)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, and (E)-2-(3,3-dimethylcyclohexylidene) acetic acid. The latter compound is described for the first time as a natural product. Only four of the seven identified compounds showed electrophysiological activity. Enantioselective gas chromatography showed that the natural grandisol is the (1R,2S)-stereoisomer. The major component, (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, attracted S. subsignatus in olfactometer bioassays. Studies are in progress to evaluate the biological activity of the major component and the EAD-active mixture under field conditions.

show abstract

(1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane, a New Volatile Released by Males of the Papaya Borer Pseudopiazurus obesus (Col.: Curculionidae)

Abstract: Sex-specific volatiles produced by males of the papaya beetle Pseudopiazurus obesus are (1R,2S)-grandisal (1), (1R,2S)-grandisol (2), and the new (1R,2S,6R)-2-hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane (3) termed papayanol.

Cited by 11 publications

References 9 publications

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

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

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

Identification of Male-Produced Aggregation Pheromone of the Curculionid Beetle Sternechus subsignatus

Contact Info

Product

Resources

About