Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

Павлова, А. В.; Mikhalchenko, Oksana S.; Rogachev, Artem D.; Ильина, И. В.; Корчагина, Д. В.; Gatilov, Yuriy V.; Толстикова, Т. Г.; Волчо, К. П.; Salakhutdinov, N. F.

doi:10.1007/s00044-015-1426-5

Cited by 19 publications

(8 citation statements)

References 12 publications

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“…Hexane (99%) was supplied by JT Baker, dichloromethane (supraSolv grade) by Merck and the hydrocarbon mixture (C8‐C20) by Fluka. (+)‐ trans ‐verbenol was synthesized from (+)‐ α ‐pinene according to Pavlova et al (). Verbenene was obtained after reduction of verbenone following the procedures of Gemal and Luche () and Uzarewicz and Dresler ().…”

Section: Methodsmentioning

confidence: 99%

Identification of pheromone candidates for the eucalyptus weevil, Gonipterus platensis (Coleoptera, Curculionidae)

Mateus

Silva

Mendes

et al. 2019

J Applied Entomology

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The eucalyptus weevil, Gonipterus platensis (Coleoptera, Curculionidae), is a major pest of eucalyptus plantations worldwide. To date, no pheromones have been identified for this species, despite their valuable potential as tools in monitoring or control strategies. Here we report the detection and identification of pheromones candidates of G. platensis. The weevil's volatile compounds were collected by solid phase micro extraction (SPME) and monolithic material sorption extraction (MMSE). Using Gas Chromatography coupled to Mass Spectrometry (GC/MS) analysis, eleven insect specific compounds were detected and identified: verbenene, cis‐verbenol, trans‐verbenol, verbenone, 2‐oxo‐1,8‐cineole, 9‐hydroxy‐1,8‐cineole, 2‐α‐hydroxy‐1,8‐cineole, 3‐oxo‐1,8‐cineole, 2‐β‐hydroxy‐1,8‐cineole, 3‐α‐hydroxy‐1,8‐cineole and 7‐hydroxy‐1,8‐cineole. Three of these compounds, verbenene, cis‐verbenol and trans‐verbenol, were shown to be male‐specific. Antennal sensitivity towards ten compounds emitted by G. platensis was detected using Gas Chromatography–Mass Spectrometry/Electroantennographic Detection (GC‐MS/EAD). Extracts from virgin males proved to be attractive to virgin females in olfactometer bioassays. Further behavioural bioassays showed that both virgin females and virgin males were attracted to the male‐specific compound cis‐verbenol and that virgin females were attracted to trans‐verbenol. Verbenone was attractive to mated females. Regarding 2‐α‐hydroxy‐1.8‐cineole and 2‐oxo‐1,8‐cineole, which are produced by both sexes, the alcohol was attractive to virgin males and both the alcohol and the ketone were repellant to mated females. This is, to our knowledge, the first identification of pheromones candidates in Gonipterus spp. and also the first evidence of cineole metabolites acting as semiochemicals.

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Section: Methodsmentioning

confidence: 99%

Identification of pheromone candidates for the eucalyptus weevil, Gonipterus platensis (Coleoptera, Curculionidae)

Mateus

Silva

Mendes

et al. 2019

J Applied Entomology

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“…(Z)-3-Hexen-1-yl acetate (98%), (+)-α-pinene (>99%), (−)-α-pinene (98%), camphene (95%), (+)-β-pinene (98%), (−)-β-pinene (98%), β-myrcene (95%), (R)-(+)-limonene (97%) (S)-(−)limonene (96%), 1,8-cineole (99%), γ-terpinene (97%), p-cymene (97%), α-terpino lene (≥90%), linalool oxide (≥97%), sabinene hydrate (≥97%), (−)-α-gurjunene (≥97%), (+) calarene (≥99%), β-caryophyllene (98,5%), (+)-aromadendrene (≥97%), (−)-trans-pi nocarveol (≥96%), (+)-fenchol (analytical standard), (−)-allo-aromadendrene (≥98%), α-ter pineol (90%), α-terpinenyl acetate (≥95%), (+)-ledene (≥95%), (1R)-(−)-myrtenol (95%), (−) carveol (97%), 2-phenylethanol (≥99%), phenylethyl isovalerate (≥98%), (−)-epi-globulo (≥95%), (−)-globulol (≥98.5%), (S)-(−)-perillyl alcohol (≥95%), (S)-cis-verbenol (95%), (1S) (−)-verbenone (94%) and paraffin oil (for IR spectroscopy) were purchased from Sigma Aldrich (Steinheim, Germany). Regarding the synthesized compounds: (+)-trans-verbeno was prepared from (+)-α-pinene [49]; verbenene synthesized from verbenone [50,51]; 2-α hydroxy-1,8-cineole and 2-oxo-1,8-cineole were prepared according to the procedure previously described [52]; 9-Hydroxy-1,8-cineole was synthesized from R-(+)-limonene [53]. Hexane (99%) was supplied by JT Baker (Deventer, The Netherlands), dichloro methane (Suprasolv grade) and anhydrous sodium sulphate by Merck (Darmstadt, Ger many) and (Z)-3-hexen-1-ol (98%), ocimene (mixture of isomers, ≥90%), (−)-α-copaene (>90), α-phellandrene (≥85), geraniol (≥98%) and the hydrocarbon mixture (C8-C20) by Fluka (Neu-Ulm, Germany).…”

Section: Reagents and Materialsmentioning

confidence: 99%

Unveiling Chemical Cues of Insect-Tree and Insect-Insect Interactions for the Eucalyptus Weevil and Its Egg Parasitoid by Multidimensional Gas Chromatographic Methods

et al. 2022

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Multidimensional gas chromatography is, presently, an established and powerful analytical tool, due to higher resolving power than the classical 1D chromatographic approaches. Applied to multiple areas, it allows to isolate, detect and identify a larger number of compounds present in complex matrices, even in trace amounts. Research was conducted to determine which compounds, emitted by host plants of the eucalyptus weevil, Gonipterus platensis, might mediate host selection behavior. The identification of a pheromone blend of G. platensis is presented, revealing to be more attractive to weevils of both sexes, than the individual compounds. The volatile organic compounds (VOCs) were collected by headspace solid phase microextraction (HS-SPME), MonoTrapTM disks, and simultaneous distillation-extraction (SDE). Combining one dimensional (1D) and two-dimensional (2D) chromatographic systems—comprehensive and heart-cut two-dimensional gas chromatography (GC×GC and H/C-MD-GC, respectively) with mass spectrometry (MS) and electroantennographic (EAD) detection, enabled the selection and identification of pertinent semiochemicals which were detected by the insect antennal olfactory system. The behavioral effect of a selected blend of compounds was assessed in a two-arm olfactometer with ten parallel walking chambers, coupled to video tracking and data analysis software. An active blend, composed by cis and trans-verbenol, verbenene, myrtenol and trans-pinocarveol was achieved.

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“…(+)-trans-verbenol was synthesized from (+)α-pinene according to Pavlova et al (2015). Verbenene was obtained after reduction of verbenone according to the procedures of Gemal and Luche (1981) and Dess-Martin periodinane at room temperature (Schaffarczyk et al, 2013).…”

Section: Standard Compoundsmentioning

confidence: 99%

Olfactory responses of Anaphes nitens (Hymenoptera, Mymaridae) to host and habitat cues

Mateus

Silva

Mendes

et al. 2021

J Applied Entomology

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show abstract

Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

Cited by 19 publications

References 12 publications

Identification of pheromone candidates for the eucalyptus weevil, Gonipterus platensis (Coleoptera, Curculionidae)

Identification of pheromone candidates for the eucalyptus weevil, Gonipterus platensis (Coleoptera, Curculionidae)

Unveiling Chemical Cues of Insect-Tree and Insect-Insect Interactions for the Eucalyptus Weevil and Its Egg Parasitoid by Multidimensional Gas Chromatographic Methods

Olfactory responses of Anaphes nitens (Hymenoptera, Mymaridae) to host and habitat cues

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