Olfactory stimuli were delivered with a custom-built olfactometer comprising eight odor channels and controlled via a custom-made LabVIEW (National Instruments, Austin, TX, USA) interface, which synchronized stimulation protocol with the imaging acquisition [21 ]. For this study, we used six ecologically relevant odorants known to elicit distinct responses in the antennal lobe glomeruli: 1-hexanol (1HEX), 3-hexanol (3HEX), 1-nonanol (1NON), isoamyl acetate (ISOA), acetophenone (ACTP), and benzaldehyde (BZDA) (all from Sigma-Aldrich) [2 (link),9 (link)]. Additionally, they provide different degrees of structural and functional variability: 1-hexanol and 3-hexanol have the same carbon length but vary for the position of the hydroxyl group; 1-hexanol and 1-nonanol are primary alcohols with different chain lengths; acetophenone and benzaldehyde both have a benzene ring, but with a ketone and an aldehyde group, respectively; isoamyl acetate is the major component of the honey bee alarm pheromone [27 (link)], while all other odorants are typical floral scent components. Stimuli were presented in a 1 s ON/9 s OFF protocol and each odorant was delivered for 30 consecutive trials. All odorants were diluted 1:200 in mineral oil (Sigma-Aldrich). These concentrations were chosen to be well above the receptor sensitivity threshold and below the saturation level [5 (link)].
1 nonanol
Manufactured by Merck Group
Sourced in United States
1-nonanol is a linear primary alcohol with the chemical formula CH3(CH2)8OH. It is a clear, colorless liquid with a mild, fatty odor. 1-nonanol is commonly used as a chemical intermediate in the production of various compounds and as a solvent in laboratory and industrial applications.
Automatically generated - may contain errors
Lab products found in correlation
1 hexanol, by Merck Group (3 mentions)
Benzaldehyde, by Merck Group (2 mentions)
Geranyl acetone, by Merck Group (2 mentions)
Mineral oil, by Merck Group (1 mentions)
Acetophenone, by Merck Group (1 mentions)
Isoamyl acetate, by Merck Group (1 mentions)
Labview, by National Instruments (1 mentions)
3 hexanol, by Merck Group (1 mentions)
P cymene, by Merck Group (1 mentions)
1 8 cineole, by Merck Group (1 mentions)
γ terpinene, by Merck Group (1 mentions)
Amitraz, by Merck Group (1 mentions)
Fluvalinate, by Merck Group (1 mentions)
Acetone, by Daejung Chemicals (1 mentions)
2 methyl 1 butanol, by Merck Group (1 mentions)
2 ethylhexanol, by Merck Group (1 mentions)
Limonene, by Merck Group (1 mentions)
Citral, by Merck Group (1 mentions)
Furfural, by Merck Group (1 mentions)
α terpineol, by Merck Group (1 mentions)
6 protocols using 1 nonanol
1
Ecologically Relevant Olfactory Stimuli
2
Olfactory Conditioning and Antennal Responses in Honeybees
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Antennal movements were recorded 1 h before the beginning of the conditioning procedure and 1 h after the end of the conditioning phase. Before the recording period, each bee was left to acclimatize to the airflow for 20 sec. Each recording lasted 40 sec: 15 sec of airflow, 5 sec of olfactory stimulation, and 20 sec of airflow. Each bee was recorded four times, three recordings with an olfactory stimulation and one with a constant air flow. These recordings were separated by 1 min and were carried out in a randomized order. Three odorants were used; 1-hexanol (A) and 1-nonanol (B) were used as conditioned stimuli (CSs) and octanal (C) was used as a novel odor (NOd) (all from Sigma Aldrich). These odorants were chosen because they are easily learned and well discriminated by the bees (Guerrieri et al. 2005 (link)). In addition, these CSs have been used in several studies comparing SER and PER conditioning (Vergoz et al. 2007 (link); Carcaud et al. 2009 (link)). During these antenna movement recordings, proboscis extensions could be clearly seen and recorded by the experimenter. However, due to the position of the bee and the lighting directed only to the bees’ head, sting extensions could not be monitored during these recordings.
3
Extraction and Characterization of Essential Oils
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Thymol (purity = 98.5%, CAS-No. 89-83-8), Deajung reagents chemicals, Siheung, Republic of Korea, carvacrol (purity = 97%, CAS-No. 99-85-4), Sigma Aldrich, Bengaluru, India, p-cymene (purity = 99%, CAS-No. 99-87-6), Sigma Aldrich, Massachusetts, USA, 1,8-cineole (purity > 95%, CAS-No. 470-82-6; Sigma Aldrich, Sydney, Australia, γ-terpinene (purity = 97%, CAS-No. 99-85-4), Sigma Aldrich, Buchs, Switzerland, 1-nonanol (purity > 98%; CAS No. 143–08-8), Sigma Aldrich, Gillingham, UK, Fluvalinate (purity = 95%, CAS-No. 102851-06-9), Sigma Aldrich, Buchs, Switzerland, amitraz (purity > 98%, CAS No 33089-61-1) Sigma-Aldrich, MA, USA) and acetone (purity = 99.5%; CAS No. 67-64-1; Daejung reagents chemicals, Siheung, Republic of Korea) were purchased and EOs were extracted and prepared as described below.
4
Antifungal Activity of Volatile Compounds against F. incarnatum
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To test the effect of dominant volatile compound participated in antifungal activity against F. incarnatum, the sealed plate method was conducted as shown in Section 2.3 . The compound phenylethyl alcohol (PEA) was purchased from Sigma-Aldrich (St. Louis, MO, USA). The effect of commercial PEA versus the other volatile antifungal compounds 2-ethylhexanol, 1-nonanol, 6-PP, and 2-methyl-1-butanol (Sigma-Aldrich, St. Louis, MO, USA) [6 (link)] was tested through the sealed plate method. PEA was dissolved in 95% ethanol and we adjusted the dilution to 10−1, 10−2, and 10−3. Each volatile compound was applied on a sterile cotton pad (20 µL) and subjected to the method of Wonglom et al. [6 (link)] Application of 95% ethanol served as a negative control. The tested plates were then incubated at 28 ± 2 °C for seven days. Each treatment was composed of five replicates and the experiment was repeated twice. Colony diameters of F. incarnatum were measured and the percentage inhibition was calculated as described in Section 2.2 .
5
Extraction and Quantification of Volatile Compounds
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Acetonitrile, formic acid, and methanol were purchased from Fisher Company (Fairlawn, NJ, USA). D-(+)-dextronic acid δ-lactone was purchased from Sigma-Aldrich (St. Louis, MO, USA). The Cleanert® PEP-SPE resin (150 mg/6 mL) was obtained from Bonna-Agela (Wilmington, DE, USA).
The standards (purities > 95%) used for identification and quantification of the volatile compounds 1-hexanol, (E)-2-hexen-1-ol, (Z)-2-hexen-1-ol, (E)-3-hexen-1-ol, (Z)-3-hexen-1-ol, hexanal, (E)-2-hexenal, 1-nonanol, furfural, hexanoic acid, limonene, D-limonene, myrcene, linalol, α-terpineol, 4-terpineol, β-citronellol, citral, geranylacetone, geraniol, nerol, cis-furan oxidin, spirulina, (Z)-orange sterol, (E)-β-damascenone, (E)-β-ionone, and 4-methyl-2-pentanol were all supplied by Sigma-Aldrich (St. Louis, MO, USA). The deionized water (<18 WΩ resistance) was obtained through a Milli-Q Element water purification system (Millipore, Bedford, MA, USA). All the other chemicals or reactives without especial mention were purchased from Beijing Chemical Works (Beijing, China).
The standards (purities > 95%) used for identification and quantification of the volatile compounds 1-hexanol, (E)-2-hexen-1-ol, (Z)-2-hexen-1-ol, (E)-3-hexen-1-ol, (Z)-3-hexen-1-ol, hexanal, (E)-2-hexenal, 1-nonanol, furfural, hexanoic acid, limonene, D-limonene, myrcene, linalol, α-terpineol, 4-terpineol, β-citronellol, citral, geranylacetone, geraniol, nerol, cis-furan oxidin, spirulina, (Z)-orange sterol, (E)-β-damascenone, (E)-β-ionone, and 4-methyl-2-pentanol were all supplied by Sigma-Aldrich (St. Louis, MO, USA). The deionized water (<18 WΩ resistance) was obtained through a Milli-Q Element water purification system (Millipore, Bedford, MA, USA). All the other chemicals or reactives without especial mention were purchased from Beijing Chemical Works (Beijing, China).
6
Profiling Fermented Bamboo Shoots Volatiles
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Several chemical standards were purchased from Sigma-Aldrich (Shanghai, China): propanal, ethyl acetate, octanal, nonanal, 1-octen-3-ol, (E)-2-octenal, acetic acid, benzaldehyde, 1-nonanol, methyl salicylate, guaiacol, geranylacetone, phenylethyl alcohol, creosol, 4-ethylguaiacol, anisaldehyde, p-cresol, and 4-ethyl-phenol. The internal standard (2-methyl-3-heptanone) and a C7-C40 n-alkane mixture were purchased from Sigma-Aldrich. Chemical standards and internal standards were of a high-purity grade (GC grade ≥ 97% purity). GFBS were collected from several fermentation workshops (in the City of Liuzhou (LZ), Nanning (NN), Guilin (GL), and Baise (BS), Guangxi Zhuang Autonomous Region, China), in which the fresh shoots of Dendrocalamus latiflorus Munro were peeled and then steeped in mountain spring water for anaerobically fermenting in a jar for 30 d at 25 °C. Their basic information is listed in Appendix A Table A1 . All samples were wrapped in nylon/polyethylene and stored at −20 °C until analysis.
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