Cuminaldehyde

Manufactured by Merck Group

Sourced in United States

Cuminaldehyde is a colorless to pale yellow liquid organic compound. It has a characteristic odor and is used as a flavoring agent and in the synthesis of various chemical compounds.

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8 protocols using cuminaldehyde

Antimicrobial Potential of Cuminaldehyde

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Cuminaldehyde (98% purity; Sigma-Aldrich) antimicrobial effects were investigated by the microdilution method [40 (link)]. For this, the bacteria previously cultured on MH agar were suspended in saline (~ 1.5 × 10⁸ colony forming units (CFU)/milliliter (ml)). For determining the MICs, 10 μl of the bacterial suspension were incubated in MH broth (190 μl/well; Merck Millipore) containing different concentrations of Cuminaldehyde (0.0234–24 mg/ml). Serial dilutions of ciprofloxacin (0.0009–200 μg/ml) were used as positive controls. Sterile dimethyl sulfoxide (DMSO, Sigma-Aldrich; 2% in saline) was used to increase Cuminaldehyde solubility and as negative control. Samples were incubated for 24 h at 37°C, and the MICs (the lowest concentration at which no bacterial growth is observed) were evaluated. For this, the absorbances were read at 600 nm.
In parallel, the effects of the sub-inhibitory concentrations (MIC/2-MIC/8) of Cuminaldehyde and ciprofloxacin on bacterial viability were assessed and calculated by addition of the PrestoBlue® reagent (1:10; Life Technologies), according to the manufacturer’s instructions. The absorbance was read at 570 nm and 600 nm and cell viability expressed as Δ absorbance in nm.

Monteiro-Neto V., de Souza C.D., Gonzaga L.F., da Silveira B.C., Sousa N.C., Pontes J.P., Santos D.M., Martins W.C., Pessoa J.F., Carvalho Júnior A.R., Almeida V.S., de Oliveira N.M., de Araújo T.S., Maria-Ferreira D., Mendes S.J., Ferro T.A, & Fernandes E.S. (2020). Cuminaldehyde potentiates the antimicrobial actions of ciprofloxacin against Staphylococcus aureus and Escherichia coli. PLoS ONE, 15(5), e0232987.

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Single-cell Calcium Imaging of DRG

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Single cell calcium imaging experiments were performed on an AXIO Observer. D1 (Zeiss), a digital camera ORCA-Flash4.0 (Hamamatsu), a High Speed Polychromator System VisiChrome and acquired by VisiView software (Visitron Systems GmbH). The day of experiment, DRG were loaded during 45 min in Fluo 4 containing probenecid (Fluo-4 NW Calcium Assay Kit, Molecular Probes, cat.number F36206). Coverslips were mounted in a bath-imaging chamber RC-25F, with VC-8 Valves Controller through a dual automatic temperature controller TC-344B (Warner Instruments). DRG are continuous perfused at 37 °C with HBSS, 20 mM HEPES, 2 mM CaCl2, pH7.4 (Sigma). DRG were first perfused 10 min for washing, and stimulations were performed during 50 s with 25 mM Tiglic Aldehyde, 5 mM p-Anisaldehyde, 3 mM Cuminaldehyde, 100 µM Cinnamaldehyde (Sigma) and 10 µM Capsaicin (Sigma). 50 mM KCl (Sigma) was used as the positive control. Fluorescence was measured using excitation at 494 nm and emission at 516 nm.

Legrand C., Merlini J.M., de Senarclens-Bezençon C, & Michlig S. (2020). New natural agonists of the transient receptor potential Ankyrin 1 (TRPA1) channel. Scientific Reports, 10, 11238.

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Reagents for Cell Culture Experiments

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We purchased RPMI-1640 and fetal bovine serum (FBS) from GIBCO BRL (Gaithersburg, MD, USA), together with dimethyl sulfoxide and cuminaldehyde from Sigma-Aldrich, Inc. (St. Louis, MO, USA).

Tsai K.D., Liu Y.H., Chen T.W., Yang S.M., Wong H.Y., Cherng J., Chou K.S, & Cherng J.M. (2016). Cuminaldehyde from Cinnamomum verum Induces Cell Death through Targeting Topoisomerase 1 and 2 in Human Colorectal Adenocarcinoma COLO 205 Cells. Nutrients, 8(6), 318.

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Evaluation of Cuminaldehyde and Cuminol

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HSA (≥99%, A3782), cuminaldehyde (≥98.0%, 135,178) and cuminol or 4-Isopropylbenzyl alcohol (≥97.0%, 196,037) were purchased from Sigma, Plymouth Road Livonia, MI, USA. The experiments were carried out in a 20 mM Tris buffer of pH 7.4. The concentrated stock solutions of cuminaldehyde and cuminol were prepared in ethanol. The experiments using the techniques described below were performed in triplicate.

Ali M.S., Rehman M.T., Al-Lohedan H, & AlAjmi M.F. (2022). Spectroscopic and Molecular Docking Investigation on the Interaction of Cumin Components with Plasma Protein: Assessment of the Comparative Interactions of Aldehyde and Alcohol with Human Serum Albumin. International Journal of Molecular Sciences, 23(8), 4078.

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Urease Enzyme Assay with Terpenes

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urease (Type IX from Canavalia ensiformis (Jack Bean), specific activity: 50,000–100,000 units/g), compounds Camphene (CID: 6616) and Cuminaldehyde (CID:326) were purchased from Sigma Aldrich (Saint Louis, MO, USA). One unit of urease enzyme is equivalent to 1.0 I.U. Other chemicals such as urea, thiourea, sodium nitroprusside and phenol were obtained from Hi-Media. All reagents were of analytical grade.

Kumar M., Sikri N., Chahal S., Sharma J., Sharma B., Yadav P., Bhardwaj M., Vashishth D., Kadyan P., Kataria S.K, & Dalal S. (2021). Urease Inhibitory Kinetic Studies of Various Extracts and Pure Compounds from Cinnamomum Genus. Molecules, 26(13), 3803.

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Antimicrobial Susceptibility of Candida and Bacteria to Terpenoids

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The antimicrobial susceptibility of C. albicans and bacterial isolates to terpenoidal compounds was determined using the broth microdilution method according to the Clinical and Laboratory Standards Institute (CLSI) for yeast [19 ] and bacteria [20 ]. Terpenoidal compounds including farnesol, carvacrol, and cuminaldehyde (Figure 1) and antimicrobial agents including amphotericin B, colistin, and vancomycin were purchased from Sigma Company.
C. albicans biofilm was developed according to well-established protocols [21 (link)]. Briefly, 200 µL RPMI-1640 containing 5 × 10⁵ cells/mL was incubated in polystyrene, round-bottomed, 96 well microtiter plates (Corning Inc., Corning, NY, USA) (Costar^®). Terpenoids were applied in the concentrations 1, 2, 3, and 4 mg/mL for cuminaldehyde, 0.25, 0.5, 1, 2 and 3 mg/mL for carvacrol, and 0.22 mg/mL to 66.7 mg/mL for farnesol [22 (link)]. The plates were then incubated at 37 °C for 4, 24, and 48 h time periods. The microbial growth was measured at OD₅₇₀ using a microplate reader (BioTekEL × 808, Agilent, Winooski, VT, USA). Clear wells with the lowest terpenoid concentrations and with no visible growth were considered to represent the minimum inhibitory concentration (MIC).
amphotericin B was employed as a positive control against C. albicans. Cultures without terpenoids or antimicrobial agents were employed as negative controls.

Touil H.F., Boucherit K., Boucherit-Otmani Z., Kohder G., Madkour M, & Soliman S.S. (2020). Optimum Inhibition of Amphotericin-B-Resistant Candida albicans Strain in Single- and Mixed-Species Biofilms by Candida and Non-Candida Terpenoids. Biomolecules, 10(2), 342.

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Monoterpene Fungicide Evaluation Protocol

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The examined monoterpenes (cuminaldehyde, linalool, and carvone) with a purity of 99% were obtained from Sigma Aldrich, St. Louis, MO, USA. A fungicide Toclophos-methyl + Thiram with a trade name of Rhizolex 50 WP was purchased from Sumitomo chemical company, Japan.

Derbalah A., Shebl A.M., Elgobashy S.F., Ahmad A.A., Ramadan N.E., Behiry S.I., Abdelkhalek A., Saleem M.H., Al-Askar A.A., Kamran M, & Elsharkawy M.M. (2022). Resistance Induction and Direct Antifungal Activity of Some Monoterpenes against Rhizoctonia solani, the Causal of Root Rot in Common Bean. Life, 12(7), 1040.

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Preparation of Analytical Standards

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Dichloromethane HiPerSolv (DCM) and sodium sulfate (Na 2 SO 4 ) were provided by VWR International GmbH (Darmstadt, Germany). DCM was freshly distilled prior to use. The analytical standards 1,8-cineole, linalool, cuminaldehyde, cinnamaldehyde, sotolone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, eugenol, vanillin and 𝛾-nonalactone were purchased from Sigma Aldrich (Steinheim, Germany). The isotopically labeled standards 2 H 3 -1,8-cineole, 2 H 4-5 -linalool, 2 H 8 -cuminaldehyde, 2 H 6cinnamaldehyde, 13 C 2 -sotolone, 13 C 2 -4-hydroxy-2,5-dimethyl-3(2H)-furanone, 2 H 3 -eugenol and 2 H 4 -𝛾-nonalactone were from aromaLAB GmbH (Martinsried, Germany) and 13 C 6 -vanillin from Sigma Aldrich.

Debong M.W., N'Diaye K., Owsienko D., Schöberl D., Ammar T., Lang R., Buettner A., Hofmann T, & Loos H.M. (2021). Dietary Linalool is Transferred into the Milk of Nursing Mothers. Molecular nutrition & food research, 65(23).

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