Technical-grade resveratrol (a.i. 99%), psoralen (98%), camptothecin (97%), reserpine (98%), and eugenol (99%) were purchased from Shanghai Maclean Biochemical Technology Co., LTD (Shanghai, China). Salicylic acid was provided by Beijing Solarbio Technology Co., LTD. Chalcone (97%) and anethene (99%) were obtained from Biochemical Technology Co., Ltd. (Shanghai, China). Flavanones (98%) and farnesol (mixture of isomers) (SG 0.89) were obtained from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). The fungicides and inhibitor of the alternative respiratory pathway used were azoxystrobin (98.0%, Syngenta Biotechnology, Shanghai), salicylhydroxamic acid (SHAM) (99%, Shanghai Marklin Biochemistry, China), boscalid (99%, BASF Corporation, Nanjing, China), fluazinam (98.4%, Ishihara Sangyo Kaisha Ltd., Japan), fludioxonil (97.9%, Syngenta Biotechnology, Co., Ltd, China), difenoconazole (98.4%, Yulong Chemical Industrial Co., Ltd., Hangzhou), pyrimethanil (93%, Jiangsu Limin Chemical Industrial Co., Ltd., China), and prochloraz (98%, Jiangsu Huifeng Agrochemical Co., Ltd., Dafeng, China), and all PSMs were dissolved in dimethyl sulfoxide (DMSO) to prepare a stock solution (1 × 105 µg/mL) and kept in darkness at −20°C.
Eugenol
Manufactured by Maclin Biochemical Technology
Sourced in China
Eugenol is a colorless to pale yellow liquid with a characteristic clove-like aroma. It is a naturally occurring phenolic compound found in certain essential oils, such as clove oil, cinnamon leaf oil, and bay leaf oil. Eugenol serves as a core functional component in various laboratory applications, including use as a flavoring agent, antiseptic, and topical anesthetic.
Automatically generated - may contain errors
Lab products found in correlation
Reserpine, by Maclin Biochemical Technology (18 mentions)
Salicylic acid, by Solarbio (3 mentions)
Boscalid, by BASF (3 mentions)
Methoxyamine hydrochloride, by Merck Group (3 mentions)
O bis trimethylsilyl trifluoroacetamide bstfa, by Merck Group (3 mentions)
Milli q system, by Merck Group (3 mentions)
Pyridine, by Merck Group (3 mentions)
Methanol, by Sinopharm (3 mentions)
Tween 20, by Solarbio (3 mentions)
Acetonitrile, by Sinopharm (3 mentions)
Cinnamaldehyde, by Maclin Biochemical Technology (2 mentions)
Resveratrol, by Maclin Biochemical Technology (1 mentions)
Protocatechuic acid, by Maclin Biochemical Technology (1 mentions)
Caffeic acid, by Maclin Biochemical Technology (1 mentions)
Butyric acid, by Maclin Biochemical Technology (1 mentions)
Ferulic acid, by Maclin Biochemical Technology (1 mentions)
K2co3, by Merck Group (1 mentions)
1220 infinity 2 lc, by Agilent Technologies (1 mentions)
N hydroxysuccinimide, by Yuanye Bio-Technology (1 mentions)
Benzoic acid, by Maclin Biochemical Technology (1 mentions)
10 protocols using eugenol
1
Bioactive Compounds and Fungicide Assays
2
Quantitative Analysis of Bioactive Compounds
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Tween 20 was purchased from Beijing Solarbio Science & Technology Co., Ltd. (Beijing, China). Methanol and acetonitrile of HPLC grade were purchased from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China). Pyridine, methoxyamine hydrochloride, N, and O-bis (trimethylsilyl) trifluoroacetamide (BSTFA) (containing 1% trimethylchlorosilane, TMS), all analytical-grade, were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ultrapure water was obtained from a Milli-Q system (Millipore, Billerica, MA, USA). Standards with concentrations of more than 99% were purchased from Sigma-Aldrich. Technical-grade resveratrol (a.i. 99%), reserpine (98%), and eugenol (99%) were purchased from Shanghai Maclean Biochemical Technology Co., Ltd. (Shanghai, China). Salicylic acid was provided by Beijing Soleibao Science & Technology Co., Ltd. (Beijing, China). Flavanone (98%) was obtained from Tokyo Chemical Industry Co. (Tokyo, Japan). All chemicals were dissolved in dimethyl sulfoxide (DMSO) to prepare a stock solution (1 × 105 µg/mL) and kept in darkness at −20 °C.
3
Antimicrobial Activity of Natural Compounds on Listeria
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The bacterial strain L. monocytogenes CMCC 54004 (Lm 54004, serotype 1/2a) was purchased from the China National Center for Medical Culture Collections (CMCC), source from Czech Institute of Epidemiology and Microbiology. The strain was stored at −80°C in the brain heart infusion (BHI; Beijing Land Bridge Technology, China) with 25% (v/v) glycerol. The strain was activated by transferring 0.2 ml of the frozen culture into 20 ml of BHI and incubating at 37°C for 18 h with two consecutive transfers.
Four natural antimicrobial compounds: cinnamaldehyde, eugenol, resveratrol, and thymoquinone were obtained from Macklin, China; Solarbio, China and Yuanyeshengwu, China respectively. The control compound, sodium hypochlorite (10% active chlorine), was obtained from Sinopharm Chemical Reagent, China. The purity of all the compounds was above 98%. The four natural compounds were diluted with 1% dimethyl sulfoxide (DMSO) in BHI, with 1% DMSO shown not to exhibit an adverse effect on the growth of L. monocytogenes (Fan et al., 2018 (link)).
Four natural antimicrobial compounds: cinnamaldehyde, eugenol, resveratrol, and thymoquinone were obtained from Macklin, China; Solarbio, China and Yuanyeshengwu, China respectively. The control compound, sodium hypochlorite (10% active chlorine), was obtained from Sinopharm Chemical Reagent, China. The purity of all the compounds was above 98%. The four natural compounds were diluted with 1% dimethyl sulfoxide (DMSO) in BHI, with 1% DMSO shown not to exhibit an adverse effect on the growth of L. monocytogenes (Fan et al., 2018 (link)).
4
Synthesis and Characterization of Bioactive Compounds
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GA, N-(3-bromopropyl) benzene diamine, butyric acid, protocatechuic acid, benzoic acid, caffeic acid, ferulic acid, eugenol, and gallicin were obtained from Macklin (Shanghai, China). N-Hydroxy succinimide (NHS) and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) were purchased from Yuanye (Shanghai, China). K2CO3, ethyl acetate, dimethylformamide (DMF), bovine serum albumin (BSA), and ovalbumin (OVA) were purchased from SIGMA. Ten 8-week SPF male mice were obtained from Vital River Laboratory Animal Technology (Beijing, China), license number SCXK (Beijing): 2021-0006; SP2/0 myeloma cells were purchased from Cell Center, Institute of Basic Medical Sciences, Chinese Academy of Medical Sciences.
HPLC was performed with 1220 infinityIILC (Agilent, Santa Clara, CA, USA). High-resolution mass spectrometry (HRMS) was carried out using Q Exactive Focus (Thermo Fisher, Waltham, MA, USA). UV spectrophotometer was recorded with UV-8000S (Metash, Shanghai, China). MALDI-TOF was recorded with Bruker Autoflex III (Bruker-Spectrospin AG, Karlsruhe, Germany).
HPLC was performed with 1220 infinityIILC (Agilent, Santa Clara, CA, USA). High-resolution mass spectrometry (HRMS) was carried out using Q Exactive Focus (Thermo Fisher, Waltham, MA, USA). UV spectrophotometer was recorded with UV-8000S (Metash, Shanghai, China). MALDI-TOF was recorded with Bruker Autoflex III (Bruker-Spectrospin AG, Karlsruhe, Germany).
5
Analytical Standards for Volatile Compounds
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All authentic standards with at least 95% purity, including 2-methyl-3-heptanone, 1,2-dichlorobenzene, benzaldehyde, methyl benzoate, ethyl benzoate, benzyl alcohol, methyleugenol, (E)-cinnamaldehyde, and (E)-cinnamic alcohol, were from Aladdin Co., Ltd. (Shanghai, China); (E)-2-hexenal, 4-allylphenol, benzyl acetate, (E)-cinnamyl acetate, eugenol, and benzyl benzoate were from MACKLIN Co., Ltd. (Shanghai, China). Methanol used to dilute standards was purchased from MREDA Scientific Co., Ltd. (Beijing, China). A mixture of C7–C40 n-alkane standard solution was from o2si (North Charleston, SC, USA).
6
Antimicrobial Potential of Eugenol
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The eugenol used in this study was obtained from Macklin Biochemical (Shanghai, China) Co., Ltd. Dimethyl sulfoxide (DMSO, Sigma-Aldrich, United States) was added with a final concentration of 1%. Triphenyltetrazolium chloride (TTC) was purchased from Biotopped Co., LTD (Beijing, China). K. pneumoniae ATCC 46117 and E. coli ATCC 25922 were kept in our laboratory. The clinical K. pneumoniae was isolated from nasal swabs and the feces sample of a porcine with respiratory disease was collected from a small pig farm in Gongzhuling City, Jilin province. Tryptone soybean broth (TSB) and Tryptone soybean agar (TSA) were obtained from Qingdao Hope Bio-Technology Co., LTD (Qingdao, China). Commercial antibiotic paper disks: AMO (Amoxicillin, 20 μg), AZM (Azithromycin, 15 μg), AZL (Azlocillin, 75 μg), AZT (Aztreonam, 30 μg), CFZ (Cefazolin, 30 μg), CHL (Chloramphenicol, 30 μg), CTX (Cefotaxime, 30 μg), DOX (Doxycycline, 30 μg), FRZ (furazolidone, 300 μg), GEN (gentamicin, 10 μg), IPM (imipenem, 10 μg), KAN (kanamycin, 30 μg), LVX (levofloxacin, 5 μg), OXA (oxacillin, 1 μg), NOR (Norfloxacin, 10 μg), POL (PolymyxinB, 300IU), STR (Streptomycin, 10 μg) were purchased from Hangzhou Microbial Reagent Co., Ltd (Hangzhou, China). S-adenosylhomocysteine (SAH) and DTNB were purchased from Sigma-Aldrich, Inc. (United States).
7
Antimicrobial Activity Screening Protocol
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Hesperetic acid, 2-hydroxybenzene-1,4-dicarboxylic acid (2-HTPA), thymol, carvacrol, eugenol, cinnamaldehyde, salicylic acid, trans-cinnamic acid, and trans-ferulic acid, as well as ethanol were purchased from Shanghai Macklin Biochemical Co., Ltd. Tween 80 was supplied by Beijing Solarbio Science & Technology Co., Ltd. LB broth was purchased from Beijing Aoboxing Bio-tech Co., Ltd. S. aureus 186335 was obtained from Beijing Beina Chuanglian Biotechnology Institute. Bacillus subtilis CMCC63501 (B. subtilis), Pseudomonas aeruginosa ATCC27853 (P. aeruginosa), and Escherichia coli ATCC25922 (E. coli) were purchased from Beijing Solarbio Science & Technology Co., Ltd.
8
Temporal Profiling of S. chinensis Fruit
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Plant samples were collected in the Beijing medicinal plant garden at the Institute of Medicinal Plant Development (IMPLAD) (40°N and 116°E) in Beijing, and were authenticated as S. chinensis by Professor Bengang Zhang of IMPLAD. After entering the fruiting period, we regularly picked SCF with three biological replicates at 20, 50, 80, and 110 days (abbreviation: S1, S2, S3, and S4) after fluorescence (Supplementary Fig. 1 ). The samples were immediately frozen in liquid nitrogen and stored at −80 °C until RNA extraction. Ethyl acetate of UPLC grade was purchased from Merck (Merck KGaA, Darmstadt, Germany). Reference compounds such as eugenol and coniferyl alcohol were purchased from Macklin Biochemical (Shanghai, China). Isoeugenol was obtained from Chengdu DeSiTe Biological Technology (Chengdu, China).
9
Antimicrobial Assessment of Eugenol
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Eugenol was obtained from Macklin Biochemical (Shanghai, China) Co.,Ltd. and was dissolved in MH broth. Dimethyl sulfoxide (DMSO, Sigma–Aldrich, USA) was added with a final concentration of 1%. Triphenyltetrazolium chloride (TTC) was purchased from Biotopped Co., LTD (Beijing, China). Colistin was purchased from National Institutes for Food and Drug Control (Beijing, China). Mueller–Hinton broth (MHB) and Mueller–Hinton agar (MHA) were obtained from Qingdao Hope Bio-Technology Co., LTD (Qingdao, China). Lysogeny broth (LB) from Sangon Biotech (Shanghai, China) Co., Ltd. Commercial antibiotic paper disks: AMP(Ampicillin,10 μg), AZM(Azithromycin,15 μg), CFZ(Cefazolin,30 μg), CTX(Cefotaxime,30 μg), DOX(Doxycycline,30 μg), FF(Florfenicol,30 μg), FRZ(furazolidone,300 μg), GEN(gentamicin,10 μg), KAN(kanamycin,30 μg), LVX(levofloxacin,5 μg), NEO(Neomycin,30 μg), NOR(Norfloxacin,10 μg), POL(PolymyxinB,300 IU), STR(Streptomycin,10 μg), TCY(Tetracycline,30 μg) were purchased from Hangzhou Microbial Reagent Co.,Ltd. (Hangzhou, China).
10
Floral Compound Preparation and Evaluation
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Benzaldehyde (98.5%) was purchased from Sinopharm Chemical Reagent Co., Ltd., (Shanghai, China). Myrcene (90%), trans-β-caryophyllene (80%), cis-3-hexen-1-ol (98%), linalool (98%), eugenol (99%), benzyl alcohol (99.5%), 2-ethyl-p-xylene (98%), α-terpineol (98%) and cis-11-hexadecenal (95%) were purchased from Shanghai Macklin Biochemical Co. Ltd. (China), and methyl salicylate (99.5%) was purchased from Tianjin Beilian Fine Chemicals Development Co., Ltd. (China). Hexane was purchased from Merck KGaA (Darmstadt, Germany).
To facilitate the experiment, the compounds we selected were common floral substances. It was difficult to generate an antennal reaction when the concentration of most compounds was lower than 1 mg L−1; we therefore set the minimum test concentration of the artificial solution to 1 mg L−1.
The Benzaldehyde solution was configured with Hexane as solvent and was divided into seven concentration gradients, i.e., 100, 50, 20, 10, 5, 2 and 1 mg L−1.
A mixture of cis-3-hexen-1-ol, myrcene, linalool, methyl salicylate, and trans-β-caryophyllene was prepared using Hexane as the solvent, at a concentration gradient similar to the above.
Helicoverpa armigera lures were purchased from Pherobio Technology Co., Ltd. (China).
To facilitate the experiment, the compounds we selected were common floral substances. It was difficult to generate an antennal reaction when the concentration of most compounds was lower than 1 mg L−1; we therefore set the minimum test concentration of the artificial solution to 1 mg L−1.
The Benzaldehyde solution was configured with Hexane as solvent and was divided into seven concentration gradients, i.e., 100, 50, 20, 10, 5, 2 and 1 mg L−1.
A mixture of cis-3-hexen-1-ol, myrcene, linalool, methyl salicylate, and trans-β-caryophyllene was prepared using Hexane as the solvent, at a concentration gradient similar to the above.
Helicoverpa armigera lures were purchased from Pherobio Technology Co., Ltd. (China).
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