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Zanthoxylum limoncello is a native plant from southern Mexico which is used as a timber source, condiment and as a traditional medicine. Herein, we report on the volatile content of the leaf essential oil and its biological activities. The annual essential oils (2015-2018) contained volatile organic compounds which exhibited a moderate growth inhibitory activity against H. pylori ATCC 53504 (MIC 121.4-139.7 μg mL À 1 ), 26695 (MIC 85.5 -94.9 μg mL À 1 ) and J99 (MIC 94.7 -110.4 μg mL À 1 ). These hydrodistillates contained 2-undecanone (31.6-36.8 %; MIC 185.3 -199.2 μg mL À 1 ) and 2-undecenal (25.1-35.7 %; MIC 144.8 -111.3 μg mL À 1 ) as the most abundant compounds which were partially involved in the anti-H. pylori activity. The human ornithine decarboxylase enzyme (ODC1), which shows increased activity in several cancer types, was non-competitively inhibited (V max 2.7 > 0.8 K cat s À 1 ) by the essential oil of Z. limoncello as well as by 2-undecanone and 2-undecenal in accordance to in vitro kinetic studies. In silico calculations strongly suggest that the carbonyl group of these oxygenated hydrocarbons interacts with both Asn319 and Ala39 at the subunit A of ODC1. Considering that Ala39 is located close to Asn44, a crucial amino acid of the ODC's allosteric site, the non-competitive inhibition of the enzyme by 2-undecanone and 2-undecenal is endorsed. Finally, the essential oil of Z. limoncello and its main volatiles showed a significant (p < 0.01) and prolonged repellent effect against Aedes aegypti.[a] RI 1 , RI 2 , Retention index obtained with HP-5 ms and Factor Four VF5-ms, respectively. Abundances are presented as the average of five different samples (n = 5). [b] Indicates corroboration by co-injection with authentic standards.
Zanthoxylum limoncello is a native plant from southern Mexico which is used as a timber source, condiment and as a traditional medicine. Herein, we report on the volatile content of the leaf essential oil and its biological activities. The annual essential oils (2015-2018) contained volatile organic compounds which exhibited a moderate growth inhibitory activity against H. pylori ATCC 53504 (MIC 121.4-139.7 μg mL À 1 ), 26695 (MIC 85.5 -94.9 μg mL À 1 ) and J99 (MIC 94.7 -110.4 μg mL À 1 ). These hydrodistillates contained 2-undecanone (31.6-36.8 %; MIC 185.3 -199.2 μg mL À 1 ) and 2-undecenal (25.1-35.7 %; MIC 144.8 -111.3 μg mL À 1 ) as the most abundant compounds which were partially involved in the anti-H. pylori activity. The human ornithine decarboxylase enzyme (ODC1), which shows increased activity in several cancer types, was non-competitively inhibited (V max 2.7 > 0.8 K cat s À 1 ) by the essential oil of Z. limoncello as well as by 2-undecanone and 2-undecenal in accordance to in vitro kinetic studies. In silico calculations strongly suggest that the carbonyl group of these oxygenated hydrocarbons interacts with both Asn319 and Ala39 at the subunit A of ODC1. Considering that Ala39 is located close to Asn44, a crucial amino acid of the ODC's allosteric site, the non-competitive inhibition of the enzyme by 2-undecanone and 2-undecenal is endorsed. Finally, the essential oil of Z. limoncello and its main volatiles showed a significant (p < 0.01) and prolonged repellent effect against Aedes aegypti.[a] RI 1 , RI 2 , Retention index obtained with HP-5 ms and Factor Four VF5-ms, respectively. Abundances are presented as the average of five different samples (n = 5). [b] Indicates corroboration by co-injection with authentic standards.
The preparation of an unprecedented series of nucleobase modified 3-fluoro-2-(phosphonomethoxy)propyl (FPMP) acyclic nucleosides in both their (R) and (S) enantiomerically pure forms is described. The synthesis focuses on a Mitsunobu alkylation reaction to construct the CÀ N(9) bond between a chiral fluorinated side-chain residue and 6-or 7-modified guanine analogs. Prodrugs of FPMP-7-deazaguanine were also synthesized by derivatization of the corresponding phosphonic acid functionality with (bis)diamyl aspartate amidate groups, leading to moderate activity against human immunodeficiency virus type 1 (HIV-1). of such modification on the antiviral activity of the resulting FPMP derivatives as well as the efficiency of the key Mitsunobu alkylation. Figure 1. Examples of purine modified acyclic nucleoside analogs relevant to this study. Scheme 1. Synthesis of (R)/(S)-fluorinated acyclic phosphonate acids 5a/b. Reagents and conditions: a) Ph 3 P, DIAD, THF, r.t., 24 h; b) THF/H 2 O, reflux, 24 h; c) Et 3 N, DMF, 100°C, 4 h; d) TMSBr, 2,6-lutidine, MeCN, r.t., 12 h. Scheme 2. Synthesis of (R)/(S)-fluorinated acyclic phosphonate acids 11a/b and 14a/b. Reagents and conditions: a) PivCl, pyridine, r.t., 3 h; b) Selectfluor, MeCN, 50°C, 30 min; c) Ph 3 P, DIAD, 2a/b, THF, r.t., 24 h; d) (i) DABCO, K 2 CO 3 , dioxane/H 2 O, 90°C, 3 h; (ii) NH 3 / MeOH, r.t., 12 h; e) TMSBr, 2,6-lutidine, MeCN, r.t., 12 h.
In this study, 32 Salmonella strains isolated from 400 chicken carcasses were serotyped, and antibiotic resistance profiles were detected against 12 selected antimicrobial agents using disc diffusion method. Thirty-two isolates were identified as follows; 22 (68.7%) Salmonella Enteritidis, five (15.6%) Salmonella Virchow, three (9.3%) Salmonella Typhimurium and two (6.2%) Salmonella Hadar. In all Salmonella isolates, antibiotic resistance were detected. Out of 32 Salmonella strains, 22 (68.75%) displayed multi-drug resistance. Thirty-two (100.0%) of the isolates were found to be resistant to penicillin G, 20 (62.5%) to nalidixic acid, four (12.5%) to cephalothin, two (6.2%) to streptomycin and two (6.2%) to tetracycline. Fifteen (68.1%) Salmonella Enteritidis, one (33.3%) Salmonella Typhimurium, two (100.0%) Salmonella Hadar and two (40.0%) Salmonella Virchow were shown to be resistant to nalidixic acid. Cephalothin resistance was detected in 9.0%, 33.3%, and 20.0% for Salmonella Enteritidis, Salmonella Typhimurium and Salmonella Virchow, respectively. The results indicate that Salmonella recovered from chicken carcasses were resistant to multiple antimicrobials and that resistance among these isolates varies by serotype. Also, this emerged as a significant public health problem.
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