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1.
Mol Plant Pathol ; 25(8): e13467, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-39099210

RESUMEN

Ralstonia solanacearum species complex (RSSC) includes soilborne bacterial plant pathogens with worldwide distribution and wide host ranges. Virulence factors are regulated via four hierarchically organized cell-cell contact independent quorum-sensing (QS) signalling systems: the Phc, which uses as signals (R)-methyl 3-hydroxypalmitate [(R)-3-OH PAME] or (R)-methyl 3-hydroxymyristate [(R)-3-OH MAME], the N-acyl homoserine lactone (AHL)-dependent RasI/R and SolI/R systems, and the recently identified anthranilic acid-dependent system. The unique Phc QS system has been extensively studied; however, the role of the two AHL QS systems has only recently been addressed. In this microreview, we present and discuss current data of the SolI/R and RasI/R QS systems in the RSSC. We also present the distribution and frequency of these AHL QS systems in the RSSC, discuss possible ecological roles and evolutive implications. The complex QS hierarchical networks emphasizes the crucial role of cell-cell signalling in the virulence of the RSSC.


Asunto(s)
Acil-Butirolactonas , Percepción de Quorum , Ralstonia solanacearum , Transducción de Señal , Ralstonia solanacearum/patogenicidad , Ralstonia solanacearum/metabolismo , Ralstonia solanacearum/fisiología , Acil-Butirolactonas/metabolismo , 4-Butirolactona/análogos & derivados , 4-Butirolactona/metabolismo
2.
J Agric Food Chem ; 72(33): 18423-18433, 2024 Aug 21.
Artículo en Inglés | MEDLINE | ID: mdl-39106460

RESUMEN

Natural products are a valuable resource for the discovery of novel crop protection agents. A series of γ-butyrolactone derivatives, derived from the simplification of podophyllotoxin's structure, were synthesized and assessed for their efficacy against tobacco mosaic virus (TMV). Several derivatives exhibited notable antiviral properties, with compound 3g demonstrating the most potent in vivo anti-TMV activity. At 500 µg/mL, compound 3g achieved an inactivation effect of 87.8%, a protective effect of 71.7%, and a curative effect of 67.7%, surpassing the effectiveness of the commercial plant virucides ningnanmycin and ribavirin. Notably, the syn-diastereomer (syn-3g) exhibited superior antiviral activity compared to the anti-diastereomer (anti-3g). Mechanistic studies revealed that syn-3g could bind to the TMV coat protein and interfere with the self-assembly process of TMV particles. These findings indicate that compound 3g, with its simple chemical structure, could be a potential candidate for the development of novel antiviral agents for crop protection.


Asunto(s)
4-Butirolactona , Antivirales , Nicotiana , Enfermedades de las Plantas , Podofilotoxina , Virus del Mosaico del Tabaco , Virus del Mosaico del Tabaco/efectos de los fármacos , Podofilotoxina/química , Podofilotoxina/farmacología , Antivirales/farmacología , Antivirales/química , 4-Butirolactona/análogos & derivados , 4-Butirolactona/química , 4-Butirolactona/farmacología , Enfermedades de las Plantas/virología , Enfermedades de las Plantas/prevención & control , Nicotiana/química , Nicotiana/virología , Relación Estructura-Actividad , Estructura Molecular , Protección de Cultivos
3.
Org Lett ; 26(30): 6320-6323, 2024 Aug 02.
Artículo en Inglés | MEDLINE | ID: mdl-39046190

RESUMEN

Herein, we present a highly efficient method for constructing the intricate 5-5-6 fused ring system commonly found in the polycyclic furanobutenolide-derived cembranoid and norcembranoid natural product family with remarkable diastereoselectivity, utilizing an intramolecular Diels-Alder reaction as the cornerstone. Notably, employing a propargyl ether tether as the dienophile yields significant enhancements in the transformation process compared to its propargyl ester counterpart, as demonstrated in our previous total synthesis of havellockate. This advancement holds promising implications for future investigations, offering a streamlined pathway for rapidly assembling the tricyclic core characteristic of this diverse family of natural products.


Asunto(s)
Diterpenos , 4-Butirolactona/química , 4-Butirolactona/análogos & derivados , 4-Butirolactona/síntesis química , Productos Biológicos/química , Productos Biológicos/síntesis química , Reacción de Cicloadición , Diterpenos/química , Diterpenos/síntesis química , Furanos/química , Furanos/síntesis química , Estructura Molecular , Estereoisomerismo
4.
Appl Microbiol Biotechnol ; 108(1): 418, 2024 Jul 16.
Artículo en Inglés | MEDLINE | ID: mdl-39012538

RESUMEN

Pseudomonas aeruginosa (P. aeruginosa) biofilm formation is a crucial cause of enhanced antibiotic resistance. Quorum sensing (QS) is involved in regulating biofilm formation; QS inhibitors block the QS signaling pathway as a new strategy to address bacterial resistance. This study investigated the potential and mechanism of L-HSL (N-(3-cyclic butyrolactone)-4-trifluorophenylacetamide) as a QS inhibitor for P. aeruginosa. The results showed that L-HSL effectively inhibited the biofilm formation and dispersed the pre-formed biofilm of P. aeruginosa. The production of extracellular polysaccharides and the motility ability of P. aeruginosa were suppressed by L-HSL. C. elegans infection experiment showed that L-HSL was non-toxic and provided protection to C. elegans against P. aeruginosa infection. Transcriptomic analysis revealed that L-HSL downregulated genes related to QS pathways and biofilm formation. L-HSL exhibits a promising potential as a therapeutic drug for P. aeruginosa infection. KEY POINTS: • Chemical synthesis of N-(3-cyclic butyrolactone)-4-trifluorophenylacetamide, named L-HSL. • L-HSL does not generate survival pressure on the growth of P. aeruginosa and can inhibit the QS system. • KEGG enrichment analysis found that after L-HSL treatment, QS-related genes were downregulated.


Asunto(s)
4-Butirolactona , Biopelículas , Caenorhabditis elegans , Pseudomonas aeruginosa , Percepción de Quorum , Pseudomonas aeruginosa/efectos de los fármacos , Pseudomonas aeruginosa/fisiología , Pseudomonas aeruginosa/genética , Biopelículas/efectos de los fármacos , Biopelículas/crecimiento & desarrollo , Percepción de Quorum/efectos de los fármacos , Caenorhabditis elegans/efectos de los fármacos , Caenorhabditis elegans/microbiología , Animales , 4-Butirolactona/análogos & derivados , 4-Butirolactona/farmacología , 4-Butirolactona/metabolismo , Antibacterianos/farmacología , Perfilación de la Expresión Génica , Homoserina/análogos & derivados , Homoserina/metabolismo , Homoserina/farmacología , Regulación Bacteriana de la Expresión Génica/efectos de los fármacos
5.
Mikrobiyol Bul ; 58(3): 225-238, 2024 Jul.
Artículo en Turco | MEDLINE | ID: mdl-39046206

RESUMEN

In recent years, as the paradigm of communication between cells has been clarified, the ability of bacteria to change their gene expression patterns in response to various extracellular signals has attracted great interest. In particular, intracellular and intercellular communication between bacterial populations, called quorum sensing (QS), is essential for coordinating physiological and genetic activities. QS studies are critical, particularly in elucidating the regulatory mechanisms of infectious processes in food-borne pathogens. Elucidating the QS mechanisms in Salmonella is effective in silencing the virulence factors in the fight against this bacterium. The aims of this study were; to create luxS gene mutants that play a vital role in the QS activity of Salmonella and to determine the effect of this mutation on the expression of virulence genes in the bacteria and to determine the impact of synthetic N-hexanoyl-homoserine lactone (C6HSL) on biofilm formation and AI-2 signaling pathway of Salmonella wild strain and luxS gene mutants. luxS gene mutants were constructed by recombining the gene region with the chloramphenicol gene cassette based on homologous region recombination. In the luxS mutants obtained in this way, the expression of eight different virulence genes (hilA, invA, inv, glgC, fimF, fliF, lpfA, gyrA), which have essential roles in Salmonella pathogenicity, was determined by quantitative real-time reverse transcriptase polymerase chain reaction (rRT-qPCR) method and compared with natural strains. As a result of these studies, it was determined that the expression of each gene examined was significantly reduced in luxS mutant strains. The relative AI-2 activities of Salmonella strains were analyzed depending on time. It was determined that the highest activity occurred at the fourth hour and the AI-2 activities of luxS mutants were reduced compared to the wild strain. Finally, it was determined that C6HSL increased the biofilm activity of Salmonella Typhimurium DMC4, SL1344 wild strains, and mutants, mainly at the 72nd hour. In conclusion, our results proved that C6HSL stimulated QS communication in all strains and increased biofilm of Salmonella formation and autoinducer activity. This situation determines that Salmonella responds to external signals by using QS systems. In addition, this research contributed to provide additional information on interspecies communication mechanisms to develop strategies to prevent biofilm formation of this pathogen.


Asunto(s)
Proteínas Bacterianas , Biopelículas , Liasas de Carbono-Azufre , Regulación Bacteriana de la Expresión Génica , Homoserina , Percepción de Quorum , Biopelículas/crecimiento & desarrollo , Liasas de Carbono-Azufre/genética , Virulencia , Proteínas Bacterianas/genética , Proteínas Bacterianas/metabolismo , Homoserina/análogos & derivados , Mutación , Factores de Virulencia/genética , 4-Butirolactona/análogos & derivados , 4-Butirolactona/metabolismo , Animales , Salmonella/patogenicidad , Salmonella/genética
6.
J Agric Food Chem ; 72(31): 17306-17316, 2024 Aug 07.
Artículo en Inglés | MEDLINE | ID: mdl-39054269

RESUMEN

Overexpression of carboxyl/cholinesterase (CCE) genes has been reported to be associated with many cases of pesticide resistance in arthropods. However, it has been rarely documented that CCE genes participate in spirodiclofen resistance in Panonychus citri. In previous research, we found that spirodiclofen resistance is related to increased P450 and CCE enzyme activities in P. citri. In this study, we identified two CCE genes, PcCCE3 and PcCCE5, which were significantly upregulated in spirodiclofen-resistant strain and after exposure to spirodiclofen. RNA interference of PcCCE3 and PcCCE5 increased the spirodiclofen susceptibility in P. citri. In vitro metabolism indicated that PcCCE3 and PcCCE5 could interact with spirodiclofen, but metabolites were detected only in the PcCCE3 treatment. Our results indicated that PcCCE3 participates in spirodiclofen resistance through direct metabolism, and PcCCE5 may be involved in the spirodiclofen resistance by passive binding and sequestration, which provides new insights into spirodiclofen resistance in P. citri.


Asunto(s)
Proteínas de Artrópodos , Compuestos de Espiro , Animales , Compuestos de Espiro/farmacología , Compuestos de Espiro/metabolismo , Compuestos de Espiro/química , Proteínas de Artrópodos/genética , Proteínas de Artrópodos/metabolismo , Proteínas de Artrópodos/química , Resistencia a Medicamentos/genética , Carboxilesterasa/genética , Carboxilesterasa/metabolismo , 4-Butirolactona/análogos & derivados , 4-Butirolactona/metabolismo , 4-Butirolactona/farmacología
7.
J Agric Food Chem ; 72(28): 15474-15486, 2024 Jul 17.
Artículo en Inglés | MEDLINE | ID: mdl-38949855

RESUMEN

Corn ear rot and fumonisin caused by Fusarium verticillioides pose a serious threat to food security. To find more highly active fungicidal and antitoxic candidates with structure diversity based on naturally occurring lead xanthatin, a series of novel spiropiperidinyl-α-methylene-γ-butyrolactones were rationally designed and synthesized. The in vitro bioassay results indicated that compound 7c showed broad-spectrum in vitro activity with EC50 values falling from 3.51 to 24.10 µg/mL against Rhizoctonia solani and Alternaria solani, which was more active than the positive controls xanthatin and oxathiapiprolin. In addition, compound 7c also showed good antitoxic efficacy against fumonisin with a 48% inhibition rate even at a concentration of 20 µg/mL. Fluorescence quenching and the molecular docking validated both 7c and oxathiapiprolin targeting at FvoshC. RNA sequencing analysis discovered that FUM gene cluster and protein processing in endoplasmic reticulum were downregulated. Our studies have discovered spiropiperidinyl-α-methylene-γ-butyrolactone as a novel FvoshC target-based scaffold for fungicide lead with antitoxin activity.


Asunto(s)
Alternaria , Fungicidas Industriales , Fusarium , Simulación del Acoplamiento Molecular , Rhizoctonia , Fungicidas Industriales/farmacología , Fungicidas Industriales/química , Fungicidas Industriales/síntesis química , Alternaria/efectos de los fármacos , Fusarium/efectos de los fármacos , Rhizoctonia/efectos de los fármacos , Relación Estructura-Actividad , Enfermedades de las Plantas/microbiología , 4-Butirolactona/análogos & derivados , 4-Butirolactona/química , 4-Butirolactona/farmacología , Proteínas Fúngicas/química , Proteínas Fúngicas/genética , Proteínas Fúngicas/metabolismo , Receptores de Esteroides/metabolismo , Receptores de Esteroides/genética , Receptores de Esteroides/química , Descubrimiento de Drogas , Zea mays/química , Zea mays/microbiología , Estructura Molecular
8.
Fitoterapia ; 177: 106104, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38950637

RESUMEN

Four undescribed polyketides, beshanzones A (1) and B (2) as well as beshanhexanols A (3) and B (4), along with three known ones (5-7) were isolated from the rice fermentation of two endophytic fungi associated with the critically endangered Chinese endemic conifer Abies beshanzuensis. γ-Butyrolactone derivatives 1, 2, and 5 were isolated from Phomopsis sp. BSZ-AZ-2, an interesting strain that drawn our attention this time. The cyclohexanol derivatives 3, 4, 6, and 7 were obtained during a follow-up investigation on Penicillium commune BSZ-P-4-1. The chemical structures including absolute configurations of compounds 1-4 were determined by spectroscopic methods, Mo2(OAc)4 induced electronic circular dichroism (IECD), GIAO NMR calculations and DP4+ probability analyses. In particular, compound 2 contains a novel 5/5 bicyclic ring system, which might be biogenetically derived from the known compound 5 through hydrolysis followed by an Aldol reaction. All isolates were evaluated for their antimicrobial activities against a small panel of bacterial and fungal pathogens. Compounds 6 and 7 showed moderate inhibitory activities against Candida albicans, with MIC values of 16 and 32 µg/mL, respectively.


Asunto(s)
Abies , Especies en Peligro de Extinción , Endófitos , Policétidos , Endófitos/química , Policétidos/farmacología , Policétidos/aislamiento & purificación , Policétidos/química , Estructura Molecular , China , Abies/química , Phomopsis/química , Pruebas de Sensibilidad Microbiana , Penicillium/química , Bacterias/efectos de los fármacos , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , 4-Butirolactona/análogos & derivados , 4-Butirolactona/aislamiento & purificación , 4-Butirolactona/farmacología , 4-Butirolactona/química
9.
Int J Med Mushrooms ; 26(8): 41-57, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38967210

RESUMEN

Bone metastasis in metastatic breast cancer commonly results in osteolytic lesions due to osteoclast activity, promoting bone destruction and tumor progression. The bioactive fungal isolates, 4-acetyl-antroquinonol B (4-AAQB) and erinacine A, have diverse pharmacological and biological activities. However, their effects on breast cancer bone metastasis treatment remain unclear. Our study aimed to examine the impact of 4-AAQB or erinacine A on breast cancer metastases in bone. The effects of 4-AAQB and erinacine A on breast cancer-induced osteoclastogenesis, breast cancer migration, production of prometastatic cytokine (TGF-ß) and marker (MMP-9), as well as potential MAPK signaling transductions were assessed. The results revealed that 4-AAQB and erinacine A effectively suppressed breast cancer-induced osteoclastogenesis and migration, and reduced TGF-ß and MMP-9 production via Erk or JNK signaling transductions, specifically in breast cancer cells or in breast cancer cells-induced osteoclasts. Based on these findings, either 4-AAQB or erinacine A showed promise in preventing breast cancer metastases in bone.


Asunto(s)
Neoplasias de la Mama , Metaloproteinasa 9 de la Matriz , Osteoclastos , Osteogénesis , Neoplasias de la Mama/tratamiento farmacológico , Neoplasias de la Mama/patología , Humanos , Femenino , Osteoclastos/efectos de los fármacos , Osteogénesis/efectos de los fármacos , Metaloproteinasa 9 de la Matriz/metabolismo , Metaloproteinasa 9 de la Matriz/genética , Línea Celular Tumoral , Movimiento Celular/efectos de los fármacos , Animales , Factor de Crecimiento Transformador beta/metabolismo , Neoplasias Óseas/secundario , Neoplasias Óseas/tratamiento farmacológico , Ratones , Sistema de Señalización de MAP Quinasas/efectos de los fármacos , Ciclohexanonas , 4-Butirolactona/análogos & derivados
10.
Environ Sci Pollut Res Int ; 31(31): 43927-43940, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38913262

RESUMEN

The caterpillar Anticarsia gemmatalis (Lepidoptera: Noctuidae) is a prevalent pest in soybean plantations, managed using both natural and synthetic chemical products. However, the emergence of resistance in some populations emphasizes the need to explore alternative insecticides. Flupyradifurone, a neurotoxic insecticide, has not been previously used for controlling A. gemmatalis. This study evaluated the potential of flupyradifurone in the management of A. gemmatalis. Initially, the toxicity and anti-feeding effects, as well as histopathological and cytotoxic impacts, of flupyradifurone on A. gemmatalis were evaluated. Subsequently, the indirect effects of flupyradifurone on the midgut and fat body of the predator Podisus nigrispinus (Hemiptera: Pentatomidae) were verified. The results indicate the susceptibility of caterpillars to flupyradifurone, with an LC50 of 5.10 g L-1. Furthermore, the insecticide adversely affects survival, induces an anti-feeding response, and inflicts damage on the midgut of the caterpillars. However, flupyradifurone also leads to side effects in the predator P. nigrispinus through indirect intoxication of the caterpillars, including midgut and fat body damage. While flupyradifurone demonstrates toxicity to A. gemmatalis, suggesting its potential for the chemical control of this pest, the indirect negative effects on the predator indicate the need for its controlled use in integrated pest management programs with the insecticide and the predator.


Asunto(s)
Insecticidas , Animales , Insecticidas/toxicidad , Larva/efectos de los fármacos , 4-Butirolactona/análogos & derivados , 4-Butirolactona/toxicidad , Heterópteros/efectos de los fármacos , Mariposas Nocturnas/efectos de los fármacos , Lepidópteros/efectos de los fármacos , Piridinas
11.
Food Funct ; 15(14): 7305-7313, 2024 Jul 15.
Artículo en Inglés | MEDLINE | ID: mdl-38874113

RESUMEN

Aims: Plant-derived lignans may protect against obesity, while their bioactivity needs gut microbial conversion to enterolignans. We used repeated measures to identify enterolignan-predicting microbial species and investigate whether enterolignans and enterolignan-predicting microbial species are associated with obesity. Methods: Urinary enterolignans, fecal microbiota, body weight, height, and circumferences of the waist (WC) and hips (HC) were repeatedly measured at the baseline and after 1 year in 305 community-dwelling adults in Huoshan, China. Body composition and liver fat [indicated by the controlled attenuation parameter (CAP)] were measured after 1 year. Multivariate-adjusted linear models and linear mixed-effects models were used to analyze single and repeated measurements, respectively. Results: Enterolactone and enterodiol levels were both inversely associated with the waist-to-hip ratio, body fat mass (BFM), visceral fat level (VFL), and liver fat accumulation (all P < 0.05). Enterolactone levels were also associated with lower WC (ß = -0.0035 and P = 0.013) and HC (ß = -0.0028 and P = 0.044). We identified multiple bacterial genera whose relative abundance was positively associated with the levels of enterolactone (26 genera) and enterodiol (22 genera, all P false discovery rate < 0.05), and constructed the enterolactone-predicting microbial score and enterodiol-predicting microbial score to reflect the overall enterolignan-producing potential of the host gut microbiota. Both these scores were associated with lower body weight and CAP (all P < 0.05). The enterolactone-predicting microbial score was also inversely associated with the BFM (ß = -0.1128 and P = 0.027) and VFL (ß = -0.1265 and P = 0.044). Conclusion: Our findings support that modulating the host gut microbiome could be a potential strategy to prevent obesity by enhancing the production of enterolignans.


Asunto(s)
Microbioma Gastrointestinal , Lignanos , Obesidad , Humanos , Lignanos/orina , Masculino , Femenino , Adulto , Persona de Mediana Edad , Obesidad/microbiología , Obesidad/metabolismo , Obesidad/orina , China , Bacterias/clasificación , Bacterias/metabolismo , Bacterias/aislamiento & purificación , Heces/microbiología , Biomarcadores/orina , 4-Butirolactona/análogos & derivados , 4-Butirolactona/orina , 4-Butirolactona/metabolismo , Hígado/metabolismo
12.
Int J Biol Macromol ; 274(Pt 2): 133048, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38857734

RESUMEN

Epiisopiloturine (EPI) is a compound found in jaborandi leaves with antiparasitic activity, which can be enhanced when incorporated into nanoparticles (NP). Cashew Gum (CG), modified by carboxymethylation, is used to produce polymeric nanomaterials with biological activity. In this study, we investigated the antimicrobial potential of carboxymethylated CG (CCG) NP containing EPI (NPCCGE) and without the alkaloid (NPCCG) against bacteria and parasites of the genus Leishmania. We conducted theoretical studies, carboxymethylated CG, synthesized NP by nanoprecipitation, characterized them, and tested them in vitro. Theoretical studies confirmed the stability of modified carbohydrates and showed that the EPI-4A30 complex had the best interaction energy (-8.47 kcal/mol). CCG was confirmed by FT-IR and presented DSabs of 0.23. NPCCG and NPCCGE had average sizes of 221.94 ± 144.086 nm and 247.36 ± 3.827 nm, respectively, with homogeneous distribution and uniform surfaces. No NP showed antibacterial activity or cytotoxicity to macrophages. NPCCGE demonstrated antileishmanial activity against L. amazonensis, both in promastigote forms (IC50 = 9.52 µg/mL, SI = 42.01) and axenic amastigote forms (EC50 = 6.6 µg/mL, SI = 60.60). The results suggest that nanostructuring EPI in CCG enhances its antileishmanial activity.


Asunto(s)
Anacardium , Antiinfecciosos , Nanopartículas , Gomas de Plantas , Anacardium/química , Nanopartículas/química , Gomas de Plantas/química , Antiinfecciosos/farmacología , Antiinfecciosos/química , Animales , Ratones , Leishmania/efectos de los fármacos , Simulación por Computador , Imidazoles , 4-Butirolactona/análogos & derivados
13.
Pestic Biochem Physiol ; 202: 105952, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38879306

RESUMEN

The citrus red mite, Panonychus citri, is one of the most notorious and devastating citrus pests around the world that has developed resistance to multiple chemical acaricides. In previous research, we found that spirodiclofen-resistant is related to overexpression of P450, CCE, and ABC transporter genes in P. citri. However, the regulatory mechanisms of these detoxification genes are still elusive. This study identified all hormone receptor 96 genes of P. citri. 8 PcHR96 genes contained highly conserved domains. The expression profiles showed that PcHR96h was significantly upregulated in spirodiclofen resistant strain and after exposure to spirodiclofen. RNA interference of PcHR96h decreased expression of detoxification genes and increased spirodiclofen susceptibility in P. citri. Furthermore, molecular docking, heterologous expression, and drug affinity responsive target stability demonstrated that PcHR96h can interact with spirodiclofen in vitro. Our research results indicate that PcHR96h plays an important role in regulating spirodiclofen susceptibility and provides theoretical support for the resistance management of P. citri.


Asunto(s)
Compuestos de Espiro , Animales , Compuestos de Espiro/farmacología , Compuestos de Espiro/metabolismo , Acaricidas/farmacología , Propionatos/farmacología , Propionatos/metabolismo , Tetranychidae/efectos de los fármacos , Tetranychidae/genética , Tetranychidae/metabolismo , Simulación del Acoplamiento Molecular , Proteínas de Artrópodos/genética , Proteínas de Artrópodos/metabolismo , Resistencia a Medicamentos/genética , 4-Butirolactona/análogos & derivados
14.
Food Chem ; 457: 140077, 2024 Nov 01.
Artículo en Inglés | MEDLINE | ID: mdl-38905833

RESUMEN

Human intestinal microbiota plays a crucial role in converting secoisolariciresinol diglucoside, a lignan found in flaxseed, to enterodiol, which has a range of health benefits: antioxidative, antitumor, and estrogenic/anti-estrogenic effects. Given the high secoisolariciresinol diglucoside content in flaxseed cake, this study investigated the potential of co-fermenting flaxseed cake with fermented soybean product to isolate bacterial strains that effectively convert secoisolariciresinol diglucoside to enterodiol in a controlled environment (in vitro). The co-fermentation process with stinky tofu microbiota significantly altered the lignan, generating 12 intermediate lignan metabolites as identified by targeted metabolomics. One particular promising strain, ZB26, demonstrated an impressive ability to convert secoisolariciresinol diglucoside. It achieved a conversion rate of 87.42 ± 0.33%, with secoisolariciresinol and enterodiol generation rates of 94.22 ± 0.51% and 2.91 ± 0.03%, respectively. Further optimization revealed, under specific conditions (0.5 mM secoisolariciresinol diglucoside, pH 8, 30 °C for 3 days), ZB26 could convert an even higher percentage (97.75 ± 0.05%) of the secoisolariciresinol diglucoside to generate secoisolariciresinol (103.02 ± 0.16%) and enterodiol (3.18 ± 0.31%). These findings suggest that the identified strains ZB26 have promising potential for developing functional foods and ingredients enriched with lignans.


Asunto(s)
Butileno Glicoles , Enterococcus faecium , Fermentación , Lino , Glucósidos , Lignanos , Lignanos/metabolismo , Lignanos/química , Lino/química , Lino/metabolismo , Lino/microbiología , Butileno Glicoles/metabolismo , Glucósidos/metabolismo , Glucósidos/química , Enterococcus faecium/metabolismo , Alimentos de Soja/análisis , Alimentos de Soja/microbiología , Biotransformación , Microbiota , Humanos , 4-Butirolactona/análogos & derivados , 4-Butirolactona/metabolismo
15.
J Econ Entomol ; 117(4): 1606-1615, 2024 Aug 12.
Artículo en Inglés | MEDLINE | ID: mdl-38748560

RESUMEN

Bemisia tabaci Middle East-Asia Minor 1 (MEAM1) is a significant pest that damages a wide range of high-value vegetable crops in south Florida. This pest has demonstrated the ability to develop resistance to various insecticide groups worldwide. Monitoring the resistance levels of MEAM1 populations and maintaining baseline susceptibility data are crucial for the long-term effectiveness of insecticide management strategies. We conducted serial dilution bioassays on 15 field populations of MEAM1 collected in south Florida to assess their resistance to 4 key insecticides: afidopyropen, cyantraniliprole, dinotefuran, and flupyradifurone. To quantify resistance levels, resistance ratios (RR) were generated by comparing the LC50 values of field populations to those of a known susceptible MEAM1 colony reared in the laboratory. Our findings reveal that all field-collected populations were susceptible to dinotefuran (RR 1-8) and flupyradifurone (RR 2-8). While over 80% of the populations tested were susceptible to afidopyropen (RR 1-9), 2 populations exhibited low (RR 38) and moderate resistance (RR 51), respectively. In contrast, most of the populations (57%) showed low to moderate resistance to cyantraniliprole (RR 21-78), and the remaining populations were susceptible (RR 3-10). The 2 populations with resistance to afidopyropen also exhibited moderate resistance to cyantraniliprole. Further research in this direction can aid in refining insecticide resistance management programs in Florida and other regions where B. tabaci MEAM1 is a major pest. Exploring the implications of these findings will be essential for insecticide use and integrated pest management strategies in south Florida.


Asunto(s)
Hemípteros , Resistencia a los Insecticidas , Insecticidas , Neonicotinoides , Nitrocompuestos , Pirazoles , Animales , Insecticidas/farmacología , Florida , Pirazoles/farmacología , Guanidinas/farmacología , 4-Butirolactona/análogos & derivados , Verduras , ortoaminobenzoatos/farmacología , Piridinas
16.
Macromol Rapid Commun ; 45(14): e2400091, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38690992

RESUMEN

Within bioplastics, natural poly(3-hydroxybutyrate) (PHB) stands out as fully biocompatible and biodegradable, even in marine environments; however, its high isotacticity and crystallinity limits its mechanical properties and hence its applications. PHB can also be synthesized with different tacticities via a catalytic ring-opening polymerization (ROP) of rac-ß-butyrolactone (BBL), paving the way to PHB with better thermomechanical and processability properties. In this work, the catalyst family is extended based on aluminum phenoxy-imine methyl catalyst [AlMeL2], that reveals efficient in the ROP of BBL, to the halogeno analogous complex [AlClL2]. As well, the impact on the ROP mechanism of different initiators is further explored with a particular focus in dimethylaminopyridine (DMAP), a hardly studied initiator for the ROP of BBL. A thorough mechanistic study is performed that evidences the presence of two concomitant DMAP-mediated mechanisms, that lead to either a DMAP or a crotonate end-capping group. Besides, in order to increase the possibilities of PHB post-polymerization functionalization, the introduction of a side-chain functionality is explored, establishing the copolymerization of BBL with ß-allyloxymethylene propiolactone (BPLOAll), resulting in well-defined P(BBL-co-BPLOAll) copolymers.


Asunto(s)
4-Butirolactona , Aluminio , Polihidroxialcanoatos , Polimerizacion , Catálisis , 4-Butirolactona/química , 4-Butirolactona/análogos & derivados , Polihidroxialcanoatos/química , Aluminio/química , Estructura Molecular , Hidroxibutiratos/química , Polihidroxibutiratos
17.
J Dairy Sci ; 107(9): 6834-6851, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38762110

RESUMEN

Flaxseed is the richest source of secoisolariciresinol diglucoside, which is converted by ruminal microorganisms primarily to the mammalian lignan enterolactone. Our objective was to investigate the effect of diets containing soybean meal or flaxseed meal (FM) supplemented with sucrose, flaxseed oil, or both, on milk enterolactone concentration yield, diversity, and relative abundance of ruminal bacterial taxa, ruminal fermentation profile, production performance, milk fatty acids (FA) yield, and nutrient utilization in dairy cows. Sixteen Holstein cows (8 multiparous [4 ruminally cannulated] and 8 primiparous) averaging (mean ± SD) 134 ± 54.1 DIM and 679 ± 78.9 kg of BW in the beginning of the study were assigned to treatment sequences in a replicated 4 × 4 Latin square design. Each experimental period lasted 25 d, with 18 d for diet adaptation and 7 d for data and sample collection. Diets were formulated to contain a 60:40 forage:concentrate ratio and included the following (DM basis): (1) 8% soybean meal and 23% ground corn (SBM); (2) 15% FM, 10.7% ground corn, and 5% sucrose (FLX+S); (3) 15% FM, 15.4% ground corn, and 3% flaxseed oil (FLX+O); and (4) 15% FM, 10.2% ground corn, 5% sucrose, and 3% flaxseed oil (FLX+SO). Compared with SBM, the concentration and yield of milk enterolactone increased in cows fed the FM diets but did not differ among FLX+S, FLX+O, and FLX+SO. The relative abundances of the phyla Firmicutes, Verrucomicrobiota, and Actinobacteriota, and those of the bacterial genera Lachnospiraceae NK3A20 group, Eubacterium coprostanoligenes group, Anaeromusa-Anaeroarcus, WCHB1-41, and p-251-o5 decreased, whereas Prevotella and NK4A214 group increased when comparing SBM against at least 1 diet containing FM. Furthermore, the relative abundances of Firmicutes and Actinobacteriota and those of Prevotella, Lachnospiraceae NK3A20 group, Eubacterium coprostanoligenes group, Acetitomaculum, Lachnospiraceae unclassified, NK4A214 group, and Anaeromusa-Anaeroarcus changed (increased or decreased) across the FLX+S, FLX+O, and FLX+SO diets. However, all these changes in the relative abundance of the ruminal bacterial taxa were not conclusively associated with the effect of diets on milk enterolactone. Diets did not affect ruminal pH and concentrations of NH3-N and total VFA. Dry matter intake and yields of milk, milk fat, and milk true protein all decreased in cows fed FLX+O or FLX+SO. Yields of milk total odd-chain FA, branched-chain FA, total <16C FA, and total 16C FA decreased with feeding FLX+O and FLX+SO. The apparent total-tract digestibilities of DM and OM were lowest in the FLX+S and FLX+O diets, with CP and ADF digestibilities lowest in cows receiving FLX+S or FLX+O, respectively. Urinary excretion of total N was lowest with feeding SBM. Contrarily, diets did not affect the urinary excretion of total purine derivatives. In brief, despite the effect of diets on the relative abundance of several ruminal microbiota phyla and genera, we were unable to conclusively associate these changes with increased milk enterolactone in FM-containing diets versus SBM.


Asunto(s)
Alimentación Animal , Dieta , Lino , Lactancia , Aceite de Linaza , Leche , Rumen , Sacarosa , Animales , Bovinos , Femenino , Leche/química , Dieta/veterinaria , Rumen/metabolismo , Rumen/microbiología , Sacarosa/metabolismo , Aceite de Linaza/farmacología , Alimentación Animal/análisis , Lignanos , Suplementos Dietéticos , Microbiota , Fermentación , 4-Butirolactona/análogos & derivados
18.
J Environ Sci Health B ; 59(7): 417-424, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38804855

RESUMEN

The choice of effective crop protection technologies is a key factors in the economical production of oilseed rape. Insecticides belonging to the group of active substances butenolides and diamides are active substances available as seed treatments in oilseed rape and promising control tools in the crop protection technologies. Our laboratory experiment demonstrated that the experimental insecticides flupyradifurone and cyantraniliprole are both effective against Eurydema ventralis (Hemiptera: Pentatomidae) when used as a seed and in-crop treatments, but there is a fundamental difference in their insect mortality inducing effects. Flupyradifurone was found to have a total mortality 96 h after application based on basipetal translocation. In the case of cyantraniliprole, the insecticidal effect of the same treatment was 27% less. The experiment showed that the acropetal translocation of the tested active substances after seed treatment did not induce efficacy comparable to that of the basipetal translocation. The study of the biophoton emission of the plants demonstrated a verifiable correlation between the different application methods of the insecticides and the photon emission intensity per unit plant surface area. In conclusion, the systematic insecticides tested, in addition to having the expected insecticidal effect, interfere with plant life processes by enhancing photosynthetic activity.


Asunto(s)
Insecticidas , Fotosíntesis , Animales , Insecticidas/farmacología , Fotosíntesis/efectos de los fármacos , Hemípteros/efectos de los fármacos , Hemípteros/fisiología , Brassica napus/efectos de los fármacos , Pirazoles/farmacología , Semillas/efectos de los fármacos , Protección de Cultivos/métodos , Piridinas/farmacología , ortoaminobenzoatos/farmacología , Control de Insectos/métodos , 4-Butirolactona/análogos & derivados
19.
Environ Toxicol Chem ; 43(7): 1497-1508, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38819074

RESUMEN

After regulation of pesticides, determination of their persistence in the environment is an important indicator of effectiveness of these measures. We quantified concentrations of two types of systemic insecticides, neonicotinoids (imidacloprid, acetamiprid, clothianidin, thiacloprid, and thiamethoxam) and butenolides (flupyradifurone), in off-crop nontarget media of hummingbird cloacal fluid, honey bee (Apis mellifera) nectar and honey, and wildflowers before and after regulation of imidacloprid on highbush blueberries in Canada in April 2021. We found that mean total pesticide load increased in hummingbird cloacal fluid, nectar, and flower samples following imidacloprid regulation. On average, we did not find evidence of a decrease in imidacloprid concentrations after regulation. However, there were some decreases, some increases, and other cases with no changes in imidacloprid levels depending on the specific media, time point of sampling, and site type. At the same time, we found an overall increase in flupyradifurone, acetamiprid, thiamethoxam, and thiacloprid but no change in clothianidin concentrations. In particular, flupyradifurone concentrations observed in biota sampled near agricultural areas increased twofold in honey bee nectar, sevenfold in hummingbird cloacal fluid, and eightfold in flowers after the 2021 imidacloprid regulation. The highest residue detected was flupyradifurone at 665 ng/mL (parts per billion [ppb]) in honey bee nectar. Mean total pesticide loads were highest in honey samples (84 ± 10 ppb), followed by nectar (56 ± 7 ppb), then hummingbird cloacal fluid (1.8 ± 0.5 ppb), and least, flowers (0.51 ± 0.06 ppb). Our results highlight that limited regulation of imidacloprid does not immediately reduce residue concentrations, while other systemic insecticides, possibly replacement compounds, concurrently increase in wildlife. Environ Toxicol Chem 2024;43:1497-1508. © 2024 The Authors. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC.


Asunto(s)
Insecticidas , Neonicotinoides , Nitrocompuestos , Neonicotinoides/análisis , Animales , Insecticidas/análisis , Nitrocompuestos/análisis , Piridinas/análisis , Abejas , Monitoreo del Ambiente , Aves , Néctar de las Plantas/química , Miel/análisis , Tiametoxam , Flores/química , Guanidinas , Tiazinas , Tiazoles , 4-Butirolactona/análogos & derivados
20.
Zhongguo Zhong Yao Za Zhi ; 49(9): 2290-2298, 2024 May.
Artículo en Chino | MEDLINE | ID: mdl-38812129

RESUMEN

Ligustilide is the main active component of the volatile oil from Angelica sinensis and Ligusticum chuanxiong in the Umbelliferae family. It is a phthalein compound with anti-inflammatory, analgesic, antioxidant, anti-tumor, anti-atherosclerosis, neuroprotective, and other pharmacological effects. It can improve the permeability of the blood-brain barrier and has important potential in the treatment of neurodegenerative diseases and other nervous system diseases, such as Alzheimer's disease, ischemic stroke, Parkinson's disease, vascular dementia, and depression. Therefore, the mechanism of ligustilide in the treatment of nervous system diseases was summarized to provide a reference for drug development and clinical application.


Asunto(s)
4-Butirolactona , Enfermedades del Sistema Nervioso , Humanos , Animales , 4-Butirolactona/análogos & derivados , 4-Butirolactona/farmacología , 4-Butirolactona/química , Enfermedades del Sistema Nervioso/tratamiento farmacológico , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/uso terapéutico
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