RESUMO
Chondrosarcoma (CS) is a malignant bone tumor arising from cartilage-producing cells. The conventional subtype of CS typically develops within a dense cartilaginous matrix, creating an environment deficient in oxygen and nutrients, necessitating metabolic adaptation to ensure proliferation under stress conditions. Although ketone bodies (KBs) are oxidized by extrahepatic tissue cells such as the heart and brain, specific cancer cells, including CS cells, can undergo ketolysis. In this study, we found that KBs catabolism is activated in CS cells under nutrition-deprivation conditions. Interestingly, cytosolic ß-hydroxybutyrate dehydrogenase 2 (BDH2), rather than mitochondrial BDH1, is expressed in these cells, indicating a specific metabolic adaptation for ketolysis in this bone tumor. The addition of the KB, ß-Hydroxybutyrate (ß-HB) in serum-starved CS cells re-induced the expression of BDH2, along with the key ketolytic enzyme 3-oxoacid CoA-transferase 1 (OXCT1) and monocarboxylate transporter-1 (MCT1). Additionally, internal ß-HB production was quantified in supplied and starved cells, suggesting that CS cells are also capable of ketogenesis alongside ketolysis. These findings unveil a novel metabolic adaptation wherein nutrition-deprived CS cells utilize KBs for energy supply and proliferation.
RESUMO
BACKGROUND: Non-alcoholic fatty liver disease (NAFLD) is now considered the most common chronic liver disease worldwide. NAFLD is related to changes in lipid metabolism and is characterized by the increase or accumulation of fat in hepatocytes that may progress to nonalcoholic steatohepatitis (NASH), which leads to the appearance of inflammatory processes. Treatment consists of changes in diet, physical activity, and weight control; however, these disorders represent a health problem and require the development of novel alternatives to treatment and prevention. NAFLD/NASH are strongly associated with other disorders, such as metabolic syndrome (MetS); in fact, NAFLD is considered the hepatic manifestation of MetS. These disorders are related to other components of MetS, including dyslipidemia, which is characterized by an imbalance in blood cholesterol and triglyceride levels. Prebiotics and probiotics benefit from treating and preventing several ailments, including liver diseases. Specifically, in dyslipidemia, NAFLD, and NASH, probiotics play a fundamental role in conducting the biotransformation of primary bile acids into secondary bile acids, which generally have important activity as immunomodulators and metabolism regulators. The mechanisms of action of pre and probiotics involve the activity of bile acid receptors, such as FXR and TGR-5, and the events resulting from their activation. Therefore, prebiotics and probiotics may be reasonable options to prevent and treat metabolic- related liver diseases.
Assuntos
Dislipidemias , Síndrome Metabólica , Hepatopatia Gordurosa não Alcoólica , Probióticos , Humanos , Hepatopatia Gordurosa não Alcoólica/terapia , Hepatopatia Gordurosa não Alcoólica/metabolismo , Prebióticos , Fígado/metabolismo , Probióticos/uso terapêutico , Síndrome Metabólica/metabolismo , Dislipidemias/tratamento farmacológico , Dislipidemias/metabolismo , Ácidos e Sais Biliares/metabolismoRESUMO
Taurine, a cysteine-derived zwitterionic sulfonic acid, is a common ingredient in energy drinks and is naturally found in fish and other seafood. In humans, taurine is produced mainly in the liver, and it can also be obtained from food. In target tissues, such as the retina, heart, and skeletal muscle, it functions as an essential antioxidant, osmolyte, and antiapoptotic agent. Taurine is also involved in energy metabolism and calcium homeostasis. Taurine plays a considerable role in bone growth and development, and high-profile reports have demonstrated the importance of its metabolism for bone health. However, these reports have not been collated for more than 10 years. Therefore, this review focuses on taurine-bone interactions and covers recently discovered aspects of taurine's effects on osteoblastogenesis, osteoclastogenesis, bone structure, and bone pathologies (e.g., osteoporosis and fracture healing), with due attention to the taurine-cartilage relationship.
Assuntos
Osteoporose , Taurina , Animais , Cartilagem/metabolismo , Humanos , Músculo Esquelético/metabolismo , Osteogênese , Taurina/metabolismoRESUMO
The components of metabolic syndrome (MetS) and hepatogastrointestinal diseases are widespread worldwide, since many factors associated with lifestyle and diet influence their development and correlation. Due to these growing health problems, it is necessary to search for effective alternatives for prevention or adjuvants in treating them. The positive impact of regulated microbiota on health is known; however, states of dysbiosis are closely related to the development of the conditions mentioned above. Therefore, the role of prebiotics, probiotics, or symbiotic complexes has been extensively evaluated; the results are favorable, showing that they play a crucial role in the regulation of the immune system, the metabolism of carbohydrates and lipids, and the biotransformation of bile acids, as well as the modulation of their central receptors FXR and TGR-5, which also have essential immunomodulatory and metabolic activities. It has also been observed that they can benefit the host by displacing pathogenic species, improving the dysbiosis state in MetS. Current studies have reported that paraprobiotics (dead or inactive probiotics) or postbiotics (metabolites generated by active probiotics) also benefit hepatogastrointestinal health.
Assuntos
Microbioma Gastrointestinal , Síndrome Metabólica , Probióticos , Disbiose/complicações , Disbiose/terapia , Humanos , Síndrome Metabólica/complicações , Síndrome Metabólica/terapia , Prebióticos , Probióticos/uso terapêuticoRESUMO
The infection of Capsicum annuum cv. mirasol by Candidatus Phytoplasma trifolii (16SrVI) causes devastating crop losses in northern Mexico. This study addresses the metabolomics profiling of mirasol chili peppers (Capsicum annuum cv. mirasol) infected by Candidatus Phytoplasma trifolii. For this study, 25 diseased fruits and 25 healthy fruits were used. Principal component analysis (PCA) and orthogonal projections to latent structures discriminant analysis (OPLS-DA) revealed dramatic changes in the content of 42 metabolites which were identified in diseased and healthy mirasol chili peppers. The endogenous levels of fructose, glucose and formic acid were substantially decreased in the diseased chili peppers. In the same group of samples, high concentrations of alanine, asparagine, fumaric acid, sucrose and threonine were observed. The content of Choline didnt present a significant difference. This evidence supports the fact that Candidatus Phytoplasma trifolii infection reduces de CO2 fixation into carbohydrates, decreases invertase activity, and inhibits glycolysis in the diseased plant tissues. The levels of ascorbic acid, capsaicin and dihydrocapsaicinin in diseased fruits were dramatically decreased, suggesting that Candidatus Phytoplasma trifolii can reduce the pungency and the nutraceutical value of mirasol chili peppers.
Assuntos
Capsicum/metabolismo , Espectroscopia de Ressonância Magnética , Metaboloma , Phytoplasma/fisiologia , Doenças das Plantas/microbiologia , Capsicum/microbiologia , Regulação da Expressão Gênica de Plantas , Análise de Componente PrincipalRESUMO
Cartilage-forming lesions include tumours that can vary in severity from benign enchondromas to high-grade malignant chondrosarcomas. Chondrosarcoma is the second most frequent malignant bone tumour, accounting for 20-30% of all malignant bone neoplasms. Surgery is the standard treatment for cartilage tumours (CTs); however, their incidental diagnosis and the difficult differentiation of low-grade lesions like chondrosarcoma grade I from benign entities like enchondroma are challenges for clinical management. In this sense, the search for circulating biomarkers for early detection and prognosis is an ongoing interest. Targeted metabolomics is a powerful tool that can propose potential biomarkers in biological fluids as well as help to discover disturbed metabolic pathways to reveal tumour pathogenesis. In this context, the aim of this study was to investigate the 1 H nuclear magnetic resonance metabolomic serum profile of patients with CTs contrasted with healthy controls. Forty-one metabolites were identified and quantified; the multivariate statistical methods principal component analysis and partial least squares discriminant analysis reveal a clear separation of the CT group, that is, the differential metabolites that were involved in two main metabolic pathways: the taurine and hypotaurine metabolism and synthesis and degradation of ketone bodies. Our results represent preliminary work for emergent serum-based diagnostics or prognostic methods for patients with chondrogenic tumours.
Assuntos
Biomarcadores Tumorais/sangue , Cartilagem/metabolismo , Condrossarcoma/diagnóstico , Espectroscopia de Ressonância Magnética/métodos , Soro/química , Adulto , Idoso , Condroma/metabolismo , Análise Discriminante , Feminino , Humanos , Masculino , Redes e Vias Metabólicas , Metabolômica/métodos , Pessoa de Meia-Idade , Simulação de Dinâmica Molecular , Análise Multivariada , Estadiamento de Neoplasias/métodos , Projetos Piloto , Soro/metabolismoRESUMO
The liver is considered the laboratory of the human body because of its many metabolic processes. It accomplishes diverse activities as a mixed gland and is in continuous cross-talk with the endocrine system. Not only do hormones from the gastrointestinal tract that participate in digestion regulate the liver functions, but the sex hormones also exert a strong influence on this sexually dimorphic organ, via their receptors expressed in liver, in both health and disease. Besides, the liver modifies the actions of sex hormones through their metabolism and transport proteins. Given the anatomical position and physiological importance of liver, this organ is evidenced as an immune vigilante that mediates the systemic immune response, and, in turn, the immune system regulates the hepatic functions. Such feedback is performed by cytokines. Pro-inflammatory and anti-inflammatory cytokines are strongly involved in hepatic homeostasis and in pathological states; indeed, female sex hormones, oral contraceptives, and phytoestrogens have immunomodulatory effects in the liver and the whole organism. To analyze the complex and interesting beneficial or deleterious effects of these drugs by their immunomodulatory actions in the liver can provide the basis for either their pharmacological use in therapeutic treatments or to avoid their intake in some diseases.
Assuntos
Anticoncepcionais Orais/metabolismo , Hormônios/metabolismo , Imunomodulação , Fígado/imunologia , Fígado/metabolismo , Fitoestrógenos/metabolismo , Anticoncepcionais Orais/farmacologia , Feminino , Hormônios/farmacologia , Humanos , Sistema Imunitário/efeitos dos fármacos , Sistema Imunitário/imunologia , Sistema Imunitário/metabolismo , Imunomodulação/efeitos dos fármacos , Fígado/efeitos dos fármacos , Estrutura Molecular , Fitoestrógenos/farmacologia , Fatores SexuaisRESUMO
Approximately 90% of the chili peppers consumed in the world are harvested in Mexico. The present article describes the untargeted 1H NMR-based metabolomic profiling of 11 cultivars of Capsicum annuum species which are routinely consumed worldwide. The metabolomic fingerprinting detected via 1H NMR contained 44 metabolites including sugars, amino acids, organic acids, polyphenolic acids and alcohols which were identified by comparison with the literature data, with Chenomx database and by 2D NMR. Statistical approaches based on principal component analysis (PCA) and linear discriminant analysis (LDA) were used to classify the Capsicum annuum cultivars according to their metabolite profile. LDA revealed metabolomic differences and similarities among Capsicum annuum cultivars, whereas hierarchical cluster analysis (HCA) significantly separated the cultivars according to the phylogenetic trees obtained. Substantial endogenous levels of free amino acids and carbohydrates were detected in all the studied cultivars but interestingly, Capsicum annuum cv. mirasol and C. annuum cv. chilaca contained almost three-fold more endogenous levels of vitamin C than the other cultivars. Considering that this antioxidant was found in crude aqueous extracts, its abundance could be directly proportional to its bioavailability for human nutrition. The results suggest that 1H NMR is an effective method to determine differences among cultivars of the Capsicum annuum species.
Assuntos
Capsicum/química , Capsicum/metabolismo , Metaboloma/fisiologia , Aminoácidos/análise , Ácidos Carboxílicos/análise , Análise Discriminante , Metabolômica , México , Ressonância Magnética Nuclear Biomolecular , Análise de Componente Principal , Açúcares/análiseRESUMO
Herein we report on the 1H NMR-based metabolomics profiling of ten new races of Capsicum annuum cv. serrano, cultivated in Mexico. Forty eight metabolites (including sugars, amino acids, organic acids, polyphenolic acids and alcohols) were identified and quantified by 2D NMR and qNMR, respectively. Principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA) separated the ten races into two clusters, from which citric acid, formic acid, fumaric acid, malic acid, glucose, fructose, sucrose and galactose were found as differential metabolites. This is the first study describing the chemical profiling of ten new races of Capsicum annuum cv. serrano and the spectrometric method used presently is characterized by great simplicity, robustness and reproducibility. Thus, this technique can be used for establishing reliable metabolomic fingerprints of different races of Capsicum annuum cv. serrano.
Assuntos
Capsicum/química , Metabolômica/métodos , Espectroscopia de Prótons por Ressonância Magnética/métodos , Aminoácidos/análise , Carboidratos/análise , Análise Discriminante , Hidroxibenzoatos/análise , Análise dos Mínimos Quadrados , Espectroscopia de Ressonância Magnética/métodos , México , Análise Multivariada , Compostos Orgânicos/análise , Análise de Componente Principal/métodos , Reprodutibilidade dos Testes , Açúcares/análiseRESUMO
This study describes the 1 H-NMR-based metabolomics profiling of juices from citrus fruits harvested in the state of Veracruz, México. The hydrophilic profile of commercial lemons (Agrio and Persian), tangerines (Fremont and Mónica), oranges (Valencia and Washington Navel), and grapefruits (Red Ruby and Rio Red) was determined. According to our results, 35 metabolites were identified in the 1 H-NMR profiling. The statistical differences obtained by PCA and OPLS-DA revealed that specific amino acids, sugars, and organic acids were differential metabolites in the species and cultivars studied. High endogenous levels of sucrose (10-190â mM), α-glucose, ß-glucose (α- and ß-isomers, 40-205â mm), and fructose (36-170â mm) were detected in the juices of grapefruits, oranges, and tangerines, whereas citric acid (40-530â mm) was the principal organic acid in the juices of lemons. To calculate the specific amounts of metabolites from these species and their cultivars, the results were finely analyzed using the qNMR method. According to these calculations, Valencia oranges had the highest concentration of ascorbic acid (>2â mm). The described 1 H-NMR method is highly reproducible, inexpensive, and highly robust in comparison to other analytical methods used to determine the hydrophilic profile of citrus juices.
Assuntos
Citrus/metabolismo , Sucos de Frutas e Vegetais/análise , Espectroscopia de Ressonância Magnética/métodos , Metaboloma , Aminoácidos/metabolismo , Ácido Ascórbico/análise , Ácido Cítrico/análise , Citrus/química , Análise por Conglomerados , Análise Discriminante , Frutose/metabolismo , Glucose/metabolismo , Análise dos Mínimos Quadrados , México , Análise de Componente PrincipalRESUMO
Fresh aqueous extracts (AGEs) and several thioallyl compounds (TACs) from garlic have an important antimicrobial activity that likely involves their interaction with exposed thiol groups at single aminoacids or target proteins. Since these groups are present in Giardia duodenalis trophozoites, in this work we evaluated the anti-giardial activity of AGE and several garlic's TACs. In vitro susceptibility assays showed that AGE affected trophozoite viability initially by a mechanism impairing cell integrity and oxidoreductase activities while diesterase activities were abrogated at higher AGE concentrations. The giardicidal activities of seven TACs were related to the molecular descriptor HOMO (Highest Occupied Molecular Orbital) energy and with their capacity to modify the -SH groups exposed in giardial proteins. Interestingly, the activity of several cysteine proteases in trophozoite lysates was inhibited by representative TACs as well as the cytopathic effect of the virulence factor giardipain-1. Of these, allicin showed the highest anti-giardial activity, the lower HOMO value, the highest thiol-modifying activity and the greatest inhibition of cysteine proteases. Allicin had a cytolytic mechanism in trophozoites with subsequent impairment of diesterase and oxidoreductase activities in a similar way to AGE. In addition, by electron microscopy a marked destruction of plasma membrane and endomembranes was observed in allicin-treated trophozoites while cytoskeletal elements were not affected. In further flow cytometry analyses pro-apoptotic effects of allicin concomitant to partial cell cycle arrest at G2 phase with the absence of oxidative stress were observed. In experimental infections of gerbils, the intragastric administration of AGE or allicin decreased parasite numbers and eliminated trophozoites in experimentally infected animals, respectively. These data suggest a potential use of TACs from garlic against G. duodenalis and in the treatment of giardiasis along with their additional benefits in the host's health.
Assuntos
Compostos Alílicos/farmacologia , Antiprotozoários/farmacologia , Alho/química , Giardia lamblia/efeitos dos fármacos , Giardíase/tratamento farmacológico , Extratos Vegetais/farmacologia , Sulfetos/farmacologia , Trofozoítos/efeitos dos fármacos , Compostos Alílicos/administração & dosagem , Compostos Alílicos/isolamento & purificação , Animais , Antiprotozoários/administração & dosagem , Antiprotozoários/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Modelos Animais de Doenças , Inibidores Enzimáticos/administração & dosagem , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Gerbillinae , Carga Parasitária , Testes de Sensibilidade Parasitária , Extratos Vegetais/administração & dosagem , Extratos Vegetais/isolamento & purificação , Sulfetos/administração & dosagem , Sulfetos/isolamento & purificação , Resultado do TratamentoRESUMO
The 750â¯MHz 1H NMR spectrum of cholesteryl benzoate (1b) could be assigned completely, which means all chemical shifts and all coupling constants, including some long-range values, were established. This task was possible by extracting many approximate coupling constant values in the overlapped spectrum region from an HSQC experiment, and using these values in the 1H iterative full spin analysis integrated in the PERCH NMR software. The task was facilitated using our published data for 3ß-acetoxypregna-5,16-dien-20-one (3), the assignment data of the sesquiterpene benzoquinone dihydroperezone (2), also performed in the present study, which contains the same carbon atoms chain than cholesterol (1a), and an HSQC study of (25R)-27-deuteriocholesterol (1c) we prepared some 40â¯years ago. The HSQC values of 1c in combination with the coupling constants of 1b also allowed to completely assigning the spectrum of 1c. The complete assignment of 1b and 1c further provided the opportunity to estimate the hydrogen shifts induced upon benzoylation of cholesterol. Comparison of the experimental vicinal coupling constants of 1b with the values calculated using the Altona software provides an excellent correlation. In addition, a single crystal X-ray diffraction study of 1b provided the molecular conformation in the solid state, which revealed the side chain adopts an extended conformation.
Assuntos
Ésteres do Colesterol/química , Espectroscopia de Ressonância Magnética/métodos , Extratos Vegetais/química , Difração de Raios XRESUMO
Beet mild curly top virus (BMCTV) is associated with an outbreak of curly top in chili pepper, tomato and other Solanaceae species, which can cause severe crop losses. The aim of this work was to obtain the 1H NMR metabolomic profiling of both healthy chili peppers (cv. mirasol) and infected chili peppers with BMCTV in order to find chemical markers associated to the infection process. Significant differences were found between the two groups, according to principal component analysis and orthogonal projections to latent structure discriminant analysis. Compared to the asymptomatic peppers, the symptomatic fruits had higher relative abundance of fructose, isoleucine, histidine, phenylalanine and tryptophan. Contrarily, the asymptomatic samples showed greater amounts of malonate and isobutyrate. These results suggest that in diseased chili peppers there are metabolic changes related to the viral acquisition of energy for replication and capsid assembly. This is the first study describing the chemical profiling of a polar extract obtained from Capsicum annuum infected by BMCTV under open field conditions.
Assuntos
Capsicum/virologia , Geminiviridae/isolamento & purificação , Espectroscopia de Ressonância Magnética , Metabolômica , Capsicum/química , Contaminação de Alimentos , Microbiologia de Alimentos , Frutas/química , Frutas/virologia , Geminiviridae/metabolismo , Doenças das Plantas/virologia , Análise de Componente PrincipalRESUMO
Detailed literature inspections regarding the diterpenoids icetexone (1) and conacytone (3) reveal that the absolute configuration (AC) of these natural occurring compounds is not rigorously proven, despite they were originally isolated in 1976. This task is now completed by single-crystal X-ray diffraction Flack and Hooft parameters determination after processing data collected with Cu Kα graphite monochromated radiation. The AC of both compounds is further determined by vibrational circular dichroism measurements performed on icetexone acetate (2) and conacytone triacetate (4) since the solubility of 1 and 3 is limited. Comparison of the substituent chemical shifts (SCS) induced by acetylation of 1 and 3 to afford 2 and 4, respectively, reveals that in the case of icetexone, all six SCS values of the quinone ring are in excellent agreement with the expected values, while in the case of conacytone, three agree and three do not agree due to the presence of additional acetates near the quinone ring. Density functional theory calculations performed on 3-hydroxythymoquinone (6) and its tautomer 4-hydroxy-1,2-quinone 7, on 6-hydroxythymoquinone (8) and its tautomer ortho-quinone 9, and on icetexone (1) and the claimed natural occurring ortho-quinone tautomer romulogarzone (5) indicate that 2-hydroxy-1,4-quinones are more stable, by some 11-14 kcal/mol, than their 4-hydroxy-1,2-quinone tautomers, and therefore, romulogarzone (5) is inexistent.
Assuntos
Diterpenos/química , Salvia/química , Diterpenos/isolamento & purificação , Modelos Moleculares , Conformação Molecular , EstereoisomerismoRESUMO
Chili pepper (Capsicum annuum) is the most important and emblematic condiment in Mexican food. Serrano pepper is a variety of C. annuum that is traditionally cultivated in Mexico and commercialized in local markets. The aim of this study was to describe the 1H NMR metabolomic profiling of the aqueous phase of serrano peppers harvested from two distinct regions, in the states of Veracruz and Oaxaca, Mexico. According to the current results, aspartate citrate, lactate, leucine and sucrose were found at higher amount in the serrano peppers from Veracruz. On the other hand, acetate, formate, fumarate, malonate, phosphocholine, pyruvate and succinate showed the highest abundance in this product from Oaxaca. These are the main metabolites that distinguish one group from the other. The spectrometric method reported presently is characterized by great simplicity, robustness and reproducibility. Thus, this technique can be used for establishing reliable metabolomic fingerprints of serrano peppers grown under different environmental conditions.
Assuntos
Capsicum/metabolismo , Metaboloma , Metabolômica/métodos , Espectroscopia de Prótons por Ressonância Magnética , Biomarcadores/metabolismo , Capsicum/classificação , Capsicum/crescimento & desenvolvimento , Meio Ambiente , MéxicoRESUMO
Petiveria alliacea L. (Phytolacaceae) is a medicinal plant with a broad range of traditional therapeutic properties, including the treatment of dysentery and intestinal infections caused by protozoan parasites. However, its effects against Entamoeba histolytica have not been reported yet. We investigated the antiamoebic activity present in the leaves of P. alliacea Antiamoebic activity was evaluated in methanolic and aqueous extracts, as well as in the hexanic, methanolic, and EtOAc fractions. The P. alliacea methanolic extract showed a better antiamoebic activity than the aqueous extract with an IC50 = 0.51 mg/ml. Likewise, the hexanic fraction was the most effective fraction, showing a dose-dependent activity against E. histolytica, with an IC50 = 0.68 mg/ml. Hexanic subfraction 12-19 showed the highest antiamoebic activity at 0.8 mg/ml, producing 74.3% growth inhibition without any toxicity in mammal cells. A major component in subfraction 12-19 was identified as isoarborinol, which produced 51.4% E. histolytica growth inhibition at 0.05 mg/ml without affecting mammal cells. The P. alliacea leaf extract has antiamoebic activity that can be attributed to a major metabolite known as isoarborinol.
Assuntos
Antiprotozoários/farmacologia , Entamoeba histolytica/efeitos dos fármacos , Compostos Fitoquímicos/farmacologia , Phytolaccaceae/química , Extratos Vegetais/farmacologia , Folhas de Planta/química , Triterpenos/farmacologia , Antiprotozoários/isolamento & purificação , Concentração Inibidora 50 , Testes de Sensibilidade Parasitária , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Triterpenos/isolamento & purificaçãoRESUMO
Complete and unambiguous 1 H NMR chemical shift assignment of α-cedrene (2) and cedrol (9), as well as for α-pipitzol (1), isocedrol (10), and the six related compounds 3-8 has been established by iterative full spin analysis using the PERCH NMR software (PERCH Solutions Ltd., Kuopio, Finland). The total sets of coupling constants are described and correlated with the conformational equilibria of the five-membered ring of 1-10, which were calculated using the complete basis set method. Copyright © 2015 John Wiley & Sons, Ltd.
Assuntos
Sesquiterpenos/química , Terpenos/química , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Conformação Molecular , Sesquiterpenos Policíclicos , SoftwareRESUMO
The naturally occurring eudesmanolide farinosin () is now fully characterized for the first time despite its original isolation almost half a century ago. The early assumed relative stereochemistry and absolute configuration were confirmed by vibrational circular dichroism together with evaluation of the Hooft X-ray parameters. The molecular conformation is very similar in the gas stage and in the solid state. Chirality 28:415-419, 2016. © 2016 Wiley Periodicals, Inc.
Assuntos
Asteraceae/química , Sesquiterpenos/química , Dicroísmo Circular , Cristalografia por Raios X , Estrutura Molecular , EstereoisomerismoRESUMO
This study was designed to examine the effects of lyophilized red delicious apple peel (RDP) on the action potentials (APs) and the input resistance-threshold current relationship. The experiments were performed on isolated papillary heart muscles from healthy male rats, healthy male rats treated with RDP, diabetic male rats, and diabetic male rats treated with RDP. The preparation was superfused with oxygenated Tyrode's solution at 37°C. The stimulation and the recording of the APs, the input resistance, and the threshold current were made using conventional electrophysiological methods. The RDP presented no significant effect in normal rats. Equivalent doses in diabetic rats reduced the APD and ARP. The relationship between input resistance and threshold current established an inverse correlation. The results indicate the following: (1) The functional structure of the cardiac ventricular syncytium in healthy rats is heterogeneous, in terms of input resistance and threshold current. Diabetes further accentuates the heterogeneity. (2) As a consequence, conduction block occurs and increases the possibility of reentrant arrhythmias. (3) These modifications in the ventricular syncytium, coupled with the increase in the ARP, are the adequate substrate so that, with diabetes, the heart becomes more arrhythmogenic. (4) RDP decreases the APD, the ARP, and most syncytium irregularity caused by diabetes.
Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Diabetes Mellitus Experimental/fisiopatologia , Coração/fisiopatologia , Malus/química , Extratos Vegetais/farmacologia , Potenciais de Ação , Animais , Arritmias Cardíacas/metabolismo , Glicemia/análise , Peso Corporal , Frutas/química , Hemoglobinas Glicadas/análise , Coração/efeitos dos fármacos , Soluções Isotônicas , Masculino , Músculos Papilares/metabolismo , Ratos , TemperaturaRESUMO
This work describes the total and unambiguous assignment of the 750 MHz (1)H NMR spectrum of 3ß-acetoxypregna-5,16-dien-20-one or 16-DPA (1), the well-known intermediate utilized in the synthesis of biological important commercial steroids. The task was accomplished by extracting the coupling constant values in the overlapped spectrum region by HSQC, and using these values in the (1)H iterative full spin analysis integrated in the PERCH NMR software. Comparison of the experimental vicinal coupling constants of 1 with the values calculated using Altona provides an excellent correlation. The same procedure, when applied to the published data of progesterone (2) and testosterone (3), afforded an acceptable correlation for 2 and a poor correlation for 3. In the last case, this suggested the reassignment of all four vicinal coupling constants for the methylene signals at the C-15 and C-16 positions, demonstrating the utility of this methodology.