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Article in Chinese | WPRIM | ID: wpr-878849


Chemical investigation on the constituents of the ethyl acetate soluble extraction of Litsea cubeba has resulted in the isolation and structure elucidation of thirty compounds, including one sesquiterpene(1), four monoterpenes(2-5), two γ-butyrolactone derivatives(6 and 7), seven tyramine derivatives(8-14), fifteen aromatic compounds(15-29), and one pyrone derivative(30) via various chromatographic techniques and spectroscopic data analysis(MS, IR, 1 D and 2 D NMR). Compounds 1-7, 13 and 14 were obtained from the genus Litsea for the first time.

Acetates , Litsea , Monoterpenes , Sesquiterpenes
Rev. colomb. quím. (Bogotá) ; 47(1): 5-9, ene.-abr. 2018. graf
Article in Spanish | LILACS-Express | LILACS | ID: biblio-900833


Resumen La tiramina y la N-benciltiramina reaccionan con formaldehído para formar azaciclofanos por medio de condensaciones tipo Mannich aromáticas y reaccionan con aldehídos no enolizables para formar las respectivas bases de Schiff. En este artículo se presenta la síntesis inesperada de N-bencil-N-formiltiramina y N-bencil-N-metiltiramina por medio de reacciones de transamidación y de transamidación-reducción de N-benciltiramina con N,N-dimetilformamida. Para explicar el curso de la reacción se propuso un mecanismo que involucra la formilación de N-benciltiramina y posterior reducción de Leuckart-Wallach inducida por ácido fórmico generado in situ.

Abstract Tyramine and N-benzyltyramine react with formaldehyde to form azacyclophanes by means of aromatic Mannich reactions and react with non-enolizable aldehydes to form the respective Schiff bases. In this paper we present the unexpected synthesis of N-formyl-N-benzyltyramine and N-methyl-N-benzyltyramine by means of transamidation and transamidation-reduction of N-benzyltyramine with N,N-dimethylformamide. A reaction mechanism involving formylation of N-benzyltiramine followed by a Leuckart-Wallach reduction is proposed for rationalising such transformation.

Resumo A tiramina e a N-benziltiramina reagem com formaldeído para formar azaciclofanos por meio de reações de Mannich aromáticas e reagem com aldeídos não-enolizáveis para formar as respectivas bases de Schiff. Neste trabalho apresenta-se a síntese inesperada de N-formil-N-benziltiramina e N-metil-N-benziltiramina por meio de transamidação e transamidação-redução de N-benziltiramina promovida pela N,N-dimetilformamida. Propõe-se um mecanismo de reação que envolve a formilação de N-benziltiramina seguida por uma redução de Leuckart-Wallach induzida pelo ácido fórmico gerado in situ.

Article in Chinese | WPRIM | ID: wpr-851967


Objective To study the chemical constituents and anti-neuroinflammatory activity of the caulis of Tinospora sinensis as a "Yao" medicine. Methods The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, ODS column chromatographies, and semi-preparative HPLC. The structures of these compounds were elucidated by extensive spectroscopic analyses and chemical methods. All compounds were evaluated for their anti-neuroinflammatory effect by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine BV-2 microglial cells except for compounds 7 and 8. Results Thirteen compounds were isolated from the caulis of T. sinensis. They were identified as tinosposide C (1), tinosposide D (2), seco-isolariciresinol 9-O-β-glucopyranoside (3), (+)-pinoresinol 4-O-β-D-glucopyranoside (4), (+)-syringaresinol (5), tanegoside A (6), (E)-3-[(2,3-trans)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-2,3-dihydrobenzo [b] [1,4]dioxin-6-yl]-N-(4-hydroxyphenethyl) acrylamide (7), thoreliamide B (8), trans-N-p-coumaroyltyramine (9), N-trans-feruloyltyramine (10), N-trans-caffeoyltyramine (11), grossamide K (12), and cis-grossamide K (13), seven of which exhibited significant anti-neuroinflammatory activity with IC50 values ranging from 1.46 to 51.25 μmol/L. Conclusion Compounds 1 and 2 are new compounds and their absolute configurations are confirmed by ECD experiments, compounds 3, 5, 7, 8, and 10-13 are isolated from the plants for the first time. The activity of compounds 9 and 10 is better than positive control minocycline.

Electron. j. biotechnol ; 30: 24-32, nov. 2017. tab, ilus, graf
Article in English | LILACS | ID: biblio-1021325


Background: Prosopis, or mesquite (Prosopis juliflora (Sw.) DC.), was introduced in Saudi Arabia several decades ago and is heavily used in street, roadside, and park plantations. It shows great adaptation to the prevailing climatic conditions such as high temperature, severe drought, and salinity and spreads naturally in many parts of the Kingdom. This research was conducted to isolate allergen proteins and biogenic amines from the pollen grains of P. juliflora genotypes in Saudi Arabia from two regions, namely Al-Qassim and Eastern regions. Results: The results showed that 18 different allergen proteins were detected in P. juliflora genotypes, with molecular weight ranging from 14 to 97 kDa. Moreover, P. juliflora genotypes from the two studied regions contained eight biogenic amines, namely histamine, tyramine, tryptamine, ß-phenylethylamine, butricine, codapherine, spermidine, and spermine. All genotypes from the Al-Qassim region were found to contain all eight amines, while in the Eastern region, histamine was absent in three genotypes, spermine was absent in six genotypes, and spermidine was absent in three genotypes. Genotypes B23, E20, and E21 had the lowest biogenic amine quantity. Conclusions: All identified proteins from mesquite trees from both regions (Eastern and Al-Qassim) cause allergies in patients who are sensitive to pollen grains. Bioamines, except histamine and tyramine, were recorded at varying concentrations in different genotypes.

Pollen/chemistry , Biogenic Amines/isolation & purification , Allergens/isolation & purification , Prosopis , Plant Proteins/isolation & purification , Histamine/isolation & purification , Tyramine/isolation & purification , Chromatography, High Pressure Liquid , Electrophoresis, Polyacrylamide Gel , Genotype , Molecular Weight
Article in Chinese | WPRIM | ID: wpr-484791


Objective Quadratic regression universal rotary combination design was used to optimize the fluorescence labeling condition of lycium barbarum polysaccharide (LBP).Methods The fluorescence labeling condition of LBP presented, when the covalent coupling of LBP and tyramine was reacted with fluorescein isothiocyanate (FITC). Filter the best labeling condition via using quadratic regression universal rotary combination design experiment on the relationship of labeling efficiency among pH value of buffer solution, reaction time, temperature and the dose of tyramine.Results The regression equation was:Y=0.085 41 - 0.002 82X1 - 0.015 68X2 + 0.008 11X3 + 0.005 01X4 + 0.008 75X1X2 - 0.005 75X1X3 - 0.001 75X1X4 + 0.010 63X2X3 + 0.000 125X2X4 + 0.000 25X3X4 - 0.021 44X12 - 0.008 89X22 - 0.001 984X32 + 0.003 66 X42, and the variables fromX1 toX4 represented pH value, reaction time, temperature and dose of tyramine, respectively. The goodness of fitting of regression equation was statistically significant. The condition of labling LBP was optimized when the temperature was at 50℃, timing of labling at the fourth day and pH value was 8.5.Conclusion The condition of labling LBP was optimized with suitable temperature, pH value and extended timing.

Article in English | IMSEAR | ID: sea-166856


Tyrosinase is the rate-limiting oxidase in the synthesis of melanin, making it an obvious target for the treatment of melanotic melanomas. Tyrosine and tyramine are its natural substrates, but many of their derivatives are inhibitors or false substrates, and are therefore prime candidates for melanoma chemotherapy. A series of dialkylphosphonate derivatives of tyramine have now been synthesized in order to extend the chemical diversity of tyrosinase substrates. The known reactivity between alkenephosphonates and nucleophiles was exploited by the addition of 4-(2-aminoethyl)phenol (tyramine) across the 2,3-double bond of 1,2-alkadiene phosphonates, to obtain the desired bisphosphonate derivatives. These reactions were highly chemoselective and regioselective but not stereoselective. Five of the reported novel dialkylphosphonate aminophenols were substrates for mushroom tyrosinase in vitro: dimethyl 2-[2(4-hydroxyphenyl)ethylamino]-3-methyl-1-butenephosphonate (3);diethyl 2-[2(4-hydroxyphenyl)ethylamino]-3-methyl-1-butenephosphonate (4);dimethyl 2-[2-(4- hydroxyphenyl)ethylamino]-2-cyclohexyl-1-ethenephosphonate (5);diethyl 2-[2-(4-hydroxyphenyl)ethylamino]- 2-cyclohexyl-1-ethenephosphonate (6);diethyl 2-[2-(4-hydroxyphenyl)ethylamino]ethanephosphonate (7). Compound 3 blocked the pigmentation of anagen hair in vivo in a murine animal model, a further demonstration that these compounds are able to enter and disrupt the melanogenic pathway.

Ciênc. saúde coletiva ; 19(4): 1123-1134, abr. 2014.
Article in Portuguese | LILACS | ID: lil-710518


Aminas biogênicas são bases orgânicas de baixo peso molecular com atividade biológica, produzidas a partir da ação da enzima descarboxilase. Microrganismos utilizados na fermentação de alimentos são capazes de produzi-las. O consumo desses compostos causam graves efeitos toxicológicos, indesejáveis para a saúde humana. Embora não exista legislação específica sobre a quantidade máxima permitida de aminas em alimentos e bebidas, a presença e o acumulo destes compostos é de grande importância. O objetivo desta revisão é evidenciar a necessidade de mais estudos e discutir a presença de aminas biogênicas em alimentos variados.

Biogenic amines are low molecular weight organic bases with biological activity, produced by the action of the decarboxylase enzyme. Microorganisms used in food fermentation are able to produce them. Consumption of these compounds causes serious toxicological effects, which are undesirable for human health. Although there is no specific legislation regarding the amine content in food and beverages, the presence and accumulation of amines is a matter of great importance. The aim of this review is to highlight the need for further studies and foment debate about the presence of biogenic amines in a variety of foods.

Biogenic Amines , Food Contamination , Food Contamination/prevention & control , Risk
Chinese Pharmaceutical Journal ; (24): 1400-1403, 2012.
Article in Chinese | WPRIM | ID: wpr-860636


OBJECTIVE: To establish an HPCE method for determination of N-trans-feruloyl tyramine in Lycii Fructus. METHODS: The chromatographic separation was performed on an uncoated fused silica capillary of 50 cm × 75 μm ID (40 cm of effective length). 50 mmol · L-1Na2B4O7(pH 9.0 with H3PO4) was selected as the running buffer. The applied voltage was 20 kV, and the column temperature was maintained at 25°C. The chromatogram was detected at 214 nm. RESULTS: The linearity for N-trans-feruloyl tyramine was in a range of 0.25 - 15 μg · mL-1 (r = 0.9998, n = 7). The average recovery for N-trans-feruloyl tyramine was 101.8% with RSD of 2.06%. CONCLUSION: The method is accurate, reliable, and can be used as a quality control method for N-trans-feruloyl tyramine in Lycii Fructus, which can provide basis for development and utilization of Lycii Fructus. Copyright 2012 by the Chinese Pharmaceutical Association.

Article in English | WPRIM | ID: wpr-111870


The aim of the present study was to investigate the hypocholesterolemic effect and potential of tyramine derivatives from Lycii Cortex Radicis (LCR), the root bark of lycium (Lycium chenese Miller) in reducing lipid peroxidation. The activities of enzymes, hepatic 3-hydroxy 3-methylglutaryl (HMG) CoA reductase and acyl-CoA:cholesterol acyltransferase (ACAT) and LDL oxidation were measured in vitro and animal experiments were also performed by feeding LCR extracts to rats. The test compounds employed for in vitro study were trans-N-p-coumaroyltyramine (CT) and trans-N-feruloyltyramine (FT), LCR components, N-(p-coumaroyl)serotonin (CS) and N-feruloylserotonin (FS) from safflower seeds, ferulic acid (FA) and 10-gingerol. It was observed that FT and FS at the concentration of 1.2 mg/mL inhibited liver microsomal HMG CoA reductase activity by ~40%, but no inhibition of activity was seen in the cases of CT, CS, FA and 10-gingerol. Whereas, ACAT activity was inhibited ~50% by FT and CT, 34-43% by FS and CS and ~80% by 10-gingerol at the concentration of 1 mg/mL. A significant delay in LDL oxidation was induced by CT, FT, and 10-gingerol. For the animal experiment, five groups of Sprague-Dawley male rats were fed high fat diets containing no test material (HF-control), 1 and 2% of LCR ethanol extract (LCR1 and LCR2), and 1% of extracts from safflower seed (Saf) and ginger (Gin). The results indicated that total cholesterol level was significantly lower in Saf, LCR2 and Gin groups, and HDL cholesterol level was lower only in Gin group when compared with HF-control group; while there was no difference in the serum triglyceride levels among the five experimental groups. The level of liver cholesterol was significantly lower in LCR1 and LCR2 groups than HF-control. Serum levels of TBARS were significantly lower only in LCR2 group when compared with HF-control group. From the observed results, we concluded that LCR can be utilized as a hypocholesterolemic ingredient in combination with ginger, especially for functional foods.

Acetylmuramyl-Alanyl-Isoglutamine , Animal Experimentation , Animals , Carthamus tinctorius , Catechols , Cholesterol , Cholesterol, HDL , Coumaric Acids , Diet, High-Fat , Ethanol , Fatty Alcohols , Functional Food , Ginger , Humans , Hydroxymethylglutaryl CoA Reductases , Lipid Peroxidation , Liver , Lycium , Male , Oxidoreductases , Polysorbates , Rats , Seeds , Serotonin , Squalene , Thiobarbituric Acid Reactive Substances , Tyramine
Article in Chinese | WPRIM | ID: wpr-403840


A novel and highly sensitive voltammetric enzyme-linked immunosensor was developed based on tyramine) oxidation deposition. It was shown that gold nano-particles(colloid Au) could be used as a platform to immobilize antibodies by adsorption. By a sandwich immunossary format with goat-anti-human IgG labled Horseradish peroxidase(HRP) as the second antibody and catalytic amplification by biotin-tyramine, the immunosensor′s) catalytic ability to hydrogen peroxide increased nearly 20 times), the sensor exhibitd a linear response to human IgG in the concentration range from 1.5 μg/L-22 mg/L, and the detection limit was 0.1 μg/L), the regression equation could be expressed as Δi_p(μA) =2.8859c(mg/L)+17.152 with a correlation) coefficient of 0.9872. The immunosensor can be used to quantitatively determine hIgG in the sample) of human serum).

Rev. cuba. med. trop ; 61(1)ene.-abr. 2009. graf
Article in Spanish | LILACS | ID: lil-547068


Se modificó el ELISA DAVIH-Ag P24 con la introducción de la disociación por calor de las muestras de plasma y el empleo de un sistema de amplificación biotina-tiramina/estreptavidina-peroxidasa, para incrementar su sensibilidad. Se determinó la repetibilidad interensayo en el DAVIH-Ag P24 amplificado. Se evaluaron 32 muestras de plasma de individuos infectados por el VIH-1 en 3 categorías clínicas (caso SIDA, asintomßticos y con infecciones oportunistas menores). En la determinación de la repetibilidad interensayo se obtuvo un coeficiente de variación entre 4 y 10,3 por ciento. Con el DAVIH-Ag P24 amplificado se incrementó el nivel de detección de P 24 hasta 0,5 pg/mL. El DAVIH-Ag P24 amplificado alcanzó 66 por ciento de sensibilidad, mientras que el DAVIH-Ag P24 obtuvo 31 por ciento. Este estudio preliminar permitió demostrar que la incorporación de las nuevas modificaciones al sistema DAVIH-Ag P24 amplificado logró aumentar los niveles de detección de P24 y ganar en sensibilidad.

ELISA DAVIH-Ag p24 was modified by introducing heat dissociation of plasma samples and a tyramine/streptavidine-peroxidase amplification system, with the objective of increasing sensitivity. Between-assay repeatability was determined in amplified DAVIH-Ag p24. Thirty two plasma samples from HIV-1-infected individuals classified in three clinical categories (AIDS case, asymptomatic and minor opportunistic infections) were evaluated. The variation coefficient ranged 4-10.3 percent in between-assay repeatability. With the amplified DAVIH-p24 Ag, the p24 antigen detection level increased to 0.5 pg/mL. Amplified DAVIH-p24 Ag reached 66 percent sensitivity whereas standard DAVIH-p24 Ag sensitivity rate was 31 percent. This preliminary study proved that the introduction of new modifications in amplified DAVIH-p24 Ag managed to increase the p24 antigen detection levels and to gain sensitivity.

Humans , HIV , /analysis , /chemistry
Arch. cardiol. Méx ; 74(2): 108-117, abr.-jun. 2004. ilus
Article in Spanish | LILACS | ID: lil-749628


Se evaluó farmacológicamente los extractos de diversas variedades de Magnolia grandiflora sobre el músculo cardíaco. Se recolectó en el período de marzo a julio hojas y flores de Magnolia grandiflora nativa del Instituto Nacional de Cardiología "Ignacio Chávez", de la zona norte, poniente y oriente del Distrito Federal, de los estados de Puebla, Colima y Chiapas. Éstas se procesaron por separado y los extractos se obtuvieron por maceración con una mezcla de etanol-agua (1:3 v/v) a 4°C durante dos semanas. El análisis cualitativo se realizó por cromatografía en capa fina, columna y de líquidos de alta resolución (CLAR). El análisis funcional y molecular se efectuó por reactividad química específica y resonancia magnética protónica (RMN ¹H). La evaluación farmacológica se realizó en corazones aislados de cobayo macho. Los extractos, fracciones y compuestos se administraron en bolos seriados bajo un estudio de curvas dosis-respuesta gradual en donde se midió la presión intraventricular izquierda y la presión de perfusión coronaria, evaluando así el efecto inotrópico positivo y vasodilatador de los extractos de Magnolia grandiflora. Se identificó y aisló vulgarenol y 2-p-hidroxifenil-2-OH-etilamina, por lo que los resultados sugieren que su efecto vasodilatador e inotrópico positivo, se deben a la presencia de estas sustancias, las cuales se complementan con magnograndiólido y tiramina.

Several extracts from diverse Magnolia grandiflora varieties were pharmacological evaluated in the cardiac muscle. From March to July, flowers and leaves from Magnolia grandiflora, native from the National Institute of Cardiology "Ignacio Chávez", from north, west, and orient zones from Mexico City, and from Puebla, Colima and Chiapas states were collected. They were separately processed and the extracts were obtained by maceration with ethanol-water (1:3 v/v) at 4°C during two weeks. Qualitative analysis was accomplished with thin-layer, column and high-performance liquid chromatographies (HPLC). Functional and molecular analysis was made by specific chemical reactivity and by protonic magnetic resonance (RMN ¹H). Pharmacological evaluation was completed in isolated and perfused male guinea pigs hearts. Extracts, fractions, and compounds were administrated by serial bolus in a gradual dose-response curves study in which left intraventricular pressure and coronary perfusion pressure were recorded, evaluating by such the positive inotropic and vasodilator effects of Magnolia grandifloraextracts. Vulgarenol and 2-p-hydroxyphenyl-2-hydroxy-ethylamine were isolated and identified, and the obtained results suggest that its positive inotropic and vasodilator effects are owed to these substances, being complemented by magnograndiolide and tyramine.

Animals , Guinea Pigs , Male , Heart/drug effects , Magnolia , Plant Extracts/pharmacology , Case-Control Studies , Chromatography, Gel , Coronary Vessels/drug effects , Coronary Vessels/physiology , Heart/physiology , Magnetic Resonance Spectroscopy , Myocardium/metabolism , Ventricular Function, Left/drug effects , Ventricular Function, Left/physiology , Ventricular Pressure/drug effects , Ventricular Pressure/physiology
Article in Chinese | WPRIM | ID: wpr-591041


Objective To establish a HPLC method for the determination of octopamine in fish sauce.Methods A phenomenes luna C18 column was used.The mobile phase was 0.02?g?mL-1 citric acid-0.02?g?mL-1 sodium dihydrogen phosphate(7∶3,v/v) and detection wavelength was 274 nm.Results The linear range of octopamine was 104.0%,RSD=1.53%.The detection limit was 5.7ng?mL-1.Conclusion This method is simple,rapid and reliable.It could be used for the determination of octopamine and its related substances in fish sauce.The content of octopamine in Engraulis japonicus sauce is 1055?g?mL-1.

Article in Chinese | WPRIM | ID: wpr-549255


The mutagenicity of 22 kinds of foods, including soy sauce, fish sauce, shrimp paste, sausages, sundried fishes, rice cracker, deep fried pork skin, salfed vegetable and spices after nitrite treatment, was detected by means of Ames test with preincubation. Mutagenicity assay was employed on salmonella typhimurium TA100, aud meanwhile, the validity of each experiment was checked by using the koown mutagen, AF-2, as the positive control.16 kinds of foods showed marked direct-acting mutagenicity toward Salmonella typhimurium TA100 after nitrite treatment.Shrimp paste produced in Bankok was the strongest one among these samples.Its specific mutgenicity was 37000 revertants/g.The amount of precursor, tyramine, in shrimp paste was estimated from the area of tyramine peak on HPLC by using the authentic tyramine as the standard.Results showed that one gram shrimp paste contained 439ug tyramine.The mutagenicity of foods suggested that nitrosatable precursors, such as amine or amide, were presented in foods, and they could converted into endogenous carcinogen, mtrosamine, in vivo.Therefore, detection of mutagenicity of foods has significance in preventing cancer.