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1.
Molecules ; 29(1)2023 Dec 21.
Artículo en Inglés | MEDLINE | ID: mdl-38202652

RESUMEN

2-O-Alkyl-l-ascorbic acids and 3-O-alkyl-l-ascorbic acids were synthesized, and their degranulation inhibitory activities were evaluated. Among ascorbic acid derivatives with butyl, octyl, dodecyl, hexadecyl, and octadecyl groups introduced at the C-2 or C-3 positions, an AA derivative with a dodecyl group introduced at the C-3 position, 3-O-dodecyl-l-ascorbic acid (compound 8), showed the strongest inhibitory activity against antigen-stimulated degranulation. Compound 8 also inhibited calcium ionophore-stimulated degranulation. Compound 11, in which the hydroxyl group at the C-6 position of compound 8 was substituted with an amino group, and compound 12, in which the dodecyloxy group at the C-3 position of compound 8 was exchanged with a dodecylamino group, were synthesized, and these derivatives showed weaker inhibitory activity against antigen-stimulated degranulation than that of compound 8. In addition, orally administered compound 8 inhibited passive cutaneous anaphylaxis reactions in mice with a potency equal to that of oxatomide, an antiallergic agent. These results suggest that compound 8 may be a candidate for antiallergic treatment.


Asunto(s)
Antialérgicos , Animales , Ratones , Antialérgicos/farmacología , Ácido Ascórbico/farmacología
2.
Molecules ; 27(22)2022 Nov 08.
Artículo en Inglés | MEDLINE | ID: mdl-36431771

RESUMEN

Isorhamnetin-3-O-glucoside and astragalin, flavonol glucosides, were isolated from the petals of Paeonia lactiflora as neurite outgrowth-promoting compounds. Isoquercitrin, formed by demethylating the B ring of isorhamnetin-3-O-glucoside or by adding a hydroxyl group to the B ring of astragalin, was evaluated for neurite outgrowth-promoting activity and was compared with the activities of isorhamnetin-3-O-glucoside and astragalin. The activities of isorhamnetin, kaempferol, and quercetin, aglycones corresponding to isorhamnetin-3-O-glucoside, astragalin, and isoquercitrin, respectively, were also evaluated. Isorhamnetin-3-O-glucoside and astragalin showed much stronger neurite outgrowth-promoting activities than the activities of the other tested flavonoids. They exhibited relatively weak anti-oxidant activities and moderate AChE inhibitory activities compared to the activities of the other tested flavonoids. Isorhamnetin-3-O-glucoside and astragalin promoted morphological neurite outgrowth and the expression of neurofilaments induced by NGF in PC12 cells. Isorhamnetin-3-O-glucoside and astragalin might be candidate compounds as neural differentiation agents in peripheral nerves and functional food ingredients preventing cognitive decline.


Asunto(s)
Paeonia , Ratas , Animales , Células PC12 , Flavonoides/farmacología , Glucósidos/farmacología , Proyección Neuronal
3.
J Cell Biochem ; 122(7): 739-751, 2021 07.
Artículo en Inglés | MEDLINE | ID: mdl-33586155

RESUMEN

The appropriate regulation of spindle orientation maintains proper tissue homeostasis and avoids aberrant tissue repair or regeneration. Spindle misorientation due to imbalance or improper functioning leads to a loss of tissue integrity and aberrant growth, such as tissue loss or overgrowth. Pharmacological manipulation to prevent spindle misorientation will enable a better understanding of how spindle orientation is involved in physiological and pathological conditions and will provide therapeutic possibilities to treat patients associated with abnormal tissue function caused by spindle misorientation. N-terminal-deleted Rho guanine nucleotide dissociation inhibitor ß (RhoGDIß/RhoGDI2/LyGDI) produced by caspase-3 activation perturbs spindle orientation in surviving cells following exposure to either ionizing radiation or UVC. Thus, presumably, RhoGDIß cleaved by caspase-3 activation acts as a determinant of radiation-induced spindle misorientation that promote aberrant tissue repair due to deregulation of directional organization of cell population and therefore becomes a potential target of drugs to prevent such response. The objective of this study was to screen and identify chemicals that suppress RhoGDIß expression. We focused our attention on ascorbic acid (AA) derivatives because of their impact on the maintenance of skin tissue homeostasis. Here, we screened for AA derivatives that suppress RhoGDIß expression in HeLa cells and identified a lipophilic derivative, 2-O-octadecylascorbic acid (2-OctadecylAA), as a novel RhoGDIß inhibitor that ameliorated ionizing radiation-induced abnormal spindle orientations. Among all examined AA derivatives, which were also antioxidative, the inhibition activity was specific to 2-OctadecylAA. Therefore, this activity was not due to simple antioxidant properties. 2-OctadecylAA was previously shown to prevent hepatocellular carcinoma development. Our findings suggest that the anticarcinogenic effects of 2-OctadecylAA are partly due to RhoGDIß inhibition mechanisms by which spindle orientation perturbations are attenuated. Thus, the molecular targeting features of RhoGDIß warrant its further development for the treatment or control of spindle orientation abnormalities that affect epithelial homeostasis.


Asunto(s)
Ácido Ascórbico/análogos & derivados , Daño del ADN , Regulación de la Expresión Génica/efectos de los fármacos , Huso Acromático/patología , Inhibidor beta de Disociación del Nucleótido Guanina rho/antagonistas & inhibidores , Ácido Ascórbico/farmacología , Células HeLa , Humanos , Huso Acromático/efectos de los fármacos , Huso Acromático/metabolismo
4.
Molecules ; 26(15)2021 Aug 03.
Artículo en Inglés | MEDLINE | ID: mdl-34361837

RESUMEN

Allergy is an excessive immune response to a specific antigen. Type I allergies, such as hay fever and food allergies, have increased significantly in recent years and have become a worldwide problem. We previously reported that an ascorbic acid derivative having palmitoyl and glucosyl groups, 2-O-α-d-glucopyranosyl-6-O-hexadecanoyl-l-ascorbic acid (6-sPalm-AA-2G), showed inhibitory effects on degranulation in vitro and on the passive cutaneous anaphylaxis (PCA) reaction in mice. In this study, several palmitoyl derivatives of ascorbic acid were synthesized and a structure-activity relationship study was performed to discover more potent ascorbic acid derivatives with degranulation inhibitory activity. 6-Deoxy-2-O-methyl-6-(N-hexadecanoyl)amino-l-ascorbic acid (2-Me-6-N-Palm-AA), in which a methyl group was introduced into the hydroxyl group at the C-2 position of ascorbic acid and in which the hydroxyl group at the C-6 position was substituted with an N-palmitoyl group, exhibited much higher inhibitory activity for degranulation in vitro than did 6-sPalm-AA-2G. 2-Me-6-N-Palm-AA strongly inhibit the PCA reaction in mice at lower doses than those of 6-sPalm-AA-2G. These findings suggest that 2-Me-6-N-Palm-AA may be a promising therapeutic candidate for allergic diseases.


Asunto(s)
Antialérgicos , Ácido Ascórbico , Degranulación de la Célula/efectos de los fármacos , Hipersensibilidad/tratamiento farmacológico , Anafilaxis Cutánea Pasiva , Animales , Antialérgicos/síntesis química , Antialérgicos/química , Antialérgicos/farmacología , Ácido Ascórbico/análogos & derivados , Ácido Ascórbico/síntesis química , Ácido Ascórbico/química , Ácido Ascórbico/farmacología , Modelos Animales de Enfermedad , Ratones
5.
Molecules ; 26(19)2021 Sep 24.
Artículo en Inglés | MEDLINE | ID: mdl-34641346

RESUMEN

In this study, we present the isolation and characterization of the structure of six gallotannins (1-6), three ellagitannins (7-9), a neolignan glucoside (10), and three related polyphenolic compounds (gallic acid, 11 and 12) from Trapa bispinosa Roxb. pericarp extract (TBE). Among the isolates, the structure of compound 10 possessing a previously unclear absolute configuration was unambiguously determined through nuclear magnetic resonance and circular dichroism analyses. The α-glucosidase activity and glycation inhibitory effects of the isolates were evaluated. Decarboxylated rugosin A (8) showed an α-glucosidase inhibitory activity, while hydrolyzable tannins revealed stronger antiglycation activity than that of the positive control. Furthermore, the identification and quantification of the TBE polyphenols were investigated by high-performance liquid chromatography coupled to ultraviolet detection and electrospray ionization mass spectrometry analysis, indicating the predominance of gallic acid, ellagic acid, and galloyl glucoses showing marked antiglycation properties. These findings suggest that there is a potential food industry application of polyphenols in TBE as a functional food with antidiabetic and antiglycation activities.


Asunto(s)
Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Lythraceae/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Dicroismo Circular , Ácido Elágico/aislamiento & purificación , Industria de Alimentos , Alimentos Funcionales/análisis , Ácido Gálico/análogos & derivados , Ácido Gálico/aislamiento & purificación , Glucósidos/aislamiento & purificación , Taninos Hidrolizables/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Polifenoles/química , Polifenoles/aislamiento & purificación , Espectrometría de Masa por Ionización de Electrospray
6.
Analyst ; 143(4): 874-882, 2018 Feb 12.
Artículo en Inglés | MEDLINE | ID: mdl-29327754

RESUMEN

l-Ascorbic acid (AA) has diverse physiological functions, but little is known about the functional mechanisms of AA. In this study, we synthesized two types of affinity resin on which AA is immobilized in a stable form to identify new AA-targeted proteins, which can provide important clues for elucidating unknown functional mechanisms of AA. To our knowledge, an affinity resin on which AA as a ligand is immobilized has not been prepared, because AA is very unstable and rapidly degraded in an aqueous solution. By using the affinity resins, cytochrome c (cyt c) was identified as an AA-targeted protein, and we showed that oxidized cyt c exhibits specific affinity for AA. These results suggest that two kinds of AA-affinity resin can be powerful tools to identify new target proteins of AA.


Asunto(s)
Ácido Ascórbico/química , Cromatografía de Afinidad , Proteínas/química , Animales , Química Encefálica , Citocromos c/química , Humanos , Masculino , Ratones Endogámicos ICR , Simulación del Acoplamiento Molecular , Oxidación-Reducción
7.
J Agric Food Chem ; 2024 Apr 15.
Artículo en Inglés | MEDLINE | ID: mdl-38619067

RESUMEN

The pericarp extract of Trapa bispinosa (TBPE), which is rich in hydrolyzable tannins, has been reported to inhibit α-glucosidase and glycation reactions. We investigated the in vivo behavior of hydrolyzable tannins and related metabolites after administration of TBPE to rats. Using high pressure liquid chromatography-electrospray ionization-tandem mass spectroscopy (HPLC-ESI-MS/MS), 12 ellagitannin metabolites, such as urolithins and 6 gallotannin metabolites, produced in the collected plasma and urine were quantified. Urolithins and gallic acid metabolites reached their maximum blood concentration after 24 and 1 h of administration, respectively. Conversely, the excretion of urolithins in urine required up to 72 h and followed a sigmoidal curve, whereas gallic acid metabolites were rapidly excreted earlier after administration. The results suggest that the metabolites gallotannin and ellagitannin are responsible for the antiglycation effect of TBPE, which proceeds via different mechanisms and times. Our findings provide basic data demonstrating the functionality of hydrolyzable tannins as well as Trapa ingredients.

8.
J Nutr Sci Vitaminol (Tokyo) ; 68(3): 236-239, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35768255

RESUMEN

We previously reported that 2-O-α-D-glucopyranosyl-6-O-octanoyl-L-ascorbic acid, having a C8 straight acyl chain, at a concentration of 100 µM remarkably enhanced nerve growth factor (NGF)-induced neurite outgrowth in PC12 cells after being metabolized to L-ascorbic acid (AA) as an active form by esterase and α-glucosidase. In this study, to examine the structure-activity relationship of 6-O-substituted AA derivatives with a C8 straight acyl chain for neurite outgrowth-promoting activity, we synthesized AA derivatives 1-4 and compared their activities for promoting NGF-induced neurite outgrowth in PC12 cells. AA derivatives 1-4 showed neurite outgrowth-enhancing activity at 100 µM, while AA derivative 2 also showed the enhancing activity at 3 µM. Furthermore, AA derivative 2 as well as AA enhanced NGF-induced neurite outgrowth after being incorporated into PC12 cells via sodium-dependent vitamin C transporter as an anion transporter. The results suggested that AA derivative 2 has neurite outgrowth-enhancing activity in its intact form at a low concentration (3 µM) and that AA derivatives 1-4 showed their activities in the form of AA, a metabolite of these derivatives, at a higher concentration (100 µM).


Asunto(s)
Ácido Ascórbico , Factor de Crecimiento Nervioso , Animales , Ácido Ascórbico/metabolismo , Ácido Ascórbico/farmacología , Esterasas/metabolismo , Factor de Crecimiento Nervioso/farmacología , Proyección Neuronal , Ratas , alfa-Glucosidasas/metabolismo
9.
Biosci Biotechnol Biochem ; 74(9): 1969-71, 2010.
Artículo en Inglés | MEDLINE | ID: mdl-20834147

RESUMEN

6-O-dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (6-sDode-AA-2G) was synthesized from 2-O-α-D-glucopyranosyl-L-ascorbic acid and vinyl laurate with a protease from Bacillus subtilis in 30% dimethylformamide (DMF)/dioxane with a low water content. The addition of 3% (v/v) water to DMF/dioxane dramatically enhanced the 6-sDode-AA-2G synthesis. The optimum reaction conditions enabled 6-sDode-AA-2G to be synthesized in a yield of 38.1%.


Asunto(s)
Ácido Ascórbico/análogos & derivados , Endopeptidasas/metabolismo , Acilación , Ácido Ascórbico/química , Bacillus subtilis/enzimología , Catálisis , Dimetilformamida , Dioxanos , Endopeptidasas/química , Microbiología Industrial/métodos , Solventes , Agua
10.
Nat Prod Res ; 34(6): 838-842, 2020 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-30422002

RESUMEN

L-Ascorbic acid (AA), known as vitamin C, can form browning products by a non-enzymatic process during storage and the browning products cause deterioration of agricultural products. In the browning reaction, a red pigment, 2,2´-nitrilodi-2(2´)-deoxy-L-ascorbic acid ammonium salt (NDA), is generated from AA via L-scorbamic acid (SCA) as an intermediate. However, the biological activities of SCA and NDA have not yet been clarified. In this study, we assayed the antioxidant activities of SCA and NDA using ABTS radical cation and their neurite outgrowth-enhancing activities in PC12 cells. SCA showed stronger radical-scavenging activity than that of AA, while NDA hardly showed any activity. SCA and NDA enhanced the neurite outgrowth induced by dibutyryl cyclic AMP after their incorporation into cells in the same manner as that of AA. The results indicated that SCA has antioxidant activity and that SCA and NDA have neurite outgrowth-enhancing activity.


Asunto(s)
Antioxidantes/farmacología , Ácido Ascórbico/análogos & derivados , Ácido Ascórbico/química , Proyección Neuronal/efectos de los fármacos , Animales , Ácido Ascórbico/farmacología , Colorantes , Depuradores de Radicales Libres , Reacción de Maillard , Células PC12 , Ratas
11.
Carbohydr Res ; 346(15): 2511-4, 2011 Nov 08.
Artículo en Inglés | MEDLINE | ID: mdl-21903204

RESUMEN

6-O-Dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (6-sDode-AA-2G) was synthesized from 2-O-α-D-glucopyranosyl-L-ascorbic acid and lauric anhydride with a polymer catalyst, poly(4-vinylpyridine), in N,N-dimethylformamide without the introduction of protecting groups. The optimum reaction conditions enabled 6-sDode-AA-2G to be synthesized in a yield of 49.7%. The yield and the regioselectivity in this method were far superior to those in our previous method by using an enzyme. The polymer catalyst could be recycled more than five times without any significant activity loss.


Asunto(s)
Ácido Ascórbico/análogos & derivados , Formamidas/química , Glucósidos/síntesis química , Polivinilos/química , Acilación , Anhídridos/química , Ácido Ascórbico/síntesis química , Ácido Ascórbico/química , Catálisis , Técnicas de Química Sintética , Dimetilformamida , Cinética , Ácidos Láuricos/química , Solventes , Estereoisomerismo
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