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1.
J Agric Food Chem ; 70(8): 2695-2700, 2022 Mar 02.
Artículo en Inglés | MEDLINE | ID: mdl-35167297

RESUMEN

Kaempferol glycosides are functional components of jack bean. The chemical stability of kaempferol glycosides under simulated food processing conditions was evaluated in this study by subjecting the methanol extract and each compound to heat treatment. During the heat treatment, rearrangement of the anisoyl group on the rhamnose moiety of the kaempferol glycoside was observed, followed by hydrolysis upon long-term heat treatment. One of the two regioisomers produced under heating conditions showed higher α-glucosidase inhibitory activity than the dominant anisoyl kaempferol glycoside. This rearrangement reaction was also observed upon the heat treatment of methyl-3-O-anisoyl-rhamnose, with the rearrangement from the 3-position to the 2-position occurring preferentially. The approach adopted in this study can be used to design appropriate food processing conditions, which, in turn, will increase the functional value of foods.


Asunto(s)
Canavalia , Glicósidos , Canavalia/química , Glicósidos/química , Quempferoles/farmacología , alfa-Glucosidasas
2.
J Ethnopharmacol ; 282: 114618, 2022 Jan 10.
Artículo en Inglés | MEDLINE | ID: mdl-34508803

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Syzygium polyanthum (Wight) Walp leaves are traditionally used to cure diabetes in many regions of Indonesia. Traditional use involves boiling the leaves until the water is reduced to half volume, and then the decoction is taken 1-2 times daily. Despite several studies reporting the antidiabetic activity of this plant, bioactive compounds have not been well identified. AIM OF THE STUDY: Indonesia is one of the countries with the highest diabetes cases, particularly type 2 diabetes mellitus (T2DM). Few people have access to modern medicinal treatment; thus, the role of antidiabetic traditional medicine has become increasingly important. This research aimed to identify α-glucosidase inhibitors from S. polyathum leaves using a metabolomics approach. When the active compounds of S. polyathum are properly identified, the quality of the herb can be more easily controlled. MATERIALS AND METHODS: The dried leaves of S. polyanthum were extracted by a comprehensive extraction method using a solvent combination of n-hexane, acetone, and water in a gradient, resulting in a total of 42 fractions. All fractions were subjected to an in vitro α-glucosidase inhibition test and chemical profile analysis using Nuclear Magnetic Resonance (NMR) and high performance liquid chromatography (HPLC). Orthogonal projection least square (OPLS) analysis was used to correlate the two data to identify NMR signals, and HPLC chromatogram peaks correlated to the activity. 2D NMR and ultra-high-performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-HRMS) analyses were also used to give more precise compound identification. The activity of the identified active compounds was confirmed by an in silico technique. RESULTS AND DISCUSSION: The results of the α-glucosidase activity test showed that the most active fractions were obtained from solvents with medium polarity: Fractions 9 and 10 (F9 and F10), obtained from gradient acetone-water 4:1 and 3:2, respectively. The IC50 values of F9 and F10 were 24.8 and 31.8 µg/mL, respectively. NMR data showed that F9 had more intense and diverse signals in the aromatic region than F10. OPLS analysis results showed that some typical flavonoid signals abundant in F9 positively correlated with α-glucosidase activity. 2D NMR and UHPLC-HRMS analysis of F9 led to the conclusion that these signals could be attributed to myricetin-3-O-rhamnoside (myricitrin) and epigallocatechin-3-gallate (EGCG). In silico analysis confirmed these results, as myricitrin and EGCG had binding energies resembling acarbose as a positive control (-8.47, -8.19, and -10.13, respectively). CONCLUSIONS: NMR and HPLC-metabolomics successfully identified myricitrin and EGCG as α-glucosidase inhibitors from S. polyanthum leaves, and docking analysis validated their inhibitory activity. The results of this study justified the traditional use of S. polyanthum as an antidiabetes herbal.


Asunto(s)
Inhibidores de Glicósido Hidrolasas/farmacología , Metabolómica , Simulación del Acoplamiento Molecular , Extractos Vegetales/farmacología , Hojas de la Planta/química , Syzygium/química , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Fitoterapia , Extractos Vegetales/química , Relación Estructura-Actividad , alfa-Glucosidasas/metabolismo
3.
Molecules ; 25(11)2020 May 27.
Artículo en Inglés | MEDLINE | ID: mdl-32471071

RESUMEN

Although the intake of jack bean (Canavalia ensiformis (L.) DC.), an underutilized tropical legume, can potentially decrease the risk of several chronic diseases, not much effort has been directed at profiling the polyphenolics contained therein. Hence, this work aimed to identify and quantify the dominant jack bean polyphenolics, which are believed to have antioxidant and other bioactivities. Four major compounds were detected and identified as kaempferol glycosides with three or four glycoside units. Their structures were established based on UV-visible, 1d, 2D NMR, and HR-ESI-MS analyses. Specifically, kaempferol 3-O-a-l-rhamnopyranosyl (1®6)- b-d-glucopyranosyl (1®2)-b-d-galactopyranosyl-7-O-[3-O-o-anisoyl]-a-l-rhamnopyranoside was detected for the first time, while the other three compounds have already been described in plants other than jack bean. This new compound was found to have a higher a-glucosidase inhibition activity compared to acarbose.


Asunto(s)
Canavalia/química , Glucosidasas/antagonistas & inhibidores , Glicósidos/química , Flavonoles/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Espectrometría de Masa por Ionización de Electrospray
4.
Int J Food Sci ; 2020: 6097343, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32309421

RESUMEN

Increasing energy cost has driven the food canning industries to optimize their energy consumption in order to produce safe and shelf-stable foods efficiently. In the mushroom canning industry, energy efficiency is very critical to improve product (price) competitiveness. This research aimed at demonstrating total steam consumption to achieve the same sterility level (F 0-value) of canned mushroom by using different combinations of times and temperatures of retorting. Agaricus bisporus in brine contained in 300 × 407 cans was heat processed in a horizontal static retort. Three different retort temperatures (115, 121, and 130°C) and different operator processing times ranging from 2 to 97 minutes were employed to achieve different levels of F 0-values. Our results showed that at the same level of sterility, steam consumption inversely decreased with the increase of retort temperature. At the same F 0-value of 10 minutes, energy efficiency for up to 72.9% and 58.1% per batch of retorting was achieved by increasing the temperature from 115 to 130°C and 115 to 121°C, respectively. Since steam consumption is a major element of production costs in the canning industry, the selection of higher temperatures and shorter time of retorting will have a positive commercial impact due to the reduction of production costs.

5.
Int J Food Sci ; 2020: 9068326, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32047805

RESUMEN

Coleus amboinicus(Lour) (CA) has been reported to possess many pharmacological activities. In this study, evaluation of cytotoxicity using brine shrimp lethality bioassay and MTT assay using WiDr cell lines was carried out. The expression of several genes responsible for programmed cell death of the methanol extract of CA was also investigated. The morphology of the cells undergoing apoptosis was detected using Hoechst staining assay. The gene expression of BAX, BCL2, P53, Caspase 1, 7, 8, and 9 of treated samples with different concentrations (10, 15, 25 & 50 µg/ml) were measured with RT PCR. The phytochemical profiles were investigated using LC MS. The results showed that the lethality concentration (LC50) of methanol extract using brine shrimp was 34.545 µg/ml and the extract exhibited good antiproliferative activity against cancer cells WiDr with IC50 value (8.598 ± 2.68 µg/ml) as compared to standard drug 5-fluorouracil (IC50 value 1.839 ± 0.03 µg/ml). There was apoptotic evidences from the morphology of treated cells. The expressions of BAX,P53, and Caspase 9 were upregulated in lower concentration of the extract (10 and 15 µg/ml) but downregulated in higher concentration (25 and 50 µg/ml). BCL2 as anti-apoptotic gene was downregulated in all concentrations. Caspase 1 and Caspase 7 were upregulated in high concentration (25 and 50 µg/ml), but downregulated in lower concentrations. These data provide a mode of cell death for the methanol extract of CA in low concentrations corresponding to apoptosis with intrinsic pathway. Many valuable compounds identified including caffeic acid, rosmarinic acid, malic acid, eicosapentanoic acid, benserazide, alpha-linolenic acid, betaine, Salvanolic B, 4-hydroxibenzoic acid and firulic acid have been previously reported as being active agents against many cancer cells. This study suggested that CA might become an effective ingredient for health-beneficial foods to prevent colon cancer.

6.
Biosci Biotechnol Biochem ; 84(3): 598-605, 2020 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-31724491

RESUMEN

Red kidney beans (Phaseolus vulgaris L.) contain bioactive compounds that are known to exhibit antidiabetic effects via inhibition of α-glucosidase. However, information on the nonpolar components that exhibit antidiabetic activity is limited. Here, we report the isolation and structure determination of components with α-glucosidase inhibitory activity, which were obtained from the hexane extract of red kidney beans. Triacylglycerols (TAGs) were identified as the major components exhibiting inhibitory activity against α-glucosidase. The chemical structure of TAGs was determined by a combination of GC-MS and UPLC-MS/MS. The primary TAGs identified were LnLnLn (trilinolenin) and LnLLn (1,3-dilinolenoyl-2-linoleoyl glycerol). The major fatty acids present in these TAGs were α-linolenic acid (ω-3) and linoleic acid (ω-6). These TAGs were also found to inhibit the α-glucosidase activity in a similar fashion as acarbose. These results suggest that TAGs have potency as antidiabetics and support the potential suitability of red kidney beans for diabetes treatment.


Asunto(s)
Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Hexanos/química , Phaseolus/química , Triglicéridos/aislamiento & purificación , Cromatografía Liquida/métodos , Diabetes Mellitus/tratamiento farmacológico , Ácidos Grasos/análisis , Cromatografía de Gases y Espectrometría de Masas , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/uso terapéutico , Estructura Molecular , Espectrometría de Masas en Tándem , Triglicéridos/química
7.
Food Sci Biotechnol ; 25(Suppl 1): 157-161, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-30263501

RESUMEN

Food poisoning outbreaks frequently occur in many countries resulting in economic loss. A formula for calculation of economic loss due to food poisoning outbreaks in Indonesia was developed. Estimation of the loss was developed based on experiences in several countries. Related data were also collected from local health facilities, food industry officials, and other sources to improve the accuracy of the formula. Calculation of the economic loss was performed based on cases of food poisoning outbreaks recorded in 2013. Economic loss was estimated based on direct health-care costs, direct non-health-care costs, and indirect non-health-care costs. The economic loss of food poisoning outbreaks in Indonesia in 2013 was approximately US$ 78 million. The high-cost of economic loss due to food poisoning outbreaks suggests a need for additional and serious efforts for controlling all aspects of food safety.

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