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1.
Chem Biodivers ; 20(12): e202301423, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37874748

RESUMEN

We present the inhibitory properties of the Solanum nigrescens anthocyanin fraction (SNAF) and its major constituents on alpha-glucosidase (AG), pancreatic lipase (PL), HMG-CoA reductase, and ornithine decarboxylase (ODC). The effect of SNAF was simultaneously evaluated in ICR male mice exposed to triglyceride charge test (TCT). HPLC-MS profiling revealed the presence cyanidin-3-O-rutinoside-5-glucoside (CRG), delphinidin-3-(p-coumaroyl)-rutinoside-5-glucoside (DCRG), and petunidin-3-(cis-p-coumaroyl)-rutinoside-5-glucoside (PCRG) as major constituents of the fraction. SNAF, CRG, and specially PCRG, induced strong non-competitive inhibition on PL (IC50 , 33-86 µg mL-1 ). The results of TCT confirmed their capacity to ameliorate (p <0.001) hypertriglyceridemia during postprandial and interdigestive stages. SNAF, CRG, DCRG, and PCRG caused negligible growth inhibition (MIC>600 µg mL-1 ) on beneficial bacteria whereas SNAF and DCRG exerted inhibitory activity on Helicobacter pylori ATCC 53504 (MIC,187-64 µg mL-1 ). Additional exploration revealed that SNAF and DCRG produced non-competitive activity on H. pylori urease, which facilitates bacterial growth under acidic conditions.


Asunto(s)
Helicobacter pylori , Hipertrigliceridemia , Solanum , Ratones , Animales , Antocianinas/farmacología , Antocianinas/análisis , Ratones Endogámicos ICR , Suplementos Dietéticos , Hipertrigliceridemia/tratamiento farmacológico , Glucósidos/farmacología , Cromatografía Líquida de Alta Presión
2.
Chem Biodivers ; 19(12): e202200667, 2022 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-36417317

RESUMEN

The leaves of Piper auritum Kunth ('Hoja Santa') have been consumed for centuries by native people of central and southern Mexico as a fresh vegetable or condiment. Herein we present the result of the 1 H-NMR metabolomics profiling of three accessions of P. auritum harvested in three different provinces of Mexico (Puebla, Tlaxcala, and Oaxaca). The volatile content associated with the flavoring properties of the plant was also determined by GC/MS. The non-targeted metabolome of these samples revealed that P. auritum is a source of free essential amino acids such as isoleucine, leucine, threonine, valine, histidine, phenylalanine, and tryptophan as well as organic acids, free monosaccharides, and valuable nutraceuticals such as trigonelline, Myo-inositol, betaine, and choline. Principal component analysis and orthogonal partial least squares discriminated analysis of the metabolites found in P. auritum revealed trigonelline as the main differential compound found in the three studied accessions, suggesting this metabolite as a possible chemical marker. According to these statistical approaches, 60 % of the differential metabolites were provided by Oaxaca samples, suggesting that leaves harvested in this province have better (p<0.05) nutritional properties than the other samples analyzed. Nevertheless, the high abundance of the anti-nutrient safrole (90 %) in the volatile fraction, advises the potential toxicity of P. auritum consumed in Oaxaca. On the other hand, samples harvested in the northern highlands of Puebla, contained the lowest levels of safrole (30 %) and acceptable levels of nutrients and nutraceuticals including choline. From the three groups of studied plants, those harvested in the northern highlands from Puebla, could be considered safer for human consumption than the other analyzed accessions.


Asunto(s)
Piper , Humanos , Piper/química , México , Plantas Comestibles , Safrol , Metabolómica
3.
Chem Biodivers ; 18(11): e2100611, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34547168

RESUMEN

Hernandulcin (HE) is a non-caloric sweetener synthesized by the Mexican medicinal plant Phyla scaberrima. Herein we present the results of HE production through cell suspensions of P. scaberrima as well as the influence of pH, temperature, biosynthetic precursors and potential elicitors to enhance HE accumulation. The incorporation of mevalonolactone (30-400 mg L-1 ) farnesol (30-400 mg L-1 ), AgNO3 (0.025-0.175 M), cellulase (5-60 mg L-1 ; 0.3 units/mg), chitin (20-140 mg L-1 ) and (+)-epi-α-bisabolol (300-210 mg L-1 ) to the cell suspensions, resulted in a differential accumulation of HE and biomass. Among elicitors assayed, chitin, cellulase and farnesol increased HE production from 93.2 to ∼160 mg L-1 but, (+)-epi-α-bisabolol (obtained by a synthetic biology approach) increased HE accumulation up to 182.7 mg L-1 . HE produced by the cell suspensions was evaluated against nine strains from six species of gastrointestinal bacteria revealing moderate antibacterial activity (MIC, 214-465 µg mL-1 ) against Staphylococcus aureus, Escherichia coli and Helicobacter pylori. Similarly, HE showed weak toxicity against Lactobacillus sp. and Bifidobacterium bifidum (>1 mg mL-1 ), suggesting a selective antimicrobial activity on some species of gut microbiota. According to our results, chitin and (+)-epi-α-bisabolol were the most effective molecules to enhance HE accumulation in cell suspensions of P. scaberrima.


Asunto(s)
Antibacterianos/farmacología , Sesquiterpenos/farmacología , Verbenaceae/química , Antibacterianos/química , Antibacterianos/metabolismo , Bifidobacterium bifidum/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Helicobacter pylori/efectos de los fármacos , Lactobacillus/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Sesquiterpenos/química , Sesquiterpenos/metabolismo , Staphylococcus aureus/efectos de los fármacos , Verbenaceae/citología
4.
Chem Biodivers ; 18(3): e2000941, 2021 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-33507621

RESUMEN

The essential oil from the annual plant Lepidium virginicum L. was chemically characterized in three consecutive years (2018-2020). The essential oils were evaluated in vitro and in situ on the causal agent of anthracnose in tamarillo fruits (Solanum betaceum). The main volatile constituents were phenylacetonitrile (>60 %), linalool (>10 %), limonene (>7 %) and α-terpineol (>5 %). The essential oil (MIC, 19-30 µg mL-1 ), phenylacetonitrile (MIC, 45 µg mL-1 ) and α-terpineol (MIC, 73 µg mL-1 ) caused a significant inhibition in the conidial viability from a wild strain of Colletotrichum acutatum, which was isolated and identified as a causal agent of anthracnose. The inoculation of conidia from C. acutatum in non-symptomatic tamarillo fruits, followed by the in situ treatment with different concentrations of the essential oil (>30 µg mL-1 ), phenylacetonitrile and α-terpineol, significantly (p<0.01) avoided the degradation of anthocyanins (delphinidin 3-O-rutinoside, cyanidin 3-O-rutinoside and pelargonidin 3-O-rutinoside) and carotenoids (ß-cryptoxanthin and ß-carotene) as well as retarded yellowing and necrosis triggered by anthracnose at least for 10 days. Our results suggest the potential use of the essential oil from L. virginicum as a natural component to preserve the nutraceutical content of tamarillo fruits against C. acutatum infection.


Asunto(s)
Antifúngicos/farmacología , Colletotrichum/efectos de los fármacos , Lepidium/química , Aceites Volátiles/farmacología , Enfermedades de las Plantas/prevención & control , Sustancias Protectoras/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Suplementos Dietéticos , Frutas/química , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificación , Solanum/química
5.
Chem Biodivers ; 16(2): e1800498, 2019 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-30512233

RESUMEN

Zanthoxylum limoncello is a native plant from southern Mexico which is used as a timber source, condiment and as a traditional medicine. Herein, we report on the volatile content of the leaf essential oil and its biological activities. The annual essential oils (2015-2018) contained volatile organic compounds which exhibited a moderate growth inhibitory activity against H. pylori ATCC 53504 (MIC 121.4-139.7 µg mL-1 ), 26695 (MIC 85.5-94.9 µg mL-1 ) and J99 (MIC 94.7-110.4 µg mL-1 ). These hydrodistillates contained 2-undecanone (31.6-36.8 %; MIC 185.3-199.2 µg mL-1 ) and 2-undecenal (25.1-35.7 %; MIC 144.8-111.3 µg mL-1 ) as the most abundant compounds which were partially involved in the anti-H. pylori activity. The human ornithine decarboxylase enzyme (ODC1), which shows increased activity in several cancer types, was non-competitively inhibited (Vmax 2.7>0.8 Kcat s-1 ) by the essential oil of Z. limoncello as well as by 2-undecanone and 2-undecenal in accordance to in vitro kinetic studies. In silico calculations strongly suggest that the carbonyl group of these oxygenated hydrocarbons interacts with both Asn319 and Ala39 at the subunit A of ODC1. Considering that Ala39 is located close to Asn44, a crucial amino acid of the ODC's allosteric site, the non-competitive inhibition of the enzyme by 2-undecanone and 2-undecenal is endorsed. Finally, the essential oil of Z. limoncello and its main volatiles showed a significant (p<0.01) and prolonged repellent effect against Aedes aegypti.


Asunto(s)
Aceites Volátiles/química , Zanthoxylum/química , Aedes/efectos de los fármacos , Animales , Sitios de Unión , Alcoholes Grasos/metabolismo , Alcoholes Grasos/farmacología , Helicobacter pylori/efectos de los fármacos , Humanos , Repelentes de Insectos/aislamiento & purificación , Repelentes de Insectos/farmacología , Cetonas/metabolismo , Cetonas/farmacología , México , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/farmacología , Ornitina Descarboxilasa/efectos de los fármacos , Hojas de la Planta/química
6.
Chem Biodivers ; 15(11): e1800354, 2018 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-30187618

RESUMEN

The present article describes the chemical composition and biological activities of the essential oils of B. glabrifolia leaves obtained in four consecutive years (2015-2018). The essential oils contained α-terpineol (17.9-29.7 %), α-terpinene (12.6-17.4 %), limonene (14.9-26.8 %) and ß-pinene (2.1-16.7 %) as the most abundant volatiles. The essential oils and these volatiles showed a significant adulticide activity (p<0.01; LC50 <100 µg mL-1 ) on the maize weevil (Sitophilus zeamais) with a 100 % mortality rate within a period of 5 h. Also, the essential oils showed a strong antibacterial activity on Enterococcus faecalis ATCC 29212 (MIC, 132.7-173.6 µg mL-1 ) and Helicobacter pylori ATCC 43504 (MIC, 74.8-199.2 µg mL-1 ). The assessment of the main volatiles revealed α-terpineol as the principal antibacterial agent (MIC, 78.6-149.7 µg mL-1 ). Similarly, the essential oils exhibited a substantial in vitro antiproliferative activity on the human prostate cancer cell lines PC-3 (LC50 , 15.2-19.4 µg mL-1 ), the human ovarian carcinoma cell lines OVCAR-3 (LC50 , 27.3-53.7 µg mL-1 ) and the myelogenous leukemia cell lines K-562 (LC50 , 32.4-75.9 µg mL-1 ). α-Terpineol (LC50 , 32.4-75.9 µg mL-1 ) exhibited the strongest antiproliferative effect on these cancer cell lines (LC50 , 22.4-48.1 µg mL-1 ).


Asunto(s)
Antibacterianos/farmacología , Antineoplásicos Fitogénicos/farmacología , Bursera/química , Insecticidas/farmacología , Aceites Volátiles/farmacología , Compuestos Orgánicos Volátiles/farmacología , Animales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Enterococcus faecalis/efectos de los fármacos , Helicobacter pylori/efectos de los fármacos , Humanos , Insecticidas/química , Insecticidas/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Hojas de la Planta/química , Relación Estructura-Actividad , Compuestos Orgánicos Volátiles/química , Compuestos Orgánicos Volátiles/aislamiento & purificación , Gorgojos/efectos de los fármacos
7.
Fitoterapia ; 128: 86-92, 2018 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-29777752

RESUMEN

This study reports on the volatile profile and pharmacological activities of the essential oil and resin from Bursera slechtendalii, an aromatic medicinal tree commercialized in southern Mexico. The essential oil contained 25 volatiles including p-cymen-8-ol (25.4-35.7%), n-hexyl hexanoate (6.8-17.6%) and n-octyl hexanoate (7.6-14.8%), whereas the crystallized resin contained 14 volatiles, including n-octyl acetate (29.6-34.2%), limonene (15.8-18.7%) and n-octyl butyrate (12.6-17-6%). The inhalation of vapors from the resin and essential oil caused a significant anxiolytic-like effect (p < .01) in ICR mice after 20 min of exposure at a dose of 50-150 mg L-1. The prolonged inhalation of the essential oil (for 40 days, for 15 min, twice a day) produced a significant decrease (p < .01) in total cholesterol and LDL-c content as well as an increase of HDL-c levels in the same murine model. Interestingly, levels of hepatic lipid hydroperoxide decreased, whereas the hepatic activity of superoxide dismutase and glutathione peroxidase was significantly enhanced (P < .05). The detection of p-cymen-8-ol and n-octyl acetate in the plasma of mice strongly suggests their bioavailability and possible role in the biological activities described herein. Also, both the resin and essential oil from B. slechtendalii, as well as their main volatiles, showed a potent repellence activity against Aedes aegypti (p < .01).


Asunto(s)
Bursera/química , Aceites Volátiles/química , Resinas de Plantas/química , Administración por Inhalación , Animales , Ansiolíticos , Repelentes de Insectos , Lípidos/sangre , Hígado/efectos de los fármacos , México , Ratones Endogámicos ICR , Aceites Volátiles/farmacología , Plantas Medicinales/química , Resinas de Plantas/farmacología
8.
Bol. latinoam. Caribe plantas med. aromát ; 16(5): 463-470, sept. 2017. tab, graf
Artículo en Inglés | LILACS | ID: biblio-912583

RESUMEN

The chemical composition of the essential oil and carotenoid content of the parasitic plant Cuscuta mitraeformis are described for the first time. The essential oil was analyzed by GC-FID and GC-MS revealing nonanal (24.6%) as the main constituent followed by thymol (16.5%) and eugenol (7.5%). The total carotenoid content (130 mg 100 g-1 FW) was determined by HPLC-DAD. The carotenoid fraction contained ß-carotene (76.4 mg 100 g-1 FW) and lutein (18.9 mg 100 g-1 FW) as the most abundant compounds. A weak antioxidant activity was observed by the essential oil against DPPH radical (IC50, 1.4 mg mL-1), whereas a strong antioxidant activity was determined for the carotenoid fraction (IC50, 60.1 µg mL-1). The essential oil inhibited the growth of Clavibacter michiganensis, Pseudomonas syringae pv. tomato and Erwinia carotovora with minimum inhibitory concentrations of 122.5, 184.5, 234.2 µg mL-1, respectively.


La composición química del aceite esencial y el contenido de carotenoides de la planta parásita Cuscuta mitraeformis se describen por primera vez. El aceite esencial fue analizado por GC-FID y GC-MS siendo el nonanal (24.6%) el constituyente principal seguido del timol (16.5%) y el eugenol (7.5%). El contenido total de carotenoides (130 mg 100 g-1 PF) fue determinado por HPLC-DAD. La fracción de carotenoides contuvo ß-caroteno (76.4 mg 100 g-1 PF) y luteína (18.9 mg 100 g-1 PF) como compuestos mayoritarios. Fue observada una actividad antioxidante débil por parte del aceite esencial frente al radical DPPH (IC50, 1.4 mg mL-1), mientras que una fuerte actividad antioxidante fue determinada para la fracción de carotenoides (IC50, 60.1 µg mL-1). El aceite esencial inhibió el crecimiento de Clavibacter michiganensis, Pseudomonas syringae pv. tomato y Erwinia carotovora con una concentración mínima inhibitoria de 122.5, 184.5, 234.2 µg mL-1, respectivamente.


Asunto(s)
Aceites Volátiles/farmacología , Aceites Volátiles/química , Cuscuta/química , Antibacterianos/farmacología , Antioxidantes/farmacología , Carotenoides/análisis , Cromatografía de Gases/métodos , Cromatografía Líquida de Alta Presión
9.
J Food Sci Technol ; 54(6): 1484-1490, 2017 May.
Artículo en Inglés | MEDLINE | ID: mdl-28559607

RESUMEN

Begonia nelumbiifolia is a traditional edible plant consumed and commercialized in the northern highlands of Puebla, México. The present study reports the seasonal variation in proximate analysis as well as organic acids, carotenoids and flavonoids content in both leaves and stalks of this plant. The stalks contained low concentrations of protein (~3%), fiber (~1.5%) and nitrogen free extract (~0.26%) during the time of study. Both organs showed contents of oxalic acid (91-103 mg 100 g-1 FW), ascorbic acid (50-65 mg 100 g-1 FW), lutein (1-2.5 mg 100 g-1 FW), ß-carotene (1-3 mg 100 g-1 FW), quercetin (1.3-2.7 mg 100 g-1 DW) and rutin (0.5-1.7 mg 100 g-1 DW). Antioxidant activity against DPPH was observed by the stalk extracts from 30% methanol (IC50, 0.21-0.37 mg L-1), pure methanol (IC50, 0.14-0.21 mg L-1) and hexane: acetone (IC50, 0.77-1.21 mg L-1). In vitro anti-HMG-CoA reductase (IC50, 0.07-0.36 mg L-1) and anti-alpha-glucosidase (IC50, 0.28-0.43 mg L-1) activities were observed in extracts from the edible stalks from pure methanol and 30% methanol. The leaf extracts from 30% methanol inhibited the growth of Pseudomonas syringae pv. tabaci TBR2004 (MIC, 254 µg mL-1), P. syringae pv. tomato DC3000 (MIC, 423 µg mL-1), P. syringae pv. glycinea (MIC, 605 µg mL-1) and Clavibacter michiganensis AB299158 (MIC, 162 µg mL-1). B. nelumbiifolia contained valuable phytochemicals associated to nutraceutical and biological properties. However, the consumption of the fresh stalks must be carefully considered because of the high oxalate content.

10.
Biol Res ; 46(2): 153-60, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23959013

RESUMEN

We report the results of in vitro anti-lipase and antioxidant assays using crude ethanolic extracts from 30 plants grown in Oaxaca, México. Anti-lipase tests were performed by using porcine pancreatic lipase (PPL) [EC 3.1.1.3] from Affymetrix/USB. The extracts of Solanum erianthum, Salvia microphylla, Brungmansia suaveolens and Cuphea aequipetala showed up to 60% PPL inhibition. The effect of these extracts on the kinetic parameters of PPL (Km= 0.36 mM, and Vmax=0.085 mM min -1) revealed that the alcoholic preparations of S. erianthum and C. aequipetala engendered a non-competitive inhibition (Vmax=0.055 mM min -1; Vmax= 0.053 mM min -1), whereas those of S. microphylla and B. suaveolens produced a mixed inhibition (Km= 0.567 mM, Vmax=0.051 mM min _1; Km=0.643 mM, Vmax= 0.042 mM min ¹). In addition to these findings, seven extracts from different plants were able to inhibit PPL in the range of 30-50%. Antioxidant tests against 2,2-Diphenyl-1-picryl hydrazyl (DPPH) confirmed that Arctostaphylos pungens, Gnaphalium roseum, Crotalaria pumila, Cuphea aequipetala, Rhus chondroloma, and Satureja laevigata possess relevant antioxidant activity (IC(5)0=50-80 µg mL¹). The general composition of the most effective ethanolic extracts was obtained in order to confirm their known chemistry reported by previous works. Comprehensive chemical analysis of the ethanolic extracts and their poisoning effects suggests that S. microphylla, C. aequipetala and A. pungens could be considered as the best sources with both desired properties.


Asunto(s)
Antioxidantes/farmacología , Lipasa/antagonistas & inhibidores , Obesidad/prevención & control , Estrés Oxidativo/efectos de los fármacos , Fitoterapia , Extractos Vegetales/farmacología , Plantas Medicinales/química , Medicina Tradicional , México , Nefelometría y Turbidimetría/métodos
11.
Biol. Res ; 46(2): 153-160, 2013. graf, tab
Artículo en Inglés | LILACS | ID: lil-683992

RESUMEN

We report the results of in vitro anti-lipase and antioxidant assays using crude ethanolic extracts from 30 plants grown in Oaxaca, México. Anti-lipase tests were performed by using porcine pancreatic lipase (PPL) [EC 3.1.1.3] from Affymetrix/USB. The extracts of Solanum erianthum, Salvia microphylla, Brungmansia suaveolens and Cuphea aequipetala showed up to 60% PPL inhibition. The effect of these extracts on the kinetic parameters of PPL (Km= 0.36 mM, and Vmax=0.085 mM min -1) revealed that the alcoholic preparations of S. erianthum and C. aequipetala engendered a non-competitive inhibition (Vmax=0.055 mM min -1; Vmax= 0.053 mM min -1), whereas those of S. microphylla and B. suaveolens produced a mixed inhibition (Km= 0.567 mM, Vmax=0.051 mM min _1; Km=0.643 mM, Vmax= 0.042 mM min ¹). In addition to these findings, seven extracts from different plants were able to inhibit PPL in the range of 30-50%. Antioxidant tests against 2,2-Diphenyl-1-picryl hydrazyl (DPPH) confirmed that Arctostaphylos pungens, Gnaphalium roseum, Crotalaria pumila, Cuphea aequipetala, Rhus chondroloma, and Satureja laevigata possess relevant antioxidant activity (IC(5)0=50-80 μg mL¹). The general composition of the most effective ethanolic extracts was obtained in order to confirm their known chemistry reported by previous works. Comprehensive chemical analysis of the ethanolic extracts and their poisoning effects suggests that S. microphylla, C. aequipetala and A. pungens could be considered as the best sources with both desired properties.


Asunto(s)
Antioxidantes/farmacología , Lipasa/antagonistas & inhibidores , Obesidad/prevención & control , Estrés Oxidativo/efectos de los fármacos , Fitoterapia , Extractos Vegetales/farmacología , Plantas Medicinales/química , Medicina Tradicional , México , Nefelometría y Turbidimetría/métodos
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