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1.
Chem Biodivers ; : e202401331, 2024 Jun 21.
Artículo en Inglés | MEDLINE | ID: mdl-39031675

RESUMEN

The flowers of Yucca aloifolia ("flor de izote") are considered a millenary food in the Northeastern Highlands of Puebla, Mexico. The present investigation reports on the chemical and biological activities of the hydroalcoholic extract (YAHF) obtained from this edible source. HPLC-MS profiling revealed twenty bioactive phenolic compounds with chlorogenic acid (16.5 mg g-1 DW), quercetin (9.5 mg g-1 FW), and their glycosides (rutin and quercitrin), as well as caffeic acid (8.4 mg g-1 DW) and ferulic acid (7.9 mg g-1 DW) as major compounds dissolved in YAHF. Six metabolites had potent anti-lipase (IC50<100 µg mL-1) and anti-ornithine decarboxylase activity (IC50<100 µg mL-1), whereas thirteen exerted strong anti-alpha-glucosidase properties (IC50<100 µg mL-1). The evaluation of YAHF in mice subjected to standard oral glucose tolerance tests and prolonged administration of hypercaloric/atherogenic diet (30 days), unraveled their ability to improve glucose and lipid profiles. YAHF and six phenolic compounds significantly reduced DLD-1 cell viability (IC50, 117.9 µg mL-1) and avoided polyamine accumulation linked to anti-ornithine decarboxylase activity. YAHF and its twenty constituents exerted low toxicity in probiotics (>1000 µg mL-1) and 3T3 fibroblasts (>2.5 mg-mL-1), sustaining their safeness for human consumption.

2.
Chem Biodivers ; 21(6): e202301851, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38598722

RESUMEN

The 1H-NMR metabolomics profiling of six edible mushrooms consumed in the northeastern highlands of Puebla, Mexico is presented. These fungi were morpho- and molecularly identified as Infundibulicybe squamulosa, Amanita jacksonii, Lepista nuda, Russula delica, Russula brevipes, and Lactarius indigo. The chemical profiling confirmed the presence of eight essential amino acids and their derivatives, six organic acids, six nucleosides, low amounts of reducing sugars, and valuable nutraceuticals such as betaine, carnitine, glycero-3-phosphocholine and O-acetylcarnitine which were differentially determined and quantified in the six mushrooms by qNMR. Principal component analysis (PCA) and orthogonal projections to latent structures discriminant analysis (OPLS-DA) generated four different groups. Two of these groups were constituted by fungal species with phylogenic relationships whereas non-phylogenetic related species were separated from each other. The potential use of 1H-NMR metabolomics and chemometrics to group macromycetes and determine the nutritional and nutraceutical potential of these local foods is demonstrated.


Asunto(s)
Agaricales , Análisis de Componente Principal , Agaricales/química , Agaricales/metabolismo , México , Espectroscopía de Protones por Resonancia Magnética , Metabolómica , Aminoácidos/análisis , Aminoácidos/metabolismo , Análisis Discriminante , Filogenia
3.
Chem Biodivers ; 21(2): e202301689, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38224527

RESUMEN

Herein we describe the in situ inhibitory activity of three hybrid films (FL1, FL2, and FL3) against two wild strains of Colletotrichum gloeosporioides and Penicillium digitatum as causal agents of rot in Persian limes. The films FL2 and FL3 contained 1.0 and 1.3 % weight/volume Litsea glaucescens essential oil (LgEO) and significantly (p<0.05) delayed rot emergence in Persian limes caused by both pathogens up to 10 days. The physicochemical properties of LgEO and hybrid films were obtained, whereas detailed HPLC profiling revealed that fruit covered with these films significantly (p<0.01) preserved reducing sugars (sucrose, fructose, and glucose), organic acids (citric acid, ascorbic acid, malic acid, and oxalic acid), and flavonoids with nutraceutical activity (hesperidin, eriocitrin, naruritin, neohesperidin, diosmin, vitexin, rutin, and quercetin). This evidence sustains that the composites generated in this investigation improve the shelf life of Persian limes and conserve their nutraceutical content.


Asunto(s)
Citrus , Litsea , Aceites Volátiles , Antifúngicos/farmacología , Antifúngicos/análisis , Aceites Volátiles/análisis , Frutas/química
4.
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
5.
Chem Biodivers ; 20(10): e202301034, 2023 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-37616166

RESUMEN

We present the inhibitory properties of the R. pompana anthocyanin fraction (RPAF) and its major constituents on alpha-glucosidase (AG), pancreatic lipase (PL), HMG-CoA reductase, and ornithine decarboxylase (ODC). The effect of RPAF was also evaluated in ICR male mice subjected to oral glucose tolerance test (OGTT) and hypercaloric/atherogenic diet for 30 days. RP-HPLC/MS profiling revealed that RPAF contained five major anthocyanins and induced slight inhibition on PL and HMG-CoA reductase (IC50 , 245-338 µg mL-1 ) whereas strong activity on AG and ODC (IC50 , 130-133 µg mL-1 ) was observed. Kinetic studies and molecular docking with pelargonidin-3-O-rutinoside (P3R) on ODC, revealed changes in Km (0.9514-0.9746 mM) and Vmax (1.96-2.32 µmol mg-1 min-1 ) suggesting mixed inhibition and molecular interaction with two active sites of ODC. P3R showed antiproliferative activity (IC50, 46.5 µM) and decreased polyamine accumulation in DLD-1 cells. The results of OGTT confirmed that RPAF regulates postprandial glucose levels in diabetic animals which experienced a significant glucose depletion (30 %; p<0.001) from 30 to 120 min post-treatment. Prolonged supplementation of RPAF caused significant decrease (p<0.001) in plasma glucose, total cholesterol, LDL-c and triglycerides as well as significant increase (p<0.001) of HDL-c compared with normoglycemic untreated animals.

6.
Toxins (Basel) ; 15(2)2023 01 20.
Artículo en Inglés | MEDLINE | ID: mdl-36828416

RESUMEN

Lepidopterism caused by caterpillar contact is considered a public health problem around the world. The local and systemic responses of this pathology include short- and long-term inflammatory events. Although the proteolytic activity of the venoms from caterpillars is strongly associated with an inflammatory response in humans and murine models, fast and acute symptoms such as a burning sensation, itching, and pain should be related to the presence of low-weight hydrophilic molecules which easily influence cell metabolism. This investigation reports on the 1H-Nuclear Magnetic Resonance (NMR) profiling of the venom from the larva of Hylesia continua, a caterpillar linked to frequent cases of lepidopterism in the northern highlands of Puebla, Mexico. According to one-dimensional (1D) and two-dimensional (2D) NMR data, the venom of H. continua contained 19 compounds with proven pain-inducing activity (i.e., acetic acid, lactic acid, formic acid, succinic acid, 2-hydroxyglutaric acid, ethanol, and glutamate), inflammatory activity (i.e., cadaverine, putrescine, and acetoin), as well as natural immunosuppressive activity (i.e., O-phosphocholine and urocanic acid). The levels of the 19 compounds were calculated using quantitative-NMR (qNMR) and extensively discussed on the basis of their toxic properties which partially explain typical symptoms of lepidopterism caused by the larvae of H. continua. To the best of our knowledge, this is the first investigation reporting a complex mixture of small molecules with inflammatory properties dissolved in the venom of a lepidopteran larva.


Asunto(s)
Lepidópteros , Manduca , Mariposas Nocturnas , Humanos , Animales , Ratones , Ponzoñas , Espectroscopía de Protones por Resonancia Magnética , Prurito/etiología , Larva
7.
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
8.
Chem Biodivers ; 19(12): e202200745, 2022 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-36413469

RESUMEN

Celery is a vegetable widely consumed as a condiment to prepare diverse dishes around the world. Nevertheless, this plant is susceptible to the attack of several phytopathogens including those of the Fusarium genus which is translated into devastating losses for the production chain. Herein we report on the metabolic changes produced during the celery wilt caused by Fusarium oxysporum which was determined through untargeted 1 H-NMR metabolomics. The changes in the metabolite content of celery were measured at 16, 24, and 32 days post-inoculation using viable conidia obtained from the native F. oxysporum strain FO3. Our results demonstrated that the parasitic activity of the fungus reduced the endogenous levels of free sugars (fructose, galactose, glucose isomers, mannose, Myo-inositol, mannitol, and sucrose) amino acids (alanine, aspartate GABA, glutamate, glutamine, histidine, isoleucine, leucine, methionine, proline, threonine, tyrosine, and valine), nucleosides (adenosine, cytidine, guanosine, and uridine) and organic acids (citric acid, fumaric acid, malic acid, and succinic acid). Interestingly, the levels of tyrosine and tryptophan were triggered as a consequence of F. oxysporum infection. This tendency was correlated with an increase in the levels of chlorogenic acid, apiin, and apigenin derivatives, suggesting their involvement in the chemical defense of celery against fungal colonization. According to principal component analysis (PCA) and Orthogonal Projections to Latent Structures Discriminant Analysis (OPLS-DA) methanol was the main differential metabolite and it was considered as a new chemical marker associated with F. oxysporum infection. Our results demonstrate that infected celery plants dramatically reduced their nutritional and nutraceutical contents during Fusarium wilt after 32 days post-inoculation. However, these findings also suggest that the phenylpropanoid pathway is strongly related with the chemical defense of celery against F. oxysporum.


Asunto(s)
Apium , Fusarium , Verduras/metabolismo , Fusarium/metabolismo , Metaboloma , Tirosina , Enfermedades de las Plantas/microbiología
9.
Polymers (Basel) ; 14(10)2022 May 17.
Artículo en Inglés | MEDLINE | ID: mdl-35631932

RESUMEN

Hass avocadoes are one of the most popular fruits consumed worldwide because of their nutritional and nutraceutical content. Nevertheless, these fruits are susceptible to phytopathogen attacks that decrease fruit quality during the postharvest period. Herein we present the results of the in situ fungistatic activity of four hybrid films (FT1−FT4) manufactured with chitosan and different concentrations of the essential oil of thyme (TvEO). The films were evaluated as biodegradable materials to prevent fruit decay triggered by Clonostachys rosea which is considered an emergent phytopathogen of this crop. The in situ fungistatic strength, spectroscopic properties (FT-IR), optical features (transmittance/opacity), and consistency obtained by microscopic analysis (SEM), indicated that the films FT3 and FT4 possessed the best physicochemical properties to protect Hass avocadoes against the soft rot produced by C. rosea. Avocadoes treated with the films FT3 and FT4 significantly (p < 0.01) conserved fruit firmness and nutritional composition (protein, fat, fiber, and reducing sugars) as well as the nutraceutical content (oleic, palmitoleic, linoleic, and palmitic acids) of infected avocados for 21 days. Our results validate the potential use of the films FT3 and FT4 to prevent the soft rot caused by C. rosea and to improve the shelf life of Hass avocadoes.

10.
Chem Biodivers ; 19(1): e202100835, 2022 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34812593

RESUMEN

Cera pepper (Capsicum pubescens) is an exotic fruit considered as a rich source of nutraceuticals with known benefits for human health and also an economic resource for local producers in Mexico. The present investigation reports on the in vitro and in situ antifungal activity of the essential oil from Mentha piperita and its two major volatiles (menthol and menthone) against Fusarium sambucinum, which is a causal agent of soft rot in cera pepper. The application of these components in pepper fruits previously infected with F. sambucinum caused a significant delay (p<0.05) in the emergence of soft rot symptoms. This effect was reflected in the maintenance of pH and fruit firmness during a period of 10 days. The nutrimental content of the fruits (protein, fiber, fat and other proximate parameters) was conserved in the same period of time. The nutraceutical content of these fruits was estimated by the quantification of seven carotenoids (violaxanthin, cis-violaxanthin, luteoxanthin, antheraxanthin, lutein, zeaxanthin and ß-carotene), ascorbic acid and capsaicinoids (capsaicin and dihydrocapsaicin). According to our results, the essential oil from M. Piperita and its major volatiles exerted a preservative effect on these metabolites. Our findings demonstrated that the essential oil of M. Piperita and its major volatiles represent an ecological alternative for the control of fusariosis caused by F. sambucinum in cera peppers under postharvest conditions.


Asunto(s)
Capsicum/microbiología , Fusarium/efectos de los fármacos , Mentha piperita/química , Enfermedades de las Plantas/prevención & control , Aceites de Plantas/farmacología , Compuestos Orgánicos Volátiles/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Capsaicina/análisis , Capsaicina/aislamiento & purificación , Capsicum/crecimiento & desarrollo , Carotenoides/análisis , Carotenoides/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Frutas/química , Frutas/metabolismo , Concentración de Iones de Hidrógeno , Espectrometría de Masas , Mentha piperita/metabolismo , Enfermedades de las Plantas/microbiología , Extractos Vegetales/química , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Aceites de Plantas/química , Compuestos Orgánicos Volátiles/química , Compuestos Orgánicos Volátiles/aislamiento & purificación
11.
Plants (Basel) ; 10(2)2021 Feb 08.
Artículo en Inglés | MEDLINE | ID: mdl-33567633

RESUMEN

Brickellia veronicifolia is a native Asteraceae from Mexico that persists in fragmented habitats. This investigation reports the genetic and chemical diversity of B. veronicifolia. The diversity analysis based on iPBS markers showed an averaged Shannon index (S) of 0.3493, a Nei genetic diversity (h) of 0.2256, and a percentage of polymorphic loci average (P) of 80.7867%. The population structure obtained by AMOVA revealed that the highest variation found within populations was 94.58%. GC-MS profiling of six populations indicated that major volatiles were ß-caryophyllene (11.63%), spathulenol (12.85%), caryophyllene oxide (13.98%), α-cadinol (7.04%), cubedol (6.72%) and tau-muurolol (4.81%). Mantel tests suggested a statistically significant relationship between minor volatiles and geographical distance (r = 0.6163; p = 0.0470; p ˂ 0.05). Likewise, major volatiles showed a significant correlation with the soil pH (r = 0.6862; p = 0.0230) and maximum temperature (r = 0.4999; p = 0.0280). Our study suggests that the variation and genetic divergence of B. veronicifolia has no relationship with climatic parameters, whereas the volatiles are probably influenced by environmental factors and not by the genotype per se. Based on the characteristics of B. veronicifolia, this plant could be considered as a candidate for restoring fragmented shrublands in Mexico.

12.
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
13.
Chem Biodivers ; 17(10): e2000487, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32749064

RESUMEN

Dyssodia decipiens is one of the seven recognized species within the Dyssodia genus, which has economic and social relevance in Mexico. Herein, we report on the volatile characterization and pharmacological activity of D. decipiens. The essential oils (2017-2019) contained verbenone (30.8-60.9 %), limonene (5.6-35.5 %), ß-caryophyllene (7.8-19.8 %) and linalool (4.5-12.4 %) as major constituents along the studied years. Antifungal properties were probed on Candida albicans ATCC 90028, ATCC 10231 (fluconazole resistant) and five clinical isolates (IS1-IS5). Flower essential oils had the best anti-C. albicans activity (MIC 59.2-93.5 µg mL-1 ), and limonene (MIC 125.5-188.4 µg mL-1 ) and ß-caryophyllene (MIC 104.3-184.2 µg mL-1 ) were involved in this effect. SEM examination revealed that D. decipiens essential oils produced an evident lysis on the fungus. Mosquito repellent activity was demonstrated on Aedes aegypti, a vector of dengue, chikungunya and zika viruses. The repellent activity of leaf essential oils (20 %) was effective within 1-5 h post-treatment (>90 %) and it was stronger (p<0.01) than that of commercial DEET. The evaluation of the four major volatiles (10 % each) produced similar results to those of essential oils. Finally, leaf essential oils showed a moderate antiproliferative activity on the lines OVCAR-3 (LD50 56.5-85.7 µg mL-1 ), and verbenone (LD50 65.3 µg mL-1 ) and ß-caryophyllene (LD50 43.6 µg mL-1 ) were linked to this effect.


Asunto(s)
Aedes/efectos de los fármacos , Antifúngicos/farmacología , Antineoplásicos Fitogénicos/farmacología , Asteraceae/química , Candida albicans/efectos de los fármacos , Repelentes de Insectos/farmacología , Aceites Volátiles/farmacología , Animales , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Flores/química , Humanos , Repelentes de Insectos/química , Repelentes de Insectos/aislamiento & purificación , México , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación
14.
Phytochem Anal ; 31(4): 480-487, 2020 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-31908083

RESUMEN

INTRODUCTION: Nicotiana tabacum is a plant model intensively used in the bio-engineering pharmaceutical industry as a platform to produce drugs and therapeutic agents. Currently, no information regarding the non-targeted metabolome of transgenic tobacco containing recombinant regulatory sequences is available. OBJECTIVE: To compare the proton nuclear magnetic resonance (1 H-NMR) metabolomics profiling of a recombinant Nicotiana tabacum strain containing a promoter of a sesquiterpene cyclase from Capsicum annuum driving GUS expression, versus wild-type samples. Methodology The non-targeted 1 H-NMR metabolome was obtained and processed by principal component analysis (PCA) and orthogonal projection to latent structures discriminant analysis (OPLS-DA). The differential metabolites were quantified by quantitative NMR. RESULTS: PCA and OPLS-DA revealed 37 metabolites including 16 discriminant compounds for transgenic samples. Ethanol (0.4 mg g-1 ), the main differential compound, was exclusively detected in transgenic tobacco; however, high levels of formate (0.28 mg g-1 ) and acetate (0.3 mg g-1 ) were simultaneously observed in the same group of samples. Cembratriene-4,6-diol, an antitumour and neuroprotective compound, and capsidiol, a known phytoalexin, increased by about 30% in transgenic samples. In addition, the endogenous levels of the antioxidant caffeoylquinic acid isomers increased by 50% in comparison to those of wild-type tobaccos. CONCLUSION: Our results support the occurrence of metabolic differences between wild type and transgenic tobacco containing a promoter of a Capsicum sesquiterpene cyclase gene. Interestingly, the recombinant transgenic strain studied accumulated high amounts of added value compounds with biological activity.


Asunto(s)
Metabolómica , Nicotiana , Liasas de Carbono-Carbono , Espectroscopía de Resonancia Magnética
15.
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
16.
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
17.
Artículo en Inglés | LILACS | ID: biblio-915344

RESUMEN

The chemical composition of the seasonal essential oils (2015-2016) from the leaves and flowers of Zaluzania montagnifolia is presented. The chemical content of those oils showed quantitative and qualitative differences. Germacrene D (19.9-29.8%), camphor (12.4- 19.4%) and ß-caryophyllene (13.7-18.5%) were the most abundant volatiles in the leaves. The essential oils from the flowers contained high amounts of camphor (32.7-37.2%) limonene (19.8-24.9%) and germacrene D (3.2-7.3%). All the seasonal essential oils showed a potent in vitro inhibition against HMG-CoA reductase. The essential oils from flowers (IC50, 40.5-55.1 µg mL-1) showed better inhibition properties than those of leaves (IC50, 84.4-123.5 µg mL-1). Camphor (IC50, 72.5 µg mL-1) and borneol (IC50, 84.4 µg mL-1) exerted a non-competitive inhibition on the enzyme. Additionally, the hydrodistillates exhibited antibacterial activity against the phytopathogenic Pseudomonas syringae pv. tabaci TBR2004 (MIC, 62.7-76.5 µg mL-1) P. syringae pv. tomato DC3000 (MIC, 45.4-50.4 µg mL-1) and P. syringae pv. phaseolicola NPS3121 (MIC, 26.7-31.9 µg mL-1). Germacrene D (MIC, 35.4-66.2 µg mL-1) and ß-caryophyllene (MIC, 36.5-54.2 µg mL-1) were the strongest anti-Pseudomonas syringae agents.


Se presenta la composición química de los aceites esenciales estacionales (2015-2016) provenientes de hojas y flores de Zaluzania montagnifolia. El contenido químico de los aceites esenciales mostró diferencias cualitativas y cuantitativas. El germacreno D (19.9-29.8%), alcanfor (12.4-19.4%) y ß-cariofileno (13.7-18.5%) fueron los volátiles más abundantes en las hojas. Los aceites esenciales de las flores contuvieron altas concentraciones de alcanfor (32.7-37.2%), limoneno (19.8-24.9%) y germacreno D (3.2-7.3%). Todos los aceites esenciales estacionales mostraron una potente inhibición in vitro contra la HMG-CoA reductasa. Los aceites esenciales de las flores (IC50, 40.5-55.1 µg mL-1) mostraron mejores propiedades inhibitorias que aquellos de las hojas (IC50, 84.4-123.5 µg mL-1). El alcanfor (IC50, 72.5 µg mL-1) y el borneol (IC50, 84.4 µg mL-1) ejercieron una inhibición no competitiva sobre la enzima. Adicionalmente, los hidrodestilados exhibieron una actividad antibacterial contra los fitopatógenos Pseudomonas syringae pv. tabaci TBR2004 (MIC, 62.7-76.5 µg mL-1) P. syringae pv. tomato DC3000 (MIC, 45.4-50.4 µg mL-1) y P. syringae pv. phaseolicola NPS3121 (MIC, 26.7-31.9 µg mL-1). El germacreno D (MIC, 35.4-66.2 µg mL-1) y ß-cariofileno (MIC, 36.5-54.2 µg mL-1) fueron los agentes más fuertes contra los patovares de Pseudomonas syringae.


Asunto(s)
Aceites Volátiles/química , Inhibidores de Hidroximetilglutaril-CoA Reductasas/química , Asteraceae , Terpenos/análisis , Aceites Volátiles/farmacología , Cromatografía de Gases/métodos , Inhibidores de Hidroximetilglutaril-CoA Reductasas/farmacología , Hidroximetilglutaril-CoA Reductasas/efectos de los fármacos , Antibacterianos/farmacología
18.
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
19.
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.

20.
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
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