Yolanda Rios Gomez

PhD
Professor (Full)
Universidad Autónoma del Estad... · Centro de Investigaciones Químicas (CIQ)

Publications

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    Industrial Crops and Products. 12/2014; 62:166-172.
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    ABSTRACT: Non-insulin dependent diabetes mellitus is a multifactorial disease that links different metabolic routes; a point of convergence is the enzyme PTP-1B which turns off insulin and leptin receptors involved in glucose and lipid metabolism, respectively. Pentacyclic acid triterpenes such as oleanolic acid (OA) have proved to be excellent PTP-1B inhibitors, thus, the purpose of current work was to generate a series of derivatives that improve the pharmacological effect of OA. Our findings suggest that the presence of the carboxylic acid and/or its corresponding reduction product carbinol derivative (H-bond donor) in C-28 is required to maintain the inhibitory activity; moreover, this is further enhanced by ester or ether formation on C-3. The most active derivatives were cinnamoyl ester (6) and ethyl ether (10). Compound 6 showed potent in vitro inhibitory activity and significantly decrease of blood glucose levels on in vivo experiments. Meanwhile, 10 showed contrasting outcomes, since it was the compound with higher inhibitory activity and selectivity over PTP-1B and has improved interaction with site B, according with docking studies, the in vivo antidiabetic effect was similar to oleanolic acid. In conclusion, oleanolic acid derivatives have revealed an enhanced inhibitory effect over PTP-1B activity by increasing molecular interactions with either catalytic or allosteric sites and producing a hypoglycaemic effect on non insulin dependent diabetes mellitus rat model.
    European Journal of Medicinal Chemistry 09/2014; 87C:316-327. · 3.50 Impact Factor
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    ABSTRACT: Stansin 6 a tetrasaccharide resin glycoside isolated from the root of Ipomoea stans was evaluated as anticonvulsant and neuroprotective in kainic acid-induced seizures of rats. Intraperitoneal injection of kainic acid (10mg/kg) induced typical behavioral seizures such as wet dog shakes and limbic seizures, and histopathological changes in the hippocampus (degeneration and loss of pyramidal cells in CA1 to CA4 areas). Stansin 6 (10-80mg/kg) had no effect on the behavior of rats and did not induce hippocampal damage. Pretreatment with stansin 6 inhibited convulsions in rats from kainic acid-induced seizures, reduced the degeneration pattern in the CA3 region, decreased astrocytic reactivity, and reduced the expression of IL-1β and TNF-α induced by kainic acid. These results suggest that stansin 6 possesses neuroprotective and anticonvulsant activities.
    Bioorganic & Medicinal Chemistry Letters 05/2014; 24(15):3541-3545. · 2.34 Impact Factor
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    ABSTRACT: Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (Emax = 100%), where compound 2 (42 μM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.
    European journal of medicinal chemistry 03/2014; 77C:400-408. · 3.27 Impact Factor
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    Rios Aldana-Llanos Valdes-Estrada Ochoa M Y L M E M G Valladares-Cisneros M.G.
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    ABSTRACT: The need for new bioinsecticidal compounds motivates the study of natural products. Therefore, we studied the activity of Crescentia alata Kuth (Lamiales: Bignoniaceae) against Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae). We showed that C. alata has bioinsectidal activity. After 7 days of exposure to C. alata fractions in the diet at 200 ppm, fractions 3, 4 and 7 caused 90.7% weight loss in the larvae, and at 100 ppm, fractions 2, 4, 7 and 8 caused 90.1% weight loss with respect to the control. After 14 days of exposure to fractions 4 and 7 at 200, 100, and 50 ppm, the larvae had lost 94% of their weight compared to the control. There were large differences in larval mortalities between treatments, and fractions 5 and 6 at 200, 100, and 50 ppm induced the highest mortalities, which ranged from 65 to 80%. Possibly the iridoids identified from the C. alata fruit fractions are responsible for the antifeedant activity and mortality of S. frugiperda. This is the first report of C. alata fractions being evaluated as biocides of S. frugiperda.
    Florida Entomologist 01/2014; 97(2):770-777. · 1.16 Impact Factor
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    María Yolanda Rios, Horacio F. Olivo
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    ABSTRACT: Alkamides are a group of bioactive natural compounds showing broad structural variability and an important range of biological activities, such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal, diuretic, pungent, analgesic, cannabimimetic, and antioxidant activities. These natural products are also involved in the potentiation of some antibiotics and the inhibition of prostaglandin biosynthesis, RNA synthesis, and the arachidonic acid metabolism. Many plant species containing alkamides have been used in traditional medicine by different civilizations around the world. Alkamides represent a class of lipidic compounds structurally related to animal endocannabinoids. Based on the structural similarity of these compounds to anandamide (N-arachidonoylethanolamine), an endogenous cannabinoid cerebral neurotransmitter, alkamides are highly active in the central nervous system. Despite their several biological activities, their immunomodulatory and analgesic properties are most important therapeutic applications.
    01/2014: pages 79-121; , ISBN: 978-0-444-63430-6
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    ABSTRACT: Flourensia genus (Asteraceae) includes about 40 species of resinous shrubs characterized for its leaves surfaces covered with a characteristic oil-fatty film. These plants grow in arid and semiarid regions throughout the American continent. Plants belonging to Flourensia genus show important activities, like insecticidal (García et al., 2007), insect antifeedant (Diaz Napal et al., 2009; Faini et al., 1997a), antibacterial (Joray et al., 2011), antifungal (Jasso de Rodríguez et al., 2012), herbicidal, in-hibitors on the germination and in growth of plants (Diaz Napal et al., 2009; Silva et al., 2012) and as tyrosinase inhibitors (Chiari et al., 2010). F. resinosa S.F. Blake (Asteraceae) is a dominant plant at the semi-desertic zone known as "Cerro del Señor" (20 26 0 10 00 N, 99 05 0 42 00 W, 1915 m above sea level), Ixmiquilpan, Hidalgo, where its aerial parts were collected and identified in October 27, 2007 by M.C. Ramiro Ríos-Gómez from the Facultad de Estudios Superiores Zaragoza, UNAM, México. A voucher specimen (number 11839) was deposited at FESZ Herbarium, UNAM. 2. Previous work F. resinosa is an evergreen shrub up to 2.5 m growing in semiarid environments in central regions of Mexico. As its name suggests, this plant secretes large amounts of resin, which is deposited on its leaves and aerial parts. This resin contains
    Biochemical Systematics and Ecology 12/2013; 51:240–242. · 1.15 Impact Factor
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    ABSTRACT: Context: Heliopsis longipes (A. Gray) Blake (Asteraceae), commonly known in Mexico as "chilcuage" or "chilcuan", is widely used as an analgesic and anesthetic agent. Affinin, the major metabolite of this plant, and the ethanol extract of the plant have shown antinociceptive properties in mice. H. longipes plant produces a complex mixture of antioxidant chlorophylls and polyamines as well as a number of possible antimutagens. Objective: The current study evaluated the potential utilization of the natural product affinin isolated from H. longipes ethanol extract as an antimutagenic and possibly anticarcinogenic agent. Materials and methods: The Ames assay was used to assess the mutagenic properties of affinin (12.5, 25 and 50 µg/plate) that was added to several mutagens with or without S9 metabolic activation in Salmonella typhimurium (TA98, TA100 and TA102 strains). Results: Heliopsis longipes extract and affinin were not toxic as a reduction in the number of His(+) revertant bacteria colonies. Affinin (25 and 50 µg/plate) significantly reduced the frameshift mutations that were generated by 2-aminoanthracene (2AA) (40%) and reduced the oxidative DNA damage generated by norfloxacin (NOR) (37-50%). Affinin possessed antioxidant properties that were able to reduce 2AA- and NOR-induced mutations in S. typhimurium TA98 and TA102, respectively. Discussion and conclusion: Affinin, the principal metabolite of H. longipes, is not mutagenic and possesses antimutagenic activity. These plants are currently used to treat some pain symptoms in Mexico; and antimutagen activity determined could be important to treat some pain symptoms related to antiradical activity.
    Pharmaceutical Biology 08/2013; 51(8):1035-1039. · 1.21 Impact Factor
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    ABSTRACT: Morolic (1) and moronic (2) acids are the main constituents of acetonic extract from Phoradendron reichenbachianum (Loranthaceae), a medicinal plant used in Mexico for the treatment of diabetes. The aim of the current study was to establish the sub-acute antidiabetic and antihyperlipidemic effects of compounds 1 and 2 over non insulin-dependent diabetic rat model. Also, to determine the antihyperglycemic action on normoglycemic rats by oral glucose tolerance test. Daily-administered morolic (1) and moronic (2) acids (50mg/kg) significantly lowered the blood glucose levels at 60% since first day until tenth day after treatment than untreated group (p<0.05). Moreover, analyzed blood samples obtained from diabetic rats indicated that both compounds diminished plasmatic concentration of cholesterol (CHO) and triglycerides (TG), returning them to normal levels (p<0.05). Also, pretreatment with 50mg/kg of each compound induced significant antihyperglycemic effect after glucose and sucrose loading (2g/kg) compared with control group (p<0.05). In vitro studies showed that compounds 1 and 2 induced inhibition of 11β-HSD 1 activity at 10μM. However, in silico analysis of the pentaclyclic triterpenic acids on 11β-HSD 1 revealed that all compounds had high docking scores and important interactions with the catalytic site allowing them to inhibit 11β-HSD 1 enzyme. In conclusion, morolic and moronic acids have shown sustained antidiabetic and antihyperglycemic action possibly mediated by an insulin sensitization with consequent changes of glucose, cholesterol and triglycerides, in part mediated by inhibition of 11β-HSD 1 as indicated by in vitro and in silico studies.
    Phytomedicine: international journal of phytotherapy and phytopharmacology 02/2013; · 2.97 Impact Factor
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    ABSTRACT: Phoradendron brachystachyum is a hemiparasitic plant widely distributed in México that belongs to the Viscaceae family. It has been commonly used in folk medicine as a substitute for the European mistletoe. In this chemical study, morolic acid was isolated as the major component (47.54% of the total composition of acetone extract) of this plant. In addition, 19 known compounds were identified: β-sitosteryl and stigmasteryl linoleates, β-sitosterol, stigmasterol, triacontanol, squalene, α- and β-amyrin, lupeol, lupenone, betulin aldehyde, betulon aldehyde, oleanolic aldehyde, betulinic acid, betulonic acid, moronic acid, morolic acid, oleanolic acid, flavonoids acacetin and acacetin 7-methyl ether. There have been no previous reports in the literature on the chemical composition of this potential natural source of hypoglycaemic and antihypertensive compounds.
    Natural Product Research 02/2013; 27(2):130-136. · 1.03 Impact Factor
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    M Angeles Ramírez-Cisneros, Yolanda Rios Gomez, Ramiro Ríos-Gómez, A Berenice Aguilar-Guadarrama
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    ABSTRACT: Krameria pauciflora is a species belonging to the Krameriaceae family. It has been used to treat inflammatory disorders in folkloric Mexican medicine; however, chemistry and pharmacological studies have not been carried out on this species. In this work, from the dichloromethane root extract of K. pauciflora, five cycloartane-type triterpenoids were isolated: cyclomargenyl-3-O-β-caffeoyl ester (1), cyclomargenyl-3-O-β-feruloyl ester (2), cyclomargenyl-3-O-β-coumaroyl ester (3), cyclomargenol (4, polysthicol), and cyclomargenone (5). Additionally, the lignane 6'-methoxyrataniaphenol was isolated. To the best of our knowledge, compounds 1-3 are new natural products, whereas compounds 4 and 5 are isolated for the first time in the Krameria genus and the Krameriaceae family. The structures of all of these compounds were established by 1D and 2D NMR spectroscopy including 1H, 13C, DEPT, COSY, HSQC, and HMBC experiments, as well as by EI mass spectrometry. There is an incomplete previous report about the spectroscopic data of compounds 4 and 5. However, in this work, a complete and unambiguous assignation has been realized. Due to the traditional use of this plant and other species from this genus, such as K. lappacea, cycloartanes isolated herein were evaluated by their inhibition of phospholipase A2, cyclooxygenase-1, and cyclooxygenase-2 enzymes. Cyclomargenyl-3-O-β-caffeoyl ester (1) showed inhibition of phospholipase A2, cyclooxygenase-1, and cyclooxygenase-2 target enzymes for nonsteroidal anti-inflammatory drugs. Both cyclooxygenases were inhibited by cyclomargenol (4); however, cyclomargenyl-3-O-β-feruloyl ester (2) showed inhibition only on cyclooxygenase-1.
    Planta Medica 11/2012; 78(18):1942. · 2.35 Impact Factor
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    Sugey Lopez, Virginia Flores, Yolanda Rios
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    ABSTRACT: Los muérdagos eran considerados plantas mágicas y sagradas tanto por los pueblos occidentales como por los europeos antiguos y, hasta nuestros días, continúan alimentando muchos mitos en torno suyo. Según los primeros cristianos, el muérdago fue el árbol del que se extrajo la madera para hacer la cruz en la que murió Jesús; vergüenza que provocó su encogimiento y su transformación en una maleza parásita de otros árboles.
    Ciencia y desarrollo 11/2012;
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    ABSTRACT: Several natural and synthetic polypeptides possess important antimalarial activity. Shorter peptides with potent antimalarial activity have also been described, among them linear di-, tri-, tetra- and pentapeptides and their cyclic analogs. In an attempt to find dipeptides with antimalarial activities we show that linear and cyclic dipeptides, the latter known as diketopiperazines, still retain the fundamental core to preserve antimalarial activity. Thirteen linear dipeptides and ten diketopiperazines were investigated. Eight linear dipeptides showed IC(50) values between 2.78 and 7.07μM, while eight diketopiperazines were also active with IC(50) values between 2.26 and 4.26μM on Plasmodium berghei schizont cultures.
    Bioorganic & medicinal chemistry letters 10/2012; · 2.65 Impact Factor
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    ABSTRACT: Bioassay guided fractionation of an antimycobacterial extract of Foeniculum vulgare var dulce (Apiaceae) led to the isolation and characterization of 5-hydroxyfurano-coumarin. The chemical structure of this compound was elucidated by 1 H and 13 C (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy. In addition, the active fractions were analyzed by GC-MS and seventy eight compounds were identified; the major compounds were 1,3-benzenediol, 1-methoxycyclohexene, o-cymene, sorbic acid, 2-hydroxy-3-methyl-2-cyclopenten-1-one, estragole, limonene-10-ol and 3-methyl-2-cyclopenten-1-one. Twenty compounds identified in the active fractions were tested against one sensitive and three MDR strains of Mycobacterium tuberculosis using the Alamar Blue microassay. Compounds that showed some degree of antimycobacterial activity against all strains tested were the following: linoleic acid (MIC 100 µg/mL), oleic acid (MIC 100 µg/mL), 1,3-benzenediol (MIC 100–200 µg/mL), undecanal (MIC 50–200 µg/mL), and 2,4-undecadienal (MIC 25–50 µg/mL), the last being the most active compound. To our knowledge, this is the first report of the presence of 5-hydroxy-furanocoumarin in F. vulgare. 8472 Keywords: Foeniculum vulgare (F. vulgare); Mycobacterium tuberculosis; multidrug resistant (MDR); 5-hydroxyfuranocoumarin
    Molecules 06/2012; 7:8471-8482. · 2.43 Impact Factor
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    ABSTRACT: The aim of the current study was to investigate the vasorelaxant activity of five structurally-related triterpenic acids namely ursolic (1), moronic (2), morolic (3), betulinic (4) and 3,4-seco-olean-18-ene-3,28-dioic (5) acids. The vasorelaxant effect of compounds 1-5 were determined on endothelium-denuded and endothelium-intact rat aortic rings pre-contracted with noradrenaline (0.1 μM). All compounds showed significant relaxant effect on endothelium-intact vessels in a concentration-dependent manner (p<0.05). Ursolic, moronic and betulinic acids were the most potent vasorelaxant agents with 11.7, 16.11 and 58.46 μM, respectively. Since vasorelaxation was blocked by L-NAME, while indomethacin did not inhibit the effect, endothelium-derived nitric oxide seems to be involved in triterpenic 2 and 3 mode of action. Compounds 1-5 were docked with a crystal structure of eNOS. Triterpenes 1-5 showed calculated affinity with eNOS in the C1 and C2 binding pockets, near the catalytic site; Ser248 and Asp480 are the residues that make hydrogen bonds with the triterpene compounds.
    Fitoterapia 05/2012; 83(6):1023-9. · 2.23 Impact Factor
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    ABSTRACT: The aim of the present study was to examine the antihypertensive effect of methanolic extract from Lepechinia caulescens (MELc) and to determine the thoracic aorta reactivity after long-term treatment with MELc. Results showed that MELc at 38 and 120 mg/Kg induced a significant decrease of heart rate (HR), systolic blood pressure (SBP) and diastolic blood pressure (DBP) in comparison with control and similar than captopril (30 mg/Kg). Also, MELc (120 mg/Kg) induced a long-term antihypertensive activity when still down SBP and DBP from fifth day until the end of experiment. Vascular reactivity of vessels from extract-treated animals was improved when were stimulated with carbachol and sodium nitroprusside. However, treatment with noradrenaline enhanced contractile response on these preparations. In conclusion, MELc produced significant antihypertensive and bradycardic effects that may be related with an activation of NO/cGMP pathway
    Phytopharmacology. 05/2012; 2(1):170-178.
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    ABSTRACT: Strategy, Management and Health PolicyEnabling Technology, Genomics, ProteomicsPreclinical ResearchPreclinical Development Toxicology, Formulation Drug Delivery, PharmacokineticsClinical Development Phases I-III Regulatory, Quality, ManufacturingPostmarketing Phase IVHeliopsis longipes is a popular medicinal plant in Mexico. One of the main constituents that can be extracted from H. longipes is affinin (N-isobutylamide). However, available information regarding this compound is scarce, and there is only a single report related to the effect of affinin on the central nervous system. Affinin extracted from H. longipes was evaluated for its psychopharmacological activity in several models and for its safety. H. longipes extract and affinin demonstrated antinociceptive effect, modified anxiety behavior and prolonged the time of sodium pentobarbital-induced hypnosis. Affinin elicited these activities at high doses. Both the extract and affinin decreased the time of clonic and tonic PTZ-induced seizures. In the Ames test, neither the extract nor affinin induced mutations in the Salmonella typhimurium strains TA98 and TA100 or TA102 with or without the S9 microsomal fraction. Lethal dose 50 values in mice suggest that the H. longipes extract may contain sedative principles with potential anxiolytic activity; however, it may also increase convulsive activity.
    Drug Development Research 05/2012; 73(3). · 0.87 Impact Factor
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    Mar'ia Yolanda Rios
    03/2012: pages 107-144; , ISBN: 978-953-51-0213-7
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    ABSTRACT: Complete (1) H and (13) C NMR chemical shift assignments for 3,4-seco-lup-20(29)-en-3-oic acid (1) have been established by means of two-dimensional COSY, HSQC, HMBC and NOESY spectroscopic experiments as well as by analysis of MS data. Compound 1 was isolated from Decatropis bicolor (Zucc.) Radlk. (Rutaceae) in addition to six coumarins and one alkaloid of known structure.
    Magnetic Resonance in Chemistry 03/2012; 50(4):329-31. · 1.53 Impact Factor

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