María Yolanda Rios

Antidiabetic activity of some pentacyclic acid triterpenoids, role of PTP-1B: in vitro, in silico, and in vivo approaches.

The aim of the current study was to investigate the oral antidiabetic activity of four structurally-related triterpenic acids: ursolic (RE-01), oleanolic (RE-02), moronic (RE-03) and morolic (RE-04) acids. STZ-nicotinamide diabetic rats were treated with these triterpenes (50 mg/kg) and the antidiabetic effects in acute experiment were determined. All compounds showed significant antidiabetic activity in comparison with control group (p<0.05). The in vitro inhibitory activity of compounds against protein tyrosine phosphatase 1B (PTP-1B) was also evaluated. At 50 μM, the enzymatic activity was almost completely inhibited. All compounds were docked with a crystal structure of PTP-1B. Docking results suggested the potential binding of the triterpenic acids in a binding pocket next to the catalytic site. An extensive hydrogen bond network with the carboxyl group and Van der Waals interactions stabilize the protein-ligand complexes.

Antifungal activities of nine traditional Mexican medicinal plants

Eighteen plant extracts from nine traditional Mexican medicinal plants were tested for antifungal activity against two dermatophyte fungal species (Trichophyton mentagrophytes and Trichophyton rubrum), one non-dermatophyte (Aspergillus niger), and one yeast (Candida albicans). The strongest effect was manifested by the hexane extracts from Eupatorium aschenbornianum and Sedum oxypetalum, as well as the methanol extracts from Lysiloma acapulcensis and Annona cherimolia.

Baeyer–Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing urea–hydrogen peroxide in ethyl acetate

A green method for Baeyer–Villiger oxidation based on the chemo-enzymatic perhydrolysis of carboxylic acids and esters has been optimized using Novozyme-435, the immobilized form of Candida antarctica lipase B, and the complex urea–hydrogen peroxide (UHP) in ethyl acetate. This protocol previously employed for the chemo-enzymatic epoxidation of unfunctionalized olefins was shown to be effective for the Baeyer–Villiger oxidation of cyclohexanone and substituted cyclohexanones. The absence of water in the reaction media avoided any hydrolysis of the oxidized product. A minimum amount of enzyme was necessary to show the catalytic effect. The reaction yields of substituted e-caprolactones varied depending on the nature of the substituent.

Tyrianthinic Acids from Ipomoea tyrianthina and Their Antimycobacterial Activity, Cytotoxicity, and Effects on the Central Nervous System #

Four new partially acylated tetrasaccharides of 11-hydroxyhexadecanoic acid (1-4) were isolated from a methanolic extract of Ipomoea tyrianthina. The structures of these compounds were elucidated by spectroscopic and chemical methods. The resin glycoside composition of I. tyrianthina varied with the location of growth in Mexico. Compounds 1-4 showed antimycobacterial activity, were cytotoxic against the KB cell line, and, in a mouse model, exhibited potentiation of hypnosis induced by pentobarbital, protected against seizures induced by pentylenetetrazole, and released GABA and glutamic acid.

Antimycobacterial Activity of Constituents from Foeniculum vulgare var. Dulce Grown in Mexico

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 1H and 13C (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.

Antinociceptive effect of Heliopsis longipes extract and affinin in mice.

Heliopsis longipes is used as analgesic in Mexican traditional medicine. The present study assesses the possible antinociceptive effect of Heliopsis longipes and describes the pharmacological mechanism of action of the antinociceptive effect of affinin, identified as the one active principle in Heliopsis longipes acetone extract. Intraperitoneal administration of H. longipes extract and affinin produced a dose-dependent antinociceptive effect when assessed in mice submitted to acetic acid and capsaicin tests. Affinin-induced antinociception (30 mg/kg, I. P.) was blocked by naltrexone (1 mg/kg, S. C.), P-chlorophenylalanine (80 mg/kg, I. P.) and flumazenil (5 mg/kg, S. C.) suggesting that its pharmacological effect could be due to the activation of opiodergic, serotoninergic and GABAergic systems. In addition, the antinociceptive effect of affinin was attenuated by pretreatment with 1 H-[1,2,4]oxadiazolo[1,2- A]quinoxalin-1-one (1 mg/kg, S. C.) and glibenclamide (10 mg/kg, S. C.) suggesting that the nitric oxide-K (+) channels pathway could be involved in its mechanism of action. These results suggest that affinin itself or its derivatives may have potential antinociceptive effects.

Two new benzofuranes from Eupatorium aschenbornianum and their antimicrobial activity.

Through a bioassay-guided fractionation, from the aerial parts of the medicinal plant Eupatorium aschenbornianum were isolated two new benzofurane compounds, 5-acetyl-3beta-angeloyloxy-2beta-(1-hydroxyisopropyl)-2,3-dihydrobenzofurane ( 1) and 5-acetyl-3beta-angeloyloxy-2beta-(1-hydroxyisopropyl)-6-methoxy-2,3-dihydrobenzofurane ( 2) in addition to 4-hydroxy-3,5-diprenylacetophenone, espeletone ( 3), encecalinol ( 4), beta-sitosterol and stigmasterol. The antimicrobial evaluation of these natural products showed that 1 [MIC = 200 microg/mL against T. mentagrophytes and 100 microg/mL against T. rubrum], 2 [MIC = 50 microg/mL towards both] and 3 [MIC = 100 microg/mL against both] were active against dermatophytes, while 4 was active against all of microorganisms assayed [MIC = 12.5 microg/mL ( T. mentagrophytes), 12.5 microg/mL ( T. rubrum), 100 microg/mL ( C. albicans) and 200 microg/mL ( A. niger)].

Chemical reactivity of phthalides. Relay synthesis of diligustilide, Rel-(3 ' R)-3 ',8 '-dihydrodiligustilide and wallichilide.

Abstract Diels Alder reaction using Z-ligustilide (3) both as diene and dienophile afforded the natural product diligustilide (1). The relay synthesis of 5 from 1 (via situ-selective lactone ring opening, reduction with NaBH4/MeOH and lactonization with SOCl2/THF) was achieved and confirmed the revised structure of 5, a secondary constituent of Ligusticum wallichii. The natural substance wallichilide (8) was also obtained directly from 1.

Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media

Aqueous in situ one-pot N-Boc-deprotection-cyclization of Nα-Boc-dipeptidyl-tert-butyl and methyl esters under microwave irradiation afforded 2,5-diketopiperazines (DKPs) in excellent yields. This protocol is rapid, safe, environmentally friendly, and highly efficient, and showed that the tert-butoxy moiety is also an excellent leaving group for these cyclizations.

Vasorelaxant activity of some structurally related triterpenic acids from Phoradendron reichenbachianum (Viscaceae) mainly by NO production: Ex vivo and in silico studies ☆

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.