Fabiola Escalante-Erosa

Antiprotozoal activity of betulinic acid derivatives.

Betulinic acid (1), isolated from the crude extract of the leaves of Pentalinon andrieuxii (Apocynaceae), together with betulinic acid acetate (2), betulonic acid (3), betulinic acid methyl ester (4), and betulin (5) were evaluated for their antiprotozoal activity. The results showed that modifying the C-3 position increases leishmanicidal activity while modification of the C-3 and C-28 positions decreases trypanocidal activity.

Trinorsesquiterpenoids from the Root Extract of Pentalinon andrieuxii

Two unusual trinorsesquiterpenoids, urechitols A (1) and B (2), were isolated from the root extract of Pentalinon andrieuxii, a plant used commonly in Yucatecan traditional medicine to treat leishmaniasis. The structures of 1 and 2 were identified by interpretation of their spectroscopic data and chemical correlation reactions. The relative stereochemistry of 1 was confirmed through an X-ray crystallographic study.

Antituberculosis activity of alkylated mulinane diterpenoids.

Natural azorellane and mulinane diterpenoids show antituberculosis activity, which is increased by methylation of their free carboxyl group. We have systematically investigated the effect of alkylation in this class of diterpenoids and found that the profile of bioactivity is relatively unaffected by the introduction of short alkyl groups, both linear and branched. In this investigation, three semisynthetic diterpenoids, 13 hydroxy-mulin-11-en-20-oic acid n-propyl ester (3) and the n-propyl (19) and n-butyl (20) esters of isomulinic acid, showed the strongest antituberculosis activity (MIC=6.25 microg/mL) against a drug-resistant strain of Mycobacterium tuberculosis.

Phytochemical Diversity of the Essential Oils of Mexican Oregano (Lippia graveolens Kunth) Populations along an Edapho‐Climatic Gradient

Mexican oregano (Lippia graveolens) is an important aromatic plant, mainly used as flavoring and usually harvested from non‐cultivated populations. Mexican oregano essential oil showed important variation in the essential‐oil yield and composition. The composition of the essential oils extracted by hydrodistillation from 14 wild populations of L. graveolens growing along an edaphoclimatic gradient was evaluated. Characterization of the oils by GC‐FID and GC/MS analyses allowed the identification of 70 components, which accounted for 89–99% of the total oil composition. Principal component and hierarchical cluster analyses divided the essential oils into three distinct groups with contrasting oil compositions, viz., two phenolic chemotypes, with either carvacrol (C) or thymol (T) as dominant compounds (contents >75% of the total oil composition), and a non‐phenolic chemotype (S) dominated by oxygenated sesquiterpenes. While Chemotype C was associated with semi‐arid climate and shallower and rockier soils, Chemotype T was found for plants growing under less arid conditions and in deeper soils. The plants showing Chemotype S were more abundant in subhumid climate. High‐oil‐yield individuals (>3%) were identified, which additionally presented high percentages of either carvacrol or thymol; these individuals are of interest, as they could be used as parental material for scientific and commercial breeding programs.

Synergistic Effect of Lupenone and Caryophyllene Oxide against Trypanosoma cruzi

The in vitro trypanocidal activity of a 1 : 4 mixture of lupenone and caryophyllene oxide confirmed a synergistic effect of the terpenoids against epimastigotes forms of T. cruzi (IC50 = 10.4 μg/mL, FIC = 0.46). In addition, testing of the terpenoid mixture for its capacity to reduce the number of amastigote nests in cardiac tissue and skeletal muscle of infected mice showed a reduction of more than 80% at a dose level of 20.8 mg·kg−1·day−1.

Bioactive metabolites from the Andean flora. Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids

Natural products are recognized as an important source of new and better pharmaceuticals for the treatment of diseases such as tuberculosis. The azorellane and mulinane diterpenoids represent an interesting group of bioactive metabolites produced by Andean plants belonging to the Azorella, Mulinum, Laretia and Bolax genus. Testing of natural and semisynthetic azorellanes and mulinanes against two Mycobacterium tuberculosis strains showed that while most changes in the structure of the natural metabolites result in the loss of antituberculosis activity, methylation of the C-20 carboxyl group improves the biological activity of the corresponding derivatives.

Antioxidant content in two CAM bromeliad species as a response to seasonal light changes in a tropical dry deciduous forest

Plants have evolved photoprotective mechanisms to limit photodamage; one of these mechanisms involves the biosynthesis of antioxidant metabolites to neutralize reactive oxygen species generated when plants are exposed to excess light. However, it is known that exposure of plants to conditions of extreme water stress and high light intensity results in their enhanced susceptibility to over-excitation of photosystem II and to photooxidative stress. In this investigation we used the 2,2-diphenyl-1-picrylhydrazyl reduction assay to conduct a broad survey of the effect of water availability and light exposure conditions on the antioxidant activity of the leaf extracts of two bromeliad species showing crassulacean acid metabolism. One of these was an epiphyte, Tillandsia brachycaulos, and the other a terrestrial species, Bromelia karatas. Both species were found growing wild in the tropical dry deciduous forest of Dzibilchaltún National Park, México. The microenvironment of T. brachycaulos and B. karatas experiences significant diurnal and seasonal light variations as well as changes in temperature and water availability. The results obtained showed that, for both bromeliads, increases in antioxidant activity occurred during the dry season, as a consequence of water stress and higher light conditions. Additionally, in T. brachycaulos there was a clear correlation between high light intensity conditions and the content of anthocyanins which accumulated below the leaf epidermis. This result suggests that the role of these pigments is as photoprotective screens in the leaves. The red coloration below the leaf epidermis of B. karatas was not due to anthocyanins but to other unidentified pigments.

Antihypertensive and vasorelaxant effects of dihydrospinochalcone-A isolated from Lonchocarpus xuul Lundell by NO production: Computational and ex vivo approaches

Current work was conducted to evaluate the vasorelaxant effect of dihydrospinochalcone-A (1) and isocordoin (2), compounds type chalcone isolated from Lonchocarpus xuul, an endemic tree of the Yucatan Peninsula, Mexico. Compounds 1 and 2 were found to induce significant relaxant effect in a concentration-dependent manner on aortic rat rings pre-contracted with noradrenaline (NA, 0.1 μM). Compound 1 was the most active and its effect was endothelium-dependent (Emax=79.67% and EC50=21.46 μM with endothelium and Emax=23.58% and EC50=91.8 μM without endothelium, respectively). The functional mechanism of action for 1 was elucidated. Pre-incubation with L-NAME (unspecific nitric oxide synthase inhibitor), indomethacin (unspecific COX inhibitor), ODQ (soluble guanylyl cyclase inhibitor), atropine (cholinergic receptor antagonist), TEA (unspecific potassium channel blocker) reduced relaxations induced by 1. Oral administration of 50 mg/kg of compound 1 exhibited significant decrease in diastolic and systolic blood pressure in SHR rats. The heart rate was not modified. Compound 1 was docked with a crystal structure of eNOS. Dihydrospinochalcone-A showed calculated affinity with eNOS in the C1 binding pockets, near the catalytic site; Trp449, Trp447 and His373 through aromatic and π-π interactions, also His463 and Arg367 are the residues that make hydrogen bonds with the carbonyl and hydroxyl groups. In conclusion, dihydrospinochalcone-A induces a significant antihypertensive effect due to its direct vasorelaxant action on rat aorta rings, through NO/sCG/PKG pathway and potassium channel opening.

Flourensia cernua: Hexane Extracts a Very Active Mycobactericidal Fraction from an Inactive Leaf Decoction against Pansensitive and Panresistant Mycobacterium tuberculosis

The efficacy of decoction in extracting mycobactericidal compounds from Flourensia cernua (Hojasé) leaves and fractionation with solvents having ascending polarity was compared with that of (i) ethanol extraction by still maceration, extraction with a Soxhlet device, shake-assisted maceration, or ultrasound-assisted maceration, followed by fractionation with n-hexane, ethyl acetate, and n-butanol; (ii) sequential extraction with n-hexane, ethyl acetate, and n-butanol, by still maceration, using a Soxhlet device, shake-assisted maceration, or ultrasound-assisted maceration. The in vitro mycobactericidal activity of each preparation was measured against drug-sensitive (SMtb) and drug-resistant (RMtb) Mycobacterium tuberculosis strains. The results of which were expressed as absolute mycobactericidal activity (AMA). These data were normalized to the ΣAMA of the decoction fraction set. Although decoction was inactive, the anti-RMtb normalized ΣAMA (NAMA) of its fractions was comparable with the anti-RMtb NAMA of the still maceration extracts and significantly higher than the anti-SMtb and anti-RMtb NAMAs of every other ethanol extract and serial extract and fraction. Hexane extracted, from decoction, material having 55.17% and 92.62% of antituberculosis activity against SMtb and RMtb, respectively. Although the mycobactericidal activity of decoction is undetectable; its efficacy in extracting F. cernua active metabolites against M. tuberculosis is substantially greater than almost all pharmacognostic methods.

Phytoanticipins from banana (Musa acuminata cv. Grande Naine) plants, with antifungal activity against Mycosphaerella fijiensis, the causal agent of black Sigatoka

The previously detected antifungal activity against Mycosphaerella fijiensis of aqueous infusions of healthy banana (Musa acuminata cv. Grande Naine) leaves, suggested the production of phytoprotectants by the plant. The bioassay-guided VLC-purification of the lyophilized infusion of the leaves of 4-month old healthy banana (M. acuminata cv. Grande Naine) plants, resulted in the purification of a phytoanticipin with strong antifungal activity against M. fijiensis Morelet, the causal agent of black Sigatoka, the most destructive and devastating disease of bananas and plantains in the world. The LC-MS analysis of the purified phytoanticipin suggests a steroidal saponin structure with four sugar units attached to the C-3 position of a diosgenin-like aglycone. This represents the first report of phytoanticipins occurring in M. acuminata.