Gonzalo J. Mena-Rejón

Cassine, an antimicrobial alkaloid from Senna racemosa

The leaves of Senna racemosa yielded the piperidine alkaloid cassine and an inositol methyl ether. Antimicrobial screening of the compounds revealed antibacterial activity of cassine with minimum inhibitory concentrations of 2.5 mg/ml for Staphylococcus aureus and Bacillus subtilis and 5.0 mg/ml for Candida albicans.

In vitro cytotoxic activity of nine plants used in Mayan traditional medicine.

ETHNOPHARMACOLOGICAL RELEVANCE Plants have been used in folk medicine by Mayan ancient people from the Yucatan Peninsula, Mexico, to treat some diseases considered as cancer diseases such as chronic wounds or tumors. AIM OF THE STUDY We collected a selection of nine plants in order to investigate their cytotoxic activity against cancer cell lines. MATERIALS AND METHODS Methanolic extracts were tested for their cytotoxicity using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay on four cancer cell lines; nasopharynx carcinoma (KB), laryngeal carcinoma (Hep-2), cervix adenocarcinoma (HeLa), and cervix squamous carcinoma cells (SiHa) and one normal cell line; canine kidney (MDCK). RESULTS All species exhibited some degree of cytotoxic activity. The root bark extract of Hamelia patens exhibited the highest cytotoxic activity on HeLa cells with a CC50 of 13 microg/mL and selectivity index of 13.3, higher than docetaxel. Gossypium schottii and Dioon spinulosum showed similar good cytotoxic activity and selectivity index on HeLa and Hep-2 cells, respectively. CONCLUSIONS Hamelia patens, Dioon spinulosum and Gossypium schottii demonstrated promising cytotoxic activity and have been selected for future bio-guided fractionation and isolation of active cytotoxic compounds.

Screening of Antibacterial and Antifungal Activities of Six Marine Macroalgae from Coasts of Yucatán Peninsula

Abstract Ethyl acetate partition of methanol extracts of Avrainvillea nigricans. Decaisne (Udoteaceae), Codium decorticatum. (Woodward) Howe (Codiaceae), Halymenia floresia. (Clemente) C. Agardh (Grateloupiaceae), Laurencia obtusa. (Hudson) Lamouroux (Rhodomelaceae), Sargassum filipendula. C. Agardh (Sargassaceae), and Sargassum hystrix. J. Agardh, marine macroalgae from Yucatán peninsula coasts, were screened using the well-diffusion technique against three Gram-positive bacteria, four Gram-negative bacteria, two yeasts, and two molds. The extracts inhibited the growth of Staphyloccocus aureus. at 6.25–1.56 mg/mL and Bacillus subtilis. at 6.25–0.78 mg/mL. Trichophyton mentagrophytes. growth was inhibited by extracts of Laurencia obtusa., Sargassum filipendula., and Sargassum hystrix. at 6.25–3.13 mg/mL. The minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) were obtained by the microplate method.

Antimicrobial activity of Fabaceae species used in Yucatan traditional medicine.

The methanol and water extracts of six Fabaceae species, traditionally used in Mayan medicine for the treatment of diarrhoea and eye infections, were phytochemically screened and tested for in vitro antimicrobial activity. Four species showed activity against Gram positive bacteria, five exhibited some activity against Candida albicans, two exhibited activity against Aspergillus niger and only one, Mimosa pigra, inhibited growth of Pseudomonas aeruginosa. None of the extracts was active against Escherichia coli.

The Rotational Barrier in Ethane: A Molecular Orbital Study

The energy change on each Occupied Molecular Orbital as a function of rotation about the C-C bond in ethane was studied using the B3LYP, mPWB95 functional and MP2 methods with different basis sets. Also, the effect of the ZPE on rotational barrier was analyzed. We have found that σ and π energies contribution stabilize a staggered conformation. The σs molecular orbital stabilizes the staggered conformation while the stabilizes the eclipsed conformation and destabilize the staggered conformation. The πz and molecular orbitals stabilize both the eclipsed and staggered conformations, which are destabilized by the πv and molecular orbitals. The results show that the method of calculation has the effect of changing the behavior of the energy change in each Occupied Molecular Orbital energy as a function of the angle of rotation about the C–C bond in ethane. Finally, we found that if the molecular orbital energy contribution is deleted from the rotational energy, an inversion in conformational preference occurs.

Cytotoxic diterpenes from roots of Crossopetalum gaumeri, a Celastraceae species from Yucatan Peninsula

Four new diterpenes, crossogumerins A-D (1-4) along with six known ones (5-10) were isolated from the root bark of Crossopetalum gaumeri, an endemic medicinal plant from the Yucatan Peninsula. Their structures were elucidated on the basis of 1D and 2D NMR techniques, including HMQC, HMBC, and ROESY experiments. Compounds 1-5, 8-10 were evaluated for cytotoxicity against HeLa (carcinoma of the cervix) and Hep-2 (lung carcinoma) human tumor cells lines and against normal Vero cells (African green monkey kidney) in lag and log phase of growth. Podocarpane diterpenes, crossogumerin B (2) and nimbiol (10), exhibited the highest activity against HeLa cells (IC50 values of 3.1 and 8.1 μM, respectively), but also selectivity on Vero cells (SI 22.6 and 7.5, respectively). The preliminary SAR studies suggest that an epoxy moiety in ring B and a hydrogen bond-donor group strategically positioned in the diterpene core are important requirements for cytotoxicity and selectivity.

Isolation and antitrichomonal activity of the chemical constituents of the leaves of Maytenus phyllanthoides Benth. (Celastraceae)

Cyclolignan (+)-lyoniresinol (1), veratric acid (2), vanillic acid (3), lupeol, oleanolic acid, 3β-hydroxy-urs-11-en-28,13β-lactone (4), the mixture of α- and β-amyrin, trans-polyisoprene, and β-sitosterol were isolated from the leaves of Maytenus phyllanthoides. The structures of the isolated compounds were established based on spectroscopic data, mainly 1H and 13C nuclear magnetic resonance (NMR). Compound 1, its acetate analog 1a, and compounds 2, 3, and 4 were tested against Trichomonas vaginalis. (+)-Lyoniresinol showed activity corresponding to IC50 17.57 µM. This is the first report on the occurrence of 3β-hydroxy-urs-11-en-28,13β-lactone (4) in the Celastraceous family and lyoniresinol in the Maytenus genus, and on the antitrichomonal activity of lyoniresinol.

Diversifying Complexity by Domino Benzannulation of Polycyclic Natural Products

Herein we describe a salicylaldehyde-annulation reaction as a plug and play toolkit to diversify the complexity of naturally occurring ketones. The protocol entails the transformation of the polycyclic natural ketone into its propargyl vinyl ether derivative (two synthetic steps) and its microwave-assisted imidazole-catalyzed domino rearrangement to generate the salicylaldehyde ring. This annexed unit allows further synthetic transformations: e.g., the installation of a pharmacophore module to generate natural product-pharmacophore hybrids endowed with unknown biological (pharmaceutical) annotations.

Biogenesis of Triterpene Dimers from Orthoquinones Related to Quinonemethides: Theoretical Study on the Reaction Mechanism

The biogenetic origin of triterpene dimers from the Celastraceae family has been proposed as assisted hetero-Diels-Alder reaction (HDA). In this work, computational calculation of HDA between natural quinonemethides (tingenone and isopristimerol) and hypothetical orthoquinones has been performed at the M06-2X/6-31G(d) level of theory. We have located all the HDA transition states supporting the biogenetic route via HDA cycloadditions. We found that all reactions take place through a concerted inverse electron demand and asynchronous mechanism. The enzymatic assistance for dimer formation was analyzed in terms of the calculated transition state energy barrier.

Triterpenoids from Hippocratea excelsa. The Crystal Structure of 29-Hydroxytaraxerol

The root bark of Hippocratea excelsa afforded a new derivative of β -amyrin, which was identified as its ferulate, together with components new in this species. They were identified as the rare 29-hydroxytaraxerol, 29-hydroxyglutinol, 29-hydroxyfriedelin and the sterol 6β -hydroxystigmast-4- en-3-one. The known triterpene quinone methides pristimerin and tingenone characteristics of this genus, β -sitosterol, trans-polyisoprene, squalene, β -amyrin, and the alditol galacticol characteristic of the Celastraceae were also isolated. The structures were established on the basis of spectral analysis, including homo- and heteronuclear correlation NMR experiments (COSY, DEPT, HMQC and HMBC) and by comparison with data reported in the literature. The structure of 29-hydroxytaraxerol was confirmed by X-ray diffraction. The antimicrobial and antifungal activities of the compounds were studied, but no significant activity was found.