Chemical composition and antimicrobial activity of Myrcianthes fragrans essential oil, a natural aromatizer of the traditional Ecuadorian beverage colada morada

Ethnobotanical and ethnomedicinal relevance: The importance given in Ecuador to the rescue of traditional knowledge and nutritional value of ancestral foods and drinks, has stimulated our investigation of the chemical composition and some biological activities of M. fragrans (‘arrayán’) essential oil, a natural aromatic additive used in the preparation of the traditional fruit-juice ‘colada morada’ which is typically drunk in the Day of the Dead or All Soul´s Day. Material and methods: Different essential oils of Myrcianthes fragrans (Sw.) McVaught were obtained by hydrodistillation of the aerial parts of the plant collected in Cerro Villonaco (Loja-Ecuador) at three different phenological growth stages, i.e., during foliation (Fo), flowering (Fl) and fruiting (Fr) stages. The chemical compositions of the essential oils were determined by GC/MS and GC/FID techniques. The antimicrobial activities were determined by the broth microdilution method and reported as minimal inhibitory concentration (MIC, ug/mL). Aims of the study: i) to investigate the traditional uses of arrayán (M. fragrans) in the South region of Ecuador; ii) to identify the main components of the essential oils isolated at different phenological stages; iiì) to test the antimicrobial activity of the essential oils against bacteria and yeasts causing human ailments and a yeast causing food spoilage. Results: 37, 46 and 38 compounds, representing 96.5%, 96.2%, and 95.6% of the three essential oils (Fo, Fl and Fr), respectively, have been identified. Oxygenated monoterpenes (OM) were the major components with percentages of 63.1 (Fo), 49.4 (Fl), and 61.9% (Fr), respectively. The main constituents of the essential oils were the monoterpene aldehydes geranial (1) and neral (2), the content of which varied, depending on the phenological development stage of the plant, spanning from 31.1% and 23.6% (Fo), to 23.6% and 17.8% (Fl), and 29.7% and 24.3% (Fr), respectively. In vitro antimicrobial tests showed that the essential oils from M. fragrans exhibited good activity against the Gram-negative bacteria, K. pneumoniae, and against the yeasts, C. albicans and S. cerevisiae. Conclusions: The oil is characterized by a high concentration of the monoterpene aldehydes geranial and neral (citral), that make the aroma of colada morada prepared in southern Ecuador quite different from the beverage made in other regions of the country, where other types of myrtles (Myrtaceae spp.) are used. Moreover, the oil may become a new rich source of the important industrial chemical citral. The pleasant aromatic properties and the good in vitro antimicrobial activity of arrayán oil suggest a plausible scientific explanation for the traditional uses of the plant not only as a natural aromatizer of a traditional beverage but also as a natural anti-infective and anti-yeast agent

TiF4-mediated biomimetic alkylation\u2013cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5- dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state

4-Alkyl- and 4-phenylcoumarins from Mesua ferrea as promising multidrug resistant antibacterials

Supercritical CO2 selectively extracted a series of 4-alkyl and 4-phenyl 5,7-dihydroxycoumarins from Mesua ferrea blossoms. Chemical modifications of the isolated compounds allowed us to confirm the structures elucidated by spectroscopic means and to prepare new derivatives amenable to SAR studies and potential pharmaceutical development. Biological investigations towards the screening on a number of bacteria strains and Plasmodium falciparum, identified compounds 1-9 as weak antiprotozoal agents and potent antibacterials on resistant Gram-positive strains