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 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.
Highlights
It is estimated that one third of the world’s population is infected with Mycobacterium tuberculosis.In 2010, there were 8.8 million new cases of tuberculosis (TB), 1.1 million deaths from TB amongHIV-negative people and an additional 0.35 million deaths from HIV-associated TB
It is important to mention that furanocoumarins have been found in fennel [14,16,17], and bergaptol could have antimycobacterial activity since it has been reported that some compounds of this type had activity against M. tuberculosis [18]
With respect to the variation of chemical composition of the other oxygenated compounds found in the active fraction, it can be explained by genotypic and environmental differences between the studied species
Summary
It is estimated that one third of the world’s population is infected with Mycobacterium tuberculosis. M. tuberculosis, and continuous efforts are under way in the search for novel bioactive compounds to develop new anti-tuberculosis drugs. To this end, bioactive compounds of natural origin, from plants, are gaining significance. Fennel was introduced in Mexico, where it is cultivated in home gardens and very often found free along roadsides and streams in the canyons of the Sierra Madre. It is used as a tea for stomach aches for its antispasmodic and carminative effects.
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