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Antifungal Phenylpropanoid Glycosides from Lippia rubella

Martins, Gabriel R., da Fonseca, Thamirys Silva, Martínez-Fructuoso, Lucero, Simas, Rosineide Costa, Silva, Fabio T., Salimena, Fatima Regina G., Alviano, Daniela S., Alviano, Celuta Sales, Leitão, Gilda Guimarães, Pereda-Miranda, Rogelio, Leitão, Suzana G.
Journal of natural products 2019 v.82 no.3 pp. 566-572
Cryptococcus neoformans, Lippia, active ingredients, amphotericin B, countercurrent chromatography, flavonoids, fractionation, glycosides, glycosylation, high performance liquid chromatography, lungs, medicinal properties, nuclear magnetic resonance spectroscopy, prototypes, spectral analysis, synergism, verbascoside
Lippia species share various pharmacological activities and are used in traditional cooking and medicine worldwide. Combined chromatographic techniques such as column chromatography, high-performance liquid chromatography, and countercurrent chromatography led to the purification of two new antifungal phenylpropanoid glycosides, lippiarubelloside A (1) and lippiarubelloside B (2), by bioactivity-directed fractionation of an ethanol-soluble extract from Lippia rubella, in addition to the known active related compounds forsythoside A (3), verbascoside (4), isoverbascoside (5), and poliumoside (6). The structures of compounds 1 and 2 were determined by comparison of their NMR spectroscopic data with the prototype active compound 4. Cryptococcus neoformans, which causes opportunistic lung infections, was sensitive to compounds 1–6 in the concentration range of 15–125 μg/mL. A synergistic effect (FICᵢₙdₑₓ = 0.5) between 3 and amphotericin B was demonstrated. The glycosylated flavonoids pectolinarin (7), linarin (8), and siparunoside (9) were also isolated.