Antifungal Phenylpropanoid Glycosides from Lippia rubella

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 antifung...

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Published inJournal of natural products (Washington, D.C.) Vol. 82; no. 3; pp. 566 - 572
Main Authors 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
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 22.03.2019
Amer Chemical Soc
Subjects
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
NMR
CHEMICAL-CONSTITUENTS
FORSYTHIA-SUSPENSA
ANTIOXIDANT
PURIFICATION
AMPHOTERICIN-B
INHIBITOR
EXTRACTS
COUPLING-CONSTANTS
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Abstract 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.
AbstractList 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.
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 (FIC = 0.5) between 3 and amphotericin B was demonstrated. The glycosylated flavonoids pectolinarin (7), linarin (8), and siparunoside (9) were also isolated.
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 compounds to compounds 1-6 in the concentration range of 15-125 mu g/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.
Author Martins, Gabriel R
Silva, Fabio T
Salimena, Fatima Regina G
Pereda-Miranda, Rogelio
da Fonseca, Thamirys Silva
Alviano, Daniela S
Simas, Rosineide Costa
Leitão, Gilda Guimarães
Leitão, Suzana G
Martínez-Fructuoso, Lucero
Alviano, Celuta Sales
AuthorAffiliation Faculdade de Farmácia, Centro de Ciências da Saúde (CCS)
ICB, Depto de Botânica
Instituto de Pesquisas de Produtos Naturais
Departamento de Farmacia, Facultad de Química
Universidade Federal de Juiz de Fora
Instituto de Microbiologia Paulo de Góes
Universidad Nacional Autónoma de México
AuthorAffiliation_xml – name: Universidad Nacional Autónoma de México
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Keywords NMR
CHEMICAL-CONSTITUENTS
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ANTIOXIDANT
PURIFICATION
AMPHOTERICIN-B
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Snippet Lippia species share various pharmacological activities and are used in traditional cooking and medicine worldwide. Combined chromatographic techniques such as...
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SubjectTerms Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
Title Antifungal Phenylpropanoid Glycosides from Lippia rubella
URI http://dx.doi.org/10.1021/acs.jnatprod.8b00975
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