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Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation

Anastassiya V. Gadetskaya, Amer H. Tarawneh, Galiya E. Zhusupova, Nadezhda G. Gemejiyeva, Charles L. Cantrell, Stephen J. Cutler, Samir A. Ross
Fitoterapia 2015 v.104 pp. 80-85
Candida glabrata, Limonium, Plasmodium falciparum, Trypanosoma brucei, acids, antibacterial properties, antifungal properties, antileishmanials, antimalarials, medicinal plants, myricetin, nuclear magnetic resonance spectroscopy, phenolic compounds, phloridzin, secondary metabolites, tyramine
Three new compounds, (2S-3S)-5-methyldihydromyricetin (1), (2S,3S)-5-methyldihydromyricetin-3'-O-sulfate (2) and ß-D-glucopyranoside, 3-methyl, but-3-en-1-yl 4-O-α-L-rhamnopyranosyl (3) have been isolated from the Limonium caspium, together with dihydromyricetin (4), dihydromyricetin-3'-O-sulfate (5), myricetin-3'-O-sulfate (6), 5-methylmyricetin (7), myricetin (8), myricetin-3-O-ß-glucoside (9), as well as phloridzin (10), and tyramine (11). Compounds 5 and 6 are isolated for the first time as acids. This is the first report of all these compounds from this plant. Their structures were established by extensive NMR studies ((1)H NMR, (13)C NMR, DEPT, (1)H–(1)H COSY, HSQC, HMBC) as well as HRESIMS. All isolated compounds were evaluated for their antibacterial, antifungal, antimalarial and antileishmanial activities. Compounds 7, 8 and 9 exhibited good antifungal activity against C. glabrata with IC(50) values of 6.79, 15.37 and 8.53 µg/ml, respectively. Compound 8 displayed significant antimalarial activity against resistant and sensitive strains of Plasmodium falciparum with IC(50) values of 1.82 and 1.51 µg/ml, respectively. Compounds 1, 4, 6, 8 and 9 showed excellent activity against Trypanosoma brucei with IC(50) values of 6.93, 9.65, 8.52, 7.67 and 6.31 µg/ml, respectively. To date, this is the first report on the phytochemical and biological activity of secondary metabolites from L. caspium.