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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #316331

Research Project: Chemistry of Natural Products for Nutraceutical Use, Pest Management and Crop Development

Location: Natural Products Utilization Research

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

Author
item Gadetskaya, Anastassiya - University Of Mississippi
item Tarawneh, Amer - University Of Mississippi
item Zhusupova, Galiya - Al-Farabi Kazakh National University
item Gemejiyeva, Nadezhda - Botanical Garden, Institute Of Botany And Phytointroduction
item Cantrell, Charles
item Cutler, Stephen - University Of Mississippi
item Ross, Samir - University Of Mississippi

Submitted to: Fitoterapia
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/22/2015
Publication Date: 5/27/2015
Publication URL: http://handle.nal.usda.gov/10113/62276
Citation: Gadetskaya, A.V., Tarawneh, A.H., Zhusupova, G.E., Gemejiyeva, N.G., Cantrell, C.L., Cutler, S.J., Ross, S.A. 2015. Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation. Fitoterapia. 104:80-85.

Interpretive Summary: Ethnopharmacology, the study of plants traditionally used for medical purposes with the aim of discovering their pharmacological properties, is a promising area for the discovery of novel medicinal compounds. As a part of our search for novel, plant-derived biological agents, Limonium caspium was studied. The present study was aimed to investigate the constituent of L. caspium aerial parts. The fractionation, isolation and structural elucidation yielded a total of eleven compounds. All isolated compounds were evaluated for their antimalarial, antileishmanial, antifungal and antimicrobial activities. Three new compounds, 5-methyldihydromyricetin, 5-methyldihydromyricetin-3'-O-sulfate and ß-D-glucopyranoside, 3-methyl, but-3-en-1-yl 4-O-a-L-rhamnopyranosyl have been isolated from the Limonium caspium, together with dihydromyricetin, dihydromyricetin-3'-O-sulfate, myricetin-3'-O-sulfate, 5-methylmyricetin, myricetin, myricetin-3-O-ß-glucoside, as well as phloridzin, and tyramine. Biological evaluation for the pure compounds is reported.

Technical Abstract: Three new compounds, 5-methyldihydromyricetin (1), 5-methyldihydromyricetin-3'-O-sulfate (2) and ß-D-glucopyranoside, 3-methyl, but-3-en-1-yl 4-O-a-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 (1H NMR, 13C NMR, DEPT, 1H–1H 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 IC50 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 IC50 values of 1.82 and 1.51 µg/ml, respectively. Compounds 1, 4, 6, 8 and 9 showed excellent activity against Trypanosoma brucei with IC50 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.