title: Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation.
abstract: Three new compounds, (2S,3S)-5-methyldihydromyricetin (1), (2S,3S)-5-methyldihydromyricetin-3'-O-sulfate (2) and β-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-β-glucoside (9), as well as phloridzin (10), and tyramine (11). Compounds 5 and 6 were 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 Candida glabrata with IC50 values of 6.79, 15.37 and 8.53μg/mL, respectively. Compound 8 displayed significant antimalarial activity against resistant and sensitive strains of Plasmodium falciparum with IC50 values of 1.82 and 1.51μg/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 6.31μg/mL, respectively. To date, this is the first report on the phytochemical and biological activity of secondary metabolites from L. caspium.
authors.affiliation: National Center for Natural Products Research, University of Mississippi, University, MS 38677, USA; School of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, Almaty, 050040, Kazakhstan.
authors.forename: Anastassiya V
authors.initials: AV
authors.lastname: Gadetskaya
authors.affiliation: Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA.
authors.forename: Amer H
authors.initials: AH
authors.lastname: Tarawneh
authors.affiliation: School of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, Almaty, 050040, Kazakhstan.
authors.forename: Galiya E
authors.initials: GE
authors.lastname: Zhusupova
authors.affiliation: Botanical Garden, the Institute of Botany and Phytointrodaction, Almaty, 480070, Kazakhstan.
authors.forename: Nadezhda G
authors.initials: NG
authors.lastname: Gemejiyeva
authors.affiliation: Natural Products Utilization Research Unit, USDA-ARS, University, MS 38677, USA.
authors.forename: Charles L
authors.initials: CL
authors.lastname: Cantrell
authors.affiliation: Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Cutler
authors.affiliation: National Center for Natural Products Research, University of Mississippi, University, MS 38677, USA; Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA. Electronic address: sross@olemiss.edu.
authors.forename: Samir A
authors.initials: SA
authors.lastname: Ross
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D041221:Candida glabrata / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D035261:Plant Components, Aerial / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D029606:Plumbaginaceae / Q000737:chemistry*; D064210:Secondary Metabolism; D014346:Trypanosoma brucei brucei / Q000187:drug effects
chemical_list: D000935:Antifungal Agents; D000962:Antimalarials; D010636:Phenols
keywords: Antifungal; Antileishmanial; Antimalarial; Dihydromyricetin; Limonium caspium; Myricetin; Sulfated flavonoids