ISOLATION AND STRUCTURAL ELUCIDATION OF SPECIAL METABOLITES FROM THE LEAVES of Ouratea polygyna Engl. AND EVALUATION OF BIOLOGICAL ACTIVITIES
Ouratea polygyna Engl. Biflavonoids. Amentoflavone. Isoflavones.SARS-COV-2.
This work describes the phytochemical study of leaves of Ouratea polygyna Engl., that belong to Ochnaceae family. The plant material was collected at the Vale do Rio Doce Natural Reserve (RNV), in Linhares-ES and registered in the RNV herbarium. The crude extract of the leaves was prepared by maceration at room temperature with P.A methanol and concentrated in a rotary evaporator. The crude extract was partitioned with different organic solvents: hexane, dichloromethane, ethyl acetate and methanol, generating their respective partitions. From the hexane partition, were isolated the substances friedelin (1) and β-sitosterol (2). From the dichloromethane partition, were isolated the substances 7,7’’,4’’’-tri-O-methyl-lanaraflavone (3) and 3-β-O-β-Dglucopyranosyl sitosterol (4). From the ethyl acetate partition, amentoflavone (5), 5,4'- dihydroxy-6,7,3',6'-tetramethoxyisoflavone (6), lanceoloside A (7), a mixture of (7+8), being (8) the glycosylated derivative of benzoic acid and 3'-O-β-D-glucopyranosyl-5- hydroxy-6,7,4',5'-tetramethoxyisoflavone (9). All substances were elucidated through analysis of one-dimensional and two-dimensional 1H and 13C Nuclear Magnetic Resonance experiments and comparison with literature data. The substances 7,7’’,4’’’- tri-O-methyl-lanaraflavone (3), 5,4’-dihydroxy-6,7,3’,6’-tetramethoxy-isoflavone (6) and 3’-O-β-D-glucopyranosyl-5-hydroxy-6,7,4’,5’-tetramethoxyisoflavone (9) have not been found in the literature to date. Amentoflavone was tested in Huh-7 cell line for hepatocarcinoma and larvicidal activity against Aedes Aegypti and the glycosylated substances were investigated in silico for action on the 3CLPRO protein of SARS-COV- 2