New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)
| Autor: | Maria de Fátima Agra, Carolina Campolina Rebello Horta, Alexander I. Gray, John O. Igoli, Marie Boyd, Weam Siheri, Yanna Carolina Ferreira Teles, Maria de Fátima Vanderlei de Souza |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Antioxidant
sulphated flavonoids Cell Survival medicine.medical_treatment Pharmaceutical Science Article Cell Line RS Analytical Chemistry lcsh:QD241-441 Wissadula periplocifolia isoscutellarein derivatives Inhibitory Concentration 50 chemistry.chemical_compound Column chromatography lcsh:Organic chemistry Drug Discovery medicine Humans Physical and Theoretical Chemistry Malvaceae Nuclear Magnetic Resonance Biomolecular Flavonoids Molecular Structure Acacetin Traditional medicine Plant Extracts Sulfates Organic Chemistry Isoscutellarein chemistry Phytochemical Chemistry (miscellaneous) Apigenin Hypolaetin Molecular Medicine Astragalin |
| Zdroj: | Molecules; Volume 20; Issue 11; Pages: 20161-20172 Molecules, Vol 20, Iss 11, Pp 20161-20172 (2015) Molecules Volume 20 Issue 11 Pages 20161-20172 |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules201119685 |
| Popis: | Wissadula periplocifolia (L.) C. Presl (Malvaceae) is commonly used in Brazil to treat bee stings and as an antiseptic. The antioxidant properties of its extracts have been previously demonstrated, thus justifying a phytochemical investigation for its bioactive phenolic constituents. This has yielded five new sulphated flavonoids: 8-O-sulphate isoscutellarein (yannin) (1a) 4′-O-methyl-7-O-sulphate isoscutellarein (beltraonin) (1b) 7-O-sulphate acacetin (wissadulin) (2a) 4′-O-methyl-8-O-sulphate isoscutellarein (caicoine) (2b) and 3′-O-methyl-8-O-sulphate hypolaetin (pedroin) (3b) along with the known flavonoids 7,4′-di-O-methyl-8-O-sulphate isoscutellarein (4), acacetin, apigenin, isoscutellarein, 4´-O-methyl isoscutellarein, 7,4′-di-O-methylisoscutellarein, astragalin and tiliroside. The compounds were isolated by column chromatography and identified by NMR (1H, 13C, HMQC, HMBC and COSY) and LC-HRMS. A cell based assay was carried out to evaluate the preliminary cytotoxic properties of the flavonoids against UVW glioma and PC-3M prostate cancer cells as well as non-tumour cell lines. The obtained results showed that acacetin, tiliroside, a mixture of acacetin + apigenin and the sulphated flavonoids 2a + 2b exhibited inhibitory activity against at least one of the cell lines tested. Among the tested flavonoids acacetin and tiliroside showed lower IC50 values, presenting promising antitumor effects. |
| Databáze: | OpenAIRE |
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