title: Unusual C,O-Fused Glycosylapigenins from Serjania marginata Leaves.
abstract: A phytochemical study of a Serjania marginata leaf extract with antiulcer activity afforded 15 compounds, including the new 3-O-α-l-arabinopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)[β-d-glucopyranosyl(1→4)]-α-l-arabinopyranosyloleanolic acid (1) and 7,5″-anhydroapigenin 8-C-α-(2,6-dideoxy-5-hydroxy-ribo-hexopyranosyl)-4'-O-β-d-glucopyranoside (4). The structures of the new compounds were determined by spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Compound 4 is a C-hexopyranosylapigenin with an unusual cyclic ether linkage between C-5″ and C-7 of apigenin. The isolated proanthocyanidins have high antioxidant activities, and these compounds are probably responsible for the gastroprotective effect of the extract.
authors.affiliation: Grupo de Alelopatía, Departamento de Química Orgánica, Instituto de Biomoléculas (INBIO), Facultad de Ciencias, Universidad de Cádiz , C/República Saharaui, 7, 11510 Puerto Real (Cádiz), Spain.
authors.forename: Silvia C
authors.initials: SC
authors.lastname: Heredia-Vieira
authors.forename: Ana M
authors.initials: AM
authors.lastname: Simonet
authors.forename: Wagner
authors.initials: W
authors.lastname: Vilegas
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Macías
mesh_terms: D000897:Anti-Ulcer Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D047310:Apigenin / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001938:Brazil; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D029631:Sapindaceae / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry
chemical_list: D000897:Anti-Ulcer Agents; D006027:Glycosides; D012503:Saponins; D014315:Triterpenes; D009828:Oleanolic Acid; D047310:Apigenin; C032731:vitexin