Antioxidant phenolic glycosides from Moricandia arvensis.
The new phenolic glycosides quercetin 3,4'-di-O-beta-d-glucopyranoside-7-O-alpha-l-rhamnopyranoside (moricandin) (1), beta-d-glucopyranosyl 4-O-beta-d-glucopyranosylcaffeate (2), methyl 3-O-beta-d-glucopyranosyl-5-hydroxycinnamate (3), and beta-d-glucopyranosyl 4-O-beta-d-glucopyranosylbenzoate (4), together with the previously known beta-d-glucopyranosyl 4-hydroxybenzoate (5), methyl 4-O-beta-d-glucopyranosylcaffeate (6), 1-O-caffeoyl-beta-d-glucopyranoside (7), and 2-phenylethyl-beta-d-glucopyranoside (8), were isolated from the flowers of Moricandia arvensis. Their structures were elucidated by extensive spectroscopic analysis and chemical methods. Compounds 1-8 were evaluated for antioxidant activity using DPPH, TEAC, and reducing power assays, where the caffeic acid derivative 7 and the quercetin triglycoside 2 proved to possess the most potent scavenging activity.
Braham
Hatem
H
Laboratoire de Chimie des Substances Naturelles et de Synthèse Organique, Faculté des Sciences de Monastir, 5000 Monastir, Tunisia.
Mighri
Zine
Z
Jannet
Hichem Ben
HB
Matthew
Susan
S
Abreu
Pedro M
PM
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds; D019607:Brassicaceae / Q000737:chemistry*; D002109:Caffeic Acids / Q000737:chemistry / Q000494:pharmacology; D035264:Flowers / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010851:Picrates / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D014416:Tunisia
D000975:Antioxidants; D001713:Biphenyl Compounds; D002109:Caffeic Acids; D016166:Free Radical Scavengers; D006027:Glycosides; D010851:Picrates; C501025:beta-D-glucopyranosyl 4-O-beta-D-glucopyranosylcaffeate; C501024:moricandin; C004931:1,1-diphenyl-2-picrylhydrazyl