New antioxidant C-glucosylxanthones from the stems of Arrabidaea samydoides.
Three new C-glucosylxanthones, 2-(2'-O-trans-caffeoyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (1), 2-(2'-O-trans-cinnamoyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (2), and 2-(2'-O-trans-coumaroyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (3), were isolated from the stems of Arrabidaea samydoides, in addition to three known C-glucosylxanthones, mangiferin (4), 2-(2'-O-benzoyl)-C-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (5), and muraxanthone (6). Their chemical structures were assigned on the basis of MS and 1D and 2D NMR experiments. Xanthones 1-6 showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity evidenced by redox properties measured on ElCD-HPLC.
NuBBE- Núcleo de Biossíntese, Bioensaios e Ecofisiologia de Produtos Naturais, Instituto de Química, Universidade Estadual Paulista, UNESP, CP 355, 14801-970, Araraquara, SP, Brazil.
Patrícia Mendonça
PM
Pauletti
Ian
I
Castro-Gamboa
Dulce Helena
DH
Siqueira Silva
Maria Claudia Marx
MC
Young
Daniela Maria
DM
Tomazela
Marcos Nogueira
MN
Eberlin
Vanderlan
V
da Silva Bolzani
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D044004:Xanthones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
C481245:2-(2'-O-trans-caffeoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone; C481246:2-(2'-O-trans-cinnamoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone; C481248:2-(2'-O-trans-coumaroyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone; D000975:Antioxidants; D002109:Caffeic Acids; D002934:Cinnamates; D003374:Coumarins; D005960:Glucosides; D044004:Xanthones