3-Desoxyanthocyanidins from Arrabidaea chica.
The new 3-desoxyanthocyanidins 6,7,3'-trihydroxy-5,4'-dimethoxy-flavylium and 6,7,3',4'-tetrahydroxy-5-methoxy-flavylium and the known 6,7-dihydroxy-5,4'-dimethoxy-flavylium (Carajurin) were isolated by bioguided fractionation from the leaves of Arrabidaea chica, with transcription factor NF-kappaB as target. The structure of Carajurone was revised to be 6,7,4'-trihydroxy-5-methoxy-flavylium. Additionally, the flavone acacetin was found. All structures were mainly established on the basis of MS- and NMR data (1H, 1H-1H COSY and partly 13C, GHMQCR and GHSQCR). Carajurin, which failed to give a positive result in the DPPH TLC assay completely inhibited NF-kappaB, but not NF-AT at a 500 microM concentration.
Zorn
B
B
Institute of Pharmaceutical Biology, Albert-Ludwigs-Universität Freiburg, Germany.
García-Piñeres
A J
AJ
Castro
V
V
Murillo
R
R
Mora
G
G
Merfort
I
I
D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D019169:Jurkat Cells / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry*; D016328:NF-kappa B / Q000378:metabolism; D014966:Xanthenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D016328:NF-kappa B; D014966:Xanthenes