Michael adducts of palmitoylascorbic acid: effects on the oxidative burst of neutrophils and the production of tumor necrosis factor-alpha in monocytes.
The effects of Michael adducts of 6-O-palmitoyl-L-ascorbic acid (compounds 1-4) on the phosphorylation-dependent response of stimulated monocytes and neutrophils was investigated. The pyranosyl derivative 3 increased the production of tumor necrosis factor-alpha in human monocytes stimulated with lipopolysaccharide (LPS). Compound 3 also enhanced the release of tumor necrosis factor-alpha from nonstimulated monocytes. Michael adducts 1-4 inhibited the formation of reactive oxygen species in fMLP-stimulated human neutrophils as measured by luminol chemiluminescence. Treatment with 6-O-palmitoyl-L-ascorbic acid (compound 5) also led to a decreased luminescence response of neutrophils. Results are discussed with respect to the inhibitory activity of Michael adducts of ascorbic acids towards protein phosphatases PP1/PP2A.
Gütschow
Michael
M
Pharmaceutical Institute, Poppelsdorf, University of Bonn, Germany.
Hauschildt
Sunna
S
Benard
Stefan
S
Reichl
Sabine
S
Witt
Uta G
UG
Eger
Kurt
K
Arnhold
Jürgen
J
D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D006801:Humans; D009000:Monocytes / Q000187:drug effects* / Q000378:metabolism; D009504:Neutrophils / Q000187:drug effects* / Q000378:metabolism; D016897:Respiratory Burst / Q000187:drug effects* / Q000502:physiology; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis*
D014409:Tumor Necrosis Factor-alpha; D001205:Ascorbic Acid; C031226:6-O-palmitoylascorbic acid