Effect of Three Flavonoids Isolated from Japanese Polygonum Species on Superoxide Generation in Human Neutrophils

Abstract

Three flavonoids, quercetin 3-O-glucoside-2′′-gallate (QGG), quercetin 3-O-rhamnoside-2′′-gallate (QRG) and kaempferol 3-O-glucoside-2′′-gallate (KGG) were isolated from Japanese Polygonum species. The effect of these flavonoids on stimulus-induced superoxide generation in human neutrophils was assayed by measuring the reduction of cytochrome c. The tyrosyl or serine/threonine phosphorylation of neutrophil proteins and the translocation of p47^phox and p67^phox to the cell membrane were detected using specific monoclonal antibodies. The flavonoids used in this experiment significantly suppressed stimulus-induced superoxide generation in a concentration-dependent manner. FMLP-induced tyrosyl phosphorylation or PMA-induced serine/threonine phosphorylation and the translocation of the cytosolic proteins p47^phox and p67^phox to the cell membrane were suppressed in parallel to the suppression of the stimulus-induced superoxide generation.

Key words

Polygonum - flavonoids - superoxide - human neutrophils - cytosolic compounds

References

• 1 Isobe T, Fukushige T, Noda Y. A new flavonoid glycoside from Polygonum nodosum . Chem Lett 1979: 27-30
• 2 Isobe T, Ito N, Noda Y. Minor flavonoids of Polygonum nodosum .  Phytochemistry. 1980;  19 1877
• 3 Isobe T, Kanazawa K, Fujimura M, Noda Y. Flavonoids of Polygonum sieboldi and P. filiforme .  Bull Chem Soc Jpn. 1981;  54 3239
• 4 Zhang J, Sugahara K, Yasuda K, Kodama H, Sagara Y, Kodama H. The effects of serum iminodipeptides and prednisolone on superoxide generation and tyrosyl phosphorylation of proteins in neutrophils from a patient with prolidase deficiency.  Free Radic Biol Med. 1998;  24 689-98
• 5 Goldstein I M, Roos D, Kaplan H B, Weissmann G. Complement and immunoglobulins stimulate superoxide production by human leukocytes independently of phagocytosis.  J Clin Invest. 1975;  56 1155-63
• 6 Takahashi R, Edashige K, Sato E F, Inoue M, Matsuno T, Utsumi K. Luminol chemiluminescence and active oxygen generation by activated neutrophils.  Arch Biochem Biophys. 1991;  285 325-30
• 7 Zhang J, Sagara Y, Fontana M, Dupre S, Cavallini D, Kodama H. Effect of cystathionine and cystathionine metabolites on the phosphorylation of tyrosine residues in human neutrophils.  Biochem Biophys Res Commun. 1996;  224 849-54
• 8 Chanock S J, el Benna J, Smith R M, Babior B M. The respiratory burst oxidase.  J Biol Chem. 1994;  269 24 519-22
• 9 Henderson L M, Chappel J B. NADPH oxidase of neutrophils.  Biochim Biophys Acta. 1996;  1273 87-107
• 10 Lu H W, Sugahara K, Sagara Y, Masuoka N, Asaka Y, Manabe M. et al . Effect of three flavonoids, 5,7,3′,4′-tetrahydroxy-3-methoxyflavone, luteolin, and quercetin, on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophil.  Arch Biochem Biophys. 2001;  393 73-7
• 11 Weiss S J, Klein R, Slivka A, Wei M. Chlorination of taurine by human neutrophils. Evidence for hypochlorous acid generation.  J Clin Invest. 1982;  70 598-607
• 12 Yamamoto M, Saeki K, Utsumi K. Isolation of human salivary polymorphonuclear leukocytes and their stimulation-coupled responses.  Arch Biochem Biophys. 1991;  289 76-82
• 13 Laemmli U K. Cleavage of structural proteins during the assembly of the head of bacteriophage.  Nature. 1970;  227 680-5
• 14 Nauseef W M, Volpp B D, McCormick S, Leidal K G, Clark R A. Assembly of the neutrophil respiratory burst oxidase. Protein kinase C promotes cytoskeletal and membrane association of cytosolic oxidase components.  J Biol Chem. 1991;  266 5911-7
• 15 Lu J, Sun Q, Sugahara K, Sagara Y, Kodama H. Effect of six compounds isolated from rhizome of Anemone raddeana on the superoxide generation in human neutrophil.  Biochem Biophys Res Commun. 2001;  280 918-22
• 16 Chen G, Lu H, Wang C, Yamashita K, Manabe M, Meng Z. et al . Effect of five flavonoid compounds isolated from leaves of Diospyros kaki on stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils.  Clin Chim Acta. 2002;  326 169-75