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Planta Med 2009; 75(8): 814-822
DOI: 10.1055/s-0029-1185440
Pharmacology
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Effect of Seven Tricyclic Diterpenoids from Needles of Taxus media var. Hicksii on Stimulus-Induced Superoxide Generation, Tyrosyl or Serine/Threonine Phosphorylation and Translocation of Cytosolic Compounds to the Cell Membrane in Human Neutrophils

Jia Tong1 , 2 , Jincai Lu2 , Na Zhang2 , Haidong Chi1 , Koichi Yamashita1 , Masanobu Manabe1 , Hiroyuki Kodama1
  • 1Department of Anesthesiology and Critical Care Medicine, Kochi Medical School, Nankoku Shi, Kochi, Japan
  • 2Department of Phytochemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China
Further Information

Publication History

received Nov. 6, 2008 revised January 19, 2009

accepted January 23, 2009

Publication Date:
13 March 2009 (online)

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Abstract

Taxol has been widely used as an anticancer drug for ovarian, breast, lung and prostate cancer. Some kinds of Taxus plants are widely distributed in the Northeast Asia region. We have isolated seven tricyclic diterpenoids, taxinine, taxagifine, 5-O-cinnamoyltaxacin I triacetate, 5-decinnamoyltaxinine J, 5-cinnamoyl-9-acetyltaxicin I, taxacin and taxol from the needles of Taxus media var. Hicksii, and investigated their effects on stimulus-induced superoxide generation and translocation of cytosolic compounds to the cell membrane in human neutrophils. Six tricyclic diterpenoids used in this experiment suppressed the superoxide generation induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) and arachidonic acid (AA) in a concentration-dependent manner. Taxinine significantly suppressed the superoxide generation induced by phorbol 12-myristate 13-acetate (PMA). The compounds also suppressed fMLP- and AA-induced tyrosyl or PMA-induced serine/threonine phosphorylation, and translocation of cytosolic compounds, p47phox, p67phox and Rac to the cell membrane in parallel with the suppression of the stimulus-induced superoxide generation.

Key words

Taxus media var. Hicksii - Taxaceae - superoxide - human neutrophils - phosphorylation - cytosolic compounds

References

  • 1 Blagosklonny M V, Fojo T. Molecular effects of paclitaxel: myths and reality (a critical review).  Int J Cancer. 1999;  83 151-156
    PubMedSearch in Google Scholar
  • 2 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 1155-1163
    CrossrefPubMedSearch in Google Scholar
  • 3 Takahashi R, Edashige K, Sato E F, Inoue M, Matsumo T, Utsumi K. Luminol chemiluminescence and active oxygen generation by activated neutrophils.  Arch Biochem Biophys. 1991;  285 325-330
    CrossrefPubMedSearch in Google Scholar
  • 4 Chanock S J, el Benna J, Smith R M, Bahior B M. The respireatory burst oxidase.  J Biol Chem. 1994;  269 24519-24522
    PubMedSearch in Google Scholar
  • 5 Henderson L M, Chappel J B. NADPH oxidase of neutrophils.  Biochem Biophys Acta. 1996;  1273 87-107
    PubMedSearch in Google Scholar
  • 6 Leusen J H, Verhoeven A J, Roos D. Interactions between the components of the human NADPH oxidase: intrigues in the phox family.  J Lab Clin Med. 1996;  128 461-476
    CrossrefPubMedSearch in Google Scholar
  • 7 Wang Z, Song S, Lu H, Chen G, Xu S, Sagara Y, Kitaoka N, Masanobu M, Kodama H. Effect of three triterpenoid compounds isolated from root bark of Aralia elata on stimulus-induced superoxide generation and tyrosyl phosphorylation and translocation of p 47 (phox) and p 67 (phox) to cell membrane in human neutrophil.  Clin Chim Acta. 2003;  336 65-72
    CrossrefPubMedSearch in Google Scholar
  • 8 Zhang M, Liu G, Tang S, Song S J, Yamashita K, Manabe M, Kodama H. Effect of five triterpenoid compounds from the buds of Aralia elata on stimulus-induced superoxide generation, tyrosyl phosphorylation and translocation of cytosolic compounds to the cell membrane in human neutrophils.  Planta Med. 2006;  72 1216-1222
    Thieme ConnectPubMedSearch in Google Scholar
  • 9 Sakai S, Katsumata M, Satoh Y, Nagasao M, Miyakoshi M, Ida Y, Shoji J. Oleanolic acid saponins from root bark of Aralia elata.  Phytochemistry. 1994;  35 1319-1324
    CrossrefPubMedSearch in Google Scholar
  • 10 Zhang J, Sagara Y, Fontana M, Duprè 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;  224 849-854
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 12 Zhang J, Sugahara K, Sagara Y, Fontana M, Duprè S, Kodama H. Effect of cystathionine ketimine on the stimulus coupled responses of neutrophils and their modulation by various protein kinase inhibitors.  Biochem Biophys Res Commun. 1996;  218 371-376
    CrossrefPubMedSearch in Google Scholar
  • 13 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
    CrossrefPubMedSearch in Google Scholar
  • 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 5911-5917
    PubMedSearch in Google Scholar
  • 15 Niwa A, Takeda O, Ishimaru M, Nakamoto Y, Yamasaki K, Kohda H, Nishio H, Segawa T, Fujimura K, Kuramoto A. Screening test for platelet aggregation inhibitor in natural products. The active principle of Anemarrhenae Rhizoma.  Yakugaku Zasshi. 1988;  108 555-561
    PubMedSearch in Google Scholar
  • 16 Chen G, Lu H, Wang C, Yamashita K, Manabe M, Meng Z, Xu S, Kodama H. 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;  326 169-175
    CrossrefPubMedSearch in Google Scholar

Prof. Hiroyuki Kodama

Department of Anesthesiology and Critical Care Medicine
Kochi Medical School

Nankoku-shi

Kochi 783–8505

Japan

Phone: + 81 8 88 65 59 37

Fax: + 81 8 88 65 59 37

Email: jm-hkodama@kochi-u.ac.jp