Download PDF
Planta Med 2004; 70(9): 877-880
DOI: 10.1055/s-2004-827241
Letter
© Georg Thieme Verlag KG Stuttgart · New York

A New seco-Abietane-Type Diterpene from the Stem Bark of Picea glehni

Reiko Tanaka1 , Shun-ichi Wada1 , Yoshitaka Kinouchi1 , Harukuni Tokuda2 , Shunyo Matsunaga1
  • 1Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, Osaka, Japan
  • 2Department of Biochemistry, Kyoto Prefectural University of Medicine, Kyoto, Japan
Further Information

Publication History

Received: January 14, 2004

Accepted: May 15, 2004

Publication Date:
23 September 2004 (online)

Also available at
    Permissions and Reprints

Abstract

A new seco-abietane-type diterpenoid, 13S-hydroxy-9-oxo-9,10-seco-abiet-8(14)-en-18,10α-olide (1) along with a known lignan compound, pinoresinol (2) was isolated from the stem bark of Picea glehni (Fr. Schm.) Masters. Spectroscopic methods and chemical conversions were used to establish the structure of 1. In order to assess their cancer chemopreventive potential, the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) was examined for compound 1, its synthetic analogue, 9,10-seco-8S,13S-epoxy-abiet-8(14)-en-18,10α-olide (1a) and 2. The inhibitory effect of 1a on EBV-EA induction was strong (0, 20.7, 67.1 and 89.2 % inhibition at 1000, 500, 100 and 10 mol ratio/TPA). The IC50 of 1a was 226 mol ratio/32 pmol/TPA.

References

  • 1 Kinouchi Y, Ohtsu H, Tokuda H, Nishino H, Matsunaga S, Tanaka R. Potential antitumor-promoting diterpenoids from the stem bark of Picea glehni .  Journal of Natural Products. 2000;  63 817-20
    CrossrefPubMedSearch in Google Scholar
  • 2 Tanaka R, Kinouchi Y, Tokuda H, Nishino H, Matsunaga S. Bioactive triterpenoids from the stem bark of Picea glehni .  Planta Medica. 2000;  66 630-4
    Thieme ConnectPubMedSearch in Google Scholar
  • 3 Tanaka R, Minami T, Tsujimoto K, Matsunaga S, Tokuda H, Nishino H, Terada Y, Yoshitake A. Cancer chemopreventive agents, serratane-type triterpenoids from Picea jezoensis .  Cancer Letters. 2001;  172 119-26
    CrossrefPubMedSearch in Google Scholar
  • 4 Ludwig C H, Nist B J, McCarthy J L. The high resolution nuclear magnetic resonance spectroscopy of protons in compounds related to lignan.  Journal of American Chemical Society. 1964;  86 1186-96
    PubMedSearch in Google Scholar
  • 5 Herz W, Mohanraj S. Structure proof by synthesis of unusual secodehydroabietanes from Tall oil.  Journal of Organic Chemistry. 1980;  45 5417-9
    CrossrefPubMedSearch in Google Scholar
  • 6 Fuji K, Zheng S Z, Node M, Hao X J. A chiral synthesis of a unique seco-dehydroabietane from Tall oil.  Chemical and Pharmaceutical Bulletin. 1991;  39 202-3
    PubMedSearch in Google Scholar
  • 7 Ito M, Kawanishi M, Harayama T, Takabayashi S. Combined effect of the extracts from Croton tiglium, Euphorbia lathyris or Euphorbia tirucalli and n-butyrate on Epstein-Barr virus expression in human lymphoblastoid P3HR-1 and Raji cells.  Cancer Letters. 1981;  12 175-80
    CrossrefPubMedSearch in Google Scholar
  • 8 Huang M -T, Smart R -C, Wong C -Q, Conney A -H. Inhibition effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol 13-acetate.  Cancer Research. 1988;  48 5941-6
    PubMedSearch in Google Scholar

Dr. Reiko Tanaka

Department of Medicinal Chemistry

Osaka University of Pharmaceutical Sciences

4-20-1 Nasahara

Takatsuki

Osaka 569-1094

Japan

Phone: +81-72-690-1084

Fax: +81-72-690-1084

Email: tanakar@gly.oups.ac.jp