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

Reiko Tanaka; Shun-ichi Wada; Yoshitaka Kinouchi; Harukuni Tokuda; Shunyo Matsunaga

doi:10.1055/s-2004-827241

Planta Medica, Inhaltsverzeichnis

Planta Med 2004; 70(9): 877-880
DOI: 10.1055/s-2004-827241

Letter

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

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.

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References

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Dr. Reiko Tanaka

Department of Medicinal Chemistry

Osaka University of Pharmaceutical Sciences

4-20-1 Nasahara

Takatsuki

Osaka 569-1094

Japan

Telefon: +81-72-690-1084

Fax: +81-72-690-1084

eMail: tanakar@gly.oups.ac.jp