A Quinone Isolated from the Nest of Vespa simillima and Its Growth-Inhibitory Effect on Rat Liver Cancer Cells

• Published in: Biological & Pharmaceutical Bulletin Vol. 31; no. 4; pp. 722 - 725
• Main Authors: Fujiwara, Yumiko, Mangetsu, Makoto, Yang, Ping, Kofujita, Hisayoshi, Suzuki, Koichi, Ohfune, Yasufumi, Shinada, Tetsuro
• Format: Journal Article
• Language: English; Japanese
• Published: Japan The Pharmaceutical Society of Japan 01.04.2008; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: Animals; Antineoplastic Agents; Carcinoma, Hepatocellular - drug therapy; Carcinoma, Hepatocellular - pathology; Cell Line, Tumor; cytotoxicity; Diterpenes - isolation & purification; Diterpenes - pharmacology; Dose-Response Relationship, Drug; Hymenoptera; Liver cancer; Liver Neoplasms - drug therapy; Liver Neoplasms - pathology; Magnetic Resonance Spectroscopy; nest material; quinone; Quinones - isolation & purification; Quinones - pharmacology; Rats; social wasp; Spectrometry, Mass, Electrospray Ionization; Spectroscopy, Fourier Transform Infrared; Vespa; Vespidae; Vespinae; Wasps - chemistry
• ISSN: 0918-6158; 1347-5215
• DOI: 10.1248/bpb.31.722

A biologically active quinone that exhibits a growth-inhibitory effect on rat liver cancer cells was isolated from the nest of a social wasp, Vespa simillima (Vespinae, Vespidae). The structure was unambiguously determined by NMR and synthetic experiments and identified as being 7,8-seco-para-ferruginone. The synthetic quinone showed potent growth-inhibitory effects on rat hepatoma cells (IC50 value=1.9 μM). Morphological analyses of dRLh84 cells using the synthetic compound were tested. Chromatin coagulation was induced by the synthetic compound at 31.6 μM.