Planta Medica, Table of Contents Planta Med 2002; 68(4): 345-348DOI: 10.1055/s-2002-26744 Original PaperNatural Product Chemistry© Georg Thieme Verlag Stuttgart · New York(3R,6R)-4-Methyl-6-(1-methylethyl)-3-phenylmethyl-perhydro-1,4-oxazine-2,5-dione: An Apoptosis-Inducer from the Fruiting Bodies of Isaria japonica Hyuncheol Oh1 , Taewan Kim2 , Gi-Su Oh2 , Hyun-Ock Pae2 , Kyung-Hwan Hong2 , Kyu-Yun Chai2 , Tae-Oh Kwon2 , Hun-Taeg Chung2 , Ho-Sub Lee1 1Professional Graduate School of Oriental Medicine, Wonkwang University, Iksan, Chonbuk, Republic of Korea 2Medicinal Resources Research Center, Wonkwang University, Iksan, Chonbuk, Republic of Korea Recommend Article Abstract Buy Article(opens in new window) Abstract (3R,6R)-4-Methyl-6-(1-methylethyl)-3-phenylmethylperhydro-1,4-oxazine-2,5-dione (1) was isolated from the fruiting bodies of Isaria japonica as an apoptosis-inducing agent. The complete structural assignment of the compound was accomplished on the basis of spectroscopic methods and chemical transformations. Compound 1 induced apoptotic cell death of the human leukemia cells (HL-60) in a dose-dependent manner, ranging from 5.0 μg/ml to 100.0 μg/ml. Key words Isaria japonica - fungal metabolite - dixomorpholine - human HL-60 leukemia cell - apoptosis Full Text References References 1 Takano F, Kikuchi Y, Fushiya S, Hojo H, Nozoe S, Yahagi N, Kondo Y. The culture fluid of Isaria japonica Yasuda augments anti-sheep red blood cell antibody response in mice. Biological & Pharmaceutical Bulletin. 1996; 19 641-3 2 Bok J W, Lermer L, Chilton J, Klingeman H G, Neil Towers G H. Antitumor sterols from the mycelia of Cordyceps sinensis . Phytochemistry. 1999; 51 891-8 3 Cory J G, Suhadolink R J, Resnick B, Rich M A. Incorporation of cordycepin (3’-deoxyadenosine) into ribonucleic acid and deoxyribonucleic acid of human tumor cells. Biochimica et Biophysica Acta. 1965; 103 646-53 4 Furuya T, Hirotani M, Matsuzawa M. N 6-(2-Hydroxyethyl)adenosine, A biologically active compound from cultured mycelia of Cordyceps and Isaria species. Phytochemistry. 1983; 22 2509-12 5 Fusita T, Inoue K, Yamamoto S, Ikumoto T, Sasaki S, Toyama R, Chiba K, Hoshino Y, Okumoto T. Fungal metabolites. Part II. A potent immunosuppressive activity found in Isaria sinclairii metabolites. Journal of Antibiotics. 1994; 47 208-15 6 Story M, Kodym R. Signal transduction during apoptosis: Implications for cancer therapy. Frontiers in Bioscience. 1998; 3 365-75 7 McConkey D J. Biochemical determinants of apoptosis and necrosis. Toxicology Letters. 1998; 99 157-68 8 Fadeel B, Orrenius S, Zhivotovsky B. apoptosis in human disease: A new skin for the old ceremony?. Biochemical and Biophysical Research Communications. 1999; 266 699-717 9 Oh G -S, Hong K-W, Oh H, Pae H -O, Seo W -G, Kim I -K, Kim N -Y, Kwon T -O, Shin M -K, Chung H -T. 4-Acetyl-12,13-epoxyl-9-trichothecene-3,15-diol isolated from the fruiting bodies of Isaria japonica Yasuda induces apoptosis of human leukemia cells (HL-60). Biological & Pharmaceutical Bulletin. 2001; 24 785-9 10 Hasumi K, Shinohara C, Iwanaga T, Endo A. Lateritin, a new inhibitor of acyl-CoA:cholesterol acyltransferase produced by Gibberella lateritium IFO 7188. Journal of Antibiotics. 1993; 46 1782-7 11 Kagamizono T, Nishino E, Matsumoto K, Kawashima A, Kishimoto M, Sakai N, He B -M, Chen Z -X, Adachi T, Morimoto S, Hanada K. Bassiatin, a new platelet aggregation inhibitor produced by Beauveria basiana K-717. Journal of Antibiotics. 1995; 48 1407-12 Prof. Ho-Sub Lee Professional Graduate School of Oriental Medicine Wonkwang University Iksan 570-749 Korea Email: host@wonkwang.ac.kr Fax: +82-63-850-7324
