Planta Med 2002; 68(4): 345-348
DOI: 10.1055/s-2002-26744
Original Paper
Natural 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
Further Information

Publication History

June 13, 2001

August 25, 2001

Publication Date:
02 May 2002 (online)

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.

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