Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

The effects of demethylsterigmatocystin and sterigmatin on ATP synthesis system in mitochondria: A comparison with sterigmatocystin

  • 15 Accesses

  • 2 Citations


The effects of demethylsterigmatocystin and its structural isomer, sterigmatin, on oxidative phosphorylation of mitochondria were studied by means of isolated rat liver mitochondria in comparison with sterigmatocystin. Both compounds were found to uncouple the oxidative phosphorylation in mitochondria, causing marked decreases in RC index and P/O ratio. Sterigmatin, in which dihydrobisfuran ring and xanthone nucleus are combined in a linear manner, was evidently more toxic to mitochondrial functions than demethylsterigmatocystin which was an angular molecular shape. Though their uncoupling concentrations were rather high for assessing theirin vivo toxicity, a good correspond was observed between their orders of potencies in the toxicity to mitochondrial functions and in the cytotoxicity to rat hepatocytes. The demethylation of sterigmatocystin resulted in an obvious decrease of uncoupling activity.

This is a preview of subscription content, log in to check access.


  1. 1

    Wogan GN (1977) Mode of action of aflatoxinsin Mycotoxins in Human and Animal Health (eds Rodricks JV, Hesseltine CW and Mehlman MA). Pathotox Publ Co.pp 29-36

  2. 2

    Butler WH (1974) Aflatoxinin Mycotoxins (ed Purchase IFH). Elsevier Sci Publ Co, pp 1-28

  3. 3

    Van der Watt JJ (1974) Sterigmatocystinin Mycotoxins (ed Purchase IFH). Elsevier Sei Publ Co, pp 369-382

  4. 4

    Terao K (1983) Sterigmatocystin — A masked potent carcinogenic mycotoxin. J Toxicol Toxin Reviews 2:77–110

  5. 5

    Terao K and Ito E: The effects of naturally occurring bisdihydrofuran ringcontaining mycotoxins on cultured chick embryonal hepatocytes. Gann 72: 81–91

  6. 6

    Mori H, Sugie S, Yoshimi N, Kitamura J, Niwa M, Hamasaki T, and Kawai K (1986) Genotoxic effects of a variety of sterigmatocystin-related compounds in the hepatocyte/DNA-repair test and the Salmonella microsome assay. Mutation Res. 173:217–222

  7. 7

    Doherty WP and Campbell TC (1973) Aflatoxin inhibiton of rat liver mitochondria. Chem-Biol Interactions 7:63–67

  8. 8

    Kawai K, Nakamaru T, Nozawa Y, Maebayashi Y, Yamazaki M, Natori S (1984) Inhibitory effect of sterigmatocystin and 5,6-dimethoxysterigmatocystin on ATP synthesis in mitochondria. Appl Environ Microbiol 48:1001–1003

  9. 9

    Schneider WC (1948) Intracellular distribution of enzymes III. The oxidation of octanoic acid by rat liver fractions. J Biol Chem 176:259–266

  10. 10

    Chance B and Williams GR (1955) Respiratory enzymes in oxidative phosphorylation I. Kinetics of oxygen utilization. J Biol Chem 217:383–393

  11. 11

    Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with Folin phenol reagent. J Biol Chem 193:265–275

  12. 12

    Hemker HC (1962) Lipid solubility as a factor influencing the activity of uncoupling phenols. Biochim Biophys Acta 63:46–54

  13. 13

    McLaughlin SGA and Dilger JP (1980) Transport of protons across membranes by weak acids. Physiol Rev 60:825–863

Download references

Author information

Correspondence to Kiyoshi Kawai.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Kawai, K., Nakamaru, T., Hisada, K. et al. The effects of demethylsterigmatocystin and sterigmatin on ATP synthesis system in mitochondria: A comparison with sterigmatocystin. Mycotox Res 2, 33–38 (1986).

Download citation

Key Words

  • sterigmatocystin
  • demethylsterigmatocystin
  • sterigmatin
  • uncoupling
  • mitochondria