9149. Tenuazonic Acid

Nomenclature

CAS number: 610-88-8
(5S)-3-Acetyl-1,5-dihydro-4-hydroxy-5-[(1S)-1-methylpropyl]-2H-pyrrol-2-one; l-3-acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one; l-3-acetyl-5-sec-butyltetramic acid.
C10H15NO3; mol wt 197.23.
C 60.90%, H 7.67%, N 7.10%, O 24.34%.

Description and references

Mycotoxin produced by Alternaria alternata and other fungal species; contaminant found in wheat and other grains, sunflower seeds, tomatoes and other fruits. Isoln from culture filtrates of Alternaria tenuis Auct.: T. Rosett et al., Biochem. J. 67, 390 (1957). Structure: C. E. Stickings, Biochem. J. 72, 332 (1959). Biosynthesis: C. E. Stickings, R. J. Townsend, ibid. 78, 412 (1961). Chemical synthesis: R. N. Lacey, J. Chem. Soc. 1954, 850; S. A. Harris et al., J. Med. Chem. 8, 478 (1965); R. Schobert et al., Org. Biomol. Chem. 2, 3524 (2004). Tumor inhibitory properties: E. A. Kaczka et al., Biochem. Biophys. Res. Commun. 14, 54 (1964); C. O. Gitterman et al., Cancer Res. 24, 440 (1964). Toxicity of isolates from agricultural samples: R. A. Meronuck et al., Appl. Microbiol. 23, 613 (1972). Review of analytical methods and occurrence in foods: P. M. Scott, J. AOAC Int. 84, 1809-1817 (2001).

Chemical structure

Properties

Pale brown, viscous, gummy substance, [α]20D -128° (c = 1.0 in methanol); -132 ± 2° (c = 0.5 in CHCl3). bp0.035 117°. Readily sol in organic solvents incl petr ether; sparingly sol in water. On long standing, changes into the crystalline iso-form.

Derivative

Sodium salt.

Nomenclature

CAS number: 1013-59-8
Sodium l-tenuazonate.
C10H14NNaO3; mol wt 219.21.
C 54.79%, H 6.44%, N 6.39%, Na 10.49%, O 21.90%.

Properties

[α]546 -96.7° (c = 2.0 in methanol). uv max (pH 7): 280, 241 nm (E1%1 cm 573, 400).