Description and references
Toxic metabolites from Aspergillus ochraceus Wilh.: Scott, Mycopathol. Mycol. Appl. 25, 213 (1965); A. sulphureus and A.
melleus: Lai et al., Appl.
Microbiol. 19, 542 (1970); and Penicillium
viridicatum Westling: van Walbeek et al., Can. J. Microbiol. 15, 1281 (1969).
As these molds occur widely, some toxins have been found as natural
contaminants on corn, peanuts, storage grains, cottonseed and other
decaying vegetation. Isolns: van Walbeek et al., ibid. 14, 131 (1968); Shotwell et al., Appl. Microbiol. 17, 765 (1969); Nesheim, J. Assoc.
Off. Anal. Chem. 52, 975 (1969); Natori et al., Chem. Pharm. Bull. 18, 2259 (1970). Structure and stereochemistry: van
der Merwe et al., J. Chem. Soc. 1965, 7083; Nature 205, 1112 (1965). Synthesis of ochratoxins A, B and
ester deriv: Steyn, Holzapfel, Tetrahedron 23, 4449 (1967); Nesheim, loc. cit.; Roberts,
Woolven, J. Chem. Soc. C 1970, 278. Facile synthesis of A: G. A. Kraus, J. Org. Chem. 46, 201 (1981).
Toxicity study: Purchase, Theron, Food Cosmet.
Toxicol. 6, 479 (1968). Physicochemical data:
A. E. Pohland et al., Pure Appl.
Chem. 54, 2220 (1982). Comprehensive reviews:
Steyn, “Ochratoxin and other Dihydroisocoumarins” in Microbial Toxins vol. VI, A. Ciegler, et al., Eds. (Academic Press, New York, 1971) p 179-205; F.
S. Chu, Crit. Rev. Toxicol. 2, 499-524 (1974); P. Krogh in Natural
Toxins, D. Eaker, P. Wadstr"om, Eds. (Pergamon, New York,
1980) pp 673-680; A. E. Pohland et al., Pure Appl. Chem. 64, 1029-1046
(1992).
Derivative
Ochratoxin A.
Nomenclature
CAS number: 303-47-9
(
R)-
N-[(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1
H-2-benzopyran-7-yl)carbonyl]-
l-phenylalanine.
C
20H
18ClNO
6; mol wt 403.81.
C 59.49%, H 4.49%, Cl 8.78%, N 3.47%, O 23.77%.
Properties
The major ochratoxin component. Crystals from
xylene, mp 169°.
Exhibits green fluorescence. [α]D -118° (c = 1.1 in CHCl3). uv max (ethanol): 215, 333 nm (ε 34000; 2400)
(van der Merwe). Also frequently reported as mp 90° from benzene (one mole of benzene
of crystallization). uv max: 213, 332 nm (ε 36800; 6400) (Steyn, Holzapfel). LD50 orally in rats:
20-22 mg/kg (Purchase, Theron).Derivative
Ochratoxin B.
Nomenclature
CAS number: 4825-86-9
(
R)-
N-[(3,4-Dihydro-8-hydroxy-3-methyl-1-oxo-1
H-2-benzopyran-7-yl)carbonyl]-
l-phenylalanine.
C
20H
19NO
6; mol wt 369.37.
C 65.03%, H 5.18%, N 3.79%, O 25.99%.
Properties
The less toxic dechloro deriv of ochratoxin A.
Crystals from methanol, mp 221° (van der Merwe); also reported as 208-209° (Nesheim). Exhibits
blue fluorescence. [α]D -35° (c = 0.15 in ethanol). uv max: 218, 318 nm (ε 37200, 6900).Derivative
Ochratoxin C.
Nomenclature
CAS number: 4865-85-4
(
R)-
N-[(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1
H-2-benzopyran-7-yl)carbonyl]-
l-phenylalanine ethyl
ester.
C
22H
22ClNO
6; mol wt 431.87.
C 61.18%, H 5.13%, Cl 8.21%, N 3.24%, O 22.23%.
Properties
The equally toxic amorphous ethyl ester of ochratoxin
A: Steyn, Holzapfel, J. S. Afr. Chem. Inst. 20, 186 (1967), C.A. 69, 2797p (1968). uv max (ethanol):
333 nm (ε 6500).Exptlly as teratogen and carcinogen.