182. Aflatoxins M
Description and references
Highly toxic 4-hydroxylated aflatoxin B derivs found in the milk of cows fed toxic meal. Initial reports: Allcroft, Carnaghan, Vet. Rec. 75, 259 (1963). Isoln: De Iongh et al., Nature 202, 466 (1964); Allcroft et al., ibid. 209, 154 (1966). Isoln and structure of M1 and M2: C. W. Holzapfel, P. S. Steyn, Tetrahedron Lett. 1966, 2799. Total synthesis of M1: Büchi, Weinreb, J. Am. Chem. Soc. 91, 5408 (1969); 93, 746 (1971); G. Büchi et al., ibid. 103, 3497 (1981). Carcinogenicity studies: Wogan, Paglialunga, Food Cosmet. Toxicol. 12, 381 (1974). For general refs see Aflatoxins B.
Derivative
Aflatoxin M1.Nomenclature
CAS number: 6795-23-9
(6aR,9aR)-2,3,6a,9a-Tetrahydro-9a-hydroxy-4-methoxycyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione; 4-hydroxyaflatoxin B1. C17H12O7; mol wt 328.27.
C 62.20%, H 3.68%, O 34.12%.
Properties
Crystals from methanol, mp 299° (dec). Exhibits blue-violet fluorescence. [α]D 280° (c = 0.1 in DMF). uv max (ethanol): 226, 265, 357 nm (ε 23100, 11600, 19000). LD50 orally in day old Pekin ducklings: 16.6 μg/duckling (Holzapfel, Steyn).Derivative
Aflatoxin M2.Nomenclature
CAS number: 6885-57-0
2,3,6a,8,9,9a-Hexahydro-9a-hydroxy-4-methoxycyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione; 4-hydroxyaflatoxin B2. C17H14O7; mol wt 330.29.
C 61.82%, H 4.27%, O 33.91%.
Description and references
The 8,9-dihydro deriv of aflatoxin M1.