The Structures of Aflatoxins B and G1

Asao, Tsutomu; Buechi, George; Abdel-Kader, M. M.; Chang, S. B.; Wick, Emily L.; Wogan, G. N.

doi:10.1021/ja01082a031

Cited by 208 publications

(75 citation statements)

References 2 publications

(3 reference statements)

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“…Aflatoxin B 1 was discovered in the early 1960s as the etiological agent of 'Turkey X' disease, responsible for the widespread deaths of turkeys and other poultry throughout Europe due to contaminated Brazilian peanut meal in feed [Asao et al, 1965]. We recently cloned and expressed P4501A5 from turkey liver, which like the human homologue, P4501A2, efficiently epoxidates AFB 1 to produce the exo-AFBO as well as the detoxified metabolite aflatoxin M 1 [Yip and Coulombe, 2006].…”

mentioning

confidence: 99%

Structure, Genetic Mapping, and Function of the Cytochrome P450 3A37 Gene in the Turkey (Meleagris gallopavo)

Rawal

Mendoza

Reed

et al. 2009

Cytogenet Genome Res

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Cytochromes P450 (P450 for protein; CYP for gene) are a superfamily of membrane-bound hemoproteins that oxidize a large number of endogenous and exogenous compounds. Through oxidation reactions, these enzymes are often responsible for the toxic and carcinogenic effects of natural food-borne toxicants, such as the mycotoxin aflatoxin B₁ (AFB₁). Previous studies in our laboratory have shown that the extreme sensitivity of turkeys to AFB₁ is in part explained by efficient hepatic P450-mediated epoxidation to the toxic and reactive metabolite the exo-AFB₁-8,9-epoxide (AFBO). Using 3′-5′-rapid amplification of cDNA ends (RACE), we amplified CYP3A37 from turkey liver RNA, the E. coli-expressed protein which efficiently epoxidates AFB₁. Turkey CYP3A37 has an ORF of 1512 bp, and the protein is predicted to be 504 amino acids with 97% homology to chicken CYP3A37. The turkey gene is organized into 13 exons and 12 introns. A single nucleotide polymorphism in the 11th intron was used to assign CYP3A37 to turkey linkage group 10 (corresponding to chicken chromosome 14, GGA14). Because of the important role of P450s in the extreme sensitivity of turkeys to the toxic effects of AFB₁, this study will contribute to the identifying allelic variants of this important gene in poultry.

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confidence: 99%

Structure, Genetic Mapping, and Function of the Cytochrome P450 3A37 Gene in the Turkey (Meleagris gallopavo)

Rawal

Mendoza

Reed

et al. 2009

Cytogenet Genome Res

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“…The small coupling constant and the large difference in their chemical shifts indicate they are located on a highly polarized Z-olefin. This suggested the presence of the bis-dihydrofuran moiety, typical of the aflatoxins (15). Such a structure also accounts for two low-field singlets at 6 6.44 and 6.46.…”

Section: Discussionmentioning

confidence: 87%

Metabolites of the honey mushroom, Armillariamellea

Ayer¹,

Macaulay²

1987

Can. J. Chem.

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The fungus Armillariamellea (Vahl ex. Fr.) Kummer is responsible for severe losses in timber and fruit production. The metabolites isolated when certain strains of this fungus are grown in liquid culture have been identified as diterpenoid acids possessing the abietane (1) and pimarane (2) skeletons. These compounds, known collectively as resin acids, have not been reported previously from a fungal source. In addition to the resin acids dehydroabietic acid (3), pimaric acid (4), isopimaric acid (5), and sandaracopimaric acid (6), three additional acids, levopimaric acid endo-peroxide (7), 7-oxodehydroabietic acid (9), and 7-oxo-15-hydroxydehydroabietic acid (10) were obtained. On one occasion three orange pigments, austocystin F (11), averufin (12), and averufanin (13), all previously known fungal metabolites, were isolated.

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“…The discovery that the toxins had a characteristic fluorescence pattern on thin-layer chromatograms greatly facilitated their isolation and characterization, culminating in the determination of the molecular formulas of four components designated as aflatoxins Bi, B2, Gi, and G2; the four components were distinguished by their blue or green fluorescence and by their Rf values on thin-layer chromatograms (87). More recently, related substances have been isolated and chemically characterized, the most important ones being Mi, M2, B2, and G2a (63).…”

Section: Identification and Characterization Of Aflatoxinsmentioning

confidence: 99%

Mycotoxins: Toxicity, Carcinogenicity, and the Influence of Various Nutritional Conditions

Newberne¹

1974

Environmental Health Perspectives

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The Structures of Aflatoxins B and G₁

Cited by 208 publications

References 2 publications

Structure, Genetic Mapping, and Function of the Cytochrome P450 3A37 Gene in the Turkey <i>(Meleagris gallopavo)</i>

Structure, Genetic Mapping, and Function of the Cytochrome P450 3A37 Gene in the Turkey <i>(Meleagris gallopavo)</i>

Metabolites of the honey mushroom, Armillariamellea

Mycotoxins: Toxicity, Carcinogenicity, and the Influence of Various Nutritional Conditions

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