Inhibitor Report for: TerritremC

The 1H- and 13C-nmr assignments of territrems A, B, and C [1-3] were made by using nOe and 2D nmr techniques. Following the same methods, the structure of MB2 [4], the major product of territrem B incubated with rat liver microsomal fraction, was determined as a hydroxylation product at the pro S methyl group of C-4 of territrem B.

Male Wistar rats were pretreated with phenobarbital, 3-methyl-cholanthrene, or polychlorinated biphenyl. The S9 fraction was isolated from their livers. An amount of 40-microliters territrem (TRA, B, or C) (1 mg/ml methanol) was added to 5-ml reaction mixtures containing S9 (8 mg protein), NADP sodium salt (20 mumol), glucose-6-phosphate monosodium salt (25 mumol), MgCl2 (40 mumol), KCl (165 mumol), and sodium phosphate buffer, 0.1 M, pH 7.4, after preincubation for 5 min. Further incubation was carried out for 30 min by shaking (100 ocillations/min). The reaction was stopped by adding 2 ml acetone. The acetone was then removed by evaporation in a hood at room temperature. The residue was lyophilized and extracted with 2 ml methanol 3 times. When TRB was a substrate, at least four blue fluorescent products, designated as MB1, MB2, MB3, and MB4, were found in the methanol extract by TLC under view of long-wave UV light. MB2 was the major product. When TRA or TRC was a substrate, two products, MA1 (the major product) and MA2 from TRA, and one product, MC from TRC, were, respectively, detected in the methanol extract. The formation of the products was dependent on the presence of S9, NADP, glucose-6-phosphate, and territrem. The reaction was enhanced by pretreatment of rats with phenobarbital. It was demonstrated that MB2 and MA1 are hydroxylated products of the methyl group at the C4 position of TRB and TRA. MB4 was identified as TRC. MC was shown to be identical to MB1, which was the hydroxylated product at the methyl group of C4 position of TRC.

Territrem C, a new tremorgenic mycotoxin (C28H32O9; molecular weight, 512.20) was isolated from the chloroform extract of rice cultures of Aspergillus terreus 23-1, which also produces territrems A and B. Isolation, acute toxicity, and some physicochemical properties of territrem C are discussed in this paper. The spectral and chemical evidence indicated that the structural difference between territrem C and territrem B (C29H34O9) was in their phenyl moieties: a 4-hydroxy-3,5-dimethoxy phenyl group in territrem C and a 3,4,5-trimethoxy phenyl group in territrem B. It was also demonstrated that territrem B was obtained by methylation of territrem C with dimethyl sulfate.

The 1H- and 13C-nmr assignments of territrems A, B, and C [1-3] were made by using nOe and 2D nmr techniques. Following the same methods, the structure of MB2 [4], the major product of territrem B incubated with rat liver microsomal fraction, was determined as a hydroxylation product at the pro S methyl group of C-4 of territrem B.

Male Wistar rats were pretreated with phenobarbital, 3-methyl-cholanthrene, or polychlorinated biphenyl. The S9 fraction was isolated from their livers. An amount of 40-microliters territrem (TRA, B, or C) (1 mg/ml methanol) was added to 5-ml reaction mixtures containing S9 (8 mg protein), NADP sodium salt (20 mumol), glucose-6-phosphate monosodium salt (25 mumol), MgCl2 (40 mumol), KCl (165 mumol), and sodium phosphate buffer, 0.1 M, pH 7.4, after preincubation for 5 min. Further incubation was carried out for 30 min by shaking (100 ocillations/min). The reaction was stopped by adding 2 ml acetone. The acetone was then removed by evaporation in a hood at room temperature. The residue was lyophilized and extracted with 2 ml methanol 3 times. When TRB was a substrate, at least four blue fluorescent products, designated as MB1, MB2, MB3, and MB4, were found in the methanol extract by TLC under view of long-wave UV light. MB2 was the major product. When TRA or TRC was a substrate, two products, MA1 (the major product) and MA2 from TRA, and one product, MC from TRC, were, respectively, detected in the methanol extract. The formation of the products was dependent on the presence of S9, NADP, glucose-6-phosphate, and territrem. The reaction was enhanced by pretreatment of rats with phenobarbital. It was demonstrated that MB2 and MA1 are hydroxylated products of the methyl group at the C4 position of TRB and TRA. MB4 was identified as TRC. MC was shown to be identical to MB1, which was the hydroxylated product at the methyl group of C4 position of TRC.

Territrem C, a new tremorgenic mycotoxin (C28H32O9; molecular weight, 512.20) was isolated from the chloroform extract of rice cultures of Aspergillus terreus 23-1, which also produces territrems A and B. Isolation, acute toxicity, and some physicochemical properties of territrem C are discussed in this paper. The spectral and chemical evidence indicated that the structural difference between territrem C and territrem B (C29H34O9) was in their phenyl moieties: a 4-hydroxy-3,5-dimethoxy phenyl group in territrem C and a 3,4,5-trimethoxy phenyl group in territrem B. It was also demonstrated that territrem B was obtained by methylation of territrem C with dimethyl sulfate.