84 放線菌の生産するインドールアルカロイド発癌プロモーターの構造と生理活性

概要

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Carcinogenic promoters produced by microorganisms were sought using the Epstein-Barr virus early antigen (EBV-EA) induction test, a short-term promoter test system, and one strain, Streptoverticillium blastmyceticum NA34-17, was found to induce potent EBV-EA. Nine biologically-active indole alkaloids were isolated from the cultured broth and mycelia. They were identified as teleocidin B-4 (1), (-)-indolactam V (2), (-)-14-O-acetyl indolactam V (3), (-)-2-oxy-indolactam V, (4), (-)-N^<13>-desmethyl indolactam V (5), N-acetyl-L-tryptophanol (6), olivoretin A (7), B (8), and C (9). This is the first experiment on the isolation of compounds 2-6 from natural sources. Of the above metabolites, (-)-indolactam V (2) is a key compound for investigating the ralationship between the structure of teleocidin-related compounds and the activity of the EBV-EA induction, because its structure is fundamental to teleocidins. A number of new (-)-indolactam V derivatives (11-31) were prepared and their EBV-EA-inducing activity was tested (Table 1). The alkylation of hydroxymethyl at C-14 or imino group at N-1 lowered the activity, while the substitution of indole ring at C-7 with a halogen atom enhanced the activity. The structure-activity relationship was in detail discussed.
天然有機化合物討論会の論文
1985-09-07