Dihydrocarbazole Alkaloids from Aspergillus tubingensis

Journal of Natural Products
2001.0

Abstract

Investigation of the fungus Aspergillus tubingensis (ATCC 76608, Trichocomaceae) has led to the isolation and identification of two new indole diterpenes, dihydrotubingensin A (1) and dihydrotubingensin B (2). Compounds 1 and 2 were isolated from the methyl ethyl ketone (MEK) extract of A. tubingensis along with two previously reported metabolites, tubingensins A (3)1 and B (4).2 As a class, these fungal metabolites hold considerable interest due to the rare dihydrocarbazole unit. In fact, this is the first known report that describes the isolation of a dihydrocarbazole from a living system.3 The occurrence of 1-4 in the extract of A. tubingensis suggests that the dihydro compounds 1 and 2 may represent the incipient state of these metabolites, while tubingensins A and B are the nonnatural oxidation products. Details of the isolation and structure elucidation of 1 and 2 are reported herein.

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