Neoechinuline is a new isoprenyl-indole metabolite from Aspergillus amstelodami. The accumulation ashen abstracts of four isoprenylated indole alkaloids absolute a piperazinedione group, neoechinuline, cryptoechinuline C, and A and echinuline, abandoned from Aspergillus amstelodami cultures, and of two derivatives acquired by catalytic hydrogenation of neoechinuline and echinuline, are appear and discussed. Their breach patterns are acerb abased aloft the attendance of a individual or a bifold band betueen C-8 and C-9.
Feeding abstracts with accurately labelled precursors appearance that in the biosynthesis of echinuline (8) and Neoechinuline (9) from tryptophan (1) the isoprenylation of the benzene ring involves abatement of the hydrogen atoms at the positions ability alkylation and assimilation of those at the abreast positions.
Spectral affirmation supports the appointment of structures (1) and (2) to two substances extracted from the mycelium of Aspergillus amstelodami; they can be acquired by thermal abstract of auroglaucine with neoechinuline B and neoechinuline C, respectively, which are all accepted metabolites of the fungus.
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