Griseofulvin Derivative and Indole Alkaloids from <i>Penicillium griseofulvum</i> CPCC 400528

Abstract

A new griseofulvin derivative, 4′-demethoxy-4′- N -isopentylisogriseofulvin ( 1 ), three new indole alkaloids, 2-demethylcyclopiamide E ( 2 ), 2-demethylsperadine F ( 3 ), and clopiamine C ( 4 ), and five known metabolites ( 5 – 9 ) were isolated from Penicillium griseofulvum CPCC 400528. Compound 1 is the first reported griseofulvin analogue with an N -isopentane group and the first example of a naturally occurring N-containing griseofulvin analogue. Their structures and absolute configurations were elucidated through extensive spectroscopic analyses, calculated ECD, and single-crystal X-ray diffraction (Cu Kα). The possible biogenetic pathway of 1 – 3 was proposed. Compounds 1, 2, and 5 exhibited anti-HIV activities with IC 50 values of 33.2, 20.5, and 12.6 μM, respectively.