Three New Indole‐Containing Diketopiperazine Alkaloids from a Deep‐Ocean Sediment Derived Fungus Penicillium griseofulvum

Abstract

Three new indole-containing diketopiperazine alkaloids, named variecolorins M -O (1 -3), together with the eight known analogues 4 -11, were isolated from a deep-ocean sediment-derived fungus, Penicillium griseofulvum. Their structures were determined by analysis of the spectroscopic data. The 2,2-diphenyl-1-picrylhydrazinyl (DPPH) radical-scavenging activities and the cell-proliferation inhibitory activities of the three new compounds 1 -3 were investigated.

Isolation of Aromatic Compounds Produced by Eurotium herbariorum NU-2 from Karebushi, a Katsuobushi, and their DPPH-Radical Scavenging Activities

“…The compounds (C1-C6) were previously isolated from Aspergillus variecolor and Penicillium griseofulvum (Wang et al, 2007a;Zhou et al, 2010). Benzaldehyde derivatives were identified as tetrahydroauroglaucin (D1), isodihydroauroglaucin (D2), and flavoglaucin (D3).…”

“…Neoechinulin A (C3), tetrahydroauroglaucin (D1), isodihydroauroglaucin (D2), and flavoglaucin (D3) were previously isolated from mold-starters used in making karebushi (Yagi and Doi, 1999;Miyake et al, 2009;2010). However, for the first time, the aromatic compounds (A1-A6, B1, B2, C1, C2, C4-C6) were isolated from a mold-starter used in making karebushi.…”

Synthetic and Structure-Activity Relationship Studies on Bioactive Natural Products

“…Bridelia ferruginea (Euphorbiaceae), 45) Eurotium sp., [46][47][48][49] Penicillium griseofulvum, 50) and the aerial parts of Plumbago zeylanica.…”

New Deoxyisoaustamide Derivative from the Marine-derived Fungus Penicillium sp. JF-72

“…Penicillium species are known to produce numerous alkaloids, in which some diketopiperazine-type alkaloids have been reported so far. [1][2][3][4][5] In the course of our on-going research on the secondary metabolites of marinederived fungi, we have investigated the chemistry of the methylethylketone extract of the Penicillium sp. JF-72, and the study resulted in the isolation of three indole-containing diketopiperazine alkaloids (1)(2)(3), including a new natural compound (2) and a new metabolite (3).…”

“…The absolute configuration of compound 2 was determined based on the biogenetic considerations of diketopiperazine alkaloids isolated from the fungal genus Penecillium, [1][2][3][4][5] and NOESY correlation between H-11 and H-17. In addition, comparison of its optical rotation value, + 140 (c 0.04, CHCl 3 ) with the reported compound was in good agreement with this assignment.…”