Terretonins E and F, Inhibitors of the Mitochondrial Respiratory Chain from the Marine-Derived Fungus Aspergillus insuetus

Abstract

Two new meroterpenoids, terretonins E and F (1, 2), together with three known compounds, aurantiamine (3), linoleic acid, and uridine, were isolated as fermentation products of the marine-derived fungus Aspergillus insuetus, which was associated with the sponge Petrosia ficiformis. Structures of all isolates were elucidated employing spectroscopic methods, mainly by two-dimensional NMR techniques. Compounds 1-3 showed activity as inhibitors of the mammalian mitochondrial respiratory chain.

Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

“…The total EtOAc-soluble fraction (35.5 g) was subjected to stepgradient silica gel column chromatography (CC) with a solvent system consisting of 0-100% petroleum ether (PE)-EtOAc to afford 14 fractions (Frs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] on the basis of TLC analysis. Fr.…”

“…1,2 Aspergillus ustus (A. insuetus) has been proven to be a prolific producer of terpenes, containing sesquiterpenes, sesterterpenes, and meroterpenes. [3][4][5][6][7] However, most of them have been assigned only relative configurations, and their absolute configurations remain unresolved. In our ongoing program to discover new bioactive compounds from marine algae and their associated fungi, a fungus A. ustus isolated from the marine green alga Codium fragile was investigated.…”

New Butyrolactone From a Marine-Derived Fungus Aspergillus Sp

“…led to the isolation of 4 compounds 1-4: one new, 1, and three known compounds, named butyrolactone I, 2 11 , and the two sesterterpenoids terretonin A, 3 and terretonin B, 4 8,9 . The structures of the known compounds were confirmed by comparing their spectroscopic properties with those reported [8][9][10][11][12][13] . Compound 1 was obtained as colourless crystals.…”

“…As part of our research on marine fungi, we report here the results regarding the secondary metabolite chemistry of 2P-22 strain, Aspergillus sp., isolated from the marine sponge Cliona chilensis collected in Los Molles, IV Region, Chile. This study led to the isolation of a new compound 1, together with three known compounds previously isolated from other fungal sources [8][9][10][11] ( Figure 1). The new compound is structurally related to the known butyrolactone I isolated from Aspergillus terreus.…”

“…From the purification by chromatography on silica gel using as mobile phase hexane/EtOAc (8:3), fractions 15 and 18 contained compounds 3 and 4 respectively. Compounds 2 -4 were identified by comparison of their spectroscopic properties with those reported [8][9][10][11][12][13] . 13 C-NMR: 169.7 (C-1), 85.9 (C-2), 38.7 (C-3), 128.0 (C-4), 132.1 (C-5), 118.2 (C-6), 151.9 (C-7), 116.7 (C-8), 129.6 (C-9), 31.0 (C-10), 69.6 (C-11), 77.2 (C-12), 24.6 ( C-13), 22.4 (C-14), 169.2 (C-1'), 137.4 (C-2'), 124.7 (C-3'), 128.0 (C-4'), 129.5 (C-5' and C-9'), 116.0 (C-6' and C-8'), 156.6 (C-7').…”