Abstract
Six new phenalenone derivatives (1–6), along with five known compounds (7–11) of the herqueinone class, were isolated from a marine-derived fungus Penicillium sp. The absolute configurations of these compounds were assigned based on chemical modifications and their specific rotations. 4-Hydroxysclerodin (6) and an acetone adduct of a triketone (7) exhibited moderate anti-angiogenetic and anti-inflammatory activities, respectively, while ent-peniciherqueinone (1) and isoherqueinone (9) exhibited moderate abilities to induce adipogenesis without cytotoxicity.
Highlights
Fungi produce a wide variety of polyketide-derived metabolites
The experimental CD profiles of that it is a phenalenone derivative based on the presence of signals for two aromatic rings and these compounds showed opposite signs in the region of 285–340 nm, possibly reflecting the different a trimethylhydrofuran moiety, which account for eight degrees of unsaturation (Tables 1 and 2)
H3 -40, and H3 -50), an aromatic proton (H-12), and two hydroxy protons a phenalenone derivative based on the presence of signals for two aromatic rings and a (OH-4 and OH-11), with their neighboring carbons confirmed the presence of the trimethylhydrofuran moiety, which account for eight degrees of unsaturation (Tables 1 and 2)
Summary
Fungi produce a wide variety of polyketide-derived metabolites. Among these, phenalenones are a class of hexa- or heptaketides bearing a perinaphtenone-type tricyclic system [1]. Fungi-derived phenalenone compounds have attracted significant interest due to their chemical structures, bioactivities, and biosynthesis [1]. With their diverse phylogenic origins, phenalenones are widely recognized as a representative group of fungal polyketides [1,2]. During the course of our search for novel compounds from marine-derived fungi, we reported the structures of herqueiazole and herqueioxazole, unusual pyrrole- and oxazole-containing phenalenones from a Penicillium sp. Ent-peniciherqueinone (1) and isoherqueinone (9) moderately induced adipogenesis in human bone marrow-mesenchymal stem cells (hBM-MSCs). All of these bioactivities were found to occur without cytotoxicity
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