Alkaloids with Cardiovascular Effects from the Marine-Derived Fungus Penicillium expansum Y32

Abstract

Three new alkaloids (1, 4 and 8), together with nine known analogues (2, 3, 5–7, and 9–12), were isolated from the marine-derived fungus Penicillium expansum Y32. Their structures including the absolute configurations were elucidated by spectroscopic and Mosher’s and Marfey’s methods, along with quantum electronic circular dichroism (ECD) calculations. Each of the compounds was evaluated for cardiovascular effects in a live zebrafish model. All of the compounds showed a significant mitigative effect on bradycardia caused by astemizole (ASM) in the heart rate experiments. Compounds 4–6 and 8–12 exhibited potent vasculogenetic activity in vasculogenesis experiments. This is the first study to report that these types of compounds show cardiovascular effects in zebrafish. The results suggest that these compounds could be promising candidates for cardiovascular disease lead compounds.

Bioactive Compounds Produced by Strains of Penicillium and Talaromyces of Marine Origin

“…Insect neurotoxicity was also observed in assays carried out on larvae of the bluebottle fly ( Calliphora vomitoria ) [ 94 ]. Moreover, in a study employing a zebra-fish model, communesin I and two more novel compounds, fumiquinazoline Q and protuboxepin E, were reported for cardiotonic effects, as well as some extent of vasculogenetic properties assessed with reference to both number and length of vessels [ 168 ].…”

Faculty Opinions recommendation of Oxepinamide F biosynthesis involves enzymatic D-aminoacyl epimerization, 3H-oxepin formation, and hydroxylation induced double bond migration.

“…Typical signals for oxepins were not observed in the NMR spectra of 3. Extensive interpretation of the spectroscopic data including NMR and CD spectra and comparison with known compounds 16 proved 3 to be protuboxepin K, a quinazolinone derivative of Ant, D-Phe, and L-Ile (Fig. 3) 17 .…”

Marine-derived fungi as a source of bioactive indole alkaloids with diversified structures

“…As a result, isopropylchaetominine (324) was isolated, which showed strong cytotoxicity against the mouse lymphoma cell line L5178Y with an IC 50 value of 0.4 μmol/L (Özkaya et al 2018). Fumiquinazoline Q (325), isolated from the marine-derived fungus P. expansum Y32, exhibited potent vasculogenetic activity in vasculogenesis experiments, which suggested that it could be a promising candidate for cardiovascular disease lead compound (Fan et al 2015).…”