Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

Abstract

Two polyketides containing an α-pyrone unit, named penicyrones A (1) and B (2), were isolated from a culture broth of the marine-derived Penicillium sp. TPU1271 together with nine known compounds: verrucosidin (3), fructigenine A (4), verrucofortine (5), cyclo-(L-Trp-L-Phe) (6), cyclopenol (7), cyclopenin (8), penipratynolene (9), aspterric acid (10) and viridicatol (11). The structures of 1 and 2 were elucidated by analyzing the spectroscopic data of 1, 2 and their O-acetyl derivatives (1a and 2a). Compounds 1 and 2 were epimers of each other at the C-9 position. The absolute configurations of 1 and 2 were assigned on the basis of NOESY data for 1, 2, 1a and 2a, a conformational analysis and the identity of the biogenetic pathway with verrucosidin (3). The planar structure of penicyrones was found in the SciFinder as a compound in the commercial chemical libraries; however, the stereostructure and spectroscopic data were not available. Therefore, this is the first study on the isolation and structure elucidation, including the absolute configurations, of penicyrones A (1) and B (2) as fungal metabolites. Compound 3 exhibited growth inhibitory activity against Mycobacterium smegmatis at 40 μg per disc (inhibition zone of 11 mm). This is the first study to demonstrate that verrucosidin (3) exhibited anti-mycobacterial activity.

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

“…Extrolites : Several species in ser. Viridicata produce 4-hydroxy-3,6-dimethyl-2H-pyran-2-one, penicillic acids, cyclopenins / viridicatins, verrucofortines / fructigenines / puberulines, verrucosidins, xanthomegnins, while rather few species produce anacine, aspermytin A / peaurantiogriseols, aspterric acid, asteltoxin, auranthine, aurantiomides, aurantiamine / viridamine, brevianamide A, 4-(9-hydroxy-10-butynoxy)benzoic acid / penipratynolenes, chrysogine, moniliformin, penicyrones, penitrem A, pseurotins, puberulonic acid, terrestric acids, viridic acid ( Frisvad and Samson, 2004b , Ma et al., 2015 , Bu et al., 2016 , Hallas-Moller et al., 2018 , Hamed et al., 2019 ).…”

Rapid Metabolome and Bioactivity Profiling of Fungi Associated with the Leaf and Rhizosphere of the Baltic Seagrass Zostera marina

“…They are also the chemically best-studied genus from which various types of SMs, including polyketides, terpenoids, peptides, and alkaloids, have been reported [48]. Still, they continue providing new SMs [49,50], often due to sampling campaigns conducted at extreme environments, e.g., deep-sea [51]. Afiyatullov and colleagues [14] reported the isolation of a new phthalide derivative from Penicillium claviforme , a surface associated fungus of Z. marina sampled in the Sea of Japan.…”

Natural Polypropionates in 1999–2020: An Overview of Chemical and Biological Diversity

“…The remaining four fungal-derived metabolites, penicyrones A and B ( 123 and 124 ), deoxyverrucosidin ( 125 ) and (+)-neocitreoviridin ( 126 ), were all isolated from Penicillium sp. [ 66 , 67 , 68 ] In the bioassays, 125 dose-dependently inhibited the expression of GRP78 promoter with an IC 50 of 30 nM; meanwhile, 126 exhibited broad-spectrum antiviral effects against influenza A virus (IAV) (IC 50 = 3.6 µM) and antibacterial activity against Helicobacter pylori (including drug-sensitive strain G27 and drug-resistant strain 159) with an MIC of 4 and 16 µg/mL, respectively. A new p -nitrophenyl-possessed polypropionate alloaureothin ( 127 ) with cytotoxicity against HT1080 was obtained from Streptomyces sp.…”