Bioactive Polyhydroxanthones from Penicillium purpurogenum

Abstract

Eight new polyhydroxanthones, penicixanthones A−H (1−8), including four monomers (1−4) and four dimers (5− 8), were isolated from solid cultures of Penicillium purpurogenum SC0070. Their structures were elucidated by extensive spectroscopic analysis, X-ray single-crystal diffraction, and theoretical computations of ECD spectra. Penicixanthone B (2) has a hexahydroxanthone structure featuring an unusual oxygen bridge between C-6 and C-8a. Penicixanthone D ( 4) is distinct from other penicixanthones in stereochemistry, and its biosynthetic mechanism was proposed based on theoretical simulations for the reaction pathway of C-10a epimerization. Penicixanthone G (6) exhibited the most potent cytotoxicity (IC 50 : 0.3−0.6 μM) when tested against human carcinoma A549, HeLa, and HepG2 cells, whereas it was nontoxic to the normal Vero cells (IC 50 > 50 μM). It also displayed the strongest antibacterial activity (MIC: 0.4 μg/mL) against both Staphylococcus aureus and the methicillin-resistant strain MRSA.

Subplenones A–J: Dimeric Xanthones with Antibacterial Activity from the Endophytic Fungus Subplenodomus sp. CPCC 401465

“…After subsequent isolation and purification we were able to confirm the identity of calyxanthone (12, m/z 287.1) and identified the other compounds as alternaphenol B (11, m/z 271.9), 16 penicixanthone D (13 m/z 295.5), 17 and an as yet unknown xanthone (m/z 547.1) (Figures S92−S97).…”

New dimeric chromanone derivatives from the mutant strains of Penicillium oxalicum and their bioactivities

“…The IR spectrum displayed absorption bands at 3422, 1783, 1676, and 1624 cm À1 , which indicated the existence of hydroxyl, carbonyl and aromatic moieties. The 1 H NMR spectrum (Table 1) 6 and 53.0), and two methyl carbons (d C 14.7 and 13.9). The 1 H NMR and 13 C NMR spectroscopic data of 1 were similar to those of paecillin D (5) (Tables S10 and S11 †).…”

“…Fungi have been demonstrated to be an important resource which could produce biologically active compounds with diverse chemical structures. [1][2][3][4] The Penicillium genus composed of over 200 species is one of the largest groups of fungi, 5 and a large quantity of secondary metabolites with varied architectural features and potent biological activities are isolated from Penicillium, including polyketides, [6][7][8] terpenoids, [9][10][11] alkaloids, [12][13][14] and macrolides. [15][16][17] The chromanone dimer is a structurally complex polyketide widely distributed in several genera of fungi, exemplied by Aspergillus, 18,19 Xylaria, 20 Penicillium, 21,22 Setophoma, 23 and Gonytrichum, 24,25 which display cytotoxic, 18,19 antimicrobial, 23 and innate immunepromoting 24,25 activities.…”

Study on Bioactive Secondary Metabolites from Penicillium herquei JX4

“…Endophytic fungi are widely recognized as a prolific source of structurally unique and biologically active natural products. [1][2][3] Many biologically active secondary metabolites have been isolated from the genus Penicillium, for example, antifungal sesquiterpenoid, [4] cytotoxicity penicixanthone G, [5] anti-human immunodeficiency virus (HIV) cyclopiamide, [6] and anti-inflammatory penazaphilone I. [7] In our previous research bioactive metabolites from mangrove fungi in the South China Sea, two epimer pairs of acetaminophen derivatives penicilqueis A～D [8] were isolated from Penicillium herquei JX4.…”