Structures and biological activities of brominated azaphilones produced by Penicillium sclerotiorum E23Y–1A

Comprehensive Analysis of Penicillium Sclerotiorum: Biology, Secondary Metabolites, and Bioactive Compound Potential─A Review

“…Some of the methods are by using column chromatography such as Thin Layer Chromatography (TLC), High Performance Liquid Chromatography (HPLC), High-resolution electrospray ionization mass spectrometry (HRESIMS), Mass Spectroscopy (MS), Nuclear Magnetic Resonance (NMR), X-ray single-crystal diffraction, and Ultraviolet Visible Spectroscopy (UV–vis). ,, In this review, total, 85 secondary metabolites were described to be biosynthesized by this P. sclerotiorum (Table ), encompassing azaphilonidal derivatives, meroterpenoids, polyketides, and peptides. Most of the metabolites that can be extracted and isolated from P. sclerotiorum azaphilones groups such Chlorogeumasnol ( 1 ), epi -geumsanol D ( 2 ), 8a- epi -eupenicilazaphilone C ( 3 ), 8a- epi -hypocrellone A ( 4 ), eupenicilazaphilone C (5) , 5-bromoisorotiorin ( 6 ), 5-bromosclerotiorin (7) , 5-chloro-3-[(1E,3R,4R,5S)-3,4-dihydroxy-3,5-dimethyl-1-hepten-1-yl]-1,7,8,8a-tetrahydro-7,8-dihydroxy-7-methyl-(7R,8R,8aS)-6 H -2-benzopyran-6-one (8) , 7-deacetylisochromophilone VI (9) , ((1 E ,3 E )-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (10) , Isochromophilone IV (11) , Isochromophilone H (12) , Isochromophilone J (13) , Ochlephilone (14) , Penazaphilones A–I (15–23) , Penazaphilone J–L (24–26) , , Peniazaphilone A–E (27–31) , ,, Penicilazaphilone B (32) , Penicilazaphilone C (33) , Penicilazaphilones D-E (34–35), Penicilazaphilone F–G (36–37) , Penicilazaphilone I–N (38–43) , Penicilazaphilones H (44) , Penidioxolane C–D (45–46) , Sclerazaphilone A–I (47–55) , Sclerotioramine (56) , Sclerotiorin (57) , Sclerotiorin A–E (58–62) , and Sclerketide B-C (63–64) (Figures –). According to Jiang et al meroterpenoids are a family of secondary metabolites that are frequently discovered in plants, marine creatures, and fungus .…”

“…These compounds, sourced from a fungus known for producing azaphilones, hold promise for various biological applications, including the food industry . However, substances like 5-bromoisorotiorin (6), penicilazaphilones H (44) , and 5-bromosclerotiorin (7) showed limited antimicrobial activity against Staphylococcus aureus ATCC 25923 ,, (Table ).…”

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

“…All three azaphilones are active toward Staphylococcus aureus. 71 Fermentation of the mangrove-derived fungus Penicillium janthinellum HK1-6 in the presence of NaBr affords the new aryl bromide 168. 72 A strain of the fungus Penicillium copticola, associated with a Xestospongia testudinaria sponge collected in China, has delivered eight novel chlorinated copteremophilanes C−J (169−176).…”

New Azaphilones from the Marine-Derived Fungus Penicillium sclerotiorum E23Y-1A with Their Anti-Inflammatory and Antitumor Activities

“…Azaphilones, a class of structurally diverse fungal metabolites mainly from Penicillium fungi, and defined as polyketides possessing a highly oxygenated pyranoquinone bicyclic core and a quaternary carbon center, have been found to exhibit various biological properties, such as antibacterial, antifungal, cytotoxic, anti-inflammatory, and enzyme inhibitory activities [ 13 ]. In our continuing interest in finding new compounds with potential bioactivities [ 14 , 15 ], a chemical investigation of the fungus Penicillium sclerotiorum E23Y-1A derived from the marine sponge Holoxea sp. was performed to yield a further nine new azaphilones, including penicilazaphilones I–N ( 1 , 2 and 6 – 9 ), epi -geumsanol D ( 3 ), and penidioxolanes C ( 4 ) and D ( 5 ) ( Figure 1 ).…”