Covering up to the end of August 2013. Phenalenones are members of a unique class of natural polyketides exhibiting diverse biological potential. This is a comprehensive review of 72 phenalenones with diverse structural features originating from fungal sources. Their bioactive potential and structure elucidation are discussed along with a review of their biosynthetic pathways and the taxonomical relationship between the fungi producing these natural products.
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Phenalenones and Polyesters from and Structure Revision of Talaromycesone A.
J Nat Prod
December 2024
Department of Applied Biosciences, Macquarie University, Sydney, New South Wales 2109, Australia.
Investigation of the secondary metabolites of the filamentous fungus led to the isolation of two new phenalenone dimers, talarohemiketal A () and talaroazasone A (), and one new macrolide polyester, talaromacrolactone A (), along with the reported oxyphenalenone dimers talaromycesone A (), bacillisporin A (), bacillisporin B (), bacillisporin C (), -bacillisporin F (), and bacillisporin J (), the phenalenone monomer funalenone (), the polyesters 15G256α () and 15G256ν (), and 6-hydroxymellein (). Detailed analysis of 2D NMR correlations, supported by TDDFT calculations, led to the structural revision of talaromycesone A as from previously reported structure . In addition, the previously misassigned NMR spectra of compound have been corrected.
View Article and Find Full Text PDFTalauromides A-G, Nitrogen-Containing Heptacyclic Oligophenalenone Dimers from the Soil Fungus BMC-16.
J Nat Prod
October 2024
School of Pharmacy, Bengbu Medical University, 2600 Donghai Road, Bengbu 233030, People's Republic of China.
Seven new nitrogen-containing heptacyclic oligophenalenone dimers, talauromides A-G (-), together with known compounds bacillisporins A and B ( and ), talaromycesones C and B ( and ), duclauxin () and lamellicolic anhydride (), were isolated from the soil derived-fungus BMC-16. Their chemical structures were determined based on spectroscopic analysis data. The absolute configurations were elucidated by chemical approaches and the comparison of CD spectra with related compounds.
View Article and Find Full Text PDFFinal piece to the Fusarium pigmentation puzzle - Unraveling of the phenalenone biosynthetic pathway responsible for perithecial pigmentation in the Fusarium solani species complex.
Fungal Genet Biol
September 2024
Department of Chemistry and Bioscience, Aalborg University, Niels Bohrs Vej 8A, 6700 Esbjerg, Denmark. Electronic address:
The Fusarium solani species complex (FSSC) is comprised of important pathogens of plants and humans. A distinctive feature of FSSC species is perithecial pigmentation. While the dark perithecial pigments of other Fusarium species are derived from fusarubins synthesized by polyketide synthase 3 (PKS3), the perithecial pigments of FSSC are derived from an unknown metabolite synthesized by PKS35.
View Article and Find Full Text PDFAdvancing Natural Product Discovery: A Structure-Oriented Fractions Screening Platform for Compound Annotation and Isolation.
Anal Chem
April 2024
Ocean College, Zhejiang University, Zhoushan 321000, China.
Natural product discovery is hindered by the lack of tools that integrate untargeted nuclear magnetic resonance and mass spectrometry data on a library scale. This article describes the first application of the innovative NMR/MS-based machine learning tool, the "Structure-Oriented Fractions Screening Platform (SFSP)", enabling functional-group-guided fractionation and accelerating the discovery and characterization of undescribed natural products. The concept was applied to the extract of a marine fungus known to be a prolific producer of diverse natural products.
View Article and Find Full Text PDFent-Herqueidiketal and epi-Peniciherqueinone Isolated from a Mushroom Derived Fungus Penicillium herquei YNJ-35.
Chem Biodivers
September 2023
State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, 100850, Beijing, China.
A new polyaromatic metabolite, ent-herqueidiketal (1), and a new phenalenone derivative, epi-peniciherqueinone (2), along with twelve known compounds 3-14, were isolated from the fungus Penicillium herquei YNJ-35, a symbiotic fungus of Pulveroboletus brunneopunctatus collected from Nangunhe Nature Reserve, Yunnan Province, China. The structures of 1-14 and the absolute configurations of 1 and 2 were determined by their spectroscopic data or by their single-crystal X-ray diffraction analysis or optical rotation values. Compound 1 showed strong antibacterial activity against Staphylococcus aureus (ATCC 29213) with minimum inhibitory concentration (MIC) of 8 μg/mL.
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