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The chemical investigation of the marine-derived fungus Penicillium sp. led to the isolation of three new secondary metabolites, including one isobenzofuranone (1) and two isochromenones (2 and 3), along with five known compounds (4-8). The structures of the new compounds, including their absolute configurations, were elucidated through comprehensive nuclear magnetic resonance, optical rotatory dispersion, and electronic circular dichroism spectral analyses. The antibacterial, cytotoxic, and α-glucosidase inhibitory activity of all compounds was assessed. Compounds 1 (IC₅₀ = 76.4 µM), 3 (IC₅₀ = 95.4 µM), and 4 (IC₅₀ = 88.3 µM) exhibited inhibitory effects against α-glucosidase, showing comparable activity to the positive control acarbose (IC₅₀ = 67.7 µM). Molecular docking revealed that these structurally analogous compounds exhibited similar binding modes within the active site.
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http://dx.doi.org/10.1002/cbdv.202501466 | DOI Listing |
Chem Biodivers
July 2025
College of Pharmaceutical Sciences, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei University, Baoding, China.
The chemical investigation of the marine-derived fungus Penicillium sp. led to the isolation of three new secondary metabolites, including one isobenzofuranone (1) and two isochromenones (2 and 3), along with five known compounds (4-8). The structures of the new compounds, including their absolute configurations, were elucidated through comprehensive nuclear magnetic resonance, optical rotatory dispersion, and electronic circular dichroism spectral analyses.
View Article and Find Full Text PDFMar Drugs
June 2017
Chinese Academy of Sciences (CAS) Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, CAS, Guangzhou 510301, China.
Four new isobenzofuranones, leptosphaerins J-M (-), including an unusual naturally-occurring centrosymmetric dimer skeleton (), and two new isochromenones, clearanols I-J (-), were obtained from a culture of a deep-sea sediment-derived fungus sp. SCSIO 41005, together with four known isobenzofuranones (-) and six known isochromenones (-). These structures were elucidated by extensive spectroscopic analyses, and absolute configurations were assigned on the basis of electronic circular dichroism and optical rotations data comparison.
View Article and Find Full Text PDFOrg Biomol Chem
June 2017
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende (CS), Italy.
The regiochemical outcome of the iodolactonization of 2-alkynylbenzoic acids, carried out at 100 °C in ionic liquids (ILs) as unconventional solvents and with molecular iodine as the iodine source, in the absence of external bases, was found to be strongly dependent on the nature of the IL medium. In particular, while the use of N-ethyl-N-methylmorpholinium dicyanamide (MorN(CN)) promoted the stereoselective formation of (E)-3-(iodomethylene)isobenzofuran-1(3H)-ones, through an anti-5-exo-dig cyclization route, the use of 1-ethyl-3-methylimidazolium ethyl sulfate (EmimEtSO) tended to favor the 6-endo-dig cyclization mode, with preferential or selective formation of 4-iodo-1H-isochromen-1-ones. In any case, the IL solvent could be easily recycled after extraction of the product from the reaction mixture with diethyl ether.
View Article and Find Full Text PDFPhytochemistry
August 2014
University of North Carolina at Greensboro, Department of Chemistry and Biochemistry, Greensboro, NC 27402, United States. Electronic address:
Six isochromenones (1-6), clearanols F (5) and G (6), one isobenzofuranone (7), and two tetrahydronaphthalene derivatives (8 and radinaphthalenone (9)), were isolated and identified from a culture of the fungus Paraphoma radicina, which was isolated from submerged wood in a freshwater lake. Compounds 5, 6 and 9 were previously unknown. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 5 and 6 were determined by comparison of their experimental ECD measurements with values predicted by TDDFT calculations.
View Article and Find Full Text PDFJ Nat Prod
March 2011
The United Graduate School of Agricultural Sciences, Iwate University, 18-8, Ueda 3, Morioka, 020-8550, Japan.
Two new metabolites, (R)-3,4-dihydro-4,6,8-trihydroxy-4,5-dimethyl-3-methyleneisochromen-1-one (1) and (R)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (2), were isolated along with two structurally known related compounds (3 and 4) from the culture broth of Leptosphaeria sp. KTC 727 (JCM 13076 = MAFF 239586). These structures were disclosed mainly with (1)H and (13)C NMR spectroscopic analyses.
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