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A novel azaphilone dimer, humilone A (), along with its related monomer, humilone B (), was isolated from cultures of the marine-derived fungus sp. HK1-8 using a molecular networking-guided discovery approach. Further investigation of the molecular family of azaphilone dimers led to the putative identification of four analogues, humilones C-F (-), based on systematic analysis of their characteristic MS/MS fragmentation patterns. Detailed fragmentation studies of the dimers revealed that the predominant cleavage fragments originated from C-C bond scission at the dimeric methylene bridge. Compound displayed antifungal activity against .
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http://dx.doi.org/10.1021/acs.jnatprod.5c00531 | DOI Listing |
J Nat Prod
June 2025
Key Laboratory of Marine Drugs, the Ministry of Education of China, Institute of Evolution & Marine Biodiversity, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
A novel azaphilone dimer, humilone A (), along with its related monomer, humilone B (), was isolated from cultures of the marine-derived fungus sp. HK1-8 using a molecular networking-guided discovery approach. Further investigation of the molecular family of azaphilone dimers led to the putative identification of four analogues, humilones C-F (-), based on systematic analysis of their characteristic MS/MS fragmentation patterns.
View Article and Find Full Text PDFChem Biodivers
August 2025
State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Bioactive Natural Product Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, P. R. China.
Five novel dimeric polyketides, citrifuran E-I (1-5), were isolated from the fungus Aspergillus sp. AWG 1-15. These polyketides were rare heterodimers of azaphilone and furanone derivatives.
View Article and Find Full Text PDFJ Am Chem Soc
April 2025
Department of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
Cochliodone A, a dimeric azaphilone-type compound, is the major product and one of many natural products produced by , a filamentous fungus. Cochliodone A exerts antimalarial and antimycobacterial activities in addition to being cytotoxic against KB, BC1, and NCI-H187 human cancer cell lines. The potential of cochliodone A and its analogues as effective therapeutics against cancer, tuberculosis, and malaria, together with its complex dimeric chemical structure, are reasons enough for continued investigation.
View Article and Find Full Text PDFMar Drugs
May 2024
Institute for Molecular Bioscience, The University of Queensland, Brisbane, QLD 4072, Australia.
Subjecting the Australian marine-derived fungus CMB-M0339 to cultivation profiling using an innovative miniaturized 24-well plate format (MATRIX) enabled access to new examples of the rare class of 2,6-diketopiperazines, noonazines A-C (-), along with the known analogue coelomycin (), as well as a new azaphilone, noonaphilone A (). Structures were assigned to - on the basis of a detailed spectroscopic analysis, and in the case of -, an X-ray crystallographic analysis. Plausible biosynthetic pathways are proposed for -, involving oxidative Schiff base coupling/dimerization of a putative Phe precursor.
View Article and Find Full Text PDFMar Drugs
March 2023
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal.
An undescribed hybrid phenalenone dimer, talaropinophilone (), an unreported azaphilone, 7--pinazaphilone B (), an unreported phthalide dimer, talaropinophilide (), and an undescribed 9,15-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one () were isolated together with the previously reported bacillisporins A () and B (), an azaphilone derivative, Sch 1385568 (), 1-deoxyrubralactone (), acetylquestinol (), piniterpenoid D () and 3,5-dihydroxy-4-methylphthalaldehydic acid () from the ethyl acetate extract of the culture of a marine sponge-derived fungus, KUFA 1767. The structures of the undescribed compounds were elucidated by 1D and 2D NMR as well as high-resolution mass spectral analyses. The absolute configuration of C-9' of and was revised to be 9' using the coupling constant value between C-8' and C-9' and was confirmed by ROESY correlations in the case of .
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