In this overview, naturally occurring resorcylic lactones biosynthetically derived from alternariol and almost exclusively produced by fungi, are discussed with view on their isolation, structure, biological activities, biosynthesis, and total syntheses. This class of compounds consists until now of 127 naturally occurring compounds, with very divers structural motifs. Although only a handful of these toxins (i.e., alternariol and its 9--methyl ether, altenusin, dehydroaltenusin, altertenuol, and altenuene) were frequently found and isolated as fungal contaminants in food and feed and have been investigated in significant detail, further metabolites, which were much more rarely found as natural products, similarly show interesting biological activities.
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http://dx.doi.org/10.3762/bjoc.20.187 | DOI Listing |
Nat Prod Res
January 2025
Haikou Key Laboratory for Research and Utilization of Tropical Natural Products & National Key Laboratory for Tropical Crop Breeding, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, China.
A new 12-membered resorcylic acid lactone, cochliomycin H (), and one known resorcylic acid lactone, -demethylated-zeaenol (), were isolated from sponge-derived fungus sp. ZYX-Z-4. The structure of was elucidated by 1D and 2D NMR spectroscopic as well as HR-ESI-MS analysis.
View Article and Find Full Text PDFRSC Adv
December 2024
Guangxi Key Laboratory of Marine Drugs, University Engineering Research Center of High-efficient Utilization of Marine Traditional Chinese Medicine Resources, Guangxi Institute of Marine Drugs, Guangxi University of Chinese Medicine Nanning 530200 China
Four novel resorcylic acid lactones (RALs), curvulomycins A-D (1-4), and six known congeners were isolated from the Beibu Gulf coral-derived fungus GXIMD 02512. Their structures including absolute configurations were established by extensive spectroscopic analyses along with experimental and calculated ECD spectra. Structurally, compound 3 harbors a unique γ-pyrone moiety rarely found in the natural RAL family.
View Article and Find Full Text PDFMar Drugs
September 2024
Syngenta Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK.
The incidence of infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti- drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5' and C-6', exhibits a wide range of antimicrobial, antimalarial, and antifouling activities.
View Article and Find Full Text PDFToxins (Basel)
September 2024
London Research and Development Center, Agriculture and Agri-Food Canada, London, ON N5V 4T3, Canada.
Zearalenone and radicicol are resorcylic acid lactones produced by numerous plant pathogenic fungi. Zearalenone is a non-steroidal estrogen mimic that can cause serious reproductive issues in livestock that consume contaminated feed. Radicicol is a potent inhibitor of the molecular chaperone Hsp90, which, in plants, has an important role in coordinating the host's immune response during infection.
View Article and Find Full Text PDFJ Org Chem
September 2024
Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, 980-8577 Aoba-ku, Sendai, Japan.
The total synthesis of the resorcylic acid lactones (-)-zearalenone and (-)-zearalanone is described. Our synthetic strategy relies on Ni-, Zr-, and Cr-mediated intramolecular reductive ketone coupling to create 14-membered macrolactones. Notably, the use of CrCl in addition to Ni/Zr-mediated reductive ketone coupling conditions was key for the success of the macrocyclization.
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