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Abstract
Six new β-resorcylic acid derivatives (1–5 and 7) were isolated from a halophyte-associated fungus, Colletotrichum gloeosporioides JS0419, together with four previously reported β-resorcylic acid lactones (RALs). The relative and absolute stereochemistry of 1 was completely established by a combination of spectroscopic data and chemical reactions. The structures of the isolated compounds were elucidated by analysis of HRMS and NMR data. Notably, compounds 1–3 had a β-resorcylic acid harboring a long unesterified aliphatic side chain, whereas the long aliphatic chains were esterified to form macrolactones in 4–9. Among the isolated compounds, monocillin I and radicicol showed potent antifungal activities against Cryptococcus neoformans, comparable to clinically available antifungal agents and radicicol showed weak antifungal activity against Candida albicans. These findings provide insight into the chemical diversity of fungal RAL-type compounds and their pharmacological potential.
Highlights
A variety of bioactive metabolites have been reported from plant-associated microorganisms [1]
Values (12.5 μM) almost equivalent to those of amphotericin B (AMB) and fluconazole (FCZ) (12.5 μM), which are clinically used for the treatment of systemic cryptococcosis
While most resorcylic acid lactones (RALs) reported to date feature a 14-membered macrocyclic ring fused to β-resorcylic acid, compounds 1–3 harbored β-resorcylic acid with a long unesterified aliphatic side chain and compound 4 had a
Summary
A variety of bioactive metabolites have been reported from plant-associated microorganisms [1]. RAL-type compounds, such as LL-Z1640-2, hypothemycin, monocillins (I–V), zeaenol, aigialomycins (A–E), pochonins (A–P), paecilomycins (A–F), and cochliomycins, have been subsequently reported to date [5–14]. All of these RAL-type compounds exhibit diverse biological activities, such as antifungal, cytotoxic, antimalarial, antiviral, antiparasitic,. Diverse biological activities, as antifungal, cytotoxic,compounds antimalarial, antiviral, antiparaAs part of our efforts tosuch discover new bioactive from halophyte-associsitic, nematicidal, estrogenic, protein tyrosine kinase, and ATPase inhibition, resulting ated fungi, we investigated the chemical profiles of fungal extracts using liquidinchromasignificantly increasing attention in the field of natural product chemistry [10,11,15–20]. AfterJS0419, fermentation andthe subsequent purification, analysis, because it produces a varietyinofC.secondary metabolites with unique fied further two distinct classes of new compounds gloeosporioides.
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