Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria
Open Access
- 20 January 2021
- journal article
- research article
- Published by MDPI AG in Marine Drugs
- Vol. 19 (2), 46
- https://doi.org/10.3390/md19020046
Abstract
The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19–22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B–D (23–25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2′/C-3′ and C-4′/C-5′ were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4′/C-5′ and C-8′/C-9′ were suggested to be necessary for the observed antibacterial activity.Keywords
Funding Information
- Seventh Framework Programme (Grant Agreement No 312184)
This publication has 36 references indexed in Scilit:
- Kocurin, the True Structure of PM181104, an Anti-Methicillin-Resistant Staphylococcus aureus (MRSA) Thiazolyl Peptide from the Marine-Derived Bacterium Kocuria palustrisMarine Drugs, 2013
- LL-Z1272α epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciaeThe Journal of Antibiotics, 2009
- Anti-inflammatory Sesquiterpenoids from a Sponge-Derived Fungus Acremonium sp.Journal of Natural Products, 2009
- Bioactive Metabolites from the Fungus Nectria galligena, the Main Apple Canker Agent in ChileJournal of Agricultural and Food Chemistry, 2005
- A Simple Statistical Parameter for Use in Evaluation and Validation of High Throughput Screening AssaysSLAS Discovery, 1999
- A Novel Testosterone 5.ALPHA.-Reductase Inhibitor, 8',9'-Dehydroascochlorin Produced by Verticillium sp. FO-2787.CHEMICAL & PHARMACEUTICAL BULLETIN, 1994
- Studies on the constituents of Polyporus dispansus and P. confluens.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- Alteration of cholesterol metabolism and hypocholesterolemic properties of 4-O-methylascochlorin in controlled reverse-phase feeding rats.Agricultural and Biological Chemistry, 1982
- ISOLATION AND STRUCTURE OF ASCOFURANONE AND ASCOFRANOL, ANTIBIOTICS WITH HYPOLIPIDEMIC ACTIVITYThe Journal of Antibiotics, 1973
- Metabolites of Nectria coccineaJournal of the Chemical Society, Perkin Transactions 1, 1972