A novel aromatic compound from the fungus Synnemellisia sp. FKR-0921.
Journal
The Journal of antibiotics
ISSN: 1881-1469
Titre abrégé: J Antibiot (Tokyo)
Pays: England
ID NLM: 0151115
Informations de publication
Date de publication:
Dec 2023
Dec 2023
Historique:
received:
14
05
2023
accepted:
11
09
2023
revised:
15
08
2023
medline:
28
11
2023
pubmed:
28
9
2023
entrez:
27
9
2023
Statut:
ppublish
Résumé
The filamentous fungus Synnemellisia sp. strain FKR-0921 was obtained from soil collected on Kume Island, Okinawa. The MeOH extract of FKR-0921 cultured on a solid rice medium yielded a new aromatic compound, synnemellisitriol A (1). The structure, including the absolute configuration, was elucidated by spectroscopic analysis (FT-IR, NMR, and HR-ESI-MS), and the absolute configuration at C-9 of 1 was determined using the modified Mosher's method. Additionally, 1 was evaluated for its biological activities, including metallo-β-lactamase inhibitory activity, type III secretion system inhibitory activity, antimicrobial activity, antimalarial activity, and cytotoxicity.
Identifiants
pubmed: 37758818
doi: 10.1038/s41429-023-00657-4
pii: 10.1038/s41429-023-00657-4
doi:
Substances chimiques
Phenols
0
beta-Lactamase Inhibitors
0
Anti-Infective Agents
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
706-710Informations de copyright
© 2023. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.
Références
Rosa LH, et al. Fungi in Antarctica: Diversity, ecology, effects of climate change, and bioprospection for bioactive compounds. In: Fungi of Antarctica. (Springer Nature, Switzerland, 2019), 1–17.
Wiese J, Imhoff JF. Marine bacteria and fungi as promising source for new antibiotics. Drug Dev Res. 2019;80:24–27.
doi: 10.1002/ddr.21482
pubmed: 30370576
Amirzakariya BZ, Shakeri A. Bioactive terpenoids derived from plant endophytic fungi: An updated review (2011–2020). Phytochemistry. 2022;197:113130.
doi: 10.1016/j.phytochem.2022.113130
pubmed: 35183568
Cadamuro RD, et al. Bioactive compounds from mangrove endophytic fungus and their uses for microorganism control. J Fungi. 2021;7:455–473.
doi: 10.3390/jof7060455
Lobanovska M, Pilla G. Penicillin’s discovery and antibiotic resistance: Lessons for the future? Yale J Biol Med. 2017;90:135–145.
pubmed: 28356901
pmcid: 5369031
Kozłowska E, et al. New 6,19‑oxidoandrostan derivatives obtained by biotransformation in environmental filamentous fungi cultures. Microb Cell Fact. 2020;19:37–51.
doi: 10.1186/s12934-020-01303-6
pubmed: 32066453
pmcid: 7026961
Tian Y, Li Y. A review on bioactive compounds from marine-derived Chaetomium species. Biotechnol Adv. 2022;32:541–550.
Krawczyk-Łebek A, Dymarska M, Janeczko T, Kostrzewa-Susłow E. Glycosylation of methylflavonoids in the cultures of entomopathogenic filamentous fungi as a tool for obtaining new biologically active compounds. Int J Mol Sci. 2022;23:5558.
doi: 10.3390/ijms23105558
pubmed: 35628367
pmcid: 9146141
Koike R, et al. Shikinefragalides A-D, new tricyclic macrolides produced by Stachybotryaceae sp. FKI-9632. J Antibiot. 2022;75:199–206.
doi: 10.1038/s41429-022-00512-y
Sakai K, et al. Sesquicillin F, a new insecticidal meroterpenoid produced by Mariannaea macrochlamydospora FKI-4735. J Antibiot. 2021;74:817–820.
doi: 10.1038/s41429-021-00456-9
Sakai K, et al. Aldsulfin, a novel unusual anti-mannheimiosis epithiodiketopiperazine antibiotic produced by Lasiodiplodia pseudotheobromae FKI-4499. J Antibiot. 2021;74:363–369.
doi: 10.1038/s41429-021-00411-8
Nuryadi H, Suda S. Revealing the species diversity of Neolyngbya (Cyanobacteria, Oscillatoriales) from subtropical coastal regions of Okinawa, Japan, with descriptions of Neolyngbya intertidalis sp. nov. and Neolyngbya latusa sp. nov. Phycol Res. 2022;70:69–80.
doi: 10.1111/pre.12482
Nonaka K, Kaifuchi S, Ōmura S, Masuma R. Five new Simplicillium species (Cordycipitaceae) from soils in Tokyo, Japan. Mycoscience. 2013;54:42–53.
doi: 10.1016/j.myc.2012.07.002
Altschul SF, et al. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 1997;25:3389–3402.
doi: 10.1093/nar/25.17.3389
pubmed: 9254694
pmcid: 146917
Tan YP, et al. Nomenclatural novelties. Index Fungorum. 2021;503:1–8.
Watanabe Y, et al. Koshidacins A and B, antiplasmodial cyclic tetrapeptides from the Okinawan fungus Pochonia boninensis FKR-0564. J Nat Prod. 2022;85:2641–2649.
doi: 10.1021/acs.jnatprod.2c00719
pubmed: 36282784
Ikeda A, et al. A new selective inhibitor for IMP-1 metallo-β-lactamase, 3Z,5E-octa-3,5-diene-1,3,4- tricarboxylic acid-3,4-anhydride. Bioorg Med Chem. 2023;78:117109.
doi: 10.1016/j.bmc.2022.117109
pubmed: 36603397
Kimura K, et al. A small-molecule inhibitor of the bacterial type III secretion system protects against in vivo infection with Citrobacter rodentium. J Antibiot. 2011;64:197–203.
doi: 10.1038/ja.2010.155
Lewis JS II. Performance standards for antimicrobial susceptibility testing, 32nd ed. Clinical and Laboratory Standards Institute, USA, 2022.
Otoguro K, et al. In vitro antimalarial activities of the microbial metabolites. J Antibiot. 2003;56:322–324.
doi: 10.7164/antibiotics.56.322
Otoguro K, et al. Potent antimalarial activities of polyether antibiotic, X-206. J Antibiot. 2001;54:658–663.
doi: 10.7164/antibiotics.54.658
Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc. 1973;95:512–519.
doi: 10.1021/ja00783a034
Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc. 1991;113:4092–4096.
doi: 10.1021/ja00011a006
Avalos J, Limón MC. Fungal secondary metabolism. Encyclopedia. 2022;2:1–13.
doi: 10.3390/encyclopedia2010001
Caesar LK, Kelleher NL, Keller NP. In the fungus where it happens: History and future propelling Aspergillus nidulans as the archetype of natural products research. Fungal Genet Biol. 2020;144:103477.
doi: 10.1016/j.fgb.2020.103477
pubmed: 33035657
pmcid: 7726033