Antimicrobial polyketides from Magellan Seamount-derived fungus Talaromyces scorteus AS-242.
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:
17
07
2023
accepted:
28
09
2023
revised:
08
09
2023
medline:
28
11
2023
pubmed:
18
10
2023
entrez:
17
10
2023
Statut:
ppublish
Résumé
Two new nonadride derivatives, namely, talarodrides G and H (1 and 2), and one new depsidone derivative, botryorhodine K (3), together with a known nonadride analogue (4), were characterized from the Magellan Seamount-derived fungus Talaromyces scorteus AS-242. Their structures were established by detailed interpretation of NMR spectroscopic and mass spectrometry data analysis. X-ray crystallographic analysis of compounds 1 and 3 confirmed their structures and absolute configurations, representing the first characterized crystal structure of a nonadride-type polyketide. The isolated compounds exhibited potent antimicrobial activities against the pathogenic bacterium MRSA and V. parahaemolyticus and pathogenic fungi C. gloeosporioides, F. oxysporum, and F. proliferatum, with MIC values ranging from 1 to 64 μg ml
Identifiants
pubmed: 37848580
doi: 10.1038/s41429-023-00664-5
pii: 10.1038/s41429-023-00664-5
doi:
Substances chimiques
Polyketides
0
Anti-Infective Agents
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
699-705Informations de copyright
© 2023. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.
Références
Staunton J, Weissman KJ. Polyketide biosynthesis: a millennium review. Nat. Prod. Rep. 2001;18:380–416.
doi: 10.1039/a909079g
pubmed: 11548049
Weng WY, Li RD, Zhang YX, Pan XF, Jiang SC, et al. Polyketides isolated from an endophyte Penicillium oxalicum 2021CDF-3 inhibit pancreatic tumor growth. Front. Microbiol. 2022;13:1–9.
doi: 10.3389/fmicb.2022.1033823
Liu T, Zhang SY, Li ZL, Wang Y, Chen ZX, et al. A new polyketide, penicillolide from the marinederived fungus Penicillium sacculum. Nat. Prod. Res. 2016;30:1025–9.
doi: 10.1080/14786419.2015.1101693
pubmed: 26499896
Mahmoud MM, Abdel-Razek AS, Hamed A, Soliman HSM, Ponomareva LV, et al. RF-3192C and other polyketides from the marine endophytic Aspergillus niger ASSB4: structure assignment and bioactivity investigation. Med. Chem. Res. 2021;30:647–54.
doi: 10.1007/s00044-020-02658-6
Lai CR, Chen JY, Liu J, Tian DM, Lan DH, et al. New polyketides from a hydrothermal vent sediment fungus Trichoderma sp. JWM29-10-1 and their antimicrobial effects. Mar. Drugs. 2022;20:720.
doi: 10.3390/md20110720
pubmed: 36421998
pmcid: 9697660
Sun Y, Tian L, Huang J, Ma HY, Zheng Z, et al. Trichodermatides A−D, Novel polyketides from the marine-derived fungus Trichoderma reesei. Org. Lett. 2008;10:393–6.
doi: 10.1021/ol702674f
pubmed: 18163636
Wei H, Itoh T, Kotoku N, Kobayashi M. Shimalactiones neuritogenic polyketides from a marine-derived fungus Emericella variecolor GF10. Heterocycles. 2006;68:111–23.
doi: 10.3987/COM-05-10589
Suzuki T, Ariefta NR, Koseki T, Furuno H, Kwon E, et al. New polyketides, paralactonic acids A–E produced by Paraconiothyrium sp. SW-B-1, an endophytic fungus associated with a seaweed, Chondrus ocellatus Holmes. Fitoterapia. 2019;132:75–81.
doi: 10.1016/j.fitote.2018.11.017
pubmed: 30496810
Lei H, Lei J, Zhou XF, Hu M, Niu H, et al. Cytotoxic polyketides from the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09. Molecules. 2019;24:2655.
doi: 10.3390/molecules24142655
pubmed: 31336683
pmcid: 6680542
Mohamed IE, Gross H, Pontius A, Kehraus S, Krick A, et al. Epoxyphomalin A and B, prenylated polyketides with potent cytotoxicity from the marine-derived fungus Phoma sp. Org. Lett. 2009;11:5014–7.
doi: 10.1021/ol901996g
pubmed: 19813715
Niu SW, Tang XX, Fan ZW, Xia JM, Xie CL, Yang XW, et al. Polyketides from the marine-derived fungus Fusarium solani H918. Mar. Drugs. 2019;17:125.
doi: 10.3390/md17020125
pubmed: 30791608
pmcid: 6410219
Liu YF, Zhang YH, Shao CL, Cao F, Wang CY. Microketides A and B, polyketides from a gorgonian-derived Microsphaeropsis sp. Fungus. J. Nat. Prod. 2020;83:1300–4.
doi: 10.1021/acs.jnatprod.0c00144
pubmed: 32243151
Gou XS, Tian DM, Wei JH, Ma YH, Zhang YX, et al. New drimane sesquiterpenes and polyketides from marine-derived fungus Penicillium sp. TW58-16 and their anti-inflammatory and α-Glucosidase inhibitory effect. Mar. Drugs. 2021;19:416.
doi: 10.3390/md19080416
pubmed: 34436259
pmcid: 8398500
Zhang YH, Du HF, Cao WB, Li W, Cao F, Wang CY. Anti-inflammatory polyketides from the marine-derived fungus Eutypella scoparia. Mar. Drugs. 2022;20:486.
doi: 10.3390/md20080486
pubmed: 36005490
pmcid: 9410037
Wang JF, Zhao BB, Yi YT, Zhang W, Wu X, Zhang LR, et al. Mycoepoxydiene, a fungal polyketide inhibits MCF-7 cells through simultaneously targeting p53 and NF-kB pathways. Biochem. Pharmacol. 2012;84:891–899.
doi: 10.1016/j.bcp.2012.07.004
pubmed: 22796259
Zhang DH, Li XG, Kang JS, Choi HD, Jung JH, Son BW. Redoxcitrinin, a biogenetic precursor of citrinin from marine isolate of Fungus Penicillium sp. J. Microbiol. Biotechnol. 2007;17:865–867.
pubmed: 18051311
Bao J, Sun YL, Zhang XY, Han Z, Gao HC, He F, et al. Antifouling and antibacterial polyketides from marine gorgonian coral-associated fungus Penicillium sp. SCSGAF 0023. J. Antibiot. 2013;66:219–23.
doi: 10.1038/ja.2012.110
Niu SW, Liu QM, Xia JM, Xie CL, Luo ZH, et al. Polyketides from the deep-sea-derived fungus Graphostroma sp. MCCC 3A00421 showed potent antifood allergic activities. J. Agric. Food Chem. 2018;66:1369–76.
doi: 10.1021/acs.jafc.7b04383
pubmed: 29355320
Meng LH, Li XM, Zhang FZ, Wang YN, Wang BG, Talascortenes A−G. Highly oxygenated diterpenoid acids from the sea-anemone-derived endozoic fungus Talaromyces scorteus AS-242. J. Nat. Prod. 2020;83:2528–36.
doi: 10.1021/acs.jnatprod.0c00628
pubmed: 32813522
Li HL, Li XM, Li X, Wang CY, Liu H, et al. Antioxidant hydroanthraquinones from the marine algal-derived endophytic fungus Talaromyces islandicus EN-501. J. Nat. Prod. 2017;80:162–68.
doi: 10.1021/acs.jnatprod.6b00797
pubmed: 27992187
Zhang FZ, Li XM, Yang SQ, Meng LH, Wang BG. Thiocladospolides A−D, 12-Membered macrolides from the mangrove-derived endophytic fungus Cladosporium cladosporioides MA-299 and Structure Revision of Pandangolide 3. J. Nat. Prod. 2019;82:1535–41.
doi: 10.1021/acs.jnatprod.8b01091
pubmed: 31038952
Wang Y, Li XM, Yang SQ, Zhang FZ, Wang BG, Li HL, et al. Sesquiterpene and sorbicillinoid glycosides from the endophytic Fungus Trichoderma longibrachiatum EN-586 derived from the marine red Alga Laurencia obtusa. Mar. Drugs. 2022;20:177.
doi: 10.3390/md20030177
pubmed: 35323476
pmcid: 8949086
Li YH, Yang SQ, Li XM, Li X, Wang BG, Li HL. Cyclopiumolides A and B, unusual 13-membered macrolides from the deep sea-sourced fungus Penicillium cyclopium SD-413 with antiproliferative activities. Bioorg. Chem. 2022;128:106104.
doi: 10.1016/j.bioorg.2022.106104
pubmed: 36058117
Zhao Y, Sun CX, Huang LY, Zhang X, Zhang G,J, et al. Talarodrides A−F, nonadrides from the antarctic sponge-derived Fungus Talaromyces sp. HDN1820200. J. Nat. Prod. 2021;84:3011–3019.
doi: 10.1021/acs.jnatprod.1c00203
pubmed: 34842422
Spencer P, Agnelli F, Sulikowski GA. Investigations into the production and interconversion of phomoidrides A−D. Org. Lett. 2001;3:1443–1445.
doi: 10.1021/ol015707k
pubmed: 11388837
Grimblat N, Zanardi MM, Sarotti AM. Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts. J. Org. Chem. 2015;80:12526–34.
doi: 10.1021/acs.joc.5b02396
pubmed: 26580165
Abdou R, Scherlach K, Dahse HM, Sattler I, Hertweck C. Botryorhodines A–D, antifungal and cytotoxic depsidones from Botryosphaeria rhodina, an endophyte of the medicinal plant Bidens pilosa. Phytochemistry. 2010;71:110–16.
doi: 10.1016/j.phytochem.2009.09.024
pubmed: 19913264
Crystallographic data of compounds 1 and 3 have been deposited in the Cambridge Crystallographic Data Centre as CCDC 2162966 (for 1), and CCDC 2162965 (for 3). These data can be obtained free of charge via https://www.ccdc.cam.ac.uk/MyStructures/ (or from the CCDC, 12 Union Road, Cambridge CB21EZ, U.K.; fax: + 44-1223-336-033; email: hello@ccdc.cam.ac.uk).
Sheldrick GM, SADABS, Software for Empirical Absorption Correction; University of Gottingen: Gottingen, Germany, 1996.
Sheldrick GM, SHELXL, Structure Determination Software Programs; Bruker Analytical X-ray System Inc. Madison, WI, USA, 1997.
Sheldrick GM, SHELXL, Program for the Refinement of Crystal Structures; University of Gottingen: Gottingen, Germany, 2014.
Parsons S, Flack HD, Wagner T. Acta. Crystallogr B. Use of intensity quotients and differences in absolute structure refinement. Struct. Sci. Cryst. Eng. Mater. 2013;B69:249–59.
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, et al. Gaussian 09, Revision D.01. Gaussian, Inc. Wallingford, UK, 2013.
Pierce CG, Uppuluri P, Tristan AR, Wormley FL, Mowat E, Ramage G, et al. A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing. Nat. Protoc. 2008;3:1494–1500.
doi: 10.1038/nprot.2008.141
pubmed: 18772877
pmcid: 2741160