• This record comes from PubMed

Dactylfungins and Tetralones: Bioactive Metabolites from a Nematode-Associated Laburnicola nematophila

. 2024 Jul 26 ; 87 (7) : 1860-1871. [epub] 20240716

Language English Country United States Media print-electronic

Document type Journal Article, Research Support, Non-U.S. Gov't, Research Support, N.I.H., Extramural

Grant support
P40 OD010440 NIH HHS - United States

A chemical investigation of Laburnicola nematophila, isolated from cysts of the plant parasitic nematode Heterodera filipjevi, affored three dactylfungin derivatives (1-3) and three tetralone congeners (4-6). Dactylfungin C (1), laburnicolin (4), and laburnicolenone (5) are previously undescribed natural products. Chemical structures of the isolated compounds were determined based on 1D and 2D NMR spectroscopic analyses together with HR-ESI-MS spectrometry and comparison with data reported in the literature. The relative configurations of compounds 1, 2, and 4-6 were determined based on their ROESY data and analysis of their coupling constants (J values). The absolute configurations of 4-6 were determined through the comparison of their measured and calculated TDDFT-ECD spectra. Compounds 1-3 were active against azole-resistant Aspergillus fumigatus.

See more in PubMed

Atanasov A. G.; Zotchev S. B.; Dirsch V. M.; Orhan I. E.; Banach M.; Rollinger J. M.; Barreca D.; Weckwerth W.; Bauer R.; Bayer E. A.; et al. Nat. Rev. Drug Discovery 2021, 20, 200–216. 10.1038/s41573-020-00114-z. PubMed DOI PMC

Miethke M.; Pieroni M.; Weber T.; Brönstrup M.; Hammann P.; Halby L.; Arimondo P. B.; Glaser P.; Aigle B.; Bode H. B.; et al. Nat. Rev. Chem. 2021, 5, 726–749. 10.1038/s41570-021-00313-1. PubMed DOI PMC

Mapook A.; Hyde K. D.; Hassan K.; Kemkuignou B. M.; Čmoková A.; Surup F.; Kuhnert E.; Paomephan P.; Cheng T.; de Hoog S.; et al. Fungal Divers. 2022, 116, 547–614. 10.1007/s13225-022-00510-3. PubMed DOI PMC

Hyde K. D.; Al-Hatmi A. M. S.; Andersen B.; Boekhout T.; Buzina W.; Dawson T. L.; Eastwood D. C.; Jones E. B. G.; de Hoog S.; Kang Y.; et al. Fungal Divers. 2018, 93, 161–194. 10.1007/s13225-018-0413-9. DOI

WHO Releases First-Ever List of Health-Threatening Fungi; 2022; Vol. 43; ISBN 9789240060241. PubMed PMC

Kwon-Chung K. J.; Fraser J. A.; Doering T. L.; Wang Z. A.; Janbon G.; Idnurm A.; Bahn Y.-S. Cold Spring Harb. Perspect. Med. 2018, 4, a019760–a019760. 10.1101/cshperspect.a019760. PubMed DOI PMC

Kosmidis C.; Denning D. W. Thorax 2015, 70, 270–277. 10.1136/thoraxjnl-2014-206291. PubMed DOI

Szalewski D. A.; Hinrichs V. S.; Zinniel V. K.; Barletta R. G. Can. J. Microbiol. 2018, 64, 439–453. 10.1139/cjm-2017-0749. PubMed DOI

Verweij P. E.; Lucas J. A.; Arendrup M. C.; Bowyer P.; Brinkmann A. J.; Denning D. W.; et al. Fungal Biol. Rev. 2020, 34 (4), 202–214. 10.1016/j.fbr.2020.10.003. DOI

Wanasinghe D. N.; Jones E. B. G.; Camporesi E.; Dissanayake A. J.; Kamolhan S.; Mortimer P. E.; Xu J.; Abd-Elsalam K. A.; Hyde K. D. Fungal Biol. 2016, 120, 1354–1373. 10.1016/j.funbio.2016.06.006. PubMed DOI

Zhang Y.; Crous P. W.; Schoch C. L.; Hyde K. D. Fungal Divers. 2012, 53, 1–221. 10.1007/s13225-011-0117-x. PubMed DOI PMC

Knapp D. G.; Akhmetova G. K.; Kovács G. M.; Dababat A. A.; Maier W.; Ashrafi S. Mycol. Prog. 2022, 21, 99.10.1007/s11557-022-01849-2. DOI

Ashrafi S.; Knapp D. G.; Blaudez D.; Chalot M.; Maciá-Vicente J. G.; Zagyva I.; Dababat A. A.; Maier W.; Kovács G. M. Mycologia 2018, 110, 286–299. 10.1080/00275514.2018.1448167. PubMed DOI

Ashrafi S.; Wennrich J. P.; Becker Y.; Maciá-Vicente J. G.; Brißke-Rode A.; Daub M.; Thünen T.; Dababat A. A.; Finckh M. R.; Stadler M.; et al.. IMA Fungus 2023, 14,10.1186/s43008-023-00113-w. PubMed DOI PMC

Wennrich J.-P.; Sepanian E.; Ebada S. S.; Llanos-Lopez N. A.; Ashrafi S.; Maier W.; Kurtán T.; Stadler M. Antibiotics 2023, 12, 1273.10.3390/antibiotics12081273. PubMed DOI PMC

Xaio J.-Z.; Kumazawa S.; Yoshikawa N.; Mikawa T.; Sato Y. J. Antibiot. 1993, 46, 48–55. 10.7164/antibiotics.46.48. PubMed DOI

Nagai K.; Kamigiri K.; Matsumoto H.; Kawano Y.; Yamaoka M.; Shimoi H.; Watanabe M.; Suzuki K. J. Antibiot. 2002, 55 (12), 1036–1041. 10.7164/antibiotics.55.1036. PubMed DOI

Li W.-S.; Yan R.-J.; Yu Y.; Shi Z.; Mándi A.; Shen L.; Kurtán T.; Wu J. Angew. Chem., Int. Ed. 2020, 59, 13028–13036. 10.1002/anie.202004358. PubMed DOI

Jiang Z.-P.; Sun S.-H.; Yu Y.; Mándi A.; Luo J.-Y.; Yang M.-H.; Kurtán T.; Chen W.-H.; Shen L.; Wu J. Chem. Sci. 2021, 12, 10197.10.1039/D1SC02810C. PubMed DOI PMC

Charria-Girón E.; Stchigel A. M.; Čmoková A.; Kolařík M.; Surup F.; Marin-Felix Y. J. Fungi 2023, 9, 463.10.3390/jof9040463. PubMed DOI PMC

Meingassner J. G.; Thirring K.. 2005. WO2005097771A1.

Li K.-K.; Lu Y.-J.; Song X.-H.; She Z.-G.; Wu X.-W.; An L.-K.; Ye C.-X.; Lin Y.-C. Bioorg. Med. Chem. Lett. 2010, 20, 3326–3328. 10.1016/j.bmcl.2010.04.036. PubMed DOI

Cai R.; Wu Y.; Chen S.; Cui H.; Liu Z.; Li C.; She Z. J. Nat. Prod. 2018, 81 (6), 1376–1383. 10.1021/acs.jnatprod.7b01018. PubMed DOI

Saepua S.; Kornsakulkarn J.; Somyong W.; Laksanacharoen P.; Isaka M.; Thongpanchang C. Tetrahedron 2018, 74 (8), 859–866. 10.1016/j.tet.2018.01.004. DOI

Savi D. C.; Shaaban K. A.; Mitra P.; Ponomareva L. V.; Thorson J. S.; Glienke C.; Rohr J. J. Antibiot. 2019, 72, 306–310. 10.1038/s41429-019-0154-3. PubMed DOI PMC

Padula D.; Pescitelli G. Molecules 2018, 23, 128.10.3390/molecules23010128. PubMed DOI PMC

Bakowies D.; von Lilienfeld O. A. J. Chem. Theory Comput. 2021, 17, 4872–4890. 10.1021/acs.jctc.1c00474. PubMed DOI PMC

Superchi S.; Scafato P.; Górecki M.; Pescitelli G. Curr. Med. Chem. 2018, 25, 287–320. 10.2174/0929867324666170310112009. PubMed DOI

Mándi A.; Kurtán T. Nat. Prod. Rep. 2019, 36, 889–918. 10.1039/C9NP00002J. PubMed DOI

Snatzke G.; Znatzke F.; Tõkés A. L.; Rákosi M.; Bognár R. Tetrahedron 1973, 29, 909–912. 10.1016/0040-4020(73)80037-7. DOI

Kurtán T.; Antus S.; Pescitelli G.. Electronic CD of benzene and other aromatic chromophores for determination of absolute configuration. In Comprehensive Chiroptical Spectroscopy; John Wiley & Sons Inc.: Hoboken, NJ, 2012; Vol. 2, pp 73–114.

Laurent D.; Guella G.; Mancini I.; Roquebert M. F.; Farinole F.; Pietra F. Tetrahedron 2002, 58, 9163–9167. 10.1016/S0040-4020(02)01222-X. PubMed DOI

Couche E.; Fkyerat A.; Tabacchi R. Helv. Chim. Acta 2003, 86, 210–221. 10.1002/hlca.200390014. DOI

Chen Y. L.; Tan C. H.; Tan J. J.; Qu S. J.; Jiang S. H.; Zhu D. Y. Planta Med. 2008, 74, 1826–1828. 10.1055/s-0028-1088328. PubMed DOI

Abdelwahab M. F.; Kurtán T.; Mándi A.; Müller W. E. G.; Fouad M. A.; Kamel M. S.; Liu Z.; Ebrahim W.; Daletos G.; Proksch P. Tetrahedron Lett. 2018, 59, 2647–2652. 10.1016/j.tetlet.2018.05.067. DOI

Machida K.; Matsuoka E.; Kasahara T.; Kikuchi M. Chem. Pharm. Bull. 2005, 53, 934–937. 10.1248/cpb.53.934. PubMed DOI

Liu L.; Li A. L.; Zhao M. B.; Tu P. F. Chem. Biodivers. 2007, 4, 2932–2937. 10.1002/cbdv.200790242. PubMed DOI

Fukami A.; Nakamura T.; Kim Y. P.; Shiomi K.; Hayashi M.; Nagai T.; Yamada H.; Komiyama K.; Omura S. J. Antibiot. 2000, 53, 1215–1258. 10.7164/antibiotics.53.1215. PubMed DOI

Klyne W.; Stokes W. M. J. Chem. Soc. 1954, 1954, 1979–1988. 10.1039/jr9540001979. DOI

McLean S. Can. J. Chem. 1964, 42, 191–195. 10.1139/v64-035. DOI

Tanaka K.; Hirayama K.; Yonezawa H.; Sato G.; Toriyabe A.; Kudo H.; Hashimoto A.; Matsumura M.; Harada Y.; Kurihara Y.; et al. Stud. Mycol. 2015, 82, 75–136. 10.1016/j.simyco.2015.10.002. PubMed DOI PMC

Štěpánek O.; Čmoková A.; Procházková E.; Grobárová V.; Černý J.; Slapničková M.; Zíková A.; Kolařík M.; Baszczyňski O.. ChemMedChem 2022, 17,10.1002/cmdc.202200385. PubMed DOI

Arendrup M. C.; Friberg N.; Mares M.; Kahlmeter G.; Meletiadis J.; Guinea J.; Arendrup M. C.; Meletiadis J.; Guinea J.; Friberg N.; et al. Clin. Microbiol. Infect. 2020, 26, 1464–1472. 10.1016/j.cmi.2020.06.007. PubMed DOI

Phutthacharoen K.; Toshe R.; Khalid S. J.; Llanos-López N. A.; Wennrich J.-P.; Schrey H.; Ebada S. S.; Hyde K. D.; Stadler M. Chem. Biodivers. 2024, 21, e20240038510.1002/cbdv.202400385. PubMed DOI

MacroModel; Schrödinger LLC, 2015. Available online: http://www.schrodinger.com/MacroModel (accessed 10 May 2023).

Frisch M. J.; Trucks G. W.; Schlegel H. B.; Scuseria G. E.; Robb M. A.; Cheeseman J. R.; Scalmani G.; Barone V.; Mennucci B.; Petersson G. A.; et al.Gaussian 16, Revision C.02; Gaussian Inc.: Wallingford CT, USA, 2019.

Stephens P. J.; Harada N. Chirality 2010, 22, 229–233. 10.1002/chir.20733. PubMed DOI

Varetto U.MOLEKEL, 5.4; Swiss National Supercomputing Centre: Manno, Switzerland, 2009.

Find record

Citation metrics

Loading data ...

Archiving options

Loading data ...