DOI QR코드

DOI QR Code

Chemical Constituents of the Culture Broth of Panus rudis

  • Song, Ja-Gyeong (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University) ;
  • Ha, Lee Su (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University) ;
  • Ki, Dae-Won (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University) ;
  • Choi, Dae-Cheol (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University) ;
  • Lee, In-Kyoung (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University) ;
  • Yun, Bong-Sik (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University)
  • Received : 2021.10.01
  • Accepted : 2021.11.07
  • Published : 2021.12.31

Abstract

In our ongoing search for new secondary metabolites from fungal strains, one novel compound (1) and nine known compounds (2-10) were isolated from the EtOAc-soluble layer of the culture broth of Panus rudis. The culture broth of P. rudis was extracted in acetone and fractionated by solvent partition; column chromatography using silica gel, Sephadex LH-20, and Sephadex G-10; MPLC; and HPLC. The structures of isolated compounds were elucidated by one- and two-dimensional NMR and LC-ESI-mass measurements. One new compound, panepoxydiol (1), and nine known compounds, (E)-3-(3-hydroxy-3-methylbut-1-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol (2), isopanepoxydone (3), neopanepoxydone (4), panepoxydone (5), panepophenanthrin (6), 4-hydroxy-2,2-dimethyl-6-methoxychromane (7), 6-hydroxy-2,2-dimethyl-3-chromen (8), 2,2-dimethyl-6-methoxychroman-4-one (9), 3,4-dihydroxy-2,2-dimethyl-6-methoxychromane (10), were isolated from the culture broth of P. rudis. This is the first report of isolation of a new compound panepoxydiol (1) and nine other chemical constituents (2-5, 7-10) from the culture broth of P. rudis.

Keywords

Acknowledgement

The authors thank Ms. Ji-Young Oh, Center for University-wide Research Facilities (CURF) at Jeonbuk National University, for NMR measurements.

References

  1. Vargas-Isla R, Capelari M, Menolli NJ, et al. Relationship between Panus lecomtei and P. strigellus inferred from their morphological, molecular and biological characteristics. Mycoscience. 2015;56(6):561-571. https://doi.org/10.1016/j.myc.2015.05.004
  2. Schlegel B, Hartl A, Dahse H-M, et al. Hexacyclinol, a new antiproliferative metabolite of Panus rudis HKI 0254. J Antibiot. 2002;55(9):814-817. https://doi.org/10.7164/antibiotics.55.814
  3. Sekizawa R, Ikeno S, Nakamura H, et al. Panepophenanthrin, from a mushroom strain, a novel inhibitor of the ubiquitin-activating enzyme. J Nat Prod. 2002;65(10):1491-1493. https://doi.org/10.1021/np020098q
  4. Zhang M, Wu F, Wei Z, et al. Characterization and decolorization ability of a laccase from Panus rudis. Enzyme and Microb Technol. 2006;39(1):92-97. https://doi.org/10.1016/j.enzmictec.2005.09.012
  5. Shotwell JB, Koh B, Choi HW, et al. Inhibitors of NF-κB signaling: design and synthesis of a biotinylated isopanepoxydone affinity reagent. Bioorg Med Chem Lett. 2002;12(23):3463-3466. https://doi.org/10.1016/S0960-894X(02)00769-2
  6. Barros-Filho BA, de Oliveira MC, Mafezoli J, et al. Secondary metabolite production by the basidiomycete, Lentinus strigellus, under different culture conditions. Nat Prod Commun. 2012;7(6):771-773.
  7. Lei X, Johnson RP, Porco JA. Total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin. Angew Chem. 2003;115(33):4043-4047. https://doi.org/10.1002/ange.200351862
  8. Cotelle N, Moreau S, Bernier JL, et al. Antioxidant properties of natural hydroquinones from the marine colonial tunicate Aplidium californicum. Free Radic Biol Med. 1991;11(1):63-68. https://doi.org/10.1016/0891-5849(91)90188-9
  9. Cota BB, Rosa LH, Fagundes EMS, et al. A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation. Mem Inst Oswaldo Cruz. 2008;103(3):263-270. https://doi.org/10.1590/S0074-02762008000300007
  10. Lee IK, Jung JY, Kim YS, et al. p-Terphenyls from the fruiting bodies of Paxillus curtisii and their antioxidant properties. Bioorg Med Chem. 2009;17(13):4674-4680. https://doi.org/10.1016/j.bmc.2009.04.064
  11. Favre-Godal Q, Pinto S, Dorsaz S, et al. Identification of antifungal compounds from the root bark of Cordia anisophylla J.S. Mill. J Braz Chem Soc. 2019;30:472-478.