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Protulactones A and B: Two New Polyketides from the Marine-derived Fungus Aspergillus sp. SF-5044

  • Sohn, Jae-Hak (College of Medical and Life Sciences, Silla University) ;
  • Oh, Hyun-Cheol (College of Medical and Life Sciences, Silla University)
  • Received : 2010.03.02
  • Accepted : 2010.04.20
  • Published : 2010.06.20

Abstract

Protulactones A (1) and B (2), two new polyketide-derived fungal metabolites, have been isolated from an EtOAc extract of the marine-derived fungus Aspergillus sp. SF-5044 by various chromatographic methods. The structures of 1 and 2 were mainly determined by analysis of the NMR spectroscopic data and MS data, along with chemical methods such as Mosher method. Protulactones A (1) and B (2) are new members of polyketide-derived secondary metabolites, possessing unique ring systems among the fungal metabolites produced by the genus Aspergillus.

Keywords

References

  1. Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discov. 2009, 8, 69. https://doi.org/10.1038/nrd2487
  2. Fenical, W.; Jensen, P. R. Nat. Chem. Biol. 2006, 2, 666. https://doi.org/10.1038/nchembio841
  3. Bugni, T. S.; Ireland, C. M. Nat. Prod. Rep. 2004, 21, 143. https://doi.org/10.1039/b301926h
  4. Konig, G. M.; Kehraus, S.; Seibert, S. F.; Abdel-Lateff, A.; Muller,D. ChemBioChem 2006, 7, 229. https://doi.org/10.1002/cbic.200500087
  5. Choi, Y.-H.; Sohn, J.-H.; Lee, D.; Kim, J. K.; Kong, I. S.; Ahn, S.C.; Oh, H. Tetrahedron Lett. 2008, 49, 7128. https://doi.org/10.1016/j.tetlet.2008.09.143
  6. Kim, M.-Y.; Sohn, J. H.; Ahn, J. S.; Oh, H. J. Nat. Prod. 2009, 72, 2065. https://doi.org/10.1021/np900464p
  7. Seo, C.; Sohn, J. H.; Oh, H.; Kim, B. Y.; Ahn, J. S. Bioorg. Med. Chem. Lett. 2009, 19, 6095. https://doi.org/10.1016/j.bmcl.2009.09.025
  8. Seo, C.; Oh, H. Bull. Korean Chem. Soc. 2009, 30, 1181. https://doi.org/10.5012/bkcs.2009.30.5.1181
  9. Fang, X.P.; Anderson, J. E.; Chang, C.-J.; Fanwick, P. E.; Mc-Laughlin, J. L. J. Chem. Soc. Perkin Trans. 1 1990, 1655.
  10. Seco, J. M.; Quinnoa, E.; Riguera, R. Chem. Rev. 2004, 104, 17. https://doi.org/10.1021/cr000665j
  11. Su, B.-N.; Park, E. J.; Mbwambo, Z. H.; Santarsiero, B. D.; Mesecar, A. D.; Fong, H. H. S.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2002, 65, 1278. https://doi.org/10.1021/np0202475
  12. Dictionary of Natural Products on CD-ROM, Chapman & Hall/CRC Press: Boca Raton, FL, 2007.
  13. Takeda, Y.; Okada, Y.; Masuda, T.; Hirata, E.; Shinzato, T.; Takushi, A.; Yu, Q.; Otsuka, H. Chem. Pharm. Bull. 2000, 48, 752. https://doi.org/10.1248/cpb.48.752

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  2. Marine natural products vol.29, pp.2, 2012, https://doi.org/10.1039/C2NP00090C
  3. Fungal natural products in research and development vol.31, pp.10, 2014, https://doi.org/10.1039/C4NP00060A
  4. Total Synthesis, Configuration Assignment, and Cytotoxic Activity Evaluation of Protulactone A vol.80, pp.5, 2017, https://doi.org/10.1021/acs.jnatprod.7b00212
  5. ChemInform Abstract: Protulactones A (I) and B (II): Two New Polyketides from the Marine-Derived Fungus Aspergillus sp. SF-5044. vol.41, pp.45, 2010, https://doi.org/10.1002/chin.201045207
  6. Asperlin From the Marine-Derived Fungus Aspergillus sp. SF-5044 Exerts Anti-inflammatory Effects Through Heme Oxygenase-1 Expression in Murine Macrophages vol.116, pp.3, 2010, https://doi.org/10.1254/jphs.10219fp
  7. Total Synthesis of Tetraketide and Cryptorigidifoliol I via a Sequential Allylation Strategy vol.79, pp.11, 2016, https://doi.org/10.1021/acs.jnatprod.6b00443
  8. Recent Advances in Total Synthesis of Bioactive Furo[3,2‐ b ]furanone Natural Products vol.9, pp.4, 2010, https://doi.org/10.1002/ajoc.201900714
  9. Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites vol.12, pp.None, 2010, https://doi.org/10.3389/fmicb.2021.804333