CC BY-NC-ND 4.0 · Planta Medica International Open 2019; 6(02): e57-e62
DOI: 10.1055/a-1032-3346
Original Papers
Eigentümer und Copyright ©Georg Thieme Verlag KG 2019

Laccaridione C, a Bioactive Polyketide from the Fungus Montagnula sp.

Celso Almeida
1   Fundación MEDINA, Microbiology, Armilla, Spain
Thomas Andrew Mackenzie
2   Fundación MEDINA, Screening and Target Validation, Armilla, Spain
Víctor González-Menéndez
1   Fundación MEDINA, Microbiology, Armilla, Spain
Nuria de Pedro
2   Fundación MEDINA, Screening and Target Validation, Armilla, Spain
Ignacio Pérez-Victoria
3   Fundación MEDINA, Chemistry, Armilla, Spain
Gloria Crespo
3   Fundación MEDINA, Chemistry, Armilla, Spain
Jesús Martín
3   Fundación MEDINA, Chemistry, Armilla, Spain
Olga Genilloud
1   Fundación MEDINA, Microbiology, Armilla, Spain
Francisca Vicente
2   Fundación MEDINA, Screening and Target Validation, Armilla, Spain
Bastien Cautain
2   Fundación MEDINA, Screening and Target Validation, Armilla, Spain
Fernando Reyes
3   Fundación MEDINA, Chemistry, Armilla, Spain
› Author Affiliations
Further Information

Publication History

received 28 August 2019
revised 14 October 2019

accepted 21 October 2019

Publication Date:
18 November 2019 (online)


The new polyketide laccaridione C (1) was obtained by bioassay-guided isolation of organic extracts of the fungal strain CF-223743, isolated from dung collected in a forest of Grand Comoros Island. Its structure was established using spectroscopic methods, namely HRMS and 1D and 2D NMR. The new compound was tested against seven cancer cell lines, evidencing effective activity against melanoma (A2058) with an IC50 of 13.2 µM, and an increased activity against breast cancer (MCF-7) with an IC50 of 3.7 µM. The strain CF-223743 was taxonomically identified as Montagnula sp. based on ITS/28S analysis

Supporting Information

  • References

  • 1 Mondal S, Bandyopadhyay S, Ghosh MK, Mukhopadhyay S, Roy S, Mandal C. Natural products: Promising resources for cancer drug discovery. Anticancer Agents Med Chem 2012; 12: 49-75
  • 2 Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. J Antibiot 2009; 62: 5-16
  • 3 McCourt C, Dolan O, Gormley G. Malignant melanoma: A pictorial review. Ulster Med J 2014; 83: 103-110
  • 4 Morton DL, Essner R, Kirkwood JM, Wollman RC. Malignant melanoma. In: Kufe DW, Pollock RE, Weichselbaum RR, Bast RC, Gansler TS, Holland JF, Frei E. Editors Holland-Frei Cancer Medicine. 6th ed Hamilton: BC Decker Inc; 2006: 1644-1662
  • 5 Al Qathama A, Prieto JM. Natural products with therapeutic potential in melanoma metastasis. Nat Prod Rep 2015; 32: 1170-1182
  • 6 Berg A, Reiber K, Dörfelt H, Walter G, Schlegel B, Gräfe U. Laccaridones A and B, new protease inhibitors from Laccaria amethystea . J Antibiot 2000; 53: 1313-1316
  • 7 Guerriero A, DʼAmbrosio M, Cuomo V, Pietra F. A novel, degraded polyketidic lactone, leptosphaerolide, and its likely diketone precursor, leptosphaerodione. Isolation from cultures of the marine ascomycete Leptosphaeria oraemaris (Linder). Helv Chim Acta 1991; 74: 1445-1450
  • 8 Perez-Victoria I, Martin J, Reyes F. Combined LC/UV/MS and NMR Strategies for the Dereplication of Marine Natural Products. Planta Med 2016; 82: 857-871
  • 9 Berg A, Gaefe U, Reiber K, Dahse HM, Doerfelt H. New laccaridione compounds useful as protease inhibitors, e. g. for treating cancer, autoimmune diseases and allergies. DE Patent 10037982 A1: 2002
  • 10 Berg A, Würzner R, Doerfelt H. Using fungal naphthopyran-8,9-diones as inhibitors of aspartyl protease, useful for treatment of infection by Candida or human immune deficiency virus. DE Patent 10349511 A1: 2005
  • 11 Tamio M, Tetsuya T, Katsuhiko A, Shingo K. EC1007 Compound. JP Patent 2000053674 2000
  • 12 Boss D, Maurhofer M, Schläpfer E, Défago G. Elsinochrome A production by the bindweed biocontrol fungus Stagonospora convolvuli LA39 does not pose a risk to the environment or the consumer of treated crops. Plant Pathol 2007; 59: 194-205
  • 13 Surup F, Medjedovic A, Schroers HJ, Stadler M. Production of Obionin A and Derivatives by the Sooty Blotch Fungus Microcyclospora malicola . Planta Med 2015; 81: 1339-1344
  • 14 Falkensammer B, Pleyer L, Ressler S, Berg A, Borg-von Zepelin M, Nagl M, Lass-Flörl C, Speth C, Dierich MP, Würzner R. Basidiomycete metabolites attenuate virulence properties of Candida albicans in vitro . Mycoses 2008; 51: 505-514
  • 15 Ayers S, Graf TN, Adcock AF, Kroll DJ, Shen Q, Swanson SM, Wani MC, Darveaux BA, Pearce CJ, Oberlies NH. Obionin B: An o-pyranonaphthoquinone decaketide from an unidentified fungus (MSX 63619) from the Order Pleosporales. Tetrahedron Lett 2011; 52: 5128-5230
  • 16 Poch GK, Gloer JB. Obionin A: A new polyketide metabolite from the marine fungus Leptosphaeria obiones . Tetrahedron Lett 1989; 30: 3483-3486
  • 17 Martín J, Crespo G, González-Menéndez V, Pérez-Moreno G, Sánchez-Carrasco P, Pérez-Victoria I, Ruiz-Pérez LM, González Pacanowska D, Vicente F, Genilloud O, Bills GF, Reyes F. MDN-0104, an antiplasmodial betaine lipid from Heterospora chenopodii . J Nat Prod 2014; 77: 2118-2123
  • 18 Bills GF, Foster MS. Appendix II. Formulae for selected materials used to isolate and study fungi and fungal allies. In: Mueller GM, Bills GF, Foster MS. Editors Biodiversity of Fungi: Inventory and Monitoring Methods. Boston: Elsevier Academic Press; 2004: 595-618
  • 19 Gonzalez-Menendez V, Martin J, Siles JA, Gonzalez-Tejero MR, Reyes F, Platas F, Tormo JR, Genilloud O. Biodiversity and chemotaxonomy of Preussia isolates from the Iberian Peninsula. Mycol Progress 2017; 16: 713-728
  • 20 Ronquist F, Huelsenbeck JP. MrBayes 3: Bayesian phylogenetic inference under mixed models. Bioinformatics 2003; 19: 1572-1574
  • 21 Patel MR, Patel SK. Cytotoxic activity of methanolic extract of Artocarpus heterophyllus against A549, Hela and MCF-7 cell lines. J Appl Pharm Sci 2011; 1: 167-171