Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63

• Published in: Phytochemistry letters 2019-08, Vol.32, p.162-167
• Main Authors: Gubiani, Juliana R., Oliveira, Michele C.S., Neponuceno, Ricardo A.R., Camargo, Maria J., Garcez, Walmir S., Biz, Andressa R., Soares, Marcos A., Araujo, Angela R., Bolzani, Vanderlan da S., Lisboa, Helen C.F., de Sousa, Paulo T., de Vasconcelos, Leonardo G., Ribeiro, Tereza A.N., de Oliveira, Juliana M., Banzato, Thais P., Lima, Carolina A., Longato, Giovanna B., Batista, João M., Berlinck, Roberto G.S., Teles, Helder L.
• Format: Article
• Language: English
• Subjects: Aspergillus terreus; Endophytic fungus; Fungal alkaloid; Prenylated indole alkaloid
• ISSN: 1874-3900; 1876-7486
• DOI: 10.1016/j.phytol.2019.06.003

[Display omitted] •Endophytic fungus Aspergillus terreus P63 isolated from the roots of the grass Axonopus leptostachyus.•Aspergillus terreus P63 produced one new compound.•New unprecedented carbon skeleton derived from prenylated indole alkaloid.•Compounds identified by NMR and HRESIMS spectra.•Compound with antiproliferative profile for prostate and kidney cancer cell lines. Prenyl indole alkaloids constitute a diverse class of natural products with complex chemical structures and potent biological activities. Investigation of the growth medium EtOAc extract produced by the endophytic fungus Aspergillus terreus P63 collected from roots of the grass Axonopus leptostachyus, yielded the prenylated indole alkaloid, giluterrin, bearing an unprecedented carbon skeleton. The structure of giluterrin was established by analysis of spectroscopic data and HRMS. The absolute configuration of giluterrin was determined by combination of electronic and vibrational circular dichroism analyses. Giluterrin presented antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines.