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

2019; Elsevier BV; Volume: 32; Linguagem: Inglês

10.1016/j.phytol.2019.06.003

1876-7486

Juliana R. Gubiani, Michele C.S. Oliveira, Ricardo A.R. Neponuceno, Maria José de Camargo, Walmir Silva Garcez, Andressa R. Biz, Marcos Antônio Soares, Ângela R. Araújo, Vanderlan da Silva Bolzani, Helen Cristina Fávero Lisboa, Paulo Teixeira de Sousa, Leonardo Gomes de Vasconcelos, Tereza Auxiliadora Nascimento Ribeiro, Juliana Magalhães de Oliveira, Thais Petrochelli Banzato, Carolina A. de Lima, Giovanna Barbarini Longato, João M. Batista, Roberto G. S. Berlinck, Helder Lopes Teles,

Plant chemical constituents analysis

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.