Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil‐derived fungus, <i>Aspergillus</i> sp. SDC28
Juliana R. Gubiani, Darlon I. Bernardi, Caio César Pires de Paula, Mirna Helena Regali Seleghim, Antônio G. Ferreira, Andrea N. L. Batista, João M. Batista, Lucianne Ferreira Paes de Oliveira, Simone Possedente de Lira, Joanna E. Burdette, Roberto G. S. Berlinck
Abstract
Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil-derived fungus Aspergillus sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (1) and versiconol (2). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of 1 and 2 was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of 2. Compounds 1 and 2 showed cytotoxic activity against human ovarian cancer cells (OVCAR3).