Isolation and identification of an antimutagenic phthalate derivative compound from octopus (Paraoctopus limaculatus)

Purpose: To isolate and evaluate the antimutagenic properties of compounds previously identified in octopus (Paraoctopus limaculatus). Methods: Octopus fractions, previously obtained by a sequential thin layer chromatography (TLC) procedure, were subjected to further fractionation by TLC and their anti-mutagenic activity monitored using Salmonella tester strains TA98 and TA100 with metabolic activation (S9) in Ames test. The isolated fractions were subjected to structural studies by Fourier transformed infrared spectroscopy (FTIR), nuclear magnetic resonance (¹H and ¹³C NMR), and gas chromatography-mass spectrometry. Results: Five new fractions were obtained from a previously isolated and reported anti-mutagenic octopus fraction. Fractions RB21321b2 and RB21321b3 inhibited > 80 % of the mutagenicity induced by 500 ng AFB1 on both tester strains and were selected for chemical/structural characterization. Data from IR and 1H and 13C NMR suggested the presence of phthalate type of compounds. GC-MS analysis revealed 278 m/z for both fractions which is consistent with a butyl isobutyl phthalate structure. Conclusion: Based on the findings, the compound responsible for the high anti-mutagenic activity of the isolated fraction from octopus is 1-butyl-2-isobutyl-phthalate.