The fatty acid composition of pomegranate (Punica granatum L.) seed oil (PSO) is dominated by punicic acid, a conjugated linolenic acid (18:3ω-5). As a free fatty acid, punicic acid is rapidly oxidized in air and extensively isomerizes upon acid-catalyzed methylation at 90 °C. In contrast, triacylglycerol-bound punicic acid in PSO was unchanged by simulated gastric conditions and was degraded by 5-7% by severe heating (up to 170 °C for 4 h), as herein assessed by gas chromatography, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C NMR, and high-resolution electrospray ionization mass spectrometry. Total polar compounds of PSO were slightly affected by thermal stress, accounting for 5.71, 6.35, and 9.53% (w/w) in the unheated, heated at mild temperature (50 °C, 2 h), and heated at frying temperature (170 °C, 4 h) PSO, respectively. These findings support from a structural standpoint the potential use of PSO as a health-promoting edible oil.
Keywords: conjugated linolenic acids; isomerization of fatty acids; oxidative stability; pomegranate seed oil; punicic acid.