The common presence of glycidyl esters (GEs) in refined
vegetable
oils has been a concern for food safety. The present study aimed to
investigate the inhibitory effects of three carotenoids derived from Haematococcus pluvialis microalga on GE formation
in both rice oil and a chemical model during heating. The addition
of astaxanthin (AS), lutein (LU), and β-carotene (CA) at 0.6
mg/g in rice oil can reduce GE formation by 65.0%, 57.1%, and 57.5%,
respectively, which are significantly higher than those achieved by
common antioxidants such as l-ascorbyl palmitate (39.0%),
α-tocopherol (18.5%), tert-butyl hydroquinone
(42.7%), and quercetin (26.2%). UPLC-Q-TOF-MS/MS analysis showed that
two new compounds, that is, propylene glycol monoester and diester
of palmitic acid, were formed in the CA-added chemical model, which
provided direct experimental evidence for the inhibition of antioxidants
including AS, LU, and CA against GE formation not only by indirect
antioxidative action but also by direct radical reactions to competitively
prevent the formation of cyclic acyloxonium intermediates. Furthermore,
it was interestingly found that only AS could react with the GEs.
The adduct of AS with GEs, astaxanthin-3-O-propanetriol esters, was
preliminarily identified using Q-TOF-MS/MS in the heated AS-GE model,
suggesting that reacting with GEs might represent another distinct
mechanism of AS to eliminate GEs.