Valuable furan fatty acids in soybeans and soy products

Abstract

Furan fatty acids (FuFAs) are valuable minor compounds in our food with excellent antioxidant properties. Naturally occurring FuFAs are characterised by a central furan moiety with one or two methyl groups in β-/β’-position of the heterocycle (monomethyl- or M-FuFAs and dimethyl- or D-FuFAs). Comparably high concentrations of D-/M-FuFAs were reported in soybeans, but soy is often consumed as a processed product, such as full-fat soy flour and flakes, soy drink, tofu and texturised soy protein (TSP). Due to the chemical lability of D-/M-FuFAs, e.g. in the presence of light or oxygen, a degradation during the processing is possible. For this purpose, freshly harvested soybeans (n = 4) and differently processed soybean products (n = 22) were analysed on FuFAs. Three FuFAs, i.e. 11-(3,4-dimethyl-5-pentylfuran-2-yl)-undecanoic acid (11D5), 9-(3,4-dimethyl-5-pentylfuran-2-yl)-nonanoic acid (9D5), and 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5), were identified and quantified in all fresh soybeans and most of the processed soy products (n = 20). A trend towards lower D-/M-FuFA contents in higher processed products was observable. Lower FuFA concentrations were usually accompanied with a decrease of the share of the less stable D-FuFAs (9D5, 11D5) in favour of the M-FuFA 9M5. Furthermore, one or two 3,4-nonmethylated furan fatty acids (N-FuFAs), i.e. 8-(5-hexylfuran-2-yl)-octanoic acid (8F6) and partly 7-(5-heptylfuran-2-yl)-heptanoic acid (7F7), were detected in all processed products, but not in the freshly harvested soybeans. Our results indicate that D-/M-/N-FuFAs may serve as suitable markers for both, careful manufacturing processes and adequate storage conditions of soy products.