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Phytofurans are novel metabolites produced by non-enzymatic peroxidation of α-linolenic acid. An unprecedented Payne rearrangement-cyclization of a C2-symmetric bis-epoxide permitted construction of the core 3-hydroxy-2,5-disubstituted tetrahydrofuran. LC-MS/MS investigation provided evidence for the presence of phytofurans in nuts and seeds for the first time.

Consumption of food containing n-3 PUFAs, namely EPA and DHA, are known to benefit health and protect against chronic diseases. Both are richly found in marine-based food such as fatty fish and seafood that are commonly cooked prior to consumption. However, the elevated temperature during cooking potentially degrades the EPA and DHA through oxidation. To understand the changes during different cooking methods, lipid profiles of raw, boiled, pan-fried and baked salmon were determined by LC-MS/MS. Our results showed that pan-frying and baking elevated the concentration of peroxides in salmon, whereas only pan-frying increased the MDA concentration, indicating it to be the most severe procedure to cause oxidation among the cooking methods. Pan-frying augmented oxidized products of n-3 and n-6 PUFAs, while only those of n-3 PUFA were elevated in baked salmon. Notably, pan-frying and baking increased bioactive oxidized n-3 PUFA products, in particular F-4t-neuroprostanes derived from DHA. The results of this study provided a new insight into the application of heat and its effect on PUFAs and the release of its oxidized products in salmon.

Angiogenesis is a key step for tumour growth and metastasis, and anti-angiogenesis has been proposed as an important strategy for cancer therapy. Tryptanthrin is a weakly basic alkaloid isolated from the dried roots of medicinal indigo plants and has been shown to possess anti-tumour activities on various cancer cell types. This study aims to investigate the in vitro and in vivo anti-angiogenic activities of tryptanthrin and to unravel its underlying molecular action mechanisms. Our results show that tryptanthrin inhibited the in vitro proliferation, migration, and tube formation of the human microvascular endothelial cells (HMEC-1) in a concentration-dependent manner and significantly suppressed angiogenesis in Matrigel plugs in mice. Mechanistic studies indicated that tryptanthrin reduced the expression of several pro-angiogenic factors (Ang-1, PDGFB and MMP2). Tryptanthrin was also found to suppress the VEGFR2-mediated ERK1/2 signalling pathway in HMEC-1 cells and molecular docking simulation indicated that tryptanthrin could bound to the ATP-binding site of VEGFR2. Collectively, the present study demonstrated that tryptanthrin exhibited both in vitro and in vivo anti-angiogenic activities by targeting the VEGFR2-mediated ERK1/2 signalling pathway and might have therapeutic potential for the treatment of angiogenesis-related diseases.