Enrichment of linoleic acid from yellow horn seed oil through low temperature crystallization followed by urea complexation method and hypoglycemic activities.

Yellow horn (Xanthoceras sorbifolia Bunge) contained abundant linoleic acid (LA), accounting for about 44% of its lipid. Here, LA was enriched by low temperature crystallization followed by urea complexation, and the optimal enrichment conditions were optimized with response surface methods (3:1 ratio of EtOH/FFA, crystallization at - 25 °C for 24.5 h; 2:1 ratio of urea/FFA1, 6.6:1 ratio of EtOH/urea, crystallization at - 10 °C for 22.4 h). Under these conditions, the final LA content and recovery were 97.10% and 62.09%, respectively. In vitro hypoglycemic studies suggested that the LA extract with stronger inhibition on α-glucosidase and lower one on α-amylase than acarbose exhibited a positive control for carbohydrate digestion with lower adverse effects. The enzyme kinetics and Lineweaver-Burk plots analyses revealed a reversible competitive inhibition on α-amylase and α-glucosidase. The findings of this research provided insights for the development of the LA extract as the functional component of health food. Supplementary Information: The online version contains supplementary material available at 10.1007/s10068-023-01327-9.

Syntheses and high selective cytotoxicity of dehydroabietylamine C-ring nitration derivatives.

To find more effective anticancer agents, a series of novel dehydroabietylamine (DA) derivatives were synthesized, focusing on C-ring nitro modifications and C-18 imide introduction. Their cytotoxic activities against human tumor cell line HeLa (cervix), MCF-7 (breast), A549 (lung), HepG2 (liver), and nonmalignant cell line HUVEC (umbilical vein) in vitro were screened. The C-18 imide heterocyclic compounds 1, 2, and C-ring 14-nitro substituted 14 exhibited moderate to good cytotoxic activities and significant selectivity towards malignant cell lines. More importantly, they were significantly less cytotoxic to nonmalignant cells (HUVEC) than the parent compound and positive control doxorubicin hydrochloride (DOX). Meantime the mechanism of cytotoxicity of DA derivatives was studied. Annexin V-FITC/PI double-staining analysis suggested that cytotoxicity of compounds 2 and 14 was associated with early apoptosis induction. The interaction between compounds and DNA (herring sperm DNA) was studied using absorption spectral analysis and ethidium bromide (EB) fluorescence displacement experiments, the results exhibited that the binding of the compound to DNA was in the intercalative mode. The structure-activity relationship discussion implied that introduction of the nitro-group, especially the 14-nitro group, can significantly improve the cytotoxicity of dehydroabietylimide compounds. The relatively high cytotoxicity and significant high selectivity of compounds 2 and 14 indicated that they were particularly noteworthy. NO released amounts indicated that the amounts of NO released by the compounds bearing nitro-group were quite well associated positive correlation with their cytotoxic activity, which provide a new strategy for structure design of DA anticancer agents in the future.