A novel chemoenzymatic synthesis of phytosteryl caffeates and assessment of their antioxidant activity

Add time:08/22/2019    Source:sciencedirect.com

Phytosterols and their derivatives are relevant in food, pharmaceuticals, and cosmetics. In addition to their well-known effect in lowering low-density lipoprotein (LDL) cholesterol, they also possess other biological activities, such as anti-inflammatory, anti-atherogenicity, and anti-carcinogenic potential. A novel method was developed for chemoenzymatic synthesis of phytosteryl caffeates through an intermediate vinyl caffeate, which was first chemically produced and subsequently esterified with phytosterols through lipase-assisted alcoholysis. The structures of the phytosteryl caffeates were confirmed by infrared (IR) and high performance liquid chromatography–mass spectrometry/mass spectrometry (HPLC–MS/MS). The ORAC values of phytosteryl caffeates were two times higher than that of caffeic acid. In a meat model system, the antioxidant activity of phytosteryl caffeates was higher than caffeic acid and vinyl caffeate, and that of butylated hydroxyanisole (BHA), a commonly used synthetic antioxidant. The results indicate that phytosteryl caffeates have a good potential for use as food antioxidants.

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