School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China.
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China.
J Agric Food Chem. 2023 May 24;71(20):7689-7702. doi: 10.1021/acs.jafc.3c00527. Epub 2023 May 11.
Arbutin, salidroside, polydatin, and phlorizin are typically natural bioactive phenolic glycosides. To improve the liposolubility and bioavailability, highly liposoluble derivatives including 6'--lauryl arbutin, 6'--lauryl salidroside, 6″--lauryl polydatin, and 6″--lauryl phlorizin were efficiently synthesized by enzymatic acylation in a green solvent 2-MeTHF. Their reaction conversions reached 84.4, 99.5, 99.8, and 89.1%, respectively, when catalyzed by Lipozyme 435 at 20 mg/mL at 50 °C. As expected, the derivatives had high log (1.66-2.37) and retained good antioxidant activity, making them potential alternatives to butylated hydroxytoluene (BHT) and -butyl-hydroquinone (TBHQ) in lipid systems. Then, the intestinal permeability characteristics and metabolism of phenolic glycosides and their derivatives were investigated based on Caco-2 monolayers. The permeability of polydatin and phlorizin was mainly through active transport, but that of arbutin and salidroside involved both passive diffusion and active uptake. The acylated derivatives suffered from severe CES-mediated hydrolysis but exhibited a larger transported amount than phenolic glycosides.
熊果苷、红景天苷、白藜芦醇苷和根皮苷通常是天然生物活性酚糖苷。为了提高脂溶性和生物利用度，通过在绿色溶剂 2-MeTHF 中用酶酰化反应高效合成了高度脂溶性衍生物，包括 6'--月桂酰基熊果苷、6'--月桂酰基红景天苷、6″--月桂酰基白藜芦醇苷和 6″--月桂酰基根皮苷。当在 50°C 下以 20mg/mL 的浓度用 Lipozyme 435 催化时，它们的反应转化率分别达到 84.4%、99.5%、99.8%和 89.1%。正如预期的那样，这些衍生物具有高的 logP 值（1.66-2.37），并且保留了良好的抗氧化活性，使它们成为脂质体系中丁基羟基甲苯（BHT）和叔丁基对苯二酚（TBHQ）的潜在替代品。然后，基于 Caco-2 单层细胞研究了酚糖苷及其衍生物的肠道通透性特征和代谢。白藜芦醇苷和根皮苷的通透性主要是通过主动转运，而熊果苷和红景天苷的通透性则涉及被动扩散和主动摄取。酰化衍生物受到严重的 CES 介导的水解，但转运量大于酚糖苷。
