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微波辅助合成与离子液体:酶法脂肪酰化花色苷单葡萄糖苷的绿色可持续替代途径。

Microwave-Assisted Synthesis and Ionic Liquids: Green and Sustainable Alternatives toward Enzymatic Lipophilization of Anthocyanin Monoglucosides.

机构信息

REQUIMTE/LAQV, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.

REQUIMTE/LAQV, Departamento de Quimica, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.

出版信息

J Agric Food Chem. 2020 Jul 15;68(28):7387-7392. doi: 10.1021/acs.jafc.0c02599. Epub 2020 Jul 1.

Abstract

Anthocyanins recycling and transformations into novel compounds have been of great interest of the scientific community to improve the circular economy and enhance their technological applications. The enzymatic acylation of anthocyanins into lipophilic derivatives by conjugation with fatty acids emerged as one of the approaches; however, the literature describes only the use of organic solvents and conventional heating. In this work, the production of cyanidin-3-glucoside-octanoic acid conjugate combining ionic liquids (ILs), microwave (MW) irradiation, and lipase B as a biocatalyst was attempted for the first time. Overall, the use of MW irradiation could reduce drastically the reaction time, allowing the formation of an acylated product with similar concentrations to the conventional method. On the other hand, the study of the lipophilic conjugate synthesis using different ILs showed that their composition is crucial to achieve the desired enzymatic reaction, and in this case, the combination of an imidazolium derivative as the cation with the triflate as the anion was suitable for the production of this derivative. These promising results achieved through the combination of greener alternatives to those reported in the literature are a starting point for further developments to produce this kind of anthocyanin derivatives exploring such sustainable and ecofriendly conditions.

摘要

花色苷的回收和转化为新型化合物一直是科学界关注的焦点,目的是提高循环经济并增强其技术应用。花色苷通过与脂肪酸结合进行酶酰化,生成亲脂性衍生物,这是一种方法;然而,文献仅描述了使用有机溶剂和常规加热。在这项工作中,首次尝试将离子液体 (ILs)、微波 (MW) 辐射和脂肪酶 B 结合使用,生产矢车菊素-3-葡萄糖-o-辛酸苷缀合物。总体而言,MW 辐射的使用可以大大缩短反应时间,使酰化产物的形成达到与常规方法相似的浓度。另一方面,使用不同 ILs 研究亲脂性缀合物的合成表明,其组成对于实现所需的酶反应至关重要,在这种情况下,将咪唑衍生物作为阳离子与三氟甲磺酸根作为阴离子结合,适合生产这种衍生物。通过将比文献中报道的更环保的替代方案相结合,取得了这些有前途的结果,为进一步开发在这种可持续和环保条件下生产这种花色苷衍生物的方法奠定了基础。

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