Lipase-Catalyzed Synthesis of Sugar Esters in Honey and Agave Syrup

Abstract

Honey and agave syrup are high quality natural products and consist of more than 80% sugars. They are used as sweeteners, and are ingredients of cosmetics or medical ointments. Furthermore, both have low water content, are often liquid at room temperature and resemble some known sugar-based deep eutectic solvents (DES). Since it has been shown that it is possible to synthesize sugar esters in these DESs, in the current work honey or, as vegan alternative, agave syrup are used simultaneously as solvent and substrate for the enzymatic sugar ester production. For this purpose, important characteristics of the herein used honey and agave syrup were determined and compared with other available types. Subsequently, an enzymatic transesterification of four fatty acid vinyl esters was accomplished in ordinary honey and agave syrup. Notwithstanding of the high water content for transesterification reactions of the solvent, the successful sugar ester formation was proved by thin-layer chromatography (TLC) and compared to a sugar ester which was synthesized in a conventional DES. For a clear verification of the sugar esters, mass determinations by ESI-Q-ToF experiments and a NMR analysis were done. These environmentally friendly produced sugar esters have the potential to be used in cosmetics or pharmaceuticals, or to enhance their effectiveness.

Recent advances in the enzymatic synthesis of lipophilic antioxidant and antimicrobial compounds

“…Unusual and fascinating methods of obtaining glycolipids were presented by Siebenhaller et al ( 2018 ) and El-Baz et al ( 2021 ). In the first article honey and agave syrup were used simultaneously as solvents and substrates for the enzymatic transesterification of four fatty acid vinyl esters (vinyl octanoate, vinyl decanoate, vinyl laurate, and vinyl palmitate).…”

“…In the first article honey and agave syrup were used simultaneously as solvents and substrates for the enzymatic transesterification of four fatty acid vinyl esters (vinyl octanoate, vinyl decanoate, vinyl laurate, and vinyl palmitate). Due to the low water content and liquid form reminding sugar-based deep eutectic solvents (DES), these substrates were successfully used in the synthesis of glycolipids with potential use in cosmetics and pharmaceutical industries (Siebenhaller et al 2018 ). El-Baz et al ( 2021 ) proposed single-cell oils (SCO) generated by Cunninghamella echinulata , Umbelopsis isabellina or Nannochloropsis gaditana , as well as olive oil and eicosapentaenoic acid (EPA) concentrate, as acyl donors in the enzymatic synthesis of glucose fatty acid esters.…”

Influence of Chemical Modifications of Polyhydroxyalkanoate-Derived Fatty Acids on Their Antimicrobial Properties

“…A quantity of 100 mg mL −1 of molecular sieves (4Å) was added to withdraw the water formed. Reactions were initiated by addition of 12 mg mL −1 of an enzyme (Thermomyces lanuginosus lipase herein referred to as TL-IM), with shaking (240 rpm), at 55 • C for 24 h (New Brunswick Scientific Exella E24 Incubator Shaker Series; (Figure 2)) [36,37,47]. Samples were collected at set intervals and were analysed on HPLC-MS system.…”

Enhanced Bioactivity of Tailor-Made Glycolipid Enriched Manuka Honey

“…This DES reaction system, later qualified as “2-in-1”, with DES simultaneously serving as a solvent plus substrate of literally unlimited concentration was, more recently, successfully applied by our group. This time we used honey as a solvent and its components, essentially sugars being fructose and glucose, as substrates [ 12 ]. This synthesis relies on the use of the immobilized lipase from C. antarctica (iCalB or Novozym 435 ® ) for the transesterification reaction between vinyl esters and sugars that are naturally present in honey.…”