The synthesis of certain fatty acid ester derivatives of trehalose and an investigation of their emulsifying properties and bioactivities
Bio-based surfactants exerting both functional and nutritional properties are needed in the food industry. This study reports the one-pot synthesis, using a Novozym 435-catalyzed trans-esterification protocol, of a new family of such compounds, namely a homologous series of 6-O-acylated trehalose and 6,6′-di-O-acylated trehalose derivatives incorporating long-chain fatty acid residues (12–22 carbons). These mono- and di-esters exhibited HLB values within the 8.3 to 14.7 range and their performance as surface-active compounds, penetration enhancers and anti-cancer agents have been evaluated. They were found to be excellent emulsifiers, maintaining oil-in-water emulsions with 566–742 nm mean oil-particle sizes and with the stability of these only gradually deteriorating over a 15-day storage period and during in vitro digestion.
Highlights
Mono-esters 2–4 embodying shorter side-chains (12–16 carbons) proved to be excellent foaming agents while congeners 4–6 incorporating longer side-chains (16–20 carbons) served as penetration enhancers capable of reversibly opening tight junctions in Caco-2 cell mono-layers. Mono-esters 5–7, as well as di-esters 11–13, exerted weak cytotoxic effects on seven human cancer cell lines. This work should serve as a useful guide for the development of the multi-functional properties of such trehalose esters in the food and related industries.
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Materials
Trehalose (99.5%) was purchased from Macklin Co. Ltd. (Shanghai, China) while vinyl acetate (98.0%), vinyl laurate (>99.0%), vinyl myristate (>99.0%), vinyl palmitate (>96.0%), vinyl stearate (>95.0%), oleic acid (>85.0%) and erucic acid (>85.0%) were purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). The commercial sucrose esters P-1570 and S-970 were obtained from the Mitsubishi Chemical Foods Corporation (Tokyo, Japan). Dihydrolevoglucosenone (Cyrene™) and t-BuOH were purchased from CIRCA Group Pty Ltd (Victoria, Australia) and the Energy Chemical Co., Ltd. (Shanghai, China), respectively. Novozyme 435 was obtained from Novo Nordisk (Bagværd, Denmark) whereas Lipase (Type II, L3126 from porcine pancreatic pancreatin, pepsin (77,160, from porcine gastric mucosa) and mucin (Type II, M2378 from porcine stomach) were all supplied by Sigma-Aldrich (Shanghai, China). Virgin olive oil (Olivia™, ex. Tunisia) was purchased from a local supermarket. All solutions and emulsions were prepared using double-distilled water produced using a Milli-Q water purification system (Millipore, Billerica, MA). Other reagents and solvents employed in this study were all analytical reagent (AR) grade and were used as received.
Jia-Qing Chen, Yao-Wen Hai, Chun Qing, Min-Yi Liang, Martin G. Banwell, Ping Lan, The synthesis of certain fatty acid ester derivatives of trehalose and an investigation of their emulsifying properties and bioactivities, LWT, Volume 187, 2023, 115369, ISSN 0023-6438, https://doi.org/10.1016/j.lwt.2023.115369
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