食品科学 ›› 2021, Vol. 42 ›› Issue (24): 149-158.doi: 10.7506/spkx1002-6630-20201216-200

• 生物工程 • 上一篇    

海藻糖脂肪酸二酯的酶法合成及性质

汪淑珍   

  1. (暨南大学食品科学与工程系,广东 广州 510632)
  • 发布日期:2021-12-30

Enzymatic Synthesis and Properties of Trehalose Fatty Acid Diesters

WANG Shuzhen   

  1. (Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China)
  • Published:2021-12-30

摘要: 采用固定化脂肪酶Novozym 435催化选择性合成6,6’-O-海藻糖脂肪酸二酯。在叔丁醇-吡啶(11∶9,V/V)混合溶剂中,通过海藻糖和不同碳链长度(C6~C18)的脂肪酸乙烯酯发生酯交换反应实现,海藻糖和脂肪酸乙烯酯物质的量比为1∶4。通过核磁共振波谱及质谱分析对产物进行结构鉴定,分析产物的亲水亲油平衡(hydrophilic lipophilic balance,HLB)值、发泡性能和热稳定性,同时用噻唑蓝法分析该系列海藻糖脂肪酸二酯的细胞毒性。结果表明:结构鉴定其为海藻糖脂肪酸二酯,产物得率为43%~75%;海藻糖癸酸二酯和海藻糖月桂酸二酯具有较好的发泡性能(起泡性分别为101.00%和142.67%,泡沫稳定性(80?min内)分别为40%~60%和50%~70%),海藻糖油酸二酯热稳定性最佳(温度达到350?℃时剩余质量仍为60.58%);细胞毒性结果表明海藻糖油酸二酯安全、低毒。研究结果为开发食品领域高附加值的新型糖酯类非离子型表面活性剂提供了新方向。

关键词: 固定化脂肪酶;酯交换反应;发泡性;热稳定性;细胞毒性

Abstract: This research explored the use of immobilized lipase Novozym 435 to catalyze selective synthesis of 6,6’-O-acyltrehalose diesters through the transesterification of trehalose with fatty acid vinyl esters of different carbon chain lengths (C6–C18) at a molar ratio of 1:4 in a mixed solvent of tert-butanol and pyridine (11:9, V/V). The chemical structures of the products were identified by nuclear magnetic resonance (NMR) and mass spectrometry (MS), the hydrophilic lipophilic balance (HLB), foaming properties and thermostability were determined, and the cytotoxicity was evaluated by the methyl thiazolyl tetrazolium (MTT) assay. It turned out that a series of trehalose fatty acid diesters were formed, with a yield between 43% and 75%. The trehalose didecanoate and trehalose dilaurate had good foaming properties (foamability of 101.00% and 142.67%, and foam stability (within 80 min) of 40%–60% and 50%–70%, respectively). The trehalose dioleate had the best thermal stability with a retention rate of 60.58% at 350 ℃. Moreover, it was found that these trehalose fatty acid esters were safe and lowly toxic. To conclude, this study may point out a new direction for the development of new types of value-added, non-ionic surfactants for the food industry.

Key words: immobilized lipase; transesterification; foaming properties; thermal stability; cytotoxicity

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