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DSM 100043产生的新型糖脂生物表面活性剂的结构解析与表征

Structure Elucidation and Characterization of Novel Glycolipid Biosurfactant Produced by DSM 100043.

作者信息

Harahap Andre Fahriz Perdana, Conrad Jürgen, Wolf Mario, Pfannstiel Jens, Klaiber Iris, Grether Jakob, Hiller Eric, Vahidinasab Maliheh, Salminen Hanna, Treinen Chantal, Perino Elvio Henrique Benatto, Hausmann Rudolf

机构信息

Department of Bioprocess Engineering (150k), Institute of Food Science and Biotechnology, University of Hohenheim, Fruwirthstr. 12, 70599 Stuttgart, Germany.

Department of Organic Chemistry (130b), Institute of Chemistry, University of Hohenheim, Garbenstr. 30, 70599 Stuttgart, Germany.

出版信息

Molecules. 2025 Apr 17;30(8):1798. doi: 10.3390/molecules30081798.

Abstract

Microbial biosurfactants have become increasingly attractive as promising ingredients for environmentally friendly products. The reasons for this are their generally good performance and biodegradability, low toxicity, production from renewable raw materials, and benefits for the environment perceived by consumers. In this study, we investigated the chemical structure and properties of a novel glycolipid from a new biosurfactant-producing strain, DSM 100043. Bioreactor cultivation was performed at 30 °C and pH 7.0 for 28 h using 15 g/L glycerol as a carbon source. The glycolipid was successfully purified from the ethyl acetate extract of the supernatant using medium pressure liquid chromatography (MPLC). The structure of the glycolipid was determined by one- and two-dimensional (H and C) nuclear magnetic resonance (NMR) and confirmed by liquid chromatography electrospray ionization mass spectrometry (LC-ESI/MS). NMR analysis revealed the hydrophilic moiety as a glucose molecule and the hydrophobic moieties as 3-hydroxy-5-dodecenoic acid and 3-hydroxydecanoic acid, which are linked with the glucose by ester bonds at the C2 and C3 positions. Surface tension measurement with tensiometry indicated that the glucose-lipid could reduce the surface tension of water from 72.05 mN/m to 24.59 mN/m at 25 °C with a very low critical micelle concentration (CMC) of 5.69 mg/L. Moreover, the glucose-lipid demonstrated very good stability in maintaining emulsification activity at pH 2-8, a temperature of up to 100 °C, and a NaCl concentration of up to 15%. These results show that DSM 100043 produced a novel glycolipid biosurfactant with excellent surface-active properties, making it promising for further research or industrial applications.

摘要

微生物生物表面活性剂作为环保产品的有前景成分,已变得越来越有吸引力。其原因在于它们通常具有良好的性能和生物降解性、低毒性、可由可再生原料生产,以及消费者所认为的对环境有益。在本研究中,我们研究了一种来自新的生物表面活性剂生产菌株DSM 100043的新型糖脂的化学结构和性质。使用15 g/L甘油作为碳源,在30°C和pH 7.0条件下进行生物反应器培养达28小时。通过中压液相色谱(MPLC)从上清液的乙酸乙酯提取物中成功纯化出该糖脂。通过一维和二维(氢和碳)核磁共振(NMR)确定了该糖脂的结构,并通过液相色谱电喷雾电离质谱(LC-ESI/MS)进行了确认。NMR分析表明,亲水部分为一个葡萄糖分子,疏水部分为3-羟基-5-十二碳烯酸和3-羟基癸酸,它们通过酯键在C2和C3位置与葡萄糖相连。用张力测定法进行的表面张力测量表明,该葡萄糖-脂质在25°C下可将水的表面张力从72.05 mN/m降低至24.59 mN/m,临界胶束浓度(CMC)极低,为5.69 mg/L。此外,该葡萄糖-脂质在pH 2 - 8、温度高达100°C以及NaCl浓度高达15%的条件下,在维持乳化活性方面表现出非常好的稳定性。这些结果表明,DSM 100043产生了一种具有优异表面活性性质的新型糖脂生物表面活性剂,使其在进一步研究或工业应用方面具有前景。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/745c/12029617/b9be2bb4681a/molecules-30-01798-g001.jpg

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