新科斯糖的生物制备及其月桂酸酯的酶法合成
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摘要
新科斯糖是一种蔗果三糖族低聚果糖，具有较1F-低聚果糖更好的促益生菌能力，被称为“高效益生元”，是一种功能性甜味剂。然而，由于植物提取新科斯糖产量较低且受季节性限制，而微生物发酵法由于能产合成新科斯糖的酶（~6G-果糖苷酶）的微生物较少且产量低，不具备工业化生产潜力，因此目前尚未有商品化的新科斯糖产品问世。本研究首先开发了法夫酵母全细胞法生产新科斯糖的工艺，确立了~6G-果糖苷酶和虾青素联产发酵方式，以期降低新科斯糖的生产成本，加速其工业化生产进程。同时，研究了高纯度（P90）新科斯糖的食品加工性质，以对新科斯糖将来在食品中的应用提供理论指导。最后，对新科斯糖分子进行了酯化改性，以期进一步扩大新科斯糖的应用范围。
通过考察法夫酵母全细胞产新科斯糖的规律，确定其最佳产糖工艺条件。法夫酵母细胞在中性pH条件下显示了最佳的果糖苷酶活力；细胞浓度与新科斯糖产量非正相关，高浓度的细胞（>80g/L）会导致合成的新科斯糖水解；蔗糖浓度的增加可以显著增加新科斯糖产量，但同时会降低新科斯糖的生产效率；提高反应温度会显著增加法夫酵母细胞的果糖苷酶活力；细胞酶活特性与其种龄密切相关，指数生长期的细胞具有较高的果糖苷酶活力，稳定期的细胞具有较高的水解酶活力。在优化的工艺条件即：细胞种龄32h，浓度80g/L，蔗糖水溶液浓度400g/L，转化温度30℃，转化时间4h，新科斯糖产量可以达到227.72g/L。
根据法夫酵母可产虾青素作为高附加值产品的特点，优化了~6G-果糖苷酶和虾青素联产的培养基成分和发酵条件，以期降低新科斯糖的生产成本。单因素实验结果显示蔗糖和玉米浆是~6G-果糖苷酶和虾青素联产的最佳碳源和氮源；Plackett-Burman实验设计优化结果显示玉米浆和pH是影响~6G-果糖苷酶和虾青素联产的关键因素；中心组合实验结果显示玉米浆浓度为52.5mL/L，pH为7.9时，~6G-果糖苷酶和虾青素联产可以达到最佳产量，分别为242.57U/mL和5.23mg/L；在优化的培养条件下，采用全细胞生物转化工艺，新科斯糖的最大生产效率为119.06g/L/h，且成本分析显示培养基成本较优化前降低了66.3%。此研究进一步加速了新科斯糖的工业化生产进程。
通过模拟不同的杀菌热处理条件，研究了新科斯糖的酸热稳定性，结果表明：新科斯糖在中性和碱性环境下均非常稳定性，可耐受巴氏杀菌（85℃，60min），高温短时间（100℃，30min和121℃，20min）及超高温瞬时（135℃，30s）热处理。在酸性环境下，pH为2和3的新科斯糖溶液经85℃，30min热处理，保留率分别为42.04%和78.99%；pH为4的新科斯糖溶液经100℃，30min和121℃，20min热处理，保留率分别为97.08%和89.83%。运用DSC技术，研究了新科斯糖对大米淀粉糊化及老化性质的影响，结果显示：新科斯糖可以提高大米淀粉初始糊化温度，与低聚果糖，异麦芽糖及蔗糖相比，对初始糊化温度的增加程度大小顺序为：低聚果糖>新科斯糖>异麦芽糖>蔗糖；新科斯糖可以降低淀粉糊化焓值，降低程度与新科斯糖的加入量成正相关性。新科斯糖对淀粉老化行为影响结果表明：淀粉在4℃储藏时，低浓度（10%）新科斯糖在短期内（7天）和长期内（28天）均可以显著抑制淀粉的老化；而高浓度新科斯糖（30%）在长期内可以抑制淀粉老化。淀粉储藏在25℃时，低浓度（10%）的新科斯糖在长期内（28天）会抑制淀粉老化，其他情况下对淀粉老化行为影响效果不显著。与FOS，IMO相比，新科斯糖抗淀粉老化效果优于FOS和IMO。
采用月桂酸乙烯酯成功对新科斯糖进行了酰化改性，经LC-MS初步鉴定产物为新科斯糖月桂酸单酯。通过对新科斯糖月桂酸酯合成规律的考察，确定了最佳反应条件：反应体系为DMSO和2-甲基-2-丁醇（2：8；v/v），新科斯糖与月桂酸乙烯酯的分子摩尔比为1：12，反应温度为50℃，分子筛添加量为100g/L，Novozyme435添加量为10g/L，反应32h后，转化率达到82.38%。在对反应进程研究的基础上，制定了新科斯糖补料策略（每隔8h补新科斯糖0.01M），连续补加8次后，新科斯糖月桂酸酯的产量提高了4.47倍，达到61.35mg/mL。采用C18固相萃取色谱柱对合成的新科斯糖月桂酸酯进行了纯化，并采用1H和13C NMR，COSY和HMQC对合成的糖酯进行了结构鉴定，结果显示糖酯为新科斯糖-6-月桂酸酯。最后，采用Du Nouy吊片法测定了其CMC值，结果为352μmol/L。
Neokestose, a novel fructooligosaccharide (FOS), was reported to possess superiorprebiotic activity to commercial FOS. Such favorable functionalities may boost the marketdemand of neo-FOS. However, no commercial neo-FOS have been produced until now,mainly due to the high cost for their trace amount extraction from vegetables and fruits ortheir low microbial productivity via~6G-fructofuranosidase (~6G-FFase). The whole-cellbiotransformation process, and simultaneous production of~6G-FFase and astaxanthin byXanthophyllomyces dendrorhous were firstly developed to make neokestose practicallyfeasible for commercial production in the present study. Moreover, the properties for foodprocessing were investigated to provide theoretical guidance for the application in foodproduct. Finally, the neokestose was acylated to enlarge the application of this functionalfactor.
The effects of production parameters on the biotransformation of sucrose wereinvestigated to enhance the yield of neokestose by Xanthophyllomyces dendrorhous. Cellsshowed optimal~6G-FFase activity at neutral pH and the yield of neokestose showed nosignificant differences between buffer and buffer-free systems. Cell concentration (>80g/L)negatively affected the maximum neokestose yield. Sucrose concentration positivelyincreased the maximum yield of neokestose. Elevating the reaction temperature to30℃, theneokestose productivity increased1.85-fold compared with that at20℃. Meanwhile, cell ageof32h enabled the biotransformation of sucrose more efficiently. In addition, free cellsexhibited a higher productivity over immobilized cells. The maximum neokestoseconcentration finally reached227.72g/L from400g/L sucrose under the optimal conditions.
The effects of medium composition and culture conditions on the simultaneousproduction of~6G-FFase and astaxanthin were investigated to reduce the capital cost ofneokestose production by Xanthophyllomyces dendrorhous. The sucrose and corn steep liquor(CSL) were found to be the optimal carbon source and nitrogen source, respectively. CSL andinitial pH were selected as the critical factors using Plackett-Burman design. Maximum~6G-FFase242.57U/mL with5.23mg/L astaxanthin was obtained at CSL52.5mL/L and pH7.9by central composite design. Neokestose yield could reach238.12g/L under the optimizedmedium conditions. Cost analysis suggested66.3%of substrate cost was reduced comparedwith that before optimization. These results demonstrated that the optimized medium andculture conditions could significantly enhance the production of~6G-FFase and astaxanthinand remarkably decrease the substrate cost, which opened up possibilities to produceneokestose industrially.
The heat and pH stability of neokestose was evaluated compared with commercial FOS bysimulating different thermo sterilization. The results showed that neokestose at neutral andalkaline pH displayed high heat and pH stability during pasteurization (85℃,30min), hightemperature for short time sterilization (100℃,30min and121℃,20min) and ultra hightemperature sterilization (135℃,30s). The neokestose at pH2and pH3retained42.04%and78.99%during pasteurization (85℃,30min), indicating a significant degradation. Neokestoseat pH4retained97.08%and89.83%during high temperature short time sterilization (100℃,30min and121℃,20min), suggesting a relatively high stability compared to that of FOS. Onthe other hand, the effects of neokestose on the gelatinization and retrogradation of rice starchwere studied compared with FOS, IMO and sucrose using a differential scanning calorimetry(DSC), and the results suggested that the addition of neokestose could increase thegelatinization temperature of rice starch in the order of neokestose>FOS>IMO>sucrose, andreduce the gelatinization enthalpy which showed negatively correlation with the concentrationof neokestose. Moreover, the effect of neokestose on the retrogradation of rice starch wasevaluated. The results indicated that10%of neokestose could significantly retard theretrogradation of rice starch when stored at4℃for short term (7days) and long term (28days);30%of neokestose could inhibit the retrogradation of rice starch when stored at4℃for longterm (28days);10%of neokestose could retard the retrogradation of rice starch when stored at25℃for long term (28days),30%of neokestose had no significant effect on the retragradationof rice starch when stored at25℃. Furthermore, neokestose showed better inhibition effect onthe retrogradation of rice starch compared with that of FOS and IMO at the tested conditions.
An acylation modification of neokestose using Candida antarctica lipase B asbiocatalyst was investigated aiming to further broaden the potential application of neokestose.The process conditions were optimized, and the highest conversion rate of82.38%wasachieved under the optimized conditions:20%DMSO in2-methyl-2-butanol (v/v), molarratio of12(vinyl laurate to neokestose), temperature of50℃, molecular sieves of100g/L.Finally, a neokestose feeding strategy was developed based on the kinetics of neokestoseacylation, driving neokestose laurate yield up to61.35mg/mL. The process proposed couldmake it economically and environmentally feasible for large scale production. The neokestoselaurate was purified using C18solid phase extraction column. The structure of neokestoselaurate was determined by1H and13C NMR，COSY and HMQC, and the results showed thatthe novel chemical was6-O-laurylneokestose. Finally, CMC of6-O-laurylneokestose wasdetermined to be352μmol/L using Du Nouy plate method.
通过考察法夫酵母全细胞产新科斯糖的规律，确定其最佳产糖工艺条件。法夫酵母细胞在中性pH条件下显示了最佳的果糖苷酶活力；细胞浓度与新科斯糖产量非正相关，高浓度的细胞（>80g/L）会导致合成的新科斯糖水解；蔗糖浓度的增加可以显著增加新科斯糖产量，但同时会降低新科斯糖的生产效率；提高反应温度会显著增加法夫酵母细胞的果糖苷酶活力；细胞酶活特性与其种龄密切相关，指数生长期的细胞具有较高的果糖苷酶活力，稳定期的细胞具有较高的水解酶活力。在优化的工艺条件即：细胞种龄32h，浓度80g/L，蔗糖水溶液浓度400g/L，转化温度30℃，转化时间4h，新科斯糖产量可以达到227.72g/L。
根据法夫酵母可产虾青素作为高附加值产品的特点，优化了~6G-果糖苷酶和虾青素联产的培养基成分和发酵条件，以期降低新科斯糖的生产成本。单因素实验结果显示蔗糖和玉米浆是~6G-果糖苷酶和虾青素联产的最佳碳源和氮源；Plackett-Burman实验设计优化结果显示玉米浆和pH是影响~6G-果糖苷酶和虾青素联产的关键因素；中心组合实验结果显示玉米浆浓度为52.5mL/L，pH为7.9时，~6G-果糖苷酶和虾青素联产可以达到最佳产量，分别为242.57U/mL和5.23mg/L；在优化的培养条件下，采用全细胞生物转化工艺，新科斯糖的最大生产效率为119.06g/L/h，且成本分析显示培养基成本较优化前降低了66.3%。此研究进一步加速了新科斯糖的工业化生产进程。
通过模拟不同的杀菌热处理条件，研究了新科斯糖的酸热稳定性，结果表明：新科斯糖在中性和碱性环境下均非常稳定性，可耐受巴氏杀菌（85℃，60min），高温短时间（100℃，30min和121℃，20min）及超高温瞬时（135℃，30s）热处理。在酸性环境下，pH为2和3的新科斯糖溶液经85℃，30min热处理，保留率分别为42.04%和78.99%；pH为4的新科斯糖溶液经100℃，30min和121℃，20min热处理，保留率分别为97.08%和89.83%。运用DSC技术，研究了新科斯糖对大米淀粉糊化及老化性质的影响，结果显示：新科斯糖可以提高大米淀粉初始糊化温度，与低聚果糖，异麦芽糖及蔗糖相比，对初始糊化温度的增加程度大小顺序为：低聚果糖>新科斯糖>异麦芽糖>蔗糖；新科斯糖可以降低淀粉糊化焓值，降低程度与新科斯糖的加入量成正相关性。新科斯糖对淀粉老化行为影响结果表明：淀粉在4℃储藏时，低浓度（10%）新科斯糖在短期内（7天）和长期内（28天）均可以显著抑制淀粉的老化；而高浓度新科斯糖（30%）在长期内可以抑制淀粉老化。淀粉储藏在25℃时，低浓度（10%）的新科斯糖在长期内（28天）会抑制淀粉老化，其他情况下对淀粉老化行为影响效果不显著。与FOS，IMO相比，新科斯糖抗淀粉老化效果优于FOS和IMO。
采用月桂酸乙烯酯成功对新科斯糖进行了酰化改性，经LC-MS初步鉴定产物为新科斯糖月桂酸单酯。通过对新科斯糖月桂酸酯合成规律的考察，确定了最佳反应条件：反应体系为DMSO和2-甲基-2-丁醇（2：8；v/v），新科斯糖与月桂酸乙烯酯的分子摩尔比为1：12，反应温度为50℃，分子筛添加量为100g/L，Novozyme435添加量为10g/L，反应32h后，转化率达到82.38%。在对反应进程研究的基础上，制定了新科斯糖补料策略（每隔8h补新科斯糖0.01M），连续补加8次后，新科斯糖月桂酸酯的产量提高了4.47倍，达到61.35mg/mL。采用C18固相萃取色谱柱对合成的新科斯糖月桂酸酯进行了纯化，并采用1H和13C NMR，COSY和HMQC对合成的糖酯进行了结构鉴定，结果显示糖酯为新科斯糖-6-月桂酸酯。最后，采用Du Nouy吊片法测定了其CMC值，结果为352μmol/L。
Neokestose, a novel fructooligosaccharide (FOS), was reported to possess superiorprebiotic activity to commercial FOS. Such favorable functionalities may boost the marketdemand of neo-FOS. However, no commercial neo-FOS have been produced until now,mainly due to the high cost for their trace amount extraction from vegetables and fruits ortheir low microbial productivity via~6G-fructofuranosidase (~6G-FFase). The whole-cellbiotransformation process, and simultaneous production of~6G-FFase and astaxanthin byXanthophyllomyces dendrorhous were firstly developed to make neokestose practicallyfeasible for commercial production in the present study. Moreover, the properties for foodprocessing were investigated to provide theoretical guidance for the application in foodproduct. Finally, the neokestose was acylated to enlarge the application of this functionalfactor.
The effects of production parameters on the biotransformation of sucrose wereinvestigated to enhance the yield of neokestose by Xanthophyllomyces dendrorhous. Cellsshowed optimal~6G-FFase activity at neutral pH and the yield of neokestose showed nosignificant differences between buffer and buffer-free systems. Cell concentration (>80g/L)negatively affected the maximum neokestose yield. Sucrose concentration positivelyincreased the maximum yield of neokestose. Elevating the reaction temperature to30℃, theneokestose productivity increased1.85-fold compared with that at20℃. Meanwhile, cell ageof32h enabled the biotransformation of sucrose more efficiently. In addition, free cellsexhibited a higher productivity over immobilized cells. The maximum neokestoseconcentration finally reached227.72g/L from400g/L sucrose under the optimal conditions.
The effects of medium composition and culture conditions on the simultaneousproduction of~6G-FFase and astaxanthin were investigated to reduce the capital cost ofneokestose production by Xanthophyllomyces dendrorhous. The sucrose and corn steep liquor(CSL) were found to be the optimal carbon source and nitrogen source, respectively. CSL andinitial pH were selected as the critical factors using Plackett-Burman design. Maximum~6G-FFase242.57U/mL with5.23mg/L astaxanthin was obtained at CSL52.5mL/L and pH7.9by central composite design. Neokestose yield could reach238.12g/L under the optimizedmedium conditions. Cost analysis suggested66.3%of substrate cost was reduced comparedwith that before optimization. These results demonstrated that the optimized medium andculture conditions could significantly enhance the production of~6G-FFase and astaxanthinand remarkably decrease the substrate cost, which opened up possibilities to produceneokestose industrially.
The heat and pH stability of neokestose was evaluated compared with commercial FOS bysimulating different thermo sterilization. The results showed that neokestose at neutral andalkaline pH displayed high heat and pH stability during pasteurization (85℃,30min), hightemperature for short time sterilization (100℃,30min and121℃,20min) and ultra hightemperature sterilization (135℃,30s). The neokestose at pH2and pH3retained42.04%and78.99%during pasteurization (85℃,30min), indicating a significant degradation. Neokestoseat pH4retained97.08%and89.83%during high temperature short time sterilization (100℃,30min and121℃,20min), suggesting a relatively high stability compared to that of FOS. Onthe other hand, the effects of neokestose on the gelatinization and retrogradation of rice starchwere studied compared with FOS, IMO and sucrose using a differential scanning calorimetry(DSC), and the results suggested that the addition of neokestose could increase thegelatinization temperature of rice starch in the order of neokestose>FOS>IMO>sucrose, andreduce the gelatinization enthalpy which showed negatively correlation with the concentrationof neokestose. Moreover, the effect of neokestose on the retrogradation of rice starch wasevaluated. The results indicated that10%of neokestose could significantly retard theretrogradation of rice starch when stored at4℃for short term (7days) and long term (28days);30%of neokestose could inhibit the retrogradation of rice starch when stored at4℃for longterm (28days);10%of neokestose could retard the retrogradation of rice starch when stored at25℃for long term (28days),30%of neokestose had no significant effect on the retragradationof rice starch when stored at25℃. Furthermore, neokestose showed better inhibition effect onthe retrogradation of rice starch compared with that of FOS and IMO at the tested conditions.
An acylation modification of neokestose using Candida antarctica lipase B asbiocatalyst was investigated aiming to further broaden the potential application of neokestose.The process conditions were optimized, and the highest conversion rate of82.38%wasachieved under the optimized conditions:20%DMSO in2-methyl-2-butanol (v/v), molarratio of12(vinyl laurate to neokestose), temperature of50℃, molecular sieves of100g/L.Finally, a neokestose feeding strategy was developed based on the kinetics of neokestoseacylation, driving neokestose laurate yield up to61.35mg/mL. The process proposed couldmake it economically and environmentally feasible for large scale production. The neokestoselaurate was purified using C18solid phase extraction column. The structure of neokestoselaurate was determined by1H and13C NMR，COSY and HMQC, and the results showed thatthe novel chemical was6-O-laurylneokestose. Finally, CMC of6-O-laurylneokestose wasdetermined to be352μmol/L using Du Nouy plate method.
引文
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