热反应肉味香精的香气形成途径及活性研究
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摘要
鳊鱼属于淡水鱼,因为具有土腥味和骨刺多的缺点,所以目前仅供鲜销,鲜有加工产品。鳊鱼鱼肉中蛋白质含量丰富,利用蛋白酶水解蛋白,作为Maillard(美拉德)反应基液,用于制备热反应香精,既可以提高鳊鱼的经济价值,又可以为我国淡水鱼加工提供新的技术手段；而对Maillard反应香精的风味分析和MRPs (Maillard反应产物,Maillard Reaction Products)的活性研究,可以为今后开发新的Maillard反应产品提供思路。
本研究首先通过选择合适的复配蛋白酶对鳊鱼蛋白进行酶解,接着添加葡萄糖,利用均匀设计的试验方法优化Maillard反应条件,制备具有肉香味的香精。Maillard反应肉味香精用SPME-GC-MS(固相微萃取-气相色谱-质谱联用)分析挥发性风味化合物,确定对肉香味有特殊贡献的特征化合物,并讨论其在Maillard反应过程中的形成途径。通过DPPH抑制法、超氧阴离子自由基清除法和ABTS法鉴定MRPs的抗氧化活性,并对MRPs的降血压活性进行了初步的研究。
实验结果表明：
(1)通过Box-Behnken响应面优化酶解实验参数,得到最优化酶解条件：温度51.5℃,时间5.7h,pH7.7,酶添加量0.80%,在此条件下实测水解度为79.58%(±0.20)与预测值79.46%非常接近,说明建立的回归方程可以较好地反映各因素对水解度的影响。
(2)利用均匀实验设计优化Maillard反应条件,通过回归方程的建立,确定最佳反应条件为：反应温度110℃,反应时间100min,反应pH8.5,葡萄糖添加量为2.5%。设计在此最佳条件下进行重复实验,得到的产品平均得分为3.47,与预测得分误差为0.86%,且在此条件下制备的Maillard反应产品具有浓郁的酱制肉香味。
(3)采用SPME-GC-MS检测技术对Maillard反应肉味香精的风味成分进行分析鉴定,共检测到74种化合物,主要是含氮、氧的杂环化合物和醛类化合物。研究发现吡嗪类(2,5-二甲基吡嗪、2,6-二甲基吡嗪)、呋喃类(2-戊基呋喃和5-羟基麦芽酚)以及一些醛类(3-甲基丁醛、2-甲基丁醛、己醛、壬醛和苯甲醛)和含硫化合物(二甲基二硫、二甲基三硫和2-己基噻吩)对构成肉香味有主要贡献。这些化合物在其它具有肉香味的产品中也都存在,因此以鳊鱼作为原料,可以制得具有浓郁肉香味的热反应香精。
(4)通过单一氨基酸与葡萄糖的Maillard模型反应研究挥发性风味化合物形成途径发现,氨基酸与葡萄糖参与反应形成的大多是饱和的醛、酮和醇类化合物,而在自制的Maillard反应肉味香精中检测到的不饱和醛、酮和醇类化合物可能来源于不饱和脂肪酸的降解。含氮、含硫杂环化合物的生成,主要是氨基酸降解生成的H2S和NH3的参与。呋喃、吡喃类化合物既可以通过脂肪酸的参与形成,也可以由氨基酸与葡萄糖反应生成,如2-戊基呋喃；此外,葡萄糖降解也可以生成对酱香有增效作用的产物,如5-羟基麦芽酚(2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮)。模型反应中没有检测到自制样品中的含硫化合物,这可能是由其它含硫氨基酸(胱氨酸或蛋氨酸)反应生成的。通过模型反应能够探讨自制肉味香精中主要香气成分的形成途径,这有助于产品风味的进一步改善。
(5)选择三种不同的抗氧化实验体系,以茶多酚和TBHQ作为对照品,考察MRPs的抗氧化能力,发现MRPs在不同稀释程度下表现出不同的抗氧化活性,并呈一定的浓度依赖关系。通过茶多酚和TBHQ作为对照品,以IC50作为评价指标,得出：在DPPH自由基体系中,1mLMRPs与0.28mg的茶多酚或0.32mg的TBHQ清除DPPH自由基的效果相同；在超氧阴离子自由基体系中,1mLMRPs与2.66mg的茶多酚或3.52mg的TBHQ清除O2-·自由基的效果相同；在ABTS方法中,1mL MRPs与0.09mg的茶多酚和0.20mg的TBHQ效果相同。通过以上三种方法得出MRPs具有较好的抗氧化能力(其中1mLMRPs可以由0.11g鳊鱼鱼肉制得)。
(6)在体外降血压活性实验中,MRPs对ACE的抑制作用也是明显的,且在一定范围内抑制率呈现浓度依赖关系,当MRPs添加量为10μl时,抑制率为57.53%,而继续加大添加量,抑制率变化不显著。
通过抗氧化活性实验和体外降血压活性实验发现,MRPs均有较好的抑制效果,且在一定浓度范围内呈现浓度依赖趋势,随MRPs的浓度增加,抑制率加强。目前,对于MRPs的抑制机理还没有一致的结论。一部分研究认为低分子挥发性化合物可以提供氢原子,因此使得MRPs表现出一定的抗氧化能力；此外,还有研究认为类黑精的金属螯合作用对抗氧化和降血压都有一定的作用效果。
Parabramis pekinensis is fresh-water fish, which has off-flavor and a lot of tiny bones. Parabramis pekinensis is only sold fresh currently, rarely processed products existed. Parabramis pekinens is rich in protein, protease hydrolyzed protein is used to prepare fish protein hydrolysate. The fish protein hydrolysate then is used in Maillard reaction to produce meat flavoring, which can not only enhance the economic value, but also provide a new technological method for our fresh-water fish processing. Analysis of the flavor of Maillard reaction flavoring and MRPs'(Maillard Reaction Products) functional properties could provide new idea to the development of Maillard reaction products.
Firstly, Parabramis pekinensis protein was hydrolyzed by selecting the appropriate protease enzyme. Then fish protein hydrolysate was added with glucose, using the Uniform Designs to optimize the Maillard reaction conditions and prepare flavoring which had meat flavor. Volatiles from meat flavoring were first investigated by solid phase microextraction (SPME) combined with gas chromatography and mass spectrometry (GC-MS). Then the characteristic compounds which contribute to meat flavor were determined, and the pathway of the formation of which was analyzed the combined with the model reaction. At last chose three methods, DPPH assay, superoxide anion scavenging and ABTS assay to study the antioxidant activity of MRPs, and did initially study of MRPs' antihypertensive activity.
The results show that:
(1) The optimum process parameters of the Parabramis pekinensis enzymatic hydrolysis were determined by Box-Behnken response surface methodology (RSM). The model equations were regard to the effects of temperature, time, pH and enzyme dosages on the DH. The temperature of 51.5℃, time of 5.7 h, pH 7.7 and enzyme dosage of 0.80% were found to be the optimum conditions to obtain a high degree of hydrolysis of 79.47%(with the model estimates a difference of±0.20) using Flavourzyme and Protamex.
(2) The Maillard reaction parameters were optimized by the method of Uniform Designs. Polynomial regression type's mathematical model of reaction system was constructed. The temperature of 110℃, time of 100min, pH of 8.5 and glucose to substrate level of 2.5% were found to be the optimum conditions to obtain a higher score of 3.47 with an error of 0.86% to the prediction score. Under these conditions, prepared sample had a full meat flavor.
(3) The volatile compounds which drived from Maillard reaction meat flavoring were identified by SPME-GC-MS. A total of 74 compounds were identified, among those, mostly are nitrogen-and oxygen-containing heterocyclic compounds and aldehyde compounds. The study found pyrazines (2,5-dimethylpyrazine,2,6-dimethylpyrazine), furans (2-pentylfuran and 5-hydroxy-maltol), a number of aldehydes (3-methybutanal,2-methybutanal, hexanal, nonanal and benzaldehyde) and sulfur-containing compounds (dimethyl disulfide, dimethyl trisulfide and 2-hexylthiophene) had a major contribution to meat flavor. Above compounds were identified in others meet products, so it is achievable that Parabramis pekinensis as a material to produce Maillard reaction meat flavoring.
(4) The analysis of the formation of some important flavor compounds which drived from Maillard model reaction samples found that mostly saturated aldehydes, ketones and alcohols compounds were identified in the model reaction samples. But some unsaturated aldehydes, ketones and alcohols compounds were identified in self-sample, it supposed that they were derived from the degradation of unsaturated fatty acids. Amino acid degradation products, such as H2S and NH3 could participate in the Maillard reaction to form the nitrogen-and sulfur-containing heterocyclic compounds. Furans and pyrans,such as 2-pentylfuran, could generate not only by Fatty acids degradation but also by the reaction of amino acids and glucose. In addition,5-hydroxy-maltol (2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one) which could enhance the sauce flavor was formed by glucose degradation. Three sulfur-containing compounds might come from other sulfur-containing amino acids,such as cysteine or methionine, because of they were not detected in the model reaction samples.
(5) Chose tea polyphenols and TBHQ as a reference substance in order to study on the MRPs'antioxidant capacity in three different anoxidant assays. It found that MRPs in different dilution level had different antioxidant activity and showed a certain degree of concentration-dependent relationship. Here are some results which obtained from three assays and chose IC50 as an evaluation index:In the DPPH assay, 1mL MRPs'effects equaled with 0.28mg tea polyphenols or 0.32mg TBHQ; In superoxide anion scavenging assay,1mL MRPs'effects equaled with 2.66mg tea polyphenols or 3.52mg TBHQ; In ABTS assay,1mL MRPs' effects equaled with 0.09mg of tea polyphenols or 0.20mg TBHQ. It believed that MRPs have good antioxidant activity. (1mL MRPs need 0.11g Parabramis pekinensis fish meal preparation).
(6) In vitro ACE inhibitory activity experiment, the results obtained from the inhibition of ACE were notable, and within a certain degree in a concentration-dependent relationship. When the MRPs were added 10μl, the inhibition ratio was highest of 57.53%. If continued increasing of concentration, the inhibition was hardly change.
In the antioxidant activity and in vitro ACE inhibitory activity experiments, MRPs all showed a good inhibitory effects, and within a certain degree in a concentration-dependent relationship. The inhibition ratio was increased with the increasing of MRPs'concentration. The mechanisms for the antioxidant activity and ACE inhibitory activity were not yet known. It could be thought that some lower molecular volatile compounds could provide hydrogen might have effects in antioxidation. On the other hand, melanoidins had antioxidant capacity and antioxidant activity might come from metal chelating properties..
本研究首先通过选择合适的复配蛋白酶对鳊鱼蛋白进行酶解,接着添加葡萄糖,利用均匀设计的试验方法优化Maillard反应条件,制备具有肉香味的香精。Maillard反应肉味香精用SPME-GC-MS(固相微萃取-气相色谱-质谱联用)分析挥发性风味化合物,确定对肉香味有特殊贡献的特征化合物,并讨论其在Maillard反应过程中的形成途径。通过DPPH抑制法、超氧阴离子自由基清除法和ABTS法鉴定MRPs的抗氧化活性,并对MRPs的降血压活性进行了初步的研究。
实验结果表明：
(1)通过Box-Behnken响应面优化酶解实验参数,得到最优化酶解条件：温度51.5℃,时间5.7h,pH7.7,酶添加量0.80%,在此条件下实测水解度为79.58%(±0.20)与预测值79.46%非常接近,说明建立的回归方程可以较好地反映各因素对水解度的影响。
(2)利用均匀实验设计优化Maillard反应条件,通过回归方程的建立,确定最佳反应条件为：反应温度110℃,反应时间100min,反应pH8.5,葡萄糖添加量为2.5%。设计在此最佳条件下进行重复实验,得到的产品平均得分为3.47,与预测得分误差为0.86%,且在此条件下制备的Maillard反应产品具有浓郁的酱制肉香味。
(3)采用SPME-GC-MS检测技术对Maillard反应肉味香精的风味成分进行分析鉴定,共检测到74种化合物,主要是含氮、氧的杂环化合物和醛类化合物。研究发现吡嗪类(2,5-二甲基吡嗪、2,6-二甲基吡嗪)、呋喃类(2-戊基呋喃和5-羟基麦芽酚)以及一些醛类(3-甲基丁醛、2-甲基丁醛、己醛、壬醛和苯甲醛)和含硫化合物(二甲基二硫、二甲基三硫和2-己基噻吩)对构成肉香味有主要贡献。这些化合物在其它具有肉香味的产品中也都存在,因此以鳊鱼作为原料,可以制得具有浓郁肉香味的热反应香精。
(4)通过单一氨基酸与葡萄糖的Maillard模型反应研究挥发性风味化合物形成途径发现,氨基酸与葡萄糖参与反应形成的大多是饱和的醛、酮和醇类化合物,而在自制的Maillard反应肉味香精中检测到的不饱和醛、酮和醇类化合物可能来源于不饱和脂肪酸的降解。含氮、含硫杂环化合物的生成,主要是氨基酸降解生成的H2S和NH3的参与。呋喃、吡喃类化合物既可以通过脂肪酸的参与形成,也可以由氨基酸与葡萄糖反应生成,如2-戊基呋喃；此外,葡萄糖降解也可以生成对酱香有增效作用的产物,如5-羟基麦芽酚(2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮)。模型反应中没有检测到自制样品中的含硫化合物,这可能是由其它含硫氨基酸(胱氨酸或蛋氨酸)反应生成的。通过模型反应能够探讨自制肉味香精中主要香气成分的形成途径,这有助于产品风味的进一步改善。
(5)选择三种不同的抗氧化实验体系,以茶多酚和TBHQ作为对照品,考察MRPs的抗氧化能力,发现MRPs在不同稀释程度下表现出不同的抗氧化活性,并呈一定的浓度依赖关系。通过茶多酚和TBHQ作为对照品,以IC50作为评价指标,得出：在DPPH自由基体系中,1mLMRPs与0.28mg的茶多酚或0.32mg的TBHQ清除DPPH自由基的效果相同；在超氧阴离子自由基体系中,1mLMRPs与2.66mg的茶多酚或3.52mg的TBHQ清除O2-·自由基的效果相同；在ABTS方法中,1mL MRPs与0.09mg的茶多酚和0.20mg的TBHQ效果相同。通过以上三种方法得出MRPs具有较好的抗氧化能力(其中1mLMRPs可以由0.11g鳊鱼鱼肉制得)。
(6)在体外降血压活性实验中,MRPs对ACE的抑制作用也是明显的,且在一定范围内抑制率呈现浓度依赖关系,当MRPs添加量为10μl时,抑制率为57.53%,而继续加大添加量,抑制率变化不显著。
通过抗氧化活性实验和体外降血压活性实验发现,MRPs均有较好的抑制效果,且在一定浓度范围内呈现浓度依赖趋势,随MRPs的浓度增加,抑制率加强。目前,对于MRPs的抑制机理还没有一致的结论。一部分研究认为低分子挥发性化合物可以提供氢原子,因此使得MRPs表现出一定的抗氧化能力；此外,还有研究认为类黑精的金属螯合作用对抗氧化和降血压都有一定的作用效果。
Parabramis pekinensis is fresh-water fish, which has off-flavor and a lot of tiny bones. Parabramis pekinensis is only sold fresh currently, rarely processed products existed. Parabramis pekinens is rich in protein, protease hydrolyzed protein is used to prepare fish protein hydrolysate. The fish protein hydrolysate then is used in Maillard reaction to produce meat flavoring, which can not only enhance the economic value, but also provide a new technological method for our fresh-water fish processing. Analysis of the flavor of Maillard reaction flavoring and MRPs'(Maillard Reaction Products) functional properties could provide new idea to the development of Maillard reaction products.
Firstly, Parabramis pekinensis protein was hydrolyzed by selecting the appropriate protease enzyme. Then fish protein hydrolysate was added with glucose, using the Uniform Designs to optimize the Maillard reaction conditions and prepare flavoring which had meat flavor. Volatiles from meat flavoring were first investigated by solid phase microextraction (SPME) combined with gas chromatography and mass spectrometry (GC-MS). Then the characteristic compounds which contribute to meat flavor were determined, and the pathway of the formation of which was analyzed the combined with the model reaction. At last chose three methods, DPPH assay, superoxide anion scavenging and ABTS assay to study the antioxidant activity of MRPs, and did initially study of MRPs' antihypertensive activity.
The results show that:
(1) The optimum process parameters of the Parabramis pekinensis enzymatic hydrolysis were determined by Box-Behnken response surface methodology (RSM). The model equations were regard to the effects of temperature, time, pH and enzyme dosages on the DH. The temperature of 51.5℃, time of 5.7 h, pH 7.7 and enzyme dosage of 0.80% were found to be the optimum conditions to obtain a high degree of hydrolysis of 79.47%(with the model estimates a difference of±0.20) using Flavourzyme and Protamex.
(2) The Maillard reaction parameters were optimized by the method of Uniform Designs. Polynomial regression type's mathematical model of reaction system was constructed. The temperature of 110℃, time of 100min, pH of 8.5 and glucose to substrate level of 2.5% were found to be the optimum conditions to obtain a higher score of 3.47 with an error of 0.86% to the prediction score. Under these conditions, prepared sample had a full meat flavor.
(3) The volatile compounds which drived from Maillard reaction meat flavoring were identified by SPME-GC-MS. A total of 74 compounds were identified, among those, mostly are nitrogen-and oxygen-containing heterocyclic compounds and aldehyde compounds. The study found pyrazines (2,5-dimethylpyrazine,2,6-dimethylpyrazine), furans (2-pentylfuran and 5-hydroxy-maltol), a number of aldehydes (3-methybutanal,2-methybutanal, hexanal, nonanal and benzaldehyde) and sulfur-containing compounds (dimethyl disulfide, dimethyl trisulfide and 2-hexylthiophene) had a major contribution to meat flavor. Above compounds were identified in others meet products, so it is achievable that Parabramis pekinensis as a material to produce Maillard reaction meat flavoring.
(4) The analysis of the formation of some important flavor compounds which drived from Maillard model reaction samples found that mostly saturated aldehydes, ketones and alcohols compounds were identified in the model reaction samples. But some unsaturated aldehydes, ketones and alcohols compounds were identified in self-sample, it supposed that they were derived from the degradation of unsaturated fatty acids. Amino acid degradation products, such as H2S and NH3 could participate in the Maillard reaction to form the nitrogen-and sulfur-containing heterocyclic compounds. Furans and pyrans,such as 2-pentylfuran, could generate not only by Fatty acids degradation but also by the reaction of amino acids and glucose. In addition,5-hydroxy-maltol (2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one) which could enhance the sauce flavor was formed by glucose degradation. Three sulfur-containing compounds might come from other sulfur-containing amino acids,such as cysteine or methionine, because of they were not detected in the model reaction samples.
(5) Chose tea polyphenols and TBHQ as a reference substance in order to study on the MRPs'antioxidant capacity in three different anoxidant assays. It found that MRPs in different dilution level had different antioxidant activity and showed a certain degree of concentration-dependent relationship. Here are some results which obtained from three assays and chose IC50 as an evaluation index:In the DPPH assay, 1mL MRPs'effects equaled with 0.28mg tea polyphenols or 0.32mg TBHQ; In superoxide anion scavenging assay,1mL MRPs'effects equaled with 2.66mg tea polyphenols or 3.52mg TBHQ; In ABTS assay,1mL MRPs' effects equaled with 0.09mg of tea polyphenols or 0.20mg TBHQ. It believed that MRPs have good antioxidant activity. (1mL MRPs need 0.11g Parabramis pekinensis fish meal preparation).
(6) In vitro ACE inhibitory activity experiment, the results obtained from the inhibition of ACE were notable, and within a certain degree in a concentration-dependent relationship. When the MRPs were added 10μl, the inhibition ratio was highest of 57.53%. If continued increasing of concentration, the inhibition was hardly change.
In the antioxidant activity and in vitro ACE inhibitory activity experiments, MRPs all showed a good inhibitory effects, and within a certain degree in a concentration-dependent relationship. The inhibition ratio was increased with the increasing of MRPs'concentration. The mechanisms for the antioxidant activity and ACE inhibitory activity were not yet known. It could be thought that some lower molecular volatile compounds could provide hydrogen might have effects in antioxidation. On the other hand, melanoidins had antioxidant capacity and antioxidant activity might come from metal chelating properties..
引文
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