竹红菌素的特性及应用研究
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摘要
竹红菌素是一类天然脂溶性苝醌色素,是我国传统中药竹黄子座中的主要活性成分,其色泽鲜红、着色力好,具有作为食用天然色素应用于食品领域的巨大潜力。本文系统研究了竹红菌素的稳定性和抑菌活性,提出了利用羟丙基-β-环糊精包埋来增强竹红菌素水溶性的新方法,并探讨了竹红菌素对蛋黄的着色性能,以期通过本论文的研究为今后竹红菌素在食品中的应用提供基础依据。
论文通过单因素实验确定竹黄子座中竹红菌素的提取工艺为1g竹黄子座粉末加入30mL无水乙醇,60℃冷凝回流浸提2h,在此工艺下竹红菌素的提取量为4.45mg/g。提取物中共含有3种色素成分,其中含量最大的是竹红菌乙素,含量约67%,其次是竹红菌甲素(约25%)和竹红菌丙素(约8%)。
竹红菌素对体系pH值较为敏感,pH<8.0时竹红菌素呈亮红色,具有优良的热稳定性和光稳定性,pH>10.0时竹红菌素呈亮绿色,热稳定性和光稳定性均降低;Mg~(2+),Pb~(2+),Mn~(2+),Ca~(2+)对竹红菌素的稳定性没有明显影响,Zn~(2+)和Na+对竹红菌素具有一定的增色作用,Fe~(2+),Fe~(3+),Cu~(2+)和Al~(3+)对竹红菌素的稳定性影响较大,会导致竹红菌素颜色的明显变化;竹红菌素对氧化剂过氧化氢和还原剂焦亚硫酸钠有很好的耐受性,对常见食品添加剂抗坏血酸、山梨酸钾、苯甲酸钠、葡萄糖、蔗糖和柠檬酸均具有较好的稳定性,但对还原剂亚硫酸钠非常敏感;竹红菌素在避光条件下对油脂的氧化稳定性没有明显影响,但高浓度的竹红菌素在光照条件下会造成油脂氧化稳定性下降,因此竹红菌素用作油脂着色剂时需避光保藏或控制添加浓度。
竹红菌素对革兰氏阳性菌具有良好的光敏抑菌活性,对革兰氏阴性菌抑菌作用不明显;光照时间和氧气对竹红菌素的光敏抑菌活性有重要影响,热处理对抑菌活性无明显影响;酸性环境或者加入Ca~(2+)、Mg~(2+)可使竹红菌素对革兰氏阴性菌也产生较好的抑菌作用;竹红菌素与菌体呈松散结合,竹红菌素的光敏抑菌反应同时包括Type I和Type II两类机制;研究认为竹红菌素的抑菌机理是其光敏产生的活性氧对菌体的细胞壁和细胞膜造成损伤,膜通透性增强,胞内物质泄漏,最终导致菌体死亡。
在蛋鸡日粮中添加竹红菌素粗提物后,竹红菌素可以有效沉积在蛋黄中,明显加深蛋黄颜色;随着添加量增大和饲喂时间延长,蛋黄中竹红菌素沉积量增大,对蛋黄着色效果增强;停止添加后蛋黄中竹红菌素沉积量迅速降低,失去对蛋黄的着色效果;添加竹红菌素在加深蛋黄颜色的同时不会对鸡蛋的其它品质指标、功能性质和储藏性能产生不利影响,不会影响蛋鸡的生产性能;竹红菌素在蛋鸡的卵巢和肝脏中沉积量较高,并且随着添加量增大沉积量逐渐增大,在心、肺、胃和肌肉组织中沉积量较低,且不受添加量变化影响。
竹红菌素与羟丙基-β-环糊精可以以1:1的摩尔比形成可溶性包合物,包合反应为放热反应,主要由焓驱动,包合反应过程中体系的焓值、熵值和自由能均降低;通过吸收光谱、荧光光谱、红外光谱和热分析结果的相互印证证实了包合物的形成,并推测是竹红菌素的芳香环结构进入了羟丙基-β-环糊精的空腔;包合物的形成可以明显提高竹红菌素的水溶性和热分解起始温度。
Hypocrellins are main active components in Shiraia bambusicola which had been used as an orally taken folk medicine for several centuries in China. Hypocrellins are naturally occurring hydrophobic perylenequinone pigments with bright red color and excellent tinting strength. It has great potential to be used as natural colorant in food industry. The stabilities and antimicrobial activities of hypocrellins were studied in this research. Hypocrellin/HP-β-CD inclusion complex was prepared in order to improve the water solubility of hypocrellin. The effect of dietary hypocrellins supplementation on egg quality and functional properties are also investigated. The dissertation is a fundamental research for application of hypocrellins in food industry.
The parameters of extracting process were obtained by the monofactrorial tests. The optimal parameters were 1 gram of material powder immersed in 30 mL absolute ethanol at 60℃for 2h. The extracting rate of hypocrellins under these parameters was 4.45mg/g dry material. There are 3 main pigment components in hypocrellins extract. The major components was hypocrellin B (67%), followed by hypocrellin A (～25%) and hypocrellin C (～8%).
Value of pH was a significant factor on the stabilities of hypocrellins. Hypocrellins has bright red color with excellent stabilities to heat and irradiation in acidic circumstances. The color of hypocrellin turned to green and the stabilities to heat and light were decreased in alkaline conditions. Metal ions such as Mg~(2+),Pb~(2+),Mn~(2+) , Ca~(2+) hardly affect the stabilities of hypocrellins. Zn~(2+) and Na+ had copigmentation effect on hypocrellins. Fe~(2+), Fe~(3+), Al~(3+) and Cu~(2+) could affect the color and stabilities of hypocrelins. Hypocrellins were resistant to hydrogen peroxide and soium pyrosulfite, but was sensitive to sodium sulfite. No significant influences of food additives in common use, such as ascorbic acid, sodium benzoate, potassium sorbate, cane sugar, glucose and citric acid, on the stabilities of pigment were observed. The oxidative stability of vegetable oil was not affected by hypocrellins in dark place. Hige dose of hypocrellins will decrease the oxidative stability of vegetable oil under illumination. Therefore, when hypocrellins were used as oil colorants, the products should be stored in dark place.
Hypocrellins possessed excellent photodynamic antimicrobial activities against Gram-positive bacteria, however, the antimicrobial activities against Gram-negative bacteria were not obvious. The irradiation time and oxygen play important roles in the antimicrobial activities of hypocrellins. Antimicrobial activities of hypocrellins against both Gram-positive and Gram-negative microorganisms were enhanced when Ca~(2+) or Mg~(2+) was employed or in acidic circumstances. A loose binding has been established between hypocrellins and the organisms. Hypocrellins maintains a photodynamic activity in terms of both types I and II reactions. The ractive oxygen speices produce by hypocrellins could cause the injuries of cell wall and membrane. The permeability of membrane was enhanced. Consequently, the leakage of intracellular contents appeared to be the major cause of microorganism inactivation upon photodynamic antimicrobial process of hypocrellins.
Hypocrellins supplementation of poultry feed significantly improve the color of egg yolk and increase the concentration of hypocrellins deposited in egg yolk. The content of hypocrellins deposited in egg yolk increased with the increasing of feed time and hypocrellins dosages added to the diet. The content of hypocrellins deposited in egg yolk decreased sharply when the layers were feed by basal diet. Besides egg yolk color, short-term hypocrellins supplementations of poultry diet dose not influence the productive performance of layers and qulity, functional properties and strorage stabilities of eggs. The highest hypocrellins content in tissues samples was measured in ovary, followed by liver. The hypocrellins contents in heart, lung, gizzard and breast muscles were much lower. Moreover, hypocrellins content in ovary and liver were increased significantly with the increasing of hypocrellin added to the diet. By contrast, no significant differences of hypocrellins content in heart, lung, gizzard and breast muscle were observed in all supplementation diet groups.
Hypocrellins and HP-β-CD can form inclusion complex with possible stoichiometry of 1:1. The inclusion process was an exothermic and enthalpy-driven process accompanied with a negative entropic contribution. FT-IR, DSC, TG and spectroscopic studies comfirm the formation of inclusion complex and presume that the aroma rings of hypocrellins were embedded in the cavity of HP-β-CD. The formation of inclusion complex can significantly increase the solubility and the thermal decomposition start temperature.
论文通过单因素实验确定竹黄子座中竹红菌素的提取工艺为1g竹黄子座粉末加入30mL无水乙醇,60℃冷凝回流浸提2h,在此工艺下竹红菌素的提取量为4.45mg/g。提取物中共含有3种色素成分,其中含量最大的是竹红菌乙素,含量约67%,其次是竹红菌甲素(约25%)和竹红菌丙素(约8%)。
竹红菌素对体系pH值较为敏感,pH<8.0时竹红菌素呈亮红色,具有优良的热稳定性和光稳定性,pH>10.0时竹红菌素呈亮绿色,热稳定性和光稳定性均降低;Mg~(2+),Pb~(2+),Mn~(2+),Ca~(2+)对竹红菌素的稳定性没有明显影响,Zn~(2+)和Na+对竹红菌素具有一定的增色作用,Fe~(2+),Fe~(3+),Cu~(2+)和Al~(3+)对竹红菌素的稳定性影响较大,会导致竹红菌素颜色的明显变化;竹红菌素对氧化剂过氧化氢和还原剂焦亚硫酸钠有很好的耐受性,对常见食品添加剂抗坏血酸、山梨酸钾、苯甲酸钠、葡萄糖、蔗糖和柠檬酸均具有较好的稳定性,但对还原剂亚硫酸钠非常敏感;竹红菌素在避光条件下对油脂的氧化稳定性没有明显影响,但高浓度的竹红菌素在光照条件下会造成油脂氧化稳定性下降,因此竹红菌素用作油脂着色剂时需避光保藏或控制添加浓度。
竹红菌素对革兰氏阳性菌具有良好的光敏抑菌活性,对革兰氏阴性菌抑菌作用不明显;光照时间和氧气对竹红菌素的光敏抑菌活性有重要影响,热处理对抑菌活性无明显影响;酸性环境或者加入Ca~(2+)、Mg~(2+)可使竹红菌素对革兰氏阴性菌也产生较好的抑菌作用;竹红菌素与菌体呈松散结合,竹红菌素的光敏抑菌反应同时包括Type I和Type II两类机制;研究认为竹红菌素的抑菌机理是其光敏产生的活性氧对菌体的细胞壁和细胞膜造成损伤,膜通透性增强,胞内物质泄漏,最终导致菌体死亡。
在蛋鸡日粮中添加竹红菌素粗提物后,竹红菌素可以有效沉积在蛋黄中,明显加深蛋黄颜色;随着添加量增大和饲喂时间延长,蛋黄中竹红菌素沉积量增大,对蛋黄着色效果增强;停止添加后蛋黄中竹红菌素沉积量迅速降低,失去对蛋黄的着色效果;添加竹红菌素在加深蛋黄颜色的同时不会对鸡蛋的其它品质指标、功能性质和储藏性能产生不利影响,不会影响蛋鸡的生产性能;竹红菌素在蛋鸡的卵巢和肝脏中沉积量较高,并且随着添加量增大沉积量逐渐增大,在心、肺、胃和肌肉组织中沉积量较低,且不受添加量变化影响。
竹红菌素与羟丙基-β-环糊精可以以1:1的摩尔比形成可溶性包合物,包合反应为放热反应,主要由焓驱动,包合反应过程中体系的焓值、熵值和自由能均降低;通过吸收光谱、荧光光谱、红外光谱和热分析结果的相互印证证实了包合物的形成,并推测是竹红菌素的芳香环结构进入了羟丙基-β-环糊精的空腔;包合物的形成可以明显提高竹红菌素的水溶性和热分解起始温度。
Hypocrellins are main active components in Shiraia bambusicola which had been used as an orally taken folk medicine for several centuries in China. Hypocrellins are naturally occurring hydrophobic perylenequinone pigments with bright red color and excellent tinting strength. It has great potential to be used as natural colorant in food industry. The stabilities and antimicrobial activities of hypocrellins were studied in this research. Hypocrellin/HP-β-CD inclusion complex was prepared in order to improve the water solubility of hypocrellin. The effect of dietary hypocrellins supplementation on egg quality and functional properties are also investigated. The dissertation is a fundamental research for application of hypocrellins in food industry.
The parameters of extracting process were obtained by the monofactrorial tests. The optimal parameters were 1 gram of material powder immersed in 30 mL absolute ethanol at 60℃for 2h. The extracting rate of hypocrellins under these parameters was 4.45mg/g dry material. There are 3 main pigment components in hypocrellins extract. The major components was hypocrellin B (67%), followed by hypocrellin A (～25%) and hypocrellin C (～8%).
Value of pH was a significant factor on the stabilities of hypocrellins. Hypocrellins has bright red color with excellent stabilities to heat and irradiation in acidic circumstances. The color of hypocrellin turned to green and the stabilities to heat and light were decreased in alkaline conditions. Metal ions such as Mg~(2+),Pb~(2+),Mn~(2+) , Ca~(2+) hardly affect the stabilities of hypocrellins. Zn~(2+) and Na+ had copigmentation effect on hypocrellins. Fe~(2+), Fe~(3+), Al~(3+) and Cu~(2+) could affect the color and stabilities of hypocrelins. Hypocrellins were resistant to hydrogen peroxide and soium pyrosulfite, but was sensitive to sodium sulfite. No significant influences of food additives in common use, such as ascorbic acid, sodium benzoate, potassium sorbate, cane sugar, glucose and citric acid, on the stabilities of pigment were observed. The oxidative stability of vegetable oil was not affected by hypocrellins in dark place. Hige dose of hypocrellins will decrease the oxidative stability of vegetable oil under illumination. Therefore, when hypocrellins were used as oil colorants, the products should be stored in dark place.
Hypocrellins possessed excellent photodynamic antimicrobial activities against Gram-positive bacteria, however, the antimicrobial activities against Gram-negative bacteria were not obvious. The irradiation time and oxygen play important roles in the antimicrobial activities of hypocrellins. Antimicrobial activities of hypocrellins against both Gram-positive and Gram-negative microorganisms were enhanced when Ca~(2+) or Mg~(2+) was employed or in acidic circumstances. A loose binding has been established between hypocrellins and the organisms. Hypocrellins maintains a photodynamic activity in terms of both types I and II reactions. The ractive oxygen speices produce by hypocrellins could cause the injuries of cell wall and membrane. The permeability of membrane was enhanced. Consequently, the leakage of intracellular contents appeared to be the major cause of microorganism inactivation upon photodynamic antimicrobial process of hypocrellins.
Hypocrellins supplementation of poultry feed significantly improve the color of egg yolk and increase the concentration of hypocrellins deposited in egg yolk. The content of hypocrellins deposited in egg yolk increased with the increasing of feed time and hypocrellins dosages added to the diet. The content of hypocrellins deposited in egg yolk decreased sharply when the layers were feed by basal diet. Besides egg yolk color, short-term hypocrellins supplementations of poultry diet dose not influence the productive performance of layers and qulity, functional properties and strorage stabilities of eggs. The highest hypocrellins content in tissues samples was measured in ovary, followed by liver. The hypocrellins contents in heart, lung, gizzard and breast muscles were much lower. Moreover, hypocrellins content in ovary and liver were increased significantly with the increasing of hypocrellin added to the diet. By contrast, no significant differences of hypocrellins content in heart, lung, gizzard and breast muscle were observed in all supplementation diet groups.
Hypocrellins and HP-β-CD can form inclusion complex with possible stoichiometry of 1:1. The inclusion process was an exothermic and enthalpy-driven process accompanied with a negative entropic contribution. FT-IR, DSC, TG and spectroscopic studies comfirm the formation of inclusion complex and presume that the aroma rings of hypocrellins were embedded in the cavity of HP-β-CD. The formation of inclusion complex can significantly increase the solubility and the thermal decomposition start temperature.
引文
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