迷迭香主要活性成分的绿色分离技术及其应用研究
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摘要
迷迭香系唇形科,迷迭香属植物。提取可作为抗氧化剂及医药的中间体,其抗氧化剂具有稳定、高效、耐高温的特点,被广泛应用于加工食品、医药保健及化妆品等方面。迷迭香提取物作为天然抗氧化剂,其主要活性成分为迷迭香精油、迷迭香酸和鼠尾草酸。本文在制定迷迭香原料GAP质量标准并对所用原料进行检测的基础上,利用绿色分离技术从迷迭香中得到了以的三个主要天然活性成分为主的不同迷迭香提取物,并针对所得到提取物的特点进行相应产品开发利用的研究及产品的抗氧化、抗炎等效果的评价,为迷迭香抗氧化剂的生产和应用提供了重要的参考。本文主要结论如下：
1、本文制定迷迭香原料GAP质量标准,对迷迭香原料的目的有效成分、产地、物种鉴定、采收、气味、包装、运输、贮存、农药残留及重金属含量等方面进行了详细的设定。并对实验所采用的迷迭香原料进行了检验,结果表明：本实验所用原料中鼠尾草酸含量3.35%,迷迭香酸0.51%,迷迭香精油3.02%,未见重金属和农药残留超标现象,原料符合该GAP质量标准。
2、新鲜迷迭香采摘后在晾干过程中鼠尾草酸等抗氧化活性化合物极易被降解采用微波预处理方法可有效维持鼠尾草酸和迷迭香酸的含量,并且同时可以将精油成分在预处理过程提取出来,方法创新,此前尚无报道。经过微波提取精油后的迷迭香叶片,其中的三种主要抗氧化剂成分鼠尾草酸、鼠尾草酚和迷迭香酸,均能在较长贮存时间内维持在较高的含量水平。而未经任何预处理的迷迭香鲜叶采摘后放置保存,10～14天时,其中的鼠尾草酸及迷迭香酸含量均显著降低。可见,微波处理方法不仅提取精油时所需时间短、产率高,还可作为一种新鲜迷迭香作物贮存之前的预处理手段来使用。
3、采用实验提取的迷迭香精油为油相,以蔗糖脂肪酸酯为表面活性剂制备迷迭香精油纳米乳,其中迷迭香精油含量为20%,循环乳化时间为15mmin,匀质压力800bar,循环6次,得到的纳米乳平均粒径145.9nm,离心稳定性常数Ke为0.458,乳剂的稳定性较好。迷迭香精油纳米乳的抗炎和透皮后抗氧能力均好于迷迭香精油,且在0.005-0.4m1/L浓度之间对细胞无毒性作用。迷迭香精油纳米乳的制备提高了精油的利用效率,拓宽了迷迭香精油的应用范围。
4、实验进行了一种有效的方法从迷迭香中提取鼠尾草酸和迷迭香酸,并对迷迭香中鼠尾草酸和迷迭香酸进行超声提取的离子液体进行筛选。实验结果为[C8mim]Br为提取迷迭香中鼠尾草酸和迷迭香酸的提取效率最高的离子液体。同时也对离子液体超声提取迷迭香中鼠尾草酸和迷迭香酸的最优超声提取条件进行了研究。在优化条件后,能够得到比较满意的两种目标物质的提取效率。相对于其他的方法,超声提取的方法具有更高的提取效率,并且能够降低提取的时间。确定最优实验条件为[C8mim]Br浓度1.0mol/L、料液比1：20g/mL、浸泡时间2h、超声时间30mmin、超声功率200W、提取次数为2次。与传统提取方法相比,该方法从迷迭香中同时提取鼠尾草酸和迷迭香酸具有提取率高、提取时间短等特点。和常规溶剂乙醇相比较都有所提高。同时该方法也被证明为是有助于开发节约型资源、环境友好型的鼠尾草酸和迷迭香酸提取方法。
5、将微波预处理和利用离子液体超声提取得到的迷迭香三种活性成分迷迭香精油、迷迭香酸和鼠尾草酸添加到不饱和脂肪酸含量90%以上的对牡丹籽油中,考察了三种活性物质对牡丹籽油氧化稳定性的影响。结果表明这三种活性物质对油脂氧化具有不同程度的抑制作用,抗氧化能力由强到弱依次为：鼠尾草酸>迷迭香酸>迷迭香精油。鼠尾草酸能有效延长牡丹籽油的保质期,预防其酸败变质。
6、在得到迷迭香水提物和醇提物的基础上,选定水提物和醇提物10：1为最优的水溶性粉体配方。得到的水溶性粉体溶解性好,平均粒径为930nm,鼠尾草酸含量为0.7%。迷迭香水溶性粉具有较好的抗炎和抗氧化能力,灌喂15天考察小鼠体增重变化结果中显示,迷迭香水溶性粉体具有良好的降低小鼠体增重的效果,具有开发为减肥保健品的潜力。我们选定的迷迭香泡腾粉制备配方为：每100g泡腾粉中含迷迭香水溶性粉30g,柠檬酸27.5g,碳酸氢纳32.5g,乳糖10g。此配方制备的迷迭香泡腾粉溶解时限为20s,溶解后为稳定,澄清的淡黄色液体。迷迭香泡腾粉清除DPPH自由基的SC50值为4.64mg/ml抗氧化性好,应用前景较好。
7、迷迭香活性成分提取后的剩余物质经热化学转化进一步开发利用。转化过程中的致密成型操作优化后的工艺参数为：剩余物含水率为8-13%,控制成型温度在150-200-℃之间,在最优条件下,所得致密成型棒坯的出料速度为1.9-2.1kg/min,得到成型棒坯的密度高、表面无裂痕,无明显炭化,无喷料现象。迷迭香剩余物成型棒坯热解反应,生物质炭的得率为28%-32%,醋液得率为23%-30%,焦油得率为12%-17%。采用快速低温沉降法,分离热解后馏出液中的醋液和焦油,其优化后的工艺参数为：分离温度0-5℃,分离时间为5-8h,所得的焦油和醋液品质,高于常温下自然沉降法分离得到产品的品质。采用有机溶剂萃取干燥后的醋液,不但可以去除水分,还可以富集多酚类抗氧化物质,低功率萃取所得醋液,甲酸乙酯萃取效果最好,其自由基的清除能力和铁还原能力均与合成抗氧化剂BHA相当。通过多酚含量测定,抗氧化能力测试和气质化学组分分析得知,抗氧化能力与酚类化合物的含量成正相关性。
Rosmarinus officinalis, commonly known as rosemary, belongs to the family of Lamiaceae. It is commonly known as extractable antioxidants and pharmaceutical intermediates, which with advantages of high efficiency, stability, high temperature. It has been widely used in food processing, medicine and cosmetics researching and developing. As a natural antioxidant, main active ingredient of rosemary extract are:essential oils, rosmarinic acid and carnosic acid. This paper designs an rosemary raw material GAP quality standard and follows it during implementation then detecting, utilizes green seperation technology thus obtains three different mainly active natural extracts of rosemary, and evaluated the corresponding product research and product development and the utilization of anti-oxidation, anti-inflammatory effect, it provided an important reference for the production and application of rosemary antioxidant extract features.The main conclusions of this paper are as follows:
1、 This paper designs rosemary raw materials GAP standard, describes active extracts, origin, species identification, harvesting, odor, packaging, transportation, storage, pesticide residues and heavy metal content and other aspects exhaustively. Afterward rosemary raw material that used in the experiments is tested, the results show that:3.35%carnosic acid content, rosmarinic acid0.51%,3.02%rosemary essential oil, there are no heavy metals and pesticide residues exceeding the phenomenon, all raw materials meet the GAP quality standards.
2、 Antioxidant activity of compounds such as carnosic acid in fresh rosemary after the picking-drying process can easily be degraded, by microwave pretreatment method can effectively maintains carnosic acid and rosmarinic acid content, meanwhile essential oil components being extracted during pretreatment method innovation, which has not been reported previously. Rosemary leaves after essential oils extrating by microwave, three main antioxidants carnosic acid, carnosol and rosmarinic acid maintains higher levels of content and longer time of storage. However, content of carnosic acid and rosmarinic acid content are significantly reduced when after picking rosemary leaves that without any pretreatment during the storage of10to14days.Therefore, advantage of microwave processing method are not only shorter extrating time and high yield, but can also be an pretreatment in fresh rosemary storage before use.
3、Oil phase is extracted rosemary essential oils to the experiment, surfactant is sucrose fatty acid ester in the preparation of rosemary essential oil nanoemulsion, thereinto rosemary essential oil content of20%,15min cycle emulsified, homogeneous pressure800bar,6cycles, the average particle diameter of the nanoemulsion obtained145.9nm, centrifugal stability constant Ke of0.458, obtains the better stability of the emulsion. Anti-inflammatory and antioxidant capacity after transdermal rosemary essential oil nanoemulsion are better than the essential oils of rosemary, and between0.005-0.4ml/L concentration without toxic effects on cells. Preparation of rosemary essential oil nanoemulsion improves the efficiency of its usage and broadens the range of applications of rosemary essential oils.
4、The experiment has conducted an effective way of extracting carnosic acid and rosmarinic acid from rosemary, filter ionic liquid of ultrasonic extraction carnosic acid and rosmarinic acid from rosemary. The experimental results [C8mim] Br as highest extraction efficiency for extracting rosemary carnosic acid and rosmarinic acid ionic liquid. Meanwhile optimal ultrasonic extraction conditions of ionic liquid in carnosic acid and rosmarinic acid extraction has been studied. In optimal conditions, two extraction efficiency of the target substance has been relatively satisfied. Relative to the other methods, ultrasonic extraction method has higher extraction efficiency, and the extraction time has been reduced. Determine the optimal experimental conditions is [C8mim] Br concentration of1.0mol/L, the solid to liquid ratio of1:20g/mL, and soaking time of2h, ultrasonic time30min, ultrasonic power200W, extraction times2times. Compared with traditional methods, the method simultaneously extracting rosemary extract carnosic acid and rosmarinic acid shows features of higher of extraction rate and shorter extraction time. Compared with using conventional solvent ethanol the result is also being enhanced. Meanwhile, this method of camosic acid and rosmarinic acid extracting is also been shown to contribute to the development of saving resources, and friendly to environment.
5、Adds three active ingredients:rosemary essential oils, rosmarinic acid and carnosic acid which obtained by microwave pre-treatment and ionic liquid ultrasonic extraction into peony seed oil that unsaturated fatty acid content more than90%, oxidation stability of the three active substances has been studied. The result shows that the effects of these three active substances have inhibited lipid oxidation diffeently, antioxidant capacity from strong to weak are:carnosic acid> rosmarinic acid> rosemary essential oils. The carnosic acid can extend the shelf life of the peony seed oil effectively, and prevent rancidity deterioration.
6、Selected on the basis of rosemary aqueous extract and ethanol extract, aqueous extract and ethanol extract of10:1for the best water-soluble powder formulations. Good solubility of a water-soluble powder obtained, the average particle diameter of930nm, and the camosic acid content of0.7%. Rosemary water-soluble powder has a good anti-inflammatory and antioxidant capacity, feed with15days to examine mouse body weight change results rosemary water-soluble powder has the effect of lower body weight gain in mice, which has an potential for weight loss and health products development. The recipe of rosemary effervescent powder preparation this experiment are:rosemary water-soluble powder30g per100g, effervescent powder containing citric acid27.5g, sodium bicarbonate, sodium,32.5g, lactose10g. Dissolved time from this recipe prepared rosemary effervescent powder limit for20s, and dissolved for a stable, clear yellowish liquid, value of4.64mg/ml oxidation resistance in DPPH radical SC50elimination of rosemary effervescent powder is good, better application prospects.
7、The remaining part of extracted substances by thermochemical conversion can be used into further development and utilization. The dense forming operation in the transformation process optimized parameters are:speed of discharge residue moisture content of8-13%, control the molding temperature between150-200℃under optimal conditions, the resulting dense shaped rod blanks1.9-2.1kg/min, gets high density of the molded rod blanks, no cracks on the surface, no significant charring, no spray material phenomenon. In rosemary residue rod blanks pyrolysis forming reaction, carbon biomass is28%-32%, the vinegar liquid yield of23%to30%, the tar yield of12%-17%. Adopts rapid low-temperature deposition method, separation after pyrolysis distillate liquid vinegar and tar, the optimized process parameters are:a separation temperature0-5℃, the separation time of5-8h, the quality of resulting tar and vinegar are above the normal temperature of natural sedimentation isolated product. Using the vinegar from dried organic solvent extraction not only can remove moisture, but can be enriched polyphenol antioxidants also. Withing low-power extraction proceeds vinegar, ethyl formate meets the best extraction efficiency, which its radical scavenging and iron reducing power and synthetic antioxidants as quite as BHA. The analysis of measured test, temperament chemical component of antioxidant capacity, and polyphenol content showed that there is a positive correlation between the antioxidant capacity and phenolic compounds content.
1、本文制定迷迭香原料GAP质量标准,对迷迭香原料的目的有效成分、产地、物种鉴定、采收、气味、包装、运输、贮存、农药残留及重金属含量等方面进行了详细的设定。并对实验所采用的迷迭香原料进行了检验,结果表明：本实验所用原料中鼠尾草酸含量3.35%,迷迭香酸0.51%,迷迭香精油3.02%,未见重金属和农药残留超标现象,原料符合该GAP质量标准。
2、新鲜迷迭香采摘后在晾干过程中鼠尾草酸等抗氧化活性化合物极易被降解采用微波预处理方法可有效维持鼠尾草酸和迷迭香酸的含量,并且同时可以将精油成分在预处理过程提取出来,方法创新,此前尚无报道。经过微波提取精油后的迷迭香叶片,其中的三种主要抗氧化剂成分鼠尾草酸、鼠尾草酚和迷迭香酸,均能在较长贮存时间内维持在较高的含量水平。而未经任何预处理的迷迭香鲜叶采摘后放置保存,10～14天时,其中的鼠尾草酸及迷迭香酸含量均显著降低。可见,微波处理方法不仅提取精油时所需时间短、产率高,还可作为一种新鲜迷迭香作物贮存之前的预处理手段来使用。
3、采用实验提取的迷迭香精油为油相,以蔗糖脂肪酸酯为表面活性剂制备迷迭香精油纳米乳,其中迷迭香精油含量为20%,循环乳化时间为15mmin,匀质压力800bar,循环6次,得到的纳米乳平均粒径145.9nm,离心稳定性常数Ke为0.458,乳剂的稳定性较好。迷迭香精油纳米乳的抗炎和透皮后抗氧能力均好于迷迭香精油,且在0.005-0.4m1/L浓度之间对细胞无毒性作用。迷迭香精油纳米乳的制备提高了精油的利用效率,拓宽了迷迭香精油的应用范围。
4、实验进行了一种有效的方法从迷迭香中提取鼠尾草酸和迷迭香酸,并对迷迭香中鼠尾草酸和迷迭香酸进行超声提取的离子液体进行筛选。实验结果为[C8mim]Br为提取迷迭香中鼠尾草酸和迷迭香酸的提取效率最高的离子液体。同时也对离子液体超声提取迷迭香中鼠尾草酸和迷迭香酸的最优超声提取条件进行了研究。在优化条件后,能够得到比较满意的两种目标物质的提取效率。相对于其他的方法,超声提取的方法具有更高的提取效率,并且能够降低提取的时间。确定最优实验条件为[C8mim]Br浓度1.0mol/L、料液比1：20g/mL、浸泡时间2h、超声时间30mmin、超声功率200W、提取次数为2次。与传统提取方法相比,该方法从迷迭香中同时提取鼠尾草酸和迷迭香酸具有提取率高、提取时间短等特点。和常规溶剂乙醇相比较都有所提高。同时该方法也被证明为是有助于开发节约型资源、环境友好型的鼠尾草酸和迷迭香酸提取方法。
5、将微波预处理和利用离子液体超声提取得到的迷迭香三种活性成分迷迭香精油、迷迭香酸和鼠尾草酸添加到不饱和脂肪酸含量90%以上的对牡丹籽油中,考察了三种活性物质对牡丹籽油氧化稳定性的影响。结果表明这三种活性物质对油脂氧化具有不同程度的抑制作用,抗氧化能力由强到弱依次为：鼠尾草酸>迷迭香酸>迷迭香精油。鼠尾草酸能有效延长牡丹籽油的保质期,预防其酸败变质。
6、在得到迷迭香水提物和醇提物的基础上,选定水提物和醇提物10：1为最优的水溶性粉体配方。得到的水溶性粉体溶解性好,平均粒径为930nm,鼠尾草酸含量为0.7%。迷迭香水溶性粉具有较好的抗炎和抗氧化能力,灌喂15天考察小鼠体增重变化结果中显示,迷迭香水溶性粉体具有良好的降低小鼠体增重的效果,具有开发为减肥保健品的潜力。我们选定的迷迭香泡腾粉制备配方为：每100g泡腾粉中含迷迭香水溶性粉30g,柠檬酸27.5g,碳酸氢纳32.5g,乳糖10g。此配方制备的迷迭香泡腾粉溶解时限为20s,溶解后为稳定,澄清的淡黄色液体。迷迭香泡腾粉清除DPPH自由基的SC50值为4.64mg/ml抗氧化性好,应用前景较好。
7、迷迭香活性成分提取后的剩余物质经热化学转化进一步开发利用。转化过程中的致密成型操作优化后的工艺参数为：剩余物含水率为8-13%,控制成型温度在150-200-℃之间,在最优条件下,所得致密成型棒坯的出料速度为1.9-2.1kg/min,得到成型棒坯的密度高、表面无裂痕,无明显炭化,无喷料现象。迷迭香剩余物成型棒坯热解反应,生物质炭的得率为28%-32%,醋液得率为23%-30%,焦油得率为12%-17%。采用快速低温沉降法,分离热解后馏出液中的醋液和焦油,其优化后的工艺参数为：分离温度0-5℃,分离时间为5-8h,所得的焦油和醋液品质,高于常温下自然沉降法分离得到产品的品质。采用有机溶剂萃取干燥后的醋液,不但可以去除水分,还可以富集多酚类抗氧化物质,低功率萃取所得醋液,甲酸乙酯萃取效果最好,其自由基的清除能力和铁还原能力均与合成抗氧化剂BHA相当。通过多酚含量测定,抗氧化能力测试和气质化学组分分析得知,抗氧化能力与酚类化合物的含量成正相关性。
Rosmarinus officinalis, commonly known as rosemary, belongs to the family of Lamiaceae. It is commonly known as extractable antioxidants and pharmaceutical intermediates, which with advantages of high efficiency, stability, high temperature. It has been widely used in food processing, medicine and cosmetics researching and developing. As a natural antioxidant, main active ingredient of rosemary extract are:essential oils, rosmarinic acid and carnosic acid. This paper designs an rosemary raw material GAP quality standard and follows it during implementation then detecting, utilizes green seperation technology thus obtains three different mainly active natural extracts of rosemary, and evaluated the corresponding product research and product development and the utilization of anti-oxidation, anti-inflammatory effect, it provided an important reference for the production and application of rosemary antioxidant extract features.The main conclusions of this paper are as follows:
1、 This paper designs rosemary raw materials GAP standard, describes active extracts, origin, species identification, harvesting, odor, packaging, transportation, storage, pesticide residues and heavy metal content and other aspects exhaustively. Afterward rosemary raw material that used in the experiments is tested, the results show that:3.35%carnosic acid content, rosmarinic acid0.51%,3.02%rosemary essential oil, there are no heavy metals and pesticide residues exceeding the phenomenon, all raw materials meet the GAP quality standards.
2、 Antioxidant activity of compounds such as carnosic acid in fresh rosemary after the picking-drying process can easily be degraded, by microwave pretreatment method can effectively maintains carnosic acid and rosmarinic acid content, meanwhile essential oil components being extracted during pretreatment method innovation, which has not been reported previously. Rosemary leaves after essential oils extrating by microwave, three main antioxidants carnosic acid, carnosol and rosmarinic acid maintains higher levels of content and longer time of storage. However, content of carnosic acid and rosmarinic acid content are significantly reduced when after picking rosemary leaves that without any pretreatment during the storage of10to14days.Therefore, advantage of microwave processing method are not only shorter extrating time and high yield, but can also be an pretreatment in fresh rosemary storage before use.
3、Oil phase is extracted rosemary essential oils to the experiment, surfactant is sucrose fatty acid ester in the preparation of rosemary essential oil nanoemulsion, thereinto rosemary essential oil content of20%,15min cycle emulsified, homogeneous pressure800bar,6cycles, the average particle diameter of the nanoemulsion obtained145.9nm, centrifugal stability constant Ke of0.458, obtains the better stability of the emulsion. Anti-inflammatory and antioxidant capacity after transdermal rosemary essential oil nanoemulsion are better than the essential oils of rosemary, and between0.005-0.4ml/L concentration without toxic effects on cells. Preparation of rosemary essential oil nanoemulsion improves the efficiency of its usage and broadens the range of applications of rosemary essential oils.
4、The experiment has conducted an effective way of extracting carnosic acid and rosmarinic acid from rosemary, filter ionic liquid of ultrasonic extraction carnosic acid and rosmarinic acid from rosemary. The experimental results [C8mim] Br as highest extraction efficiency for extracting rosemary carnosic acid and rosmarinic acid ionic liquid. Meanwhile optimal ultrasonic extraction conditions of ionic liquid in carnosic acid and rosmarinic acid extraction has been studied. In optimal conditions, two extraction efficiency of the target substance has been relatively satisfied. Relative to the other methods, ultrasonic extraction method has higher extraction efficiency, and the extraction time has been reduced. Determine the optimal experimental conditions is [C8mim] Br concentration of1.0mol/L, the solid to liquid ratio of1:20g/mL, and soaking time of2h, ultrasonic time30min, ultrasonic power200W, extraction times2times. Compared with traditional methods, the method simultaneously extracting rosemary extract carnosic acid and rosmarinic acid shows features of higher of extraction rate and shorter extraction time. Compared with using conventional solvent ethanol the result is also being enhanced. Meanwhile, this method of camosic acid and rosmarinic acid extracting is also been shown to contribute to the development of saving resources, and friendly to environment.
5、Adds three active ingredients:rosemary essential oils, rosmarinic acid and carnosic acid which obtained by microwave pre-treatment and ionic liquid ultrasonic extraction into peony seed oil that unsaturated fatty acid content more than90%, oxidation stability of the three active substances has been studied. The result shows that the effects of these three active substances have inhibited lipid oxidation diffeently, antioxidant capacity from strong to weak are:carnosic acid> rosmarinic acid> rosemary essential oils. The carnosic acid can extend the shelf life of the peony seed oil effectively, and prevent rancidity deterioration.
6、Selected on the basis of rosemary aqueous extract and ethanol extract, aqueous extract and ethanol extract of10:1for the best water-soluble powder formulations. Good solubility of a water-soluble powder obtained, the average particle diameter of930nm, and the camosic acid content of0.7%. Rosemary water-soluble powder has a good anti-inflammatory and antioxidant capacity, feed with15days to examine mouse body weight change results rosemary water-soluble powder has the effect of lower body weight gain in mice, which has an potential for weight loss and health products development. The recipe of rosemary effervescent powder preparation this experiment are:rosemary water-soluble powder30g per100g, effervescent powder containing citric acid27.5g, sodium bicarbonate, sodium,32.5g, lactose10g. Dissolved time from this recipe prepared rosemary effervescent powder limit for20s, and dissolved for a stable, clear yellowish liquid, value of4.64mg/ml oxidation resistance in DPPH radical SC50elimination of rosemary effervescent powder is good, better application prospects.
7、The remaining part of extracted substances by thermochemical conversion can be used into further development and utilization. The dense forming operation in the transformation process optimized parameters are:speed of discharge residue moisture content of8-13%, control the molding temperature between150-200℃under optimal conditions, the resulting dense shaped rod blanks1.9-2.1kg/min, gets high density of the molded rod blanks, no cracks on the surface, no significant charring, no spray material phenomenon. In rosemary residue rod blanks pyrolysis forming reaction, carbon biomass is28%-32%, the vinegar liquid yield of23%to30%, the tar yield of12%-17%. Adopts rapid low-temperature deposition method, separation after pyrolysis distillate liquid vinegar and tar, the optimized process parameters are:a separation temperature0-5℃, the separation time of5-8h, the quality of resulting tar and vinegar are above the normal temperature of natural sedimentation isolated product. Using the vinegar from dried organic solvent extraction not only can remove moisture, but can be enriched polyphenol antioxidants also. Withing low-power extraction proceeds vinegar, ethyl formate meets the best extraction efficiency, which its radical scavenging and iron reducing power and synthetic antioxidants as quite as BHA. The analysis of measured test, temperament chemical component of antioxidant capacity, and polyphenol content showed that there is a positive correlation between the antioxidant capacity and phenolic compounds content.
引文
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