CN101544991A - Natural antioxidant of perilla flavone for cigarette and method for preparing same - Google Patents
Natural antioxidant of perilla flavone for cigarette and method for preparing sameDownload PDFInfo
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Abstract
Translated fromChineseDescription
Translated fromChinese技术领域technical field
本发明涉及烟用添加剂技术领域，具体地说是一种天然烟用抗氧化剂—紫苏黄酮的提取制备方法。The invention relates to the technical field of tobacco additives, in particular to an extraction and preparation method of natural tobacco antioxidant-perilla flavone.
背景技术Background technique
在烟草制品中，既要保证烟气质量，又要保证卷烟的低危害性，在卷烟中添加烟用添加剂—抗氧化剂越来越受到重视。提取天然抗氧化剂进行烟用是减害降焦的一个重要方向，申请人正是沿着这个方向在进行探索。In tobacco products, it is necessary not only to ensure the quality of smoke, but also to ensure the low hazard of cigarettes. Adding tobacco additives-antioxidants to cigarettes has attracted more and more attention. Extracting natural antioxidants for tobacco use is an important direction for harm reduction and tar reduction, and the applicant is exploring along this direction.
紫苏叶为唇形科植物紫苏Perilla frutescens(L.)Britt.的叶，又称苏叶，具解表功能，为一年生草本植物。原产中国，如今主要分布于印度、缅甸、中国、日本、朝鲜、韩国、印度尼西亚和俄罗斯等国家。我国华北、华中、华南、西南及台湾省均有野生种和栽培种。紫苏在我国种植应用约有近2000年的历史，主要用于药用、油用、香料、食用等方面，其叶(苏叶)、梗(苏梗)、果(苏子)均可入药，嫩叶可生食、作汤，茎叶可淹渍。近些年来，紫苏因其特有的活性物质及营养成分，成为一种倍受世界关注的多用途植物，经济价值很高。俄罗斯、日本、韩国、美国、加拿大等国对紫苏属植物进行了大量的商业性栽种，开发出了食用油、药品、淹渍品、化妆品等几十种紫苏产品。现有技术中，但尚未有从紫苏中提取烟用添加剂的先例，而且，据申请人研究得知前述紫苏叶提取香油后的紫苏叶残渣中含有许多有用成分，都被作为废料处理掉了，尚未得到合理的利用。Perilla leaves are the leaves of Perilla frutescens (L.) Britt., a plant of the Labiatae family, also known as perilla leaves, which have the function of detoxification and are annual herb plants. Originally produced in China, it is now mainly distributed in countries such as India, Myanmar, China, Japan, North Korea, South Korea, Indonesia and Russia. There are wild species and cultivated species in North my country, Central China, South China, Southwest China and Taiwan Province. Perilla has been planted and used in my country for nearly 2,000 years. It is mainly used for medicine, oil, spices, food, etc. Its leaves (perilla leaves), stems (perilla stems) and fruits (perilla seeds) can be used as medicines. , the young leaves can be eaten raw and made into soup, and the stems and leaves can be soaked. In recent years, perilla has become a multi-purpose plant that has attracted worldwide attention due to its unique active substances and nutritional components, with high economic value. Russia, Japan, South Korea, the United States, Canada and other countries have carried out a large number of commercial plantings of perilla plants, and developed dozens of perilla products such as edible oils, medicines, soaked products, and cosmetics. In the prior art, there is no precedent for extracting tobacco additives from perilla, and according to the applicant's research, it is known that the residue of perilla leaves after extracting sesame oil from perilla leaves contains many useful components, which are all treated as waste Lost and not yet rationally utilized.
发明内容Contents of the invention
针对现有技术的上述不足，本发明要解决的技术问题是提供一种天然烟用抗氧化剂—紫苏黄酮及其制备方法，紫苏黄酮应用于卷烟中取得较好的抗氧化作用；本发明方法使作为废料的紫苏叶提取香油后的紫苏叶残渣得到合理的利用，且提取得率较高。Aiming at the above-mentioned deficiencies in the prior art, the technical problem to be solved in the present invention is to provide a natural tobacco antioxidant—perilla flavonoid and its preparation method. Perilla flavone is applied in cigarettes to obtain better antioxidant effect; the present invention The method makes rational use of perilla leaf residue after extracting sesame oil from perilla leaves as waste material, and the extraction yield is high.
本发明的技术方案是：天然烟用抗氧化剂—紫苏黄酮由以下方法制备而得：将紫苏叶提取挥发油后的残渣干燥后，用真空破膜、浸泡、复合酶促—乙醇回流提取、减压抽滤、低温高速离心后精制而得提取的紫苏黄酮提取液。The technical scheme of the present invention is: natural tobacco antioxidant-perilla flavone is prepared by the following method: after drying the residue after extracting volatile oil from perilla leaves, vacuum membrane rupture, soaking, compound enzymatic-ethanol reflux extraction, The extracted perilla flavonoids extract is obtained by vacuum filtration, low-temperature high-speed centrifugation and purification.
所述的复合酶为食品级固体粉末状纤维素酶、果胶酶、蛋白酶的组合酶。The compound enzyme is a combination enzyme of food-grade solid powder cellulase, pectinase and protease.
所述的复合酶由以下组份及份数组成：纤维素酶：果胶酶：蛋白酶＝0.5～2：0.5～2：0.5～2。The compound enzyme is composed of the following components and parts: cellulase: pectinase: protease = 0.5-2: 0.5-2: 0.5-2.
所述的真空破膜是指将紫苏叶提取挥发油后的残渣置于真空度98％下，抽真空2min，骤停，使紫苏细胞壁破膜。The vacuum rupture refers to placing the residue after extracting the volatile oil from perilla leaves under a vacuum degree of 98%, vacuuming for 2 minutes, and stopping suddenly, so that the perilla cell wall is ruptured.
天然烟用抗氧化剂-紫苏黄酮的制备方法按以下步骤进行：The preparation method of natural tobacco antioxidant-perilla flavone is carried out according to the following steps:
(1)原料处理：将提取挥发油后的紫苏叶残渣进行干燥后，装入抽真空装置，在真空度98％下，抽真空2min，骤停，进行真空破膜，使紫苏细胞壁破膜，然后粉碎得到紫苏叶残渣粗粉；(1) Raw material processing: After drying the perilla leaf residue after extracting the volatile oil, put it into a vacuum device, vacuumize for 2 minutes at a vacuum degree of 98%, stop suddenly, and perform vacuum rupture, so that the perilla cell wall is ruptured , and then pulverized to obtain perilla leaf residue coarse powder;
(2)浸泡和酶处理：取紫苏叶残渣粗粉放入容器，加入0.1～1％复合酶，5～10倍水混匀、调pH值4.0～6.0，40℃-50℃浸泡1h～2h；(2) Soaking and enzyme treatment: put the perilla leaf residue coarse powder into a container, add 0.1-1% compound enzyme, mix with 5-10 times of water, adjust the pH value to 4.0-6.0, soak at 40°C-50°C for 1h- 2h;
(3)提取精制：加入3～5倍95％乙醇，80℃～90℃水浴恒温回流提取1～2h，水泵抽真空减压抽滤、浓缩到原体积的1/4～1/5后，用8000～11000rpm高速离心分离，所得上清液即为紫苏黄酮提取液。(3) Extraction and refining: add 3 to 5 times of 95% ethanol, reflux in a water bath at 80°C to 90°C for 1 to 2 hours, pump vacuum and filter under reduced pressure, and concentrate to 1/4 to 1/5 of the original volume. 8000-11000rpm high-speed centrifugation is used, and the obtained supernatant is the perilla flavonoid extract.
所述的复合酶为食品级固体粉末状纤维素酶、果胶酶、蛋白酶。The compound enzyme is food-grade solid powdered cellulase, pectinase and protease.
所述的复合酶由以下组份及份数组成：纤维素酶：果胶酶：蛋白酶＝0.5～2：0.5～2：0.5～2。The compound enzyme is composed of the following components and parts: cellulase: pectinase: protease = 0.5-2: 0.5-2: 0.5-2.
本发明与现有技术比较具有以下优点：本发明的前处理采用了真空破膜和复合酶处理，更大程度地破坏了细胞壁结构，使有效成分更大程度暴露出来，降低滤渣的持水率，提高产率和降低提取成本，且真空破膜为物理方法、复合酶处理为生物方法，均安全、简便。本发明的提取物加入烟丝后不改变烟气质量。本发明所用的原料来源广泛，成本低，价值低廉；本发明的方法工艺过程简单易行，设备简单，提取物可作为新型天然烟用抗氧化剂。Compared with the prior art, the present invention has the following advantages: the pretreatment of the present invention adopts vacuum rupture and compound enzyme treatment, which destroys the cell wall structure to a greater extent, exposes the active ingredients to a greater extent, and reduces the water holding rate of the filter residue , increase the yield and reduce the extraction cost, and the vacuum membrane rupture is a physical method, and the compound enzyme treatment is a biological method, both of which are safe and convenient. The extract of the present invention does not change the smoke quality after being added to cut tobacco. The raw materials used in the invention have wide sources, low cost and low value; the method and process of the invention are simple and easy to implement, and the equipment is simple, and the extract can be used as a novel antioxidant for natural tobacco.
具体实施方式Detailed ways
下面对本发明的有关技术问题作进一步详细的描述。本申请人将本发明方法提取的紫苏黄酮提取液，与不经过破膜处理直接用乙醇溶剂提取的紫苏黄酮提取液的收率进行了比较，黄酮的含量采取紫外分光光度法测定。The related technical problems of the present invention will be further described in detail below. The applicant compared the yield of the perilla flavonoid extract extracted by the method of the present invention with the perilla flavone extract extracted directly with ethanol solvent without membrane breaking treatment, and the flavonoid content was measured by ultraviolet spectrophotometry.
1、标准曲线的制备1. Preparation of standard curve
准确称取芦丁标准品0.0501g，用30％乙醇溶解，并完全移入500ml容量瓶中，用30％乙醇定容。分别取芦丁标准溶液0、1、2、4、6、8、10ml于7只25ml容量瓶中，用30％乙醇补充至15ml，加入5％的亚硝酸钠0.7ml，摇匀，放置5min后加入10％硝酸铝0.7ml，6min后再加入4％的氢氧化钠5ml，混匀，用30％乙醇稀释至刻度，10min后于波长510nm处比色测定，空白为芦丁0ml标准液。测得吸光度A与浓度C mg/ml的标准曲线回归方程为：C＝0.10016A，R2＝0.99951。Accurately weigh 0.0501g of rutin standard substance, dissolve it with 30% ethanol, and completely transfer it into a 500ml volumetric flask, and dilute to volume with 30% ethanol. Take rutin standard solution 0, 1, 2, 4, 6, 8, 10ml respectively in seven 25ml volumetric flasks, supplement to 15ml with 30% ethanol, add 0.7ml of 5% sodium nitrite, shake well, and place for 5min Then add 0.7ml of 10% aluminum nitrate, and then add 5ml of 4% sodium hydroxide after 6 minutes, mix well, dilute to the mark with 30% ethanol, measure colorimetrically at the wavelength of 510nm after 10 minutes, and the blank is rutin 0ml standard solution. The standard curve regression equation of measured absorbance A and concentration C mg/ml is: C=0.10016A, R2=0.99951.
2、黄酮含量的测定2. Determination of flavonoid content
分光光度法：采用亚硝酸钠—硝酸铝比色法。Spectrophotometry: using sodium nitrite-aluminum nitrate colorimetric method.
分别取提取液各0.2ml于5只25ml容量瓶中，用30％乙醇补充至15ml，加入5％的亚硝酸钠0.7ml，摇匀，放置5min后加入10％硝酸铝0.7ml，6min后再加入4％的氢氧化钠5ml，混匀，用30％乙醇稀释至刻度，10min后于波长510nm处比色测定，记录吸光值在0—1.0以内为有效。Take 0.2ml of each extract in five 25ml volumetric flasks, add 30% ethanol to 15ml, add 0.7ml of 5% sodium nitrite, shake well, add 0.7ml of 10% aluminum nitrate after standing for 5min, and then add 0.7ml of 10% aluminum nitrate after 6min Add 5ml of 4% sodium hydroxide, mix well, dilute to the mark with 30% ethanol, measure colorimetrically at a wavelength of 510nm after 10 minutes, and record the absorbance value within 0-1.0 as valid.
3、试验结果3. Test results
测得经本发明真空破膜、复合酶促—溶剂提取的紫苏黄酮提取液，与直接溶剂提取(对照)的紫苏黄酮提取液吸光值后，由回归方程计算后所得数值即是黄酮的含量。原料为提取挥发油后的紫苏叶残渣粗粉10g，提取液定容到500ml，两种方法所得黄酮含量比较见表1。After measuring the perilla flavone extract through vacuum rupture of the present invention, compound enzymatic-solvent extraction, and the perilla flavone extract of direct solvent extraction (contrast), the obtained value after the regression equation calculation is the value of flavone. content. The raw material is 10 g of perilla leaf residue coarse powder after extracting volatile oil, and the extract is adjusted to 500 ml. The flavonoid content obtained by the two methods is compared in Table 1.
表1 提取液的黄酮含量对照Table 1 Control of flavonoid content in extract
本发明所采用的原料为紫苏叶提取挥发油后的残渣，价格低廉。本发明的提取方法比不经真空破膜、不加酶直接溶剂提取方法，所得的紫苏黄酮的收率明显提高，提高了提取效率，降低了生产成本，且真空破膜、加复合酶方法简便、易操作。The raw material used in the invention is the residue after extracting the volatile oil from perilla leaves, and the price is low. Compared with the direct solvent extraction method without vacuum rupture and enzyme addition, the extraction method of the present invention significantly improves the yield of perilla flavonoids, improves extraction efficiency, and reduces production costs. Simple and easy to operate.
本申请人还进行了紫苏黄酮提取液的抗氧化性测定，测定采取邻二氮菲体系羟基自由基清除实验。The applicant has also carried out the determination of the antioxidant activity of perilla flavonoid extract, and the determination adopts the hydroxyl radical scavenging experiment of the o-phenanthroline system.
1、取1ml 0.75mmol/L邻二氮菲无水乙醇溶液于试管中依次加入2ml、0.15mol/L的磷酸盐缓冲液(PBS，pH＝7.2)和1ml蒸馏水，充分混匀，加入1ml新配制的0.75mmol/L硫酸亚铁溶液，混匀后，加入1ml新配制的0.01％双氧水，于37℃水浴加热1h后，在536nm测吸光值，所测得的数据为吸光值A0。以1ml蒸馏水代替1ml 0.01％双氧水，操作方法与上述相同，可测得536nm时的吸光值A1，以A0为空白。以1ml样品代替1ml 0.01％双氧水，操作方法与上述相同，可测得536nm时的吸光值A2，以A0为空白。1. Take 1ml of 0.75mmol/L o-phenanthroline anhydrous ethanol solution, add 2ml, 0.15mol/L phosphate buffer saline (PBS, pH=7.2) and 1ml of distilled water in turn in the test tube, mix well, add 1ml of new After mixing the prepared 0.75mmol/L ferrous sulfate solution, add 1ml of newly prepared 0.01% hydrogen peroxide, heat in a water bath at 37°C for 1 hour, and measure the absorbance at 536nm. The measured data is the absorbance A0. Replace 1ml of 0.01% hydrogen peroxide with 1ml of distilled water. The operation method is the same as above, and the absorbance value A1 at 536nm can be measured, and A0 is used as a blank. Replace 1ml of 0.01% hydrogen peroxide with 1ml of sample, the operation method is the same as above, and the absorbance value A2 at 536nm can be measured, and A0 is used as the blank.
清除率(％)＝A2/A1×100％Clearance rate (%) = A2/A1 × 100%
2、配制0.1、0.125、0.15、0.175、0.20mg/ml的紫苏黄酮提取液和抗坏血酸(Vc)溶液，加入邻二氮菲羟自由基主生体系中，对不同浓度的紫苏黄酮提取液和抗坏血酸(Vc)清除体系中羟基自由基的效率进行检测，对羟基自由基的清除率比较如表2。2. Prepare 0.1, 0.125, 0.15, 0.175, 0.20 mg/ml of perilla flavone extract and ascorbic acid (Vc) solution, add o-phenanthroline hydroxyl radical main raw system, to different concentrations of perilla flavone extract and ascorbic acid (Vc) to detect the efficiency of hydroxyl radicals in the scavenging system, and compare the scavenging rates of hydroxyl radicals in Table 2.
表2 不同浓度紫苏黄酮提取液和Vc对邻二氮菲体系自由基清除对照Table 2 Free radical scavenging control of different concentrations of perilla flavonoids extract and Vc on o-phenanthroline
本发明方法用紫苏叶残渣得到的紫苏黄酮提取液，对邻二氮菲体系产生的羟基自由基有一定的清除作用，在0.175mg/ml时，清除率达到58.87％；在相同浓度下，本发明的紫苏黄酮提取液清除能力是天然抗氧化剂抗坏血酸(Vc)的5～10倍，在一定范围内，随着浓度增加，清除能力还逐步增强。The perilla flavonoid extract obtained by the method of the present invention with the perilla leaf residue has a certain scavenging effect on the hydroxyl radicals produced by the o-phenanthroline system, and the scavenging rate reaches 58.87% at 0.175 mg/ml; at the same concentration , the scavenging ability of the perilla flavone extract of the present invention is 5 to 10 times that of the natural antioxidant ascorbic acid (Vc), within a certain range, with the increase of the concentration, the scavenging ability is also gradually enhanced.
将本发明的紫苏黄酮提取液，按1％、0.5％、0.1％(质量百分比)加入到烟丝中，烘干并卷制成卷烟(按现有技术中的有关规定进行评吸，以武汉烟草集团有限公司，红金龙某二类烟为对照，进行感官评吸和烟气气相自由基测定。The perilla flavonoid extract of the present invention is added in shredded tobacco by 1%, 0.5%, 0.1% (mass percentage), dried and rolled into cigarettes (evaluated and smoked according to the relevant regulations in the prior art, taking Wuhan Tobacco Group Co., Ltd., a second-class cigarette of Hongjinlong was used as a control, and the sensory evaluation and gas-phase free radical determination of the smoke were carried out.
1、感官评吸1. Sensory evaluation
经武烟评吸专家组评吸，与空白对照相比，烟丝中添加紫苏叶残渣黄酮提取液后，不改变烟气质量。According to the evaluation by the Wuhan Tobacco Smoking Expert Group, compared with the blank control, adding perilla leaf residue flavonoid extract to shredded tobacco does not change the smoke quality.
2、烟气气相自由基测定2. Determination of gas phase free radicals in flue gas
取平均单支重0.920g±0.02g和平均吸阻1.065kPa±0.05kPa的卷烟各20支作为试验样品。制备的试验卷烟均放入恒温恒湿箱内于温度22℃±2℃和相对湿度60％±2％的环境中平衡水分48h。采用电子自旋共振法(ESR)进行烟气气相自由基检测，结果见表3。Take 20 cigarettes each with an average single weight of 0.920g±0.02g and an average draw resistance of 1.065kPa±0.05kPa as test samples. The prepared test cigarettes were all placed in a constant temperature and humidity chamber to balance the moisture for 48 hours in an environment with a temperature of 22°C±2°C and a relative humidity of 60%±2%. Electron spin resonance (ESR) was used to detect gas phase free radicals in flue gas, and the results are shown in Table 3.
表3 紫苏叶残渣黄酮提取液加烟清除烟气自由基实验Table 3 Experiment of removing free radicals in smoke by adding flavonoid extract from perilla leaf residue
测定结果显示，与对照相比，加入紫苏黄酮提取液的卷烟烟气自由基浓度有一定的降低；且在一定范围内，随着紫苏黄酮提取液浓度的增加，清除率提高。The measurement results showed that, compared with the control, the concentration of free radicals in cigarette smoke added with perilla flavone extract decreased to a certain extent; and within a certain range, with the increase of perilla flavone extract concentration, the clearance rate increased.
本申请人对本发明方法制备的紫苏黄酮提取液的稳定性进行了实验。其一是温度稳定性实验。将含量为0.175mg/ml的紫苏黄酮提取液在90℃下保温12h，或在60℃下保温24h后，测定其黄酮含量和邻二氮菲体系羟基自由基清除率，结果见表4。The applicant conducted experiments on the stability of the perilla flavone extract prepared by the method of the present invention. One is the temperature stability experiment. The perilla flavonoid extract with a content of 0.175mg/ml was incubated at 90°C for 12h, or at 60°C for 24h, then the flavonoid content and the hydroxyl radical scavenging rate of the phenanthroline system were measured. The results are shown in Table 4.
表4、温度稳定性测定Table 4. Determination of temperature stability
由上表可知，紫苏黄酮提取液经60℃保温24h后稳定性较好，与加热前相比黄酮含量只略降低了0.02mg/ml，其邻二氮菲体系羟基自由基清除率降低了12.66％；而90℃保温12h的样品结果显示在此温度下热稳定性较差，黄酮含量降低了一半，邻二氮菲体系羟基自由基清除率只有约5％。但在卷烟加工中，黄酮提取液加入烟丝后，遇到的高温只可能在天气、室温影响范围内，在制丝工艺加香时也不可能持续长时间高温，所以紫苏叶残渣黄酮提取液的烟用热稳定性良好。其二是进行了溶液pH梯度稳定性实验。将浓度为0.175mg/ml的紫苏黄酮提取液在pH2、4、6、8、10时，测定黄酮含量、邻二氮菲体系羟基自由基清除率，结果见表5。It can be seen from the above table that the perilla flavone extract has good stability after being incubated at 60°C for 24 hours, and the flavonoid content is only slightly reduced by 0.02mg/ml compared with that before heating, and the hydroxyl radical scavenging rate of the ortho-phenanthroline system is reduced. 12.66%; and the results of the samples incubated at 90°C for 12 hours showed that the thermal stability was poor at this temperature, the flavonoid content was reduced by half, and the hydroxyl radical scavenging rate of the o-phenanthroline system was only about 5%. However, in cigarette processing, after the flavonoid extract is added to shredded tobacco, the high temperature encountered can only be within the influence of weather and room temperature, and it is impossible to sustain high temperature for a long time when adding flavor in the silk making process, so the flavonoid extract from perilla leaf residue The smoke has good thermal stability. The second is to carry out the solution pH gradient stability experiment. The perilla flavone extract with a concentration of 0.175 mg/ml was used to measure the flavonoid content and the hydroxyl radical scavenging rate of the phenanthroline system at pH 2, 4, 6, 8, and 10. The results are shown in Table 5.
表5、溶液pH梯度稳定性Table 5, solution pH gradient stability
由上表可知，紫苏黄酮提取液，在pH4～6范围内稳定性良好，其黄酮含量基本不变，邻二氮菲体系羟基自由基清除率基本不变。而烟丝的pH值也偏酸性，在pH5～6左右，因此紫苏黄酮提取液的活性pH值适合烟用。It can be seen from the above table that the perilla flavonoid extract has good stability in the range of pH 4-6, the flavonoid content is basically unchanged, and the hydroxyl radical scavenging rate of the phenanthroline system is basically unchanged. And the pH value of shredded tobacco is also slightly acidic, about pH 5-6, so the active pH value of perilla flavone extract is suitable for smoking.
本申请人进行了烟气气相自由基测定The applicant has carried out the determination of free radicals in the gas phase of flue gas
取平均单支重0.920g±0.02g和平均吸阻1.065kPa±0.05kPa的卷烟各20支作为试验样品。制备的试验卷烟均放入恒温恒湿箱内于温度22℃±2℃和相对湿度60％±2％的环境中平衡水分48h。采用电子自旋共振法(ESR)进行烟气气相自由基检测，结果见表6。Take 20 cigarettes each with an average single weight of 0.920g±0.02g and an average draw resistance of 1.065kPa±0.05kPa as test samples. The prepared test cigarettes were all placed in a constant temperature and humidity chamber to balance the moisture for 48 hours in an environment with a temperature of 22°C±2°C and a relative humidity of 60%±2%. Electron spin resonance (ESR) was used to detect gas phase free radicals in flue gas, and the results are shown in Table 6.
表6 加入紫苏黄酮提取液卷烟清除烟气自由基实验Table 6 Adding perilla flavonoids extract to remove free radicals from cigarette smoke
上表测定结果显示，与对照样相比，加入紫苏黄酮提取液的卷烟烟气自由基浓度有一定的降低；且在一定范围内，随着提取液浓度的增加，清除率提高。The measurement results in the above table show that compared with the control sample, the concentration of free radicals in cigarette smoke added with perilla flavonoid extract has a certain decrease; and within a certain range, with the increase of the concentration of the extract, the clearance rate increases.
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