中国水仙挥发性成分及影响因素分析
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摘要
本研究以中国水仙为主要试材,采用不同的测试条件分析了水仙花、叶片、组培苗挥发性成分的组成和变化,以及中国水仙干花精油和中国水仙干叶精油成分。研究了赤霉素对芳樟醇合成的影响,游离氨基酸、游离脂肪酸、可溶性糖的变化和挥发性物质的关系,探讨了β-葡萄糖苷酶和醇酰基转移酶对挥发性物质的影响。本文还分离了中国水仙花游离态和键合态挥发性成分,并对两者进行了比较。关于中国水仙挥发性成分对人体健康的影响,本文也有所涉及。因为醇酰基转移酶、芳樟醇合成酶分别与酯类合成、芳樟醇合成有关,最后,本研究试图对这两种酶的基因进行了克隆。主要研究结果如下：
1.用65μmPDMS/DVB萃取头、50/30μmDVB/CAR/PDMS萃取头、75μmCAR/PDMS萃取头、100μmPDMS萃取头在相同的外部条件下萃取了中国水仙的挥发性成分。各种萃取头所吸附的挥发性成分有所差异,但基本都能萃取到了E-罗勒烯、Z-罗勒烯、芳樟醇、乙酸苯甲酯、乙酸苯乙酯等主要成分。
2.在不同温度、采后不同天数、不同培养条件下,以及中国水仙花挥发性成分早、中、晚的日变化实验中,虽然所测成分种类和含量有一定差异,但主要成分都是罗勒烯、芳樟醇、乙酸苯甲酯、乙酸苯乙酯等。中国水仙的两个主要品种金盏银台和玉玲珑的挥发性成分类似,也包括罗勒烯、芳樟醇、乙酸苯甲酯、乙酸苯乙酯等。
3.中国水仙叶片中主要挥发性成分是Z-乙酸-3-己烯酯、E-罗勒烯、乙酸苯甲酯、Z-丁酸-3-己烯酯、乙酸苯丙酯等。
4.中国水仙干花精油主要成分是棕榈酸和亚油酸,中国水仙干叶精油主要成分是棕榈酸、植物醇、豆蔻酸、苯乙醛等。
5.在中国水仙鳞茎再生组培培养基中添加30mg/L、50mg/L、70mg/L浓度的赤霉素,以研究赤霉素对组培苗中芳樟醇合成的影响,结果显示三个浓度与对照组相比,均未检测到芳樟醇。
6.中国水仙花开放过程中苯丙氨酸的含量变化基本和主要酯类挥发性成分的变化呈正相关。油酸可能在初花期和盛花期用于合成挥发性物质；亚油酸含量从花蕾期到初花期是下降的,可能在此阶段通过一系列降解反应生成挥发性物质。葡萄糖含量从花蕾、初花、盛花逐渐上升,到盛花期达到最高,然后开始下降,有可能是从花蕾期到盛花期,中国水仙内源β-葡萄糖苷酶的活性逐渐升高,催化糖苷键的水解断裂,释放出葡萄糖,导致葡萄糖含量升高,风味物质也逐渐增多。
7.中国水仙内源β-葡萄糖苷酶、醇酰基转移酶活性与酯类物质和芳樟醇的含量呈现一定的相关性。外源β-葡萄糖苷酶能水解糖苷键,释放出与糖苷键结合的挥发性物质,如芳樟醇等。
8.利用Amberlite XAD-2树脂柱分离了中国水仙盛花粉末中的游离态和键合态挥发性成分,发现游离态成分比键合态成分多。用β-葡萄糖苷酶酶解键合态组分,发现酶解后键合态中出现了葡萄糖,而酶解前没有；果糖含量也比酶解前高；表明β-葡萄糖苷酶确实能水解糖苷键,使之生成单糖,并释放出与糖苷键结合的挥发性物质。但酶解后键合态中未出现芳樟醇,且基本没有与游离态中相同的成分,也没有出现大幅增加的成分。
9.在布置一定中国水仙花数量的房间里测试了中国水仙花香气成分对人体血压、心率和呼吸频率的影响。青年组在闻香一小时,测得血压下降最大,而中老年组闻香两小时,测定血压下降最大。这可能是由于青年人肺功能好,闻香时用力深呼吸,芳香化合物刺激机体产生相应的生物活性物质,使得心率变慢,血压下降,有效降低了心肌耗氧量。中老年人由于肺功能差,闻香时主要靠增加呼吸频率,导致心率有所增加,但差异无显著性。中国水仙花香能有助于降低人体血压。
10.醇酰基转移酶和芳樟醇合成酶分别是合成酯类和芳樟醇的关键酶。本研究尝试克隆醇酰基转移酶基因(AAT)和芳樟醇合成酶基因(LIS),得到的AAT克隆片段与文献中报道的AAT cDNA片段大小接近,但经过序列分析后,发现与已知的AAT基因没有相似性,不能确定所克隆片段是否就是AAT cDNA片段。所克隆的LIS片段经过序列分析后,发现与GenBank中已知的LIS基因相似性很低,但其氨基酸序列中含有LIS基因的保守区RR和DDXXD,有待于克隆出全长,并做功能分析后才能确证。
In this study, Narcissus tazetta var. chinensis was used as the main material. Different methods were adopted to analyse the composition and variations of volatile constituents in flowers, leaves and tissue-cultured plantlets and the chemical components of essential oil from dried flower and dried leaf. The impact of Gibberellic acid on the synthesis of linalool was studied, as well asβ-glucosidase and alcohol acyltransferase in essential oil. Connection among the changes of cotents of free amino acids, free fatty acids and soluble sugar and essential oil has been researched. Free and bound volatile components in Narcissus tazetta var. chinensis have also been isolated and compared. The effects of volatile constituents on human health have also been involved. Because alcohol acyltransferase and linalool synthase are related to synthesis of esters and linalool, auther attempted to clone genes involved in these enzymes. The main results are as follow:
1. Volatile constituents have been extracted by 65μm PDMS/DVB fibre,50/30μm DVB/CAR/PDMS fibre,75μm CAR/PDMS fibre, 100μm CAR/PDMS fibre under the same conditions. Volatile constituents extracted by each fibre are different, however, E-ocimene, Z-ocimene, linalool, benzyl acetate and phenyl acetate have been mostly absorded.
2. The main volatile constituents are ocimene, linalool, benzyl acetate, phenyl acetate at different temperatures, daily change and conditions, though the measured components are some differences in the type and content. Different varities "yulinlong" and "jinzhanyintai" have samilar volatile constituents.
3. The main volatile constituents in leaves of Narcissus tazetta var. chinensis are 3Z-hexen-1-ol, acetate,E-ocimene, benzyl acetate, Z-butyricacid-3-hexene esters, phenyl propyl.
4. The essential oil in dried flowers is palmitic acid and linoleic acid, while in dried leaves is palmitic acid, phytol, myristic acid and phenylacetaldehyde.
5. To study GA how to affect the synthesis of linalool, we added 30mg/L,50mg/L,70mg /L concentration of GA into the tissue culture medium. The results showed that linalool was not detected from the seedling growing in GA medium and control medium.
6. During flowering, it is positive correlation between changes of phenylalanine content and major esters of volatile components. From early opening to full opening, oleic acid may be used in the synthesis of volatile substances; linoleic acid decline from the flower bud to early flowering, and at this stage, the degradation reaction may produce a series of volatile substances. Glucose gradually rose to peak from the flower bud, first opening to full blooming, and then declined. Endogenousβ-glucosidase activity increased gradually from the bud stage to full bloom, catalytic glycosidic bonds hydrolysis fracture, releasing glucose, leading glucose levels increased and flavor compounds also gradually increased.
7. The activities of endogenousβ-glucosidase enzyme and alcohol acyl transferase had some correlation with the content of esters and linalool. Exogenousβ-glucosidase could release volatile substances such as linalool and so on, which could combine with glycosidic bonds by hydrolyzing it.
8. The free state and bonding state of volatile components of powder from full-bloom stage were separated through Amberlite XAD-2 resin column. We found that volatile components in free state were more than those in bonding state. Glucose was found when enzymatic hydrolyzing the bonding state of volatile components and the content of fructose was also higher, which showed thatβ-glucosidase could hydrolyze glycosidic bond to monosaccharide and release volatile substances that could combine with glycosidic bond. However, linalool was not found when the bonding state was enzymatic hydrolyzed and there were not the same and significantly increased components when comparing with the free state.
9. The effects of aroma constituents on human blood pressure, heart rate and respiratory rate have been tested in a laboratory with a certain amount Narcissus tazetta var. chinensis. Youth group has the greatest drop in blood pressure after smelled an hour, while middle-aged group has the greatest drop after two hours. This may be due to better lung function of young people. They took a deeper breath when the force smells, the aroma compounds to stimulate the body to produce the corresponding biologically active substance, making slow heart rate, blood pressure, reduce the myocardial oxygen consumption. As poor pulmonary function, the middle aged and old people mainly by increasing the time smelling breath rate, resulting in an increase in heart rate, but the difference was not significant. Narcissus tazetta var. chinensis can reduce normal blood pressure in people with borderline hypertension, heart rate and respiratory rate of performance for the double entry regulation.
10. Alcohol acyl transferase and linalool synthase are the key enzymes that are related to synthesis of esters and linalool. Alcohol acyl transferase gene (AAT) and linalool synthase gene (LIS) were cloned. The length of clone fragment of AAT obtained was close to those AAT cDNA reported in the literature, but sequence analysis showed that it didn't exhibit similarity with those genes in GenBank. It can't be confirmed whether the cloned fragment is the AAT cDNA fragments. After sequence analysis, result showed that the clone fragment of LIS exhibited very low similarity with those genes in GenBank, but it presented two typical conserved motifs of terpene synthase,i.e RR and DDXXD. It would be confirmed whether the clone fragment of LIS belong to LIS family after full length clone and functional analysis.
1.用65μmPDMS/DVB萃取头、50/30μmDVB/CAR/PDMS萃取头、75μmCAR/PDMS萃取头、100μmPDMS萃取头在相同的外部条件下萃取了中国水仙的挥发性成分。各种萃取头所吸附的挥发性成分有所差异,但基本都能萃取到了E-罗勒烯、Z-罗勒烯、芳樟醇、乙酸苯甲酯、乙酸苯乙酯等主要成分。
2.在不同温度、采后不同天数、不同培养条件下,以及中国水仙花挥发性成分早、中、晚的日变化实验中,虽然所测成分种类和含量有一定差异,但主要成分都是罗勒烯、芳樟醇、乙酸苯甲酯、乙酸苯乙酯等。中国水仙的两个主要品种金盏银台和玉玲珑的挥发性成分类似,也包括罗勒烯、芳樟醇、乙酸苯甲酯、乙酸苯乙酯等。
3.中国水仙叶片中主要挥发性成分是Z-乙酸-3-己烯酯、E-罗勒烯、乙酸苯甲酯、Z-丁酸-3-己烯酯、乙酸苯丙酯等。
4.中国水仙干花精油主要成分是棕榈酸和亚油酸,中国水仙干叶精油主要成分是棕榈酸、植物醇、豆蔻酸、苯乙醛等。
5.在中国水仙鳞茎再生组培培养基中添加30mg/L、50mg/L、70mg/L浓度的赤霉素,以研究赤霉素对组培苗中芳樟醇合成的影响,结果显示三个浓度与对照组相比,均未检测到芳樟醇。
6.中国水仙花开放过程中苯丙氨酸的含量变化基本和主要酯类挥发性成分的变化呈正相关。油酸可能在初花期和盛花期用于合成挥发性物质；亚油酸含量从花蕾期到初花期是下降的,可能在此阶段通过一系列降解反应生成挥发性物质。葡萄糖含量从花蕾、初花、盛花逐渐上升,到盛花期达到最高,然后开始下降,有可能是从花蕾期到盛花期,中国水仙内源β-葡萄糖苷酶的活性逐渐升高,催化糖苷键的水解断裂,释放出葡萄糖,导致葡萄糖含量升高,风味物质也逐渐增多。
7.中国水仙内源β-葡萄糖苷酶、醇酰基转移酶活性与酯类物质和芳樟醇的含量呈现一定的相关性。外源β-葡萄糖苷酶能水解糖苷键,释放出与糖苷键结合的挥发性物质,如芳樟醇等。
8.利用Amberlite XAD-2树脂柱分离了中国水仙盛花粉末中的游离态和键合态挥发性成分,发现游离态成分比键合态成分多。用β-葡萄糖苷酶酶解键合态组分,发现酶解后键合态中出现了葡萄糖,而酶解前没有；果糖含量也比酶解前高；表明β-葡萄糖苷酶确实能水解糖苷键,使之生成单糖,并释放出与糖苷键结合的挥发性物质。但酶解后键合态中未出现芳樟醇,且基本没有与游离态中相同的成分,也没有出现大幅增加的成分。
9.在布置一定中国水仙花数量的房间里测试了中国水仙花香气成分对人体血压、心率和呼吸频率的影响。青年组在闻香一小时,测得血压下降最大,而中老年组闻香两小时,测定血压下降最大。这可能是由于青年人肺功能好,闻香时用力深呼吸,芳香化合物刺激机体产生相应的生物活性物质,使得心率变慢,血压下降,有效降低了心肌耗氧量。中老年人由于肺功能差,闻香时主要靠增加呼吸频率,导致心率有所增加,但差异无显著性。中国水仙花香能有助于降低人体血压。
10.醇酰基转移酶和芳樟醇合成酶分别是合成酯类和芳樟醇的关键酶。本研究尝试克隆醇酰基转移酶基因(AAT)和芳樟醇合成酶基因(LIS),得到的AAT克隆片段与文献中报道的AAT cDNA片段大小接近,但经过序列分析后,发现与已知的AAT基因没有相似性,不能确定所克隆片段是否就是AAT cDNA片段。所克隆的LIS片段经过序列分析后,发现与GenBank中已知的LIS基因相似性很低,但其氨基酸序列中含有LIS基因的保守区RR和DDXXD,有待于克隆出全长,并做功能分析后才能确证。
In this study, Narcissus tazetta var. chinensis was used as the main material. Different methods were adopted to analyse the composition and variations of volatile constituents in flowers, leaves and tissue-cultured plantlets and the chemical components of essential oil from dried flower and dried leaf. The impact of Gibberellic acid on the synthesis of linalool was studied, as well asβ-glucosidase and alcohol acyltransferase in essential oil. Connection among the changes of cotents of free amino acids, free fatty acids and soluble sugar and essential oil has been researched. Free and bound volatile components in Narcissus tazetta var. chinensis have also been isolated and compared. The effects of volatile constituents on human health have also been involved. Because alcohol acyltransferase and linalool synthase are related to synthesis of esters and linalool, auther attempted to clone genes involved in these enzymes. The main results are as follow:
1. Volatile constituents have been extracted by 65μm PDMS/DVB fibre,50/30μm DVB/CAR/PDMS fibre,75μm CAR/PDMS fibre, 100μm CAR/PDMS fibre under the same conditions. Volatile constituents extracted by each fibre are different, however, E-ocimene, Z-ocimene, linalool, benzyl acetate and phenyl acetate have been mostly absorded.
2. The main volatile constituents are ocimene, linalool, benzyl acetate, phenyl acetate at different temperatures, daily change and conditions, though the measured components are some differences in the type and content. Different varities "yulinlong" and "jinzhanyintai" have samilar volatile constituents.
3. The main volatile constituents in leaves of Narcissus tazetta var. chinensis are 3Z-hexen-1-ol, acetate,E-ocimene, benzyl acetate, Z-butyricacid-3-hexene esters, phenyl propyl.
4. The essential oil in dried flowers is palmitic acid and linoleic acid, while in dried leaves is palmitic acid, phytol, myristic acid and phenylacetaldehyde.
5. To study GA how to affect the synthesis of linalool, we added 30mg/L,50mg/L,70mg /L concentration of GA into the tissue culture medium. The results showed that linalool was not detected from the seedling growing in GA medium and control medium.
6. During flowering, it is positive correlation between changes of phenylalanine content and major esters of volatile components. From early opening to full opening, oleic acid may be used in the synthesis of volatile substances; linoleic acid decline from the flower bud to early flowering, and at this stage, the degradation reaction may produce a series of volatile substances. Glucose gradually rose to peak from the flower bud, first opening to full blooming, and then declined. Endogenousβ-glucosidase activity increased gradually from the bud stage to full bloom, catalytic glycosidic bonds hydrolysis fracture, releasing glucose, leading glucose levels increased and flavor compounds also gradually increased.
7. The activities of endogenousβ-glucosidase enzyme and alcohol acyl transferase had some correlation with the content of esters and linalool. Exogenousβ-glucosidase could release volatile substances such as linalool and so on, which could combine with glycosidic bonds by hydrolyzing it.
8. The free state and bonding state of volatile components of powder from full-bloom stage were separated through Amberlite XAD-2 resin column. We found that volatile components in free state were more than those in bonding state. Glucose was found when enzymatic hydrolyzing the bonding state of volatile components and the content of fructose was also higher, which showed thatβ-glucosidase could hydrolyze glycosidic bond to monosaccharide and release volatile substances that could combine with glycosidic bond. However, linalool was not found when the bonding state was enzymatic hydrolyzed and there were not the same and significantly increased components when comparing with the free state.
9. The effects of aroma constituents on human blood pressure, heart rate and respiratory rate have been tested in a laboratory with a certain amount Narcissus tazetta var. chinensis. Youth group has the greatest drop in blood pressure after smelled an hour, while middle-aged group has the greatest drop after two hours. This may be due to better lung function of young people. They took a deeper breath when the force smells, the aroma compounds to stimulate the body to produce the corresponding biologically active substance, making slow heart rate, blood pressure, reduce the myocardial oxygen consumption. As poor pulmonary function, the middle aged and old people mainly by increasing the time smelling breath rate, resulting in an increase in heart rate, but the difference was not significant. Narcissus tazetta var. chinensis can reduce normal blood pressure in people with borderline hypertension, heart rate and respiratory rate of performance for the double entry regulation.
10. Alcohol acyl transferase and linalool synthase are the key enzymes that are related to synthesis of esters and linalool. Alcohol acyl transferase gene (AAT) and linalool synthase gene (LIS) were cloned. The length of clone fragment of AAT obtained was close to those AAT cDNA reported in the literature, but sequence analysis showed that it didn't exhibit similarity with those genes in GenBank. It can't be confirmed whether the cloned fragment is the AAT cDNA fragments. After sequence analysis, result showed that the clone fragment of LIS exhibited very low similarity with those genes in GenBank, but it presented two typical conserved motifs of terpene synthase,i.e RR and DDXXD. It would be confirmed whether the clone fragment of LIS belong to LIS family after full length clone and functional analysis.
引文
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