艾纳香叶中左旋龙脑与精油的制备及其抗氧化与抗菌活性研究
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摘要
艾纳香（Blumea balsamifera（L.）DC.）为菊科艾纳香属植物，是著名的少数民族香料，也是中药材，贵州罗甸县为其道地产地。《中国药典》记载艾纳香叶可用来制取艾片，即左旋龙脑，在贵州地区已有百年历史。早期使用土法制备艾片，以作坊式生产为主；随着技术进步，提取设备有所改进，但是存在提取率低、得率低、产品质量差的缺陷。本课题根据左旋龙脑理化特征，设计简单且高效的高纯度左旋龙脑制备工艺，在提取左旋龙脑的同时收集精油，并对其成分含量和活性进行分析评价。主要结果如下：
1.原料采收期与活性成分的关系研究
为掌握合适的原料采收期，更好的安排生产，快速测定原料中左旋龙脑含量成为第一目标。通过优化六种预处理方法，即水蒸气蒸馏-溶剂萃取法（Hydrodistillation-solventextraction，HDSE）、同时蒸馏萃取法（Simultaneous distillation extraction，SDE）、溶剂浸提法（Solvent extraction，SE）、超声辅助提取法（Ultrasonic-assisted extraction，UAE）、微波辅助提取法（Microwave-assisted extraction，MAE）、超声-微波协同萃取法（Ultrasonic-microwave assisted extraction，UMAE），获得各方法的最佳提取条件。方法学验证结果证实同时测定艾纳香叶中左旋龙脑、樟脑和异龙脑时，只有HDSE-GC的回收率满足需要（100%-105%）；若仅测定左旋龙脑，UMAE-GC的回收率为87%，满足测定需要。比较六种方法的时间、能量、溶剂消耗后发现，消耗最少的方法是UMAE，微波功率100W，提取时间30s，可作为快速测定艾纳香叶中左旋龙脑的预处理方法。最终，测定14个来自采收期的艾纳香叶样品，发现10月15日至次年1月15日采收的艾纳香叶中左旋龙脑含量较高，适合作为生产左旋龙脑的原料。
2.左旋龙脑分离纯化及结构鉴定
比较不同提取方法的得率和效率后发现垂直冷凝收集法是最佳提取方法，最佳条件为料水比1:50（g：mL），蒸馏时间30min，左旋龙脑得率达到0.85%（干物质），提取率达到93%，粗提物中左旋龙脑含量达到81%。在120℃下升华30min可制得左旋龙脑含量为91%的艾片，得率为0.83%（干物质）。以艾片为基料，再利用简单的重结晶法可制得高纯度左旋龙脑（含量>98%），多次反复重结晶可使左旋龙脑的总回收率达82%，最终得率为0.75%（干物质），此过程简单，易操作，成本低，适合用于高纯度左旋龙脑的纯化制备。经旋光性和核磁共振分析证实纯化制得左旋龙脑确实是左旋龙脑。
3.艾纳香精油提取工艺研究
使用顶空固相微萃取（Headspace-solid phase microextraction，HS-SPME）收集艾纳香叶的香气组分；水蒸气蒸馏-溶剂萃取法（HDSE）和同时蒸馏萃取法（SDE）收集的挥发油得率分别为1.00%和0.98%；水蒸气蒸馏-挤压法（Hydrodistillation-extrusion，HDE）收集的精油得率最低，仅为0.19%；本文设计两步水蒸气蒸馏法（Two stephydrodistillation，TSHD）收集的精油得率较HDE精油高，为0.32%。香气主要含倍半萜类；HDSE挥发油、SDE挥发油与HDE精油组分相似，单萜类含量较高；TSHD精油与其他油差异较大，主要含倍半萜类化合物。
4.左旋龙脑和艾纳香精油的抗氧化与抑菌活性
左旋龙脑未表现出明显的、有价值的抗氧化活性。在挥发油和精油中，SDE挥发油具有最好的清除DPPH自由基的能力（IC50:10.07mg·mL~(-1)），HDSE挥发油在抑制β-胡萝卜素氧化中表现最好（IC50:2.45mg·mL~(-1)），TSHD精油在TBARS实验中表现活性最高，最适合在类生命体环境中发挥抗氧化活性。纯化左旋龙脑与标准品表现出一致的抑菌活性，对六种受试细菌的MIC值均为1mg·mL~(-1)，对红色毛癣菌的抑制活性更强（MIC值为0.13mg·mL~(-1)）。HDSE挥发油、SDE挥发油、HDE精油对受试细菌和真菌都表现出抑菌活性，对真菌的抑制能力强于细菌。TSHD精油对抑制受试细菌表现较差，对受试真菌抑制活性较其他三种油更出色，说明TSHD精油更适合用于抗真菌。
5.左旋龙脑对细菌细胞壁膜的影响
利用左旋龙脑处理大肠杆菌和金黄色葡萄球菌，观察其生长曲线的变化，绘制杀菌曲线，通过DiBAC4(3)和PI两染色剂观察细胞的膜电位和膜完整性的变化。结果显示左旋龙脑致细菌细胞死亡时，并未破坏其细胞壁膜的完整性，表现为膜电位改变，细胞去极化，膜的离子通道被影响，最终致其死亡。
Blumea balsamifera (L.) DC.(Asteraceae) is rich in terpenes and flavonoids and is afamous national spice and traditional Chinese medicine from Luodian County in China.Chinese Pharmacopoeia records that B. balsamifera is an important plant source of “Aipian”,natural (–)-borneol. The preparation of “Aipian” has last for over hundreds years in Guizhou,China.
“Aipian” was prepared using the general hydrodistillation at a workshop in early period.With the continual progress of technology, the improvements (automation reconstruction)have been made in the production. However, there still are defects remaining in the process,such as low extraction rate, low yield, poor product quality, etc. Based on the previous workand physicochemical properties of L-borneol, a simple and high efficient preparation processwas designed to prepare high-purity L-borneol and obtain essential oil. The yields, chemicalcompositions, and functional activities of L-borneol and essential oil were studied. Results ofthis study are as follows:
1. Relationship between raw material harvest period and active ingredient
To monitor the variation of material quality during harvest season and to arrangeproduction, the rapid determination of L-borneol in B. balsamifera leaves is indispensable.Six pretreatment methods were optimized to obtain the optimum extraction condition of eachmethod, including hydrodistillation-solvent extraction (HDSE), simultaneous distillationextraction (SDE), solvent extraction (SE), ultrasonic assisted extraction (UAE), microwaveassisted extraction (MAE), and ultrasonic-microwave assisted extraction (UMAE). Methodvalidation confirmed that the recovery of HDSE was the only one, which reached theaccuracy of simultaneous determination of L-borneol, camphor, and isoborneol in leaves, andthe values were between100%-105%. Furthermore, in the determination, the recovery ofL-borneol by UMAE was87%and met the criteria of determination. By comparison in time,energy, and solvent consumption, the consumption of UMAE was the lowest, microwavepower of100W, extraction time of30s, and UMAE was considered as the fastestpretreatment. Finally, fourteen batches of B. balsamifera leaves were determined byHDSE-GC and UMAE-GC, and the leaves harvested from October15to next January15hadhigher L-borneol content and were suitable as material.
2. Isolation, purification, and identification of L-borneol
By comparison in the yield and efficiency of different methods, HD (Hydrodistillationwith vertical condensation tube) was considered to be the best extraction method, theoptimum conditions of HD were: the material and water ratio of1:50(g:mL), distillation timeof30min. The yield of L-borneol was0.85%(dry matter), and the recovery reached93%, andL-borneol content in crude extract was81%. L-borneol (Aipian) was separated from the crudeextract by sublimation at120°C for30min. The purity of L-borneol was91%, and the yieldwas0.83%(dry matter). The process was in free-solvent condition, and the recovery ofL-borneol reached91%. The recrystallization was used to purify L-borneol from “Aipian” andthe purity reached98%. Through repeatable recrystallization,82%of L-borneol in “Aipian”was recoveried, and the yield was0.75%(dry matter). The process is a simple and easy operation and cost less, so it is suitable for the preparation of high-purity L-borneol (98%).The optical activity and NMR showed that the purified L-borneol was really L-borneol.
3. Extraction of essential oil of B. balsamifera leaves
The aroma components of B. balsamifera leaves were collected using headspace solidphase microextraction (HS-SPME). The yields of volatile oil through HDSE and SDE were1.00%and0.98%, respectively. The yield of hydrodistillation-extrusion (HDE) essential oilwas the lowest (only0.19%). The yield of two step hydrodistillation (TSHD) essential oil washigher than that of HDE essential oil, and reached0.32%. The aroma contained mainlysesquiterpenes, and among them caryophyllene content was the highest. Two volatiles oils andHDE essential oil had similar chemical composition and contained a large amout ofmonoterpenes. The differences between TSHD essential oil and other oils were verysignificant, and TSHD essential oil contained mainly sesquiterpenes.
4. Antioxidant and antimicrobial activities of L-borneol and essential oil
L-borneol did not exhibit the valuable antioxidative activity. By comparison, SDEvolatile oil had the best DPPH free radical scavenging capacity (IC50:10.07mg·mL~(-1)). HDSEvolatile oil showed the higher inhibition capacity in BCB (IC50:2.45mg·mL~(-1)). TSHDessential oil had the best performance in TBARS, and it was considered to be suitable asantioxidant in approximate organism environment. The purified L-borneol and standardcompound showed consistent antimicrobial activity, and the value of MIC was1mg·mL~(-1)inantibacterial test, while it showed a better activity to Trichophyton rubrum (MIC:0.13mg·mL~(-1)). HDSE volatile oil, SDE volatile oil, and HDE essential oil showed antimicrobialactivity against the tested bacteria and fungi, and the performance of antifungal activity wasbetter than antibacterial activity. TSHD essential oil had poor performance on the antibacterialactivity, but it had better performance in antifungal test. TSHD essential oil was suitable toinhibit the growth of fungi.
5. Effect of L-borneol on cell wall and membrane
Escherichia coli and Staphylococcus aureus were treated with L-borneol, and the growthcurves and time-kill curves of two bacterial were observed. The membrane potential of cellwas measured using DiBAC4(3). The integrity of cell membrane was observed usingpropidium iodide (PI). The result showed that L-borneol led the death of cell, but the integrityof membrane was not destroyed. L-borneol is in charge of the membrane potential of cell.When there is the existence of L-borneol, the cell depolarized, and membrane ion channel wasaffected, so that the normal growth of bacteria was destroyed to cause death.
1.原料采收期与活性成分的关系研究
为掌握合适的原料采收期，更好的安排生产，快速测定原料中左旋龙脑含量成为第一目标。通过优化六种预处理方法，即水蒸气蒸馏-溶剂萃取法（Hydrodistillation-solventextraction，HDSE）、同时蒸馏萃取法（Simultaneous distillation extraction，SDE）、溶剂浸提法（Solvent extraction，SE）、超声辅助提取法（Ultrasonic-assisted extraction，UAE）、微波辅助提取法（Microwave-assisted extraction，MAE）、超声-微波协同萃取法（Ultrasonic-microwave assisted extraction，UMAE），获得各方法的最佳提取条件。方法学验证结果证实同时测定艾纳香叶中左旋龙脑、樟脑和异龙脑时，只有HDSE-GC的回收率满足需要（100%-105%）；若仅测定左旋龙脑，UMAE-GC的回收率为87%，满足测定需要。比较六种方法的时间、能量、溶剂消耗后发现，消耗最少的方法是UMAE，微波功率100W，提取时间30s，可作为快速测定艾纳香叶中左旋龙脑的预处理方法。最终，测定14个来自采收期的艾纳香叶样品，发现10月15日至次年1月15日采收的艾纳香叶中左旋龙脑含量较高，适合作为生产左旋龙脑的原料。
2.左旋龙脑分离纯化及结构鉴定
比较不同提取方法的得率和效率后发现垂直冷凝收集法是最佳提取方法，最佳条件为料水比1:50（g：mL），蒸馏时间30min，左旋龙脑得率达到0.85%（干物质），提取率达到93%，粗提物中左旋龙脑含量达到81%。在120℃下升华30min可制得左旋龙脑含量为91%的艾片，得率为0.83%（干物质）。以艾片为基料，再利用简单的重结晶法可制得高纯度左旋龙脑（含量>98%），多次反复重结晶可使左旋龙脑的总回收率达82%，最终得率为0.75%（干物质），此过程简单，易操作，成本低，适合用于高纯度左旋龙脑的纯化制备。经旋光性和核磁共振分析证实纯化制得左旋龙脑确实是左旋龙脑。
3.艾纳香精油提取工艺研究
使用顶空固相微萃取（Headspace-solid phase microextraction，HS-SPME）收集艾纳香叶的香气组分；水蒸气蒸馏-溶剂萃取法（HDSE）和同时蒸馏萃取法（SDE）收集的挥发油得率分别为1.00%和0.98%；水蒸气蒸馏-挤压法（Hydrodistillation-extrusion，HDE）收集的精油得率最低，仅为0.19%；本文设计两步水蒸气蒸馏法（Two stephydrodistillation，TSHD）收集的精油得率较HDE精油高，为0.32%。香气主要含倍半萜类；HDSE挥发油、SDE挥发油与HDE精油组分相似，单萜类含量较高；TSHD精油与其他油差异较大，主要含倍半萜类化合物。
4.左旋龙脑和艾纳香精油的抗氧化与抑菌活性
左旋龙脑未表现出明显的、有价值的抗氧化活性。在挥发油和精油中，SDE挥发油具有最好的清除DPPH自由基的能力（IC50:10.07mg·mL~(-1)），HDSE挥发油在抑制β-胡萝卜素氧化中表现最好（IC50:2.45mg·mL~(-1)），TSHD精油在TBARS实验中表现活性最高，最适合在类生命体环境中发挥抗氧化活性。纯化左旋龙脑与标准品表现出一致的抑菌活性，对六种受试细菌的MIC值均为1mg·mL~(-1)，对红色毛癣菌的抑制活性更强（MIC值为0.13mg·mL~(-1)）。HDSE挥发油、SDE挥发油、HDE精油对受试细菌和真菌都表现出抑菌活性，对真菌的抑制能力强于细菌。TSHD精油对抑制受试细菌表现较差，对受试真菌抑制活性较其他三种油更出色，说明TSHD精油更适合用于抗真菌。
5.左旋龙脑对细菌细胞壁膜的影响
利用左旋龙脑处理大肠杆菌和金黄色葡萄球菌，观察其生长曲线的变化，绘制杀菌曲线，通过DiBAC4(3)和PI两染色剂观察细胞的膜电位和膜完整性的变化。结果显示左旋龙脑致细菌细胞死亡时，并未破坏其细胞壁膜的完整性，表现为膜电位改变，细胞去极化，膜的离子通道被影响，最终致其死亡。
Blumea balsamifera (L.) DC.(Asteraceae) is rich in terpenes and flavonoids and is afamous national spice and traditional Chinese medicine from Luodian County in China.Chinese Pharmacopoeia records that B. balsamifera is an important plant source of “Aipian”,natural (–)-borneol. The preparation of “Aipian” has last for over hundreds years in Guizhou,China.
“Aipian” was prepared using the general hydrodistillation at a workshop in early period.With the continual progress of technology, the improvements (automation reconstruction)have been made in the production. However, there still are defects remaining in the process,such as low extraction rate, low yield, poor product quality, etc. Based on the previous workand physicochemical properties of L-borneol, a simple and high efficient preparation processwas designed to prepare high-purity L-borneol and obtain essential oil. The yields, chemicalcompositions, and functional activities of L-borneol and essential oil were studied. Results ofthis study are as follows:
1. Relationship between raw material harvest period and active ingredient
To monitor the variation of material quality during harvest season and to arrangeproduction, the rapid determination of L-borneol in B. balsamifera leaves is indispensable.Six pretreatment methods were optimized to obtain the optimum extraction condition of eachmethod, including hydrodistillation-solvent extraction (HDSE), simultaneous distillationextraction (SDE), solvent extraction (SE), ultrasonic assisted extraction (UAE), microwaveassisted extraction (MAE), and ultrasonic-microwave assisted extraction (UMAE). Methodvalidation confirmed that the recovery of HDSE was the only one, which reached theaccuracy of simultaneous determination of L-borneol, camphor, and isoborneol in leaves, andthe values were between100%-105%. Furthermore, in the determination, the recovery ofL-borneol by UMAE was87%and met the criteria of determination. By comparison in time,energy, and solvent consumption, the consumption of UMAE was the lowest, microwavepower of100W, extraction time of30s, and UMAE was considered as the fastestpretreatment. Finally, fourteen batches of B. balsamifera leaves were determined byHDSE-GC and UMAE-GC, and the leaves harvested from October15to next January15hadhigher L-borneol content and were suitable as material.
2. Isolation, purification, and identification of L-borneol
By comparison in the yield and efficiency of different methods, HD (Hydrodistillationwith vertical condensation tube) was considered to be the best extraction method, theoptimum conditions of HD were: the material and water ratio of1:50(g:mL), distillation timeof30min. The yield of L-borneol was0.85%(dry matter), and the recovery reached93%, andL-borneol content in crude extract was81%. L-borneol (Aipian) was separated from the crudeextract by sublimation at120°C for30min. The purity of L-borneol was91%, and the yieldwas0.83%(dry matter). The process was in free-solvent condition, and the recovery ofL-borneol reached91%. The recrystallization was used to purify L-borneol from “Aipian” andthe purity reached98%. Through repeatable recrystallization,82%of L-borneol in “Aipian”was recoveried, and the yield was0.75%(dry matter). The process is a simple and easy operation and cost less, so it is suitable for the preparation of high-purity L-borneol (98%).The optical activity and NMR showed that the purified L-borneol was really L-borneol.
3. Extraction of essential oil of B. balsamifera leaves
The aroma components of B. balsamifera leaves were collected using headspace solidphase microextraction (HS-SPME). The yields of volatile oil through HDSE and SDE were1.00%and0.98%, respectively. The yield of hydrodistillation-extrusion (HDE) essential oilwas the lowest (only0.19%). The yield of two step hydrodistillation (TSHD) essential oil washigher than that of HDE essential oil, and reached0.32%. The aroma contained mainlysesquiterpenes, and among them caryophyllene content was the highest. Two volatiles oils andHDE essential oil had similar chemical composition and contained a large amout ofmonoterpenes. The differences between TSHD essential oil and other oils were verysignificant, and TSHD essential oil contained mainly sesquiterpenes.
4. Antioxidant and antimicrobial activities of L-borneol and essential oil
L-borneol did not exhibit the valuable antioxidative activity. By comparison, SDEvolatile oil had the best DPPH free radical scavenging capacity (IC50:10.07mg·mL~(-1)). HDSEvolatile oil showed the higher inhibition capacity in BCB (IC50:2.45mg·mL~(-1)). TSHDessential oil had the best performance in TBARS, and it was considered to be suitable asantioxidant in approximate organism environment. The purified L-borneol and standardcompound showed consistent antimicrobial activity, and the value of MIC was1mg·mL~(-1)inantibacterial test, while it showed a better activity to Trichophyton rubrum (MIC:0.13mg·mL~(-1)). HDSE volatile oil, SDE volatile oil, and HDE essential oil showed antimicrobialactivity against the tested bacteria and fungi, and the performance of antifungal activity wasbetter than antibacterial activity. TSHD essential oil had poor performance on the antibacterialactivity, but it had better performance in antifungal test. TSHD essential oil was suitable toinhibit the growth of fungi.
5. Effect of L-borneol on cell wall and membrane
Escherichia coli and Staphylococcus aureus were treated with L-borneol, and the growthcurves and time-kill curves of two bacterial were observed. The membrane potential of cellwas measured using DiBAC4(3). The integrity of cell membrane was observed usingpropidium iodide (PI). The result showed that L-borneol led the death of cell, but the integrityof membrane was not destroyed. L-borneol is in charge of the membrane potential of cell.When there is the existence of L-borneol, the cell depolarized, and membrane ion channel wasaffected, so that the normal growth of bacteria was destroyed to cause death.
引文
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