大花金挖耳花蕾中萜类成分的研究
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摘要
大花金挖耳(Carpesium macrocephalum Franch. Et Sav.)又名香油罐,是菊科(Compositae)天名精属多年生草本植物,具有清热、解毒、消炎、止血、杀虫等功能。近年来韩国和我国兰州大学等地的研究表明其含有单萜、倍半萜、三萜、黄酮、香豆素、甾醇及其甙、苯的衍生物等,其中倍半萜内酯类化合物占多数。大量的研究表明大花金挖耳花蕾中含有高活性的成分,为深度开发和综合利用大花金挖耳资源,本文拟以植物化学理论和现代化学分离分析技术为基础,对该植物进行了以下的研究工作:
1.利用水蒸气蒸馏法和超临界萃取法对大花金挖耳不同部位(根、茎、叶、花及花托)挥发油含量进行了比较分析,结果表明大花金挖耳花的挥发油含量明显高于其它四个部位;并利用GC-MS对水蒸气蒸馏法得到的五种挥发油进行了成分分析,从大花金挖耳5种挥发油中共鉴定出130种成分,从根、茎、叶、花及花托中分别鉴定出了41、45、60、40和46种化合物,已鉴定挥发油成分占总挥发油的含量分别为86.59%、90.75%、84.43%、87.95%和91.38%。5个部位挥发油化学组成差异较大:根挥发油主要成分为倍半萜类和酯类;茎挥发油主要成分为倍半萜和烯类(包括烯醇、烯酸、烯酮);叶和花挥发油主要成分为烯类(包括烯醇、烯酸、烯酮)和酯类;花托挥发油主要成分为倍半萜类和二萜类。对大花金挖耳根、茎、叶和花托挥发油化学成分的研究为首次报道。
2.采用紫外分光光度法对大花金挖耳不同部位(根、茎、叶、花及花托)中的甾醇含量进行测定,结果表明:大花金挖耳不同部位甾醇含量相差较大,分布情况为:叶(92.909mg/g)>花(41.154mg/g)>花托(23.735 mg/g)>根(6.179mg/g)>茎(4.935mg/g),根、茎的甾醇含量明显小于其它三个部位。
3.在大花金挖耳花蕾化学成分系统预试的基础上通过柱层析、薄层制备及重结晶等分离纯化技术,从大花金挖耳花蕾的甲醇提取物和石油醚(60～90℃)-丙酮(6:1)提取物中共分离得到15个化合物,利用现代波谱技术(IR,EI-MS,1HNMR,13CNMR,DEPT,1H-1HCOSY,HSQC,HMBC)鉴定了12个化合物,分别为:β-谷甾醇(H1)、异土木香内酯(H2)、6-甲基-10-亚甲基-1-羟基二环[4.4.0]-癸烷-4-酮(H3)、5α, 6α-环氧-4α,11α-桉烷-12, 8β-内酯(H4)、α-香树酯醇(H5)、β-香树酯醇(H6)、ivalin(H7)、β-胡萝卜甙(H8),特勒内酯(H9)、天名精内酯酮(H10)、天名精内酯醇(H14)、二氢特勒内酯(H15),其中H3和H4为新化合物,H5和H6为首次从该属植物中分离得到。在分离的基础上对特勒内酯的制备进行了初步研究,发现经干法柱层析用氯枋-丙酮(10:1)洗脱可将特勒内酯与天名精内酯酮和有色物质分离开来。并且经西北农林科技大学无公害农药研究中心帮助测试了5个倍半萜内酯化合物对番茄灰霉病菌、烟草赤星病菌、苹果炭疽病菌和玉米大斑病菌孢子萌发的抑制作用,结果表明:五个化合物对供试病菌孢子萌发均具有不同程度的抑制作用。
4.对分离得到的一个典型桉烷型倍半萜内酯类化合物ivalin的C-2位仲羟基进行结构修饰,主要有乙酰化、丙酰化、丁酰化、苯甲酰化、苯磺酰化和甲醚化,产物经过硅胶柱层析和重结晶得到七个化合物,经过EI-MS和IR鉴确证了其中六个化合物的结构,这些衍生物为进一步的活性研究提供了依据。
本论文初步明确了大花金挖耳花蕾中萜类成分特征及其杀菌活性。对大花金挖耳不同部位的挥发油含量、成分和甾醇含量进行了初步研究;从大花金挖耳花蕾的甲醇提取物和石油醚(60～90℃)-丙酮(6:1)提取物中共分离得到15个化合物,其中2个为新的化合物,2个为首次从该属植物中分离得到,在此基础上初步评价了5个倍半萜内酯的抑菌活性;并对分离得到的一个典型桉烷型倍半萜内酯类化合物ivalin的C-2位仲羟基进行结构修饰,得到了七个化合物,为进一步的活性研究提供了依据。这些研究丰富了大花金挖耳的研究内容,为进一步认识和合理开发利用该植物资源提供了理论和实验依据,特别6-甲基-10-亚甲基-1-羟基二环[4.4.0]-癸烷-4-酮是一个12个碳骨架的化合物,在天然产物中比较稀有,值得进一步研究。
Carpesium macrocephalum Franch.Et Sav., a perennial grass, belongs to Compositae and Carpesium L.. It has antipyretic, detoxification, anti - inflammation, hemostasis, insecticide and other functions. The researches in Korea, Lanzhou University, and other research institutes showed that it contained monoterpenes, sesquiterpenes, flavonoids, coumarins, sterols, steroidal glycoside and benzene deriveatives, and sesquiterpene lactones is the major constituents. Many evidences indicate that the flower buds of C. macrocephalum Franch. Et Sav contains high active components. In order to provide basis for further development and comprehensive utilization of this important plant resources, based on the theories and principles of phytochemistry, modern chemical separation and purification methods, we carried out studies as follows:
1. The constituents of the essential oils extract from the root, stem, leaf, flower and receptacle of Carpesium macrocephalum Franch.et Sav. were analyzed by GC-MS. The five essential oils contain 130 components, 41 from the root, providing 86.59% of the corresponding oil; 45 from the stem, providing 90.75%; 60 from the leaf, providing 84.43%; 40 from the flower, providing 87.95%; 46 from the receptacle, providing 91.38%. The constituents of the five essential oils from the five parts are significantly different. The major constituents of root are sesquiterpenes and esters; and the constituents of stem are mainly sesquiterpenes and alkenes (olefinic alcohols, ketenes and olefine acids); the mostly constituents in leaf and flower are alkenes (olefinic alcohols, ketenes and olefine acids) and esters; finally, the receptacle mainly containes sesquiterpenes and diterpenes. The chemical constituents analyzed by GC-MS of the essential oils from the root, stem, leaf and receptacle of C. macrocephalum Franch.et Sav were reported for the first time.
2. The contents of sterol in different parts (root, stem, leaf, flower and receptacle) of C. macrocephalum were determined by UV method. The results showed that the contents of sterol in different parts were obviously different. The distribution of sterol was as follows: leaf (92.909mg/g) > flower (41.154mg/g) > receptacle (23.735 mg/g) > root (6.179mg/g)> stem (4.935mg/g). The contents of sterol in root and stem are significantly lower than that in other three parts.
3. Based on the systematical pretest on the chemical constitutents in flower buds of the C. macrocephalum Franch. Et Sav., 21 compounds were isolated from its methanol and petroleum ether (60~90°C)– acetone (6:1) extracts by CC, TLC, recrystallization and so on. 12 of them were identified asβ–sitosterol(H1), isoalantolactone(H2), 6-methyl-10- methylene-7-hydroxy-dicyclo[4,4,0]-decane-4-one(H3), 5α,6α-epoxy-4α, 11α-eudesma-12, 8β- olide(H4),α-amyrin (H5) andβ-amyrin (H6), ivalin (H7),β-daucosterol (H8), telekin (H9), carabrone (H10), carabrol (H14), dihydrotelekin (H15), by modern spectroscopic techniques (IR, EI-MS, 1HNMR, 13CNMR, DEPT, 1H-1HCOSY, HSQC, HMBC). Noticeably, H3, H4 are new compounds, and H5 and H6 are found from this plant for the the first time. The preliminary study of preparating telekin showed that both telekin and carabrone were easily isolated from color substance through chloroform- acetone(10:1) on dry column chromatography. Additionally, H2, H7, H9, H10and H14 can inhibit spores germination of Alternaria longipes,Glomerella cingulata and Exserohilum turcicum in different extent, which were researched at Research and Development Center of Biorational Pesticide, Northwest A&F University.
4. A typical eudesmane-type sesquiterpene lactones-ivalin was separated from the flower buds of C. macrocephalum Franch.Et Sav.. And the structure was modified on C-2 sec-hydroxyl. These structure modifications are acetylation, Propionylatio, acidylation, benzoylation, benzoylate sulfonylation and methylation. As a result, seven products were separated by CC and recrystallization, six compounds of which were identified. These derivatives provide basis for further activity investigation.
In this thesis, C. macrocephalum Franch. Et Sav.’s terpenoid characteristics and antifungal activities were displayed. The content and composition of essential oils in its different parts and the content of sterol were also determined. 15 compounds were isolated from its methanol and petroleum ether (60 ~ 90°C) - acetone (6:1) extracts. Noticeably, H3 and H4 are novel compounds, and H5 and H6 are found from this plant for the first time. Then antifungal activities of five sesquiterpene lactones were preliminary assessed. Additionally, a typical eudesmane-type sesquiterpene lactones-ivalin was separated and structure modified, and seven compounds were achieved. These will provide basis for further activity investigation. All the above research enrich the study of chemistry of botanical resource of C. macrocephalum, and provide academic and experimental results for the further identification and rational utilization of the plant resource. Especially, H3 deserves further study, which is a 12 carbon skeleton compounds and rare in nature products.
1.利用水蒸气蒸馏法和超临界萃取法对大花金挖耳不同部位(根、茎、叶、花及花托)挥发油含量进行了比较分析,结果表明大花金挖耳花的挥发油含量明显高于其它四个部位;并利用GC-MS对水蒸气蒸馏法得到的五种挥发油进行了成分分析,从大花金挖耳5种挥发油中共鉴定出130种成分,从根、茎、叶、花及花托中分别鉴定出了41、45、60、40和46种化合物,已鉴定挥发油成分占总挥发油的含量分别为86.59%、90.75%、84.43%、87.95%和91.38%。5个部位挥发油化学组成差异较大:根挥发油主要成分为倍半萜类和酯类;茎挥发油主要成分为倍半萜和烯类(包括烯醇、烯酸、烯酮);叶和花挥发油主要成分为烯类(包括烯醇、烯酸、烯酮)和酯类;花托挥发油主要成分为倍半萜类和二萜类。对大花金挖耳根、茎、叶和花托挥发油化学成分的研究为首次报道。
2.采用紫外分光光度法对大花金挖耳不同部位(根、茎、叶、花及花托)中的甾醇含量进行测定,结果表明:大花金挖耳不同部位甾醇含量相差较大,分布情况为:叶(92.909mg/g)>花(41.154mg/g)>花托(23.735 mg/g)>根(6.179mg/g)>茎(4.935mg/g),根、茎的甾醇含量明显小于其它三个部位。
3.在大花金挖耳花蕾化学成分系统预试的基础上通过柱层析、薄层制备及重结晶等分离纯化技术,从大花金挖耳花蕾的甲醇提取物和石油醚(60～90℃)-丙酮(6:1)提取物中共分离得到15个化合物,利用现代波谱技术(IR,EI-MS,1HNMR,13CNMR,DEPT,1H-1HCOSY,HSQC,HMBC)鉴定了12个化合物,分别为:β-谷甾醇(H1)、异土木香内酯(H2)、6-甲基-10-亚甲基-1-羟基二环[4.4.0]-癸烷-4-酮(H3)、5α, 6α-环氧-4α,11α-桉烷-12, 8β-内酯(H4)、α-香树酯醇(H5)、β-香树酯醇(H6)、ivalin(H7)、β-胡萝卜甙(H8),特勒内酯(H9)、天名精内酯酮(H10)、天名精内酯醇(H14)、二氢特勒内酯(H15),其中H3和H4为新化合物,H5和H6为首次从该属植物中分离得到。在分离的基础上对特勒内酯的制备进行了初步研究,发现经干法柱层析用氯枋-丙酮(10:1)洗脱可将特勒内酯与天名精内酯酮和有色物质分离开来。并且经西北农林科技大学无公害农药研究中心帮助测试了5个倍半萜内酯化合物对番茄灰霉病菌、烟草赤星病菌、苹果炭疽病菌和玉米大斑病菌孢子萌发的抑制作用,结果表明:五个化合物对供试病菌孢子萌发均具有不同程度的抑制作用。
4.对分离得到的一个典型桉烷型倍半萜内酯类化合物ivalin的C-2位仲羟基进行结构修饰,主要有乙酰化、丙酰化、丁酰化、苯甲酰化、苯磺酰化和甲醚化,产物经过硅胶柱层析和重结晶得到七个化合物,经过EI-MS和IR鉴确证了其中六个化合物的结构,这些衍生物为进一步的活性研究提供了依据。
本论文初步明确了大花金挖耳花蕾中萜类成分特征及其杀菌活性。对大花金挖耳不同部位的挥发油含量、成分和甾醇含量进行了初步研究;从大花金挖耳花蕾的甲醇提取物和石油醚(60～90℃)-丙酮(6:1)提取物中共分离得到15个化合物,其中2个为新的化合物,2个为首次从该属植物中分离得到,在此基础上初步评价了5个倍半萜内酯的抑菌活性;并对分离得到的一个典型桉烷型倍半萜内酯类化合物ivalin的C-2位仲羟基进行结构修饰,得到了七个化合物,为进一步的活性研究提供了依据。这些研究丰富了大花金挖耳的研究内容,为进一步认识和合理开发利用该植物资源提供了理论和实验依据,特别6-甲基-10-亚甲基-1-羟基二环[4.4.0]-癸烷-4-酮是一个12个碳骨架的化合物,在天然产物中比较稀有,值得进一步研究。
Carpesium macrocephalum Franch.Et Sav., a perennial grass, belongs to Compositae and Carpesium L.. It has antipyretic, detoxification, anti - inflammation, hemostasis, insecticide and other functions. The researches in Korea, Lanzhou University, and other research institutes showed that it contained monoterpenes, sesquiterpenes, flavonoids, coumarins, sterols, steroidal glycoside and benzene deriveatives, and sesquiterpene lactones is the major constituents. Many evidences indicate that the flower buds of C. macrocephalum Franch. Et Sav contains high active components. In order to provide basis for further development and comprehensive utilization of this important plant resources, based on the theories and principles of phytochemistry, modern chemical separation and purification methods, we carried out studies as follows:
1. The constituents of the essential oils extract from the root, stem, leaf, flower and receptacle of Carpesium macrocephalum Franch.et Sav. were analyzed by GC-MS. The five essential oils contain 130 components, 41 from the root, providing 86.59% of the corresponding oil; 45 from the stem, providing 90.75%; 60 from the leaf, providing 84.43%; 40 from the flower, providing 87.95%; 46 from the receptacle, providing 91.38%. The constituents of the five essential oils from the five parts are significantly different. The major constituents of root are sesquiterpenes and esters; and the constituents of stem are mainly sesquiterpenes and alkenes (olefinic alcohols, ketenes and olefine acids); the mostly constituents in leaf and flower are alkenes (olefinic alcohols, ketenes and olefine acids) and esters; finally, the receptacle mainly containes sesquiterpenes and diterpenes. The chemical constituents analyzed by GC-MS of the essential oils from the root, stem, leaf and receptacle of C. macrocephalum Franch.et Sav were reported for the first time.
2. The contents of sterol in different parts (root, stem, leaf, flower and receptacle) of C. macrocephalum were determined by UV method. The results showed that the contents of sterol in different parts were obviously different. The distribution of sterol was as follows: leaf (92.909mg/g) > flower (41.154mg/g) > receptacle (23.735 mg/g) > root (6.179mg/g)> stem (4.935mg/g). The contents of sterol in root and stem are significantly lower than that in other three parts.
3. Based on the systematical pretest on the chemical constitutents in flower buds of the C. macrocephalum Franch. Et Sav., 21 compounds were isolated from its methanol and petroleum ether (60~90°C)– acetone (6:1) extracts by CC, TLC, recrystallization and so on. 12 of them were identified asβ–sitosterol(H1), isoalantolactone(H2), 6-methyl-10- methylene-7-hydroxy-dicyclo[4,4,0]-decane-4-one(H3), 5α,6α-epoxy-4α, 11α-eudesma-12, 8β- olide(H4),α-amyrin (H5) andβ-amyrin (H6), ivalin (H7),β-daucosterol (H8), telekin (H9), carabrone (H10), carabrol (H14), dihydrotelekin (H15), by modern spectroscopic techniques (IR, EI-MS, 1HNMR, 13CNMR, DEPT, 1H-1HCOSY, HSQC, HMBC). Noticeably, H3, H4 are new compounds, and H5 and H6 are found from this plant for the the first time. The preliminary study of preparating telekin showed that both telekin and carabrone were easily isolated from color substance through chloroform- acetone(10:1) on dry column chromatography. Additionally, H2, H7, H9, H10and H14 can inhibit spores germination of Alternaria longipes,Glomerella cingulata and Exserohilum turcicum in different extent, which were researched at Research and Development Center of Biorational Pesticide, Northwest A&F University.
4. A typical eudesmane-type sesquiterpene lactones-ivalin was separated from the flower buds of C. macrocephalum Franch.Et Sav.. And the structure was modified on C-2 sec-hydroxyl. These structure modifications are acetylation, Propionylatio, acidylation, benzoylation, benzoylate sulfonylation and methylation. As a result, seven products were separated by CC and recrystallization, six compounds of which were identified. These derivatives provide basis for further activity investigation.
In this thesis, C. macrocephalum Franch. Et Sav.’s terpenoid characteristics and antifungal activities were displayed. The content and composition of essential oils in its different parts and the content of sterol were also determined. 15 compounds were isolated from its methanol and petroleum ether (60 ~ 90°C) - acetone (6:1) extracts. Noticeably, H3 and H4 are novel compounds, and H5 and H6 are found from this plant for the first time. Then antifungal activities of five sesquiterpene lactones were preliminary assessed. Additionally, a typical eudesmane-type sesquiterpene lactones-ivalin was separated and structure modified, and seven compounds were achieved. These will provide basis for further activity investigation. All the above research enrich the study of chemistry of botanical resource of C. macrocephalum, and provide academic and experimental results for the further identification and rational utilization of the plant resource. Especially, H3 deserves further study, which is a 12 carbon skeleton compounds and rare in nature products.
引文
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