林荫千里光及华北鸦葱化学成分的研究
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摘要
本论文通过硅胶柱层析(CC)、制备薄层层析(PTLC)ΟRP18硅胶柱层析及重结晶等技术,分别对林荫千里光根部、地上部分和华北鸦葱根部甲醇提取物的化学成分进行分离和纯化,并利用各种现代波谱技术(1D-NMR,2D-NMR, MS,FT-IR)对化合物进行分析测试,在与标准品对照或与文献数据比较的基础上,对所获得的22个化合物的结构进行了鉴定,并发现其中6个化合物为新化合物、16个化合物为已知化合物。本研究还采用水蒸气蒸馏法提取林荫千里光、华北鸦葱不同部位的挥发油,并利用气相色谱-质谱联用(GC-MS)技术分别对所获得的7个挥发油样品的化学成分进行分析。
林荫千里光(Senecio nemorensis L.)为菊科(Compositae)千里光属(Senecio)植物,全草入药,有清热解毒、凉血、消肿等功效,用于治疗痢疾、肠炎、肝炎、结膜炎、目赤红肿、中耳炎、痈疖疔毒等。国内外对于林荫千里光化学成分的研究始于1963年。目前为止,国内外其他学者共从林荫千里光中分离鉴定出40种化合物,包括4个新化合物。
本研究以产自山东省昆嵛山地区的林荫千里光为研究对象,对其根部和地上部分的化学成分进行了系统研究。从林荫千里光的根部甲醇提取物中分离鉴定出5个化合物的结构(SnR-1至SnR-5),包括4个新化合物：8α-羟基-6β-异丁酰氧基-1-氧代艾里莫芬-7(11),9-二烯-12,8β-内酯(SnR-2)、6β,8β-二甲氧基-1-氧代艾里莫芬-7(11),9-二烯-12,8α-内酯(SnR-3)、10α-羟基-6β-异丁酰氧基-1-氧代艾里莫芬-7(11),8-二烯-12,8-内酯(SnR-4)和10α-羟基-6β-丙酰氧基-1-氧代艾里莫芬-7(11),8-二烯-12,8-内酯(SnR-5)；从林荫千里光地上部分的甲醇提取物中分离得到6个化合物,鉴定了6个化合物的结构(SnA-1至SnA-6),包括2个新化合物：8α-羟基-6β-异丁酰氧基-艾里莫芬-7(11),1(10)-二烯-12,8β-内酯(SnA-5)和11-羟基-1β-甲氧基-8-氧代艾里莫芬-6,9-二烯-12-羧酸甲基酯(SnA-6)。
本研究还首次采用GC-MS方法分别对林荫千里光根、茎、叶和花的挥发油的化学成分进行了分析和比较。从林荫千里光根、茎、叶和花四个部位的挥发油中共鉴定出108种化合物,有11种化合物为根、茎、叶、花四个部位所共有。其中,根挥发油中50种,主要为芳香族化合物(56.66%)和萜类化合物(38.77%)；茎挥发油中52种,主要为萜类化合物(77.90%)和脂肪族化合物(17.42%)；叶挥发油中32种,主要为萜类化合物(93.04%)；花挥发油中43种,主要为萜类化合物(83.87%)。
另外,本文还对华北鸦葱根部甲醇提取物及不同部位挥发油的化学成分进行了研究。
华北鸦葱(Scorzonera albicaulis Bunge)为菊科(Compositae)鸦葱属(Scorzonera)植物,以根入药,具有清热解毒、祛风除湿、平喘之功效,主治感冒发热、哮喘、乳腺炎、疔疮、关节痛、带状疱疹等。迄今,国内外尚没有关于华北鸦葱(Scorzonera albicaulis Bunge)化学成分研究的报道。
本研究以采自山东省威海市的华北鸦葱作为研究对象,对其根部的化学成分进行了系统研究。从华北鸦葱根部的甲醇提取物中分离鉴定出11个化合物的结构：Sa-1至Sa-11,均为已知化合物,其中有5个化合物(Sa-1, Sa-3, Sa-5, Sa-6, Sa-7)为鸦葱(Scorzonera)属中首次发现。
本研究首次采用GC-MS方法分别对华北鸦葱根、茎叶和花的挥发油的化学成分进行了分析和比较。从华北鸦葱根、茎叶和花三个部位的挥发油中共鉴定出40种化合物,有2种化合物为三个部位所共有,其中,根、茎叶和花挥发油中分别鉴定出8种、24种和15种化学成分。三个部位挥发油中主要成分均为脂肪酸类和酯类,其中根部挥发油主要成分是正十五烷酸(62.18%)和亚油酸(17.55)；茎叶部主要成分为正十六烷酸(47.95%)、亚麻酸乙酯(8.72%)和亚油酸(7.24%)；花部主要成分是邻苯二甲酸二甲酯(25.56%)和正十七烷酸(7.34%)。
综上,本论文对林荫千里光和华北鸦葱的化学成分进行了系统研究,这对两种植物的开发利用及其植物药理活性研究有一定的指导意义。
In this thesis, the phytochemical constituents in the methanol extracts from roots and aerial parts of Senecio nemorensis L. as well as roots of Scorzonera albicaulis Bunge have been isolated by means of silica column chromatography, preparative thin layer chromatography, reverse phase C-18 silica column chromatography and recrystallization. These compounds were analyzed by modern spectroscopy as 1D-NMR,2D-NMR, MS and FT-IR. On the basis of comparison with standard sample and spectral data in literatures, structures of 22 compounds have been identified with 6 compounds being new and 16 compounds being known. In addition, the separation of essential oils from different parts of Senecio nemorensis L. and Scorzonera albicaulis Bunge has also been accomplished, employing water steam distillation method. The chemical components in 7 essential oil samples prepared as above have been analyzed by gas chromatography-mass spectroscopy (GC-MS).
Senecio nemorensis L. belongs to Senecio, Compositae. The whole plant has been used for the treatment of dysentery, enteritis, hepatitis, conjunctivitis, bloodshot eyes, otitis media in traditional and folk medicine for their clearing heat, detoxication, cooling blood and detumescence properties. Investigation on phytochemical constituents in Senecio nemorensis L. has begun since 1963, and 40 compounds have been isolated and elucidated by other groups, among which 4 compounds are novel.
In this thesis, chemical constituents in roots and aerial parts of Senecio nemorensis L. collected at Kunyu Mountain located in the east of Shandong Province in China, have been comprehensively investigated.
Firstly,5 compounds, marked as SnR-1 to SnR-5, have been isolated from methanol extracts of roots of Senecio nemorensis L.. Structures of 5 compounds have been identified by such modern spectroscopic technique as 1D-NMR,2D-NMR, MS and FT-IR combined with comparison with standard sample or data in literatures, among which there are 4 compounds as follows,8a-hydroxy-6β-(isobutanoyloxy)-1-oxoeremophila-7(11),9-dieno-12,8β-lactone (SnR-2),6β,8β-dimethoxy-1-oxoeremo-phila-7(11),9-dieno-12,8α-lactone (SnR-3),10α-hydroxy-6β-(isobutanoyloxy)-1- oxoeremophila-7(11),8-dieno-12,8-lactone (SnR-4), and 10a-hydroxy-6β-propionyloxy-1-oxoeremophila-7(11),8-dieno-12,8-lactone (SnR-5). Secondly, structures of 6 compounds marked as SnA-1 to SnA-6, separated from methanol extracts from aerial parts of Senecio nemorensis L., have also been elucidated. There are 2 new compounds among these compounds as follows,8a-hydroxy-6β-(isobutanoyloxy)-eremophila-7(11),1(10)-dieno-12,8β-lactone (SnA-5) and 11-hydroxy-1β-methoxyl-8-oxoeremophila-6,9-dien-12-oic methyl ester (SnA-6).
In addition, for the first time, the chemical composition of essential oils separated from roots, stems, leaves and flowers of Senecio nemorensis L. has been analyzed by GC-MS.108 compounds have been identified with 11 compounds being common.
Specifically, there are 50 compounds in root essential oil, mainly aromatic (56.66%) and terpene (38.77%) compounds; 52 compounds in stem essential oil, mainly terpene (77.90%) and aliphatic (17.42%) compounds;32 compounds in leaf essential oil, mainly terpene compounds (93.04%) and 43 compounds in flower essential oil, mainly terpene compounds (83.87%).
Furthermore, chemical constituents in methanol extracts from roots and essential oils from different organs of Scorzonera albicaulis Bunge have also been studied.
Scorzonera albicaulis Bunge belongs to Scorzonera, Compositae. Roots of Scorzonera albicaulis Bunge have been used in traditional and folk medicine for the treatment of inflammation, fever, asthma, mastitis, furunculosis, arthralgia, Herpes Zoster for their clearing heat, detoxication, dispelling wind, removing dampness and preventing ashma propeties. To the knowledge of author, there are few reports about the research on the chemical constituents in Scorzonera albicaulis Bunge.
In this thesis, we have also investigated the phytochemical constituents in methanol extracts from roots of Scorzonera albicaulis Bunge collected in Weihai, Shandong Province.14 compounds have been isolated, among which 11 compounds marked as Sa-1 to Sa-11, have been identified as known compounds. And five compounds (Sa-1, Sa-3, Sa-5, Sa-6, Sa-7) are discovered in Scorzonera plants for the first time.
In this thesis, analysis of chemical constituents in essential oils separated from such different parts as roots, stems and leaves, flowers of Scorzonera albicaulis Bunge has also been carried out by GC-MS for the first time.40 compounds, most of which are aliphatic acids and aliphatic esters, have been identified with 2 compounds being common.
Specifically, there are mainly n-pentadacanoic acid (62.18%) and linoleic acid (17.55%) in root essential oil, mainly n-hexadacanoic acid (47.95%), ethyl linolenate (8.72%) and linoleic acid (7.24%) in stem and leaf essential oil, and mainly dimethyl phthalate (25.56%) and n-heptadecanoic acid (7.34%) in flower essential oil.
In conclusion, the chemical constituents in Senecio nemorensis L. and Scorzonera alcaubilis Bunge have been comprehensively investigated, which might be of significance for the exploitation and phytopharmacological studies of these two species.
林荫千里光(Senecio nemorensis L.)为菊科(Compositae)千里光属(Senecio)植物,全草入药,有清热解毒、凉血、消肿等功效,用于治疗痢疾、肠炎、肝炎、结膜炎、目赤红肿、中耳炎、痈疖疔毒等。国内外对于林荫千里光化学成分的研究始于1963年。目前为止,国内外其他学者共从林荫千里光中分离鉴定出40种化合物,包括4个新化合物。
本研究以产自山东省昆嵛山地区的林荫千里光为研究对象,对其根部和地上部分的化学成分进行了系统研究。从林荫千里光的根部甲醇提取物中分离鉴定出5个化合物的结构(SnR-1至SnR-5),包括4个新化合物：8α-羟基-6β-异丁酰氧基-1-氧代艾里莫芬-7(11),9-二烯-12,8β-内酯(SnR-2)、6β,8β-二甲氧基-1-氧代艾里莫芬-7(11),9-二烯-12,8α-内酯(SnR-3)、10α-羟基-6β-异丁酰氧基-1-氧代艾里莫芬-7(11),8-二烯-12,8-内酯(SnR-4)和10α-羟基-6β-丙酰氧基-1-氧代艾里莫芬-7(11),8-二烯-12,8-内酯(SnR-5)；从林荫千里光地上部分的甲醇提取物中分离得到6个化合物,鉴定了6个化合物的结构(SnA-1至SnA-6),包括2个新化合物：8α-羟基-6β-异丁酰氧基-艾里莫芬-7(11),1(10)-二烯-12,8β-内酯(SnA-5)和11-羟基-1β-甲氧基-8-氧代艾里莫芬-6,9-二烯-12-羧酸甲基酯(SnA-6)。
本研究还首次采用GC-MS方法分别对林荫千里光根、茎、叶和花的挥发油的化学成分进行了分析和比较。从林荫千里光根、茎、叶和花四个部位的挥发油中共鉴定出108种化合物,有11种化合物为根、茎、叶、花四个部位所共有。其中,根挥发油中50种,主要为芳香族化合物(56.66%)和萜类化合物(38.77%)；茎挥发油中52种,主要为萜类化合物(77.90%)和脂肪族化合物(17.42%)；叶挥发油中32种,主要为萜类化合物(93.04%)；花挥发油中43种,主要为萜类化合物(83.87%)。
另外,本文还对华北鸦葱根部甲醇提取物及不同部位挥发油的化学成分进行了研究。
华北鸦葱(Scorzonera albicaulis Bunge)为菊科(Compositae)鸦葱属(Scorzonera)植物,以根入药,具有清热解毒、祛风除湿、平喘之功效,主治感冒发热、哮喘、乳腺炎、疔疮、关节痛、带状疱疹等。迄今,国内外尚没有关于华北鸦葱(Scorzonera albicaulis Bunge)化学成分研究的报道。
本研究以采自山东省威海市的华北鸦葱作为研究对象,对其根部的化学成分进行了系统研究。从华北鸦葱根部的甲醇提取物中分离鉴定出11个化合物的结构：Sa-1至Sa-11,均为已知化合物,其中有5个化合物(Sa-1, Sa-3, Sa-5, Sa-6, Sa-7)为鸦葱(Scorzonera)属中首次发现。
本研究首次采用GC-MS方法分别对华北鸦葱根、茎叶和花的挥发油的化学成分进行了分析和比较。从华北鸦葱根、茎叶和花三个部位的挥发油中共鉴定出40种化合物,有2种化合物为三个部位所共有,其中,根、茎叶和花挥发油中分别鉴定出8种、24种和15种化学成分。三个部位挥发油中主要成分均为脂肪酸类和酯类,其中根部挥发油主要成分是正十五烷酸(62.18%)和亚油酸(17.55)；茎叶部主要成分为正十六烷酸(47.95%)、亚麻酸乙酯(8.72%)和亚油酸(7.24%)；花部主要成分是邻苯二甲酸二甲酯(25.56%)和正十七烷酸(7.34%)。
综上,本论文对林荫千里光和华北鸦葱的化学成分进行了系统研究,这对两种植物的开发利用及其植物药理活性研究有一定的指导意义。
In this thesis, the phytochemical constituents in the methanol extracts from roots and aerial parts of Senecio nemorensis L. as well as roots of Scorzonera albicaulis Bunge have been isolated by means of silica column chromatography, preparative thin layer chromatography, reverse phase C-18 silica column chromatography and recrystallization. These compounds were analyzed by modern spectroscopy as 1D-NMR,2D-NMR, MS and FT-IR. On the basis of comparison with standard sample and spectral data in literatures, structures of 22 compounds have been identified with 6 compounds being new and 16 compounds being known. In addition, the separation of essential oils from different parts of Senecio nemorensis L. and Scorzonera albicaulis Bunge has also been accomplished, employing water steam distillation method. The chemical components in 7 essential oil samples prepared as above have been analyzed by gas chromatography-mass spectroscopy (GC-MS).
Senecio nemorensis L. belongs to Senecio, Compositae. The whole plant has been used for the treatment of dysentery, enteritis, hepatitis, conjunctivitis, bloodshot eyes, otitis media in traditional and folk medicine for their clearing heat, detoxication, cooling blood and detumescence properties. Investigation on phytochemical constituents in Senecio nemorensis L. has begun since 1963, and 40 compounds have been isolated and elucidated by other groups, among which 4 compounds are novel.
In this thesis, chemical constituents in roots and aerial parts of Senecio nemorensis L. collected at Kunyu Mountain located in the east of Shandong Province in China, have been comprehensively investigated.
Firstly,5 compounds, marked as SnR-1 to SnR-5, have been isolated from methanol extracts of roots of Senecio nemorensis L.. Structures of 5 compounds have been identified by such modern spectroscopic technique as 1D-NMR,2D-NMR, MS and FT-IR combined with comparison with standard sample or data in literatures, among which there are 4 compounds as follows,8a-hydroxy-6β-(isobutanoyloxy)-1-oxoeremophila-7(11),9-dieno-12,8β-lactone (SnR-2),6β,8β-dimethoxy-1-oxoeremo-phila-7(11),9-dieno-12,8α-lactone (SnR-3),10α-hydroxy-6β-(isobutanoyloxy)-1- oxoeremophila-7(11),8-dieno-12,8-lactone (SnR-4), and 10a-hydroxy-6β-propionyloxy-1-oxoeremophila-7(11),8-dieno-12,8-lactone (SnR-5). Secondly, structures of 6 compounds marked as SnA-1 to SnA-6, separated from methanol extracts from aerial parts of Senecio nemorensis L., have also been elucidated. There are 2 new compounds among these compounds as follows,8a-hydroxy-6β-(isobutanoyloxy)-eremophila-7(11),1(10)-dieno-12,8β-lactone (SnA-5) and 11-hydroxy-1β-methoxyl-8-oxoeremophila-6,9-dien-12-oic methyl ester (SnA-6).
In addition, for the first time, the chemical composition of essential oils separated from roots, stems, leaves and flowers of Senecio nemorensis L. has been analyzed by GC-MS.108 compounds have been identified with 11 compounds being common.
Specifically, there are 50 compounds in root essential oil, mainly aromatic (56.66%) and terpene (38.77%) compounds; 52 compounds in stem essential oil, mainly terpene (77.90%) and aliphatic (17.42%) compounds;32 compounds in leaf essential oil, mainly terpene compounds (93.04%) and 43 compounds in flower essential oil, mainly terpene compounds (83.87%).
Furthermore, chemical constituents in methanol extracts from roots and essential oils from different organs of Scorzonera albicaulis Bunge have also been studied.
Scorzonera albicaulis Bunge belongs to Scorzonera, Compositae. Roots of Scorzonera albicaulis Bunge have been used in traditional and folk medicine for the treatment of inflammation, fever, asthma, mastitis, furunculosis, arthralgia, Herpes Zoster for their clearing heat, detoxication, dispelling wind, removing dampness and preventing ashma propeties. To the knowledge of author, there are few reports about the research on the chemical constituents in Scorzonera albicaulis Bunge.
In this thesis, we have also investigated the phytochemical constituents in methanol extracts from roots of Scorzonera albicaulis Bunge collected in Weihai, Shandong Province.14 compounds have been isolated, among which 11 compounds marked as Sa-1 to Sa-11, have been identified as known compounds. And five compounds (Sa-1, Sa-3, Sa-5, Sa-6, Sa-7) are discovered in Scorzonera plants for the first time.
In this thesis, analysis of chemical constituents in essential oils separated from such different parts as roots, stems and leaves, flowers of Scorzonera albicaulis Bunge has also been carried out by GC-MS for the first time.40 compounds, most of which are aliphatic acids and aliphatic esters, have been identified with 2 compounds being common.
Specifically, there are mainly n-pentadacanoic acid (62.18%) and linoleic acid (17.55%) in root essential oil, mainly n-hexadacanoic acid (47.95%), ethyl linolenate (8.72%) and linoleic acid (7.24%) in stem and leaf essential oil, and mainly dimethyl phthalate (25.56%) and n-heptadecanoic acid (7.34%) in flower essential oil.
In conclusion, the chemical constituents in Senecio nemorensis L. and Scorzonera alcaubilis Bunge have been comprehensively investigated, which might be of significance for the exploitation and phytopharmacological studies of these two species.
引文
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