北美刺人参的化学成分研究
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摘要
目的:对北美刺人参叶、茎的化学成分及北美刺人参叶挥发油的化学成分进行分析。
材料与方法:1.本实验利用硅胶柱色谱、Sephadex LH-20柱色谱、制备型HPLC等方法对北美刺人参叶、茎进行系统分析并纯化。经理化常数、光谱学方法鉴定化合物结构。2.采用水蒸气蒸馏法提取北美刺人参叶挥发油,利用毛细管气相谱-质谱联用程序升温法对北美刺人参叶挥发油的化学成分进行了分析。
结果:
1.从北美刺人参中分离得到8个化合物,其中从北美刺人参叶中分离得4个化合物。鉴定结构分别为化合物(1):3α-hydroxy-lup-20(29)-en-23,28-dioic acid;化合物(2):3α-hydroxy-lup-20(29)-en-23,28-dioic-3-O-β-D-glucose;化合物(3):胡萝卜苷(daucosterol)和化合物(4):β-谷甾醇(β-Sitosterol)。其中化合物(2)为新化合物,化合物(1)首次在本植物中分离。从北美刺人参茎中分离得到4个化合物,鉴定结构分别为化合物(5):丁香苷(Syringin);化合物(6):腺苷(Adenosine);化合物(7):松柏苷(Coniferin);化合物(8):5′-Methoxyisolariciresinol-3α-O-β-D-glucopyranoside。以上4个化合物均为该植物中首次分离。
2.从北美刺人参叶挥发油中检出45个峰,共鉴定了44个成分,所鉴定得化学成分占挥发油总成分99.46%,其中主要成分为2-甲基-6-对甲苯基-2-庚烯(34.4%)和叶绿素醇(8.13%)。
结论:
本文利用毛细管气相色谱-质谱联用程序升温法对挥发油的化学成分进行了分析,其成分与北美刺人参茎挥发油的成分差别较大。
Purpose:To analysis chemical components of leaves of Oplopanax horridus,stem of Oplopanax horridus and volatile oil from leaves of Oplopanax horridus.
Material and method:
1.In the first part of this thesis,8 compounds were isolated from leaves and stem of Oplopanax horridus by column chromatograpy on gel silica,Sephadex LH-20,HLPC.
2.In the second part,the volatile oil was extracted from O.horridus by steam distillation and analysised by GC-MS.
Result:
1.4 componds from leaves of Oplopanax horridus(Sm.)Miq,were isolated.The 4 compounds were dentified as:3α-hydroxy-lup-20(29)-en-23,28-dioic acid(1);3α-hydroxy-lup-20(29)-en -23,28-dioic-3-O-β-D-glucose(2);daucosterol(3);β-Sitosterol(4).Compond(1) are the first time to be got from the plant.Compound(2) is a new compound.
4 componds from stem Oplopanax horridus(Sm.)Miq,were isolated.The 4 compounds wer e dentified as:Syringin(5);Adenosine(6);Coniferin(7);5'-Methoxyisolariciresinol-3α-O-β-D -glucopyranoside(8);They are the first time to be got from the plant.
2.45 compounds were separated from the volatile oil and 44 of them were identified by GC-MS analysis.Indicating the maior components in the volatile oil are 2-methyl-Methylbenzene -5-heptene(34.4%)and Phytol(8.13%).
Conclusion:
The volatile oil was extracted from Opiopanax horridus by steam distillation and analyzed by GC-MS.
The components of volatile oil from leaves of Oplopanax horridus are obviously different from the components of volatile oil from stem.
材料与方法:1.本实验利用硅胶柱色谱、Sephadex LH-20柱色谱、制备型HPLC等方法对北美刺人参叶、茎进行系统分析并纯化。经理化常数、光谱学方法鉴定化合物结构。2.采用水蒸气蒸馏法提取北美刺人参叶挥发油,利用毛细管气相谱-质谱联用程序升温法对北美刺人参叶挥发油的化学成分进行了分析。
结果:
1.从北美刺人参中分离得到8个化合物,其中从北美刺人参叶中分离得4个化合物。鉴定结构分别为化合物(1):3α-hydroxy-lup-20(29)-en-23,28-dioic acid;化合物(2):3α-hydroxy-lup-20(29)-en-23,28-dioic-3-O-β-D-glucose;化合物(3):胡萝卜苷(daucosterol)和化合物(4):β-谷甾醇(β-Sitosterol)。其中化合物(2)为新化合物,化合物(1)首次在本植物中分离。从北美刺人参茎中分离得到4个化合物,鉴定结构分别为化合物(5):丁香苷(Syringin);化合物(6):腺苷(Adenosine);化合物(7):松柏苷(Coniferin);化合物(8):5′-Methoxyisolariciresinol-3α-O-β-D-glucopyranoside。以上4个化合物均为该植物中首次分离。
2.从北美刺人参叶挥发油中检出45个峰,共鉴定了44个成分,所鉴定得化学成分占挥发油总成分99.46%,其中主要成分为2-甲基-6-对甲苯基-2-庚烯(34.4%)和叶绿素醇(8.13%)。
结论:
本文利用毛细管气相色谱-质谱联用程序升温法对挥发油的化学成分进行了分析,其成分与北美刺人参茎挥发油的成分差别较大。
Purpose:To analysis chemical components of leaves of Oplopanax horridus,stem of Oplopanax horridus and volatile oil from leaves of Oplopanax horridus.
Material and method:
1.In the first part of this thesis,8 compounds were isolated from leaves and stem of Oplopanax horridus by column chromatograpy on gel silica,Sephadex LH-20,HLPC.
2.In the second part,the volatile oil was extracted from O.horridus by steam distillation and analysised by GC-MS.
Result:
1.4 componds from leaves of Oplopanax horridus(Sm.)Miq,were isolated.The 4 compounds were dentified as:3α-hydroxy-lup-20(29)-en-23,28-dioic acid(1);3α-hydroxy-lup-20(29)-en -23,28-dioic-3-O-β-D-glucose(2);daucosterol(3);β-Sitosterol(4).Compond(1) are the first time to be got from the plant.Compound(2) is a new compound.
4 componds from stem Oplopanax horridus(Sm.)Miq,were isolated.The 4 compounds wer e dentified as:Syringin(5);Adenosine(6);Coniferin(7);5'-Methoxyisolariciresinol-3α-O-β-D -glucopyranoside(8);They are the first time to be got from the plant.
2.45 compounds were separated from the volatile oil and 44 of them were identified by GC-MS analysis.Indicating the maior components in the volatile oil are 2-methyl-Methylbenzene -5-heptene(34.4%)and Phytol(8.13%).
Conclusion:
The volatile oil was extracted from Opiopanax horridus by steam distillation and analyzed by GC-MS.
The components of volatile oil from leaves of Oplopanax horridus are obviously different from the components of volatile oil from stem.
引文
[1]李向高,帅绯,张崇禧等.刺人参中挥发油成分的分离鉴定.中国药学杂志,1990,25(3):167.
[2]Notes on Economic Plants.ECONOMIC BOTANY,2002(56):285-289.
[3]张宏桂,刘松艳,李绪文等.东北刺人参茎挥发油成分分析.自求恩医科大学学报,1994,20(1):31.
[4]张宏桂,吴广宣,张永茂等.野生东北刺人参茎挥发油化学成分研究.分析化学,1993,2(6):679.
[5]刘金平,张宏桂,吴广宣等.东北刺人参根茎脂肪酸成分对比分析.白求恩医科大学学报,1994,20(1):29.
[6]Wang Guang-Shu,etc.Studies on the Glycosides in the leaves of Oplopanax elatus Nakai(Ⅰ).Chem Res.Chin.Univ.,1994,10(3):185-192.
[7]Wang Guang-Shu,etc.Isolation and structure elucidation of new glycosides from the leaves of Oplopanax elatus Nakai(Ⅱ).Chem Res.Chin.Univ.,1994,10(4):285
[8]Wang Guang-Shu,etc.Isolation and structure elucidation of new glycosides from the leaves of Oplopanax elatus Nakai(Ⅲ).Chem Res.Chin.Univ.,1994,39(23):1969
[9]Wang Guang-Shu,etc.chemical studies on the glycosides in the leaves of Oplopanax elatus Nakai(Ⅳ).Chem Res.Chin.Univ.,1997,13(1):34.
[10]王广树,陈燕萍,徐景达等.刺人参试O和P的分离与结构鉴定.药学学报,1996,31(12):940.
[11]王广树,徐景达,村山哲也等.刺人参试Q和R的分离与结构鉴定.中国中药杂志,1997,22(2):10.
[12]王广树,徐景达,张利等.刺人参叶中配糖体的化学研究.中草药,1997,28(7):390.
[13]王广树,徐景达等.刺人参中配糖体的化学研究.中国药学杂志,1993,28(10):393.
[14]王广树,孟勤,徐景达等.刺人参中两种三萜皂苷的分离和结构鉴定.中国药学杂志,1996,31(9):523.
[15]许松,梁华清等.刺人参的葸醌成分研究.中草药,1998,59(4):222.
[16]许松,梁华清等.刺人参的化学成分研究(Ⅱ).中草药,1998,29(9):586
[17]Liu,Jian-Guo,etc.Trace elements analysis in Oplopanax of northest China.guang Dong We iliang yuansu Kwxue,1995,2(9):47.
[18]陈霞,李红,刘芬等.刺人参皂苷对大鼠血压的影响.白求恩医科大学学报,1997,23(5):475.
[19]曲淑岩,等.刺人参油对中枢神经系统的抑制作用.中草药,1984,15(6):19.
[20]傅新颖,马正俐,马之骏等.长白刺人参抗衰老实验.中国医院药学杂志,1995,15(6):122.
[21]Turner,N,J.(1982)Traditional use of Devil'sClub(Oplopanax horridus;Araliaceae) by native peoples in westem North America.Journal ofEthnobiology,2(1):17-38.
[22]曲淑岩,等.刺人参油的抗炎作用.中草药,1986,17(7):25.
[23]Mozaina Kobaisy,et al.Antimycobacterial Polyynes of Devil's Club(Oplopanax horridus),a North American Native Medcinal Plant J.Nat.Prod,1997,60:1210-1213.
[24]A.R.McCutcheon,et al.Antiviral screeing of British Colunbian medicinal plants.Journal of Ethnphamacolog,1995,49:101-110.
[25]Masatake et al.Two new Phenylpropanoid glycosides from Wikstremia sikokana.Chem.Pharm.Bull,1988,36(3):1157-1158.
[1]Phan Van Kiem,Nguyen Tien Dat,et al.Lupane-Triterpenes from the leaves of Brassaiopsis glomerulata.Arch Pharm Res.2003;26(8):594-596.
[2]Changqi Zhao,et al.Three New glycosides from Sinopodophyllum emodi(WALL.)YING.Chem.Pharm.Bull.2001;49(11):1474.
[3]Masataka Sugiyama,et al.Lignan and phenylpropanoid glycosides from Osmanthus asiaticus.Phytochemistry.1993;33(5):1215.
[4]Hans Achenbach et al.Alkaloids and other compounds from seeds of Tabernaemontana Cymosa.Phytochemistry.1997,45(2):325-335.
[5]Gilles Comte,et al.Phenylpropanoids from leaves ofJuniperusphoenicea.Phyto-chemistry.1997;45(8):1679.
[6]Seiji Yamaguchi,Toshihara Katsuki.One-step Preparation of some 2-isopropenyl-2,3-dihy dronaphtho[2,3-b]furan-4,9-diones.J Heterocyclic Chem.2001,38:511.
[7]JosephTai,Susan Cheung,Stefanie Cheah,etal.In vitro antipro-liferative and antioxidant studies on Devil's club Oplopanaxhorridus[J].Ethnopharmacology,2006,108(2):228-235.
[8]Trevor C.Lantz,Kristina Swerhun,Nancy J.Tumer.Devil's Club(Oplopanax,horridus) An Enthnobotanical Review[J].American botanical Council,2004,62:33-48.
[9]宓鹤鸣,李承祜,苏中武,等.刺人参挥发油成分及其抗真菌活性研究.药学学报,1987,22(7):549.
[10]赵月然,窦德强,等.北美刺人参挥发油的化学成分研究.辽宁中医药大学学报,2008,10(3):114-115.
[11]张宏桂,刘松艳,付爱华,等.野生东北刺人参茎挥发油成分及其抗皮肤癣菌作用.中国药学杂志,1999,34(6):369-37i.
[12]王广树.题名:中草药刺人参和牛膝中的齐墩果烷型三萜皂苷及羽扇豆烯三萜皂苷的研究.吉林:吉林大学,2006.
[2]Notes on Economic Plants.ECONOMIC BOTANY,2002(56):285-289.
[3]张宏桂,刘松艳,李绪文等.东北刺人参茎挥发油成分分析.自求恩医科大学学报,1994,20(1):31.
[4]张宏桂,吴广宣,张永茂等.野生东北刺人参茎挥发油化学成分研究.分析化学,1993,2(6):679.
[5]刘金平,张宏桂,吴广宣等.东北刺人参根茎脂肪酸成分对比分析.白求恩医科大学学报,1994,20(1):29.
[6]Wang Guang-Shu,etc.Studies on the Glycosides in the leaves of Oplopanax elatus Nakai(Ⅰ).Chem Res.Chin.Univ.,1994,10(3):185-192.
[7]Wang Guang-Shu,etc.Isolation and structure elucidation of new glycosides from the leaves of Oplopanax elatus Nakai(Ⅱ).Chem Res.Chin.Univ.,1994,10(4):285
[8]Wang Guang-Shu,etc.Isolation and structure elucidation of new glycosides from the leaves of Oplopanax elatus Nakai(Ⅲ).Chem Res.Chin.Univ.,1994,39(23):1969
[9]Wang Guang-Shu,etc.chemical studies on the glycosides in the leaves of Oplopanax elatus Nakai(Ⅳ).Chem Res.Chin.Univ.,1997,13(1):34.
[10]王广树,陈燕萍,徐景达等.刺人参试O和P的分离与结构鉴定.药学学报,1996,31(12):940.
[11]王广树,徐景达,村山哲也等.刺人参试Q和R的分离与结构鉴定.中国中药杂志,1997,22(2):10.
[12]王广树,徐景达,张利等.刺人参叶中配糖体的化学研究.中草药,1997,28(7):390.
[13]王广树,徐景达等.刺人参中配糖体的化学研究.中国药学杂志,1993,28(10):393.
[14]王广树,孟勤,徐景达等.刺人参中两种三萜皂苷的分离和结构鉴定.中国药学杂志,1996,31(9):523.
[15]许松,梁华清等.刺人参的葸醌成分研究.中草药,1998,59(4):222.
[16]许松,梁华清等.刺人参的化学成分研究(Ⅱ).中草药,1998,29(9):586
[17]Liu,Jian-Guo,etc.Trace elements analysis in Oplopanax of northest China.guang Dong We iliang yuansu Kwxue,1995,2(9):47.
[18]陈霞,李红,刘芬等.刺人参皂苷对大鼠血压的影响.白求恩医科大学学报,1997,23(5):475.
[19]曲淑岩,等.刺人参油对中枢神经系统的抑制作用.中草药,1984,15(6):19.
[20]傅新颖,马正俐,马之骏等.长白刺人参抗衰老实验.中国医院药学杂志,1995,15(6):122.
[21]Turner,N,J.(1982)Traditional use of Devil'sClub(Oplopanax horridus;Araliaceae) by native peoples in westem North America.Journal ofEthnobiology,2(1):17-38.
[22]曲淑岩,等.刺人参油的抗炎作用.中草药,1986,17(7):25.
[23]Mozaina Kobaisy,et al.Antimycobacterial Polyynes of Devil's Club(Oplopanax horridus),a North American Native Medcinal Plant J.Nat.Prod,1997,60:1210-1213.
[24]A.R.McCutcheon,et al.Antiviral screeing of British Colunbian medicinal plants.Journal of Ethnphamacolog,1995,49:101-110.
[25]Masatake et al.Two new Phenylpropanoid glycosides from Wikstremia sikokana.Chem.Pharm.Bull,1988,36(3):1157-1158.
[1]Phan Van Kiem,Nguyen Tien Dat,et al.Lupane-Triterpenes from the leaves of Brassaiopsis glomerulata.Arch Pharm Res.2003;26(8):594-596.
[2]Changqi Zhao,et al.Three New glycosides from Sinopodophyllum emodi(WALL.)YING.Chem.Pharm.Bull.2001;49(11):1474.
[3]Masataka Sugiyama,et al.Lignan and phenylpropanoid glycosides from Osmanthus asiaticus.Phytochemistry.1993;33(5):1215.
[4]Hans Achenbach et al.Alkaloids and other compounds from seeds of Tabernaemontana Cymosa.Phytochemistry.1997,45(2):325-335.
[5]Gilles Comte,et al.Phenylpropanoids from leaves ofJuniperusphoenicea.Phyto-chemistry.1997;45(8):1679.
[6]Seiji Yamaguchi,Toshihara Katsuki.One-step Preparation of some 2-isopropenyl-2,3-dihy dronaphtho[2,3-b]furan-4,9-diones.J Heterocyclic Chem.2001,38:511.
[7]JosephTai,Susan Cheung,Stefanie Cheah,etal.In vitro antipro-liferative and antioxidant studies on Devil's club Oplopanaxhorridus[J].Ethnopharmacology,2006,108(2):228-235.
[8]Trevor C.Lantz,Kristina Swerhun,Nancy J.Tumer.Devil's Club(Oplopanax,horridus) An Enthnobotanical Review[J].American botanical Council,2004,62:33-48.
[9]宓鹤鸣,李承祜,苏中武,等.刺人参挥发油成分及其抗真菌活性研究.药学学报,1987,22(7):549.
[10]赵月然,窦德强,等.北美刺人参挥发油的化学成分研究.辽宁中医药大学学报,2008,10(3):114-115.
[11]张宏桂,刘松艳,付爱华,等.野生东北刺人参茎挥发油成分及其抗皮肤癣菌作用.中国药学杂志,1999,34(6):369-37i.
[12]王广树.题名:中草药刺人参和牛膝中的齐墩果烷型三萜皂苷及羽扇豆烯三萜皂苷的研究.吉林:吉林大学,2006.