蓝布正的化学成分及质量控制研究
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摘要
蓝布正(贵州),又名追风七(陕西),是蔷薇科(Rosaceae)路边青属(Geum)植物柔毛路边青(Geum japonicum Thunb. var. chinense F. Bolle)的干燥全草。该属植物全世界约有70种,其中我国仅有路边青(G. aleppicum)、紫萼路边青(G. rivale)、日本路边青(G. japonicum)和柔毛路边青(G. japonicum Thunb. var. chinense F. Bolle)4种。蓝布正生长于山坡草地、沟边、底边、河滩、林间隙地及林缘。海拔200-3500米。民间多作为利尿剂和收敛剂使用。
截至目前文献报道中从蓝布正中分离得到了一些乌苏烷型三萜类、甾体类以及鞣质类化合物。蓝布正曾收载于1977年版《中国药典》,但仅对其进行了性状描述,鉴别方法缺乏专一性,无显微鉴别和含量测定方法。因此,从基础研究和应用研究的角度来看,都有必要对蓝布正进行系统的质量控制标准的制定、化学成分研究,从而更好的对蓝布正进行开发利用。
本课题以2007年7月采自贵州花溪高坡乡的蓝布正为研究对象,对其各部分运用各种分离纯化技术进行系统的化学成分分离,从中得到33个化合物,并且采用现代波谱技术(ESI-MS, HRESI-MS, IR, 1H-NMR, 13C-NMR, DEPT和2D-NMR等)对这些化合物进行了结构鉴定。鉴定结果如下: *GC-1: 20?,28-epoxy-28-hydroxytaraxasteran-3?-ol GC-2: ?-谷甾醇GC-3:胡萝卜苷GC-4: ?-生育醌GC-5: 3'-O-methyl-3,4-methylenedioxo ellagic acidGC-6: 3,3'-二甲基鞣花酸GC-7:罗布麻宁GC-8:黑麦草内酯GC-9: 7-差向黑麦草内酯GC-10:对羟基桂皮酸GC-11:没食子酸乙酯GC-12: megastigman-7-ene-3,5,6,9-tetrol GC-13:熊果酸GC-14: 1?,2?,19?-三羟基-3-羰基-12-烯-28-乌苏酸GC-15: 3-O-trans-p-coumaroyltormentic acid GC-16:委陵菜酸GC-17: 2?,3?,19?,23-tetrahydroxy-12-ursen-28-oic-acid GC-18: 28-?-D-glucoside-2?, 3?, 19?-trihydroxy-12-ursen-28-oic acid *GC-19: (7R,8R)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5'- trimethoxy-8-O-4'- neolignan *GC-20: (7R,8S)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5'- trimethoxy-8-O-4'- neolignan GC-21:仙鹤草内酯-6-O-?-D-葡萄吡喃糖苷GC-22:山奈酚香豆酰基葡萄吡喃糖甙GC-23:没食子酸GC-24: kaempferol 3-O-(6''-O-Z-p-coumaroyl)-?-D-glucopyranoside GC-25:紫云英苷GC-26:槲皮素GC-27:鞣花酸GC-28: 3'-O-methyl-3,4-O,O-metheneellagic acid-4'-O-?-D- glucopynanoside GC-29: 3,3'-二甲基鞣花酸-4'-O-?-D-葡萄糖苷
GC-30: nigaichigoside F1 GC-31: cupressoside A GC-32: (7R,8S)-3-methoxy-3',7-epoxy-8,4'-oxyneoligna-4,9,9'-triol-9'- O-?-L-rhamnopyranoside *GC-33: (7S,8S)-5-methoxycupressoside A
分离得到的33个化合物中,包括三萜及甾体类10个,木脂素类5个,没食子酸及鞣花酸衍生物7个,黄酮类4个,其他类7个,其中1个新的三萜类化合物GC-1,3个新的木脂素类化合物GC-19、GC-20、GC-33。上述4个新化合物及另外2个木脂素类化合物GC-31、GC-32均为首次从该属植物中分离得到。
为了对蓝布正进行质量控制研究,我们收集了贵州、云南和四川等地十个不同产地的样品,经对照《中国植物志》的性状描述进行鉴定,所采样品包括了药材的两个植物来源路边青和柔毛路边青。我们对药材的性状、显微鉴别、TLC鉴别、水分、灰分、酸不溶性灰分、浸出物和以没食子酸为指标的含量测定项目进行了增补。
此外,对所有化合物进行了对RAW264.7巨噬细胞NO代谢影响的抗炎活性研究,实验显示只有少量适度活性被检测到。
Geum japonicum Thunb. var. chinense F. Bolle belongs to the family Rosaceae, genus Geum which comprises ca. 70 species of plants, four of which are found in China. It is commonly known as“Lanbuzheng”, widely distributed in China growing at 200-3500 m above sea level. It has been used as a herbal medicine in diuretics and astringents.
Previous investigations on G. japonicum revealed the presence of ursane-type triterpenoids, sterols, and tannins. It had been documented in the Chinese Pharmacopoeia 1977 in which there were only characters description and identification. Therefore, it is necessary to study the chemical constituents and quality control of G. japonicum.
In this study, we investigated the chemical constituents of G. japonicum, which were collected from Gaopo country, Guizhou province, in July 2007. Thirty-three compounds were obtained by various chromatographic methods including silica gel column chromatography, Sephadex LH-20 column chromatography and preparative-HPLC, the structures of all compounds were identified by the spectroscopic analysis (ESI-MS, HRESI-MS, IR, 1H-NMR, 13C-NMR and 2D-NMR), or by comparing their spectral data with those published in literatures. These compounds were identified as follows: *GC-1: 20?,28-epoxy-28-hydroxytaraxasteran-3?-ol GC-2: ?-sitosterol GC-3: daucosterol GC-4: ?-tocoquinone GC-5: 3'-O-methyl-3,4-methylenedioxo ellagic acid GC-6: 3,3'-di-O-methylellagic acid GC-7: apocynin GC-8: loliolide GC-9: isololiolide GC-10: p-hydroxycinnamic acid GC-11: progallin A GC-12: megastigman-7-ene-3,5,6,9-tetrol GC-13: ursolic acid GC-14: 1?,2?,19?-trihydroxy-3-oxo-12-ursen-28-oic acid GC-15: 3-O-trans-p-coumaroyltormentic acid GC-16: tormentic acid GC-17: 2?,3?,19?,23-tetrahydroxy-12-ursen-28-oic-acid GC-18: 28-?-D-glucoside-2?,3?,19?-trihydroxy-12-ursen-28-oic acid *GC-19: (7R,8R)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5' -trimethoxy-8-O-4'-neolignan
*GC-20: (7R,8S)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5' -trimethoxy-8-O-4'-neolignan GC-21: agrimonolide 6-O-?-D-glucoside GC-22: tiliroside GC-23: gallic acid GC-24: kaempferol 3-O-(6''-O-Z-p-coumaroyl)-?-D- glucopyranoside GC-25: kaempferol 3-O-?-D-glucopyranoside GC-26: quercetin GC-27: ellagic acid GC-28: 3'-O-methyl-3,4-O,O-metheneellagic acid-4'-O-?-D- glucopynanoside GC-29: 3,3'-di-O-methylellagic acid-4'-O-?-D-glucopyranoside GC-30: nigaichigoside F1 GC-31: cupressoside A GC-32: (7R,8S)-3-methoxy-3',7-epoxy-8,4'-oxyneoligna-4,9,9'- triol-9'-O-?-L-rhamnopyranoside *GC-33: (7S,8S)-5-methoxycupressoside A
Phytochemical investigation of the whole plants of G. japonicum afforded one new taraxasterane-type triterpene (GC-1), three new neoligans (GC-19, GC-20, GC-33), and twenty-nine other known compounds. GC-1, GC-19, GC-20, GC-31, GC-32 and GC-33 are reported for the first time from Geum genus.
In order to study the quality control of G. japonicum, we collected ten samples from different areas such as Guizhou, Yunnan and Sichuan Province. These plants were identified as G. aleppicum and G. japonicum by comparing the flora of China. The traits of G. japonicum, microscopic identification, TLC identification, moisture content, ash content, acid-insoluble ash, extracts and content determination by Gallic acid were added to Chinese Pharmacopoeia 2010.
Moreover, all compounds were evaluated for anti-inflammatory activities against NO production in RAW264.7 macrophages, and only moderate activities were detected.
截至目前文献报道中从蓝布正中分离得到了一些乌苏烷型三萜类、甾体类以及鞣质类化合物。蓝布正曾收载于1977年版《中国药典》,但仅对其进行了性状描述,鉴别方法缺乏专一性,无显微鉴别和含量测定方法。因此,从基础研究和应用研究的角度来看,都有必要对蓝布正进行系统的质量控制标准的制定、化学成分研究,从而更好的对蓝布正进行开发利用。
本课题以2007年7月采自贵州花溪高坡乡的蓝布正为研究对象,对其各部分运用各种分离纯化技术进行系统的化学成分分离,从中得到33个化合物,并且采用现代波谱技术(ESI-MS, HRESI-MS, IR, 1H-NMR, 13C-NMR, DEPT和2D-NMR等)对这些化合物进行了结构鉴定。鉴定结果如下: *GC-1: 20?,28-epoxy-28-hydroxytaraxasteran-3?-ol GC-2: ?-谷甾醇GC-3:胡萝卜苷GC-4: ?-生育醌GC-5: 3'-O-methyl-3,4-methylenedioxo ellagic acidGC-6: 3,3'-二甲基鞣花酸GC-7:罗布麻宁GC-8:黑麦草内酯GC-9: 7-差向黑麦草内酯GC-10:对羟基桂皮酸GC-11:没食子酸乙酯GC-12: megastigman-7-ene-3,5,6,9-tetrol GC-13:熊果酸GC-14: 1?,2?,19?-三羟基-3-羰基-12-烯-28-乌苏酸GC-15: 3-O-trans-p-coumaroyltormentic acid GC-16:委陵菜酸GC-17: 2?,3?,19?,23-tetrahydroxy-12-ursen-28-oic-acid GC-18: 28-?-D-glucoside-2?, 3?, 19?-trihydroxy-12-ursen-28-oic acid *GC-19: (7R,8R)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5'- trimethoxy-8-O-4'- neolignan *GC-20: (7R,8S)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5'- trimethoxy-8-O-4'- neolignan GC-21:仙鹤草内酯-6-O-?-D-葡萄吡喃糖苷GC-22:山奈酚香豆酰基葡萄吡喃糖甙GC-23:没食子酸GC-24: kaempferol 3-O-(6''-O-Z-p-coumaroyl)-?-D-glucopyranoside GC-25:紫云英苷GC-26:槲皮素GC-27:鞣花酸GC-28: 3'-O-methyl-3,4-O,O-metheneellagic acid-4'-O-?-D- glucopynanoside GC-29: 3,3'-二甲基鞣花酸-4'-O-?-D-葡萄糖苷
GC-30: nigaichigoside F1 GC-31: cupressoside A GC-32: (7R,8S)-3-methoxy-3',7-epoxy-8,4'-oxyneoligna-4,9,9'-triol-9'- O-?-L-rhamnopyranoside *GC-33: (7S,8S)-5-methoxycupressoside A
分离得到的33个化合物中,包括三萜及甾体类10个,木脂素类5个,没食子酸及鞣花酸衍生物7个,黄酮类4个,其他类7个,其中1个新的三萜类化合物GC-1,3个新的木脂素类化合物GC-19、GC-20、GC-33。上述4个新化合物及另外2个木脂素类化合物GC-31、GC-32均为首次从该属植物中分离得到。
为了对蓝布正进行质量控制研究,我们收集了贵州、云南和四川等地十个不同产地的样品,经对照《中国植物志》的性状描述进行鉴定,所采样品包括了药材的两个植物来源路边青和柔毛路边青。我们对药材的性状、显微鉴别、TLC鉴别、水分、灰分、酸不溶性灰分、浸出物和以没食子酸为指标的含量测定项目进行了增补。
此外,对所有化合物进行了对RAW264.7巨噬细胞NO代谢影响的抗炎活性研究,实验显示只有少量适度活性被检测到。
Geum japonicum Thunb. var. chinense F. Bolle belongs to the family Rosaceae, genus Geum which comprises ca. 70 species of plants, four of which are found in China. It is commonly known as“Lanbuzheng”, widely distributed in China growing at 200-3500 m above sea level. It has been used as a herbal medicine in diuretics and astringents.
Previous investigations on G. japonicum revealed the presence of ursane-type triterpenoids, sterols, and tannins. It had been documented in the Chinese Pharmacopoeia 1977 in which there were only characters description and identification. Therefore, it is necessary to study the chemical constituents and quality control of G. japonicum.
In this study, we investigated the chemical constituents of G. japonicum, which were collected from Gaopo country, Guizhou province, in July 2007. Thirty-three compounds were obtained by various chromatographic methods including silica gel column chromatography, Sephadex LH-20 column chromatography and preparative-HPLC, the structures of all compounds were identified by the spectroscopic analysis (ESI-MS, HRESI-MS, IR, 1H-NMR, 13C-NMR and 2D-NMR), or by comparing their spectral data with those published in literatures. These compounds were identified as follows: *GC-1: 20?,28-epoxy-28-hydroxytaraxasteran-3?-ol GC-2: ?-sitosterol GC-3: daucosterol GC-4: ?-tocoquinone GC-5: 3'-O-methyl-3,4-methylenedioxo ellagic acid GC-6: 3,3'-di-O-methylellagic acid GC-7: apocynin GC-8: loliolide GC-9: isololiolide GC-10: p-hydroxycinnamic acid GC-11: progallin A GC-12: megastigman-7-ene-3,5,6,9-tetrol GC-13: ursolic acid GC-14: 1?,2?,19?-trihydroxy-3-oxo-12-ursen-28-oic acid GC-15: 3-O-trans-p-coumaroyltormentic acid GC-16: tormentic acid GC-17: 2?,3?,19?,23-tetrahydroxy-12-ursen-28-oic-acid GC-18: 28-?-D-glucoside-2?,3?,19?-trihydroxy-12-ursen-28-oic acid *GC-19: (7R,8R)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5' -trimethoxy-8-O-4'-neolignan
*GC-20: (7R,8S)-4-hydroxy-9'-O-(?-L-rhamnopyranosyl)-3,3',5' -trimethoxy-8-O-4'-neolignan GC-21: agrimonolide 6-O-?-D-glucoside GC-22: tiliroside GC-23: gallic acid GC-24: kaempferol 3-O-(6''-O-Z-p-coumaroyl)-?-D- glucopyranoside GC-25: kaempferol 3-O-?-D-glucopyranoside GC-26: quercetin GC-27: ellagic acid GC-28: 3'-O-methyl-3,4-O,O-metheneellagic acid-4'-O-?-D- glucopynanoside GC-29: 3,3'-di-O-methylellagic acid-4'-O-?-D-glucopyranoside GC-30: nigaichigoside F1 GC-31: cupressoside A GC-32: (7R,8S)-3-methoxy-3',7-epoxy-8,4'-oxyneoligna-4,9,9'- triol-9'-O-?-L-rhamnopyranoside *GC-33: (7S,8S)-5-methoxycupressoside A
Phytochemical investigation of the whole plants of G. japonicum afforded one new taraxasterane-type triterpene (GC-1), three new neoligans (GC-19, GC-20, GC-33), and twenty-nine other known compounds. GC-1, GC-19, GC-20, GC-31, GC-32 and GC-33 are reported for the first time from Geum genus.
In order to study the quality control of G. japonicum, we collected ten samples from different areas such as Guizhou, Yunnan and Sichuan Province. These plants were identified as G. aleppicum and G. japonicum by comparing the flora of China. The traits of G. japonicum, microscopic identification, TLC identification, moisture content, ash content, acid-insoluble ash, extracts and content determination by Gallic acid were added to Chinese Pharmacopoeia 2010.
Moreover, all compounds were evaluated for anti-inflammatory activities against NO production in RAW264.7 macrophages, and only moderate activities were detected.
引文
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