甘西鼠尾根化学成分研究
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摘要
丹参类生药具有祛瘀止痛、活血通经、清心除烦之功效。甘西鼠尾在西南、西北地区使用极为广泛，是丹参的最常见的习用品种之一，而其化学成分研究较少。为保障用药的安全、有效，以及为科学地评价其品质，我们对其化学成分进行了系统研究，并对其抗心肌缺血物质进行了跟踪筛选。
综合应用硅胶、大孔树脂、sephadexLH20、聚酰胺、反相硅胶柱层析及HPLC分离手段，对甘西鼠尾Salvia przewalskii Maxim化学成分进行了系统研究，共分得15个化合物单体，应用理化常数测定和光谱(UV，IR，MS，~1H-NMR，~(13)C-NMR，2D-NMR)分析技术鉴定了结构，分别为：丹参酮Ⅱ-A(tanshinone Ⅱ-A，Ⅰ)、隐丹参酮(crypotanshinone，Ⅱ)、紫丹参甲素(przewaquinone A，Ⅲ)、柳杉酚(sugiol，Ⅳ)、阿魏酸二十四烷酯(tetracosyl feralate，Ⅴ)、熊果酸(ursolic acid，Ⅵ)、2α，3α-二羟基乌苏-12-烯-28-酸(2α，3α-dihydroxyurs-12-ene-28-oic acid，Ⅶ)、齐墩果酸(oleanolic acid，Ⅷ)、甘西鼠尾新酮A(neo-przewaquinone A，Ⅸ)、原儿茶醛(Protocatechaldehyde，Ⅹ)、原儿茶酸(protocatechuic acid，Ⅺ)、咖啡酸(caffeic
acid，Ⅻ)、1-O-α-D-吡喃葡萄糖乙醚苷(ethyl-1-O-α-D-glucopyranoside，ⅩⅢ)、迷迭香酸(rosmarinic acid，ⅩⅣ)、丹参酚酸B(lithospermic acid B，ⅩⅤ)。其中Ⅸ为新化合物，Ⅴ、ⅩⅢ为新的天然产物Ⅱ、Ⅳ、Ⅵ、Ⅶ、Ⅷ均为首次从该植物中分得。
采用犬的冠动脉结扎造成的急性心肌梗塞模型，对甘西鼠尾的防治急性心肌梗塞和心绞痛活性部位进行筛选，获得了甘西鼠尾抗心肌缺血的活性组份群，其主要成分为迷迭香酸、丹参酚酸B、原儿茶醛、原儿茶酸、咖啡酸及1-O-α-D-吡喃葡萄糖乙醚苷。
应用HPLC法对甘西鼠尾及其它14种唇形科植物中迷迭香酸、丹参酚酸B进行了定性定量分析，结果显示，丹参酚酸B在所测植物中含量均较低；筋骨草、白苏、紫苏、甘西鼠尾、留兰香、荔枝草、皱叶薄荷、薄荷等8种植物迷迭香酸含量较高，均在1％以上，特别是筋骨草中含量高达8％以上，表明其可作为迷迭香酸的重要植物资源加以利用。
The crud drugs of Salvia miltiorrhiza Bunge (Danshen) and related plants have effects on removing stasis and alleviate pain, promoting blood circulation and promoting menstruation, clearing away heart-fire to relieve vexation. Salvia przewalskii Maxim, is a plant distributed in southwest and northwest China, where it is habitually used as one of most commonly local species using as Danshen. But its constituents were still poorly studied. To ensure the safety and effectiveness of this crud drug, we investigated systematically its constituents, and bioassayed its anti-myocardial ischemia compound.
15 compounds were isolated from the EtoH(80%) extract with column chromatography of silica gel, macroreticular resin, sephadex LH20, polyamide, reverse-phase chromatography and HPLC, and with experimental model of myocardial ischemia induced by ligating the coronary artery of dog .The compounds were identified on the basis of spectral analysis (UV, IR, MS, NMR, 2D-NMR) and phytochemical properties, These compounds identified as:t anshinone A, crypotanshinone, przewaquinone A, sugiol, tetracosyl feralate, ursolic acid, 2a,3a-dihydroxy urs-12-ene-28-acid, oleanolic acid, neo-przewaquinone A, protocatechaldehyde, protocatechuic acid, caffeic acid, ethyl-1-O-D-glucopyranoside, rosmarinic acid, lithospermic acidB. Among these compounds ,the compound is a new compound, compound, are new natural product, compound, are isolated from this plant for the first time.
The obtained active compounds having effect of anti-myocardial ischemia includes rosmarinic acid, lithospermic acid B, protocatechaldehyde, protocatechuic acid, caffeic acid and ethyl-1-O-D-glucopyranoside.
The contents of rosmarinic acid and lithospermic acid B in Salvia przewalskii Maxim, and 14 species plants (Labiatae) were determined by HPLC. The result show that the contents of lithospermic acid B in the plants are low. The contens of rosmarinic acid in 8 plants are high, which are Ajuga ciliata Bunge, Perilla frutescens (L.) Britt.(Baisu), Perilla frutescens (L.) Britt.(Zisu), Salvia przewalskii Maxim., Mentha spicata L., Salvia plebeia R.Br., Mentha haplocalyx Briq.(Zhouyebohe), Mentha haplocalyx Briq. The content .especially in Salvia plebeia R.Br. is over 8%, which means that the plant may be used as source of rosmarinic acid.
综合应用硅胶、大孔树脂、sephadexLH20、聚酰胺、反相硅胶柱层析及HPLC分离手段，对甘西鼠尾Salvia przewalskii Maxim化学成分进行了系统研究，共分得15个化合物单体，应用理化常数测定和光谱(UV，IR，MS，~1H-NMR，~(13)C-NMR，2D-NMR)分析技术鉴定了结构，分别为：丹参酮Ⅱ-A(tanshinone Ⅱ-A，Ⅰ)、隐丹参酮(crypotanshinone，Ⅱ)、紫丹参甲素(przewaquinone A，Ⅲ)、柳杉酚(sugiol，Ⅳ)、阿魏酸二十四烷酯(tetracosyl feralate，Ⅴ)、熊果酸(ursolic acid，Ⅵ)、2α，3α-二羟基乌苏-12-烯-28-酸(2α，3α-dihydroxyurs-12-ene-28-oic acid，Ⅶ)、齐墩果酸(oleanolic acid，Ⅷ)、甘西鼠尾新酮A(neo-przewaquinone A，Ⅸ)、原儿茶醛(Protocatechaldehyde，Ⅹ)、原儿茶酸(protocatechuic acid，Ⅺ)、咖啡酸(caffeic
acid，Ⅻ)、1-O-α-D-吡喃葡萄糖乙醚苷(ethyl-1-O-α-D-glucopyranoside，ⅩⅢ)、迷迭香酸(rosmarinic acid，ⅩⅣ)、丹参酚酸B(lithospermic acid B，ⅩⅤ)。其中Ⅸ为新化合物，Ⅴ、ⅩⅢ为新的天然产物Ⅱ、Ⅳ、Ⅵ、Ⅶ、Ⅷ均为首次从该植物中分得。
采用犬的冠动脉结扎造成的急性心肌梗塞模型，对甘西鼠尾的防治急性心肌梗塞和心绞痛活性部位进行筛选，获得了甘西鼠尾抗心肌缺血的活性组份群，其主要成分为迷迭香酸、丹参酚酸B、原儿茶醛、原儿茶酸、咖啡酸及1-O-α-D-吡喃葡萄糖乙醚苷。
应用HPLC法对甘西鼠尾及其它14种唇形科植物中迷迭香酸、丹参酚酸B进行了定性定量分析，结果显示，丹参酚酸B在所测植物中含量均较低；筋骨草、白苏、紫苏、甘西鼠尾、留兰香、荔枝草、皱叶薄荷、薄荷等8种植物迷迭香酸含量较高，均在1％以上，特别是筋骨草中含量高达8％以上，表明其可作为迷迭香酸的重要植物资源加以利用。
The crud drugs of Salvia miltiorrhiza Bunge (Danshen) and related plants have effects on removing stasis and alleviate pain, promoting blood circulation and promoting menstruation, clearing away heart-fire to relieve vexation. Salvia przewalskii Maxim, is a plant distributed in southwest and northwest China, where it is habitually used as one of most commonly local species using as Danshen. But its constituents were still poorly studied. To ensure the safety and effectiveness of this crud drug, we investigated systematically its constituents, and bioassayed its anti-myocardial ischemia compound.
15 compounds were isolated from the EtoH(80%) extract with column chromatography of silica gel, macroreticular resin, sephadex LH20, polyamide, reverse-phase chromatography and HPLC, and with experimental model of myocardial ischemia induced by ligating the coronary artery of dog .The compounds were identified on the basis of spectral analysis (UV, IR, MS, NMR, 2D-NMR) and phytochemical properties, These compounds identified as:t anshinone A, crypotanshinone, przewaquinone A, sugiol, tetracosyl feralate, ursolic acid, 2a,3a-dihydroxy urs-12-ene-28-acid, oleanolic acid, neo-przewaquinone A, protocatechaldehyde, protocatechuic acid, caffeic acid, ethyl-1-O-D-glucopyranoside, rosmarinic acid, lithospermic acidB. Among these compounds ,the compound is a new compound, compound, are new natural product, compound, are isolated from this plant for the first time.
The obtained active compounds having effect of anti-myocardial ischemia includes rosmarinic acid, lithospermic acid B, protocatechaldehyde, protocatechuic acid, caffeic acid and ethyl-1-O-D-glucopyranoside.
The contents of rosmarinic acid and lithospermic acid B in Salvia przewalskii Maxim, and 14 species plants (Labiatae) were determined by HPLC. The result show that the contents of lithospermic acid B in the plants are low. The contens of rosmarinic acid in 8 plants are high, which are Ajuga ciliata Bunge, Perilla frutescens (L.) Britt.(Baisu), Perilla frutescens (L.) Britt.(Zisu), Salvia przewalskii Maxim., Mentha spicata L., Salvia plebeia R.Br., Mentha haplocalyx Briq.(Zhouyebohe), Mentha haplocalyx Briq. The content .especially in Salvia plebeia R.Br. is over 8%, which means that the plant may be used as source of rosmarinic acid.
引文
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[2] 罗厚蔚，等．丹参中抑制血小板聚集的活性成分 药学学报 1988，23(11)；830-834
[3] 林隆泽，等．新二萜醌去氢丹参新酮 药学学报 1988，23(4)；273-275
[4] 杨保津，等．紫丹参中几种微量二萜结构研究 药学学报 1984，19(4)；274-281
[5] 杨保津，等．三叶鼠尾草化学成分的研究 药学学报 1982，17(4)；50
[6] Ayhan Ulubelen et al. Norditerpenoids and diterpenoids from salvia multicauliswith antituberculousactivity J Nat Prod 1997, 60(12); 1275-1280
[7] 鲁学照，等．三叶鼠尾草中小红参醌丙的结构 药学学报 1991, 26(3)；193-196
[8] 李志田，等．白花丹参化学成分的研究 药学学报 1991, 26(3)；209-213
[9] Yasuhiro Tezuka et al. Constituents of roots Salvia deserta Schang. (Xinjiang-Danshen) Chem Pharm Bull 1998, 46(1); 107-112
[10] Manuel. Jimenez E et al. A new royleanone-type diterpene from Salvia sessei J Nat Prod 1988, 51(2); 243-248
[11] Ayhan Ulubelen et al. Norditerpenoids and diterpenoids from Salvia multicaulis with antituberculousactivity J Nat Prod 1997, 60(12); 1275-1280
[12] Ayhan Ulubelen et al. diterpenoids from the roots salvia hypargeia J Nat Prod 1988, 51(6); 1178-1183
[13] 林隆泽，等．新二萜醌—红根草对醌 药学学报 1990，25(2)；154-156
[14] Yashrnasa Ikeshiro et al. Abietane type diterpenoids from salvia miltiorrhiza Phytochemistry 1989, 28(11); 3139-3141
[15] Benjamin Rodriguez et al. A rearanged abietane diterpenoid from the root of Salvia aethiopis Phytochemistry 1984, 23(8); 1805-1806
[16] 孔德云，等．丹参化学成分的研究 上海第一医学院学报 1983，10(4)； 313-315
[17] Matias Nieto et al. Icetexana and abietane diterpenoids from Salvia gilliessi
Phytochemistry 2000, 53; 911-915
[18] Antonio G. Gonzalez et al. Quinone methide diterpenoids from the roots of Salvia texana Phytochemistry 1988, 27; 1777-1781
[19] G. Topcu et al. Ditherpenoids from salvia wiedemannii Phytochemistry 1990, 29(7); 2346-2348
[20] Steven J. Dentali et al. 16-Hydroxycarnosic acid, a diterpene from salvia apiana Phytochemistry 1990, 29(3); 993-994
[21] Antonio G. Gonzalez et al. Salvicanaric acid, a new diterpene from Salvia canariensis J Nat Prod 1987, 50(3); 341-348
[22] Antonio G. Gonzalez et al. Diterpenes from salvia mellifera Phytochemistry 1991, 31 (12); 4067-4070
[23] Ayhan Ulubelen et al. Euphraticol and euphracal, two new diterpenes from Salvia euphratica J Nat Prod 1989, 52(6); 1313-1315
[24] Ayhan Ulubelen et al. Diterpenoids from the roots of Salvia hypargeia J Nat Prod 1988, 51(6); 1178-1183
[25] Ayhan Ulubelen et al. Diterpenoids and triterpenoids from Salvia multicaulis Phytochemistry 1998, 47(5); 899-901
[26] Ayhan Ulubelen et al. Salvimultine, a new noricetexane diterpene from the roots of Salviamulticaulis J Nat Prod 2000, 63(6); 879-880
[27] Miguel A. Galicia et al. Abietane diterpenoids from salvia pubescens Phytochemistry 1988, 27(1); 217-219
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