地黄叶的化学成分研究
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摘要
目的：地黄Rehmannia glutinosa Libosch为玄参科植物地黄的新鲜或者干燥块根。秋季采挖,除去芦头、须根及泥沙,鲜用；或将地黄缓缓烘焙至约八成干,前者习称“鲜地黄”,后者习称“生地黄”。地黄属植物约有6种,分布于中国、朝鲜和日本,我国南北各省区均有分布,现主要为栽培品。地黄叶为玄参科植物地黄的叶。地黄的药理学研究显示,地黄具有很强的药理活性,包括抗胃溃疡抗衰老,降血糖,降血脂,抗肿瘤,保肝等药理活性,而且本实验室通过前期试验发现地黄还具有雌激素样作用。通过对地黄叶的化学成分的研究,进一步明确其药效物质基础,寻找新的活性成分资源,为其进一步的开发利用奠定基础。
方法：
1.地黄叶的化学成分研究。干燥采收期地黄叶,粉碎后用50%含水丙酮在闪式提取器中组织破碎提取三次,合并滤液低温减压浓缩得总干粉。总干粉用水分散溶解离心,低温减压浓缩干燥得到水溶物和水不溶物。水溶物用95%乙醇分级醇沉,乙醇溶液低温减压干燥得干粉,适量水溶解上Diaion HP-20柱,依次用水、10%、20%、30%、40%、80%含水甲醇洗脱,合并各部位洗脱液低温减压浓缩得到水洗脱部位、10%甲醇洗脱部位、20%甲醇洗脱部位,30%甲醇洗脱部位,40%甲醇洗脱部位,80%甲醇洗脱部位。各洗脱部位水溶,上Toyopearl HW-40柱,甲醇-水梯度洗脱,得到的各流份再反复通过Toyopearl HW-40, Sephadex LH-20, MCI Gel CHP-20:硅胶等柱,并结合制备液相及重结晶方法,得到单体化合物。水不溶物用乙酸乙酯萃取得到萃取物40g,硅胶柱层析,二氯甲烷-甲醇(100：1,80：1,50：1)梯度洗脱,所得各流份结合Toyopearl HW-40, Sephadex LH-20, MCI Gel CHP-20等色谱柱以及重结晶方法,得到化合物。
2.采用MTT增殖拮抗实验对从地黄叶中分离得到的DHY-26-1, DHY-27, DHY-0进行体外抗肿瘤活性筛选,实验共选用了三种癌细胞,分别为人肝癌HepG2细胞,人乳腺癌MCF-7细胞,人成骨肉瘤MG63细胞。
结果：
1.本研究共从地黄叶的50%丙酮组织破碎提取物中分离并鉴定了35个化合物的结构,即对羟基苯甲酸(DHY-1),龙胆酸(DHY-2),对羟基苯乙醇(DHY-3),木犀草素-7-O-β-D-葡萄糖醛酸苷(DHY-4),6,7-二羟基香豆素(DHY-5),3,4-二羟基苯乙醇(DHY-6),1,2,4-苯三酚(DHY-7),原儿茶酸(DHY-8),6-O-香草酰基筋骨草醇(DHY-11-1), darendoside B (DHY-12-1),6-O-E-阿魏酰基筋骨草醇(DHY-13-1),去咖啡酰基毛蕊花糖苷(DHY-14-1),8-表番木鳖酸(DHY-16),梓醇(DHY-17),胡萝卜苷(DHY-18),2β,2β,19α-三羟基齐墩果-12-烯-13,28-二羧酸(DHY-19),筋骨草醇(DHY-20), β-hydroxyacteoside (DHY-22),海胆苷(DHY-24),9,12,13-三羟基-10-十八烯酸(DHY-25),3β,19α,20β,24,30-pentahy-droxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone A (DHY-26-1),3β,19α,20β,30-tetrahydroxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone B (DHY-27), glutinolic acid (DHY-28),异毛蕊花糖苷(DHY-29),焦地黄苯乙醇苷B,(DHY-30-1),毛蕊花糖苷(DHY-32),β-谷甾醇(DHY-A),木犀草素(DHY-E),香叶木素(DHY-L),芹菜素(DHY-N),齐墩果酸(DHY-H),熊果酸(DHY-F),12α,13α-epoxy-3β,19α,20β,30-tetrahydroxyurs-28-oic acid δ-lactone, Glutinosalactone C (DHY-O),齐墩果酮酸(DHY-Q),2α,3β-二羟基齐墩果-12-烯-28-酸(DHY-R)。
2.MTT增殖拮抗实验筛选三个新化合物的抗肿瘤活性,结果显示DHY-0(Glutinosalactone C)具有中等强度的抗肿瘤活性,IC50浓度为MCF-7(IC50=8.38±0.16μM), MG63(IC50=39.25±0.21μM), HepG2(IC50=17.29±2.16μM)-, DHY-26-1(Glutinosalactone A)显示微弱的抗肿瘤活性,IC50浓度为MCF-7(IC50=74.65±0.60μM), MG63(IC50=89.27±093μM), HepG2(IC50=45.36±1.62μM), DHY-27(Glutinosalactone B)没有显示对所选三种癌细胞的抗肿瘤活性。
结论：从地黄叶中分离得到3个新化合物：DHY-26-1(3β,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone A), DHY-27(3β,19α,20β,30-tetrahydroxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone B), DHY-0(12α,13α-epoxy-3β,19α,20β,30-tetrahydroxyurs-28-oic acid δ-lactone, Glutinosalactone C),另外首次从地黄中分到的已知化合物17个,它们分别为：DHY-1, DHY-2, DHY-3, DHY-4, DHY-5, DHY-6, DHY-7, DHY-8, DHY-19, DHY-22, DHY-25, DHY-L, DHY-N, DHY-H, DHY-F, DHY-Q, DHY-R。其中三萜类成分是我们首次从该植物中大量分离得到。本研究为阐明地黄叶的药效物质基础提供了科学依据,研究结果对开发利用地黄具有一定意义。
Objective:Rehmannia glutinosa Libosch belongs to the genus Rehmannia of Scrophulariaceae, of which root was important medicinal material in traditional Chinese medicine. The fresh root was called "xian di huang", and80%dry root was called "sheng di huang". Rehmannia, which consisted6species, distributes many provinces of China, as well as North Korea, and Japan. Modern pharmacological studies had shown that it had strong activities, such as anti-ulcer, anti-aging, anti-diabetic, anti-hypercholesterolemic, anti-tumor, hepato-protective activity. Rehmannia glutinosa Libosch also has estrogen-like effect as previously studies of our lab. Study of the chemical constituents of the leaves of Rehmannia glutinosa Libosch can further clarify the basis of its efficacy substances and find new active ingredient resources, which lay the foundation for its further development and utilization.
Methods:
1. The dry leaves of Rehmannia glutinosa Libosch in harvest time were extracted by50%aqueous acetone three times at room temperature and filtered. The combined extracts were concentrated under reduced pressure in a vacuum evaporator to the gross extracts. They were dissolved in water, yield the water soluble matter and the water insoluble matter, and then the water soluble matter were subjected to Diaion HP-20porous polymer resin and eluted with H2O,10%CH3OH,20%CH3OH,30%CH3OH,40%CH3OH,80%CH3OH, successively. The fractions eluted were subjected to Toyopearl HW-40column chromatography and eluted with H2O,10%CH3OH successively to afford subfractions. Then the subfractions were isolated and purified by Toyopearl HW-40, Sephadex LH-20, silica gel column chromatography, preparative liquid chromatography. The water insoluble matter were extracted with EtOAc to obtain the extract, and was chromatographed on silica gel by gradient elution with CH2C12-CH3OH(100:1,80:1,50:1), each stream seperated by Toyopearl HW-40, MCI Gel CHP-20, Sephadex LH-20column chromatography and recrystallized to give compound. The structures were identified on the basis of physiochemical characteristics and spectral methods such as IR, UV,1H-NMR,13C-NMR,1H-1H COSY, DEPT-135, HMBC, HSQC and so on.
2. The MTT assay was used for the quantitative determination of cellular proliferation. The following human tumor cell lines were used: MCF-7(human breast cancer cells), MG63(human osteoblast-like cells), HepG2(human hepatocellular carcinoma cells). The cytotoxicity in vitro of the three new compounds Glutinosalactone A-C isolated from leaves of Rehmannia glutinosa Libosch were tested.
Results:
1.35compounds were isolated from leaves of Rehmannia glutinosa Libosch and the structures were elucidated by spectroscopic and chemical methods. They were p-hyoxybenzoic acid (DHY-1), gentisic acid (DHY-2), p-hydroxyphenylethyl alcohol (DHY-3), luteolin-7-O-β-D-glucuronide (DHY-2),6,7-dihydroxy-coumarin (DHY-5),3,4-dihydroxyphenylethyl alcohol (DHY-6),1,2,4-benzenetri (DHY-7), protocatechuic acid (DHY-8),6-O-vanillate ajugol (DHY-11-1), darendoside B (DHY-12-1),6-O-E-feruloyl ajugol (DHY-13-1), decaffeoylacteoside (DHY-14-1),8-epiloganic acid (DHY-16), catalpol (DHY-17), daucosterol (DHY-18),2β,3β,19α-trihydroxyolean-12-ene-13,28-dioic acid (DHY-19), ajugol (DHY-20), β-hydroxyacteoside (DHY-22), echinacoside (DHY-24),9,12,13-trihydroxy-10-octadecenoic acid (DHY-25),3β,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid δ-lactone (DHY-26-1),3β,19α,20β,30-tetrahydroxyurs-12-en-28-oic acid δ-lactone (DHY- 27), glutinolic acid (DHY-28), acteoside isomer (DHY-29), jionoside B1(DHY-30-1), acteoside (DHY-32), β-sitosterol (DHY-A), luteolin (DHY-E), diosmetin (DHY-L), apigenin (DHY-N), oleanolic acid (DHY-H), ursolic acid (DHY-F),12a,13α-epoxy-3β,19α,20β,30-tetrahydroxyurs-28-oic acid (5-lactone (DHY-O), oleanonic acid (DHY-Q),2α,3β-dihydroxyolean-12-ene-28-oic acid (DHY-R).
2. The MTT assay was used for the quantitative determination of cellular proliferation, and DHY-0(Glutinosalactone C) exhibited moderate cytotoxicity against MCF-7(IC50=8.38±0.16μM), MG63(IC50=39.25±0.21μM), HepG2(IC50=17.29±2.16μM). DHY-26-1(Glutinosalactone A) shows weak cytotoxicity against MCF-7(IC50=74.65±0.60nM), MG63(IC50=89.27±093μM) and HepG2(IC50=45.36±1.62μM), DHY-B (Glutinosalactone B) showed no cytotoxicity of the selected three kinds of cancer cells.
Conclusions: Three new compounds, DHY-26-1(Glutinosa-lactone A), DHY-27(Glutinosalactone B), DHY-0(Glutinosalactone C) were isolated from the leaves of Rehmannia glutinosa Libosch. The other seventeen known compounds DHY-1, DHY-2, DHY-3, DHY-4, DHY-5, DHY-6, DHY-7, DHY-8, DHY-19, DHY-22, DHY-25, DHY-L, DHY-N, DHY-H, DHY-F, DHY-Q, DHY-R were isolated from this plant for the first time.Triterpenoids isolated from this plant for the first time. This study provided sciebtific basis for the fundamental research of Rehmannia glutinosa Libosch.
方法：
1.地黄叶的化学成分研究。干燥采收期地黄叶,粉碎后用50%含水丙酮在闪式提取器中组织破碎提取三次,合并滤液低温减压浓缩得总干粉。总干粉用水分散溶解离心,低温减压浓缩干燥得到水溶物和水不溶物。水溶物用95%乙醇分级醇沉,乙醇溶液低温减压干燥得干粉,适量水溶解上Diaion HP-20柱,依次用水、10%、20%、30%、40%、80%含水甲醇洗脱,合并各部位洗脱液低温减压浓缩得到水洗脱部位、10%甲醇洗脱部位、20%甲醇洗脱部位,30%甲醇洗脱部位,40%甲醇洗脱部位,80%甲醇洗脱部位。各洗脱部位水溶,上Toyopearl HW-40柱,甲醇-水梯度洗脱,得到的各流份再反复通过Toyopearl HW-40, Sephadex LH-20, MCI Gel CHP-20:硅胶等柱,并结合制备液相及重结晶方法,得到单体化合物。水不溶物用乙酸乙酯萃取得到萃取物40g,硅胶柱层析,二氯甲烷-甲醇(100：1,80：1,50：1)梯度洗脱,所得各流份结合Toyopearl HW-40, Sephadex LH-20, MCI Gel CHP-20等色谱柱以及重结晶方法,得到化合物。
2.采用MTT增殖拮抗实验对从地黄叶中分离得到的DHY-26-1, DHY-27, DHY-0进行体外抗肿瘤活性筛选,实验共选用了三种癌细胞,分别为人肝癌HepG2细胞,人乳腺癌MCF-7细胞,人成骨肉瘤MG63细胞。
结果：
1.本研究共从地黄叶的50%丙酮组织破碎提取物中分离并鉴定了35个化合物的结构,即对羟基苯甲酸(DHY-1),龙胆酸(DHY-2),对羟基苯乙醇(DHY-3),木犀草素-7-O-β-D-葡萄糖醛酸苷(DHY-4),6,7-二羟基香豆素(DHY-5),3,4-二羟基苯乙醇(DHY-6),1,2,4-苯三酚(DHY-7),原儿茶酸(DHY-8),6-O-香草酰基筋骨草醇(DHY-11-1), darendoside B (DHY-12-1),6-O-E-阿魏酰基筋骨草醇(DHY-13-1),去咖啡酰基毛蕊花糖苷(DHY-14-1),8-表番木鳖酸(DHY-16),梓醇(DHY-17),胡萝卜苷(DHY-18),2β,2β,19α-三羟基齐墩果-12-烯-13,28-二羧酸(DHY-19),筋骨草醇(DHY-20), β-hydroxyacteoside (DHY-22),海胆苷(DHY-24),9,12,13-三羟基-10-十八烯酸(DHY-25),3β,19α,20β,24,30-pentahy-droxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone A (DHY-26-1),3β,19α,20β,30-tetrahydroxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone B (DHY-27), glutinolic acid (DHY-28),异毛蕊花糖苷(DHY-29),焦地黄苯乙醇苷B,(DHY-30-1),毛蕊花糖苷(DHY-32),β-谷甾醇(DHY-A),木犀草素(DHY-E),香叶木素(DHY-L),芹菜素(DHY-N),齐墩果酸(DHY-H),熊果酸(DHY-F),12α,13α-epoxy-3β,19α,20β,30-tetrahydroxyurs-28-oic acid δ-lactone, Glutinosalactone C (DHY-O),齐墩果酮酸(DHY-Q),2α,3β-二羟基齐墩果-12-烯-28-酸(DHY-R)。
2.MTT增殖拮抗实验筛选三个新化合物的抗肿瘤活性,结果显示DHY-0(Glutinosalactone C)具有中等强度的抗肿瘤活性,IC50浓度为MCF-7(IC50=8.38±0.16μM), MG63(IC50=39.25±0.21μM), HepG2(IC50=17.29±2.16μM)-, DHY-26-1(Glutinosalactone A)显示微弱的抗肿瘤活性,IC50浓度为MCF-7(IC50=74.65±0.60μM), MG63(IC50=89.27±093μM), HepG2(IC50=45.36±1.62μM), DHY-27(Glutinosalactone B)没有显示对所选三种癌细胞的抗肿瘤活性。
结论：从地黄叶中分离得到3个新化合物：DHY-26-1(3β,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone A), DHY-27(3β,19α,20β,30-tetrahydroxyurs-12-en-28-oic acid δ-lactone, Glutinosalactone B), DHY-0(12α,13α-epoxy-3β,19α,20β,30-tetrahydroxyurs-28-oic acid δ-lactone, Glutinosalactone C),另外首次从地黄中分到的已知化合物17个,它们分别为：DHY-1, DHY-2, DHY-3, DHY-4, DHY-5, DHY-6, DHY-7, DHY-8, DHY-19, DHY-22, DHY-25, DHY-L, DHY-N, DHY-H, DHY-F, DHY-Q, DHY-R。其中三萜类成分是我们首次从该植物中大量分离得到。本研究为阐明地黄叶的药效物质基础提供了科学依据,研究结果对开发利用地黄具有一定意义。
Objective:Rehmannia glutinosa Libosch belongs to the genus Rehmannia of Scrophulariaceae, of which root was important medicinal material in traditional Chinese medicine. The fresh root was called "xian di huang", and80%dry root was called "sheng di huang". Rehmannia, which consisted6species, distributes many provinces of China, as well as North Korea, and Japan. Modern pharmacological studies had shown that it had strong activities, such as anti-ulcer, anti-aging, anti-diabetic, anti-hypercholesterolemic, anti-tumor, hepato-protective activity. Rehmannia glutinosa Libosch also has estrogen-like effect as previously studies of our lab. Study of the chemical constituents of the leaves of Rehmannia glutinosa Libosch can further clarify the basis of its efficacy substances and find new active ingredient resources, which lay the foundation for its further development and utilization.
Methods:
1. The dry leaves of Rehmannia glutinosa Libosch in harvest time were extracted by50%aqueous acetone three times at room temperature and filtered. The combined extracts were concentrated under reduced pressure in a vacuum evaporator to the gross extracts. They were dissolved in water, yield the water soluble matter and the water insoluble matter, and then the water soluble matter were subjected to Diaion HP-20porous polymer resin and eluted with H2O,10%CH3OH,20%CH3OH,30%CH3OH,40%CH3OH,80%CH3OH, successively. The fractions eluted were subjected to Toyopearl HW-40column chromatography and eluted with H2O,10%CH3OH successively to afford subfractions. Then the subfractions were isolated and purified by Toyopearl HW-40, Sephadex LH-20, silica gel column chromatography, preparative liquid chromatography. The water insoluble matter were extracted with EtOAc to obtain the extract, and was chromatographed on silica gel by gradient elution with CH2C12-CH3OH(100:1,80:1,50:1), each stream seperated by Toyopearl HW-40, MCI Gel CHP-20, Sephadex LH-20column chromatography and recrystallized to give compound. The structures were identified on the basis of physiochemical characteristics and spectral methods such as IR, UV,1H-NMR,13C-NMR,1H-1H COSY, DEPT-135, HMBC, HSQC and so on.
2. The MTT assay was used for the quantitative determination of cellular proliferation. The following human tumor cell lines were used: MCF-7(human breast cancer cells), MG63(human osteoblast-like cells), HepG2(human hepatocellular carcinoma cells). The cytotoxicity in vitro of the three new compounds Glutinosalactone A-C isolated from leaves of Rehmannia glutinosa Libosch were tested.
Results:
1.35compounds were isolated from leaves of Rehmannia glutinosa Libosch and the structures were elucidated by spectroscopic and chemical methods. They were p-hyoxybenzoic acid (DHY-1), gentisic acid (DHY-2), p-hydroxyphenylethyl alcohol (DHY-3), luteolin-7-O-β-D-glucuronide (DHY-2),6,7-dihydroxy-coumarin (DHY-5),3,4-dihydroxyphenylethyl alcohol (DHY-6),1,2,4-benzenetri (DHY-7), protocatechuic acid (DHY-8),6-O-vanillate ajugol (DHY-11-1), darendoside B (DHY-12-1),6-O-E-feruloyl ajugol (DHY-13-1), decaffeoylacteoside (DHY-14-1),8-epiloganic acid (DHY-16), catalpol (DHY-17), daucosterol (DHY-18),2β,3β,19α-trihydroxyolean-12-ene-13,28-dioic acid (DHY-19), ajugol (DHY-20), β-hydroxyacteoside (DHY-22), echinacoside (DHY-24),9,12,13-trihydroxy-10-octadecenoic acid (DHY-25),3β,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid δ-lactone (DHY-26-1),3β,19α,20β,30-tetrahydroxyurs-12-en-28-oic acid δ-lactone (DHY- 27), glutinolic acid (DHY-28), acteoside isomer (DHY-29), jionoside B1(DHY-30-1), acteoside (DHY-32), β-sitosterol (DHY-A), luteolin (DHY-E), diosmetin (DHY-L), apigenin (DHY-N), oleanolic acid (DHY-H), ursolic acid (DHY-F),12a,13α-epoxy-3β,19α,20β,30-tetrahydroxyurs-28-oic acid (5-lactone (DHY-O), oleanonic acid (DHY-Q),2α,3β-dihydroxyolean-12-ene-28-oic acid (DHY-R).
2. The MTT assay was used for the quantitative determination of cellular proliferation, and DHY-0(Glutinosalactone C) exhibited moderate cytotoxicity against MCF-7(IC50=8.38±0.16μM), MG63(IC50=39.25±0.21μM), HepG2(IC50=17.29±2.16μM). DHY-26-1(Glutinosalactone A) shows weak cytotoxicity against MCF-7(IC50=74.65±0.60nM), MG63(IC50=89.27±093μM) and HepG2(IC50=45.36±1.62μM), DHY-B (Glutinosalactone B) showed no cytotoxicity of the selected three kinds of cancer cells.
Conclusions: Three new compounds, DHY-26-1(Glutinosa-lactone A), DHY-27(Glutinosalactone B), DHY-0(Glutinosalactone C) were isolated from the leaves of Rehmannia glutinosa Libosch. The other seventeen known compounds DHY-1, DHY-2, DHY-3, DHY-4, DHY-5, DHY-6, DHY-7, DHY-8, DHY-19, DHY-22, DHY-25, DHY-L, DHY-N, DHY-H, DHY-F, DHY-Q, DHY-R were isolated from this plant for the first time.Triterpenoids isolated from this plant for the first time. This study provided sciebtific basis for the fundamental research of Rehmannia glutinosa Libosch.
引文
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