龙葵化学成分的研究
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摘要
龙葵( Solanum nigrum L. )为茄科( Solanaceace)茄属植物,又名野葡萄、老鸦眼睛草、苦菜、苦葵,为一年至多年生草本植物,在全国各地均有分布。龙葵全草均可入药,现代药理证明龙葵具有抗肿瘤、抗炎、抗休克、抗过敏、清热解毒、祛痰止咳、降压等作用。
本实验研究了龙葵叶与青果的化学成分及其主要的抗肿瘤生物活性。通过提取、分离和纯化,从龙葵叶中分离得到六个化合物,从龙葵青果中分离得到三个化合物。利用红外,紫外、质谱、一维及二维核磁等波谱手段分析鉴定了这九种成分的结构。分别为:5α,22α,25R -26-O–β-D -吡喃葡萄糖基-22-甲氧基-呋甾-3β,26-二醇-3-O–β-D -吡喃葡萄糖基-(1→2) -O -[β-D -吡喃木糖基-(1→3) ]-O–β-D -吡喃葡萄糖基-(1→4) -O–β-D -吡喃半乳糖苷(化合物L1);5α,22α,22R -26-O–β-D -吡喃葡萄糖基-22-羟基-呋甾-3β,26-二醇-3-O–β-D -吡喃葡萄糖基-(1→2) -O -[β-D -吡喃木糖基-(1→3) ]-O–β-D -吡喃葡萄糖基-(1→4) -O–β-D -吡喃半乳糖苷(化合物L2);澳洲茄边碱(化合物L3);5α,22α,25R -12-羰基--22-羟基-呋甾-26-羧基-3-O–β-D -吡喃葡萄糖基(1→4)–O-β-D -吡喃葡萄糖基-(1→2)–O-β-D -吡喃葡萄糖基-(1→4) -O–β-D -吡喃半乳糖苷(化合物L5);槲皮素-3-O-α-L-鼠李糖基-(1→4)-O-β-D-葡萄糖基-(1→6)-O-β-D-葡萄糖苷(化合物L6);5α,25R-螺甾- 3-O-β-D-吡喃木糖基-(1→3)- O-β-D-吡喃葡萄糖基-(1→2)-O-β-D-吡喃葡萄糖基-(1→4) -O-β-D -吡喃半乳糖苷(化合物L7);β-谷甾醇(化合物L8)、胡萝卜苷(化合物L9)和槲皮素(化合物L10)。其中L5、L6、L7均为首次从龙葵中分离得到。
本实验还研究了龙葵化学成分中不同组分群的抗肿瘤生物活性,研究结果表明龙葵总皂苷和龙葵总生物碱对小鼠肝癌H_(22)及Lewis肺癌的生长均具有一定的抑制作用,且呈剂量效应关系,有深入开发利用的价值。
本实验的研究结果阐明了龙葵生物活性的物质基础,为寻找龙葵全草新的医药用途提供了科学依据。
Solanum nigrum L.is one of the Solanaceae species. Also known as Ye Putao, Tulipa eye grass, bitter herbs, bitter Kui. The whole plant of Solanum nigrum can be used as medicine herbs. They were distributed throughout the whole country. Modern pharmacology clarified that they can be used for anti-tumor, anti-inflammatory and anti-shock, anti-allergic, heat and toxic, expectorant cough, antibacterial, antihypert- ensive and other effects.
In this paper, we study the chemical composition of leaves and fruit of Solanum nigrum .We discussed the extraction, separation and purification of them. Their biological anti-tumor activities have been also researched. Nine compounds were identified from Solanum nigrum L . The chemical structures of which has been elucidated by using IR, UV, MS, NMR and other spectroscopic analysis means.
L1:26-O-β-D-glucopyranosyl-(25R)-5α-furost-22α-methoxyl-3β,26-triol- 3-O-β-D-glucopyranosy(1→2 )-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyran- osyl-(1→4)-β-D-galactopyranoside , L2:26-O-β-D-glucopyranosyl-(25R)-5α-furost-3β,22α,26-triol-3-O-β-D-glucopyranosy(1→2 )-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside ,L3: Solamargine , L5:{(25R)-5α-furost-3β,22α-diol-12-one-26-carboxylic acid-3-O-β-D-glucopyranosy(1→4 )-[O-β-D- glucopyranosyl -(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside},L6: quercetin-3-O-α-L-Rhaopyranosyl(1→6 )-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside L7:tigogenin3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylo- yranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside, L5,L6,L7 is for the first time isolated from Solanum nigrum. There compounds is also isolated from the fruits. L8:β-sitsterol , L9:daucosterol , and L10: quercetin are discussed from Solanum nigrum.
This experiment also tested the anti-tumor activities of the chemical biological components.
Extraction,Separation and identification
1.Extraction and isolation
The extraction of the fruits: The dried fruit 2.5Kg, 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h,1.0h,45min. The solution was concentrated and diluted wiyh water before . flew through the AB-8, we obtained extractions(200g).
The extraction of the leaves: the dried leaves 3Kg , 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h,1.0h,45min. the solution was subjected the same manner as described as above, we obtained extractions (750g and 275g).
The separation of total flavnoids : The dried leaves 3Kg , 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h, 1.0h, 45min, the solution was concentrated, adsorbed by AB-8 resin ,eluted by 0.1% NaOH first ,the solution was neutralized by 1%HCl to pH=7, then through the AB-8 resin again. After the components were eluted by ethanol ,concentrated and dried, we obtained extractions (350g).
2 Purification
The purification of the fruits: They were separated by silica gel column chromatography with solvent (Ⅰ-Ⅰ) as mobile phase , we obtained five parts ,the further purificayion to give L4 (270mg), L5 (120mg). Using thin layer chromatography silica gel plate (prepared board), we obtained L3 (15mg).
The purification of the extracts from leaves: With sapration of silica gel column chromatography and elution (I-I), we obtained L1 (173mg). With ODS column chromatography we obtained L2 (530mg). H part with precipitation, filtration, repeatedly with methanol washing, we got L7(830mg).
The purification of flavonoids Separated with eluentⅠ-Ⅷ, collected, detected, and obtained five parts . B part with ODS column chromatography, we obtained L6 (20mg).
3 Identification
Through MS, 1DNMR, 2DNMR spectral analysis and other literature we known compounds L1:26-O-β-D-glucopyranosyl-(25R)-5α-furost-22α-methoxyl-3β, 26-triol3-O-β-D-glucopyranosy(1→2 )-[O-β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)- O-β-D-galactopyranoside .L2:26-O-β-D-glucopyranosyl -(25R)-5α-furost-3β,22α,26-triol-3-O-β-D-glucopyranosy(1→2 )-[ O-β-D- xylo- pyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)- O-β-D-galactopyranoside. L3:Solamargine ,L5:{(25R)-5α-furost-3β,22α-diol-12-one-26-carboxylic acid-3-O-β-D-glucopyranosy(1→4 )-[O-β-D- glucopyranosyl -(1→2)]- O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside}L6:quercetin-3-O-α-L-Rhaopyranosyl(1→6 )-O-β-D-gluco- pyranosyl-(1→4)-O-β-D-glucopyranoside ,L7: (25R)-5α- spirost-3-O-β-D–xylo- pyranosyl-(1→3)- O-β-D-glucopyranosyl-(1→2)- O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside. It is the first time isolated from Solanum nigrum that L8,β-sitsterol , L9,daucosterol and L10,quercetin are discussed .
The aglycone and alkaloid saponins in anti-tumor experiments
This experiment also established the total saponins and total alkaloid of Solanum nigrum in anti-tumor activities. The results showed that they both can reduce liver cancer H22 and Lewis lung cancer cells viability in dose-dependent manner.
In conclusion, all the results of the paper could provide science foundation of this medicine herb for the development and research in reason.
本实验研究了龙葵叶与青果的化学成分及其主要的抗肿瘤生物活性。通过提取、分离和纯化,从龙葵叶中分离得到六个化合物,从龙葵青果中分离得到三个化合物。利用红外,紫外、质谱、一维及二维核磁等波谱手段分析鉴定了这九种成分的结构。分别为:5α,22α,25R -26-O–β-D -吡喃葡萄糖基-22-甲氧基-呋甾-3β,26-二醇-3-O–β-D -吡喃葡萄糖基-(1→2) -O -[β-D -吡喃木糖基-(1→3) ]-O–β-D -吡喃葡萄糖基-(1→4) -O–β-D -吡喃半乳糖苷(化合物L1);5α,22α,22R -26-O–β-D -吡喃葡萄糖基-22-羟基-呋甾-3β,26-二醇-3-O–β-D -吡喃葡萄糖基-(1→2) -O -[β-D -吡喃木糖基-(1→3) ]-O–β-D -吡喃葡萄糖基-(1→4) -O–β-D -吡喃半乳糖苷(化合物L2);澳洲茄边碱(化合物L3);5α,22α,25R -12-羰基--22-羟基-呋甾-26-羧基-3-O–β-D -吡喃葡萄糖基(1→4)–O-β-D -吡喃葡萄糖基-(1→2)–O-β-D -吡喃葡萄糖基-(1→4) -O–β-D -吡喃半乳糖苷(化合物L5);槲皮素-3-O-α-L-鼠李糖基-(1→4)-O-β-D-葡萄糖基-(1→6)-O-β-D-葡萄糖苷(化合物L6);5α,25R-螺甾- 3-O-β-D-吡喃木糖基-(1→3)- O-β-D-吡喃葡萄糖基-(1→2)-O-β-D-吡喃葡萄糖基-(1→4) -O-β-D -吡喃半乳糖苷(化合物L7);β-谷甾醇(化合物L8)、胡萝卜苷(化合物L9)和槲皮素(化合物L10)。其中L5、L6、L7均为首次从龙葵中分离得到。
本实验还研究了龙葵化学成分中不同组分群的抗肿瘤生物活性,研究结果表明龙葵总皂苷和龙葵总生物碱对小鼠肝癌H_(22)及Lewis肺癌的生长均具有一定的抑制作用,且呈剂量效应关系,有深入开发利用的价值。
本实验的研究结果阐明了龙葵生物活性的物质基础,为寻找龙葵全草新的医药用途提供了科学依据。
Solanum nigrum L.is one of the Solanaceae species. Also known as Ye Putao, Tulipa eye grass, bitter herbs, bitter Kui. The whole plant of Solanum nigrum can be used as medicine herbs. They were distributed throughout the whole country. Modern pharmacology clarified that they can be used for anti-tumor, anti-inflammatory and anti-shock, anti-allergic, heat and toxic, expectorant cough, antibacterial, antihypert- ensive and other effects.
In this paper, we study the chemical composition of leaves and fruit of Solanum nigrum .We discussed the extraction, separation and purification of them. Their biological anti-tumor activities have been also researched. Nine compounds were identified from Solanum nigrum L . The chemical structures of which has been elucidated by using IR, UV, MS, NMR and other spectroscopic analysis means.
L1:26-O-β-D-glucopyranosyl-(25R)-5α-furost-22α-methoxyl-3β,26-triol- 3-O-β-D-glucopyranosy(1→2 )-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyran- osyl-(1→4)-β-D-galactopyranoside , L2:26-O-β-D-glucopyranosyl-(25R)-5α-furost-3β,22α,26-triol-3-O-β-D-glucopyranosy(1→2 )-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside ,L3: Solamargine , L5:{(25R)-5α-furost-3β,22α-diol-12-one-26-carboxylic acid-3-O-β-D-glucopyranosy(1→4 )-[O-β-D- glucopyranosyl -(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside},L6: quercetin-3-O-α-L-Rhaopyranosyl(1→6 )-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside L7:tigogenin3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylo- yranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside, L5,L6,L7 is for the first time isolated from Solanum nigrum. There compounds is also isolated from the fruits. L8:β-sitsterol , L9:daucosterol , and L10: quercetin are discussed from Solanum nigrum.
This experiment also tested the anti-tumor activities of the chemical biological components.
Extraction,Separation and identification
1.Extraction and isolation
The extraction of the fruits: The dried fruit 2.5Kg, 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h,1.0h,45min. The solution was concentrated and diluted wiyh water before . flew through the AB-8, we obtained extractions(200g).
The extraction of the leaves: the dried leaves 3Kg , 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h,1.0h,45min. the solution was subjected the same manner as described as above, we obtained extractions (750g and 275g).
The separation of total flavnoids : The dried leaves 3Kg , 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h, 1.0h, 45min, the solution was concentrated, adsorbed by AB-8 resin ,eluted by 0.1% NaOH first ,the solution was neutralized by 1%HCl to pH=7, then through the AB-8 resin again. After the components were eluted by ethanol ,concentrated and dried, we obtained extractions (350g).
2 Purification
The purification of the fruits: They were separated by silica gel column chromatography with solvent (Ⅰ-Ⅰ) as mobile phase , we obtained five parts ,the further purificayion to give L4 (270mg), L5 (120mg). Using thin layer chromatography silica gel plate (prepared board), we obtained L3 (15mg).
The purification of the extracts from leaves: With sapration of silica gel column chromatography and elution (I-I), we obtained L1 (173mg). With ODS column chromatography we obtained L2 (530mg). H part with precipitation, filtration, repeatedly with methanol washing, we got L7(830mg).
The purification of flavonoids Separated with eluentⅠ-Ⅷ, collected, detected, and obtained five parts . B part with ODS column chromatography, we obtained L6 (20mg).
3 Identification
Through MS, 1DNMR, 2DNMR spectral analysis and other literature we known compounds L1:26-O-β-D-glucopyranosyl-(25R)-5α-furost-22α-methoxyl-3β, 26-triol3-O-β-D-glucopyranosy(1→2 )-[O-β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)- O-β-D-galactopyranoside .L2:26-O-β-D-glucopyranosyl -(25R)-5α-furost-3β,22α,26-triol-3-O-β-D-glucopyranosy(1→2 )-[ O-β-D- xylo- pyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)- O-β-D-galactopyranoside. L3:Solamargine ,L5:{(25R)-5α-furost-3β,22α-diol-12-one-26-carboxylic acid-3-O-β-D-glucopyranosy(1→4 )-[O-β-D- glucopyranosyl -(1→2)]- O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside}L6:quercetin-3-O-α-L-Rhaopyranosyl(1→6 )-O-β-D-gluco- pyranosyl-(1→4)-O-β-D-glucopyranoside ,L7: (25R)-5α- spirost-3-O-β-D–xylo- pyranosyl-(1→3)- O-β-D-glucopyranosyl-(1→2)- O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside. It is the first time isolated from Solanum nigrum that L8,β-sitsterol , L9,daucosterol and L10,quercetin are discussed .
The aglycone and alkaloid saponins in anti-tumor experiments
This experiment also established the total saponins and total alkaloid of Solanum nigrum in anti-tumor activities. The results showed that they both can reduce liver cancer H22 and Lewis lung cancer cells viability in dose-dependent manner.
In conclusion, all the results of the paper could provide science foundation of this medicine herb for the development and research in reason.
引文
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