中药龙葵抗癌活性成分研究
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摘要
本文通过S180荷瘤小鼠体内实验研究了中药龙葵(Solanum nigrum)全草乙醇提取物中的总皂苷部分的抗癌活性，初步试验表明龙葵总皂苷有抗癌作用，且表现出一定的量效关系。
通过综合运用D-101大孔吸附树脂、硅胶柱色谱、ODS柱色谱、Sephadex LH-20柱色谱以及制备型反相HPLC等多种色谱学分离手段，对龙葵乙醇提取物的总皂苷部分的化学成分进行了系统研究，从中分离得到43个化合物。利用理化性质、现代光谱学(IR、MS、~1H-NMR、~(13)C-NMR和2D-NMR)以及化学沟通(酸水解，Mosher法)等手段鉴定了它们的结构，分别为：solasonine (1),β_1-solasonine (2),β_2-solasonine (3), solamargine (4),β_2-solamargine (5),solanigroside P (6)~*, solanigroside Q (7)~*, (3β, 12β, 22α, 25R)-3,12-dihydroxy-spirosol-5-en-27-oic acid(8), hypoglaucin H(9), dumoside(10), degalactotigonin(11), tigogenin 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside(12), nigrumninⅠ(13), solanigroside C (14)~*,solanigroside D (15)~*, solanigroside E (16)~*, solanigroside F (17)~*, solanigroside G (18)~*,solanigroside H (19)~*, uttroside B (20), uttroside A (21), (22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furost-△~5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (22), (22α,25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-△~5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4).-O-β-D-galac-topyranoside (23), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furostan-3β,26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4).-O-β-D-galactopyranoside (24), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (25), solanigrosideⅠ(26)~*, solanigrosideJ (27)~*, solanigroside K (28)~*, solanigroside L (29)~*, solanigroside M (30)~*, solanigroside N(31)~*, solanigroside O (32)~*, solanigroside R (33)~*, solanigroside S (34)~*, solanigroside T (35)~*,5α-pregn-16-en-3β-ol-20-one lycotetraoside (36), solanigroside A (37)~*, solanigroside B (38)~*,(5α, 20S)-3β, 16β-dihydroxy pregn-22-carboxylic acid (22, 16)-lactone-3-(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylpyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (39), solanigroside U (40)~*, solanigroside V (41)~*, solanigroside W (42)~*,solanigroside X(43)~*。43个化合物中包括42个甾体皂苷类化合物和一个甾体皂苷元。其中，8个化合物分子中含有N原子，为生物碱型甾体皂苷类化合物，35个化合物分子中不含有N原子，为非生物碱型甾体皂苷类化合物。另外，有24个化合物(6、7、14-19、26-35、37、38、40-43)为新化合物，8个化合物(9、10、22-25、36、39)为首次从该属中分离得到，2个化合物(2、3)为首次从该种中分离得到。这些化合物中还包含了9种未见文献报道的全新苷元的糖苷(28-35，42)。
采用HPLC-ELSD方法建立了龙葵总皂苷标准提取物(活性部位)的指纹图谱，并用分离得到的11个化合物(30、25、20、31、17、36、15、4、12、13)为对照品，对标准提取物中峰面积占85％以上的峰进行了指认，测定了2个主要皂苷(11，20)的含量。
采用MTT法对分离得到的40个化合物进行了体外细胞毒活性考察。结果表明生物碱型甾体皂苷(1、3、4)，螺甾皂苷(11)和孕甾皂苷(36、38)等三种类型共6个化合物显示了不同程度的体外细胞毒活性。在综合分析测试结果的基础上，对体外细胞毒活性的构效关系进行了初步探讨。
本研究工作在化学和生物活性研究的基础上，证实了传统中药龙葵抗癌活性的作用物质基础为其中所含的甾体皂苷类化合物(包括生物碱型及非生物碱型)。化合物体外细胞毒活性和总皂苷体内活性表明中药龙葵有抗肿瘤作用。本文的实验结果将为今后对龙葵的研究与开发提供详实的理论和实验依据。
The total saponins extract from Solarium nigrum L. exhibited inhibitory activity on S180, and the anti-tumor effect demonstrated a positive effect relationship on the basis of amount.In our systematical study on the chemical constituents of Solarium nigrum L., 43 compounds were obtained from the ethanolic extract of the whole herb of this plant through various chromatographic techniques. Their structures were elucidated on the basis of physic-chemical property, spectroscopic analysis and chemical correlation (acidic hydrolysis, Mosher method). The 43 compounds from Solarium nigrum are solasonine (1),β_1-solasonine (2),β_2-solasonine (3), solamargine (4),β_2-solamargine (5), solanigroside P (6)*, solanigroside Q (7)*, (3β, 12β, 22α, 25R)-3, 12-dihydroxy-spirosol-5-en-27-oic acid (8), hypoglaucin H (9), dumoside (10), degalactotigonin (11), tigogenin 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (12), nigrumnin I (13), solanigroside C(14)*, solanigroside D (15)*, solanigroside E (16)*, solanigroside F (17)*, solanigroside G(18)*, solanigroside H (19)*, uttroside B (20), uttroside A (21), (22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furost-Δ~5-3β26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (22), (22α, 25β)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-Δ~5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-C)-β-D-galac-topyranoside (23), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furostan-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (24), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (25), solanigroside I (26)*, solanigroside J (27)*, solanigroside K (28)*, solanigroside L (29)*, solanigroside M (30)*, solanigroside N (31)*, solanigroside O (32)*, solanigroside R (33)*, solanigroside S (34)*, solanigroside T (35)*, 5α-pregn-16-en-3β-ol-20-one lycotetraoside (36), solanigroside A (37)*, solanigroside B (38)*, (5α, 20S)-3β,16β-dihydroxy pregn-22-carboxylic acid (22, 16)-lactone-3-(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (39), solanigroside U (40)*, solanigroside V (41)*, solanigroside W (42)*, solanigroside X (43)*. These compounds are comprised of 1 sapogenin and 42 saponins, including 8 steroidal alkaloids and 35 other steroidal saponins. Compounds 6, 7, 14-19, 26-35, 37, 38, 40-43 are new compounds. Compounds 9, 10, 22-25, 36, 39 were isolated for the first time from the solanum genus, and compounds 2, 3 were isolated from this plant for the first time. Compounds 28-35 and 42 are steroidal glycosides with new sapogenin.
Simultaneously, the fingerprint chromatomap of the total saponins extract from Solanum nigrum has been established using HPLC-ELSD. Above 85％of the peak areas in the chromatography have been identified by comparing with 11 compounds (4, 12, 13, 15, 17, 20, 25, 30, 31, 36) separated from the plant. The contents of two main steroidal saponins (11, 20) in the total glycosidic extract have been determined.
MTT method was used to test the cytotoxic activity of 40 compounds against four human tumor cell lines. Alkaloidal steroidal saponins (1, 3 and 4), spirostane saponin (11) and pregane saponins (36 and 38) showed cytotoxic activity. On the basis of results of cytotoxic activity assay, the structure-activity relationship for the compounds with similar aglycone structures from Solanum nigrum was discussed.
On the basis of chemical and bioactive studies in this academic dissertation, it was confirmed that the plant Solanum nigrum possess anti-tumor activities, and illustrated that the steroidal saponins from Solanum nigrum are responsible for its antitumor activity as a folk medicine.
通过综合运用D-101大孔吸附树脂、硅胶柱色谱、ODS柱色谱、Sephadex LH-20柱色谱以及制备型反相HPLC等多种色谱学分离手段，对龙葵乙醇提取物的总皂苷部分的化学成分进行了系统研究，从中分离得到43个化合物。利用理化性质、现代光谱学(IR、MS、~1H-NMR、~(13)C-NMR和2D-NMR)以及化学沟通(酸水解，Mosher法)等手段鉴定了它们的结构，分别为：solasonine (1),β_1-solasonine (2),β_2-solasonine (3), solamargine (4),β_2-solamargine (5),solanigroside P (6)~*, solanigroside Q (7)~*, (3β, 12β, 22α, 25R)-3,12-dihydroxy-spirosol-5-en-27-oic acid(8), hypoglaucin H(9), dumoside(10), degalactotigonin(11), tigogenin 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside(12), nigrumninⅠ(13), solanigroside C (14)~*,solanigroside D (15)~*, solanigroside E (16)~*, solanigroside F (17)~*, solanigroside G (18)~*,solanigroside H (19)~*, uttroside B (20), uttroside A (21), (22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furost-△~5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (22), (22α,25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-△~5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4).-O-β-D-galac-topyranoside (23), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furostan-3β,26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4).-O-β-D-galactopyranoside (24), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (25), solanigrosideⅠ(26)~*, solanigrosideJ (27)~*, solanigroside K (28)~*, solanigroside L (29)~*, solanigroside M (30)~*, solanigroside N(31)~*, solanigroside O (32)~*, solanigroside R (33)~*, solanigroside S (34)~*, solanigroside T (35)~*,5α-pregn-16-en-3β-ol-20-one lycotetraoside (36), solanigroside A (37)~*, solanigroside B (38)~*,(5α, 20S)-3β, 16β-dihydroxy pregn-22-carboxylic acid (22, 16)-lactone-3-(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylpyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (39), solanigroside U (40)~*, solanigroside V (41)~*, solanigroside W (42)~*,solanigroside X(43)~*。43个化合物中包括42个甾体皂苷类化合物和一个甾体皂苷元。其中，8个化合物分子中含有N原子，为生物碱型甾体皂苷类化合物，35个化合物分子中不含有N原子，为非生物碱型甾体皂苷类化合物。另外，有24个化合物(6、7、14-19、26-35、37、38、40-43)为新化合物，8个化合物(9、10、22-25、36、39)为首次从该属中分离得到，2个化合物(2、3)为首次从该种中分离得到。这些化合物中还包含了9种未见文献报道的全新苷元的糖苷(28-35，42)。
采用HPLC-ELSD方法建立了龙葵总皂苷标准提取物(活性部位)的指纹图谱，并用分离得到的11个化合物(30、25、20、31、17、36、15、4、12、13)为对照品，对标准提取物中峰面积占85％以上的峰进行了指认，测定了2个主要皂苷(11，20)的含量。
采用MTT法对分离得到的40个化合物进行了体外细胞毒活性考察。结果表明生物碱型甾体皂苷(1、3、4)，螺甾皂苷(11)和孕甾皂苷(36、38)等三种类型共6个化合物显示了不同程度的体外细胞毒活性。在综合分析测试结果的基础上，对体外细胞毒活性的构效关系进行了初步探讨。
本研究工作在化学和生物活性研究的基础上，证实了传统中药龙葵抗癌活性的作用物质基础为其中所含的甾体皂苷类化合物(包括生物碱型及非生物碱型)。化合物体外细胞毒活性和总皂苷体内活性表明中药龙葵有抗肿瘤作用。本文的实验结果将为今后对龙葵的研究与开发提供详实的理论和实验依据。
The total saponins extract from Solarium nigrum L. exhibited inhibitory activity on S180, and the anti-tumor effect demonstrated a positive effect relationship on the basis of amount.In our systematical study on the chemical constituents of Solarium nigrum L., 43 compounds were obtained from the ethanolic extract of the whole herb of this plant through various chromatographic techniques. Their structures were elucidated on the basis of physic-chemical property, spectroscopic analysis and chemical correlation (acidic hydrolysis, Mosher method). The 43 compounds from Solarium nigrum are solasonine (1),β_1-solasonine (2),β_2-solasonine (3), solamargine (4),β_2-solamargine (5), solanigroside P (6)*, solanigroside Q (7)*, (3β, 12β, 22α, 25R)-3, 12-dihydroxy-spirosol-5-en-27-oic acid (8), hypoglaucin H (9), dumoside (10), degalactotigonin (11), tigogenin 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (12), nigrumnin I (13), solanigroside C(14)*, solanigroside D (15)*, solanigroside E (16)*, solanigroside F (17)*, solanigroside G(18)*, solanigroside H (19)*, uttroside B (20), uttroside A (21), (22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furost-Δ~5-3β26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (22), (22α, 25β)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-Δ~5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-C)-β-D-galac-topyranoside (23), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furostan-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (24), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (25), solanigroside I (26)*, solanigroside J (27)*, solanigroside K (28)*, solanigroside L (29)*, solanigroside M (30)*, solanigroside N (31)*, solanigroside O (32)*, solanigroside R (33)*, solanigroside S (34)*, solanigroside T (35)*, 5α-pregn-16-en-3β-ol-20-one lycotetraoside (36), solanigroside A (37)*, solanigroside B (38)*, (5α, 20S)-3β,16β-dihydroxy pregn-22-carboxylic acid (22, 16)-lactone-3-(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (39), solanigroside U (40)*, solanigroside V (41)*, solanigroside W (42)*, solanigroside X (43)*. These compounds are comprised of 1 sapogenin and 42 saponins, including 8 steroidal alkaloids and 35 other steroidal saponins. Compounds 6, 7, 14-19, 26-35, 37, 38, 40-43 are new compounds. Compounds 9, 10, 22-25, 36, 39 were isolated for the first time from the solanum genus, and compounds 2, 3 were isolated from this plant for the first time. Compounds 28-35 and 42 are steroidal glycosides with new sapogenin.
Simultaneously, the fingerprint chromatomap of the total saponins extract from Solanum nigrum has been established using HPLC-ELSD. Above 85％of the peak areas in the chromatography have been identified by comparing with 11 compounds (4, 12, 13, 15, 17, 20, 25, 30, 31, 36) separated from the plant. The contents of two main steroidal saponins (11, 20) in the total glycosidic extract have been determined.
MTT method was used to test the cytotoxic activity of 40 compounds against four human tumor cell lines. Alkaloidal steroidal saponins (1, 3 and 4), spirostane saponin (11) and pregane saponins (36 and 38) showed cytotoxic activity. On the basis of results of cytotoxic activity assay, the structure-activity relationship for the compounds with similar aglycone structures from Solanum nigrum was discussed.
On the basis of chemical and bioactive studies in this academic dissertation, it was confirmed that the plant Solanum nigrum possess anti-tumor activities, and illustrated that the steroidal saponins from Solanum nigrum are responsible for its antitumor activity as a folk medicine.
引文
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19．李明英，卜乃锂，血尿灵合剂治疗肾小球性血尿40例，中医药学报，1996，5：17
20．李明英，邢建华，王庆兰，龙葵草合剂治疗功血临床及实验研究，中医药学报，1998，4：36-38
21．朱敏英，龙葵治疗崩漏症的临床观察，中国民族民间医药杂志，2004，68：163-164
22．李书奎，“三灵汤”治疗泌尿系感染，中华综合临床医学杂志，2003，5(5)：33
23. Larsen K., Medicinal and poisonous plants. Ⅰ. Solanum nigrum and Solanum dulcamara, Nord Med, 1961, 66: 1418-1419
24. Sadasivam S., Shanmugasundaram E. R., Studies on the flavokinase of Solanum nigrum L., Enzymologia, 1966, 31 (4): 203
25．潘伟光，刘宗潮，潘启超等，中药复方龙葵合剂在动物体内外的抗癌药效，癌症，1996，15(6)：438-440
26．陈汝盛，厉将斌，郭晓健等，猪苓龙葵水提物的抗肿瘤药效，中国中药杂志，2004，29(5)：481-482
27. Son Y. O., Kim J., Lim J. C. et al., Ripe fruit of Solanum nigrum L. inhibits cell growth and induces apoptosis in MCF-7 cells, Food Chem Toxicol, 2003, 41(10): 1421-1428
28. Ikeda, T., Tsumagari H., Honbu T., et al., Cytotoxic activity of steroidal glycosides from solanum plants, Biol. Pharm. Bull., 2003, 26(8): 1198-1201
29．赵晓琴，复方龙葵糖浆诱导小鼠H_(22)肝癌细胞凋亡作用机制研究，辽宁中医杂志，2005，32(9)：974-975
30．赖亚辉，刘良，董莉萍，龙葵浓缩果汁对S180荷瘤小鼠的抑瘤效应，中国预防医学杂志，2005，6(1)：28-29
31．王胜惠，从云峰，梁明等，龙葵90％醇提取物对荷瘤肝癌小鼠生存时间及肉瘤瘤重影响，黑龙江医学，2005，29(6)：421-422
32．季宇彬，王胜惠，高世勇等，龙葵碱对H_(22)荷瘤小鼠细胞膜流动性和膜蛋白水平的影响，中草药，2005， 36(2)：239-241
33．季宇彬，王胜惠，高世勇等，龙葵碱对H_(22)荷瘤小鼠肿瘤细胞膜唾液酸和封闭度的影响，中草药，2005，36(1)：79-80
34．季宇彬，王宏亮，高世勇，龙葵碱对荷瘤小鼠肿瘤细胞DNA和RNA的影响，中草药，2005，36(8)：1200-1202
35．季宇彬，王宏亮，高世勇，龙葵碱对肿瘤细胞膜ATP酶活性的影响，哈尔滨商业大学学报(自然科学版)，2005，21(2)：127-129
36．冯俊涛，石勇强，张兴，56种植物抑菌活性筛选试验，西北农林科技大学学报(自然科学版)，2001，29(2)：65-68
37．袁吕衡，周企贵，杨飞等，80种中药水煎液对淋球菌的抑制试验，中国医院药学杂志，1997，17(11)：508-509
38．何静，沈慧敏，张新虎，七种植物粗提物对常见植物病菌的抑菌作用研究，甘肃农业大学学报，2004，4：447-450
39. Perez R. M., Perez J. A., Garcia L. M., et al., Neuropharmacological activity of Solanum nigrum fruit, J Ethnopharmacol, 1998, 62(1): 43-48.
40. Ikeda, T., Ando J., Miyazono A. et al., Anti-herpes virus activity of Solanum steroidal glycosides, Biol. Pharm. Bull., 2000, 23(3): 363-364
41．董粉英，周绍国，龙葵引起维生素K依赖凝血因子缺乏3例报告，当代医师杂志，1998，3(11)：61
42．聂晶，赵燕丽，张冬等，龙葵遗传毒理的实验研究，中医药学报，1999，2：58-59
43. Raju K., Anbuganapathi G., Gokulakrishnan V., et al., Effect of dried fruits of Solanum nigrum LINN against CCl_4-induced hepatic damage in rats. Biol. Pharm. Bull., 2003, 26(11): 1618-1619
44. Sultana S., Perwaiz S., Iqbal M., et al., Crude extracts of hepatoprotective plants, Solanum nigrum and Cichorium intybus inhibit free radical-mediated DNA damage, J Ethnopharmacol, 1995, 45(3): 189-192.
45. Akhtar M. S., Munir M., Evaluation of the gastric antiulcerogenic effects of Solanum nigrum, Brassica oleracea and Ocimum basilicum in rats, J Ethnopharmacol, 1989, 27(1-2): 163-176.
46. Prashanth Kumar V. Shashidhara S., Kumar M. M., et al., Cytoprotective role of Solanum nigrum against gentamicin-induced kidney cell(Vero cells)damage in vitro, Fitoterapia, 2001, 72(5): 481-486
47. Moundipa P. F., Domngang F. M., Effect of the leafy vegetable Solanum nigrum on the activities of some liver drug-metabolizing enzymes after aflatoxin Bl treatment in female rats, The British journal of nutrition, 1991, 65(1): 81-91.
48．刘良，姜虹，吕俊华等，龙葵浓缩果汁和龙葵口服液抗二氧化硫致咳作用实验研究，吉林医学院学报，1996，16(4)：3-4
49．张成义，李霜，陈曦等，龙葵总生物碱抗喘作用机制的实验研究，中国医学理论与实践，2002，2002(4)：488-489
50．赖亚辉，马中春，刘良，龙葵浓缩果汁对小鼠细胞免疫调节作用实验研究中国预防医学杂志，2004，5(6)：478-480
51. Saijo R., Kotaro M., Toshihiro N., et al., Studies on the constituents of Solanum plants Ⅱ: On the constituents of the immature berries of Solanum nigrum L. Yakugaku Zasshi, 1982, 102(3): 300-305
52. Sharma S. C., Chand R.., Sati O. P., Uttronin B-a new spirostanoside from Solanum nigrum L., Pharmazie, 1982, 37(12): 870
53. Sharma S. C., Chand R., Sati O. R, et al., Oligofurostanosides from solanum nigrum, Phytochemistry, 1983, 22(5): 1241-1244
54. Doepke W., Duday S., Matos N., Alkaloids and sapogenins from Solanum nigrum, Z. Chem., 1987, 27(2): 64
55. Yoshida K., Yahara S., Saijo R., et al., Studies on the constituents of Solanum plants Part 8 Changes caused by included enzymes in the constituents of Solanum nigrum berries, Chem. Pharm. Bull., 1987, 35(4): 1645-1648
56 Doepke W., Duday S., Matos N., 23-O-acetyl-12β-hydroxysolasodine, a new alkaloid from Solanum nigrum L., Z. Chem., 1988, 28(5):185-186
57. Ikeda T., Tsumagari H., Nohara T., Steroidal oligoglycosides from Solanum nigrum, Chem. Pharm. Bull., 2000, 48(7): 1062-1064
58. Hu K., Kobayashi H., Dong A. J., et al., Antineoplastic agents Ⅲ: Steroidal glycosides from Solanum nigrum, Planta Medica, 1999, 65: 35-38.
59. Zhu X. H., Tsumagari H., Honbu T., et al., Peculiar steroidal saponins with opened E-ring from Solanum genera plants, Tetrahedron Letters, 2001, 42(45): 8043-8046
60. Ridout C. L., Price K. R., Coxon D. T., et al., Glycoalkaloids from Solanum nigrum L. a-solamargine and a-solasonine, Pharmazie, 1989, 44(10): 732-733
61. Benidze M. M., Steroidal glycosides of Solanum nigrum, Khim. Prir. Soedin., 1994, 5:683-684
62．王蔚，陆道培，龙葵总提取物对多发性骨髓瘤U266细胞株的作用，北京大学学报(医学版)，2005，37(3)：240-244
63. Maxwell A., Seepersaud M., Pingal R., Two 3α-aminospirosolane steroidal alkaloids from Solanum triste., J. Nat. Prod, 1996, 59:200-201
64. Mahato S. B., Sahu N. P., Ganguly A. N., et al., Steroidal alkaloids from solanum khasianum: application of ~(13)C NMR spectroscopy to their structural reducidation, Phytochemistry, 1980, 19:2017-2020
65. Chakravarty A. K., Das B., Ali E., et al., Studies on Indian Medicinal Plants Part 77: Structure and stereochemistry of Some New Steroidal alkloids from Solanum pseudocapsicum and Solanum giganteum by Nuclear Magnetic Resonance Spectroscopy, J. Chem. Perkin Trans. Ⅰ 1984:467-474
66. Sych F. J., Ripperger H., Schreiber K., Solanum alkaloids XCⅧ. Configuration of 22, 26-epimino-6, 23-epoxycholestanes at C-23, Tetrahedron, 1972, 28(6): 1645-1651
67. Ferreira F., Soule S., Vazquez A., et al., Steroid saponins from solanum laxum, Phytochemistry, 1996, 42(5): 1049-1416
68. Yamashita T., Matsumoto T., Yahara S., et al., Structrures of two new steroidal glycosides, soladulcosides A and B from Slanum dulcamara, Chem. Pharm. Bull., 1991, 39(6): 1626-1628
69. Mimaki Y., Kanmoto T., Sashida Y., et al., Steroidal saponins from the underground parts of chlorophytum comosum and their inhibitory activity on tumour promoter-induced phospholipids metabolism of hela cells, Phytochemistry, 1996, 41(5): 1405-1410
70. Raimundo F. B., Antonio G. G., Suarez L. E., New sources of steroid sapogenins Ⅷ. Sceptrumgenin and isoplexigenin A, B, C, and D from lsoplexis sceptrum, Tetrahedron, 1970, 26(13): 3233-44
71. Minpei K., Yoshihiro M., Fusako H., et al., Steroidal glycosides from the bulbs of Camassia leichtlinii and their cytotoxic activities, Chem. Pharm. Bull., 2001, 49(6): 726-731
72. Strigina L. Ⅰ., Isakov V. V., Carbon-~(13)NMR spectra of steroidal glycosides 1: Pennogenin glycosides, Khimiya Prirodnykh Soedinenii, 1982, 4:474-478
73. Keito K,, Kazumoto M., Nobuhiro M.,et al., Characterization of a minor compound, which accompanies the usual 22α(R)-O, 25β(S)-spirostanol glycoside, as a novel type of 22β(S)-O, 25α(S) analog, Chem. Pharm. Bull., 1984, 32:4229-4232
74．姚新生，彭军鹏，中药薤白新成分的鉴定及用途，发明专利申请公开说明书，1995
75. Tsuda M., Toriyabe Y., Endo T.,et al., Application of modified mosher's method for primary alcohols with a methyl group at C_2 position, Chem. Pharm. Bull., 2003, 51(4): 448-451
76. Ahmad V.U., Khaliq-uz-Zaman S. Shameel M. S., et al., Steroidal saponins from Asparagus dumosua, Phytochemistry, 1998, 50:481-484
77. Hamed A. Ⅰ., Oleszek W., Stochmal A.,et al., Steroidal saponins from the aerial parts of Tribulus pentandrus Forssk, Phytochemistry, 2004, 65:2935-2945
78. Toshinori N., Teruhiko Y., Sadao S., Lycopersiconolide, a steroid lactone from tomato roots, Phytochemistry, 1987, 26(7): 2113-2114
79. Jin J. M., Zhang Y. J., Yang C. R., Spirostanol and Furostanol Glycosides from the Fresh Tubers of Polianthes tuberose, J. Nat. Prod., 2004, 67:5-9
80. Yahara S., Nakamura T., Someya Y., et al., Steriodal glycosides, Indiosides A-E, from Splanum indicum, Phytochemistry, 1996, 43 (6): 1319-1323
81. Mossman T., Rapid colorimetric assay for cell growth and survival: application to proliferation and cytotoxicity assays, Journal of Immunological Methods, 1983, 65:55-63
82. Hara H., Okabe H., Mihashi K., Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates, Chem. Pharm. Bull., 1987, 35(2): 501-506.
83．郑德敏，于泓，赵焕敏，高效阴离子交换色谱——脉冲安培检测技术在糖类分析中的应用，哈尔滨师范大学自然科学学报，2003，9(3)：62-63
84. Eltayeb E. A., Al-Ansari A. S., Roddick J. G.., Changes in the steroidal alkaloid solasodine during development of Solanum nigrum and Solanum incanum, Phytochemistry, 1997, 46(3): 489-494
85. Ohmura E., Nakamura T., Tian R. H., et al., 26-aminocholestanol derivative, a novel key intermediate of steroidal alkaloidal, from solanum abutiloides, Tetrahedron Letters, 1995, 36(46): 8443-8444
2．《本草纲目》第十六卷草部五 龙葵455页
3. Nadkarni, M. K., Nadkarni, A. K, Indian Materia Medica, 1954, 1:1152
4. Chopra, R. N., Chopra, I. C., Handa, K. L., Indigenous drugs of India, 1958, 885 and 524
5．张锦燕，中药“龙葵”有助抗乳癌，新加坡联合早报2005-2-28第八版
6．曾元璋，10种有毒中草药抗肿瘤作用浅析，湖南中医药导报，1998，4(5)：8-9
7．赵晓琴，曾祥法，龙葵片对原发性肝癌治疗作用的临床研究，辽宁中医杂志，2002，29(11)：671-672
8．马安柱，赵红，张福林等，腹腔化疗同参赭培气汤治疗晚期肝癌36例，陕西中医，2004，25(1)：41-42
9．刘国良，李钟瑞，郭宏欣，中药体表外贴加化疗治疗肝癌61例临床观察，现代肿瘤医学，1997，5(4)：225-226
10．杜洪彬，宋慧，扶正消瘤汤合并MAF治疗晚期胃癌31例，黑龙江中医药，2004，3：13-14
11．谢远明，张长富，加味—贯煎治疗肺癌症106例，陕西中医，2002，23(4)：302-303
12．卜祥兆，赵保民，中西医结合治疗老年人中晚期肺癌临床观察，2004，18(4)：303-304
13．张维芳，杜俊宝，倪广林，龙葵栓外用为主治疗慢性细菌性前列腺炎150例——附野菊花栓治疗150例对照，浙江中医杂志，2000，8：365
14．徐振刚，龙葵栓组方思路及临床应用，张家口医学院学报，1999，16(4)：107
15．徐振刚，龙葵栓治疗慢性前列腺炎58例分析，张家口医学院学报，2000，17(1)：83-84
16．纪莎，胡雯玲，曾茂贵，龙葵降压汤治疗阴虚阳亢型高血压病57例，福建中医学院学报，2003，13(3)：7-8
17．刘良，姜虹，李洵等 龙葵止咳冲剂治疗气管炎疗效观察，吉林医学院学报，1996，16(4)：26-27
18．夏海岩，宣文虎，龟版龙葵汤治疗血尿30例，辽宁中医学院学报，1999，1(3)：188
19．李明英，卜乃锂，血尿灵合剂治疗肾小球性血尿40例，中医药学报，1996，5：17
20．李明英，邢建华，王庆兰，龙葵草合剂治疗功血临床及实验研究，中医药学报，1998，4：36-38
21．朱敏英，龙葵治疗崩漏症的临床观察，中国民族民间医药杂志，2004，68：163-164
22．李书奎，“三灵汤”治疗泌尿系感染，中华综合临床医学杂志，2003，5(5)：33
23. Larsen K., Medicinal and poisonous plants. Ⅰ. Solanum nigrum and Solanum dulcamara, Nord Med, 1961, 66: 1418-1419
24. Sadasivam S., Shanmugasundaram E. R., Studies on the flavokinase of Solanum nigrum L., Enzymologia, 1966, 31 (4): 203
25．潘伟光，刘宗潮，潘启超等，中药复方龙葵合剂在动物体内外的抗癌药效，癌症，1996，15(6)：438-440
26．陈汝盛，厉将斌，郭晓健等，猪苓龙葵水提物的抗肿瘤药效，中国中药杂志，2004，29(5)：481-482
27. Son Y. O., Kim J., Lim J. C. et al., Ripe fruit of Solanum nigrum L. inhibits cell growth and induces apoptosis in MCF-7 cells, Food Chem Toxicol, 2003, 41(10): 1421-1428
28. Ikeda, T., Tsumagari H., Honbu T., et al., Cytotoxic activity of steroidal glycosides from solanum plants, Biol. Pharm. Bull., 2003, 26(8): 1198-1201
29．赵晓琴，复方龙葵糖浆诱导小鼠H_(22)肝癌细胞凋亡作用机制研究，辽宁中医杂志，2005，32(9)：974-975
30．赖亚辉，刘良，董莉萍，龙葵浓缩果汁对S180荷瘤小鼠的抑瘤效应，中国预防医学杂志，2005，6(1)：28-29
31．王胜惠，从云峰，梁明等，龙葵90％醇提取物对荷瘤肝癌小鼠生存时间及肉瘤瘤重影响，黑龙江医学，2005，29(6)：421-422
32．季宇彬，王胜惠，高世勇等，龙葵碱对H_(22)荷瘤小鼠细胞膜流动性和膜蛋白水平的影响，中草药，2005， 36(2)：239-241
33．季宇彬，王胜惠，高世勇等，龙葵碱对H_(22)荷瘤小鼠肿瘤细胞膜唾液酸和封闭度的影响，中草药，2005，36(1)：79-80
34．季宇彬，王宏亮，高世勇，龙葵碱对荷瘤小鼠肿瘤细胞DNA和RNA的影响，中草药，2005，36(8)：1200-1202
35．季宇彬，王宏亮，高世勇，龙葵碱对肿瘤细胞膜ATP酶活性的影响，哈尔滨商业大学学报(自然科学版)，2005，21(2)：127-129
36．冯俊涛，石勇强，张兴，56种植物抑菌活性筛选试验，西北农林科技大学学报(自然科学版)，2001，29(2)：65-68
37．袁吕衡，周企贵，杨飞等，80种中药水煎液对淋球菌的抑制试验，中国医院药学杂志，1997，17(11)：508-509
38．何静，沈慧敏，张新虎，七种植物粗提物对常见植物病菌的抑菌作用研究，甘肃农业大学学报，2004，4：447-450
39. Perez R. M., Perez J. A., Garcia L. M., et al., Neuropharmacological activity of Solanum nigrum fruit, J Ethnopharmacol, 1998, 62(1): 43-48.
40. Ikeda, T., Ando J., Miyazono A. et al., Anti-herpes virus activity of Solanum steroidal glycosides, Biol. Pharm. Bull., 2000, 23(3): 363-364
41．董粉英，周绍国，龙葵引起维生素K依赖凝血因子缺乏3例报告，当代医师杂志，1998，3(11)：61
42．聂晶，赵燕丽，张冬等，龙葵遗传毒理的实验研究，中医药学报，1999，2：58-59
43. Raju K., Anbuganapathi G., Gokulakrishnan V., et al., Effect of dried fruits of Solanum nigrum LINN against CCl_4-induced hepatic damage in rats. Biol. Pharm. Bull., 2003, 26(11): 1618-1619
44. Sultana S., Perwaiz S., Iqbal M., et al., Crude extracts of hepatoprotective plants, Solanum nigrum and Cichorium intybus inhibit free radical-mediated DNA damage, J Ethnopharmacol, 1995, 45(3): 189-192.
45. Akhtar M. S., Munir M., Evaluation of the gastric antiulcerogenic effects of Solanum nigrum, Brassica oleracea and Ocimum basilicum in rats, J Ethnopharmacol, 1989, 27(1-2): 163-176.
46. Prashanth Kumar V. Shashidhara S., Kumar M. M., et al., Cytoprotective role of Solanum nigrum against gentamicin-induced kidney cell(Vero cells)damage in vitro, Fitoterapia, 2001, 72(5): 481-486
47. Moundipa P. F., Domngang F. M., Effect of the leafy vegetable Solanum nigrum on the activities of some liver drug-metabolizing enzymes after aflatoxin Bl treatment in female rats, The British journal of nutrition, 1991, 65(1): 81-91.
48．刘良，姜虹，吕俊华等，龙葵浓缩果汁和龙葵口服液抗二氧化硫致咳作用实验研究，吉林医学院学报，1996，16(4)：3-4
49．张成义，李霜，陈曦等，龙葵总生物碱抗喘作用机制的实验研究，中国医学理论与实践，2002，2002(4)：488-489
50．赖亚辉，马中春，刘良，龙葵浓缩果汁对小鼠细胞免疫调节作用实验研究中国预防医学杂志，2004，5(6)：478-480
51. Saijo R., Kotaro M., Toshihiro N., et al., Studies on the constituents of Solanum plants Ⅱ: On the constituents of the immature berries of Solanum nigrum L. Yakugaku Zasshi, 1982, 102(3): 300-305
52. Sharma S. C., Chand R.., Sati O. P., Uttronin B-a new spirostanoside from Solanum nigrum L., Pharmazie, 1982, 37(12): 870
53. Sharma S. C., Chand R., Sati O. R, et al., Oligofurostanosides from solanum nigrum, Phytochemistry, 1983, 22(5): 1241-1244
54. Doepke W., Duday S., Matos N., Alkaloids and sapogenins from Solanum nigrum, Z. Chem., 1987, 27(2): 64
55. Yoshida K., Yahara S., Saijo R., et al., Studies on the constituents of Solanum plants Part 8 Changes caused by included enzymes in the constituents of Solanum nigrum berries, Chem. Pharm. Bull., 1987, 35(4): 1645-1648
56 Doepke W., Duday S., Matos N., 23-O-acetyl-12β-hydroxysolasodine, a new alkaloid from Solanum nigrum L., Z. Chem., 1988, 28(5):185-186
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