白花蛇舌草化学成分及其抗肿瘤活性
|
摘要
目的研究白花蛇舌草Hedyotis diffusa Willd.的化学成分及其抗肿瘤活性。方法白花蛇舌草90%乙醇提取物采用大孔树脂、硅胶柱、TLC、HPLC制备柱进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。CCK-8法测定体外抑制鼻咽癌细胞株CNE1、结肠癌细胞HT-29的活性。结果从中分离得到9个化合物,分别鉴定为香草酸(1)、对香豆酸(2)、2-羟基-3-甲基蒽醌(3)、6α-O-反式-对香豆酰京尼平苷(4)、槲皮素-3-O-[2″-O-(E-6-O-阿魏酰基)-β-D-葡萄糖]-β-D-葡萄糖苷(5)、3,4-二羟基苯甲酸(6)、2-羟基-7-甲基-3-甲氧基蒽醌(7)、10-去氢京尼平苷(8)、1-甲醛-4-羟基蒽醌(9)。1、3、7、9体外能抑制CNE1、HT-29肿瘤细胞生长。结论化合物9为新的天然产物,1、3、7、9为白花蛇舌草的抗肿瘤成分。
AIM To study the chemical constituents from Hedyotis diffusa Willd. and their antitumor activities. METHODS The 90% ethanol extract from H. diffusa was isolated and purified by macroporous resin,silica column,TLC and preparative HPLC colum,then the structures of obtained compounds were identified by physicochemical properties and spectral data. The antitumor activities to CNE1 and HT-29 in vitro were determined by CCK-8 method. RESULTS Nine compounds were isolated and identified as 4-hydroxy-3-methox-ybenzoic acid( 1), p-coumaric acid( 2),2-hydroxy-3-methylanthraquinone( 3),6α-O-p-trans-coumaroyl-geniposide( 4), quercetin-O-[2″-O-( E-6-O-feruloyl)-β-D-glucopyranosyl]-β-D-glucopyranoside( 5),3,4-dihydroxybenzoic acid( 6),2-hydroxy-7-methyl-3-methoxyanthraquinone( 7),10-dehydro-geniposide( 8),1-formaldehyde-4-hydroxyl anthraquinone( 9). Compounds 1,3,7,9 could inhibit proliferation of CNE1、HT-29 in vitro. CONCLUSION Compound 9 is a new natural product,and compounds 1,3,7,9 are antitumor active constituents of H. diffusa.
AIM To study the chemical constituents from Hedyotis diffusa Willd. and their antitumor activities. METHODS The 90% ethanol extract from H. diffusa was isolated and purified by macroporous resin,silica column,TLC and preparative HPLC colum,then the structures of obtained compounds were identified by physicochemical properties and spectral data. The antitumor activities to CNE1 and HT-29 in vitro were determined by CCK-8 method. RESULTS Nine compounds were isolated and identified as 4-hydroxy-3-methox-ybenzoic acid( 1), p-coumaric acid( 2),2-hydroxy-3-methylanthraquinone( 3),6α-O-p-trans-coumaroyl-geniposide( 4), quercetin-O-[2″-O-( E-6-O-feruloyl)-β-D-glucopyranosyl]-β-D-glucopyranoside( 5),3,4-dihydroxybenzoic acid( 6),2-hydroxy-7-methyl-3-methoxyanthraquinone( 7),10-dehydro-geniposide( 8),1-formaldehyde-4-hydroxyl anthraquinone( 9). Compounds 1,3,7,9 could inhibit proliferation of CNE1、HT-29 in vitro. CONCLUSION Compound 9 is a new natural product,and compounds 1,3,7,9 are antitumor active constituents of H. diffusa.
引文
[1]陈德溯,方肇勤.中药治疗原发性肝癌中晚期的药味频率分析[J].辽宁中医杂志,2002,29(4):187-189.
[2]钟立敏,周宏霞,刘丹.白花蛇舌草的药理和临床应用进展[J].中医药信息,2001,18(4):14-15.
[3]于春艳,李薇,刘玉和,等.白花蛇舌草提取物体外抗肿瘤作用及机制研究[J].北华大学学报(自然科学版),2004,5(5):412-416.
[4]Kim S H,Ahn B Z,Ryu S Y.Antitumour effects of ursolic acid isolated from Oldenlandia diffusa[J].Phytother Res,2015,12(8):553-556.
[5]Wu P K,Chi Shing Tai W,Liang Z T,et al.Oleanolic acid isolated from Oldenlandia diffusa exhibits a unique growth inhibitory effect against ras-transformed fibroblasts[J].Life Sci,2009,85(3-4):113-121.
[6]王晓梅,张倩,热娜·卡斯木,等.锁阳全草化学成分的研究[J].中草药,2011,42(3):458-460.
[7]Biro T,Brodie C,Modarres S,et al.Specific vanilloid responses in C6 rat glioma cells[J].Brain Res Mol Brain Res,1998,56(1-2):89-98.
[8]Pakhtusova N,Zaostrovskaya L,Lindstr9m P,et al.Cell-specific Ca(2+)responses in glucose-stimulated single and aggregated beta-cells[J].Cell Calcium,2003,34(2):121-129.
[9]殷婕,邬云霞,吴启南,等.淡竹叶的化学成分研究[J].西北药学杂志,2010,25(6):413-414.
[10]梁少瑜,陈飞龙,汤庆发,等.白花蛇舌草化学成分研究[J].中药新药与临床药理,2012,23(6):655-657.
[11]Abdel-Wahab M H,El-Mahdy M A,Abd-Ellah M F,et al.Influence of p-coumaric acid on doxorubicin-induced oxidative stress in rat’s heart[J].Pharmacol Res,2003,48(5):461-465.
[12]周应军,吴孔松,曾光尧,等.白花蛇舌草化学成分的研究[J].中国中药杂志,2007,32(7):590-593.
[13]汪辰卉.白花蛇舌草中Src蛋白激酶抑制成分的分离鉴定[D].杭州:浙江大学,2007.
[14]Wu H,Tao X,Chen Q,et al.Iridoids from Hedyotis diffusa[J].J Nat Prod,2004,54(1):254-256.
[15]任风芝,刘刚叁,张丽,等.白花蛇舌草黄酮类化学成分研究[J].中国药学杂志,2005,40(7):502-504.
[16]张丽娟,廖尚高,詹哲浩,等.头花蓼酚酸类化学成分研究[J].时珍国医国药,2010,21(8):1946-1947.
[17]郎素梅,朱丹妮,余伯阳,等.中药鬼箭羽降糖有效部位的药效学和化学研究[J].中国药科大学学报,2003,34(2):128-131.
[18]康兴东,李铣,毛羽,等.白花蛇舌草的化学成分[J].沈阳药科大学学报,2007,24(8):479-481.
[19]张永勇,罗佳波.白花蛇舌草化学成分研究[J].中药材,2008,28(4):522-524.
[20]曾永长,梁少瑜,罗佳波,等.白花蛇舌草水提部位体内外抗肿瘤实验研究[J].中药新药与临床药理,2011,22(5):521-524.
[2]钟立敏,周宏霞,刘丹.白花蛇舌草的药理和临床应用进展[J].中医药信息,2001,18(4):14-15.
[3]于春艳,李薇,刘玉和,等.白花蛇舌草提取物体外抗肿瘤作用及机制研究[J].北华大学学报(自然科学版),2004,5(5):412-416.
[4]Kim S H,Ahn B Z,Ryu S Y.Antitumour effects of ursolic acid isolated from Oldenlandia diffusa[J].Phytother Res,2015,12(8):553-556.
[5]Wu P K,Chi Shing Tai W,Liang Z T,et al.Oleanolic acid isolated from Oldenlandia diffusa exhibits a unique growth inhibitory effect against ras-transformed fibroblasts[J].Life Sci,2009,85(3-4):113-121.
[6]王晓梅,张倩,热娜·卡斯木,等.锁阳全草化学成分的研究[J].中草药,2011,42(3):458-460.
[7]Biro T,Brodie C,Modarres S,et al.Specific vanilloid responses in C6 rat glioma cells[J].Brain Res Mol Brain Res,1998,56(1-2):89-98.
[8]Pakhtusova N,Zaostrovskaya L,Lindstr9m P,et al.Cell-specific Ca(2+)responses in glucose-stimulated single and aggregated beta-cells[J].Cell Calcium,2003,34(2):121-129.
[9]殷婕,邬云霞,吴启南,等.淡竹叶的化学成分研究[J].西北药学杂志,2010,25(6):413-414.
[10]梁少瑜,陈飞龙,汤庆发,等.白花蛇舌草化学成分研究[J].中药新药与临床药理,2012,23(6):655-657.
[11]Abdel-Wahab M H,El-Mahdy M A,Abd-Ellah M F,et al.Influence of p-coumaric acid on doxorubicin-induced oxidative stress in rat’s heart[J].Pharmacol Res,2003,48(5):461-465.
[12]周应军,吴孔松,曾光尧,等.白花蛇舌草化学成分的研究[J].中国中药杂志,2007,32(7):590-593.
[13]汪辰卉.白花蛇舌草中Src蛋白激酶抑制成分的分离鉴定[D].杭州:浙江大学,2007.
[14]Wu H,Tao X,Chen Q,et al.Iridoids from Hedyotis diffusa[J].J Nat Prod,2004,54(1):254-256.
[15]任风芝,刘刚叁,张丽,等.白花蛇舌草黄酮类化学成分研究[J].中国药学杂志,2005,40(7):502-504.
[16]张丽娟,廖尚高,詹哲浩,等.头花蓼酚酸类化学成分研究[J].时珍国医国药,2010,21(8):1946-1947.
[17]郎素梅,朱丹妮,余伯阳,等.中药鬼箭羽降糖有效部位的药效学和化学研究[J].中国药科大学学报,2003,34(2):128-131.
[18]康兴东,李铣,毛羽,等.白花蛇舌草的化学成分[J].沈阳药科大学学报,2007,24(8):479-481.
[19]张永勇,罗佳波.白花蛇舌草化学成分研究[J].中药材,2008,28(4):522-524.
[20]曾永长,梁少瑜,罗佳波,等.白花蛇舌草水提部位体内外抗肿瘤实验研究[J].中药新药与临床药理,2011,22(5):521-524.