皂角刺中3个香豆素类化合物及其细胞毒活性研究
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摘要
目的研究皂角刺Gleditsiae Spina(皂荚干燥棘刺)的化学成分。方法利用硅胶、Sephadex LH-20等柱色谱法反复进行分离纯化,通过谱学分析和理化性质鉴定表征化合物的结构。细胞毒活性采用四甲偶氮唑盐(MTT)比色法,测定化合物对肝癌(Hep G2)、肺癌(A-549)和食管癌(EC109)细胞株的细胞增殖抑制率。结果从皂角刺90%乙醇提取物的醋酸乙酯部位分离得到3个香豆素类化合物,分别鉴定为滨蒿内酯(1)、异东莨菪内酯(2)和6-氨基-7-甲氧基香豆素(3)。结论化合物3为新的香豆素类化合物,命名为皂角香豆素A。化合物1、2为首次从该植物中分离得到。细胞毒活性研究显示化合物2对肺癌A549细胞有较强的增殖抑制活性,其IC50值为34.47μg/m L。
Objective To investigate the chemical constituents from Gleditsiae Spina(the thorns of Gleditsia sinensis). Methods The compounds were isolated and purified by silica gel, Sephadex LH-20 column chromatographic techniques, and their chemical structures were confirmed on the basis of spectroscopic analysis by the physicochemical properties. Cytotoxic activity using the MTT colorimetry method was performed to measure the inhibitory effect of the compounds on cell proliferation of Hep G2, A-549, and EC109. Results Three coumarins were obtained from the ethyl acetate soluble fraction of the 90% ethanolic extract and their structures were identified as scoparone(1), isoscopoletin(2), and 6-amino-7-methoxycoumarin(3). Conclusion Compound 3 is a novel coumarin named gledisinmarin A. Compounds 1 and 2 are isolated from this plant for the first time. Compound 2 displays the stronger cytotoxicity against A549 cell with an IC50 value of 34.47 μg/m L, while cisplatin with an IC50 value of 11.50 μg/m L as a positive control.
Objective To investigate the chemical constituents from Gleditsiae Spina(the thorns of Gleditsia sinensis). Methods The compounds were isolated and purified by silica gel, Sephadex LH-20 column chromatographic techniques, and their chemical structures were confirmed on the basis of spectroscopic analysis by the physicochemical properties. Cytotoxic activity using the MTT colorimetry method was performed to measure the inhibitory effect of the compounds on cell proliferation of Hep G2, A-549, and EC109. Results Three coumarins were obtained from the ethyl acetate soluble fraction of the 90% ethanolic extract and their structures were identified as scoparone(1), isoscopoletin(2), and 6-amino-7-methoxycoumarin(3). Conclusion Compound 3 is a novel coumarin named gledisinmarin A. Compounds 1 and 2 are isolated from this plant for the first time. Compound 2 displays the stronger cytotoxicity against A549 cell with an IC50 value of 34.47 μg/m L, while cisplatin with an IC50 value of 11.50 μg/m L as a positive control.
引文
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[3]陈国平.中国抗癌中草药[M].上海:上海科学技术出版社,1984.
[4]徐哲,赵晓頔,王漪檬.皂角刺抗肿瘤活性成分的分离鉴定与活性测定[J].沈阳药科大学学报,2008,25(2):108-110.
[5]Zhang Z Z,Kazuo K,Jia Z H,et al.Triterpenoidal saponins from Gleditsia sinensis[J].Phytochemistry,1999,52(4):715-722.
[6]Li W H,Zhang X M,Tian R R,et al.A new anti-HIV lupine acid from Gleditsia sinensis Lam.[J].J Asian Nat Prod Res,2007,9(6):551-555.
[7]Lim J C,Park J H,Budesinsky M,et al.Antimutagenic constituents from the thorns of Gleditsia sinensis[J].Chem Pharm Bull,2005,53(5):561-564.
[8]李万华,李琴,王小刚,等.皂角刺中黄酮类化学成分的分离鉴定[J].西北大学学报:自然科学版,2005,35(6):763-765.
[9]Zhou L G,Li D,Gou J,et al.Antibacterial phenolic compounds from the spines of Gleditsia sinensis Lam.[J].Nat Prod Res,2007,21(4):283-291.
[10]Xian Y X,Zhou H L,Wang X,et al.Anti-liver cancer constituents from the thorns of Gleditsia sinensis[J].Phytochem Lett,2015,13:343-347.
[11]李万华,傅建熙,范代娣.皂角刺化学成分的研究皂甙成分的研究[J].西北大学学报:自然科学版,2000,30(2):137-138.
[12]Zhou L G,Li D,Jian W B,et al.Two ellagic acid glycosides from Gleditsia sinensis Lam.with antifungal activity on Magnaporthe grisea[J].Nat Prod Res,2007,21(4):303-309.
[13]Wang J H,Tang J,Li D,et al.Chemical constituents and bioactivity of Gleditsia plants[J].Chin Wild Plant Res,2008,27(6):1-3.
[14]曹冉冉,高嘉屿,尹卫平,等.皂角刺中二氢黄酮醇类化合物及其细胞毒活性研究[J].中草药,2016,47(5):707-711.
[15]刘应杰,陈竹,叶小利,等.紫薯中6,7-二甲氧基香豆素和5-羟甲基糠醛的分离鉴定[J].西南师范大学学报:自然科学版,2013,38(1):85-89.
[16]吴文标,盛德贤,吕世安,等.马铃薯块茎中的6-羟基-7-甲氧基香豆素的分离和鉴定[J].中国马铃薯,1999,13(2):79-80.
[17]梁晓天,刘春雪,姬政,等.莨菪亭及异莨菪亭的合成[J].中国医药工业杂志,1983,14(4):6-7.
[18]龚运怀.天然有机化合物的13C核磁共振化学位移[M].昆明:云南科技出版社,1986.
[19]Mulwad V V,Dalvi M B,Mahaddalkar B S.Synthesis of some antimicrobial pyranocarbazomycin[J].Indian J Chem,Sec B:Org Chem Including Med Chem,2002,41B(7):1477-1479.
[20]Hu Q F,Zhou B,Ye Y Q,et al.Cytotoxic deoxybenzoins and diphenylethylenes from Arundina graminifolia[J].J Nat Prod,2013,76(10):1854-1859.