摘要
目的 研究珍珠菜全草乙酸乙酯提取物中的五环三萜-3-O-对香豆酸酯类化学成分。方法 利用硅胶柱色谱法、Sephadex LH-20凝胶柱色谱法、中压柱色谱及半制备高效液相色谱等方法 分离纯化;通过核磁共振谱、质谱、红外光谱等光谱数据鉴定化合物结构。结果 分离得到6种五环三萜-3-O-对香豆酸酯类化合物,分别被鉴定为(Z)-马斯里酸-3-O-对香豆酸酯(Ⅰ),(E)-马斯里酸-3-O-对香豆酸酯(Ⅱ),(Z)-2α-羟基乌苏酸-3-O-对香豆酸酯(Ⅲ),(E)-2α-羟基乌苏酸-3-O-对香豆酸酯(Ⅳ),(Z)-萎陵菜酸-3-O-对香豆酸酯(Ⅴ),(E)-萎陵菜酸-3-O-对香豆酸酯(Ⅵ)。结论 化合物Ⅰ~Ⅵ均为首次在珍珠菜属植物中发现。
Abstract
OBJECTIVE To isolate and identify the 3-O-p-coumaroyloxyl pentacyclic triterpenoids from acetoacetate extract of Lysimachia clethroides Duby, which showed significant cancer chemopreventive activities. METHODS The 3-O-p-coumaroyloxyl pentacyclic triterpenoids were isolated by using silica gel column chromatography, Sephadex LH-20 chromatography MPLC, and Semi-HPLC. Their structures were elucidated with spectroscopic analysis(NMR, MS and IR ). RESULTS Six 3-O-p-coumaroyloxyl pentacyclic triterpenoids were isolated and identified as 3-O-cis-p-coumaroyl maslinic acid(Ⅰ), 3-O-trans-p-coumaroyl maslinic acid(Ⅱ), 3-O-cis-p-coumaroyl-2α-hydroxyursolic acid(Ⅲ), 3-O-trans-p-coumaroyl- 2α-hydroxyursolic acid(Ⅳ), 3-O-cis-p-coumaroyl tormentic acid(Ⅴ) and 3-O-trans-p- coumaroyl tormentic acid(Ⅵ). CONCLUSION All these compounds were obtained from the Lysimachia Genus for the first time.
关键词
珍珠菜 /
五环三萜-3-O-对香豆酸酯 /
分离 /
鉴定
{{custom_keyword}} /
Key words
Lysimachia clethroides Duby /
3-O-p-coumaroyloxyl pentacyclic triterpenoids /
isolation /
identification
{{custom_keyword}} /
许琼明 唐丽华 李夏 郝丽莉 李笑然 杨世林.
珍珠菜中五环三萜-3-O-对香豆酸酯类化学成分的分离鉴定[J]. 中国药学杂志, 2010, 45(11): 825-827
XU Qiong-ming;TNG Li-hu;LI Xi;HO Li-li;LI Xio-rn;YNG Shi-lin.
Isolation and Identification of 3-O-p-Coumaroyloxyl Pentacyclic Triterpenoids from Lysimachia clethroides Duby[J]. Chinese Pharmaceutical Journal, 2010, 45(11): 825-827
{{custom_sec.title}}
{{custom_sec.title}}
{{custom_sec.content}}
参考文献
[1] GUO B L, XIAO P G, YANG S L. Studies on the medicinal species of the Lysimachia Genus in China [J]. World Notes Plant Med(国外医药:植物药分册), 1995, 10(4): 159-162.
[2] The Group of Treatment and Prevention of Tumor of Hankou Hospital of Air-force. Empirical study on the antitumor activities of the total flavonoids isolated from Lysimachia clethroides Duby [J]. J New Med(新医学), 1977, 8(3): 112-113.
[3] The Group of Treatment and Prevention of Tumor of Hankou Hospital of Air-force. Therapeutic action of total flavonoids isolated from Lysimachia clethroides Duby on L615 leukemia [J]. J New Med(新医学), 1981, 12(6): 293-294.
[4] XU X Y, TANG L H, LIANG Z Q, et al. The primary studies on the anti-tumor effect of the extracts of Lysmachia clethroides [J]. Chin Wild Plant Resour(中国野生植物资源), 2003, 22(2): 31-34.
[5] CHANG H T, KONG W L, TU P F. Chemical and pharmacological advances of study on Lysimachia [J]. Chin J Chin Mater Med(中国中药杂志), 2004, 29(4): 295-298.
[6] GU J Q, PARK E J, LUYENGI L, et al. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity [J]. Phytochemistry, 2001, 58(1): 121-127.
[7] HE X J, LIU R H. Triterpenoids isolated from apple peels have potent antiproliferative activity and may be partially responsible for apple′s anticancer activity [J]. J Agric Food Chem, 2007, 55(11): 4366-4370.
[8] HABERLEIN H, TSCHIERSCH K P. Triterpenoids and flavonoids from Leptospermum scoparium [J]. Phytochemistry, 1994, 35(3): 765-768.
[9] LEE C K. Ursane triterpenoids from leaves of Melaleuca leucadendron [J]. Phytochemistry, 1998, 49(4):1119-1121.
[10] NUMATA A, YANG P, TAKAHASHI C, et al. Cytotoxic triterpenes from a chinese medicine, Goreishi [J]. Chem Pharm Bull, 1989, 37(3): 648-651.
{{custom_fnGroup.title_cn}}
脚注
{{custom_fn.content}}