土丹参根中的三萜类和酚酸类成分
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摘要
目的对民间丹参代用品土丹参Salvia kiaometiensis乙醇提取物进行化学成分研究。方法采用溶剂提取法、硅胶柱、凝胶柱色谱等色谱技术进行提取分离,核磁共振、质谱等波谱技术进行结构鉴定。结果分离得到15个化合物,主要为三萜和酚酸类化合物,分别鉴定为(2α,3α)-二羟基-3,24-异亚丙基二氧基熊果-12(13),20(29)-二烯-28-酸(1)、2α,3α-二羟基熊果-12-烯-28-酸(2)、euscaphicacid(3)、2α-羟基熊果酸(4)、山香双烯酸(5)、serrulatinE(6)、齐墩果酸(7)、3,3′-二乙氧基迷迭香酸(8)、clinopodic acid B(9)、迷迭香酸(10)、(Z,E)-2-(3,4-二羟基苯基)乙烯基酯(11)、咖啡酸(12)、咖啡酸乙酯(13)、2′,4′-二羟基查耳酮(14)、4-羟基苯甲酸二十五酯(15)。结论土丹参含有正品丹参相似的酚酸类化合物。化合物1为新熊果烷型三萜,命名为土丹参酸,所有化合物均为首次从该植物中得到。
Objective To study the chemical constituents of the roots of Salvia kiaometiensis, which was used as S. miltiorrhiza.Methods Compounds were isolated and identified by a variety of chromatographic techniques and spectroscopic methods. Results Fifteen compounds were obtained and identified as(2α,3α)-dihydroxy-3,24-(isopropylidenedioxy) urs-12(13),20(29)-diene-28-oic acid(1), 2α,3α-dihydroxyurs-12-ene-28-olic acid(2), euscaphic acid(3), 2α-hydroxyursolic acid(4), hyptadienic acid(5), serrulatin E(6), oleanolic acid(7), 3,3′-diethoxy rosmarinic acid(8), clinopodic acid B(9), rosmarinic acid(10),(Z,E)-2-(3,4-dihydroxyphenyl)ethenyl ester(11), caffeic acid(12), caffeic acid ethyl ester(13), 2′,4′-dihydroxychalcone(14), and 4-hydroxy-benzoic acid pentacosyl ester(15). Conclusion S. kiaometiensis has similar phenolic acids with S. miltiorrhiza. Compound 1 is a new compound named kiaometic acid. All compounds are isolated from this plant for the first time.
Objective To study the chemical constituents of the roots of Salvia kiaometiensis, which was used as S. miltiorrhiza.Methods Compounds were isolated and identified by a variety of chromatographic techniques and spectroscopic methods. Results Fifteen compounds were obtained and identified as(2α,3α)-dihydroxy-3,24-(isopropylidenedioxy) urs-12(13),20(29)-diene-28-oic acid(1), 2α,3α-dihydroxyurs-12-ene-28-olic acid(2), euscaphic acid(3), 2α-hydroxyursolic acid(4), hyptadienic acid(5), serrulatin E(6), oleanolic acid(7), 3,3′-diethoxy rosmarinic acid(8), clinopodic acid B(9), rosmarinic acid(10),(Z,E)-2-(3,4-dihydroxyphenyl)ethenyl ester(11), caffeic acid(12), caffeic acid ethyl ester(13), 2′,4′-dihydroxychalcone(14), and 4-hydroxy-benzoic acid pentacosyl ester(15). Conclusion S. kiaometiensis has similar phenolic acids with S. miltiorrhiza. Compound 1 is a new compound named kiaometic acid. All compounds are isolated from this plant for the first time.
引文
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[2]国家中医药管理局《中华本草》编委会.中华本草(第7卷)[M].上海:上海科学技术出版社,1999.
[3]夏光惠,李元平,毕德文,等.荞麦地鼠尾草根中的二萜类成分[J].有机化学,2017,37(10):2772-2775.
[4]Mahato S B,Kundu A P.13C NMR spectra of pentacyclic triterpenoids-a compilation and some salient features[J].Phytochemistry,1994,37(6):1517-1575.
[5]马凤爱,吴德玲,许凤清,等.中华猕猴桃果实化学成分的研究[J].中成药,2016,38(3):591-593.
[6]鲁学照,罗厚蔚.三叶鼠尾草的化学研究[J].中国中药杂志,1996,21(7):424-425.
[7]Song Y L,Wang Y H,Lu Q,et al.Triterpenoids from the edible leaves of Photinia serrulata[J].Helv Chim Acta,2008,91(4):665-672,
[8]赵谦,廖矛川,郭济贤.凌霄花的化学成分与抗生育活性[J].天然产物研究与开发,2002,14(3):1-6.
[9]郭群群,杜桂彩,李荣贵,等.紫苏抗菌活性成分的研究[J].高等学校化学学报,2006,27(7):1292-1294.
[10]Toshihiro M,Kenroh S,Kumiko S,et al.Matrix metalloproteinase-2 inhibitors from Clinopodium chinense var.parviflorum[J].J Nat Prod,2009,72(8):1379-84.
[11]吴志军,欧阳明安,杨崇仁.苣叶丹参的多酚类化合物[J].云南植物研究,1999,21(3):393-398.
[12]Nakanishi T,Nishi M,Inada A,et al.Two new potent inhibitors of xanthine oxidase from leaves of Perilla frutescens Britton var.acuta Kudo[J].Chem Pharm Bull,1990,38(6):1772-1774.
[13]朱仝飞,陈日荣,孙庆文,等.西藏胡黄连化学成分研究[J].中草药,2017,48(2):263-265.
[14]张创峰,沈硕,宋联强,等.连花清瘟胶囊的化学成分研究(II)[J].中草药,2018,49(14):3222-3225.
[15]张玉莲,梅任强,刘熙,等.东北岩高兰化学成分研究[J].中草药,2014,45(16):2293-2298.