Isolation and Identification of Chemical Constituents of Phenolic Acid from Cimicifuga dahurica

Ru-lan QIN; Chong-ning LYU; Yang YU; Jin-cai LU

doi:10.13422/j.cnki.syfjx.20191917

您当前的位置：

首页 >

文章列表页 >

Isolation and Identification of Chemical Constituents of Phenolic Acid from Cimicifuga dahurica

Resource and Quality Evaluation | 更新时间：2021-02-09

- Isolation and Identification of Chemical Constituents of Phenolic Acid from Cimicifuga dahurica
- Chinese Journal of Experimental Traditional Medical Formulae Vol. 25, Issue 21, Pages: 112-117(2019)
- 作者机构：
  
  1.通化师范学院，吉林　通化　 134002；
  2.沈阳药科大学，沈阳　 110016
- 作者简介：
- 基金信息：
- DOI：10.13422/j.cnki.syfjx.20191917
  CLC： R284.2; R289; R22; R2-031
- Received：26 February 2019，
  
  Published Online：17 June 2019，
  
  Published：05 November 2019
- 稿件说明：
移动端阅览
Ru-lan QIN, Chong-ning LYU, Yang YU, et al. Isolation and Identification of Chemical Constituents of Phenolic Acid from Cimicifuga dahurica[J]. Chinese journal of experimental traditional medical formulae, 2019, 25(21): 112-117.
DOI：

Ru-lan QIN, Chong-ning LYU, Yang YU, et al. Isolation and Identification of Chemical Constituents of Phenolic Acid from Cimicifuga dahurica[J]. Chinese journal of experimental traditional medical formulae, 2019, 25(21): 112-117. DOI： 10.13422/j.cnki.syfjx.20191917.

摘要

目的：

毛茛科(Ranunculaceae)兴安升麻(

Cimicifuga dahurica

)具有多种药用功效，目前对其皂苷类成分研究比较深入，但有关酚酸类成分的系统研究报道甚少，为明确兴安升麻中的酚酸类成分，对兴安升麻药材进行分离，并对所得化合物进行结构鉴定，以期为兴安升麻药材资源的进一步开发利用及质量控制提供依据。

方法：

兴安升麻根茎16 kg，采用70%乙醇加热回流提取3次，减压回收溶剂成浸膏。浸膏加适量的水混匀后，依次用石油醚、乙酸乙酯、正丁醇进行萃取。乙酸乙酯和水层萃取物经大孔树脂，硅胶，十八烷基硅烷键合硅胶(ODS)，LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱，Pre-HPLC，重结晶等分离手段进行分离纯化，并通过理化性质，核磁共振(NMR)技术等对所得化合物进行结构鉴定。

结果：

从兴安升麻的乙酸乙酯和水层部位分离得到15个化合物，分别为升麻酸G(1)，2-咖啡酰番石榴酸(2)，升麻酸A(3)，升麻酸B(4)，咖啡酸3-

-葡萄糖苷(5)，升麻酸E(6)，升麻酸F(7)，反式-阿魏酸-4-

-葡萄糖苷(8)，carboxymethyl isoferulate(9)，3，4-二甲氧基肉桂酸(10)，阿魏酸乙酯(11)，咖啡酸葡萄糖酯苷(12)，shomaside A (13)，异阿魏酸(14)，咖啡酸(15)。

结论：

化合物1～7，9～10，13为首次从兴安升麻中分离得到。

Abstract

Objective:

Cimicifuga dahurica

(Ranunculaceae) has many bioactivities. Although there have been intensive studies for saponin constituents at present

only a few studies have focused on for chemical constituents of phenolic acid. To define the phenolic acid constituents

dahurica

was separated

and the structures of the compounds were identified

in the expectation of providing a basis for its further development

utilization and quality control.

Method:

A total of 16 kg rhizome of

dahurica

was extracted with 70%ethanol for three times by heating reflux. These 3 extracts were decompressed and concentrated

and then dissolved in water. Then the solvent was successively extracted with petroleum ether

ethyl acetate(EtOAc) and

-butanol(BuOH). The components of EtOAc and water extract were isolated and purified by macroporous

silica gel

ODS

Sephadex LH-20 column chromatography

preparative HPLC and recrystallization

and the structures were identified by nuclear magnetic resonance(NMR) and physicochemical analysis etc.

Result:

Fifteen compounds were isolated from the ethyl acetate and water fractions

and identified as cimicifugic G (1)

2-caffeoyl piscidic acid (2)

cimicifugic A (3)

cimicifugic B (4)

caffeic acid 3-

-glucopyranoside (5)

cimicifugic E (6)

cimicifugic F (7)

trans

-ferulic acid 4-

-glucopyranoside (8)

carboxymethyl isoferulate (9)

4-dimethoxycinnamic acid (10)

ethyl ferulate (11)

caffeic ester glucoside (12)

shomaside A (13)

isoferulic acid (14)

caffeic acid (15).

Conclusion:

Compounds 1-7

9-10

13 were isolated from the plant for the first time.

关键词

Keywords

references

国家药典委员会．中华人民共和国药典．一部 [M]．北京：中国医药科技出版社， 2015 ： 73 - 74 ．

苏占辉，张滋明，王书君，等．兴安升麻地上部分的提取分离工艺考察 [J]．中国实验方剂学杂志， 2013 ， 19 ( 5 )： 10 - 13 ．

祝婧，钟凌云，龚千锋，等．升麻不同炮制品对脾气虚动物胃肠功能的影响 [J]．中国实验方剂学杂志， 2015 ， 21 ( 21 )： 1 - 4 ．

高璟春，彭勇，杨梦苏，等．毛茛科升麻族植物药用亲缘学初探 [J]．植物分类学报， 2008 ， 46 ( 4 )： 516 - 536 ．

NIAN Y , ZHANG X M , LI Y , et al . Cycloartane triterpenoids from the aerial parts of Cimicifuga foetida Linnaeus [J]. Phytochemistry , 2011 , 72 ( 11/12 ): 1473 - 1481 .

张庆文，叶文才，赵守训，等．兴安升麻的化学成分研究 [J]．中草药， 2002 ， 33 ( 8 )： 683 - 685 ．

裴秋燕，斯建勇，沈连刚，等．兴安升麻根茎的化学成分研究 [J]．中草药， 2012 ， 43 ( 6 )： 1075 - 1078 ．

QIN R L , ZHAO Y , ZHAO Y D , et al . Polyphenolic compounds with antioxidant potential and neuro-protective effect from Cimicifuga dahurica (Turcz.) Maxim [J]. Fitoterapia , 2016 , 115 : 52 - 56 .

QIN R L , LV C N , ZHAO Y , et al . Assessment of phenolics contents and antioxidant properties in Cimicifuga dahurica (Turcz.) Maxim during drying process [J]. Ind Crop Prod , 2017 , 107 : 288 - 296 .

Nuntanakorn P , JIANG B , Einbond L S , et al . Polyphenolic constituents of Actaea racemosa [J]. J Nat Prod , 2006 , 69 ( 3 ): 314 - 318 .

Takahira M , Kusano A , Shibano M , et al . Piscidic acid and fukiic acid esters from Cimicifuga simplex [J]. Phytochemistry , 1998 , 49 ( 7 ): 2115 - 2119 .

Takahira M , Kusano A , Shibano M , et al . Three new fukiic acid esters, cimicifugic acids A, B and C, from Cimicifuga simplex Wormsk . [J]. Chem Inform , 2010 , 29 ( 28 ): 362 - 365 .

卢丽丽，肖敏，郭玉川．咖啡酸糖苷衍生物及其制备方法：中国， CN103304606A [P]． 2013-09-18 ．

Iwanaga A , Kusano G , Warashina T , et al . Hyaluronidase inhibitors from “Cimicifugae Rhizoma” (a mixture of the Rhizomes of Cimicifuga dahurica and C. heracleifolia) [J]. J Nat Prod , 2010 , 73 ( 4 ): 573 - 578 .

王新峦，王乃利，黄文秀，等．骨碎补中的苯丙素类成分及其对UMR 106 细胞增殖作用的影响 [J]．沈阳药科大学学报， 2008 ， 25 ( 1 )： 24 - 29 ．

Yim S H , Kim H J , Park S H , et al . Cytotoxic caffeic acid derivatives from the rhizomes of Cimicifuga heracleifolia [J]. Arch Pharm Res , 2012 , 35 ( 9 ): 1559 - 1565 .

费永和，陈重，李笑然，等．向日葵种子的化学成分研究 [J]．中草药， 2014 ， 45 ( 5 )： 631 - 634 ．

龚盛昭，李忠军，廖国俊，等．阳离子交换树脂催化合成阿魏酸乙酯 [J]．精细化工， 2010 ， 27 ( 4 )： 362 - 364 ．

李从军，陈迪华，肖培根．中药升麻的化学成分(V) [J]．中草药， 1995 ， 26 ( 6 )： 288 - 289 ．

付红伟，郑春辉，曹家庆，等．落花生枝叶化学成分的研究(Ⅱ) [J]．中国药物化学杂志， 2006 ， 16 ( 5 )： 309 - 310 ．

赵晓宏，陈迪华，斯建勇，等．中药升麻酚酸类化学成分研究 [J]．药学学报， 2002 ， 37 ( 7 )： 535 - 538 ．

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Analysis and Identification of Chemical Constituents in Hypoglycemic Effective Fractions of Longan Folium Based on UPLC-Q-Orbitrap HRMS

Study on Chemical Constituents of Ethyl Acetate Fraction of

Chemical Composition of Ethyl Acetate Fraction of Notoginseng Radix et Rhizoma Medicinal Fungal

Chemical Constituents of Ethyl Acetate Fraction of Ginseng Radix et Rhizoma Medicinal Fungal Substance

Related Author

Jie LIANG

Jin-yu WEI

Dong-fang HUANG

Jing LIN

Xiao-si CHEN

Xian-fu LIU

Guang-qiang HUANG

LIAO Shang-gao

Related Institution

Guangxi Zhuang Yao Medicine Engineering Technology Research Center， Guangxi University of Chinese Medicine

Faculty of Chinese Medicine Science，Guangxi University of Chinese Medicine

AI问答

Postal code：100700
Tel：010-84076882 Email：syfjx_2010@188.com
Technical support is provided by Beijing Founder electronics co., LTD 京ICP备11006657号-10 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰