Isolation and Identification of Chemical Constituents from Cinnamomi Ramulus

Ling-li ZHU; Zhi-fu AI; Li XU; Yong-liang JIN; Chun-ling LIU; Feng LIU; Hua LIU

doi:10.13422/j.cnki.syfjx.20190712

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Isolation and Identification of Chemical Constituents from Cinnamomi Ramulus

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

- Isolation and Identification of Chemical Constituents from Cinnamomi Ramulus
- Chinese Journal of Experimental Traditional Medical Formulae Vol. 25, Issue 14, Pages: 173-178(2019)
- 作者机构：
  
  1.江西中医药大学　药学院，南昌　 330004；
  2.江西中医药大学　研究生院，南昌　 330004；
  3.樟树市人民医院，江西　樟树　 331200；
  4.江西中医药大学　附属医院，南昌　 330006
- 作者简介：
- 基金信息：
- DOI：10.13422/j.cnki.syfjx.20190712
  CLC： R284.2; R289; R22; R2-031
- Received：21 October 2018，
  
  Published Online：19 December 2018，
  
  Published：20 July 2019
- 稿件说明：
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Ling-li ZHU, Zhi-fu AI, Li XU, et al. Isolation and Identification of Chemical Constituents from Cinnamomi Ramulus[J]. Chinese journal of experimental traditional medical formulae, 2019, 25(14): 173-178.
DOI：

Ling-li ZHU, Zhi-fu AI, Li XU, et al. Isolation and Identification of Chemical Constituents from Cinnamomi Ramulus[J]. Chinese journal of experimental traditional medical formulae, 2019, 25(14): 173-178. DOI： 10.13422/j.cnki.syfjx.20190712.

摘要

目的：

明确桂枝的活性组分，对75%乙醇提浸膏进行系统化学成分分离与纯化，以期找到抑制necroptosis的目标小分子化合物。

方法：

取干燥桂枝20 kg，粉碎后用75%乙醇冷浸提取，提取4次，7 d 1次，减压回收溶剂得到总浸膏。将所得总浸膏，运用D101大孔吸附树脂柱色谱进行分离，依次用水，30%乙醇，50%乙醇，70%乙醇，90%乙醇洗脱，减压回收溶剂得水部分，30%乙醇部分，50%乙醇部分，70%乙醇部分，90%乙醇部分。对30%乙醇部分，50%乙醇部分联合采用常压硅胶柱色谱，LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱，高压制备色谱，重结晶等方法进行分离纯化，并根据单体化合物理化性质与波谱学数据(

H-NMR，

C-NMR，MS)等进行结构鉴定。

结果和结论：

从桂枝中分离得到13个化合物，分别鉴定为(＋)-丁香脂素(1)，(＋)-南烛木树脂酚(2)，山橘脂酸(3)，裂异落叶松脂醇(4)，ovafolinin B(5)，原儿茶醛(6)，原儿茶酸(7)，丁香醛(8)，香草酸(9)，原儿茶酸乙酯(10)，丁香酸(11)，没食子酸乙酯(12)，2-(3′，4′-二羟苯基)-1，3-胡椒环-5-醛(13)。其中1～5，10～13为首次从该植物中分离得到。

Abstract

Objective:

The research group found in the early stage that the 75%alcohol extract of the Cinnamomi Ramulus had a significant physiological activity in inhibiting necroptosis by screening out the self-built sample library of 100 kinds of traditional Chinese medicines in Jiangxi. To identify the active components and find the target compounds

the 75%alcohol extracts of Cinnamomi Ramulus were isolated and studied systemically in chemistry.

Method:

The 20 kg dry Cinnamomi Ramulus was crushed into coarse powder

and extracted with 75%alcohol for four times

one time every 7 d. Then total extracts were obtained after solvent was recycled under decompression. The extract was separated by D101 macroporous resin column chromatography and eluted by water

30%ethanol

50%ethanol

70%ethanol

90%ethanol

so as to get the corresponding fraction finally. The compounds in the 30%ethanol and 50%ethanol fraction were isolated and purified by chromatography on silica gel

Sephadex LH-20 column and high pressure preparative chromatography

and their structures were determined according to physicochemical properties and spectral analysis.

Result and Conclusion:

Thirteen compounds were isolated and identified as (+ )-syringaresinol (1)

(+ )-lyoniresinol (2)

spicatolignan B (3)

(-)-secoisolariciresinol (4)

ovafolinin B (5)

protocatechualdehyde (6)

protocatechuic acid (7)

syringaldehyde (8)

vanillic acid (9)

ethyl protocatechuate (10)

syringic acid (11)

ethyl gallate (12)

2-(3′

4′-dihydroxyphenyl)-1

3-pepper ring-5-aldehyde (13). Compounds 1-5

10-13 were isolated from this plant for the first time.

关键词

Keywords

references

LIANG M T , YANG C H , LI S T , et al . Antibacterial and antioxidant properties of Ramulus Cinnamomi using supercritical CO2 extraction [J]. Eur Food Res Technol , 2008 , 227 ( 5 ): 1387 - 1396 .

黄敬群，王四旺，罗晓星，等．桂皮醛对裸鼠人胃癌细胞移植瘤生长及凋亡的影响 [J]．解放军药学学报， 2006 ， 22 ( 5 )： 343 - 346 ．

Verspohl E J , Bauer K , Neddermann E . Antidiabetic effect of Cinnamomum cassia and Cinnamomum zeylanicum in vivo and in vitro [J]. Phytother Res , 2005 , 19 ( 3 ): 203 - 206 .

蒋时红，李澜，吴耀松，等．桂枝茯苓丸抑制人乳腺癌细胞MCF-7增殖机制 [J]．中国实验方剂学杂志， 2018 ， 24 ( 15 )： 132 - 136 ．

王瑞敏，侯懿，豆艳艳．桂枝茯苓丸和参麦散加减对宫颈癌患者术后放化疗的近期疗效观察 [J]．中国实验方剂学杂志， 2014 ， 20 ( 6 )： 187 - 191 ．

WU C , CAO S , HONG T , et al . Taxifolin inhibits rat and human 11β-hydroxysteroid dehydrogenase 2 [J]. Fitoterapia , 2017 , 121 : 112 - 117 .

Manigandan K , Manimaran D , Jayaraj R L , et al . Taxifolin curbs NF-κB-mediated Wnt/β-catenin signaling via up-regulating Nrf2 pathway in experimental colon carcinogenesis [J]. Biochimie , 2015 , 119 : 103 - 112 .

KANG Y H , Shin H M . Vasorelaxant effect of Cinnamomi ramulus ethanol extract via rho-kinase signaling pathway [J]. Am J Chinese Med , 2011 , 39 ( 5 ): 867 - 878 .

CHEN Y H , LIN Y N , CHEN W C , et al . Treatment of stress urinary incontinence by cinnamaldehyde, the major constituent of the chinese medicinal herb Cinnamomi ramulus [J]. Evid Based Complement Alternat Med , 2014 , 42 ( 4 ): 817 - 831 .

Cho S , Cho M , Kim J , et al . Syringaresinol protects against hypoxia/reoxygenation-induced cardiomyocytes injury and death by destabilization of HIF-1α in a FOXO3-dependent mechanism [J]. Oncotarget , 2015 , 6 ( 1 ): 43 - 55 .

吴晨露，谢南南，周伸奥，等．程序性细胞坏死的分子机制及其在炎症中的作用 [J]．中国细胞生物学学报， 2016 ， 38 ( 1 )： 7 - 16 ．

Takahashi N , Duprez L , Grootjans S , et al . Necrostatin-1 analogues: critical issues on the specificity, activity and in vivo use in experimental disease models [J]. Cell Death Dis , 2012 , 3 ( 11 ): e437 .

KAN S , CHEN G , HAN C , et al . Chemical constituents from the roots of Xanthium sibiricum [J]. Nat Prod Res , 2011 , 25 ( 13 ): 1243 - 1249 .

颜世达，姚慧丽，张英华，等．柳叶绣线菊化学成分研究 [J]．中草药， 2016 ， 47 ( 16 )： 2806 - 2811 ．

OUYANG M A , Wein Y S , SU R K , et al . Rhusemialins A-C, new cyclolignan esters from the roots of Rhus javanica var. roxburghiana [J]. Chem Pharm Bull , 2007 , 55 ( 5 ): 804 - 807 .

ZHENG J , CHEN G T , GAO H Y , et al . Two new lignans from Mentha spicata L [J]. J Asian Nat Prod Res , 2007 , 9 ( 5 ): 431 - 435 .

王芳菲，李燕，董海玲，等．铁皮石斛中一个新化合物 [J]．中国药学杂志， 2010 ， 45 ( 12 )： 898 - 902 ．

Kashima K , Sano K , Yun Y S , et al . Ovafolinins A-E, five new lignans from Lyonia ovalifolia [J]. Chem Pharm Bull (Tokyo) , 2010 , 58 ( 2 ): 191 - 194 .

ZHAO A H , ZHAO Q S , TAO L R , et al . Chemical constituents from Clerodendranthus spicatus [J]. Acta Botanica Yunnanica , 2004 , 26 ( 5 ): 563 - 568 .

WANG W , YANG C R , ZHANG Y J . Phenolic constituents from the fruits of Amomum tsao-ko(Zingiberaceae) [J]. Acta Botanica Yunnanica , 2009 , 31 ( 3 ): 284 - 288 .

文屏，韩慧英，王乃利，等．毛杭子梢化学成分的研究 [J]．中草药， 2008 ， 39 ( 8 )： 1143 - 1145 ．

ZHANG T T , ZHOU J S , LIU Y , et al . Chemical constituents of the aerial part of Bupleurum longicaule [J]. Chin J Nat Med , 2008 , 6 ( 6 ): 430 - 434 .

Phadungkit M , Luanratana O . Anti-salmonella activity of constituents of Ardisia elliptica Thunb [J]. Nat Prod Res , 2006 , 20 ( 7 ): 693 - 696 .

尚小雅，李帅，王映红，等．红绒毛羊蹄甲的化学成分研究 [J]．中国中药杂志， 2006 ， 31 ( 23 )： 1953 - 1955 ．

Motoyuki T , Yasuyuki O . A new antioxidative 1, 3-benzodioxole from Melissa officinalis [J]. Planta Med , 1998 , 64 ( 6 ): 555 - 558 .

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