Structure of Gardenia Blue Pigment and Its Inhibitory Activity on Monoamine Oxidase B

Qi-hang JIANG; Guang-da YAO; Chao-qie XU; Ming-ming XU; Cheng-bin YANG; Wei-wei TAO; Ming ZHAO

doi:10.13422/j.cnki.syfjx.20211749

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Structure of Gardenia Blue Pigment and Its Inhibitory Activity on Monoamine Oxidase B

更新时间：2021-12-31

- Structure of Gardenia Blue Pigment and Its Inhibitory Activity on Monoamine Oxidase B
- Chinese Journal of Experimental Traditional Medical Formulae Vol. 28, Issue 3, Pages: 123-130(2022)
- 作者机构：
  
  1.南京中医药大学江苏省中药资源产业化过程协同创新中心，国家中医药管理局中药资源循环利用重点研究室，中药资源产业化与方剂创新药物国家地方联合工程研究中心，南京 210023
  2.宁夏医科大学药学院，银川 750004
- 作者简介：
- 基金信息：
- DOI：10.13422/j.cnki.syfjx.20211749
  CLC： R22;R28;O581;O657
- Received：26 March 2021，
  
  Published Online：26 May 2021，
  
  Published：05 February 2022
- 稿件说明：
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蒋启航,姚广大,许朝且等.栀子蓝色素的结构及其对单胺氧化酶B的抑制活性考察[J].中国实验方剂学杂志,2022,28(03):123-130.

JIANG Qi-hang,YAO Guang-da,XU Chao-qie,et al.Structure of Gardenia Blue Pigment and Its Inhibitory Activity on Monoamine Oxidase B[J].Chinese Journal of Experimental Traditional Medical Formulae,2022,28(03):123-130.
蒋启航,姚广大,许朝且等.栀子蓝色素的结构及其对单胺氧化酶B的抑制活性考察[J].中国实验方剂学杂志,2022,28(03):123-130. DOI： 10.13422/j.cnki.syfjx.20211749.

JIANG Qi-hang,YAO Guang-da,XU Chao-qie,et al.Structure of Gardenia Blue Pigment and Its Inhibitory Activity on Monoamine Oxidase B[J].Chinese Journal of Experimental Traditional Medical Formulae,2022,28(03):123-130. DOI： 10.13422/j.cnki.syfjx.20211749.

摘要

目的

研究栀子蓝色素的化学结构及其对单胺氧化酶B（MAO-B）的抑制活性，为栀子环烯醚萜类资源性化学成分的合理利用及价值提升寻求潜在可行途径。

方法

采用纤维素酶催化水解栀子环烯醚萜苷类化合物得到其苷元，经与氨基酸反应，D101型大孔树脂柱色谱及制备液相色谱分离纯化，获得栀子蓝色素单体，综合运用核磁共振波谱和质谱技术鉴定其结构；以苯甲胺为MAO-B反应底物，与栀子蓝色素单体体外孵育，采用高效液相色谱法检测苯甲胺的代谢产物苯甲醛生成量，以甲醇（A）-50 mmol·L

-1

磷酸钾缓冲液（B，pH 3.2）（2∶3）为流动相，检测波长245 nm，以评价栀子蓝色素化合物对MAO-B的抑制效果。

结果

合成并鉴定了8种栀子蓝色素（栀子蓝色素A~H）。在MAO-B抑制试验中，与栀子苷比较，栀子蓝色素D，E的抑制活性明显增强（

0.05）；与6

-羟基京尼平苷比较，栀子蓝色素G，H的抑制活性明显增强（

0.05，

0.01），这4种栀子蓝色素均表现出比原型化合物更好的MAO-B抑制活性。

结论

栀子蓝色素为一分子氨基酸与一分子环烯醚萜形成的简单化合物，部分栀子蓝色素具有比原型化合物更好的MAO-B抑制活性，不同底物生产出的栀子蓝色素存在活性差异，可基于试验优选制备高价值栀子蓝色素，扩展栀子蓝色素的应用范围，丰富栀子环烯醚萜类成分的综合利用途径。

Abstract

Objective

To study the chemical structure of gardenia blue pigment and its inhibitory activity against monoamine oxidase B （MAO-B）， in order to seek a potential feasible way for rational utilization and value enhancement of iridoids in Gardeniae Fructus.

Method

Iridoid glycosides in Gardeniae Fructus were hydrolyzed by cellulase to obtain their aglycones and reacted with amino acids. Then， the products were purified by column chromatography packed with D101 macroporous resin and preparative liquid chromatography to obtain gardenia blue pigments， and the gardenia blue pigments were identified by nuclear magnetic resonance （NMR） and mass spectrometry （MS）. Benzylamine was used as the reaction substrate of MAO-B and

in vitro

incubated with gardenia blue pigment monomers， high performance liquid chromatography （HPLC） was employed to determine the production of benzaldehyde for evaluating the inhibitory effect of gardenia blue pigments on MAO-B， the mobile phase was methanol （A） -50 mmol·L

-1

potassium phosphate buffer （B， pH 3.2）（2∶3）， and the detection wavelength was 245 nm.

Result

Eight compounds of gardenia blue pigment A-H were synthesized and identified. In MAO-B inhibition test， compared with geniposide， the inhibitory activity of gardenia blue pigment D and E was significantly enhanced （

0.05）. Compared with the 6

-hydroxygeniposide， the inhibitory activity of gardenia blue pigment G and H was significantly enhanced （

0.05，

0.01）. All the four gardenia blue pigments showed better MAO-B inhibitory activity than the prototype compounds.

Conclusion

Gardenia blue pigment is a simple compound formed by one molecule of amino acid and one molecule of iridoid. Some gardenia blue pigments have better MAO-B inhibitory activity than the prototype compounds. The activity of gardenia blue pigment produced by different substrates is different， and the high-value gardenia blue pigment can be prepared based on experimental optimization， which can expand the application range of gardenia blue pigment and enrich the comprehensive utilization of iridoids from Gardeniae Fructus.

关键词

Keywords

references

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