Chemical composition analysis and multi-component content determination of grape seed extract based on ultra performance liquid chromatography tandem mass spectrometry

  • LI Jinfa ,
  • DIAO Juanjuan ,
  • CHEN Zhanghao ,
  • GAO Shuang ,
  • CHANG Junmin
Expand
  • 1(School of Pharmacy, Xinjiang Medical University, Urumqi 830011, China)
    2(Central Laboratory, Xinjiang Medical University, Urumqi 830011,China)
    3(Xinjiang Key Laboratory of Natural Drug Active Components and Drug Release Technology, Urumqi 830011, China)

Received date: 2024-05-15

  Revised date: 2024-07-15

  Online published: 2024-11-01

Abstract

In this study, liquid chromatography-mass spectrometry (LC-MS) combined with the UNIFI screening platform was used to quickly and qualitatively analyze the chemical components in grape seed extract, and establish a method for the determination of effective components in grape seed extract.Firstly, the mass spectrum data of grape seed extract were collected by ultra-performance liquid chromatography-quadrupole-time-of-flight high-resolution mass spectrometry (UPLC-Q-TOF-MS/MS).According to the matching results of the database built by UNIFI software, combined with the retention time of control substance, characteristic fragment ions and related literature, 20 chemical constituents were identified from grape seed extract, including 7 polyphenols, 1 triterpene, 1 flavonol, 1 unsaturated fatty acid, 1 polyhydroxylamine, 3 phenolic acids, and 6 amino acids.In addition, the four active components (catechin, epicatechin, proanthocyanidin B2 and proanthocyanidin C1) in grape seed extract were determined simultaneously by ultra performance liquid chromatography-triple quadrupole mass spectrometry (UPLC-QqQ-MS/MS).The linear relationship was good in their respective ranges (r≥0.998), and the average sample recovery was 96.7%-102.6%.This study provides a rapid, simple, and accurate method for qualitative and quantitative analysis of chemical components in grape seed extract, providing an important theoretical reference for its quality evaluation and basic research of pharmacodynamic substances.

Cite this article

LI Jinfa , DIAO Juanjuan , CHEN Zhanghao , GAO Shuang , CHANG Junmin . Chemical composition analysis and multi-component content determination of grape seed extract based on ultra performance liquid chromatography tandem mass spectrometry[J]. Food and Fermentation Industries, 2024 , 50(20) : 303 -312 . DOI: 10.13995/j.cnki.11-1802/ts.039887

References

[1] 王霄倩, 王恒振, 刘丽娜, 等. 葡萄皮渣的营养价值及综合利用[J]. 中国农学通报, 2017, 33(27):147-151.
WANG X Q, WANG H Z, LIU L N, et al. Nutritional value and comprehensive utilization of grape pomace[J]. Chinese Agricultural Science Bulletin, 2017, 33(27):147-151.
[2] 王丽娟, 杨宋琪, 郭兴霞, 等. 响应面法优化超声波辅助提取葡萄籽中油脂及其脂肪酸成分分析[J]. 粮食与油脂, 2018, 31(3):49-52.
WANG L J, YANG S Q, GUO X X, et al. Optimization of ultrasonic-assisted extraction of grape seed oil by response surface methodology and its fatty acid composition analysis[J]. Cereals & Oils, 2018, 31(3):49-52.
[3] 林童, 卢贞希, 刘改霞, 等. 葡萄籽油的脂肪酸组成、抗氧化活性及其在可食性口红中的应用[J]. 中国油脂, 2021, 46(3):118-121.
LIN T, LU Z X, LIU G X, et al. Fatty acid composition and antioxidant activity of grape seed oil and its application in edible lipstick[J]. China Oils and Fats, 2021, 46(3):118-121.
[4] 张王孝. 葡萄籽抗氧化活性研究进展[J]. 科技视界, 2014(21):63.
ZHANG W X. Research progress on antioxidant activity of grape seeds[J]. Science & Technology Vision, 2014(21):63.
[5] JEKABSONE A, SILE I, COCHIS A, et al. Investigation of antibacterial and antiinflammatory activities of proanthocyanidins from Pelargonium sidoides DC root extract[J]. Nutrients, 2019, 11(11):2829.
[6] ZENG Y X, WANG S, WEI L, et al. Proanthocyanidins: Components, pharmacokinetics and biomedical properties[J]. The American Journal of Chinese Medicine, 2020, 48(4):813-869.
[7] ZHOU Q, HAN X, LI R B, et al. Anti-atherosclerosis of oligomeric proanthocyanidins from Rhodiola rosea on rat model via hypolipemic, antioxidant, anti-inflammatory activities together with regulation of endothelial function[J]. Phytomedicine, 2018, 51:171-180.
[8] QAED E, ALMOILIQY M, AL-HAMYARI B, et al. Procyanidins: A promising anti-diabetic agent with potential benefits on glucose metabolism and diabetes complications[J]. Wound Repair and Regeneration, 2023, 31(5):688-699.
[9] RIPPIN, SHARMA A K, BENIWAL V. Biosynthesis and medicinal applications of proanthocyanidins: A recent update[J]. Biocatalysis and Agricultural Biotechnology, 2022, 45:102500.
[10] 郭磊,杨静玉,王芳,等.葡萄籽提取物化学成分及药理活性的研究进展[J].沈阳药科大学学报,2008,25(S1):32-34.
GUO L, YANG J Y, WANG F, et al. Research progress on chemical constituents and pharmacological activities of grape seed extract[J]. Journal of Shenyang Pharmaceutical University,2008,25(S1):32-34.
[11] 蔡定吉, 李志强, 彭万钱, 等. 基于UPLC-Q-TOF-MS技术的紫丁香化学成分及入血成分研究[J]. 中药材, 2023, 46(4):892-902.
CAI D J, LI Z Q, PENG W Q, et al. Study on the chemical constituents and components into blood of Syringa oblata based on UPLC-Q-TOF-MS[J]. Journal of Chinese Medicinal Materials, 2023, 46(4):892-902.
[12] 周胡怿,赵希娟,焦必宁.基于UPLC-QqQ-MS/MS同时检测佛手中香豆素类化合物含量[J/OL].食品与发酵工业,1-12.https://doi.org/10.13995/j.cnki.11-1802/ts.035236.
ZHOU H Z, ZHAO X J, JIAO B N. Simultaneous determination of coumarins in Radix formosanis based on UPLC-QqQ-MS/MS[J/OL]. Food and Fermentation Industries,1-12. https://doi.org/10.13995/j.cnki.11-1802/ts.035236.
[13] ZHANG F X, LI M, QIAO L R, et al. Rapid characterization of Ziziphi Spinosae Semen by UPLC/Qtof MS with novel informatics platform and its application in evaluation of two seeds from Ziziphus species[J]. Journal of Pharmaceutical and Biomedical Analysis, 2016, 122:59-80.
[14] 黄彪, 刘文静, 方灵, 等. 基于UPLC-MS/MS同时分析福建乌龙茶和白茶中的儿茶素类物质[J]. 食品工业科技, 2020, 41(10):254-258;270.
HUANG B, LIU W J, FANG L, et al. Simultaneous analysis of catechins in several Fujian oolong tea and white tea products by UPLC-MS/MS[J]. Science and Technology of Food Industry, 2020, 41(10):254-258; 270.
[15] 肖观林, 江洁怡, 李素梅, 等. 基于UPLC-Q-TOF-MS/MS技术的布渣叶化学成分分析[J]. 中国实验方剂学杂志, 2021, 27(3):138-148.
XIAO G L, JIANG J Y, LI S M, et al. Analysis of chemical constituents in microctis folium by UPLC-Q-TOF-MS/MS[J]. Chinese Journal of Experimental Traditional Medical Formulae, 2021, 27(3):138-148.
[16] 杨代晓, 陈晓静, 胡秋菊, 等. 液相色谱—质谱联用法分析葡萄籽提取物中的5种多酚类成分[J]. 药物分析杂志, 2016, 36(8):1330-1337.
YANG D X, CHEN X J, HU Q J, et al. LC-MS method for determination of 5 kinds of polyphenols in grape seed extract[J]. Chinese Journal of Pharmaceutical Analysis, 2016, 36(8):1330-1337.
[17] 谭金桃, 马丹凤, 方艳, 等. 基于UPLC-ESIQ-TOF-MS法分析灯台叶颗粒的主要活性成分[J]. 中南药学, 2017, 15(8):1111-1114.
TAN J T, MA D F, FANG Y, et al. Identification and characterization of active chemical constituents in Dengtaiye particles with UPLC-ESIQ-TOF-MS[J]. Central South Pharmacy, 2017, 15(8):1111-1114.
[18] 武俊颖, 张武岗, 郎一帆, 等. 基于UPLC-Q-TOF-MS/MS的芒果核化学成分分析[J]. 天然产物研究与开发, 2023, 35(6):949-965.
WU J Y, ZHANG W G, LANG Y F, et al. Chemical composition analysis of mango kernels by UPLC-Q-TOF-MS/MS[J]. Natural Product Research and Development, 2023, 35(6):949-965.
[19] 吴福林, 李平亚, 董庆海, 等. 基于UPLC-Q-TOF/MS分析止痛化徵胶囊的入血成分[J]. 中国中药杂志, 2018, 43(21):4339-4346.
WU F L, LI P Y, DONG Q H, et al. Absorbed components analysis of Zhitong Huazheng Capsules in rat serum by UPLC-Q-TOF/MS[J]. China Journal of Chinese Materia Medica, 2018, 43(21):4339-4346.
[20] 罗媛, 王昌权, 巩仔鹏, 等. UPLC-Q-TOF-MS/MS分析苗药云实皮的化学成分[J]. 中国药房, 2020, 31(20):2481-2486.
LUO Y, WANG C Q, GONG Z P, et al. Analysis of chemical compositions in Miao medicine Caesalpinia decapetala by UPLC-Q-TOF-MS/MS[J]. China Pharmacy, 2020, 31(20):2481-2486.
[21] YEO S C M, LUO W X, WU J Z, et al. Quantification of pinosylvin in rat plasma by liquid chromatography-tandem mass spectrometry: Application to a pre-clinical pharmacokinetic study[J]. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 2013, 931:68-74.
[22] 朱伟, 赵赫, 姚岚, 等. UFLC-MS/MS法同时测定肺宁颗粒中6种化学成分[J]. 解放军药学学报, 2017, 33(4):356-358, 362.
ZHU W, ZHAO H, YAO L, et al. Smimultaneous UFLC-MS/MS quantitation of six chemical components in feining granules[J]. Pharmaceutical Journal of Chinese PLA, 2017, 33(4):356-358, 362.
[23] 翁倩倩, 杨滨, 李斌, 等. 瓜拉纳化学成分的UPLC-Q-TOF-MS分析[J]. 中国实验方剂学杂志, 2021, 27(15):68-75.
WENG Q Q, YANG B, LI B, et al. Analysis of chemical constituents in Paullinia cupana dried seeds by UPLC-Q-TOF-MS[J]. Chinese Journal of Experimental Traditional Medical Formulae, 2021, 27(15):68-75.
[24] 王力彬, 冯甜, 王芳, 等. 基于UPLC-Q/Orbitrap/MS/MS对白虎加人参汤的全成分分析及化学成分鉴定[J]. 药物流行病学杂志, 2023, 32(2):198-206.
WANG L B, FENG T, WANG F, et al. Analysis and identification of chemical constituents of Baihu-plus-Renshen decoction based on UPLC-Q/Orbitrap/MS/MS[J]. Chinese Journal of Pharmacoepidemiology, 2023, 32(2):198-206.
[25] 白伟娟, 张小江, 柳训才, 等. UPLC-MS/MS测定燕窝中18种氨基酸[J]. 食品工业, 2022, 43(10):296-302.
BAI W J, ZHANG X J, LIU X C, et al. Determination of 18 amino acids in edible bird’s nest using UPLC-MS/MS[J]. The Food Industry, 2022, 43(10):296-302.
Outlines

/