Food and Fermentation Industries >

2024 , Vol. 50 >Issue 2: 288 - 295

DOI: https://doi.org/10.13995/j.cnki.11-1802/ts.035236

A rapid ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry method for simultaneous detection of coumarins in Citrus medica L. var. sarcodactylis swingle

  • ZHOU Huyi ,
  • ZHAO Xijuan ,
  • JIAO Bining
Expand
  • 1(Southwest University/Chinese Academy of Agricultural Sciences, Chongqing 400712, China)
    2(Laboratory of Quality and Safety Risk Assessment for Citrus Products, Ministry of Agriculture and Rural Affairs, Chongqing 400712, China)
    3(Quality Supervision and Testing Center for Citrus and Seedling, Ministry of Agriculture and Rural Affair, Chongqing 400712, China)
    4(College of Horticulture and Landscape Architecture, Southwest University, Chongqing 400715, China)

Received date: 2023-02-23

  Revised date: 2023-03-22

  Online published: 2024-02-27

Fold

Abstract

Citrus medica L. var. sarcodactylis swingle can be used as both food and medicine, and coumarins are one of its key bioactive components. There is currently no accurate method for the quick detection and comprehensive quantitation of a series of coumarins owing to their structural similarity and some isomers. In this study, an ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry (UPLC-QqQ-MS/MS) approach was developed for the qualitative and quantitative detection of 41 coumarins in Citrus medica L. var. sarcodactylis swingle. In brief, within a 14-minute chromatographic run, 16 simple coumarins, 23 furocoumarins, and 2 other coumarins, especially 8 groups of isomers, were separated simultaneously. Recoveries, linear correlation coefficients, detection and quantitation limits, as well as inter-day and intra-day precisions, were used to validate this newly developed method. The method can be utilized for the screening and measurement of coumarins in Citrus medica L. var. sarcodactylis swingle because it has been verified to have high sensitivity, accuracy, and good recoveries. Four coumarins including 8-geranyloxypsoralen, bergamottin, isopimpinellin, and meranzin hydrate were reported for the first time in the fingered citron fruits. This is by far the most comprehensive and quick method to identify and determine coumarins in fingered citrons.

Key words： fingered citron; coumarins; ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry

Cite this article

ZHOU Huyi , ZHAO Xijuan , JIAO Bining . A rapid ultra-high-performance liquid chromatography with triple quadrupole mass spectrometry method for simultaneous detection of coumarins in Citrus medica L. var. sarcodactylis swingle[J]. Food and Fermentation Industries, 2024 , 50(2) : 288 -295 . DOI: 10.13995/j.cnki.11-1802/ts.035236

References

[1] 国家药典委员会. 中华人民共和国药典(2020版一部)[M].北京:中国医药科技出版社, 2020:185-186.
Chinese Pharmacopoeia Commission.Pharmacopoeia of the People′s Republic of China (2020, Volume 1)[M].Beijin:China Medical Science Press, 2020:185-186.
[2] WU Z, LI H, TU D W, et al.Extraction optimization, preliminary characterization, and in vitro antioxidant activities of crude polysaccharides from finger citron[J].Industrial Crops and Products, 2013, 44:145-151.
[3] LUO X G, WANG J, CHEN H Q, et al.Identification of flavoanoids from finger citron and evaluation on their antioxidative and antiaging activities[J].Frontiers in Nutrition, 2020, 7:584900.
[4] JI L N, FAN X M, HOU X L, et al.Jieduquyuziyin prescription suppresses inflammatory activity of MRL/lpr mice and their bone marrow-derived macrophages via inhibiting expression of IRAK1-NF-κB signaling pathway[J].Frontiers in Pharmacology, 2020, 11:1049.
[5] WANG E W, LI Y Q, MAGUY B L, et al.Separation and enrichment of phenolics improved the antibiofilm and antibacterial activity of the fractions from Citrus medica L.var.sarcodactylis in vitro and in tofu[J].Food Chemistry, 2019, 294:533-538.
[6] MA Q G, TANG Y, SANG Z P, et al.Structurally diverse biflavonoids from the fruits of Citrus medica L.var.sarcodactylis Swingle and their hypolipidemic and immunosuppressive activities[J].Bioorganic Chemistry, 2021, 117:105450.
[7] PENG B, YANG J N, HUANG W J, et al.Structural characterization and immunoregulatory activity of a novel heteropolysaccharide from bergamot (Citrus medica L.var.sarcodactylis) by alkali extraction[J].Industrial Crops and Products, 2019, 140:111617.
[8] CHAN Y Y, HWANG T L, KUO P C, et al.Constituents of the fruits of Citrus medica L.var.sarcodactylis and the effect of 6,7-Dimethoxy-coumarin on superoxide anion formation and elastase release[J].Molecules, 2017, 22(9):1454.
[9] CHU J, LI S L, YIN Z Q, et al.Simultaneous quantification of coumarins, flavonoids and limonoids in Fructus Citri Sarcodactylis by high performance liquid chromatography coupled with diode array detector[J].Journal of Pharmaceutical and Biomedical Analysis, 2012, 66:170-175.
[10] 吴学峰, 谢斌, 黄晓兰, 等.基于UPLC-Q-TOF MS技术快速鉴定蒸制广佛手化学成分[J].质谱学报, 2021, 42(3):207-217.
WU X F, XIE B, HUANG X L, et al.Rapid analysis compositions of processed Citrus medica L.var.sarcodactylis swingle by UPLC-Q-TOF MS[J].Journal of Chinese Mass Spectrometry Society, 2021, 42(3):207-217.
[11] 魏莹, 陈珍, 杨兰, 等.HPLC法同时测定不同产地佛手中5个成分的含量[J].药物分析杂志, 2017, 37(12):2180-2184.
WEI Y, CHEN Z, YANG L, et al.Simultaneous determination of 5 components in Fructus Citris Sarcodactylis from different habitats by HPLC[J].Chinese Journal of Pharmaceutical Analysis, 2017, 37(12):2180-2184.
[12] 孙全, 徐冲, 刘霞, 等.HPLC同时测定川佛手中的橙皮苷与5,7-二甲氧基香豆素[J].华西药学杂志, 2017, 32(6):646-648.
SUN Q, XU C, LIU X, et al.Simultaneous determination of aurantiamarin and 5,7-dimethoxycoumarin in citri sarcodactylis fructus from Sichuan by HPLC[J].West China Journal of Pharmaceutical Sciences, 2017, 32(6):646-648.
[13] 胡瀚文, 赵永艳, 杨天龙, 等.基于UPLC-Q-Orbitrap HRMS的川佛手化学成分分析[J].中国实验方剂学杂志, 2020, 26(7):148-155.
HU H W, ZHAO Y Y, YANG T L, et al.Analysis and identification of chemical constituents of citri sarcodactylis fructus by UPLC-Q-orbitrap HRMS[J].Chinese Journal of Experimental Traditional Medical Formulae, 2020, 26(7):148-155.
[14] ZHONG Y M, FENG Y F, WU X, et al.Rapid identification of coumarins from Fructus citri sarcodactylis by UPLC/Q-TOF-MS[J].Natural Product Research, 2015, 29(1):53-58.
[15] 钟艳梅, 冯毅凡, 郭姣.基于UPLC-Q-TOF-MS的广佛手化学成分快速鉴定研究[J].天然产物研究与开发, 2014, 26(12):1965-1970;2040.
ZHONG Y M, FENG Y F, GUO J.Rapid identification of components from Fructus citri sarcodactylis based on ultra-high performance liquid chromatography time-of-flight mass spectrometry[J].Natural Product Research and Development, 2014, 26(12):1965-1970;2040.
[16] 吴春蓉. 佛手物质基础及质量评价研究[D].广州:广东药科大学, 2018.
WU C R.Study on the material base and quality evaluation of fructus citrus sarcodactylis[D].Guangzhou:Guangdong Pharmaceutical University, 2018.
[17] 王晋. 佛手总黄酮的分离纯化及其抗氧化活性研究[D].广州:华南农业大学, 2018.
WANG J.Studeies on separation, purification and antioxidant activities of bergamot total flavonoids[D].Guangzhou:South China Agricultural University, 2018.
[18] 臧文静. 不同品种柑橘果实黄酮类化合物组分鉴定与抗氧化活性研究[D].杭州:浙江大学, 2019.
ZANG W J.Identification and determination of flavonoids from different Citrus cultivars fruit and their antioxidant activity[D].Hangzhou:Zhejiang University, 2019.
[19] KATSORI A M, HADJIPAVLOU-LITINA D.Coumarin derivatives:An updated patent review (2012-2014)[J].Expert Opinion on Therapeutic Patents, 2014, 24(12):1323-1347.
[20] NAOWABOOT J, SOMPARN N, SAENTAWEESUK S, et al.Umbelliferone improves an impaired glucose and lipid metabolism in high-fat diet/streptozotocin-induced type 2 diabetic rats[J].Phytotherapy Research, 2015, 29(9):1388-1395.
[21] MIRA A, YAMASHITA S, KATAKURA Y, et al.In vitro neuroprotective activities of compounds from Angelica shikokiana Makino[J].Molecules, 2015, 20(3):4813-4832.
[22] KHOMENKO T M, ZARUBAEV V V, ORSHANSKAYA I R, et al.Anti-influenza activity of monoterpene-containing substituted coumarins[J].Bioorganic & Medicinal Chemistry Letters, 2017, 27(13):2920-2925.
[23] MA S N, LI Q, FENG Y M, et al.Simultaneous determination of five coumarins in Peucedanum decursivum radix by UPLC[J].Journal of Chromatographic Science, 2022, 60(2):173-178.
[24] DUGO P, RUSSO M, SARÒ M, et al.Multidimensional liquid chromatography for the determination of chiral coumarins and furocoumarins in Citrus essential oils[J].Journal of Separation Science, 2012, 35(14):1828-1836.
[25] HROBOŇOVÁ K, SÁDECKÁ J, ČIŽMÁRIK J.HPLC separation and determination of dicoumarol and other simple coumarins in sweet clover[J].Nova Biotechnologica et Chimica, 2018, 17(1):95-102.
[26] GUO P M, PANG W H, ZHAO X J, et al.A rapid UPLC-QqQ-MS/MS method for targeted screening and quantitative analysis of secondary metabolites in satsuma mandarin[J].European Food Research and Technology, 2021, 247(7):1725-1736.
[27] 谭涛, 董思龙, 秦艳, 等.佛手类黄酮和香豆素类物质的靶向筛查和定量分析研究[J].食品与发酵工业, 2023,49(18):297-305.
TAN T, DONG S L, QIN Y, et al.Targeted screening and quantitative analysis of flavonoids and coumarins in fingered citron (Citrus medica L.var.sarcodactylis Swingle)[J].Food and Fermentation Industries, 2023,49(18):297-305.
Options
Outlines

/

〈 〉

Powered by Beijing Magtech Co. Ltd,.