Development and Validation of Methods for the Determination of Anthocyanins in Physiological Fluids Via UHPLC-MS

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 Jan 30

PMID 31991680

Citations 5

Authors

Michael Kaiser

Lisa Muller-Ehl

Maike Passon

Andreas Schieber

Affiliations

Soon will be listed here.

Abstract

Recent in vitro and in vivo studies on anthocyanins confirmed numerous health-promoting effects in humans. Daily anthocyanin intake can be estimated via food databases, but the amount absorbed by the organism still remains uncertain because anthocyanin bioavailability is yet to be elucidated in its entirety. For this purpose, suitable and validated methods of sample preparation and analysis are required. Therefore, a sample preparation method for anthocyanin metabolite analysis in plasma was successfully established and validated. The validation yielded acceptable results for the anthocyanins in terms of recovery (54-108%) and precision (coefficient of variation (CV) < 15%). The UHPLC-MS method used in the consecutive reaction monitoring (CRM) mode was sufficiently sensitive, resulting in limits of detection <2.3 ng/mL and limits of quantification < 8.1 ng/mL with associated repeatability of the MS system with CVs of <5.1%. In addition, a method for the sum parameter determination of anthocyanidins in urine comprising solely the evaporation of acidified samples was developed, validated, and successfully applied to real samples. The results showed that this method is applicable for the methylated anthocyanidins, but not for the hydroxylated anthocyanidins, due to the chosen CRM modes required for optimum selectivity.

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References

Furey A, Moriarty M, Bane V, Kinsella B, Lehane M . Ion suppression; a critical review on causes, evaluation, prevention and applications. Talanta. 2013; 115:104-22. DOI: 10.1016/j.talanta.2013.03.048. View

Hribar U, Poklar Ulrih N . The metabolism of anthocyanins. Curr Drug Metab. 2013; 15(1):3-13. DOI: 10.2174/1389200214666131211160308. View

Delgado-Vargas F, Jimenez A, Paredes-Lopez O . Natural pigments: carotenoids, anthocyanins, and betalains--characteristics, biosynthesis, processing, and stability. Crit Rev Food Sci Nutr. 2000; 40(3):173-289. DOI: 10.1080/10408690091189257. View

Nurmi T, Mursu J, Heinonen M, Nurmi A, Hiltunen R, Voutilainen S . Metabolism of berry anthocyanins to phenolic acids in humans. J Agric Food Chem. 2009; 57(6):2274-81. DOI: 10.1021/jf8035116. View

Kalt W, Liu Y, McDonald J, Vinqvist-Tymchuk M, Fillmore S . Anthocyanin metabolites are abundant and persistent in human urine. J Agric Food Chem. 2014; 62(18):3926-34. DOI: 10.1021/jf500107j. View

Schmitt S, Tratzka S, Schieber A, Passon M . Hemisynthesis of Anthocyanin Phase II Metabolites by Porcine Liver Enzymes. J Agric Food Chem. 2019; 67(22):6177-6189. DOI: 10.1021/acs.jafc.9b01315. View

Shim S, Kim J, Choi C, Kim C, Park K . Ginkgo biloba extract and bilberry anthocyanins improve visual function in patients with normal tension glaucoma. J Med Food. 2012; 15(9):818-23. PMC: 3429325. DOI: 10.1089/jmf.2012.2241. View

Liu J, Song J, Huang K, Michel D, Fang J . HPLC-MS/MS analysis of anthocyanins in human plasma and urine using protein precipitation and dilute-and-shoot sample preparation methods, respectively. Biomed Chromatogr. 2017; 32(5):e4177. DOI: 10.1002/bmc.4177. View

Hibbert D . Systematic errors in analytical measurement results. J Chromatogr A. 2007; 1158(1-2):25-32. DOI: 10.1016/j.chroma.2007.03.021. View

10.

Giordano L, Coletta W, Rapisarda P, Donati M, Rotilio D . Development and validation of an LC-MS/MS analysis for simultaneous determination of delphinidin-3-glucoside, cyanidin-3-glucoside and cyanidin-3-(6-malonylglucoside) in human plasma and urine after blood orange juice administration. J Sep Sci. 2007; 30(18):3127-36. DOI: 10.1002/jssc.200700246. View

11.

Kaiser M, Lacheta B, Passon M, Schieber A . An Innovative Approach to the Preparation of Plasma Samples for UHPLC-MS Analysis. J Agric Food Chem. 2019; 67(23):6665-6671. DOI: 10.1021/acs.jafc.9b01782. View

12.

Rose C, Parker A, Jefferson B, Cartmell E . The Characterization of Feces and Urine: A Review of the Literature to Inform Advanced Treatment Technology. Crit Rev Environ Sci Technol. 2015; 45(17):1827-1879. PMC: 4500995. DOI: 10.1080/10643389.2014.1000761. View

13.

de Ferrars R, Cassidy A, Curtis P, Kay C . Phenolic metabolites of anthocyanins following a dietary intervention study in post-menopausal women. Mol Nutr Food Res. 2013; 58(3):490-502. DOI: 10.1002/mnfr.201300322. View

14.

Muller D, Schantz M, Richling E . High performance liquid chromatography analysis of anthocyanins in bilberries (Vaccinium myrtillus L.), blueberries (Vaccinium corymbosum L.), and corresponding juices. J Food Sci. 2012; 77(4):C340-5. DOI: 10.1111/j.1750-3841.2011.02605.x. View

15.

Miyake S, Takahashi N, Sasaki M, Kobayashi S, Tsubota K, Ozawa Y . Vision preservation during retinal inflammation by anthocyanin-rich bilberry extract: cellular and molecular mechanism. Lab Invest. 2011; 92(1):102-9. DOI: 10.1038/labinvest.2011.132. View

16.

Richter R, Schulz-Knappe P, Schrader M, Standker L, Jurgens M, TAMMEN H . Composition of the peptide fraction in human blood plasma: database of circulating human peptides. J Chromatogr B Biomed Sci Appl. 1999; 726(1-2):25-35. DOI: 10.1016/s0378-4347(99)00012-2. View

17.

Behrends A, Weber F . Influence of Different Fermentation Strategies on the Phenolic Profile of Bilberry Wine (Vaccinium myrtillus L.). J Agric Food Chem. 2017; 65(34):7483-7490. DOI: 10.1021/acs.jafc.7b02268. View

18.

Czank C, Cassidy A, Zhang Q, Morrison D, Preston T, Kroon P . Human metabolism and elimination of the anthocyanin, cyanidin-3-glucoside: a (13)C-tracer study. Am J Clin Nutr. 2013; 97(5):995-1003. DOI: 10.3945/ajcn.112.049247. View

19.

Zimmermann B, Papagiannopoulos M, Brachmann S, Lorenz M, Stangl V, Galensa R . A shortcut from plasma to chromatographic analysis: straightforward and fast sample preparation for analysis of green tea catechins in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2009; 877(8-9):823-6. DOI: 10.1016/j.jchromb.2009.01.013. View

20.

Mulleder U, Murkovic M, Pfannhauser W . Urinary excretion of cyanidin glycosides. J Biochem Biophys Methods. 2002; 53(1-3):61-6. DOI: 10.1016/s0165-022x(02)00093-3. View