Characterization of urinary bioactive phenolic metabolites excreted after consumption of a cup of mountain tea (Sideritis scardica) using liquid chromatography – tandem mass spectrometry

Authors

  • Jasmina Petreska Stanoeva Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril & Methodius University, Skopje
  • Daniela Bagashovska Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril & Methodius University, Skopje
  • Marina Stefova Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Skopje

DOI:

https://doi.org/10.20450/mjcce.2012.41

Keywords:

Sideritis, mountain tea, flavonoids, polyphenols, metabolites, bioavailability

Abstract

A nutrition experiment was performed for studying the bioavailability of polyphenols from Sideritis with healthy human subjects, who consumed a standardized Sideritis decoction after which urine was collected and analyzed. 35 polyphenolic compounds in the ingested decoction and 63 of their metabolites in urine collected after ingestion were identified using HPLC/MSn. It was shown that polyphenols present in Sideritis decoction are extensively conjugated to glucuronides, sulfates and also transformed to methylated forms after oral administration. In the analyzed urine samples, 31 different metabolites of hypolaetin, methylhypolaetin, isoscutellarein, methylisoscutellarein and apigenin, and 32 phenolic acids metabolites were detected, hypolaetin and isoscutellarein metabolites being the most abundant. This enabled polyphenols metabolites patterns to be obtained, which is a crucial step towards revealing the bioavailability and metabolism of phenolic compounds from Sideritis in human. The identification and structure elucidation of these metabolites provided essential data for further studies of Sideritis polyphenols bioavailability.

References

E. González-Burgos, M.E. Carretero, M.P. Gómez-Serranillos, Sideritis spp.:Uses, chemical composition and pharmacological activities. A review, J. Ethnopharmacol. 135, 209–225, (2011).

M.I. Gil, F. Ferreres, A. Marrero, F. Tomas-Lorente, F.A. Tomas-Barberan, Distribution of flavonoid aglycones and glycosides in Sideritis species from the Canary Islands and Maderia, Phytochemistry 34, 227–232, (1993).

F.A. Tomas-Barberan, M.I. Gil, F. Ferreres, D. Rivera, C. Obon, F. Tomas-Lorente Distribution of 8-hydroxyflavone glycosides and flavonoid aglycones in some Spanish Sideritis species, Biochem. Syst. Ecol. 21, 487–497, (1993).

A. Sattar, V. Bankova, S. Popov, Flavonoid glycosides from Sideritis species, Fitoterapia 64, 278–279, (1993).

A. Sattar, V. Bankova, S. Popov, Acylated flavonoid glycosides from Sideritis Scardica, Fitoterapia 66, 190, (1995).

J. Petreska, M. Stefova, F. Ferreres, D.A. Moreno, F.A. Tomás-Barberán, G. Stefkov, S. Kulevanova, A. Gil-Izquierdo, Potential bioactive phenolics of Macedonian Sideritis species used for medicinal "Mountain Tea", Food Chem. 125, 13–20, (2011).

J. Petreska, G. Stefkov, S. Kulevanova, K. Alipieva, V. Bankova, M. Stefova, Phenolic compounds of Mountain Tea from the Balkans: LC/DAD/ESI/MSn profile and content, Nat. Prod. Commun. 6, 21–30, (2011).

B.M. Fraga, Phytochemistry and chemotaxonomy of Sideritis species from the Mediterranean region, Phytochemistry 76, 7–24, (2012).

N. Ezer, M.K. Sakar, B. Rodríguez, M.C. De La Torre, Flavonoid glycosides and a phenyl propanoidglycoside from Sideritis perfoliata, Int. J. Pharmacogn. 30, 61–65, (1992).

G. Williamson, C. Manach, Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies, Am. J. Clin. Nutr. 81, 243S–255S, (2005).

J. Petreska, M. Stefova, F. Ferreres, D.A. Moreno, F.A. Tomás-Barberán, G. Stefkov, S. Kulevanova, A. Gil-Izquierdo, Dietary Burden of Phenolics Per Serving of “Mountain Tea” (Sideritis) from Macedonia and Correlation to Antioxidant Activity, Nat. Prod. Commun. 6, 1305–1314, (2011).

K. Alipieva, J. Petreska, Á. Gil-Izquierdo, M. Stefova, Lj. Evstatieva, V. Bankova, Influence of the extraction method on the yield of flavonoids and phenolics from Sideritis spp. (Pirin Mountain tea), Nat. Prod. Commun. 5, 51–54, (2010).

A.A. Sattar, Flavonoids and Terpenoids in Some Representatives of Lamiaceae Family, Bulgarian Academy of Sciences, Sofia, 1994.

K.D.R. Setchell, A. Cassidy, Dietary Isoavones: Biological Effects and Relevance to Human Health, J. Nutr. 129, 758S–¦767S, (1999).

D.H. Kim, E.A. Jung, I.S. Sohng, J.A. Han, T.H. Kim, M.J. Han, Intestinal bacterial metabolism of flavonoids and its relation to some biological activities, Arch. Pharm. Res. 21, 17–23, (1998).

J. Winter, L.H. Moore, V.R. Dowell, V.D. Bokkenheuser, C-ring cleavage of flavonoids by human intestinal bacteria, Appl. Environ. Microbiology 55, 1203–1208, (1989).

A.J. Day, M.S. Du Pont, S. Ridley, M. Rhodes, M.J. Rhodes, M.R. Morgan, Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver β-glucuronidase activity, FEBS Lett. 436, 71–75, (1998).

C. Jia, H. Shi, W. Jin, K. Zhang, Y. Jiang, M. Zhao, P. Tu Metabolism of Echinacoside, a Good Antioxidant, in Rats: Isolation and Identification of Its Biliary Metabolites, Drug Metab. Dispos. 37, 431–438, (2009).

G. Williamson, G.W. Plumb, Y. Uda, K.R. Price, M.J.C. Price, Dietary quercetin glycosides: antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepa1c1c7 cells, Carcinogenesis 17, 2385–2387, (1996).

Downloads

Published

2012-12-20

How to Cite

Petreska Stanoeva, J., Bagashovska, D., & Stefova, M. (2012). Characterization of urinary bioactive phenolic metabolites excreted after consumption of a cup of mountain tea (Sideritis scardica) using liquid chromatography – tandem mass spectrometry. Macedonian Journal of Chemistry and Chemical Engineering, 31(2), 229–243. https://doi.org/10.20450/mjcce.2012.41

Issue

Vol. 31 No. 2 (2012)

Section

Analytical Chemistry

License

The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)

  • Adapt — remix, transform, and build upon the material
  • for any purpose, even commercially.
The licensor cannot revoke these freedoms as long as you follow the license terms.

 Under the following terms:

  • Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.

  • NonCommercial — You may not use the material for commercial purposes.

Most read articles by the same author(s)

> >>