Phytomedicine
Volume 16, Issue 2 , Pages 233-243 , March 2009

Liquid chromatography tandem mass spectrometry identification of proanthocyanidins in rat plasma after oral administration of grape seed extract

  • Jeevan K. Prasain

      Affiliations

    • Departments of Pharmacology & Toxicology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • Purdue-UAB Botanicals Center for Age-Related Disease, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • Corresponding Author InformationCorresponding author at: Department of Pharmacology & Toxicology, MCLM 456, University of Alabama at Birmingham, 1918 University Boulevard, Birmingham, AL 35294, USA. Tel.: +12059962612; fax: +12059346944.
    • ,
  • Ning Peng

      Affiliations

    • Department of Cell Biology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Yanying Dai

      Affiliations

    • Department of Cell Biology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Ray Moore

      Affiliations

    • Comprehensive Cancer Center Proteomics/Mass Spectrometry Shared Facility, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Alireza Arabshahi

      Affiliations

    • Departments of Pharmacology & Toxicology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Landon Wilson

      Affiliations

    • Comprehensive Cancer Center Proteomics/Mass Spectrometry Shared Facility, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Stephen Barnes

      Affiliations

    • Departments of Pharmacology & Toxicology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • Purdue-UAB Botanicals Center for Age-Related Disease, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • Comprehensive Cancer Center Proteomics/Mass Spectrometry Shared Facility, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • J. Michael Wyss

      Affiliations

    • Department of Cell Biology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • Purdue-UAB Botanicals Center for Age-Related Disease, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Helen Kim

      Affiliations

    • Departments of Pharmacology & Toxicology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • Purdue-UAB Botanicals Center for Age-Related Disease, University of Alabama at Birmingham, Birmingham, AL 35294, USA
    • ,
  • Ray L. Watts

      Affiliations

    • Department of Neurology, University of Alabama at Birmingham, Birmingham, AL 35294, USA

References 

  1. Baba S, Osakabe N, Natsume M, Terao J. Absorption and urinary excretion of procyanidin B2 [epicatechin-(4β-8)-epicatechin] in rats. Free Rad. Biol. Med. 2002;33:142–148
  2. Boukharat M. Procyanidines galloylées du sarment de vigne (Vitis vinifera) Séparation et identification par chromatographie liquide haute performance et chromatographie en phase gazeuse. Chromatography. 1988;455:406–409
  3. da Silva JMR, Rigaud J, Cheynier V, Cheminat A, Moutonet M. Procyanidin dimers and trimers from grape seeds. Phytochemistry. 1991;30:1259–1264
  4. Deprez S, Brezillon C, Rabot S, Philippe C, Mila I, Lapierre C, et al. Polymeric proanthocyanidins are catabolized by human colonic microflora into low-molecular-weight phenolic acids. J. Nutr. 2000;130:2733–2738
  5. Deprez S, Mila I, Huneau JF, Tome D, Scalbert A. Transport of proanthocyanidin dimer, trimer, and polymer across monolayers of human intestinal epithelial caco-2 cells. Antioxid. Redox Signal. 2001;3:957–967
  6. Deshane J, Chaves L, Sarikonda KV, Isbell S, Wilson L, Kirk M, et al. Proteomics analysis of rat brain protein modulations by grape seed extract. J. Agric. Food Chem. 2004;52:7872–7883
  7. Donovan JL, Bell JR, Kasim-Karakas S, German JB, Walzem RL, Hansen RJ, et al. Catechin is present as metabolites in human plasma after consumption of red wine. J. Nutr. 1999;129:1662–1668
  8. Donovan JL, Manach C, Rios L, Morand C, Scalbert A, Rémésy C. Procyanidins are not bioavailable in rats fed a single meal containing a grape seed extract or the procyanidin dimer B 3. Br. J. Nutr. 2002;87:299–306
  9. El Mohsen MMA, Kuhnler G, Rechner AR, Schroeter H, Rose S, Jenner P, et al. Uptake and metabolism of epicatechin and its access to the brain after oral ingestion. Free Rad. Biol. Med. 2002;33:1693–1702
  10. Faria A, Mateus N, de Freitas V, Calhau C. Modulation of MPP+uptake by procyanidins in Caco-2 cells: involvement of oxidation/reduction reactions. FEBS Lett. 2006;580:155–160
  11. Feng Y, Liu YM, Leblanc MH, Bhatt AJ, Rhodes PG. Grape seed extract given three hours after injury suppresses lipid peroxidation and reduces hypoxic-ischemic brain injury in neonatal rats. Pediatr. Res. 2007;61:295–300
  12. García-Ramírez B, Fernandez-Larrea J, Salvadó MJ, Ardèvol A, Arola L, Bladé C. Tetramethylated dimeric procyanidins are detected in rat plasma and liver early after oral administration of synthetic oligomeric procyanidins. J. Agric. Food Chem. 2006;54:2543–2551
  13. Holt RR, Lazarus SA, Sullards MC, Zhu QY, Schramm DD, Hammerstone JF, et al. Procyanidin dimer B2 [epicatechin-(4β-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa. Am. J. Clin. Nutr. 2002;76:798–804
  14. Hong YJ, Mitchell AE. Metabolic profiling of flavonol metabolites in human urine by liquid chromatography and tandem mass spectrometry. J. Agric. Food Chem. 2004;52:6794–6801
  15. Howell AB, Vorsa N, Marderosian AD, Foo LY. Inhibition of the adherence of p-fimbriated Escherichia coli to uroepithelial-cell surfaces by proanthocyanidin extracts from Cranberries. N. Engl. J. Med. 1998;339:1085–1086
  16. Kahle K, Huemmer W, Kempf M, Scheppach W, Erk T, Richling E. Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption. J. Agric. Food Chem. 2007;55:10605–10614
  17. Koga T, Moro K, Nakamori K, Yamakoshi J, Hosoyama H, Kataoka S, et al. Increase in oxidative potential of rat plasma by oral administration of proanthocyanidin-rich extract from grape seeds. J. Agric. Food Chem. 1999;47:1892–1897
  18. Masukawa Y, Matsui Y, Shimizu N, Kondou N, Endou H, Kuzukawa M, et al. Determination of green tea catechins in human plasma using liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 2006;834:26–34
  19. Nagai M, Conney AH, Zhu BT. Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase. Drug Metab. Dispos. 2004;32:497–504
  20. Nowack R, Schmitt W. Cranberry juice for prophylaxis of urinary tract infections—Conclusions from clinical experience and research. Phytomedicine. 2008;15:653–667
  21. Pataki T, Bak I, Kovacs P, Bagchi D, Das DK, Tosaki A. Grape seed proanthocyanidins improved cardiac recovery during reperfusion after ischemia in isolated rat hearts. Am. J. Clin. Nutr. 2002;75:894–899
  22. Peng HW, Cheng FC, Huang YT, Chen CF, Tsai TH. Determination of naringenin and its glucuronide conjugate in rat plasma and brain tissue by high-performance liquid chromatography. J. Chromatogr. B: Biomed. Sci. Appl. 1998;714:369–374
  23. Piskula MK, Terao J. Accumulation of (−)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rat tissues. J. Nutr. 1998;128:1172–1178
  24. Prasain JK, Jones K, Brissie N, Moore R, Wyss JM, Barnes S. Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry. J. Agric. Food Chem. 2004;52:3708–3712
  25. Prieur C, Rigaud J, Cheynier V, Moutounet M. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry. 1994;36:781–784
  26. Reed JD, Krueger CG, Vestling MM. MALDI-TOF mass spectrometry of oligomeric food polyphenols. Phytochemistry. 2005;66:2248–2263
  27. Rein D, Lotito S, Holt RR, Keen CL, Schmitz HH, Fraga CG. Epicatechin in human plasma: in vivo determination and effect of chocolate consumption on plasma oxidation status. J. Nutr. 2000;130:2109S–2114S
  28. Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M. Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci. Biotechnol. Biochem. 2003;67:1140–1143
  29. Shoji T, Masumoto S, Moriichi N, Akiyama H, Kanda T, Ohtake Y, et al. Apple procyanidin oligomers absorption in rats after oral administration: analysis of procyanidins in plasma using the porter method and high-performance liquid chromatography/tandem mass spectrometry. J. Agric. Food Chem. 2006;54:884–892
  30. Sun B, Belchior GP, Ricardo da Silva JM, Spranger MI. Isolation and purification of dimeric and trimeric procyanidins from grape seeds. J. Chromatogr. A. 1999;841:115–121
  31. Tsang C, Auger C, Mullen W, Bornet A, Rouanet JM, Crozier A, et al. The absorption, metabolism and excretion of flavan-3-ols and procyanidins following the ingestion of a grape seed extract by rats. Br. J. Nutr. 2005;94:170–181
  32. Yamaguchi F, Yoshimura Y, Nakazawa H, Ariga T. Free radical scavenging activity of grape seed extract and antioxidants by electron spin resonance spectrometry in an H2O2/NaOH/DMSO system. J. Agric. Food Chem. 1999;47:2544–2548
  33. Yamakoshi J, Saito M, Kataoka S, Tokutake S. Procyanidin-rich extract from grape seeds prevents cataract formation in hereditary cataractous (ICR/f) rats. J. Agric. Food Chem. 2002;50:4983–4988
  34. Yang CS, Chen L, Lee MJ, Balentine D, Kuo MC, Schantz SP. Blood and urine levels of tea catechins after ingestion of different amounts of green tea by human volunteers. Cancer Epidemiol. Biomarkers Prev. 1998;7:351–354

PII: S0944-7113(08)00178-5

doi: 10.1016/j.phymed.2008.08.006

Phytomedicine
Volume 16, Issue 2 , Pages 233-243 , March 2009

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