Quantification of Se-Methylselenocysteine and Its γ-Glutamyl Derivative from Naturally Se-Enriched Green Bean (Phaseolus vulgaris vulgaris) After HPLC-ESI-TOF-MS and Orbitrap MSn-Based Identification

Food Analytical Methods

Volumn 7, Issue 5, 2014, Pages 1147-1157

  Shao, Shuxun ^a   Mi, Xiubo ^a,b   Ouerdane, Laurent ^c   Lobinski, Ryszard ^c,f   García Reyes, Juan Francisco ^d   Molina Díaz, Antonio ^d   Vass, Andrea ^e   Dernovics, Mihály ^e  

^a INSTITUTE OF GEOCHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c CNRS   (France)

^d UNIVERSITY OF JAÉN   (Spain)

^e Operációkutatás és Aktuáriustudományok Tanszék docense   (Hungary)

^f WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Orbitrap; Phaseolus; Selenium; Speciation; Glutamyl Se methylselenocysteine

Indexed keywords

ELECTROSPRAY IONIZATION; INDUCTIVELY COUPLED PLASMA; INDUCTIVELY COUPLED PLASMA MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; SELENIUM;

COLLISION-INDUCED DISSOCIATION; ELECTROSPRAY IONIZATION (ESI); INDUCTIVELY COUPLED PLASMA MASS SPECTROMETRIES (ICPMS); MULTI-STEP PURIFICATION; ORBITRAP; PHASEOLUS; PROTEOLYTIC DIGESTION; SPECIATION;

SELENIUM COMPOUNDS;

EID: 84897443034     PISSN: 19369751     EISSN: 1936976X     Source Type: Journal    
DOI: 10.1007/s12161-013-9728-z     Document Type: Article

References (50)

1. Aureli F, Ouerdane L, Bierla K, Szpunar J, Prakash NT, Cubadda F (2012) Identification of selenosugars and other low-molecular weight selenium metabolites in high-selenium cereal crops. Metallomics 4: 968-978.
2. Bierla K, Dernovics M, Vacchina V, Szpunar J, Bertin G, Lobinski R (2008) Determination of selenocysteine and selenomethionine in edible animal tissues by 2D size-exclusion reversed-phase HPLC-ICP MS following carbamidomethylation and proteolytic extraction. Anal Bioanal Chem 390: 1789-1798.
3. Bierla K, Bianga J, Ouerdane L, Szpunar J, Yiannikouris A, Lobinski R (2013) A comparative study of the Se/S substitution in methionine and cysteine in Se-enriched yeast using an inductively coupled plasma mass spectrometry (ICP MS)-assisted proteomics approach. J Proteome 87: 26-39.
4. Brozmanová J, Mániková D, Vlcková V, Chovanec M (2010) Selenium: a double-edged sword for defense and offence in cancer. Arch Toxicol 84: 919-938.
5. Cao JJ, Gregoire BR, Zeng H (2012) Selenium deficiency decreases antioxidative capacity and is detrimental to bone microarchitecture in mice. J Nutr 142: 1526-1531.
6. Chan Q, Afton SE, Caruso JA (2010) Selenium speciation profiles in selenite-enriched soybean (Glycine max) by HPLC-ICPMS and ESI-ITMS. Metallomics 2: 147-153.
7. Dernovics M, Lobinski R (2008) Characterization of the selenocysteine-containing metabolome in selenium-rich yeast. J Anal At Spectrom 23: 744-751.
8. Dernovics M, Stefánka Z, Fodor P (2002) Improving selenium extraction by sequential enzymatic processes for Se-speciation of selenium-enriched Agaricus bisporus. Anal Bioanal Chem 372: 473-480.
9. Dernovics M, Ouerdane L, Tastet L, Giusti P, Preud'homme H, Lobinski R (2006) Detection and characterization of artefact compounds during selenium speciation analysis in yeast by ICP-MS-assisted MALDI MS, oMALDI MS/MS and LC-ES-MS/MS. J Anal At Spectrom 21: 703-707.
10. Dernovics M, Garcia-Barrera T, Bierla K, Preud'homme H, Lobinski R (2007) Standardless identification of selenocystathionine and its gamma-glutamyl derivatives in monkeypot nuts by 3D liquid chromatography with ICP-MS detection followed by nanoHPLC-Q-TOF-MS/MS. Analyst 132: 439-449.
11. n. Metallomics 1: 317-329.
12. EFSA (2012) Scientific opinion on safety and efficacy of selenium in the form of organic compounds produced by the selenium-enriched yeast Saccharomyces cerevisiae NCYC R646 (Selemax 1000/2000) as feed additive for all species. EFSA J 10: 2778-2794.
13. Freeman JL, Zhang LH, Marcus MA, Fakra S, McGrath SP, Pilon-Smits EAH (2006) Spatial imaging, speciation, and quantification of selenium in the hyperaccumulator plants Astragalus bisulcatus and Stanleya pinnata. Plant Physiol 142: 124-134.
14. Giada MDLR, Miranda MTM, Marquez UML (1998) Sulphur gamma-glutamyl peptides in mature seeds of common beans (Phaseolus vulgaris L.). Food Chem 61: 177-184.
15. Hart DJ, Fairweather-Tait SJ, Broadley MR, Dickinson SJ, Foot I, Knott P, McGrath SP, Mowat H, Norman K, Scott PR, Stroud JL, Tucker M, White PJ, Zhao FJ, Hurst R (2011) Selenium concentration and speciation in biofortified flour and bread: retention of selenium during grain biofortification, processing and production of Se-enriched food. Food Chem 126: 1771-1778.
16. Huang Y, Wang Q, Gao J, Lin Z, Banuelos GS, Yuan L, Yin X (2013) Daily dietary selenium intake in a high selenium area of Enshi, China. Nutrients 5: 700-710.
17. Hurst R, Armah CN, Dainty JR, Hart DJ, Teucher B, Goldson AJ, Broadley MR, Motley AK, Fairweather-Tait SJ (2010) Establishing optimal selenium status: results of a randomized, double-blind, placebo-controlled trial. Am J Clin Nutr 91: 923-931.
18. Infante HG, O'Connor G, Rayman M, Wahlen R, Entwisle J, Norris P, Hearn R, Catterick T (2004) Selenium speciation analysis of selenium-enriched supplements by HPLC with ultrasonic nebulisation ICP-MS and electrospray MS/MS detection. J Anal At Spectrom 19: 1529-1538.
19. Infante HG, O'Connor G, Rayman M, Wahlen R, Spallholz JE, Hearn R, Catterick T (2005) Identification of water-soluble gamma-glutamyl-Se-methylselenocysteine in yeast-based selenium supplements by reversed-phase HPLC with ICP-MS and electrospray tandem MS detection. J Anal At Spectrom 20: 864-870.
20. Ip C, Birringer M, Block E, Kotrebai M, Tyson JF, Uden PC, Lisk DJ (2000) Chemical speciation influences comparative activity of selenium-enriched garlic and yeast in mammary cancer prevention. J Agric Food Chem 48: 2062-2070.
21. Kápolna E, Laursen KH, Husted S, Larsen EH (2012) Bio-fortification and isotopic labelling of Se metabolites in onions and carrots following foliar application of Se and 77Se. Food Chem 133: 650-657.
22. Kotrebai M, Birringer M, Tyson JF, Block E, Uden PC (1999) Identification of the principal selenium compounds in selenium-enriched natural sample extracts by ion-pair liquid chromatography with inductively coupled plasma- and electrospray ionization-mass spectrometric detection. Anal Commun 36: 249-252.
23. Kotrebai M, Birringer M, Tyson JF, Block E, Uden PC (2000) Selenium speciation in enriched and natural samples by HPLC-ICP-MS and HPLC-ESI-MS with perfluorinated carboxylic acid ion-pairing agents. Analyst 125: 71-78.
24. Kozak L, Rudnicka M, Niedzielski P (2012) Determination of inorganic selenium species in dietary supplements by hyphenated analytical system HPLC-HG-AAS. Food Anal Methods 5: 1237-1243.
25. Larsen EH, Lobinski R, Burger-Meyer K, Hansen M, Ruzik R, Mazurowska L, Rasmussen PH, Sloth JJ, Scholten O, Kik C (2006) Uptake and speciation of selenium in garlic cultivated in soil amended with symbiotic fungi (mycorrhiza) and selenate. Anal Bioanal Chem 385: 1098-1108.
26. Lippman SM, Goodman PJ, Klein EA, Parnes HL, Thompson IM, Kristal AR, Santella RM, Probstfield JL, Moinpour CM, Albanes D, Taylor PR, Minasian LM, Hoque A, Thomas SM, Crowley JJ, Gaziano JM, Stanford JL, Cook ED, Fleshner NE, Lieber MM, Walther PJ, Khuri FR, Karp DD, Schwartz GG, Ford LG, Coltman CA (2005) Designing the Selenium and Vitamin E Cancer Prevention Trial (SELECT). J Natl Cancer Inst 97: 94-102.
27. Lippman SM, Klein EA, Goodman PJ, Lucia MS, Thompson IM, Ford LG, Parnes HL, Minasian LM, Gaziano JM, Hartline JA, Parsons JK, Bearden JD III, Crawford ED, Goodman GE, Claudio J, Winquist E, Cook ED, Karp DD, Walther P, Lieber MM, Kristal AR, Darke AK, Arnold KB, Ganz PA, Santella RM, Albanes D, Taylor PR, Probstfield JL, Jagpal TJ, Crowley JJ, Meyskens FL Jr, Baker LH, Coltman CA Jr (2009) Effect of selenium and vitamin E on risk of prostate cancer and other cancers: the Selenium and Vitamin E Cancer Prevention Trial (SELECT). JAMA 301: 39-51.
28. McSheehy S, Yang W, Pannier F, Szpunar J, Lobinski R, Auger J, Potin-Gautier M (2000) Speciation analysis of selenium in garlic by two-dimensional high-performance liquid chromatography with parallel inductively coupled plasma mass spectrometric and electrospray tandem mass spectrometric detection. Anal Chim Acta 421: 147-153.
29. McSheehy S, Kelly J, Tessier L, Mester Z (2005) Identification of selenomethionine in selenized yeast using two-dimensional liquid chromatography-mass spectrometry based proteomic analysis. Analyst 130: 35-37.
30. Mounicou S, Dernovics M, Bierla K, Szpunar J (2009) A sequential extraction procedure for an insight into selenium speciation in garlic. Talanta 77: 1877-1882.
31. Nigam SN, McConnell WB (1969) Seleno amino compounds from Astragalus bisulcatus isolation and identification of gamma-l-glutamyl-Se-methyl-seleno-l-cysteine and Se-methylseleno-l-cysteine. BBA - Gen Subj 192: 185-190.
32. Nigam SN, McConnell WB (1973) Biosynthesis of Se-methylselenocysteine in lima beans. Phytochemistry 12: 359-362.
33. Ogra Y (2008) Integrated strategies for identification of selenometabolites in animal and plant samples. Anal Bioanal Chem 390: 1685-1689.
34. Ogra Y, Anan Y (2009) Selenometabolomics: Identification of selenometabolites and specification of their biological significance by complementary use of elemental and molecular mass spectrometry. J Anal At Spectrom 24: 1477-1488.
35. Ohta Y, Suzuki N, Kobayashi Y, Hirano S (2011) Rapid speciation and quantification of selenium compounds by HPLC-ICP MS using multiple standards labelled with different isotopes. Isot Environ Health Stud 47: 330-340.
36. Padovese R, Kina SM, Barros RMC, Borelli P, Lanfer Marquez UM (2001) Biological importance of gamma-glutamyl-S-methylcysteine of kidney bean (Phaseolus vulgaris L.). Food Chem 73: 291-297.
37. Pedrero Z, Madrid Y (2009) Novel approaches for selenium speciation in foodstuffs and biological specimens: a review. Anal Chim Acta 634: 135-152.
38. Pedrero Z, Encinar JR, Madrid Y, Camara C (2007) Identification of selenium species in selenium-enriched Lens esculenta plants by using two-dimensional liquid chromatography-inductively coupled plasma mass spectrometry and [Se-77]selenomethionine selenium oxide spikes. J Chromatogr A 1139: 247-253.
39. Polatajko A, Banas B, Encinar JR, Szpunar J (2005) Investigation of the recovery of selenomethionine from selenized yeast by two-dimensional LC-ICP MS. Anal Bioanal Chem 381: 844-849.
40. Premarathna L, McLaughlin MJ, Kirby JK, Hettiarachchi GM, Stacey S, Chittleborough DJ (2012) Selenate-enriched urea granules are a highly effective fertilizer for selenium biofortification of paddy rice grain. J Agric Food Chem 60: 6037-6044.
41. Rayman MP, Infante HG, Sargent M (2008) Food-chain selenium and human health: spotlight on speciation. Br J Nutr 100: 238-253.
42. Smrkolj P, Germ M, Kreft I, Stibilj V (2006) Respiratory potential and Se compounds in pea (Pisum sativum L.) plants grown from Se-enriched seeds. J Exp Bot 57: 3595-3600.
43. Smrkolj P, Osvald M, Osvald J, Stibilj V (2007) Selenium uptake and species distribution in selenium-enriched bean (Phaseolus vulgaris L.) seeds obtained by two different cultivations. Eur Food Res Technol 225: 233-237.
44. Stan SD, Kar S, Stoner GD, Singh SV (2008) Bioactive food components and cancer risk reduction. J Cell Biochem 104: 339-356.
45. Szpunar J, Lobinski R (2002) Multidimensional approaches in biochemical speciation analysis. Anal Bioanal Chem 373: 404-411.
46. Taylor M, Chapman R, Beyaert R, Hernández-Sebastia C, Marsolais F (2008) Seed storage protein deficiency improves sulfur amino acid content in common bean (Phaseolus vulgaris L.): redirection of sulfur from gamma-glutamyl-S-methyl-cysteine. J Agric Food Chem 56: 5647-5654.
47. Thavarajah D, Vandenberg A, George GN, Pickering IJ (2007) Chemical form of selenium in naturally selenium-rich lentils (Lens culinaris L.) from Saskatchewan. J Agric Food Chem 55: 7337-7341.
48. Wu L, Guo X, Banuelos GS (1997) Accumulation of seleno-amino acids in legume and grass plant species grown in selenium-laden soils. Environ Toxicol Chem 16: 491-497.
49. Ximénez-Embún P, Alonso I, Madrid-Albarrán Y, Cámara C (2004) Establishment of selenium uptake and species distribution in lupine, Indian mustard, and sunflower plants. J Agric Food Chem 52: 832-838.
50. Yoshida M, Sugihara S, Inoue Y, Chihara Y, Kondo M, Miyamoto S, Sukcharoen B (2005) Composition of chemical species of selenium contained in selenium-enriched shiitake mushroom and vegetables determined by high performance liquid chromatography with inductively coupled plasma mass spectrometry. J Nutr Sci Vitaminol 51: 194-199.