Download PDF
Planta Med 2015; 81(08): 679-684
DOI: 10.1055/s-0035-1546018
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Cardioprotective Potential of Irish Macroalgae: Generation of Glycine Betaine and Dimethylsulfoniopropionate Containing Extracts by Accelerated Solvent Extraction

Juan Valverde
1   Food Biosciences Department, Teagasc Food Research Centre, Ashtown, D15, Dublin, Ireland
,
Maria Hayes
1   Food Biosciences Department, Teagasc Food Research Centre, Ashtown, D15, Dublin, Ireland
,
Pádraig McLoughlin
1   Food Biosciences Department, Teagasc Food Research Centre, Ashtown, D15, Dublin, Ireland
,
Dilip K. Rai
1   Food Biosciences Department, Teagasc Food Research Centre, Ashtown, D15, Dublin, Ireland
,
Anna Soler-Vila
2   Irish Seaweed Research Group, Ryan Institute, Environmental, Marine and Energy Research, National University of Ireland, Galway, Ireland
› Author Affiliations
Further Information

Publication History

received 21 July 2014
revised 30 March 2015

accepted 07 April 2015

Publication Date:
27 May 2015 (online)

    Permissions and Reprints

Abstract

Accelerated solvent extraction (ASE®) was used to generate 18 macroalgal extracts from Irish seaweeds. The glycine betaine and dimethylsulfoniopriopionate content of the generated ASE® extracts were estimated using 1H-NMR and confirmed for selected extracts using ultra performance liquid chromatography and mass spectrometry. Dimethylsulfoniopriopionate was only identified in the ASE® extract generated from Codium fragile ISCG0029. Glycine betaine was identified in the ASE® extract generated from Ulva intestinalis ISCG0356 using 1H-NMR. Mass spectrometry analysis found that the seaweed species Cytoseira nodicaulis ISCG0070, Cytoseira tamariscofolia ISCG0283, and Polysiphonia lanosa ISCG0462 also had a glycine betaine content that ranged from 1.39 ng/ml to 105.11 ng/ml. Generated ASE® macroalgal extracts have potential for use as functional food ingredients in food products.

Key words

macroalgae - tertiary sulfonium compounds - glycine betaine - dimethylsulfoniopriopionate (DMSP) - pressurised liquid extraction (PLE) - quantitative 1H-NMR and mass spectrometry
 

  • References

  • 1 de Zwart FJ, Slow S, Payne RJ, Lever M, George PM, Gerrard JA, Chambers ST. Glycine betaine and glycine betaine analogues in common foods. Food Chem 2003; 83: 197-204
    CrossrefPubMedGoogle Scholar
  • 2 Zeisel SH, Mar MH, Howe JC, Holden JM. Concentrations of choline-containing compounds and betaine in common foods. J Nutr 2003; 133: 1302-1307
    PubMedGoogle Scholar
  • 3 Burg MB. Molecular basis of osmotic regulation. Am J Physiol 1995; 268: F983-F996
    PubMedGoogle Scholar
  • 4 Caldas T, Demont-Caulet N, Ghazi A, Richarme G. Thermoprotection by glycine betaine and choline. Microbiology 1999; 145: 2543-2548
    CrossrefPubMedGoogle Scholar
  • 5 Zeisel SH, Blusztajn JK. Choline and human nutrition. Annu Rev Nutr 1994; 14: 269-296
    CrossrefPubMedGoogle Scholar
  • 6 Craig SAS. Betaine in human nutrition. Am J Clin Nutr 2004; 80: 539-549
    Google Scholar
  • 7 European Food Safety Authority, Panel on Dietetic Products. Scientific opinion on the substantiation of health claims related to betaine and contribution to normal homocysteine metabolism (ID 4325) pursuant to Article 13(1) of Regulation (EC) No 1924/2006. EFSA J 2011; 9: 2052
    PubMedGoogle Scholar
  • 8 Schwab U, Törrönen A, Toppinen L, Alfthan G, Saarinen M, Aro A, Uusitupa M. Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects. Am J Clin Nutr 2002; 76: 961-967
    PubMedGoogle Scholar
  • 9 Wald DS, Law M, Morris JK. Homocysteine and cardiovascular disease: evidence on causality from a meta-analysis. BMJ 2002; 325: 1202
    CrossrefPubMedGoogle Scholar
  • 10 Hankey GJ, Eikelboom JW. Homocysteine and stroke. Curr Opin Neurol 2001; 14: 95-102
    CrossrefPubMedGoogle Scholar
  • 11 Slow S, Lever M, Lee MB, George PM, Chambers ST. Betaine analogues alter homocysteine metabolism in rats. Int J Biochem Cell Biol 2004; 36: 870-880
    CrossrefPubMedGoogle Scholar
  • 12 Nakajima K. Hyperhomocyteinemia can be ameliorated by dimethylsulfoniopropionate in place of folic acid in mice. J Nutr Sci Vitaminol (Tokyo) 2006; 52: 61-65
    CrossrefPubMedGoogle Scholar
  • 13 Lee MB, Blunt JW, Lever M, George PMA. Nuclear-magnetic-resonance-based assay for betaine-homocysteine methyltransferase activity. Anal Biochem 2004; 330: 199-205
    CrossrefPubMedGoogle Scholar
  • 14 Minematsu M, Nakajima K. Significant effect of dimethylsulfoniopropionate on Parkinsonʼs disease of senescence-accelerated mice induced by 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine. J Nutr Sci Vitaminol (Tokyo) 2008; 54: 335-338
    CrossrefPubMedGoogle Scholar
  • 15 Nakajima K, Minematsu M. Ameliorating effect of dimethylsulfoniopropionate on the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Parkinsonʼs disease of mice. J Nutr Sci Vitaminol (Tokyo) 2006; 52: 70-74
    CrossrefPubMedGoogle Scholar
  • 16 Nakajima K, Yokoyama A, Minematsu M. Anticancer effects of a tertiary sufonium compounds, dimethylsulfoniopropionate, in green sea algae on Ehrlich ascites carcinoma-bearing mice. J Nutr Sci Vitaminol (Tokyo) 2009; 55: 434-438
    CrossrefPubMedGoogle Scholar
  • 17 Blunden G, Smith BE, Irons MW, Yang MH, Roch OG, Patel AV. Betaines and tertiary sulphonium compounds from 62 species of marine algae. Biochem Syst Ecol 1992; 20: 373-388
    CrossrefPubMedGoogle Scholar
  • 18 Al Amoudi OA, Ali AY, Blunden G, Smith BE. Betaines and tertiary sulphonium compounds from Saudi Arabian marine algae. Br Phycol J 1988; 23: 399-402
    CrossrefPubMedGoogle Scholar
  • 19 Blunden G, Gordon SM, Smith BE, Fletcher RL. Quaternary ammonium compounds in species of the Fucaceae (Phaeophyceae) from Britain. Br Phycol J 1985; 20: 105-108
    CrossrefPubMedGoogle Scholar
  • 20 Slow S, Donaggio M, Cressey PJ, Lever M, George PM, Chambers ST. The betaine content of New Zealand foods and estimated intake in the New Zealand diet. J Food Comp Anal 2005; 18: 473-485
    CrossrefPubMedGoogle Scholar
  • 21 Sakamoto A, Nishimura Y, Ono H, Sakura N. Betaine and homocysteine concentrations in foods. Pediatr Int 2002; 44: 409-413
    CrossrefPubMedGoogle Scholar
  • 22 Chudek JA, Foster R, Moore DJ, Reed RH. Identification and quantification of methylated osmolytes in algae using proton nuclear magnetic resonance spectroscopy. Br Phycol J 1987; 22: 169-173
    CrossrefPubMedGoogle Scholar
  • 23 Mendiola JA, Herrero M, Cifuentes A, Ibañez E. Use of compressed fluids for sample preparation: food applications. J Chromatogr A 2007; 1152: 234-246
    CrossrefPubMedGoogle Scholar
  • 24 Ibanez E, Herrero M, Mendiola JA, Castro-Puyana M. Extraction and characterization of bioactive compounds with health benefits from marine resources: macro and micro algae, cyanobacteria and invertebrates. In: Hayes M, editor Marine bioactive compounds. Heidelberg: Springer; 2012: 55-98
    CrossrefGoogle Scholar
  • 25 Moreda-Piñeiro J, Alonso-Rodríguez E, López-Mahía P, Muniategui-Lorenzo S, Prada-Rodríguez D, Moreda-Piñeiro A, Bermejo-Barrera P. Development of a new sample pre-treatment procedure based on pressurized liquid extraction for the determination of metals in edible seaweed. Anal Chim Acta 2007; 598: 95-102
    CrossrefPubMedGoogle Scholar
  • 26 Shang YF, Kim SM, Lee WJ, Um BH. Pressurized liquid method for fucoxanthin extraction from Eisenia bicyclis (Kjellman) Setchell. J Biosci Bioeng 2011; 111: 237-241
    CrossrefPubMedGoogle Scholar
  • 27 Onofrejová L, Vašíčková J, Klejdus B, Stratil P, Mišurcová L, Kráčmar S, Kopecký J, Vacek J. Bioactive phenols in algae: the application of pressurized-liquid and solid-phase extraction techniques. J Pharm Biomed Anal 2010; 51: 464-470
    CrossrefPubMedGoogle Scholar
  • 28 Alonso-Salces RM, Korta E, Barranco A, Berrueta LA, Gallo B, Vicente F. Determination of polyphenolic profiles of Basque cider apple varieties using accelerated solvent extraction. J Agric Food Chem 2001; 49: 3761-3767
    CrossrefPubMedGoogle Scholar
  • 29 Han Z, Ren Y, Zhu J, Cai Z, Chen Y, Luan L, Wu Y. Multianalysis of 35 mycotoxins in traditional Chinese medicines by ultra-high-performance liquid chromatography-tandem mass spectrometry coupled with accelerated solvent extraction. J Agric Food Chem 2012; 60: 8233-8247
    CrossrefPubMedGoogle Scholar
  • 30 Holt MD, Moreau RA, DerMarderosian A, McKeown N, Jacques PF. Accelerated solvent extraction of alkylresorcinols in food products containing uncooked and cooked wheat. J Agric Food Chem 2012; 60: 4799-4802
    CrossrefPubMedGoogle Scholar
  • 31 Klein AP, Beach ES, Emerson JW, Zimmerman JB. Accelerated solvent extraction of lignin from Aleurites moluccana (Candlenut) nutshells. J Agric Food Chem 2010; 58: 10045-10048
    CrossrefPubMedGoogle Scholar
  • 32 Shahidi F. Nutraceuticals and functional foods: Whole versus processed foods. Trends Food Sci Technol 2009; 20: 376-387
    CrossrefPubMedGoogle Scholar
  • 33 Sánchez-Machado DI, López-Cervantes J, López-Hernández J, Paseiro-Losada P. Fatty acids, total lipid, protein and ash contents of processed edible seaweeds. Food Chem 2004; 85: 439-444
    CrossrefPubMedGoogle Scholar
  • 34 Dawczynski C, Schubert R, Jahreis G. Amino acids, fatty acids, and dietary fibre in edible seaweed products. Food Chem 2007; 103: 891-899
    CrossrefPubMedGoogle Scholar
  • 35 Gómez-Ordóñez E, Jiménez-Escrig A, Rupérez P. Dietary fibre and physicochemical properties of several edible seaweeds from the northwestern Spanish coast. Food Res Int 2010; 43: 2289-2294
    CrossrefPubMedGoogle Scholar
  • 36 Mohn T, Cutting B, Ernst B, Hamburger M. Extraction and analysis of intact glucosinolates – a validated pressurized liquid extraction/liquid chromatography-mass spectrometry protocol for Isatis tinctoria, and qualitative analysis of other cruciferous plants. J Chromatogr A 2007; 1166: 142-151
    CrossrefPubMedGoogle Scholar
  • 37 Cobas JC, Bernstein MA, Martín-Pastor M, Tahoces PGA. A new general-purpose fully automatic baseline-correction procedure for 1D and 2D NMR data. J Magn Reson 2006; 183: 145-151
    CrossrefPubMedGoogle Scholar
  • 38 Griffiths L. Assay by nuclear magnetic resonance spectroscopy: quantification limits. Analyst 1998; 123: 1061-1068
    CrossrefPubMedGoogle Scholar
  • 39 Maniara G, Rajamoorthi K, Rajan S, Stockton GW. Method performance and validation for quantitative analysis by (1)h and (31)p NMR spectroscopy. Applications to analytical standards and agricultural chemicals. Anal Chem 1998; 70: 4921-4928
    CrossrefPubMedGoogle Scholar
  • 40 Rai DK, Brunton NP, Koidis A, Rawson A, McLoughlin P, Griffiths WJ. Characterisation of polyacetylenes isolated from carrot (Ducus caroba) extracts by negative ion tandem mass spectrometry. Rapid Commun Mass Spectrom 2011; 15: 2231-2239
    PubMedGoogle Scholar
  • 41 Kaufmann B, Christen P. Recent extraction techniques for natural products: microwave-assisted extraction and pressurised solvent extraction. Phytochem Anal 2002; 13: 105-113
    CrossrefPubMedGoogle Scholar
  • 42 Fan TWM. Metabolite profiling by one- and two-dimensional NMR analysis of complex mixtures. Prog Nucl Magn Reson Spectrosc 1996; 28: 161-219
    CrossrefPubMedGoogle Scholar
  • 43 Boroujerdi AB, Lee P, DiTullio G, Janech M, Vied S, Bearden D. Identification of isethionic acid and other small molecule metabolites of Fragilariopsis cylindrus with nuclear magnetic resonance. Anal Bioanal Chem 2012; 404: 777-784
    CrossrefPubMedGoogle Scholar