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

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
• 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
• 3 Burg MB. Molecular basis of osmotic regulation. Am J Physiol 1995; 268: F983-F996
• 4 Caldas T, Demont-Caulet N, Ghazi A, Richarme G. Thermoprotection by glycine betaine and choline. Microbiology 1999; 145: 2543-2548
• 5 Zeisel SH, Blusztajn JK. Choline and human nutrition. Annu Rev Nutr 1994; 14: 269-296
• 6 Craig SAS. Betaine in human nutrition. Am J Clin Nutr 2004; 80: 539-549
• 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
• 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
• 9 Wald DS, Law M, Morris JK. Homocysteine and cardiovascular disease: evidence on causality from a meta-analysis. BMJ 2002; 325: 1202
• 10 Hankey GJ, Eikelboom JW. Homocysteine and stroke. Curr Opin Neurol 2001; 14: 95-102
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 21 Sakamoto A, Nishimura Y, Ono H, Sakura N. Betaine and homocysteine concentrations in foods. Pediatr Int 2002; 44: 409-413
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 32 Shahidi F. Nutraceuticals and functional foods: Whole versus processed foods. Trends Food Sci Technol 2009; 20: 376-387
• 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
• 34 Dawczynski C, Schubert R, Jahreis G. Amino acids, fatty acids, and dietary fibre in edible seaweed products. Food Chem 2007; 103: 891-899
• 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
• 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
• 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
• 38 Griffiths L. Assay by nuclear magnetic resonance spectroscopy: quantification limits. Analyst 1998; 123: 1061-1068
• 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
• 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
• 41 Kaufmann B, Christen P. Recent extraction techniques for natural products: microwave-assisted extraction and pressurised solvent extraction. Phytochem Anal 2002; 13: 105-113
• 42 Fan TWM. Metabolite profiling by one- and two-dimensional NMR analysis of complex mixtures. Prog Nucl Magn Reson Spectrosc 1996; 28: 161-219
• 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