SE-HPLC-DAD Analysis of Flaxseed Lignan Macromolecule and its Hydrolysates

Open access

SE-HPLC-DAD Analysis of Flaxseed Lignan Macromolecule and its Hydrolysates

A lignan macromolecule (LM) was extracted from defatted flaxseeds using an ethanol-dioxan system (1:1, v/v) and purified using Amberlite column chromatography with water and methanol as mobile phases. The LM was subjected to chemical hydrolysis (base, acid, base & acid), as well as to enzymatic processing using pepsin, pancreatin, cellulase, and β-glucuronidase.

The study revealed that lignan macromolecule in flaxseed was not homogenous. The chemical hydrolysis as well as enzymatic treatment using β-glucuronidase and cellulase released low molecular phenolic compounds from the lignan macromolecule. The liberation of secoisolariciresinol (SECO) and free phenolic acids (p-coumaric and ferulic acids) from flaxseed lignan macromolecule as a result of the base and acid hydrolyses was noted. The application of pepsin and pancreatin did not change the composition of the lignan macromolecule.

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • Adlercreutz H. Phytoestrogens and cancer. Lancet Oncol. 2002 3 364-373.

  • Åkerberg A. K. E. Liljeberg H. G. M. Granfeldt Y. E. Drews A. W. Björck I. M. E. An in vitro method based on chewing to predict resistant starch content in foods allows parallel determination of potentially available starch and dietary fiber. J. Nutr. 1998 128 651-660.

  • Amarowicz R. Wanasundara U. Wanasundara J. Shahid F. Antioxidant activity of ethanolic extracts of flaxseed in a β-carotene-linoleate model system. J. Food Lipids 1993 1 111-117.

  • Amarowicz R. Wanasundara P. K. J. P. D. Shahidi F. Chromatographic separation of flaxseed phenolics. Nahrung 1994 520-526.

  • Amarowicz R. Karamać M. Wanasundara J. P. D. Shahidi F. Antioxidant activity of hydrophobic fractions of flaxseed. Nahrung 1997 41 178-180.

  • Amarowicz R. Pegg R. P. Kosińska A. SE-HPLC separation of myosin complex with tannins of bearberry (Arctostaphylos uvaursi L. Sprengel) leaves. Czech J. Food Sci. 2009 27 386-391.

  • Boccardo F. Lunardi G. Guglielmini P. Parodi M. Murialdo R. Schettini G. Rubagotti A. Serum enterolactone levels and the risk of breast cancer in woman with palpable cysts. Eur. J. Cancer 2004 40 84-89.

  • Borriello S. P. Setchell K. D. Axelson M. Lawson A. M. Production and metabolism of lignans by the human faceal flora. J. Appl. Bacteriol. 1985 58 37-43.

  • Eldin-Kamal A. Peerlkamp N. Johnsson P. Andersson R. Andersson R. E. Lundgren L. N. Åman P. An oligomer from flaxseed composed of secoisolariciresinol diglucoside and 3-hydroxy-3-methyl glutaric acid residues. Phytochemistry 2001 58 587-590.

  • Hosseinian F. S. Muir A. D. Westcott N. D. Krol E. S. Antioxidant capacity of flaxseed lignans in two model systems. J. Am. Oil Chem. Soc. 2006 83 835-840.

  • Hu C. Yuan Y. V. Kitts D. D. Antioxidant activities of the flaxseed lignin secoisolariciresinol diglucoside its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro. Food Chem. Toxicol. 2007 45 2219-2227.

  • Jenab M. Thompson L. U. The influence of flaxseed and lignans on colon carcinogenesis and β-glucuronidase activity. Carcinogenesis 1996 17 1343-1348.

  • Johnsson P. Kamal-Eldin A. Lundgren L. N. Åman P. HPLC method for analysis of se- coisolariciresinol diglucoside in flaxseeds. J. Agric. Food Chem. 2000 48 5216-5219.

  • Johnsson P. Peerlkamp N. Kamal-Eldin A. Andersson R. E. Andersson R. Lundgren L. N. Åman P. Polymeric fractions containing phenol glucosides in flaxseed. Food Chem. 2002 76 207-212.

  • Karamać M. Kosińska A. Rybarczyk A. Pegg R. B. Chromatographic separation of phenolic compounds from rapeseed by SEHPLC - a short report. Pol. J. Food Nutr. Sci. 2007 57 87-90.

  • Krajčová A. Schulzová V. Hajšlová J. Bjelková M. Lignans in flaxseed. Czech J. Food Sci. 2009 27 S252-S255.

  • Kraushofer T. Sontag G. Determination of some phenolic compounds in flax seed and nettle roots by HPLC with coulomertic electrode array detection. Eur. Food Res. Technol. 2002 215 529-533.

  • Lainé E. Hano C. Lamblin C. Lignans. 2009 in: Chemoprevention of Cancer and DNA Damage by Dietary Factors (eds. S. Knasmüller D. M. DeMarini I. Johnson C. Gerhäuser). Willey-VCH Editions Berlin pp. 555-577.

  • Lin X. Gingrich J. R. Bao W. Li J. Haroon Z. A. Demark-Wahnefried W. Effect of flaxseed supplementation on prostatic carcinoma in transgenic mice. Urology 2002 60 919-924.

  • Lorenc-Kukuła K. Amarowicz R. Oszmiański J. Dermann P. Starzycki M. Skała J. Żuk M. Kulma A. Szopa J. Pleiotropic effect of phenolic compounds content increases in transgenic flax plant. J. Agric. Food Chem. 2005 53 3685-3692.

  • Lorenc-Kukuła K. Kosińska A. Szopa J. Amarowicz R. RP-HPLC-DAD finger print analysis of phenolic extracts from transgenic flax. Pol. J. Food Nutr. Sci. 2009 59 135-140.

  • Mazur W. Fotsis T. Wahala K. Ojala S. Salakka A. Adlercreutz H. Isotope dilution gas chromatographic - mass spectrometric method for the determination of isoflavonoids coumestrol and lignans in food. Anal. Biochem. 1996 233 169-180.

  • Meagher L. P. Beecher G. R. Flanagan V. P. Li W. Isolation and characterization of lignans isolariresinol and pinoresinol in flaxseed meal. J. Agric. Food Chem. 1999 47 3173-3180.

  • Milder I. E. Arts L. C. Venema D. P. Lasaroms J. J. P. Wahala K. Hollman P. C. H. Optimization of liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol materesinol lariciresinol and pinoresinol in foods. J. Agric. Food Chem. 2004 52 4643-4651.

  • Nesbitt P. Thompson L. Human metabolizm of mammalian lignans precursors in raw and processed flaxseed. Am. J. Clin. Nutr. 1999 69 549-555.

  • Niemeyer H. B. Metzler M. Differences in the antioxidant activity of plant and mammalian lignans. J. Food Engin. 2003 56 255-256.

  • Obermeyer W. R. Musser S. M. Betz J. M. Casey R. E. Pohland A. E. Page S. W. Chemical studies of phytoestrogens and related compounds in dietary supplements: flax and chaparral. Proc. Soc. Exp. Biol. Med. 1995 208 6-12.

  • Pegg R. B. Rybarczyk A. Amarowicz R. Chromatographic separation of tannin fractions from a bearberry-leaf (Arctostaphylos uva-ursi L. Sprengel) extract by SE-HPLC - a short report. Pol. J. Food Nutr. Sci. 2008 58 485-490.

  • Renouard S. Hano C. Corbin C. Fliniaux O. Lopez T. Montguillon J. Barakzoy E. Mesnard F. Lamblin F. Lainé E. Cellulase-assisted release of secoisolariciresinol from extracts of flax (Linum usitatissimum) hulls and whole seeds. Food Chem. 2010 122 679-687.

  • Srivastava A. Greenspan P. Hartle D. K. James L. Hargrove J. L. Amarowicz R. Pegg R. B. Antioxidant and anti-inflammatory activities of polyphenolics from southeastern U. S. range blackberry cultivars. J. Agric. Food Chem. 2010 58 6102-6109.

  • Struijs K. Vincken J.-P. Verhoef R. Voragen A. G. J. Gruppen H. Hydroxycinnamic acids are ester-linked directly to glucosyl moieties within the lignan macromolecule from flaxseed hulls. Phytochemistry 2008 69 1250-1260.

  • Struijs K. Vincken J.-P. Doeswijk T. G. Voragen A. G. J. Gruppen H. The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid and glucosides and ferulic acid glucosides. Phytochemistry 2009 70 262-269.

Journal information
Impact Factor

IMPACT FACTOR 2017: 1.697
5-year IMPACT FACTOR: 1.760

CiteScore 2018: 1.92

SCImago Journal Rank (SJR) 2018: 0.621
Source Normalized Impact per Paper (SNIP) 2018: 0.908

All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 207 70 1
PDF Downloads 108 40 1