194
Views
6
CrossRef citations to date
0
Altmetric
LIQUID CHROMATOGRAPHY

High-Throughput Structural Elucidation of Lignans in Flaxseed by High-Performance Liquid Chromatography Coupled with Electrospray Ionization Mass Spectrometry

, &
Pages 556-567 | Received 03 Jul 2013, Accepted 05 Sep 2013, Published online: 03 Mar 2014

REFERENCES

  • Brooks , J. D. , W. E. Ward , J. E. Lewis , J. Hilditch , L. Nickell , E. Wong , and L. U. Thompson . 2004 . Supplementation with flaxseed alters estrogen metabolism in postmenopausal women to a greater extent than does supplementation with an equal amount of soy . Am. J. Clin. Nutr. 79 : 318 – 325 .
  • Chen J. , P. M. Stavro , and L. U. Thompson . 2002 . Dietary flaxseed inhibits human breast cancer growth and metastasis and downregulates expression of insulin-like growth factor and epidermal growth factor receptor . Nutr. Cancer. 43 : 417 – 423 .
  • Chung , Y. M. , H. C. Wang , M. EI-Shazly , Y. L. Leu , M. C. Cheng , C. L. Lee , F. R. Chang , and Y. C. Wu . 2011 . Antioxidant and tyrosinase inhibitory constituents from a desugared sugar cane extract, a byproduct of sugar production . J. Agric. Food Chem. 59 : 9219 – 9225 .
  • Eklund , P. C. , and O. K. Langvik . 2005 . Chemical studies on antioxidant mechanisms and free radical scavenging properties of lignans . Org. Biomol. Chem. 3 : 3336 – 3347 .
  • Fritsche J. , R. Angoelal , and M. Dachtler . 2002 . On-line liquid chromatography- nuclear magnetic resonance spectroscopy-mass spectrometry coupling for the separation and characterization of secoisolariciresinol diglucoside isomers in flaxseed . J. Chromatogr. A 972 : 195 – 203 .
  • Hanhineva K. , I. Rogachev , A. M. Aura , A. Aharoni , K. Poutanen , and H. Mykkänen . 2012. Identification of novel lignans in the whole grain rye bran by non-targeted LC–MS metabolite profiling Metabolomics . 8: 399–409.
  • Hutchins A. M. , M. C. Martini , B. A. Olson , W. Thomas , and J. L. Slavin . 2001 . Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women . Nutr. Cancer. 39 : 58 – 65 .
  • Jaroszewski J. W. 2005 . Hyphenated NMR methods in natural products research, part 1: Direct hyphenation Planta. Med. 71 : 691 – 700 .
  • Johnsson , P. , A. Kamal-Eldin , L. N. Lundgren , and P. Aman . 2000 . HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds . J Agric Food Chem. 48 : 5216 – 5219 .
  • Kim M. K. , B. C. Chung , V. Y. Yu , J. H. Nam , H. C. Lee , K. B. Huh , and S. K. Lim . 2002 . Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women . Clin. Endocrinol. (Oxf). 5 : 321 – 328 .
  • Liggins , J. , R. Grimwood , and S. A. Bingham . 2000 . Extraction and quantification of lignan phytoestrogens in food and human samples . Anal. Biochem. 287 : 102 – 109 .
  • Lucas E. A. , S. A. Lightfoot , L. J. Hammond , L. Devareddy , D. A. Khalil , and B. P. Daggy . 2004 . Flaxseed reduces plasma cholesterol and atherosclerotic lesion formation in ovariectomized Golden Syrian hamsters . Atherosclerosis. 173 : 223 – 229 .
  • Mabrok , H. B. , R. Klopfleisch , K. Z. Ghanem , T. Clavel , M. Blaut , and G. Loh . 2012 . Lignan transformation by gut bacteria lowers tumor burden in a gnotobiotic rat model of breast cancer Carcinogenesis 33 : 203 – 208 .
  • McCann M. J. , C. I. R. Gill , H. McGlynn , and I. R. Rowland . 2005 . Role of mammalian lignans in the prevention and treatment of prostate cancer . Nutr. Cancer. 52 : 1 – 14 .
  • Meagher , L. P. , G. R. Beecher , and V. P. Flanagan . 1999 . Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal . J. Agric. Food. Chem. 47 : 3173 – 3180 .
  • Ogborn M. R. , E. Nitschmann , H. Weiler , D. Leswick , and N. Bankovic-Calic . 1999 . Flaxseed ameliorates interstitial nephritis in rat polycystic kidney disease . Kidney Int. 55 : 417 – 423 .
  • Popova , I. E. , and C. Hall . 2009 . A. Kubátová Determination of lignans in flaxseed using liquid chromatography with time-of-flight mass spectrometry . J. Chromatogr. A. 1216 : 217 – 229 .
  • P Sainvitu , K. Nott , G. Richard , C. Blecker , C. Jérôme , J. P. Wathelet , M. Paquot , and M. Deleu . 2012 . Structure, properties and obtention routes of flaxseed lignan secoisolariciresinol: a review Biotechnol. Agron. Soc. Environ. 16 : 115 – 124 .
  • Sano T. , E. Oda , T. Yamashita , and H. Shiramasa . 2003 . Antithrombic and anti-atherogenic effects of partially defatted flaxseed meal using a laser-induced thrombosis test in apolipoprotein E and low-density lipoprotein receptor deficient mice . Blood Coagul. Fibrinolysis. 14 : 707 – 712 .
  • Shi , S. P. , D. Jiang , C. X. Dong , and P. F. Tua . 2006 . Lignans from the roots and rhizomes of clematis manshurica . Zeitschrift fuer Naturforschung, B: Chemical Sciences 61 : 1299 – 1303 .
  • Sicilia , T. , H. B. Niemeyer , D. M. Honig , and M. Metzler . 2003 . Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds . J. Agric. Food. Chem. 51 : 1181 – 1188 .
  • Silva F. G. D , Y. O'Callagahan , N. M. O'Brien , and F. M. Netto . 2013 . Antioxidant capacity of flaxseed products: The effect of in vitro digestion . Plant Food for Hum Nutr. 68 : 24 – 30 .
  • Struijs K. , J. P. Vincken , R. Verhoef , W. H. M. Van Oostveen-Van Casteren , A. G. J. Voragen , and H. Gruppen . 2007 . The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls . Phytochemistry 68 : 1227 – 1235 .
  • Truan , J. S. , J. M. Chen , and L. U. Thompson . 2012. Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice. Nutr Cancer. 64: 65–71.
  • Wang B. L. , J. P. Hu W. Tan L. Sheng H Chen , and Y. Li . 2008 . Simultaneous quantification of four active schisandra lignans from a traditional Chinese medicine Schisandra chinensis(Wuweizi) in rat plasma using liquid chromatography/mass spectrometry . J. Chromatogr. B. 865 : 114 – 120 .
  • Ward W. E. , Y. V. Yu , and A. M. Cheung . 2001 . Exposure to flaxseed and its purified lignan reduces bone strength in young but not older male rats . J. Toxicol. Env. Heal. A. 63 : 53 – 65 .
  • Willför , S. M. , A. I. Smedsb , and B. R. Holmbom . 2006 . Chromatographic analysis of lignans . J. Chromatogr. A. 1112 : 64 – 77 .
  • Wolfender J. L. , K. Ndjoko , and K. Hostettmann . 2001 . The potential of LC-NMR in phytochemical analysis . Phytochem. Anal. 12 : 1 – 25 .
  • Yang Y. L. , F. R. Chang , and Y. C. Wu . 2005 . Squadinorlignoside: A novel 7, 9'-dinorlignan from the stems of annona squamosa . Helv. Chim. Acta. 88 : 2731 – 2737 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.