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Phenolic compounds in flaxseed

chromatographic and spectroscopic analyses of glucosidic conjugates

Johnsson, Pernilla (2004). Phenolic compounds in flaxseed. Uppsala : Sveriges lantbruksuniv. , Rapport / Sveriges lantbruksuniversitet, Institutionen för livsmedelsvetenskap, 1101-5411 ; 23
ISBN 91-576-6630-x
[Licentiate thesis]

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Abstract

The dietary lignan secoisolariciresinol diglucoside (SDG), present in high concentrations in flaxseed, and its metabolites enterolactone and enterodiol are thought to decrease the risk of hormone dependent cancers, cardiovascular disease and other “welfare” diseases. Flaxseed also contains other biologically active phenolic compounds, such as phenolic acids. The understanding of the nature of these compounds is crucial for their possible exploitation in drugs and functional foods. Until the mid 1990’s, the number of methods available for analysis of lignans and other compounds in flaxseed was limited and were divergent in terms of yields. Moreover, the structure of a “flaxseed polymer” to which these phenolic compounds are bound was not known. Thus, the aim of the work presented in this thesis was to develop a quantitative method for analysis of SDG in flaxseed and to unravel the structure of the “polymer”. A high performance liquid chromatography (HPLC) method for quantification of SDG in a base hydrolysed dioxane/ethanol flaxseed extract was developed. The method was applied to study the SDG content in 14 Swedish and 15 Danish flaxseed cultivars. The SDG content in defatted flour from the cultivars varied between 11.7 and 24.1 mg/g (6.1 – 13.3 mg/g in dried seeds). Two chromatographic peaks eluting before SDG in the developed HPLC system were identified as 4-O-β-D-glucopyranosyl-p-coumaric acid and 4-O-β-D-glucopyranosyl-ferulic acid by liquid chromatography-mass spectrometry and nuclear magnetic resonance (NMR) analyses. Moreover, by the use of different NMR techniques, a strait chain oligomeric structure with an average composition of five SDG residues interlinked with four 3-hydroxy-3-methyl glutaric acid residues was assigned to the “polymer”.

Authors/Creators:Johnsson, Pernilla
Title:Phenolic compounds in flaxseed
Subtitle:chromatographic and spectroscopic analyses of glucosidic conjugates
Year of publishing :June 2004
Volume:23
Number of Pages:36
Papers/manuscripts:
NumberReferences
ALLI. Johnsson, P., Kamal-Eldin, A., Lundgren, L.N., Åman, P. (2000). HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds. Journal of agricultural and food chemistry, 48:5216-5219. II. Johnsson, P., Peerlkamp, N., Kamal-Eldin, A., Andersson, R.E., Andersson, R., Lundgren, L.N., Åman, P. (2002). Polymeric fractions containing phenol glucosides in flaxseed, Food chemistry, 76:207-212. III. Kamal-Eldin, A., Peerlkamp, N., Johnsson, P., Andersson, R., Andersson, R.E., Lundgren, L.N., Åman, P. (2001). An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues, Phytochemistry, 58:587-590.
Place of Publication:Uppsala
ISBN for printed version:91-576-6630-x
ISSN:1101-5411
Language:English
Publication Type:Licentiate thesis
Full Text Status:Public
Agris subject categories.:Q Food science > Q04 Food composition
Subjects:Not in use, please see Agris categories
Agrovoc terms:linum usitatissimum, lignans, phenolic acids, polymers, glucosides, hplc, nmr spectroscopy
Keywords:Linum usitatissimum, lignans, phenolic acids, polymer, oligomer, complex, glucosides, HPLC, NMR
URN:NBN:urn:nbn:se:slu:epsilon-690
Permanent URL:
http://urn.kb.se/resolve?urn=urn:nbn:se:slu:epsilon-690
ID Code:570
Department:(NL, NJ) > Dept. of Food Science (until 161231)
Deposited By: Pernilla Johnsson
Deposited On:07 Jun 2004 00:00
Metadata Last Modified:02 Dec 2014 10:05

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