Isolation and Characterization of the Lignans, Isolariciresinol and Pinoresinol, in Flaxseed Meal

The isolation and characterization of the lignans, isolariciresinol, pinoresinol, secoisolariciresinol, and matairesinol, potent phytoestrogens, from flaxseed meal are described. This is the first report of isolariciresinol and pinoresinol being detected in a food. The extraction method selected com...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1999-08, Vol.47 (8), p.3173-3180
Main Authors: Meagher, Lucy P, Beecher, Gary R, Flanagan, Vincent P, Li, Betty W
Format: Article
Language:English
Subjects:
acid hydrolysis
Agronomy. Soil science and plant productions
Biological and medical sciences
characterization
Chemical constitution
Chromatography, High Pressure Liquid
defatted flaxseed meal
Economic plant physiology
extraction
Flax - chemistry
Flour - analysis
Fundamental and applied biological sciences. Psychology
Furans - analysis
Furans - chemistry
Gas Chromatography-Mass Spectrometry
hydrolysis
isolation
lignans
Lignans - analysis
Lignans - chemistry
Lignin - analysis
Lignin - chemistry
linseed meal
Naphthols - analysis
Naphthols - chemistry
plant estrogens
Seeds - chemistry
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Summary:The isolation and characterization of the lignans, isolariciresinol, pinoresinol, secoisolariciresinol, and matairesinol, potent phytoestrogens, from flaxseed meal are described. This is the first report of isolariciresinol and pinoresinol being detected in a food. The extraction method selected combined the removal of the lignan glycosides from the plant matrix with an alcoholic solvent system, followed by acid hydrolysis to release the aglycons. A reversed-phase high-performance liquid chromatography with diode array detection system was used for initial separation and detection of the lignans at 280 nm in the acid-hydrolyzed methanolic extract. Lignan trimethylsilyl ether derivatives were characterized by gas chromatography/mass spectrometry. Secoisolariciresinol is the major lignan in flaxseed; isolariciresinol, pinoresinol, and matairesinol were identified as minor lignan components. Keywords: Phytoestrogens; lignans; isolariciresinol; pinoresinol; flaxseed; Linum usitatissimum; secoisolariciresinol; matairesinol
ISSN:0021-8561
1520-5118
DOI:10.1021/jf981359y