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07-SEPTEMBER-2008 03:17:44 - Lignan Not to be confused with Lignin. The lignans are a group of chemical compounds found in plants, particularly in flax seed. Lignans are one of the major classes of phytoestrogens, which are estrogen-like chemicals and also act as antioxidants. The other classes of phytoestrogens are the isoflavones, and coumestans. Plant lignans are polyphenolic substances derived from phenylalanine via dimerization of substituted cinnamic alcohols see cinnamic acid, known as monolignols, to a dibenzylbutane skeleton 2. This reaction is catalysed by oxidative enzymes and is often controlled by dirigent proteins. Many natural products, known as phenylpropanoids, are built up of C6C3 units a propylbenzene skeleton 1 derived from cinnamyl units just as terpene chemistry builds on isoprene units. Structure 3 is a neolignan. Some examples of lignans are pinoresinol, podophyllotoxin, and steganacin. When part of the human diet, some lignans are metabolized to form mammalian lignans known as enterodiol 1 and enterolactone 2 by intestinal bacteria. Lignans that can be metabolized to form mammalian lignans are pinoresinol, lariciresinol, secoisolariciresinol, matairesinol, hydroxymatairesinol, syringaresinol and sesamin. Contents 1 Food sources 2 References 2.1 Footnotes 2.2 General references 3 External links Food sources Flax seed and sesame seed are among the highest known sources of lignans. The principal lignan precursor found in flaxseed is secoisolariciresinol diglucoside. Other sources of lignans include cereals rye, wheat, oat, barley, pumpkin seeds, soybeans, broccoli, beans, and some berries. Secoisolariciresinol and matairesinol were the first plant lignans identified in foods. Pinoresinol and lariciresinol are more recently identified plant lignans that contribute substantially to the total dietary lignan intakes. Typically, Lariciresinol and pinoresinol contribute about 75% to the total lignan intake whereas secoisolariciresinol and matairesinol contribute only about 25%.1 This distribution may change as the contributions of syringaresinol and hydroxymatairesinol have not properly been quantified in foods. Sources of lignans:2 Source Amount per 100 g Flaxseed 300,000 µg 0.3 g Sesame seed 29,000 µg 29 mg Brassica vegetables 185 - 2321 µg Grains 7-764 µg Red wine 91 µg Cola 0 A recent study3 shows the complexity of mammalian lignan precursors in the diet. In the table below are a few examples of the 22 analyzed species and the 24 lignans identified in this study. Mammalian lignan precursors as aglycones µg / 100 g. Major compounds in bold. Foodstuff Pinoresinol Syringaresinol Sesamin Lariciresinol Secoisolariciresinol Matairesinol Hydroxymatairesinol Flaxseed 871 48 not detected 1780 165759 529 35 Sesame seed 47136 205 62724 13060 240 1137 7209 Rye bran 1547 3540 not detected 1503 462 729 1017 Wheat bran 138 882 not detected 672 868 410 2787 Oat bran 567 297 not detected 766 90 440 712 Barley bran 71 140 not detected 133 42 42 541 References Footnotes ^ Linus Pauling Institute at Oregon State University ^ Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC 2005. Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br. J. Nutr. 93 3: 393-402. doi:10.1079/BJN20051371. PMID 15877880. ^ Smeds AI, et al. 2007. Quantification of a Broad Spectrum of Lignans in Cereals, Oilseeds, and Nuts. J.Agric. Food. Chem. 55: 1337-1346. doi:10.1021/jf0629134. PMID 17261017. General references IUPAC lignan nomenclature External links Lignan content in food Flax meal and oil and the prevention/treatment of cancer v d e Types of Phenylpropanoids Phenylpropanoids Cinnamic acids Cinnamaldehydes Monolignols Coumarins Flavonoids Stilbenoids Furanocoumarin Lignans Lignins Suberins Retrieved from http://en..org/wiki/Lignan Categories: Phytochemicals | Phenylpropanoids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Nederlands This page was last modified on 25 June 2008, at 06:31
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