Secoisolariciresinol

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Secoisolariciresinol
Secoisolariciresinol Structural Formula V.1.svg
Names
IUPAC name
(8R,8′R)-3,3′-Dimethoxylignane-4,4′,9,9′-tetrol
Systematic IUPAC name
(2R,3R)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
Other names
(−)-Secoisolariciresinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.045.076 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 249-599-2
KEGG
PubChem CID
UNII
  • InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1 X mark.svgN
    Key: PUETUDUXMCLALY-HOTGVXAUSA-N X mark.svgN
  • COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O
Properties
C20H26O6
Molar mass 362.422 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with matairesinol has attracted much attention for its beneficial nutritional effects. [1]

Contents

Occurrence

The water extract of silver fir wood contains more than 5% of secoisolariciresinol. [2] It is also present in nettle brew. [3] Its content in flaxseed (Linum usitatıssimum) was found to be 0.3%, [4] which is the highest known content in food.

Biomedical aspects

In the intestine the gut microflora can form secoisolariciresinol from the secoisolariciresinol diglucoside and it can then be further transformed into the enterolignan enterodiol. Epidemiological studies showed associations between secoisolariciresinol intake and decreased risk of cardiovascular disease are promising, but they are yet not well established, perhaps due to low lignan intakes in habitual Western diets. At the higher doses used in intervention studies, associations were more evident. [5] [6]

Glycosides

Related Research Articles

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Tocopherols are a class of organic compounds comprising various methylated phenols, many of which have vitamin E activity. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was named tocopherol, from Greek τόκοςtókos 'birth' and φέρεινphérein 'to bear or carry', that is 'to carry a pregnancy', with the ending -ol signifying its status as a chemical alcohol.

α-Linolenic acid Chemical compound

α-Linolenic acid, also known as alpha-Linolenic acid (ALA), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched chain of carbon (C) atoms. Along the chain, some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). A double bond along the carbon chain can react with a pair of hydrogen atoms to change into a single -C-C- bond, with each H atom now bonded to one of the two C atoms. Glyceride fats without any carbon chain double bonds are called saturated because they are "saturated with" hydrogen atoms, having no double bonds available to react with more hydrogen.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

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<span class="mw-page-title-main">Secoisolariciresinol diglucoside</span> Antioxidant phytoestrogen

Secoisolariciresinol diglucoside (SDG) is an antioxidant phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed. It is a precursor of mammal lignans which are produced in the colon from chemicals in foods.

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The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores.

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<span class="mw-page-title-main">Matairesinol</span> Chemical compound

Matairesinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with secoisolariciresinol has attracted much attention for its beneficial nutritional effects.

<span class="mw-page-title-main">Lariciresinol</span> Chemical compound

Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora. Enterolignans are of interest because they are speculated to exhibit beneficial medicinal properties.

<span class="mw-page-title-main">Enterolactone</span> Chemical compound

Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

<span class="mw-page-title-main">Pinoresinol</span> Chemical compound

Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

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References

  1. Seibel, Wilfried; Kim Chung, Okkyung; Weipert, Dorian; Park, Seok-Ho (2006). "Cereals". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_093.pub2. ISBN   978-3527306732.
  2. Tavčar Benković, Eva; Žigon, Dušan; Mihailović, Vladimir; Petelinc, Tanja; Jamnik, Polona; Kreft, Samo (2017). "Identification, in vitro and in vivo Antioxidant Activity, and Gastrointestinal Stability of Lignans from Silver Fir (Abies alba) Wood Extract". Journal of Wood Chemistry and Technology. 37 (6): 467. doi:10.1080/02773813.2017.1340958. S2CID   90833072.
  3. Francišković, Marina; Gonzalez-Pérez, Raquel; Orčić, Dejan; Sánchez de Medina, Fermín; Martínez-Augustin, Olga; Svirčev, Emilija; Simin, Nataša; Mimica-Dukić, Neda (August 2017). "Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging Nettle) Extracts". Phytotherapy Research. 31 (8): 1183–1191. doi:10.1002/ptr.5836. ISSN   1099-1573. PMID   28544187. S2CID   33903986.
  4. Milder, Ivon E. J.; Arts, Ilja C. W.; Putte, Betty van de; Venema, Dini P.; Hollman, Peter C. H. (2005). "Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". British Journal of Nutrition. 93 (3): 393–402. doi: 10.1079/bjn20051371 . ISSN   1475-2662. PMID   15877880.
  5. Peterson, Julia; Dwyer, Johanna; Adlercreutz, Herman; Scalbert, Augustin; Jacques, Paul; McCullough, Marjorie L. (2010-10-01). "Dietary lignans: physiology and potential for cardiovascular disease risk reduction". Nutrition Reviews. 68 (10): 571–603. doi:10.1111/j.1753-4887.2010.00319.x. ISSN   0029-6643. PMC   2951311 . PMID   20883417.
  6. Pan, An; Yu, Danxia; Demark-Wahnefried, Wendy; Franco, Oscar H; Lin, Xu (2009-08-01). "Meta-analysis of the effects of flaxseed interventions on blood lipids". The American Journal of Clinical Nutrition. 90 (2): 288–297. doi:10.3945/ajcn.2009.27469. ISSN   0002-9165. PMC   3361740 . PMID   19515737.