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Secoisolariciresinol

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Secoisolariciresinol
Chemical structure of secoisolariciresinol
Chemical structure of secoisolariciresinol
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 InfoCard100.045.076Edit this at Wikidata
EC Number
  • 249-599-2
KEGG
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 ☒N
    Key: PUETUDUXMCLALY-HOTGVXAUSA-N ☒N
  • COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O
Properties
C20H26O6
Molar mass362.422 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Secoisolariciresinol is anorganic compound. It is classified as alignan, i.e., a type ofphenylpropanoid. It is present in some cereals, such asrye, and together withmatairesinol has attracted much attention for its beneficial nutritional effects.[1]

Occurrence

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

Biomedical aspects

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In the intestine the gut microflora can form secoisolariciresinol from thesecoisolariciresinol diglucoside and it can then be further transformed into theenterolignanenterodiol. Epidemiological studies showed associations between secoisolariciresinol intake and decreased risk ofcardiovascular 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

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References

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  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 3527306730.
  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.
Types oflignans
Lignans
Lignanglycosides
Mammalian lignans (enterolignans)
Neolignans
Flavonolignans
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