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Secoisolariciresinol

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Secoisolariciresinol
Chemical structure of secoisolariciresinol
Names
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 Edit this at Wikidata
EC Number
  • 249-599-2
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
  • InChI=1/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
    Key: PUETUDUXMCLALY-HOTGVXAUBU
  • 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).
☒N verify (what is checkY☒N ?)

Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5%.[1] It is also present in nettle brew.[2] Its content in flaxseed (Linum usitatıssimum) was found to be 0.3%,[3] which is the highest known content in food.

In the intestine the gut microflora can form secoisolariciresinol from the secoisolariciresinol diglucoside and it can than 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.[4][5]

Glycosides

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.


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