Secoisolariciresinol: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 414643352

| ImageFile = Secoisolariciresinol Structural Formula V.1.svg

| IUPACName = (8''R'',8′''R'')-3,3′-Dimethoxylignane-4,4′,9,9′-tetrol

| SystematicName = (2''R'',3''R'')-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

| OtherNames = (−)-Secoisolariciresinol

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNoOther =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = M8QRJ7JEJH

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 65004

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 368347

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C18167

| EINECS = 249-599-2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 58845

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = PUETUDUXMCLALY-HOTGVXAUSA-N

|Section2={{Chembox Properties

| C=20 | H=26 | O=6

| MeltingPt =

| BoilingPt =

'''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.<ref>{{Ullmann|doi=10.1002/14356007.a06_093.pub2|title=Cereals|year=2006|last1=Seibel|first1=Wilfried|last2=Kim Chung|first2=Okkyung|last3=Weipert|first3=Dorian|last4=Park|first4=Seok-Ho|isbn=3527306730}}</ref>

==Occurrence==

The water extract of [[Abies alba|silver fir]] wood contains more than 5% of secoisolariciresinol.<ref name=Tavcar2017>{{cite journal | doi = 10.1080/02773813.2017.1340958| title = Identification, in vitro and in vivo Antioxidant Activity, and Gastrointestinal Stability of Lignans from Silver Fir (Abies alba) Wood Extract| journal = Journal of Wood Chemistry and Technology| volume = 37| issue = 6| pages = 467| year = 2017| last1 = Tavčar Benković| first1 = Eva| last2 = Žigon| first2 = Dušan| last3 = Mihailović| first3 = Vladimir| last4 = Petelinc| first4 = Tanja| last5 = Jamnik| first5 = Polona| last6 = Kreft| first6 = Samo| s2cid = 90833072}}</ref> It is also present in nettle brew.<ref>{{Cite journal|last1=Francišković|first1=Marina|last2=Gonzalez-Pérez|first2=Raquel|last3=Orčić|first3=Dejan|last4=Sánchez de Medina|first4=Fermín|last5=Martínez-Augustin|first5=Olga|last6=Svirčev|first6=Emilija|last7=Simin|first7=Nataša|last8=Mimica-Dukić|first8=Neda|date=August 2017|title=Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging Nettle) Extracts|journal=Phytotherapy Research|volume=31|issue=8|pages=1183–1191|doi=10.1002/ptr.5836|issn=1099-1573|pmid=28544187|s2cid=33903986}}</ref> Its content in [[flaxseed]] (Linum usitatissimum) was found to be 0.3%,<ref>{{Cite journal|last1=Milder|first1=Ivon E. J.|last2=Arts|first2=Ilja C. W.|last3=Putte|first3=Betty van de|last4=Venema|first4=Dini P.|last5=Hollman|first5=Peter C. H.|date=2005|title=Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol|journal=British Journal of Nutrition|language=en|volume=93|issue=3|pages=393–402|doi=10.1079/bjn20051371|issn=1475-2662|pmid=15877880|doi-access=free}}</ref> 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.<ref>{{Cite journal|last1=Peterson|first1=Julia|last2=Dwyer|first2=Johanna|last3=Adlercreutz|first3=Herman|last4=Scalbert|first4=Augustin|last5=Jacques|first5=Paul|last6=McCullough|first6=Marjorie L.|date=2010-10-01|title=Dietary lignans: physiology and potential for cardiovascular disease risk reduction|journal=Nutrition Reviews|language=en|volume=68|issue=10|pages=571–603|doi=10.1111/j.1753-4887.2010.00319.x|pmid=20883417|issn=0029-6643|pmc=2951311}}</ref><ref>{{Cite journal|last1=Pan|first1=An|last2=Yu|first2=Danxia|last3=Demark-Wahnefried|first3=Wendy|last4=Franco|first4=Oscar H|last5=Lin|first5=Xu|date=2009-08-01|title=Meta-analysis of the effects of flaxseed interventions on blood lipids|journal=The American Journal of Clinical Nutrition|language=en|volume=90|issue=2|pages=288–297|doi=10.3945/ajcn.2009.27469|pmid=19515737|issn=0002-9165|pmc=3361740}}</ref>

[[Category:Lignans]]

[[Category:Primary alcohols]]

{{phenol-stub}}