Secoisolariciresinol

Structural formula
General
Surname	Secoisolariciresinol
other names	(-) - Secoisolariciresinol; (2 R , 3 R ) -2,3-bis [(4-hydroxy-3-methoxyphenyl) methyl] butane-1,4-diol ( IUPAC );
Molecular formula	C 20 H 26 O 6
External identifiers / databases
EC number	249-599-2
ECHA InfoCard	100.045.076
PubChem	65373
ChemSpider	58845
DrugBank	DB12179
Wikidata	Q4413253
properties
Molar mass	362.42 g mol −1
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Secoisolariciresinol is a lignan , a type of phenylpropanoid .

Occurrence and extraction

Silver fir ( Abies alba ) - wood contains secoisolariciresinol.

A water extract from silver fir wood contains it in a concentration of more than 5%. In the food sector , the highest concentration (0.3%) was found in flaxseed ( Linum usitatissimum ). Nettle tea is another example of a food that contains secoisolariciresinol.

Education and Impact

In the inner intestinal microflora Secoisolariciresinol may be made of the diglucoside are formed, which in the Enterolignan enterodiol can be converted. Epidemiological studies show a promising association between the intake of secoisolariciresinol and a reduced risk of cardiovascular diseases . The connection is probably difficult to establish due to the low intake of lignan and the usual Western diet. The association was more pronounced at higher doses used in intervention studies.

Individual evidence

↑ ^a ^b Data sheet Secoisolariciresinol, ≥95.0% (HPLC) from Sigma-Aldrich , accessed on July 4, 2018 ( PDF ).
↑ Eva Tavčar Benković, Dušan Žigon, Vladimir Mihailović, Tanja Petelinc, Polona Jamnik, Samo Kreft: Identification, in vitro and in vivo Antioxidant Activity, and Gastrointestinal Stability of Lignans from Silver Fir (Abies alba) Wood Extract . In: Journal of Wood Chemistry and Technology . tape 37 , no. 6 , 2017, p. 467 , doi : 10.1080 / 02773813.2017.1340958 .
^ Ivon EJ Milder, Ilja CW Arts, Betty van de Putte, Dini P. Venema, Peter CH Hollman: Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol . In: British Journal of Nutrition . tape 93 , no. 3 , March 1, 2005, p. 393-402 , doi : 10.1079 / bjn20051371 .
↑ Marina Francišković, Raquel Gonzalez-Pérez, Dejan Orčić, Fermín Sánchez de Medina, Olga Martínez-Augustin, Emilija Svirčev, Nataša Simin, Neda Mimica-Dukić: Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging. Nettle) Extracts. Nettle) . In: Phytotherapy Research . tape 31 , no. 8 , May 24, 2017, p. 1183-1191 , doi : 10.1002 / ptr.5836 , PMID 28544187 .
↑ Julia Peterson, Johanna Dwyer, Herman Adlercreutz, Augustin Scalbert, Paul Jacques, Marjorie L. McCullough: Dietary lignans: physiology and potential for cardiovascular disease risk reduction . In: Nutrition Reviews . tape 68 , no. 10 , October 1, 2010, p. 571–603 , doi : 10.1111 / j.1753-4887.2010.00319.x , PMC 2951311 (free full text).
↑ To Pan, Danxia Yu, Wendy Demark-Wahnefried, Oscar H Franco, Xu Lin: Meta-analysis of the effects of flaxseed interventions on blood lipids . In: The American Journal of Clinical Nutrition . tape 90 , no. 2 , August 1, 2009, p. 288–297 , doi : 10.3945 / ajcn.2009.27469 , PMC 3361740 (free full text).

[Sigma-1] Data sheet Secoisolariciresinol, ≥95.0% (HPLC) from Sigma-Aldrich , accessed on July 4, 2018 ( PDF ).

[Tavcar2017-2] Eva Tavčar Benković, Dušan Žigon, Vladimir Mihailović, Tanja Petelinc, Polona Jamnik, Samo Kreft: Identification, in vitro and in vivo Antioxidant Activity, and Gastrointestinal Stability of Lignans from Silver Fir (Abies alba) Wood Extract . In: Journal of Wood Chemistry and Technology . tape 37 , no. 6 , 2017, p. 467 , doi : 10.1080 / 02773813.2017.1340958 .

[3] Ivon EJ Milder, Ilja CW Arts, Betty van de Putte, Dini P. Venema, Peter CH Hollman: Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol . In: British Journal of Nutrition . tape 93 , no. 3 , March 1, 2005, p. 393-402 , doi : 10.1079 / bjn20051371 .

[4] Marina Francišković, Raquel Gonzalez-Pérez, Dejan Orčić, Fermín Sánchez de Medina, Olga Martínez-Augustin, Emilija Svirčev, Nataša Simin, Neda Mimica-Dukić: Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging. Nettle) Extracts. Nettle) . In: Phytotherapy Research . tape 31 , no. 8 , May 24, 2017, p. 1183-1191 , doi : 10.1002 / ptr.5836 , PMID 28544187 .

[5] Julia Peterson, Johanna Dwyer, Herman Adlercreutz, Augustin Scalbert, Paul Jacques, Marjorie L. McCullough: Dietary lignans: physiology and potential for cardiovascular disease risk reduction . In: Nutrition Reviews . tape 68 , no. 10 , October 1, 2010, p. 571–603 , doi : 10.1111 / j.1753-4887.2010.00319.x , PMC 2951311 (free full text).

[6] To Pan, Danxia Yu, Wendy Demark-Wahnefried, Oscar H Franco, Xu Lin: Meta-analysis of the effects of flaxseed interventions on blood lipids . In: The American Journal of Clinical Nutrition . tape 90 , no. 2 , August 1, 2009, p. 288–297 , doi : 10.3945 / ajcn.2009.27469 , PMC 3361740 (free full text).