Matairesinol

Matairesinol[1]
Chemical structure of matairesinol
Names
IUPAC name
(8β,8′α)-4,4′-Dihydroxy-3,3′-dimethoxylignano-9,9′-lactone
Systematic IUPAC name
(3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Other names
(αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1 checkY
    Key: MATGKVZWFZHCLI-LSDHHAIUSA-N checkY
  • InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
    Key: MATGKVZWFZHCLI-LSDHHAIUBP
  • Key: MATGKVZWFZHCLI-LSDHHAIUSA-N
  • O=C2OC[C@H](Cc1cc(OC)c(O)cc1)[C@H]2Cc3ccc(O)c(OC)c3
Properties
C20H22O6
Molar mass 358.390 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 ?)

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.[which?][2]

Metabolism

The plant lignans are precursors of the enterolignans (mammalian lignans).[3] A number of plant lignans are metabolized to the enterolignans (enterodiol and enterolactone) that can potentially reduce the risk of certain cancers and cardiovascular diseases.[4]

Biomedical considerations

Although some studies attribute disease preventative (cardio-protective and hormone associated cancers like breast cancer) benefits of lignans, the results are inconclusive.[5] Matairesinol has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).[6]

References

  1. ^ Matairesinol at Sigma-Aldrich
  2. ^ 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.
  3. ^ Niemeyer HB, Honig DM, Kulling SE, Metzler M (October 2003). "Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol". J. Agric. Food Chem. 51 (21): 6317–25. doi:10.1021/jf030263n. PMID 14518962.
  4. ^ Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC (March 2005). "Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". Br. J. Nutr. 93 (3): 393–402. doi:10.1079/BJN20051371. PMID 15877880.
  5. ^ Linus Pauling Institute at Oregon State University
  6. ^ Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE. 8 (5): e63354. Bibcode:2013PLoSO...863354S. doi:10.1371/journal.pone.0063354. PMC 3653934. PMID 23691032.