Matairesinol

Matairesinol[1]
Names
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
580-72-3 N=
3D model (Jmol) Interactive image
ChEBI CHEBI:6698 N
ChEMBL ChEMBL425148 YesY
ChemSpider 106491 YesY
DrugBank DB04200 YesY
PubChem 119205
Properties
C20H22O6
Molar mass 358.39 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 YesYN ?)
Infobox references

Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits.[2]

The plant lignans are precursors of the enterolignans (mammalian lignans). 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.[3]

Although there are studies which indicate the disease prevention (cardio-protective and hormone associated cancers like breast cancer) benefits of lignans, the results are not yet conclusive.[4] Matairesinol has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).[5]

References

  1. Matairesinol at Sigma-Aldrich
  2. 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.
  3. 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.
  4. Linus Pauling Institute at Oregon State University
  5. 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. doi:10.1371/journal.pone.0063354. PMC 3653934Freely accessible. PMID 23691032.
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