Matairesinol

Matairesinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, e.g. rye, and together with Secoisolariciresinol, has attracted much attention for its beneficial nutritional effects.[2]

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
CAS Number	580-72-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6698
ChEMBL	ChEMBL425148
ChemSpider	106491
DrugBank	DB04200
PubChem CID	119205
UNII	XLW63P8WUA
CompTox Dashboard (EPA)	DTXSID40920490
InChI 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-LSDHHAIUSA-N 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
SMILES O=C2OC[C@H](Cc1cc(OC)c(O)cc1)[C@H]2Cc3ccc(O)c(OC)c3
Properties
Chemical formula	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).
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Infobox references

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 attribut 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.
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. doi:10.1371/journal.pone.0063354. PMC 3653934. PMID 23691032.