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
CAS Number
  • 580-72-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:6698 ☒N
ChEMBL
  • ChEMBL425148 checkY
ChemSpider
  • 106491 checkY
DrugBank
  • DB04200 checkY
KEGG
  • C10682 checkY
PubChem CID
  • 119205
UNII
  • XLW63P8WUA checkY
CompTox Dashboard (EPA)
  • DTXSID40920490 Edit this at Wikidata
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 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
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
Chemical compound

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.[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 978-3527306732.
  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.
  • v
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Types of lignans
Lignans
Lignan glycosides
Mammalian lignans (enterolignans)Neolignans
Flavonolignans
  • Cinchonain-Ib
  • Dehydrosilybin
  • Deoxysilycistin
  • Deoxysilydianin
  • Hydnocarpin
  • Hydnowightin
  • Neosilyhermin
  • Palstatin
  • Rhodiolin
  • Salcolin A
  • Salcolin B
  • Scutellaprostin A, B, C, D, E and F
  • Silandrin
  • Silyamandin
  • Silibinin
  • Silybinome
  • Silicristin
  • Silydianin
  • Silyhermin
  • Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether
  • Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether