Matairesinol: Difference between revisions

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| verifiedrevid = 400294983
| verifiedrevid = 400294983
| Reference = <ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=40043|FLUKA&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Matairesinol] at [[Sigma-Aldrich]]</ref>
| Reference = <ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=40043|FLUKA&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Matairesinol] at [[Sigma-Aldrich]]</ref>
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| PubChem = 119205
| PubChem = 119205
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 425148
| ChEMBL = 425148
| SMILES = O=C2OC[C@H](Cc1cc(OC)c(O)cc1)[C@H]2Cc3ccc(O)c(OC)c3
| SMILES = O=C2OC[C@H](Cc1cc(OC)c(O)cc1)[C@H]2Cc3ccc(O)c(OC)c3

Revision as of 15:37, 1 August 2011

Matairesinol[1]
Chemical structure of matairesinol
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
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
  • 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 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]

References

  1. ^ Matairesinol at Sigma-Aldrich
  2. ^ Niemeyer HB, Honig DM, Kulling SE, Metzler M (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Linus Pauling Institute at Oregon State University