Matairesinol: Difference between revisions

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{{chembox
{{Chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462100478
| verifiedrevid = 462100478
| 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/US/en/product/sial/40043 Matairesinol] at [[Sigma-Aldrich]]</ref>
| Name = Matairesinol
| Name = Matairesinol
| ImageFile = Matairesinol.png
| ImageFile = Matairesinol.png
| ImageSize = 200px
| ImageName = Chemical structure of matairesinol
| ImageName = Chemical structure of matairesinol
| IUPACName = (3''R'',4''R'')-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
| IUPACName = (8β,8′α)-4,4′-Dihydroxy-3,3′-dimethoxylignano-9,9′-lactone
| SystematicName = (3''R'',4''R'')-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
| OtherNames = (αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone
| OtherNames = (αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 106491
| ChemSpiderID = 106491
Line 20: Line 21:
| InChIKey1 = MATGKVZWFZHCLI-LSDHHAIUSA-N
| InChIKey1 = MATGKVZWFZHCLI-LSDHHAIUSA-N
| CASNo = 580-72-3
| CASNo = 580-72-3
| CASNo_Ref = {{cascite|changed|??}}=
| CASNo_Ref = {{cascite|correct|CAS}}
| CASOther =
| CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = XLW63P8WUA
| PubChem = 119205
| PubChem = 119205
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 6698
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 425148
| ChEMBL = 425148
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04200
| DrugBank = DB04200
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10682
| 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
| InChI =
| MeSHName =
| MeSHName =
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| C=20|H=22|O=6
| C=20 | H=22 | O=6
| ExactMass = 358.141638 u
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt = <!-- °C -->
| MeltingPt =
| BoilingPt = <!-- °C -->
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
}}
}}


'''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.<ref>{{Ullmann|doi=10.1002/14356007.a06_093.pub2|title=Cereals|year=2006|last1=Seibel|first1=Wilfried|last2=Kim Chung|first2=Okkyung|last3=Weipert|first3=Dorian|last4=Park|first4=Seok-Ho|isbn=3527306730}}</ref>
'''Matairesinol''' is a plant [[lignan]]. It occurs with [[secoisolariciresinol]] in numerous foods such as oil seeds, whole grains, vegetables, and fruits.<ref>{{cite journal |author=Niemeyer HB, Honig DM, Kulling SE, Metzler M |title=Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol |journal=J. Agric. Food Chem. |volume=51 |issue=21 |pages=6317–25 |year=2003 |month=October |pmid=14518962 |doi=10.1021/jf030263n }}</ref>


==Metabolism==
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.<ref>{{cite journal |doi=10.1079/BJN20051371 |author=Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC |title=Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol |journal=Br. J. Nutr. |volume=93 |issue=3 |pages=393–402 |year=2005 |month=March |pmid=15877880 |url=http://journals.cambridge.org/abstract_S0007114505000504}}</ref>
The plant lignans are precursors of the enterolignans (mammalian lignans).<ref>{{cite journal |vauthors=Niemeyer HB, Honig DM, Kulling SE, Metzler M |title=Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol |journal=J. Agric. Food Chem. |volume=51 |issue=21 |pages=6317–25 |date=October 2003 |pmid=14518962 |doi=10.1021/jf030263n }}</ref> 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.<ref>{{cite journal |doi=10.1079/BJN20051371 |vauthors=Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC |title=Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol |journal=Br. J. Nutr. |volume=93 |issue=3 |pages=393–402 |date=March 2005 |pmid=15877880 |doi-access=free }}</ref>


==Biomedical considerations==
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.<ref>[http://lpi.oregonstate.edu/infocenter/phytochemicals/lignans Linus Pauling Institute at Oregon State University<!-- Bot generated title -->]</ref>
Although some studies attribute disease preventative (cardio-protective and hormone associated cancers like breast cancer) benefits of lignans, the results are inconclusive.<ref>[http://lpi.oregonstate.edu/infocenter/phytochemicals/lignans Linus Pauling Institute at Oregon State University<!-- Bot generated title -->]</ref> Matairesinol has been found to act as an [[agonist]] of the [[adiponectin receptor 1]] (AdipoR1).<ref name="pmid23691032">{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354 | bibcode = 2013PLoSO...863354S | doi-access = free }}</ref>


== References ==
== References ==
{{reflist}}
{{reflist}}


{{lignan}}
{{Lignans}}


[[Category:Adiponectin receptor agonists]]
[[Category:Lignans]]
[[Category:Lignans]]
[[Category:Lactones]]
[[Category:Lactones]]

Latest revision as of 11:44, 18 January 2024

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.[2]

Metabolism[edit]

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[edit]

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[edit]

  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.
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