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Hydroxymatairesinol

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Hydroxymatairesinol
Names
IUPAC name (7′S,8β,8′α)-4,4′,7′-Trihydroxy-3,3′-dimethoxylignano-9,9′-lactone
Systematic IUPAC name (3R,4R)-4--3-oxolan-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H22O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1Key: UKHWOLNMBQSCLJ-BIENJYKASA-N
  • InChI=1/C20H22O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1Key: UKHWOLNMBQSCLJ-BIENJYKABV
SMILES
  • COC1=C(C=CC(=C1)C2(COC2=O)(C3=CC(=C(C=C3)O)OC)O)O
Properties
Chemical formula C20H22O7
Molar mass 374.389 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro.

HMR's chemical structure is similar to matairesinol. At high concentrations, HMR has estrogenic properties, which are considerably weaker than those of estradiol.

References

  1. ^ Saarinen, NM; Warri, A; Makela, SI; et al. (2000). "Hydroxymatairesinol, a novel enterolactone precursor with antitumor properties from coniferous tree (Picea abies)". Nutrition and Cancer. 36 (2): 207–16. doi:10.1207/S15327914NC3602_10. PMID 10890032. S2CID 22124446.
  2. ^ Cosentino, M; Marino, F; Ferrari, M; et al. (August 2007). "Estrogenic activity of 7-hydroxymatairesinol potassium acetate (HMR/lignan) from Norway spruce (Picea abies) knots and of its active metabolite enterolactone in MCF-7 cells". Pharmacological Research. 56 (2): 140–7. doi:10.1016/j.phrs.2007.05.001. PMID 17572100.


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