Hydroxymatairesinol

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Hydroxymatairesinol
Hydroxymatairesinol.svg
Names
IUPAC name
(7′S,8β,8′α)-4,4′,7′-Trihydroxy-3,3′-dimethoxylignano-9,9′-lactone
Systematic IUPAC name
(3R,4R)-4-[(S)-Hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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/s1
    Key: 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/s1
    Key: UKHWOLNMBQSCLJ-BIENJYKABV
  • COC1=C(C=CC(=C1)C[C@@H]2[C@H](COC2=O)[C@@H](C3=CC(=C(C=C3)O)OC)O)O
Properties
C20H22O7
Molar mass 374.389 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). [1] 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. [1] It has also shown anti-oxidant properties in vitro. [1]

HMR's chemical structure is similar to matairesinol. [2] At high concentrations, HMR has estrogenic properties, which are considerably weaker than those of estradiol. [2]

References

  1. 1 2 3 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. 1 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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