Hydroxymatairesinol

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]

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-[(S)-Hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Identifiers
CAS Number	20268-71-7 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL513565
ChemSpider	9123982
PubChem CID	10948757
UNII	6F59EK4QQH
CompTox Dashboard (EPA)	DTXSID70942387
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/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
SMILES 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
Chemical formula	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). Infobox references

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. 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.