Enterolactone

Names

[ Name ]:
Enterolactone

[Synonym ]:
HPMF
HBBL
(3R,4R)-3,4-Bis(3-hydroxybenzyl)dihydrofuran-2(3H)-one
trans-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone
Enterolaktone
2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-, (3R,4R)-rel-
2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-, trans-
Enterolakton
2(3H)-Furanone, dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-, (3R,4R)-
ENTEROLACTON
rac Enterolactone
(3R,4R)-3,4-Bis(3-hydroxybenzyl)dihydro-2(3H)-furanone
Compound 180/442

Biological Activity

[Description]:

Enterolactone is a bioactive phenolic metabolite known as a mammalian lignan derived from dietary lignans. Enterolactone has estrogenic properties and anti-breast cancer activity[1]. Enterolactone is a radiosensitizer for human breast cancer cell lines through impaired DNA repair and increased apoptosis[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[In Vitro]

Enterolactone (25-75 μM; 48 hours) arrests the growth of MDA-MB-231 breast cancer cells in the ‘S’ phase[1] Enterolactone (25-75 μM; 15 hours) triggers apoptosis in MDA-MB-231 breast cancer cells via caspase-3 activation[1]. Enterolactone inhibits TGF-β-induced migration of MDA-MB-231 breast cancer cells. Enterolactone inhibits TGF-β-induced invasion of MDA-MB-231 breast cancer cells through ECM. Enterolactone inhibits the TGF-β-induced EMT program in MDA-MB-231 breast cancer cells. Enterolactone reduces the formation of actin stress fibers by inhibiting the expression of CD44 and MAPK-p38. Enterolactone inhibits the ERK/NF-κB/Snail signaling pathway to revert TGF-β-induced EMT in MDA-MB-231 cells[1]. Cell Viability Assay[1] Cell Line: MDA-MB-231 cells Concentration: 25, 50, 75 μM Incubation Time: 48 hours Result: There was a non-significant increase (~24%) in the S phase population following treatment with 25 μM EL, whereas there were significant increases (~34% and ~39%) following treatment with 50 and 75 μM EL, respectively.

[References]

[1]. Bigdeli B, et al. Enterolactone: A novel radiosensitizer for human breast cancer cell lines through impaired DNA repair and increased apoptosis. Toxicol Appl Pharmacol. 2016;313:180-194.

[2]. Mali AV, et al. Enterolactone modulates the ERK/NF-κB/Snail signaling pathway in triple-negative breast cancer cell line MDA-MB-231 to revert the TGF-β-induced epithelial-mesenchymal transition. Cancer Biol Med. 2018;15(2):137-156.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
561.4±25.0 °C at 760 mmHg

[ Melting Point ]:
141-143°C (lit.)

[ Molecular Formula ]:
C₁₈H₁₈O₄

[ Molecular Weight ]:
298.33

[ Flash Point ]:
209.0±16.7 °C

[ Exact Mass ]:
298.120514

[ PSA ]:
66.76000

[ LogP ]:
2.29

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.635

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport