Equol: A comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro

Pamela Magee, Marian Raschke, Claudia Steiner, Julie G. Duffin, Beatrice L. Pool-Zobel, Tuija Jokela, Kristiina Wahala, Ian R. Rowland

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

It has been postulated that the R- and S-equol enantiomers have different biological properties given their different binding affinities for the estrogen receptor S-(-)equol is produced via the bacterial conversion of the soy isoflavone daidzein in the gut. We have compared the biological effects of purified S-equol to that of racemic (R and S) equol on breast and prostate cancer cells of varying receptor status in vitro. Both racemic and S-equol inhibited the growth of the breast cancer cell line MDA-MB-231 (>= 10 mu M) and the prostate cancer cell lines LNCaP (>= 5 mu M) and LAPC-4 (>= 2.5 mu M). The compounds also showed equipotent effects in inhibiting the invasion of MDA-MB-231 and PC-3 cancer cells through matrigel. S-equol (1, 10, 30 mu M) was unable to prevent DNA damage in MCF-7 or MCF-10A breast cells following exposure to 2-hydroxy-4-nonenal, menadione, or benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide. lit contrast, racemic equol (10, 30 mu M) prevented DNA damage in MCF-10A cells following exposure to 2-hydroxy-4-nonenal or menadione. These findings suggest that racemic equol has strong antigenotoxic activity in contrast to the purified S-equol enantionzer implicating the R-, rather than the S-enantiomer as being responsible for the antioxidant effects of equol, a finding that may have implications for the in vivo chemoprotective properties of equol.
LanguageEnglish
Pages232-242
JournalNUTRITION AND CANCER-AN INTERNATIONAL JOURNAL
Volume54
Issue number2
DOIs
Publication statusPublished - 2006

Fingerprint

Equol
Prostate
Breast
DNA
Growth
Vitamin K 3
DNA Damage
Prostatic Neoplasms
In Vitro Techniques
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
Breast Neoplasms
Cell Line
Isoflavones
Estrogen Receptors

Cite this

Magee, Pamela ; Raschke, Marian ; Steiner, Claudia ; Duffin, Julie G. ; Pool-Zobel, Beatrice L. ; Jokela, Tuija ; Wahala, Kristiina ; Rowland, Ian R. / Equol: A comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro. In: NUTRITION AND CANCER-AN INTERNATIONAL JOURNAL. 2006 ; Vol. 54, No. 2. pp. 232-242.
@article{f5ad82e3d7b64de1b1e69713d3af431f,
title = "Equol: A comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro",
abstract = "It has been postulated that the R- and S-equol enantiomers have different biological properties given their different binding affinities for the estrogen receptor S-(-)equol is produced via the bacterial conversion of the soy isoflavone daidzein in the gut. We have compared the biological effects of purified S-equol to that of racemic (R and S) equol on breast and prostate cancer cells of varying receptor status in vitro. Both racemic and S-equol inhibited the growth of the breast cancer cell line MDA-MB-231 (>= 10 mu M) and the prostate cancer cell lines LNCaP (>= 5 mu M) and LAPC-4 (>= 2.5 mu M). The compounds also showed equipotent effects in inhibiting the invasion of MDA-MB-231 and PC-3 cancer cells through matrigel. S-equol (1, 10, 30 mu M) was unable to prevent DNA damage in MCF-7 or MCF-10A breast cells following exposure to 2-hydroxy-4-nonenal, menadione, or benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide. lit contrast, racemic equol (10, 30 mu M) prevented DNA damage in MCF-10A cells following exposure to 2-hydroxy-4-nonenal or menadione. These findings suggest that racemic equol has strong antigenotoxic activity in contrast to the purified S-equol enantionzer implicating the R-, rather than the S-enantiomer as being responsible for the antioxidant effects of equol, a finding that may have implications for the in vivo chemoprotective properties of equol.",
author = "Pamela Magee and Marian Raschke and Claudia Steiner and Duffin, {Julie G.} and Pool-Zobel, {Beatrice L.} and Tuija Jokela and Kristiina Wahala and Rowland, {Ian R.}",
year = "2006",
doi = "10.1207/515327914nc5402_10",
language = "English",
volume = "54",
pages = "232--242",
journal = "Nutrition and Cancer - An International Journal",
issn = "0163-5581",
number = "2",

}

Equol: A comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro. / Magee, Pamela; Raschke, Marian; Steiner, Claudia; Duffin, Julie G.; Pool-Zobel, Beatrice L.; Jokela, Tuija; Wahala, Kristiina; Rowland, Ian R.

In: NUTRITION AND CANCER-AN INTERNATIONAL JOURNAL, Vol. 54, No. 2, 2006, p. 232-242.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Equol: A comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro

AU - Magee, Pamela

AU - Raschke, Marian

AU - Steiner, Claudia

AU - Duffin, Julie G.

AU - Pool-Zobel, Beatrice L.

AU - Jokela, Tuija

AU - Wahala, Kristiina

AU - Rowland, Ian R.

PY - 2006

Y1 - 2006

N2 - It has been postulated that the R- and S-equol enantiomers have different biological properties given their different binding affinities for the estrogen receptor S-(-)equol is produced via the bacterial conversion of the soy isoflavone daidzein in the gut. We have compared the biological effects of purified S-equol to that of racemic (R and S) equol on breast and prostate cancer cells of varying receptor status in vitro. Both racemic and S-equol inhibited the growth of the breast cancer cell line MDA-MB-231 (>= 10 mu M) and the prostate cancer cell lines LNCaP (>= 5 mu M) and LAPC-4 (>= 2.5 mu M). The compounds also showed equipotent effects in inhibiting the invasion of MDA-MB-231 and PC-3 cancer cells through matrigel. S-equol (1, 10, 30 mu M) was unable to prevent DNA damage in MCF-7 or MCF-10A breast cells following exposure to 2-hydroxy-4-nonenal, menadione, or benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide. lit contrast, racemic equol (10, 30 mu M) prevented DNA damage in MCF-10A cells following exposure to 2-hydroxy-4-nonenal or menadione. These findings suggest that racemic equol has strong antigenotoxic activity in contrast to the purified S-equol enantionzer implicating the R-, rather than the S-enantiomer as being responsible for the antioxidant effects of equol, a finding that may have implications for the in vivo chemoprotective properties of equol.

AB - It has been postulated that the R- and S-equol enantiomers have different biological properties given their different binding affinities for the estrogen receptor S-(-)equol is produced via the bacterial conversion of the soy isoflavone daidzein in the gut. We have compared the biological effects of purified S-equol to that of racemic (R and S) equol on breast and prostate cancer cells of varying receptor status in vitro. Both racemic and S-equol inhibited the growth of the breast cancer cell line MDA-MB-231 (>= 10 mu M) and the prostate cancer cell lines LNCaP (>= 5 mu M) and LAPC-4 (>= 2.5 mu M). The compounds also showed equipotent effects in inhibiting the invasion of MDA-MB-231 and PC-3 cancer cells through matrigel. S-equol (1, 10, 30 mu M) was unable to prevent DNA damage in MCF-7 or MCF-10A breast cells following exposure to 2-hydroxy-4-nonenal, menadione, or benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide. lit contrast, racemic equol (10, 30 mu M) prevented DNA damage in MCF-10A cells following exposure to 2-hydroxy-4-nonenal or menadione. These findings suggest that racemic equol has strong antigenotoxic activity in contrast to the purified S-equol enantionzer implicating the R-, rather than the S-enantiomer as being responsible for the antioxidant effects of equol, a finding that may have implications for the in vivo chemoprotective properties of equol.

U2 - 10.1207/515327914nc5402_10

DO - 10.1207/515327914nc5402_10

M3 - Article

VL - 54

SP - 232

EP - 242

JO - Nutrition and Cancer - An International Journal

T2 - Nutrition and Cancer - An International Journal

JF - Nutrition and Cancer - An International Journal

SN - 0163-5581

IS - 2

ER -