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Isoflavonoids and Phytoestrogenic Activity

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Natural Products

Abstract

In the early 1930s, some isoflavonoid compounds were discovered to exhibit estrogenic activities that were found to be deleterious at high doses for cattle reproduction. Later, several toxicological studies on these compounds were performed between the 1940s and 1980s using mainly rodent models. These same compounds were discovered in edible plants and in human biological fluids, and a large body of scientific work was then dedicated to their putative impact on human health.

Because estradiol is a natural hormone with ubiquitous effects in mammals, nearly all biological functions can be influenced by isoflavonoids that have estrogenic activities. Their effects are significantly affected by their biological concentrations in body fluids and by their affinity to known estradiol receptors. Our knowledge of the biological effects of estrogenic isoflavonoids progresses the more we learn about the effects of estradiol and of endocrine disruptors. In this respect, the latest information concerns the discovery of both new pathways for cellular action and epigenetic effects. In addition, the two latest issues involve the factors influencing the metabolism of phytoestrogenic compounds and their bioavailability, and this confirms the importance of the efficient doses and of their affinities for the estradiol receptors.

After a general introduction on the classical molecular effects of estradiol, this chapter presents the main isoflavones with estrogenic activities that have been investigated so far, with their plant sources and forms as well as their role in plants. Their presence in human food and their bioavailable forms in human and in animal models are then evoked. Next, this chapter presents the latest data concerning their mechanisms of action and explains how these processes can influence more highly integrated physiological functions. The data from animal studies and epidemiological studies are discussed as an introduction to pharmacological applications demonstrated in clinical trials. Because estradiol in mammals can have both beneficial and harmful effects, depending on the dose, the physiological status, and the target organ, the dark side of the story of phytoestrogenic compounds is also exposed.

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Abbreviations

17β-E2 :

17β-Estradiol

3-PBA:

3-Phenoxybenzoic acid

5-AR:

5α-Reductase

8-PN:

8-Prenyl naringenin

AFP:

α-Fetoprotein

AKt:

Protein kinase B

AMH:

Anti-mullerian hormone

AR:

Androgen receptor

ARKO:

Aromatase knock out

Bioch:

Biochanin A

BMC:

Bone mineral content

BMD:

Bone mineral density

BMI:

Body mass index

BTM:

Bone turn-over markers

CCa:

Colon cancer

C max :

Maximum concentration

CREB:

c-AMP response element binding protein

DLD-1:

Colon cancer cell line

DMBA:

Dimethylbenz[a]anthracene

DNA:

Deoxyribonucleic acid

DPX:

Deoxypyridinoline (Bone resorption marker)

E2 :

Estradiol

EGFR:

Epidermal growth factor receptor

Eq :

Equol & its isomer S-Equol S -Eq

ERE:

Estrogen responsive element

ERK:

Extracellular related kinase

ERR:

Estrogen related receptor with isoforms α, β, γ

ERs:

Estradiol receptors

ERα:

Estradiol receptor α

ERβ:

Estradiol receptor β

ESR1:

Gene coding for estradiol receptor alpha

ESR2:

Gene coding for estradiol receptor beta

Form:

Formononetin

FSH:

Follicle stimulating hormone

Gapd-s:

Glyceraldehyde 3-phosphate dehydrogenase gene

Gen :

Genistein

Gly :

Glycitein

GnRH:

Gonadotropin releasing hormone

GPCR:

G-protein coupled receptor

GPR-30:

G protein Receptor-30

HRT:

Hormone replacement therapy

IC 50 :

Inhibiting concentration for 50 %

ICI 182,780:

Estradiol receptor specific inhibitor

IGF-1:

Insulin like growth factor-1

IL-6:

Interleukin 6

Isofl :

Isoflavones

JNK:

c-Jun N-terminal kinase

LBD:

Ligand binding domain

LH:

Luteinizing hormone

LNCap:

Prostate cancer cell line

MAPK:

Mutagen activated protein kinase

MCF-7:

Breast cancer cell line

MDM2:

Proto-oncogene in estrogen-dependent tissues

MDR:

Multi-drug resistance

NTx:

n-Telopeptide (Bone resorption marker)

OECD:

Organization for economic cooperation and development

OPG:

Osteoprotegerin

OR:

Odd Ratio

PC-3:

Prostate cancer cell line

PCa:

Prostate cancer

PI3K:

Phosphatidyl inositol 3 kinase

PIP:

Phosphatidyl inositol (3,4,5)-trisphosphate

PKC:

Protein kinase C

PSA:

Prostate serum antigen

PTH:

Parathyroid hormone (Hypercalcemic hormone)

PTK:

Protein tyrosine kinase

RANK:

Receptor activator for nuclear factor κB

RANK-L:

Receptor activator for nuclear factor κB Ligand

RR:

Relative risk

SDN-POA:

Sexually dimorphic nucleus of the preoptic area

SF-1:

Steroid factor 1

SHBG:

Sex hormone binding globulin

SPE:

Soy protein extract

Src:

Proto-oncogenes coding for a family of tyrosine kinase

T:

Testosterone

T 1/2 :

half-life time to reach half concentration

T max :

Time for maximum concentration

UDPGT:

Uranyl di-phosphate Glucuronosyltransferase

UGT:

Uranyl di-phosphate Glucuronosyltransferase

WHI:

Women’s health initiative (large American interventional study to assess the effects of HRT on cardiovascular diseases)

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Authors and Affiliations

  1. Physiopathologie de la plasticité neuronale, U862, Université de Bordeaux, Bordeaux, 33000, France

    Prof. Catherine Bennetau-Pelissero

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  1. Prof. Catherine Bennetau-Pelissero
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Correspondence to Catherine Bennetau-Pelissero .

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Editors and Affiliations

  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Bennetau-Pelissero, C. (2013). Isoflavonoids and Phytoestrogenic Activity. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_80

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