NDLI: Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs)

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Contents list

Vitamin D insufficiency and chronic diseases: Hype and reality

The health benefits of blackcurrants

Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs)

Mango fruit peel and flesh extracts affect adipogenesis in 3T3-L1 cells

Protective role of Brassica olerecea and Eugenia jambolana extracts against H₂O₂ induced cytotoxicity in H9C2 cells

Hypericum androsaemum water extract inhibits proliferation in human colorectal cancer cells through effects on MAP kinases and PI3K/Akt pathway

The soluble dietary fiber inulin can influence the bioaccessibility of enniatins

Complexation of high methoxyl pectin with ethanol desolvated whey protein nanoparticles: physico-chemical properties and encapsulation behaviour

Hypotensive, hypoglycaemic and antioxidant effects of consuming a cocoa product in moderately hypercholesterolemic humans

Anti-inflammatory effects of pomegranate (Punica granatum L.) husk ellagitannins in Caco-2 cells, an in vitro model of human intestine

Scopoletin attenuates allergy by inhibiting Th2 cytokines production in EL-4 T cells

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Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs)

Content Provider	Royal Society of Chemistry (RSC)
Author	Vincken, Jean-Paul Bovee, Toine F. H. Gruppen, Harry Verbruggen, Marian A. Simons, Rudy
Copyright Year	2012
Abstract	Isoflavonoids are a class of secondary metabolites, which comprise amongst others the subclasses of isoflavones, isoflavans, pterocarpans and coumestans. Isoflavonoids are abundant in Leguminosae, and many of them can bind to the human estrogen receptor (hER) with affinities similar to or lower than that of estradiol. Dietary intake of these so-called phytoestrogens has been associated with positive effects on menopausal complaints, hormone-related cancers, and osteoporosis. Therefore, phytoestrogens are used as nutraceuticals in functional foods or food supplements. Most of the isoflavonoids show agonistic activity towards both hERα and hERβ, the extent of which is modulated by the substitution pattern of their skeleton (i.e. –OH, –OCH3). Interestingly, substitutions consisting of a five-carbon prenyl group often seem to result in an antiestrogenic activity. There is growing evidence that the action of some of these prenylated isoflavonoids is tissue-specific, suggesting that they act like selective estrogen receptor modulators (SERMs), such as the well-known chemically synthesized raloxifene and tamoxifen. These so-called phytoSERMS might have high potential for realizing new food and pharma applications. In this review, the structural features of isoflavonoids (i.e. the kind of skeleton and prenylation (e.g. chain or pyran), position of the prenyl group on the skeleton, and the extent of prenylation (single, double)) are discussed in relation to their estrogenic activity. Anti-estrogenic and SERM activity of isoflavonoids was always associated with prenylation, but these activities did not seem to be confined to one particular kind/position of prenylation or isoflavonoid subclass. Few estrogens with agonistic activity were prenylated, but these were not tested for antagonistic activity; possibly, these molecules will turn out to be phytoSERMs as well. Furthermore, the data on the dietary occurrence, bioavailability and metabolism of prenylated isoflavonoids are discussed.
Starting Page	810
Ending Page	827
Page Count	18
File Format	HTM / HTML PDF
ISSN	20426496
Volume Number	3
Issue Number	8
Journal	Food & Function
DOI	10.1039/c2fo10290k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Leguminosae Isoflavones Pterocarpan Fabaceae Estrogen receptor Estradiol Menopause Osteoporosis Prenylation Raloxifene Tamoxifen Pharmaceutical industry Pyran Isoflavonoid Bioavailability Metabolism
Content Type	Text
Resource Type	Article
Subject	Medicine Food Science

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The NSABP Study of Tamoxifen and Raloxifene (STAR) trial.

National Trends in Osteoporosis Visits and Osteoporosis Treatment, 1988-2003

The Effects of Estradiol, Androgens and the Selective Estrogen Modulators: Ospemifene, Raloxifene and Tamoxifen on Explant Cultures of Human Breast Tissue

Inhibition of Intimal Hyperplasia Using the Selective Estrogen Receptor Modulator Raloxifene

Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

Differential effects of selective oestrogen receptor modulators (SERMs) tamoxifen, ospemifene and raloxifene on human osteoclasts in vitro.

Menopause: new therapies.

Effects of SERM (selective estrogen receptor modulator) treatment on growth and proliferation in the rat uterus

The Role of Selective Estrogen Receptor Modulators on Breast Cancer: From Tamoxifen to Raloxifene

Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs)

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