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The Influence of Plant Isoflavones Daidzein and Equol on Female

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The Influence of Plant Isoflavones Daidzein and Equol on Female pharmaceuticals Review The Influence of Plant Isoflavones Daidzein and Equol on Female Reproductive Processes Alexander V. Sirotkin 1,* , Saleh Hamad Alwasel 2 and Abdel Halim Harrath 2 1 Department of Zoology and Anthropology, Constantine the Philosopher University in Nitra, 949 01 Nitra, Slovakia 2 Department of Zoology, College of Science, King Saud University, Riyadh 12372, Saudi Arabia; [email protected] (S.H.A.); [email protected] (A.H.H.) * Correspondence: [email protected]; Tel.: +421-903561120 Abstract: In this review, we explore the current literature on the influence of the plant isoflavone daidzein and its metabolite equol on animal and human physiological processes, with an emphasis on female reproduction including ovarian functions (the ovarian cycle; follicullo- and oogenesis), fundamental ovarian-cell functions (viability, proliferation, and apoptosis), the pituitary and ovarian endocrine regulators of these functions, and the possible intracellular mechanisms of daidzein action. Furthermore, we discuss the applicability of daidzein for the control of animal and human female reproductive processes, and how to make this application more efficient. The existing literature demonstrates the influence of daidzein and its metabolite equol on various nonreproductive and reproductive processes and their disorders. Daidzein and equol can both up- and downregulate the ovarian reception of gonadotropins, healthy and cancerous ovarian-cell proliferation, apoptosis, viability, ovarian growth, follicullo- and oogenesis, and follicular atresia. These effects could be mediated by daidzein and equol on hormone production and reception, reactive oxygen species, and intracellular regulators of proliferation and apoptosis. Both the stimulatory and the inhibitory Citation: Sirotkin, A.V.; Alwasel, effects of daidzein and equol could be useful for reproductive stimulation, the prevention and S.H.; Harrath, A.H. The Influence of mitigation of cancer development, and the adverse effects of environmental stressors in reproductive Plant Isoflavones Daidzein and Equol biology and medicine. on Female Reproductive Processes. Pharmaceuticals 2021, 14, 373. https:// Keywords: daidzein; equol; reproduction; ovarian folliculogenesis; oogenesis; proliferation; apopto- doi.org/10.3390/ph14040373 sis; hormone; reception; fecundity Academic Editor: Félix Carvalho Received: 21 March 2021 1. Introduction Accepted: 15 April 2021 Published: 17 April 2021 Reproduction is considered to be the most important process for the continued ex- istence of species, but it is also a complicated process from a regulatory viewpoint. Un- Publisher’s Note: MDPI stays neutral derstanding the physiological and natural regulators of reproduction is important for with regard to jurisdictional claims in characterizing, predicting, and controlling reproductive processes, and for the prevention published maps and institutional affil- and treatment of reproductive disorders. A promising regulator, protector, and therapy is iations. daidzein and its related plant molecules. In recent decades, daidzein was widely studied because of its health benefits, mainly in the prevention of cancer. The results of these epidemiological [1], biomedical [2–5], and biochemical [6–8] studies were described in several reviews. There are, however, no reviews summarizing the existing literature on daidzein and its effect on reproductive processes. Available reviews on daidzein in re- Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. lation to female reproduction do not include findings from the last decade [9], or they This article is an open access article only explore a niche area of the field, e.g., daidzein’s effect on preventing menopausal distributed under the terms and syndrome [10,11] or estrogen-related illnesses [12]. Our review incorporates recent find- conditions of the Creative Commons ings on the influence of daidzein and its metabolite equol on animal and human female Attribution (CC BY) license (https:// reproductive processes (ovarian cycle, follicullo- and oogenesis), basic ovarian-cell func- creativecommons.org/licenses/by/ tions (viability, proliferation, apoptosis), the pituitary and ovarian endocrine regulators 4.0/). of these functions, the possible intracellular mechanisms of daidzein action on ovarian Pharmaceuticals 2021, 14, 373. https://doi.org/10.3390/ph14040373 https://www.mdpi.com/journal/pharmaceuticals Pharmaceuticals 2021, 14, x FOR PEER REVIEW 2 of 11 Pharmaceuticals 2021, 14, 373 2 of 10 regulators of these functions, the possible intracellular mechanisms of daidzein action on ovarian cells, controlling animal and human female reproductive processes, and how to makecells, this controlling application animal more and efficient. human female reproductive processes, and how to make this application more efficient. 2. Provenance and Properties of Daidzein and Its Metabolite Equol 2. Provenance and Properties of Daidzein and Its Metabolite Equol Isoflavones (including daidzein, the glycoside forms of daidzein, and glycitein, the Isoflavones (including daidzein, the glycoside forms of daidzein, and glycitein, the methoxylated form of daidzein) are bioactive compounds that are present in significant methoxylated form of daidzein) are bioactive compounds that are present in significant quantitiesquantities in in legumes, legumes, soybeans, soybeans, green green beans, beans, and and mung mung beans. beans. In grains In grains (raw (raw materials), materi- theyals), are they mostly are mostly present present as simple as simple and complex and complex O-glycosides, O-glycosides, β-glucuronidesβ-glucuronides and sulfate and esters,sulfate and esters, highly and highlypolar, water-soluble polar, water-soluble compounds. compounds. They are They hardly are hardly absorbed absorbed by the by intestinalthe intestinal epithelium epithelium and andhave have insignificant insignificant biological biological activities. activities. Beans Beans are areincluded included in variousin various food food products products owing owing to their to their digestibility, digestibility, taste, taste, bioavailability bioavailability of nutrients, of nutrients, and higherand higher amounts amounts of bioactives. of bioactives. Processing Processing steps stepsinclude include steaming, steaming, cooking, cooking, roasting, roasting, and microbialand microbial fermentation, fermentation, which which destroys destroys prot proteaseease inhibitors inhibitors and and cleaves cleaves the the glycoside glycoside bondbond to to yield yield absorbable absorbable and and bioactive bioactive aglyco aglyconene in in the the processed processed products, products, such such as as miso, miso, natto,natto, soy soy milk, milk, tofu, tofu, and and increases increases the the product’ product’ss shelf shelf life. life. Results Results are are reliable reliable (including (including thethe conversion conversion of of glucoside glucoside daidzein daidzein to to aglicon aglicon daidzein, daidzein, which which hydrolyzes hydrolyzes conjugated conjugated isoflavonesisoflavones with with gut gut bacteria) bacteria) [2–4,6]. [2–4,6]. Clinical Clinical studies studies show show the the differences differences between between the the biologicalbiological activities activities of of aglycone aglycone and and conjugat conjugateded forms forms of of daidzein daidzein [2 [2].]. Processed Processed soy soy food food productsproducts were were an an integral integral part part of of diets diets in in many many Asia-Pacific Asia-Pacific countries countries for for centuries, centuries, but but in in thethe last last two two decades, decades, soy soy products products were were succe successfullyssfully integrated integrated into into Western Western diets diets because because ofof their their health health benefits benefits [3]. [3]. DaidzeinDaidzein (7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one)(7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one) (PubChem (PubChem ID 5281708, ID 5281708,molecular molecular formula C15H10O4; formula C15H10O4; chemical structure chemical indicated structure in Figure indicated1a, https://pubchem. in Figure 1a, https://pubchem.ncbi.nlm.nih.gov/)ncbi.nlm.nih.gov/ (accessed on 16 April is 2021))an is isoflavonoid an isoflavonoid derived derived from from L-phenylalanine. L-phenylalanine. DaidzeinDaidzein is anan aglycone aglycone form form of daidzein.of daidzein. Its solubility Its solubility in water in iswater relatively is relatively low; therefore, low; therefore,for medical for purposes, medical itpurposes, is dissolved it is in dissolved alcohol or in an alcohol alcohol/water or an alcohol/water mixture. mixture. (A) (B) FigureFigure 1. 1. ChemicalChemical structures structures of of (A (A) daidzein) daidzein and and (B ()B equol) equol (https://pubchem.ncbi.nlm.nih.gov/ (https://pubchem.ncbi.nlm.nih.gov/ (accessed(accessed on on 16 16 April April 2021). 2021)). TheThe primary primary biological biological and and health health effect effect of daidzein of daidzein is because is because of its metabolite, of its metabolite, equol ((3S)-3-(4-hydroxyphenyl)-7-chromanol)equol ((3S)-3-(4-hydroxyphenyl)-7-chromanol) (PubChem (PubChem ID, ID,6950272 6950272 molecular molecular formula formula C15H14O3;C15H14O3; chemicalchemical structure indicatedstructure in Figureindicated1b, https://pubchem.ncbi.nlm.nih.gov/ in Figure 1b, https://pubchem.ncbi.nlm.nih.gov/).(accessed on 16 April 2021)). Equol Equol is an isoflavandiolis an isoflavandiol nonsteroidal nonsteroidal estrogen estrogen
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