DOCSLIB.ORG

PDF Download

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
PDF Download 514 Reviews New Concepts, Experimental Approaches, and Dereplication Strategies for the Discovery of Novel Phytoestrogens from Natural Sources Authors Thomas Michel, Maria Halabalaki, Alexios-Leandros Skaltsounis Affiliation Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Athens, Greece Key words Abstract phy-biochemical detection, frontal affinity chro- l" phytoestrogens ! matography-mass spectrometry and pulsed ul- l" plant extract Phytoestrogens constitute an attractive research trafiltration-MS will also be presented. Finally, l" dereplication topic due to their estrogenic profile and their bio- miniaturized methods (microchip and biosensor) l" extraction logical involvement in womanʼs health. Therefore, will be also discussed. l" isolation l" identification numerous studies are currently performed in nat- With the current review, we attempt to give a ural products chemistry area aiming at the dis- wide and holistic overview of the different ap- covery of novel phytoestrogens. The main classes proaches which could be employed in the discov- of phytoestrogens are flavonoids (flavonols, flava- ery of new phytoestrogens. On the other hand, we nones), isoflavonoids (isoflavones, coumestans), anticipate to attract more scientists to the area of lignans, stilbenoids as well as miscellaneous phytoestrogens and to indicate the need of multi- chemical groups abundant in several edible and/ disciplinary concepts. or medicinal plants, belonging mostly to the Le- guminosae family. As for other bioactives, the de- tection of new structures and more potent plant- Abbreviations derived phytoestrogens typically follows the gen- ! eral approaches currently available in the natural ACN: acetonitrile product discovery process. Plant-based ap- ASE: accelerated solvent extraction proaches selected from traditional medicine BCD: biochemical detection knowledge and bioguided concepts are routinely BuOH: butanol employed. However, these approaches are associ- CCC: countercurrent chromatography received February 3, 2013 ated with serious disadvantages such as time- Co(II)-PAB: cobalt(II)-coated paramagnetic revised February 3, 2013 consuming, repeated, and labor intensive pro- affinity beads accepted February 5, 2013 cesses as well as lack of specificity and reproduci- CPC: centrifugal partition chromatography Bibliography bility. In recent years, the natural products chem- DAD: diode array detector DOI http://dx.doi.org/ istry became more technology-driven, and sev- DPPH: 2,2-diphenyl-1-picrylhydrazyl 10.1055/s-0032-1328300 eral different strategies have been developed. EA: ethyl acetate This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. Published online March 11, 2013 Structure-oriented procedures and miniaturized ER: estrogen receptor Planta Med 2013; 79: 514–532 approaches employing advanced hyphenated an- ERE: estrogen response elements © Georg Thieme Verlag KG alytical platforms have recently emerged. They fa- EtOH: ethanol Stuttgart · New York · cilitate significantly not only the discovery of nov- FAC: frontal affinity chromatography ISSN 0032‑0943 el phytoestrogens but also the dereplication pro- FRET: fluorescence resonance energy Correspondence cedure leading to the anticipation of major draw- transfer Dr. Maria Halabalaki backs in natural products discovery. In this re- FTICR: Fourier transform ion cyclotron Laboratory of Pharmacognosy and Natural Products Chemistry view, apart from the traditional concepts followed resonance School of Pharmacy in phytochemistry for the discovery of novel bio- GC‑MS: gas chromatography-MS National and Kapodistrian logically active compounds, recent applications in Hept: heptane University of Athens Panepistimioupoli, Zografou the field of extraction, analysis, fractionation, and Hex: hexane 15771 Athens identification of phytoestrogens will be dis- HPLC: high-performance liquid Greece cussed. Moreover, specific methodologies com- chromatography Phone: + 302107754032 Fax:+302107754594 bining identification of actives and biological HRMS: high-resolution mass spectrometry [email protected] evaluation in parallel, such as liquid chromatogra- HSCCC: high-speed CCC Michel T et al. New Concepts, Experimental … Planta Med 2013; 79: 514–532 Reviews 515 HTS: high-throughput screening PUF: pulsed ultrafiltration LC‑BCD: online LC-based biochemical detection QTOF: quadrupole time-of-flight MAE: microwave-assisted extraction RP: reversed phase MAS: microwave-assisted sonication SERM: selective estrogen receptor modulator MeOH: methanol SFE: supercritical fluid extraction MS: mass spectrometry SHBG: sex hormone binding globulin MSPD: matrix solid phase dispersion SPE: solid phase extraction MtBE: methyl tert-butyl ether SWE: subcritical water extraction NMR: nuclear magnetic resonance TFA: trifluoroacetic acid PCA: principal component analysis UAE: ultrasound-assisted extraction PDMS: polydimethylsiloxane UHPLC: ultra high-performance liquid chromatography PLE: pressurized liquid extraction UMAE: ultrasound- and microwave-assisted extraction Introduction properties (selectivity) depending on the receptor content of spe- ! cific tissues (ERα and ERβ populations) and the concentration of Phytoestrogens are nonsteroidal natural compounds, usually the endogenous estrogens. Finally, phytoestrogens may also have plant constituents or their metabolites, which induce biological no affinity to ER (iv); in this case they act through alternative responses in mammals mimicking or modulating the action of mechanisms such as inhibition or activation of specific enzymes endogenous estrogens (i.e., 17β-estradiol, estriol, estrone). Semi- implied in an estrogenic response [2,10] or altering the total synthetic products and synthetic analogues of natural phytoes- amount of free estrogens in the organism. For instance, it has trogens are also sporadically included [1,2]. The role of phytoes- been reported that phytoestrogens interfere with the synthesis trogens and their possible protective effect in hormone-related of steroid hormones by inhibiting specific enzymes such as aro- disorders and diseases such as postmenopausal syndrome, osteo- matase (responsible for the conversion of androgens to estro- porosis, breast and prostate cancer, and cardiovascular complica- gens) [11,12] and 17β-hydroxysteroid oxydoreductase (respon- tions has been extensively investigated [3–6]. sible for the conversion of estrone to estradiol) [13]. Furthermore, The biological action of phytoestrogens is mainly implemented it has been suggested that phytoestrogens are able to stimulate, through their ability to bind to the ER which belongs to the nu- in the liver, the synthesis of proteins which are capable to bind clear receptors superfamily. To date, two main isoforms, ERα and estrogens (SHBG), affecting the overall percentage of free estro- ERβ, encoded by two different genes, have been described [7]. gens in the blood circulation [14,15] and thereby exhibiting an The primary structure of ER is characterized by three main func- indirect estrogenic effect. tional domains: the area responsible for the binding with the li- On the basis of their chemical structure and in respect to biosyn- gand (hormone, phytoestrogens), the region responsible for the thesis patterns, phytoestrogens may be divided in chalcones, fla- interaction with DNA, and the region regulating transcription [8, vonoids (flavones, flavonols, flavanones, isoflavonoids), lignans, 9]. The two isoforms are differently distributed to organs and tis- stilbenoids, and miscellaneous classes. Particular attention sues and present a different affinity to ligands. should be given to isoflavonoids, the subgroup of flavonoids Phytoestrogens can act either as estrogen agonists or antagonists which includes amongst others the chemical groups of isofla- since they may trigger (i) an estrogenic response, thereby binding vones, isoflavanones, pterocarpanes, and coumestans (l" Fig. 1) and activating the ER, which ultimately induces an estrogenic ef- [16,17]. fect or (ii) an antiestrogenic response, blocking or altering the re- These phytochemicals belong to the wide class of polyphenols ceptor activation by endogenous estrogens and thereby inhib- which are ubiquitous in the plant kingdom and characterized by iting an estrogenic effect. Furthermore, phytoestrogens have also nonsteroidal structures (l" Fig. 1). Specific structural characteris- been classified as SERM. Thus, phytoestrogens can act as estrogen tics resembling those of endogenous estrogens and consequently agonists and antagonists at the same time usually in an organ-de- demonstrating an estrogenic profile are responsible for their af- pendent manner resulting in (iii) mixed agonistic/antagonistic finity to the ER receptor. This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. Fig. 1 Chemical structures of representative phy- toestrogens. Michel T et al. New Concepts, Experimental … Planta Med 2013; 79: 514–532 516 Reviews In particular, the estrogenicity of a molecule which is imple- tive. Chemically, they are compounds consisting of two phenyl- mented through ER is related to specific structural requirements propanoid units linked via a carbon–carbon single bond. The such as the presence of hydroxyl groups able to form hydrogen most active lignans are enterodiol and enterolactone which orig- bonds with key functional amino acids of the binding pocket of
Load more

Recommended publications
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Lyme Disease (Chronic)
    Dr.
    [Show full text]
  • Natural Skin‑Whitening Compounds for the Treatment of Melanogenesis (Review)
    EXPERIMENTAL AND THERAPEUTIC MEDICINE 20: 173-185, 2020 Natural skin‑whitening compounds for the treatment of melanogenesis (Review) WENHUI QIAN1,2, WENYA LIU1, DONG ZHU2, YANLI CAO1, ANFU TANG1, GUANGMING GONG1 and HUA SU1 1Department of Pharmaceutics, Jinling Hospital, Nanjing University School of Medicine; 2School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210002, P.R. China Received June 14, 2019; Accepted March 17, 2020 DOI: 10.3892/etm.2020.8687 Abstract. Melanogenesis is the process for the production of skin-whitening agents, boosted by markets in Asian countries, melanin, which is the primary cause of human skin pigmenta- especially those in China, India and Japan, is increasing tion. Skin-whitening agents are commercially available for annually (1). Skin color is influenced by a number of intrinsic those who wish to have a lighter skin complexions. To date, factors, including skin types and genetic background, and although numerous natural compounds have been proposed extrinsic factors, including the degree of sunlight exposure to alleviate hyperpigmentation, insufficient attention has and environmental pollution (2-4). Skin color is determined by been focused on potential natural skin-whitening agents and the quantity of melanosomes and their extent of dispersion in their mechanism of action from the perspective of compound the skin (5). Under physiological conditions, pigmentation can classification. In the present article, the synthetic process of protect the skin against harmful UV injury. However, exces- melanogenesis and associated core signaling pathways are sive generation of melanin can result in extensive aesthetic summarized. An overview of the list of natural skin-lightening problems, including melasma, pigmentation of ephelides and agents, along with their compound classifications, is also post‑inflammatory hyperpigmentation (1,6).
    [Show full text]
  • Pharmacokinetic Interactions Between Herbal Medicines and Drugs: Their Mechanisms and Clinical Relevance
    life Review Pharmacokinetic Interactions between Herbal Medicines and Drugs: Their Mechanisms and Clinical Relevance Laura Rombolà 1 , Damiana Scuteri 1,2 , Straface Marilisa 1, Chizuko Watanabe 3, Luigi Antonio Morrone 1, Giacinto Bagetta 1,2,* and Maria Tiziana Corasaniti 4 1 Preclinical and Translational Pharmacology, Department of Pharmacy, Health and Nutritional Sciences, Section of Preclinical and Translational Pharmacology, University of Calabria, 87036 Rende, Italy; [email protected] (L.R.); [email protected] (D.S.); [email protected] (S.M.); [email protected] (L.A.M.) 2 Pharmacotechnology Documentation and Transfer Unit, Preclinical and Translational Pharmacology, Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036 Rende, Italy 3 Department of Physiology and Anatomy, Tohoku Pharmaceutical University, 981-8558 Sendai, Japan; [email protected] 4 School of Hospital Pharmacy, University “Magna Graecia” of Catanzaro and Department of Health Sciences, University “Magna Graecia” of Catanzaro, 88100 Catanzaro, Italy; [email protected] * Correspondence: [email protected]; Tel.: +39-0984-493462 Received: 28 May 2020; Accepted: 30 June 2020; Published: 4 July 2020 Abstract: The therapeutic efficacy of a drug or its unexpected unwanted side effects may depend on the concurrent use of a medicinal plant. In particular, constituents in the medicinal plant extracts may influence drug bioavailability, metabolism and half-life, leading to drug toxicity or failure to obtain a therapeutic response. This narrative review focuses on clinical studies improving knowledge on the ability of selected herbal medicines to influence the pharmacokinetics of co-administered drugs. Moreover, in vitro studies are useful to anticipate potential herbal medicine-drug interactions.
    [Show full text]
  • Nutraceuticals Brian Lockwood
    CjigVXZji^XVah HZXdcYZY^i^dc 7g^VcAdX`lddY 00 Prelim 2/3/07 18:51 Page i Nutraceuticals 00 Prelim 2/3/07 18:51 Page ii 00 Prelim 2/3/07 18:51 Page iii Nutraceuticals A guide for healthcare professionals Second edition Brian Lockwood BPharm, PhD, MRPharmS Senior Lecturer in Pharmacy, School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Manchester, UK London • Chicago 00 Prelim 2/3/07 18:51 Page iv Published by the Pharmaceutical Press An imprint of RPS Publishing 1 Lambeth High Street, London SE1 7JN, UK 100 South Atkinson Road, Suite 200, Grayslake, IL 60030–7820, USA © Pharmaceutical Press 2007 is a trade mark of RPS Publishing RPS Publishing is the publishing organisation of the Royal Pharmaceutical Society of Great Britain First edition published 2002 Second edition published 2007 Typeset by Type Study, Scarborough, North Yorkshire Printed in Great Britain by TJ International, Padstow, Cornwall ISBN 978 0 85369 659 9 All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, without the prior written permission of the copyright holder. The publisher makes no representation, express or implied, with regard to the accuracy of the information contained in this book and cannot accept any legal responsibility or liability for any errors or omissions that may be made. The right of Brian Lockwood to be identified as the author of this work has been asserted by him in accordance with sections 77 and 78 and subject to section 79(6) of the Copyright, Designs and Patents Act, 1988.
    [Show full text]
  • Memorandum Date: June 6, 2014
    DEPARTMENT OF HEALTH & HUMAN SERVICES Public Health Service Food and Drug Administration Memorandum Date: June 6, 2014 From: Bisphenol A (BPA) Joint Emerging Science Working Group Smita Baid Abraham, M.D. ∂, M. M. Cecilia Aguila, D.V.M. ⌂, Steven Anderson, Ph.D., M.P.P.€* , Jason Aungst, Ph.D.£*, John Bowyer, Ph.D. ∞, Ronald P Brown, M.S., D.A.B.T.¥, Karim A. Calis, Pharm.D., M.P.H. ∂, Luísa Camacho, Ph.D. ∞, Jamie Carpenter, Ph.D.¥, William H. Chong, M.D. ∂, Chrissy J Cochran, Ph.D.¥, Barry Delclos, Ph.D.∞, Daniel Doerge, Ph.D.∞, Dongyi (Tony) Du, M.D., Ph.D. ¥, Sherry Ferguson, Ph.D.∞, Jeffrey Fisher, Ph.D.∞, Suzanne Fitzpatrick, Ph.D. D.A.B.T. £, Qian Graves, Ph.D.£, Yan Gu, Ph.D.£, Ji Guo, Ph.D.¥, Deborah Hansen, Ph.D. ∞, Laura Hungerford, D.V.M., Ph.D.⌂, Nathan S Ivey, Ph.D. ¥, Abigail C Jacobs, Ph.D.∂, Elizabeth Katz, Ph.D. ¥, Hyon Kwon, Pharm.D. ∂, Ifthekar Mahmood, Ph.D. ∂, Leslie McKinney, Ph.D.∂, Robert Mitkus, Ph.D., D.A.B.T.€, Gregory Noonan, Ph.D. £, Allison O’Neill, M.A. ¥, Penelope Rice, Ph.D., D.A.B.T. £, Mary Shackelford, Ph.D. £, Evi Struble, Ph.D.€, Yelizaveta Torosyan, Ph.D. ¥, Beverly Wolpert, Ph.D.£, Hong Yang, Ph.D.€, Lisa B Yanoff, M.D.∂ *Co-Chair, € Center for Biologics Evaluation & Research, £ Center for Food Safety and Applied Nutrition, ∂ Center for Drug Evaluation and Research, ¥ Center for Devices and Radiological Health, ∞ National Center for Toxicological Research, ⌂ Center for Veterinary Medicine Subject: 2014 Updated Review of Literature and Data on Bisphenol A (CAS RN 80-05-7) To: FDA Chemical and Environmental Science Council (CESC) Office of the Commissioner Attn: Stephen M.
    [Show full text]
  • Absorption of Dietary Licorice Isoflavan Glabridin to Blood Circulation in Rats
    J Nutr Sci Vitaminol, 53, 358–365, 2007 Absorption of Dietary Licorice Isoflavan Glabridin to Blood Circulation in Rats Chinatsu ITO1, Naomi OI1, Takashi HASHIMOTO1, Hideo NAKABAYASHI1, Fumiki AOKI2, Yuji TOMINAGA3, Shinichi YOKOTA3, Kazunori HOSOE4 and Kazuki KANAZAWA1,* 1Laboratory of Food and Nutritional Chemistry, Graduate School of Agriculture, Kobe University, Rokkodai, Nada-ku, Kobe 657–8501, Japan 2Functional Food Ingredients Division, Kaneka Corporation, 3–2–4 Nakanoshima, Kita-ku, Osaka 530–8288, Japan 3Functional Food Ingredients Division, and 4Life Science Research Laboratories, Life Science RD Center Kaneka Corporation, 18 Miyamae-machi, Takasago, Hyogo 676–8688, Japan (Received February 19, 2007) Summary Bioavailability of glabridin was elucidated to show that this compound is one of the active components in the traditional medicine licorice. Using a model of intestinal absorption, Caco-2 cell monolayer, incorporation of glabridin was examined. Glabridin was easily incorporated into the cells and released to the basolateral side at a permeability coef- ficient of 1.70Ϯ0.16 cm/sϫ105. The released glabridin was the aglycone form and not a conjugated form. Then, 10 mg (30 ␮mol)/kg body weight of standard chemical glabridin and licorice flavonoid oil (LFO) containing 10 mg/kg body weight of glabridin were adminis- tered orally to rats, and the blood concentrations of glabridin was determined. Glabridin showed a maximum concentration 1 h after the dose, of 87 nmol/L for standard glabridin and 145 nmol/L for LFO glabridin, and decreased gradually over 24 h after the dose. The level of incorporation into the liver was about 0.43% of the dosed amount 2 h after the dose.
    [Show full text]
  • Influence of Licorice Root Feeding on Chemical-Nutritional Quality of Cow
    animals Article Influence of Licorice Root Feeding on Chemical-Nutritional Quality of Cow Milk and Stracciata Cheese, an Italian Traditional Fresh Dairy Product 1, 2, 1 3 1 Francesca Bennato y , Andrea Ianni y , Denise Innosa , Camillo Martino , Lisa Grotta , Francesco Pomilio 4, Micaela Verna 1 and Giuseppe Martino 1,* 1 Faculty of BioScience and Technology for Food, Agriculture and Environment, University of Teramo, Via Renato Balzarini 1, 64100 Teramo (TE), Italy; [email protected] (F.B.); [email protected] (D.I.); [email protected] (L.G.); [email protected] (M.V.) 2 Department of Medical, Oral and Biotechnological Sciences, “G. d’Annunzio” University Chieti-Pescara, Via dei Vestini 31, 66100 Chieti, Italy; [email protected] 3 Specialist Diagnostic Department, Istituto Zooprofilattico Sperimentale dell’Abruzzo e del Molise “G. Caporale” Via Campo Boario, 64100 Teramo (TE), Italy; [email protected] 4 Food Hygiene Unit, NRL for L. monocytogenes, Istituto Zooprofilattico Sperimentale dell’Abruzzo e del Molise “G. Caporale” Via Campo Boario, 64100 Teramo (TE), Italy; [email protected] * Correspondence: [email protected]; Tel.: +39-0861-266950 Francesca Bennato and Andrea Ianni equally contributed to this work. y Received: 20 November 2019; Accepted: 12 December 2019; Published: 16 December 2019 Simple Summary: The aim of this study was to investigate the effects of dietary licorice root supplementation on chemical and nutritional characteristics of cow milk and Stracciata cheese, an Italian traditional fresh dairy product. Our results suggest a positive role of licorice in improving the nutritional and organoleptic properties of dairy cow products, influencing various parameters such as fatty acid and volatile profiles.
    [Show full text]
  • Enzyme-Site Blocking Combined with Optimization of Molecular Docking for Efficient Discovery of Potential Tyrosinase Specific In
    molecules Article Enzyme-Site Blocking Combined with Optimization of Molecular Docking for Efficient Discovery of Potential Tyrosinase Specific Inhibitors from Puerariae lobatae Radix Haichun Liu 1,2,†, Yitian Zhu 1,† , Ting Wang 1, Jin Qi 1,* and Xuming Liu 3,* 1 Jiangsu key Laboratory of TCM Evaluation and Translational Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, China; [email protected] (H.L.); [email protected] (Y.Z.); [email protected] (T.W.) 2 School of Science, China Pharmaceutical University, Nanjing 211198, China 3 School of Life Science and Technology, China Pharmaceutical University, Nanjing 211198, China * Correspondence: [email protected] (J.Q.); [email protected] (X.L.); Tel.: +86-025-8618-5157 (J.Q.); +86-025-8618-5397 (X.L.) † These authors contributed equally to this work. Received: 1 August 2018; Accepted: 7 October 2018; Published: 11 October 2018 Abstract: Enzyme inhibitors from natural products are becoming an attractive target for drug discovery and development; however, separating enzyme inhibitors from natural-product extracts is highly complex. In this study, we developed a strategy based on tyrosinase-site blocking ultrafiltration integrated with HPLC-QTOF-MS/MS and optimized molecular docking to screen tyrosinase inhibitors from Puerariae lobatae Radix extract. Under optimized ultrafiltration parameters, we previously used kojic acid, a known tyrosinase inhibitor, to block the tyrosinase active site in order to eliminate false-positive results. Using this strategy, puerarin, mirificin, daidzin and genistinc were successfully identified as potential ligands, and after systematic evaluation by several docking programs, the rank of the identified compounds predicted by computational docking was puerarin > mirificin > kojic acid > daidzin ≈ genistin, which agreed with the results of tyrosinase-inhibition assays.
    [Show full text]
  • Transcriptome Analysis of Pueraria Candollei Var
    Suntichaikamolkul et al. BMC Plant Biology (2019) 19:581 https://doi.org/10.1186/s12870-019-2205-0 RESEARCH ARTICLE Open Access Transcriptome analysis of Pueraria candollei var. mirifica for gene discovery in the biosyntheses of isoflavones and miroestrol Nithiwat Suntichaikamolkul1, Kittitya Tantisuwanichkul1, Pinidphon Prombutara2, Khwanlada Kobtrakul3, Julie Zumsteg4, Siriporn Wannachart5, Hubert Schaller4, Mami Yamazaki6, Kazuki Saito6, Wanchai De-eknamkul7, Sornkanok Vimolmangkang7 and Supaart Sirikantaramas1,2* Abstract Background: Pueraria candollei var. mirifica, a Thai medicinal plant used traditionally as a rejuvenating herb, is known as a rich source of phytoestrogens, including isoflavonoids and the highly estrogenic miroestrol and deoxymiroestrol. Although these active constituents in P. candollei var. mirifica have been known for some time, actual knowledge regarding their biosynthetic genes remains unknown. Results: Miroestrol biosynthesis was reconsidered and the most plausible mechanism starting from the isoflavonoid daidzein was proposed. A de novo transcriptome analysis was conducted using combined P. candollei var. mirifica tissues of young leaves, mature leaves, tuberous cortices, and cortex-excised tubers. A total of 166,923 contigs was assembled for functional annotation using protein databases and as a library for identification of genes that are potentially involved in the biosynthesis of isoflavonoids and miroestrol. Twenty-one differentially expressed genes from four separate libraries were identified as candidates involved in these biosynthetic pathways, and their respective expressions were validated by quantitative real-time reverse transcription polymerase chain reaction. Notably, isoflavonoid and miroestrol profiling generated by LC-MS/MS was positively correlated with expression levels of isoflavonoid biosynthetic genes across the four types of tissues. Moreover, we identified R2R3 MYB transcription factors that may be involved in the regulation of isoflavonoid biosynthesis in P.
    [Show full text]
  • 10/12/2019 Herbal Preparations with Phytoestrogens- Overview of The
    Herbal preparations with phytoestrogens- overview of the adverse drug reactions Introduction For women suffering from menopausal symptoms, treatment is available if the symptoms are particularly troublesome. The main treatment for menopausal symptoms is hormone replacement therapy (HRT), although other treatments are also available for some of the symptoms (1). In recent years, the percentage of women taking hormone replacement therapy has dropped (2, 3). Many women with menopausal symptoms choose to use dietary supplements on a plant-based basis, probably because they consider these preparations to be "safe" (4). In addition to product for relief of menopausal symptoms, there are also preparations on the market that claim to firm and grow the breasts by stimulating the glandular tissue in the breasts (5). All these products contain substances with an estrogenic activity, also called phytoestrogens. These substances are found in a variety of plants (4). In addition, also various multivitamin preparations are on the market that, beside the vitamins and minerals, also contain isoflavonoids. Because those are mostly not specified and present in small quantities and no estrogenic effect is to be expected, they are not included in this overview. In 2015 and 2017 the Netherlands Pharmacovigilance Centre Lareb informed the Netherlands Food and Consumer Product Safety Authority (NVWA) about the received reports of Post-Menopausal Vaginal Hemorrhage Related to the Use of a Hop-Containing Phytotherapeutic Products MenoCool® and Menohop® (6, 7). Reports From September 1999 until November 2019 the Netherlands Pharmacovigilance Centre Lareb received 51 reports of the use of phytoestrogen containing preparations (see Appendix 1). The reports concern products with various herbs to which an estrogenic effect is attributed.
    [Show full text]
  • Characterization of the Inhibition of Genistein
    CHARACTERIZATION OF THE INHIBITION OF GENISTEIN GLUCURONIDATION BY BISPHENOL A IN HUMAN AND RAT LIVER MICROSOMES By JANIS LAURA COUGHLIN A thesis submitted to the Graduate School-New Brunswick Rutgers, The State University of New Jersey and The Graduate School of Biomedical Sciences University of Medicine and Dentistry of New Jersey in partial fulfillment of the requirements for the degree of Master of Science Joint Graduate Program in Toxicology written under the direction of Dr. Brian Buckley and approved by __________________________________ __________________________________ __________________________________ __________________________________ New Brunswick, New Jersey OCTOBER 2011 ABSTRACT OF THE THESIS Characterization of the Inhibition of Genistein Glucuronidation by Bisphenol A in Human and Rat Liver Microsomes By JANIS LAURA COUGHLIN Thesis Director: Dr. Brian Buckley Genistein is a natural phytoestrogen that is found abundantly in the soybean. Bisphenol A (BPA) is a synthetic chemical used in the synthesis of polycarbonate plastics and epoxy resins. Endocrine disrupting properties of both genistein and BPA have been well established by various laboratories. Because the adverse biological effects caused by genistein and BPA are similar, and may include common co-exposure scenarios in the general population such as in the consumption of a soy-milk latte from a polycarbonate plastic coffee mug, analysis of the perturbation of the metabolism via glucuronidation of genistein in the presence of BPA has been assessed. Human and rat liver microsomes were exposed to varying doses of genistein (0 to 250 μM) in the absence (0 μM) or presence (25 μM) of BPA. Treatment with 25 μM BPA caused non-competitive inhibition of the glucuronidation of genistein in human liver microsomes with a Ki value of 58.7 μM, represented by a decrease in Vmax from 0.93 ± 0.10 nmol/min/mg in the ii absence of BPA to 0.62 ± 0.05 nmol/min/mg in the presence of BPA, and a negligible change in Km values between treatment groups.
    [Show full text]
  • In Vitro Study of Flavonoids, Fatty Acids, and Steroids on Proliferation of Rat Hepatic Stellate Cells Farid A
    In vitro Study of Flavonoids, Fatty Acids, and Steroids on Proliferation of Rat Hepatic Stellate Cells Farid A. Badriaa,*, Abdel-Aziz A. Dawidarb, Wael E. Houssena, and Wayne T. Shierc a Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt. E-mail: [email protected] b Chemistry Department, Faculty of Sciences, Mansoura University, Mansoura 35516 Egypt c Medicinal Chemistry Department, College of Pharmacy, University of Minnesota, Minne- apolis MN 55455 USA * Author for correspondence and reprint requests Z. Naturforsch. 60c, 139Ð142 (2005); received November 9/December 8, 2004 There is a wealth of evidence that hepatic stellate cells (HSCs) orchestrate most of the important events in liver fibrogenesis. After liver injury, HSCs become activated to a profi- brogenic myofibroblastic phenotype and can regulate net deposition of collagens and other matrix proteins in the liver. The proliferation of HSCs is mainly stimulated by the platelet- derived growth factor (PDGF). In this study, some compounds from natural resources have been tested for their activity to inhibit PDGF-driven proliferative activity of rat HSCs. Api- genin, quercetin, genistein, daidzin, and biochanin A exhibited > 75% inhibitory activity against HSC-T6. It was found that, γ-linolenic (γ-Ln), eicosapentanoic (EPA) and α- linolenic (α-Ln) acids showed a high inhibitory effect on proliferation of rat HSCs at 50 nmol/l. Cholest-4-ene-3,6-dione and stigmastone-4-en-3,6-dione are the most active steroids with in- hibitory activities > 80% and this is most likely due to the presence of the 4-en-3,6-dione moiety in both compounds.
    [Show full text]