DOCSLIB.ORG

Phytoserms in Licorice

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Phytoserms in Licorice University of Mississippi eGrove Electronic Theses and Dissertations Graduate School 1-1-2019 Cheminformatic Approach for Deconvolution of Active Compounds in a Complex Mixture - phytoserms in Licorice Manal Mohammad Alhusban Follow this and additional works at: https://egrove.olemiss.edu/etd Part of the Pharmacy and Pharmaceutical Sciences Commons Recommended Citation Alhusban, Manal Mohammad, "Cheminformatic Approach for Deconvolution of Active Compounds in a Complex Mixture - phytoserms in Licorice" (2019). Electronic Theses and Dissertations. 1954. https://egrove.olemiss.edu/etd/1954 This Dissertation is brought to you for free and open access by the Graduate School at eGrove. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of eGrove. For more information, please contact [email protected]. CHEMINFORMATIC APPROACH FOR DECONVOLUTION OF ACTIVE COMPOUNDS IN A COMPLEX MIXTURE - PHYTOSERMS IN LICORICE A Dissertation Presented in partial fulfillment of requirements for the degree of Doctor of Philosophy in Pharmaceutical Sciences, Emphasis in Pharmacognosy The University of Mississippi Manal M. Alhusban August 2019 Copyright © 2019 by Manal M. Alhusban All rights reserved ABSTRACT The genus Glycyrrhiza, encompasses several species exhibiting complex structural diversity of secondary metabolites and hence biological activities. The intricate nature of botanical remedies, such as licorice, rendered them obsolete for scientific research or medical industry. Understanding and finding the mechanisms of efficacy or safety for a plant-based therapy is very challenging, yet it remains crucial and warranted. The licorice plant is known to have Selective Estrogen Receptor Modulatory effects (SERMs), with a spectrum of estrogenic and anti-estrogenic activities attributed to women’s health. On the contrary, licorice extract was shown to induce pregnane xenobiotic receptor (PXR), which may manifest as a potential route for deleterious effects such as herb-drug interaction (HDI). While many studies attributed these divergent activities to a few classes of compounds such as liquiritigenin (a weak estrogenic SERM) or glycyrrhizin (weak PXR agonist), no attempt was made to characterize the complete set of compounds responsible for these divergent activities. A plethora of licorice components is undermined, which might have the potential to be developed into novel phytoSERMS or to trigger undesirable adverse effects by altering drug metabolizing enzymes and thus pharmacokinetics. In this work, we explored the mechanism associated with the efficacy and safety of components reported in the licorice plant. We utilized smart screening techniques such as cheminformatics tools to reveal the high number of secondary metabolites produced by licorice, which are capable of interfering with the human Estrogen Receptors (hERs) and/or PXR or other ii vital cytochrome P450 enzymes. After the validation of our in silico models by using the previous knowledge in this area, the alerting phytochemicals from two Glycyrrhiza species (G. glabra and G. uralensis) were clustered. Exhaustive computational mining of licorice metabolome against selected endocrinal and metabolic targets led to the discovery of a unique class of compounds, which belong to the dihydrostilbenoids (DHS) class appended with prenyl groups at various positions. To the best of our knowledge, this interesting group of compounds has not been studied for their estrogenic activities or PXR activation. In addition, some of the bis-prenylated DHS have been reported to be present only in G. uralensis. Thus, we have ventured to synthesize a set of constitutional isomers of stilbenoids and DHS (archetypal of those found in licorice) with different prenylation patterns. Sixteen constitutional isomers of stilbenoids (M2-M10) and DHS (M12-M18) were successfully synthesized, of which six of them (M8, M9, M14, M15, M17, and M18) are synthesized for the first time to be further tested and validated with cell-based methods for their estrogenic activities. We have unveiled a novel class of compounds, which possess a strong PXR activation. These results, which were in accord with the in silico prediction, were observed for multiple synthesized prenylated stilbenoid and DHS by the luciferase reporter gene assay at µM concentrations. Moreover, this activation was further validated by the six-fold increase in mRNA expression of Cytochrome P450 3A4 (CYP3A4), where three representative compounds (M7, M10, and M15) exceeded the activation fold of the positive control. Another aspect of the current project was to predict the phase I primary metabolites of iii compounds found in both species of Glycyrrhiza and assess them with computational tools to predict their binding potential against both isoforms of hERs or drug metabolizing enzymes such as (CYP) inhibition models. Our investigations revealed estrogenic character for most of the predicted metabolites and have confirmed earlier reports of potential CYP3A4 and CYP1A2 inhibition. Compilation of such data is essential to gain a better understanding of the efficacy/safety of licorice extracts used in various botanical formularies. This approach with the involved cheminformatic tools has proven effective to yield rich information to support our understanding of traditional practices. It also can expand the role of botanical drugs for introducing new chemical entities (NCEs) and/or uncovering their liabilities at early stages. iv DEDICATION My Mother Fawzeya Who taught me how to dream, imagine and work hard My Father Mohammad Who taught me how to concentrate on the goals, not obstacles My Husband Ali Who taught me that there are no limits except the limits in our minds My Kids Ghaith, Ra’ad and Salma Who suffered with me the most v LIST OF ABBREVIATIONS AND SYMBOLS μL Microliter μM Micromolar AF-2 Active Functional Region 2 AKT Protein Kinase B Al2O3 Alumina CAR Constitutive Androstane Receptor CART Classification and Regression Tree Algorithm CERAPP Collaborative Estrogen Receptor Activity Prediction database CYP3A4 Cytochrome P450 3A4 DBD DNA-Binding Domain DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DCM Dichloromethane DHS Dihydrostilbenoids DMF Dimethylformamide EC50 The concentration at the half maximum efficacy EtOAc Ethyl Acetate EtOH Ethanol US FDA US Food and Drug Administration GST Glutathione S-Transferase vi HDI Herb-Drug Interaction hERs Human Estrogen Receptors Hex Hexanes HMBC Heteronuclear Multiple-Bond Correlation Spectroscopy hrs. Hours LBD Ligand-Binding Domain m/z Mass-to-Charge Ratio MDR1 Phase III P-Glycoprotein or Multidrug Resistance-Associated Protein 1 MEMCl 2-Methoxyethoxymethyl Chloride MeOH Methanol mL Milliliter MOMCl Methoxymethyl Chloride NaH Sodium Hydride nBuLi n-Butyl Lithium NCEs New Chemical Entities NFkβ Nuclear Factor kappa-Light-Chain-Enhancer of Activated B Cells NOESY Nuclear Overhauser Effect Spectroscopy NMR Nuclear Magnetic Resonance NR1I2 Nuclear Receptor Subfamily 1 Group I OATP2 Organic Anion Transporting Polypeptide 2 vii OCHEM Online Chemical Environment PDB Protein Data Bank PXR Pregnane Xenobiotic Receptor phytoSERMs Phytochemicals that act as Selective Estrogen Receptor Modulators QSAR Quantitative Structure-Activity Relationships RBA Relative Binding Affinity RMSD Root-Mean-Square Deviation r.t. Room Temperature SDF Spatial Data Files SERMs Selective Estrogen Receptor Modulators Sult Sulfotransferases TEA Triethyl Amine THF Tetrahydrofuran TLC Thin Layer Chromatography UGTs Uridine Diphosphate (UDP)-Glucuronosyltransferases VDR Vitamin D Receptor VEGA Virtual Models for Property Evaluation of Chemicals Within a Global Architecture viii ACKNOWLEDGMENTS I would like to express my deep gratitude for all the people who helped and supported me throughout my Ph.D. at Ole Miss. Special thanks for my advisor Dr. Ikhlas Khan, who accepted me as a member of his group and supported me and my family. He was always cautious to offer us the best environment to learn and succeed. The guidance, supervision, honesty and critique of Dr. Amar Chittiboyina, my co-advisor, and mentor made me a better scientist. His passion for exploration and discovery is contagious. Although he had a tight schedule, he never skipped a chance for discussion and explanation. When things become impossible in the lab, he would always come and teach us how to troubleshoot. I will always be grateful for him, for his concern to give me the opportunity to engage in diverse projects and for his constant encouragement, kindness, and inspiration. I would also express my sincere thanks to Dr. Robert Doerksen, for his candid lectures and training, help, and guidance throughout the years. I am greatly indebted to him for his relentless support, mentoring and critiques, which greatly affected my academic development. I would like to thank Dr. Samir Ross for his support, advice, and kindness. To Dr. Cole Stevens for his support, effort and time for revising my ORP and dissertation. My special thanks for to Dr. John Rimoldi and Dr. Daneel Ferreira for their great lectures. I am also thankful to all the people in NCNPR who supported me, especially, Dr. Junaid Rehman, I will always be grateful for him and his family for their continuous support and help for my family. For Dr. Ali Zulfiqar, for making NMR easily understandable. I would also thank ix Dr. Shabana Khan, Dr. Jon Parcher, Dr. Bharathi Avula, and Dr. Yan-Hong Wang for their collaboration and advice, and for the post docs who trained me well in the labs, Dr.
Load more

Recommended publications
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Lyme Disease (Chronic)
    Dr.
    [Show full text]
  • Biologically Active Molecules from Soybeans
    10 Biologically Active Molecules from Soybeans Michio Kurosu Department of Pharmaceutical Sciences, University of Tennessee Health Science Center USA 1. Introduction Soybeans (Glycine max [L.] Merr.) contain an impressive array of biologically active components. People have been eating soybeans for almost 5,000 years. Unlike most plant foods, soybeans are high in protein. Researchers are interested in both the nutritional value and the potential health benefits of soybeans. Research of the health effects of soyfoods and soybean constituents has been received significant attention to support the health improvements or health risks observed clinically or in vitro experiments. This research includes a wide range of areas, such as cancer, coronary heart disease (cardiovascular disease), osteoporosis, cognitive function (memory related), menopausal symptoms, renal function, and many others. This chapter provides up-to-date coverage on biologically active and related organic molecules isolated from soy and soy products. Their biological activities are briefly summarized. Molecules discussed in this chapter are as follows: isoflavones, phytic acid, soy lipids, soy phytoalexins, soyasaponins, lectins, hemagglutinin, soy toxins, and vitamins. 2. Health benefit of soy or soy products Soy products have been considered as great source of protein for many decades. Japanese, in particular, eat a soy-based diet. Japanese monks eat soy products as their main protein source. They are known to live longer and have lower rates of chronic diseases. Because soybeans contain practically no starch, soybeans are an important part of a diabetic diet. Soybeans are 1) rich in protein (vide supra), calcium, and vitamins, and 2) high in mono- saturated fatty acids. In addition, soybeans contain several biologically interesting phytochemicals as minor components, which scientists are interested in understanding their biological functions.
    [Show full text]
  • Metabolomics and Transcriptomics Identify Multiple Downstream Targets of Paraburkholderia Phymatum Σ54 During Symbiosis with Phaseolus Vulgaris
    Research Collection Journal Article Metabolomics and Transcriptomics Identify Multiple Downstream Targets of Paraburkholderia phymatum σ54 During Symbiosis with Phaseolus vulgaris Author(s): Lardi, Martina; Liu, Yilei; Giudice, Gaetano; Ahrens, Christian H.; Zamboni, Nicola; Pessi, Gabriella Publication Date: 2018-04 Permanent Link: https://doi.org/10.3929/ethz-b-000258158 Originally published in: International Journal of Molecular Sciences 19(4), http://doi.org/10.3390/ijms19041049 Rights / License: Creative Commons Attribution 4.0 International This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library International Journal of Molecular Sciences Article Metabolomics and Transcriptomics Identify Multiple Downstream Targets of Paraburkholderia phymatum σ54 During Symbiosis with Phaseolus vulgaris Martina Lardi 1, Yilei Liu 1, Gaetano Giudice 1, Christian H. Ahrens 2, Nicola Zamboni 3 and Gabriella Pessi 1,* ID 1 Department of Plant and Microbial Biology, University of Zurich, CH-8057 Zurich, Switzerland; [email protected] (M.L.); [email protected] (Y.L.); [email protected] (G.G.) 2 Agroscope, Research Group Molecular Diagnostics, Genomics and Bioinformatics & Swiss Institute of Bioinformatics (SIB), CH-8820 Wädenswil, Switzerland; [email protected] 3 Institute of Molecular Systems Biology, ETH Zurich, CH-8093 Zurich, Switzerland; [email protected] * Correspondence: [email protected]; Tel.: +41-44-6352904 Received: 28 February 2018; Accepted: 28 March 2018; Published: 1 April 2018 Abstract: RpoN (or σ54) is the key sigma factor for the regulation of transcription of nitrogen fixation genes in diazotrophic bacteria, which include α- and β-rhizobia.
    [Show full text]
  • Biochanin a Promotes Proliferation That Involves a Feedback Loop of Microrna-375 and Estrogen Receptor Alpha in Breast Cancer Cells
    Cellular Physiology Cell Physiol Biochem 2015;35:639-646 DOI: 10.1159/000369725 © 2015 S. Karger AG, Basel and Biochemistry Published online: January 28, 2015 www.karger.com/cpb 639 Accepted:Chen et al.: December Biochanin 03, A Promotes 2014 Proliferation 1421-9778/15/0352-0639$39.50/0 This is an Open Access article licensed under the terms of the Creative Commons Attribution- NonCommercial 3.0 Unported license (CC BY-NC) (www.karger.com/OA-license), applicable to the online version of the article only. Distribution permitted for non-commercial purposes only. Original Paper Biochanin A Promotes Proliferation that Involves a Feedback Loop of MicroRNA-375 and Estrogen Receptor Alpha in Breast Cancer Cells Jian Chena Bo Geb Yong Wanga Yu Yec Sien Zengd Zhaoquan Huangd aSchool of Basic Medical Sciences, Guilin Medical University, Guilin, bGuilin Medical University, Guilin, cDepartment of Emergency, First Affiliated Hospital of Guangxi Medical University, Nanning, dDepartment of Pathology, Guilin Medical University, Guilin, China Key Words Biochanin A • miR-375 • Estrogen receptor α • OVX Abstract Background: Biochanin A and formononetin are O-methylated isoflavones that are isolated from the root of Astragalus membranaceus, and have antitumorigenic effects. Our previous studies found that formononetin triggered growth-inhibitory and apoptotic activities in MCF-7 breast cancer cells. We performed in vivo and in vitro studies to further investigate the potential effect of biochanin A in promoting cell proliferation in estrogen receptor (ER)- positive cells, and to elucidate underlying mechanisms. Methods: ERα-positive breast cancer cells (T47D, MCF-7) were treated with biochanin A. The MTT assay and flow cytometry were used to assess cell proliferation and apoptosis.
    [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]
  • Thesis of Potentially Sweet Dihydrochalcone Glycosides
    University of Bath PHD The synthesis of potentially sweet dihydrochalcone glycosides. Noble, Christopher Michael Award date: 1974 Awarding institution: University of Bath Link to publication Alternative formats If you require this document in an alternative format, please contact: [email protected] General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Download date: 05. Oct. 2021 THE SYNTHESIS OF POTBTTIALLY SWEET DIHYDROCHALCOITB GLYCOSIDES submitted by CHRISTOPHER MICHAEL NOBLE for the degree of Doctor of Philosophy of the University of Bath. 1974 COPYRIGHT Attention is drawn to the fact that copyright of this thesis rests with its author.This copy of the the­ sis has been supplied on condition that anyone who con­ sults it is understood to recognise that its copyright rests with its author and that no quotation from the thesis and no information derived from it may be pub­ lished without the prior written consent of the author.
    [Show full text]
  • Protection of PC12 Cells Against Superoxide-Induced Damage by Isoflavonoids from Astragalus Mongholicus1
    BIOMEDICAL AND ENVIRONMENTAL SCIENCES 22, 50-54 (2009) www.besjournal.com Protection of PC12 Cells against Superoxide-induced Damage by 1 Isoflavonoids from Astragalus mongholicus ＃ + + ＃,2 DE-HONG YU , YONG-MING BAO , LI-JIA AN , AND MING YANG ＃The State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, China; +Department of Bioscience and Biotechnology, Dalian University of Technology, Dalian 116024, Liaoning, China Objective To further investigate the neuroprotective effects of five isoflavonoids from Astragalus mongholicus on xanthine (XA)/ xanthine oxidase (XO)-induced injury to PC12 cells. Methods PC12 cells were damaged by XA/XO. The activities of antioxidant enzymes, MTT, LDH, and GSH assays were used to evaluate the protection of these five isoflavonoids. Contents of Bcl-2 family proteins were determined with flow cytometry. Results Among the five isoflavonoids including formononetin, ononin, 9, 10-dimethoxypterocarpan-3-O-β-D-glucoside, calycosin and calycosin-7-O-glucoside, calycosin and calycosin-7-O-glucoside were found to inhibit XA/ XO-induced injury to PC12 cells. Their EC50 values of formononetin and calycosin were 0.05 μg/mL. Moreover, treatment with these three isoflavonoids prevented a decrease in the activities of antioxidant enzymes, superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px), while formononetin and calycosin could prevent a significant deletion of GSH. In addition, only calycosin and calycosin-7-O-glucoside were shown to inhibit XO activity in cell-free system, with an approximate IC50 value of 10 μg/mL and 50 μg/mL. Formononetin and calycosin had no significant influence on Bcl-2 or Bax protein contents. Conclusion Neuroprotection of formononetin, calycosin and calycosin-7-O-glucoside may be mediated by increasing endogenous antioxidants, rather by inhibiting XO activities or by scavenging free radicals.
    [Show full text]
  • The Proceedings of the Conference on the Challenges of Contemporary Cell Biology Molecular Genetics, System Biology, Bioinformatics
    University of Lodz The Proceedings of the Conference on The Challenges of Contemporary Cell Biology Molecular Genetics, System Biology, Bioinformatics April 20 – 21, 2009 The Conference to Honor Professor Maria J. Olszewska on Her Jubilee Łódź University Press, 2009 Conference on The Challenges of Contemporary Cell Biology – April 20-21, 2009 Sponsors of the Conference 2 Conference on The Challenges of Contemporary Cell Biology – April 20-21, 2009 Patronage: Rector of the University of Lodz – Professor Włodzimierz Nykiel, Ph.D. Conference supported by Polish Ministry of Science and Higher Education Conference Organizers: The Committee on Cell Biology of Polish Academy of Sciences Institute of Physiology, Cytology, and Cytogenetics, University of Lodz The Lodz Branch of the Polish Academy of Sciences Organizing Committee: Chairman: Andrzej K. Kononowicz – University of Lodz Vice-Chairman: Elżbieta Wyroba – The Committee on Cell Biology of Polish Academy of Sciences Members: Maria Kwiatkowska – University of Lodz Jerzy Kawiak – Editor of Advances in Cell Biology (Postępy Biologii Komórki) Barbara Gabara – University of Lodz Mirosław Godlewski – University of Lodz Jacek Jurczakowski – The Lodz Branch of the Polish Academy of Sciences Kazimierz Marciniak – University of Lodz Janusz Maszewski – University of Lodz Maria Skłodowska – University of Lodz Scientific Committee: Maria Kwiatkowska – University of Lodz Jerzy Kawiak – Editor of Advances in Cell Biology (Postępy Biologii Komórki) Andrzej K. Kononowicz – University of Lodz Janusz Maszewski – University of Lodz Conference Office: Ewa Mikołajczyk-Zając – University of Lodz Violetta Macioszek – University of Lodz Katarzyna Hnatuszko-Konka – University of Lodz (Book cover and Conference website design) Tomasz Kowalczyk – University of Lodz Department of Genetics and Plant Molecular Biology and Biotechnology Faculty of Biology and Environmental Protection University of Lodz S.
    [Show full text]
  • Treatment Protocol Copyright © 2018 Kostoff Et Al
    Prevention and reversal of Alzheimer's disease: treatment protocol Copyright © 2018 Kostoff et al PREVENTION AND REVERSAL OF ALZHEIMER'S DISEASE: TREATMENT PROTOCOL by Ronald N. Kostoffa, Alan L. Porterb, Henry. A. Buchtelc (a) Research Affiliate, School of Public Policy, Georgia Institute of Technology, USA (b) Professor Emeritus, School of Public Policy, Georgia Institute of Technology, USA (c) Associate Professor, Department of Psychiatry, University of Michigan, USA KEYWORDS Alzheimer's Disease; Dementia; Text Mining; Literature-Based Discovery; Information Technology; Treatments Prevention and reversal of Alzheimer's disease: treatment protocol Copyright © 2018 Kostoff et al CITATION TO MONOGRAPH Kostoff RN, Porter AL, Buchtel HA. Prevention and reversal of Alzheimer's disease: treatment protocol. Georgia Institute of Technology. 2018. PDF. https://smartech.gatech.edu/handle/1853/59311 COPYRIGHT AND CREATIVE COMMONS LICENSE COPYRIGHT Copyright © 2018 by Ronald N. Kostoff, Alan L. Porter, Henry A. Buchtel Printed in the United States of America; First Printing, 2018 CREATIVE COMMONS LICENSE This work can be copied and redistributed in any medium or format provided that credit is given to the original author. For more details on the CC BY license, see: http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License<http://creativecommons.org/licenses/by/4.0/>. DISCLAIMERS The views in this monograph are solely those of the authors, and do not represent the views of the Georgia Institute of Technology or the University of Michigan. This monograph is not intended as a substitute for the medical advice of physicians. The reader should regularly consult a physician in matters relating to his/her health and particularly with respect to any symptoms that may require diagnosis or medical attention.
    [Show full text]
  • Flavonoids and Flavan-3-Ol from Aerial Part of Agrimonia Pilosa LEDEB
    Journal of Multidisciplinary Engineering Science and Technology (JMEST) ISSN: 2458-9403 Vol. 4 Issue 10, October - 2017 Flavonoids and flavan-3-ol from aerial part of Agrimonia pilosa LEDEB. Hoang Le Tuan Anh Nguyen Van Linh Mientrung Institute for Scientific Research Military Institute of Traditional Medicine Vietnam Academy of Science and Technology 442 Kim Giang, Hoang Mai, Hanoi, Vietnam 321 Huynh Thuc Khang, Hue City [email protected] [email protected] Abstract—Using various chromatography mesh, Merck) or RP-18 resins (30-50 µm, Fujisilisa methods, three flavonoids, quercetin-3-O- Chemical Ltd.). Thin layer chromatography (TLC) was rutinoside (1), quercetin-3-O-β-D- performed using pre-coated silica gel 60 F254 (0.25 galactopyranoside (2), quercetin (3), and a flavan- mm, Merck) and RP-18 F254S plates (0.25 mm, Merck). 3-ol, catechin (4) were isolated from methanol Spots were visualized under UV radiation (254 and extract of Agrimonia pilosa. Their structures were 365 nm) and sprayed with aqueous solution of H2SO4 elucidated by 1D- and 2D-NMR spectroscopic (10%), heating with a heat gun. analyses and comparison with those reported in B. Plant materials the literature. Compound 2 was reported from A. pilosa for the first time. The aerial parts of A. pilosa were collected at Trung Khanh, Cao Bang province, Vietnam in August 2013. Keywords—Agrimonia pilosa; flavonoid; Its scientific name was identified by Dr. Pham Thanh quercetin-3-O-β-D-galactopyranoside; quercetin Huyen, Institute of Ecology and Biological Resources, derivatives. VAST. A voucher specimen (6695A) is deposited at I. INTRODUCTION the Herbarium of Military Institute of Traditional Medicine.
    [Show full text]
  • Light and Temperature Conditions Affect Bioflavonoid Accumulation In
    Plant Cell Tiss Organ Cult DOI 10.1007/s11240-014-0502-8 RESEARCH NOTE Light and temperature conditions affect bioflavonoid accumulation in callus cultures of Cyclopia subternata Vogel (honeybush) Adam Kokotkiewicz • Adam Bucinski • Maria Luczkiewicz Received: 20 March 2014 / Accepted: 26 April 2014 Ó The Author(s) 2014. This article is published with open access at Springerlink.com Abstract Callus cultures of the endemic South-African maintained at 24 °C. On the contrary, elevated temperature legume Cyclopia subternata were cultivated under varying (29 °C) applied during the second half of the culture period light and temperature conditions to determine their influ- resulted in over 300 and 500 % increase in CG and PG ence on biomass growth and bioflavonoids accumulation. content (61.76 and 58.89 mg 100 g-1, respectively) while Experimental modifications of light included complete maintaining relatively high biomass yield. darkness, light of different spectral quality (white, red, blue and yellow) and ultraviolet C (UVC) irradiation. The calli Keywords Hesperidin Á In vitro cultures Á Isoflavones Á were also subjected to elevated temperature or cold stress. Light spectral quality Á Temperature regime Á UVC Among the tested light regimes, cultivation under blue irradiation light resulted in the highest levels of hesperidin (H)— 118.00 mg 100 g-1 dry weight (DW) on 28 days of Abbreviations experiment, as well as isoflavones: 7-O-b-glucosides of CG Calycosin 7-O-b-glucoside calycosin (CG), pseudobaptigenin (PG) and formononetin 4-CPPU N-(2-chloro-4-pyridyl)-N0-phenylurea (FG)—28.74, 19.26 and 10.32 mg 100 g-1 DW, respec- (forchlorfenuron) tively, in 14-days old calli.
    [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]