SAR, QSAR and Docking of Anticancer Flavonoids and Variants: a Review
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Antimicrobial Activity of Flavonoids and Steroids Isolated from Two Chromolaena Species
Revista Brasileira de Ciências Farmacêuticas Brazilian Journal of Pharmaceutical Sciences vol. 39, n. 4, out./dez., 2003 Antimicrobial activity of flavonoids and steroids isolated from two Chromolaena species Silvia Helena Taleb-Contini1, Marcos José Salvador1, Evandro Watanabe2, Izabel Yoko Ito2, Dionéia Camilo Rodrigues de Oliveira2* 1Departamento de Química, Faculdade de Filosofia Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 2 Departamentos de Física e Química e de Análises Clínicas, Toxicológicas e Bromatológicas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo The crude extracts (dichloromethanic and ethanolic) and some Unitermos • Chromolaena compounds (8 flavonoids and 5 steroids) isolated from Chromolaena • Asteraceae *Correspondence: squalida (leaves and stems) and Chromolaena hirsuta (leaves and • Flavonoids D. C. R. de Oliveira flowers) have been evaluated against 22 strains of microorganisms • Steroids Departamento de Física e Química Faculdade de Ciências Farmacêuticas including bacteria (Gram-positive and Gram-negative) and yeasts. • Antimicrobial activity de Ribeirão Preto, USP All crude extracts, flavonoids and steroids evaluated have been Av. do Café, s/n 14040-903, Ribeirão Preto - SP, Brasil shown actives, mainly against Gram-positive bacteria. E mail: [email protected] INTRODUCTION Concentration (MIC) in the range of 64 to 250 µg/mL) was showed for crude extract of Castanea sativa. The Flavonoids are phenolic substances widely analyse by TLC and HPLC of the active fraction showed distributed in all vascular plants. They are a group of about the presence of flavonoids rutin, hesperidin, quercetin, 4000 naturally compounds known, and have been shown to apigenin, morin, naringin, galangin and kaempferol. have contribute to human health through our daily diet. -
Candidate Gene Identification from the Wheat QTL-2DL for Resistance Against Fusarium Head Blight Based on Metabolo-Genomics Approach
Candidate gene identification from the wheat QTL-2DL for resistance against Fusarium head blight based on metabolo-genomics approach Udaykumar Kage Department of Plant Science McGill University, Montreal, Canada August 2016 A thesis submitted to the McGill University in partial fulfillment of the requirements of the degree of Doctor of Philosophy ©Udaykumar Kage (2016) i Dedicated to my beloved parents ii TABLE OF CONTENTS TABLE OF CONTENTS………………………………………………………………………...iii LIST OF TABLES……………………………………………………………………………...viii LIST OF FIGURES………………………………………………………………………………ix LIST OF APPENDICES…………………………………………………………………………xv LIST OF ABBREVIATIONS…………………………………………………………………...xvi ABSTRACT…………………………………………………………………………………...xviii ACKNOWLEDGEMENT……………………………………………………………………...xxi PREFACE AND CONTRIBUTION OF THE AUTHORS……………………………………..01 PREFACE……………………………………………………………………………………......01 CONTRIBUTION OF THE AUTHORS………………………………………………………...02 CHAPTER I: GENERAL INTRODUCTION…………………………………………………...03 GENERAL HYPOTHESIS……………………………………………………………………...07 GENERAL OBJECTIVES……………………………………………………………………....07 CHAPTER II: REVIEW OF THE LITERATURE……………………………………………...08 2.1 Fusarium head blight of wheat at a glance…………………………………………………...08 2.1.1 Fusarium head blight epidemiology and impact on wheat production…………………08 2.1.2 FHB management practices ……………………………………………………….……10 2.1.3 FHB management through breeding for disease resistance…………………………….11 2.1.3.1 Types of Fusarium head blight resistance………………………………………….12 2.1.3.2 Molecular markers and QTL for FHB resistance……………………………….…13 -
Antibiotic Additive and Synergistic Action of Rutin, Morin and Quercetin Against Methicillin Resistant Staphylococcus Aureus
Amin et al. BMC Complementary and Alternative Medicine (2015) 15:59 DOI 10.1186/s12906-015-0580-0 RESEARCH ARTICLE Open Access Antibiotic additive and synergistic action of rutin, morin and quercetin against methicillin resistant Staphylococcus aureus Muhammad Usman Amin1†, Muhammad Khurram2*†, Baharullah Khattak1† and Jafar Khan1† Abstract Background: To determine the effect of flavonoids in conjunction with antibiotics in methicillin resistant Staphylococcus aureus (MRSA) a study was designed. The flavonoids included Rutin, Morin, Qurecetin while antibiotics included ampicillin, amoxicillin, cefixime, ceftriaxone, vancomycin, methicillin, cephradine, erythromycin, imipenem, sulphamethoxazole/trimethoprim, ciprofloxacin and levolfloxacin. Test antibiotics were mostly found resistant with only Imipenem and Erythromycin found to be sensitive against 100 MRSA clinical isolates and S. aureus (ATCC 43300). The flavonoids were tested alone and also in different combinations with selected antibiotics. Methods: Antibiotics and flavonoids sensitivity assays were carried using disk diffusion method. The combinations found to be effective were sifted through MIC assays by broth macro dilution method. Exact MICs were determined using an incremental increase approach. Fractional inhibitory concentration indices (FICI) were determined to evaluate relationship between antibiotics and flavonoids is synergistic or additive. Potassium release was measured to determine the effect of antibiotic-flavonoids combinations on the cytoplasmic membrane of test bacteria. Results: Antibiotic and flavonoids screening assays indicated activity of flavanoids against test bacteria. The inhibitory zones increased when test flavonoids were combined with antibiotics facing resistance. MICs of test antibiotics and flavonoids reduced when they were combined. Quercetin was the most effective flavonoid (MIC 260 μg/ml) while morin + rutin + quercetin combination proved most efficient with MIC of 280 + 280 + 140 μg/ml. -
Neuroprotective Effect of Fisetin Through Suppression of IL-1R/TLR Axis and Apoptosis in Pentylenetetrazole-Induced Kindling in Mice
ORIGINAL RESEARCH published: 21 July 2021 doi: 10.3389/fneur.2021.689069 Neuroprotective Effect of Fisetin Through Suppression of IL-1R/TLR Axis and Apoptosis in Pentylenetetrazole-Induced Kindling in Mice Saima Khatoon 1, Nidhi Bharal Agarwal 2*, Mohammed Samim 3 and Ozair Alam 4 1 Department of Medical Elementology and Toxicology, School of Chemical and Life Sciences, Jamia Hamdard, New Delhi, India, 2 Centre for Translational and Clinical Research, School of Chemical and Life Sciences, Jamia Hamdard, New Delhi, India, 3 Department of Chemistry, School of Chemical and Life Sciences, Jamia Hamdard, New Delhi, India, 4 Department of Pharmaceutical Chemistry, School of Pharmaceutical Education and Research, Jamia Hamdard, New Delhi, India Epilepsy is a complex neurological disorder, characterized by frequent electrical activity in brain regions. Inflammation and apoptosis cascade activation are serious neurological sequelae during seizures. Fisetin (3, 3′,4′,7-tetrahydroxyflavone), a flavonoid molecule, is considered for its effective anti-inflammatory and anti-apoptotic properties. This study Edited by: investigated the neuroprotective effect of fisetin on experimental epilepsy. For acute Mohd Farooq Shaikh, studies, increasing current electroshock (ICES) and pentylenetetrazole (PTZ)-induced Monash University, Malaysia seizure tests were performed to evaluate the antiseizure activity of fisetin. For the chronic Reviewed by: Shuai Guo, study, the kindling model was established by the administration of PTZ in subconvulsive Huazhong Agricultural dose (25 mg/kg, i.p.). Mice were treated with fisetin (5, 10, and 20 mg/kg, p.o.) to study University, China Syed Shadab Raza, its probable antiseizure mechanism. The kindled mice were evaluated for seizure scores. ERA’s Lucknow Medical College, India Their hippocampus and cortex were assessed for neuronal damage, inflammation, and *Correspondence: apoptosis. -
Anti-Inflammatory Effects of Kaempferol, Myricetin, Fisetin and Ibuprofen in Neonatal Rats
Guo & Feng Tropical Journal of Pharmaceutical Research August 2017; 16 (8): 1819-1826 ISSN: 1596-5996 (print); 1596-9827 (electronic) © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. All rights reserved. Available online at http://www.tjpr.org http://dx.doi.org/10.4314/tjpr.v16i8.10 Original Research Article Anti-inflammatory effects of kaempferol, myricetin, fisetin and ibuprofen in neonatal rats Peng Guo and Yun-Yun Feng* The Second Pediatric Department of Internal Medicine, Zhumadian Central Hospital, Zhumadian, No. 747 Zhonghua Road, Zhumadian, Henan Province 463000, China *For correspondence: Email: [email protected]; Tel/Fax: 0086-0396-2726840 Sent for review: 9 September 2016 Revised accepted: 14 July 2017 Abstract Purpose: To investigate the anti-inflammatory effects of kaempferol, myricetin, fisetin and ibuprofen in rat pups. Methods: The expression levels of cyclooxygenase (COX)-1, COX-2 and tumour necrosis factor-α (TNF-α) were determined by western blotting; the inhibition of these proteins by plant compounds was evaluated. In addition, a computational simulation of the molecular interactions of the compounds at the active sites of the proteins was performed using a molecular docking approach. Absorption, distribution, metabolism and excretion (ADME) and toxicity analysis of the plant compounds was also performed. Results: Kaempferol, myricetin and fisetin inhibited the activities of COX-1, COX-2 and TNF-α by 70–88 %. The computational simulation revealed the molecular interactions of these compounds at the active sites of COX-1, COX-2 and TNF-α. ADME and toxicity analysis demonstrated that the three plant compounds were safe. Conclusion: The data obtained indicate that myricetin, kaempferol and fisetin exert anti-inflammatory effects in neonatal rats, with fewer side effects than those of ibuprofen. -
Flavonoids: an Overview
Vidya V. Gawande et al. / Journal of Pharmacy Research 2012,5(11),5099-5101 Review Article Available online through ISSN: 0974-6943 http://jprsolutions.info Flavonoids: An Overview Vidya V. Gawande* and S. V. Kalikar Department of Pharmacy,Government Polytechnic, Gadgenagar, VMV Road, Amravati(MS), India 444603 Received on:14-07-2012; Revised on: 19-08-2012; Accepted on:23-09-2012 ABSTRACT Flavonoids belong to a group of polyphenolic compounds, which are classified as flavonols, flavonones, flavones, flavan-3-ols and isoflavones, anthocynidins according to the positions of the substitutes present on the parent molecule. Flavonoids occur as aglycones, glycosides and methylated derivatives in plants. Flavonoids occur naturally in fruit, vegetables, and beverages such as tea and wine and over 4000 structurally unique flavonoids have been identified in plant sources. These are primarily recognized as the pigments responsible for the many shades of yellow, orange, and red in flowers, fruits, and leaves. The major actions of flavonoids are those against cardiovascular diseases, ulcers, viruses, inflammation, osteoporosis, diarrhea and arthritis. Flavonoids have also been known to possess biochemical effects, which inhibit a number of enzymes such as aldosereductase, xanthine oxidase, phosphodiesterase, Ca+2-ATPase, lipoxygenase, cycloxygenase, etc. They also have a regulatory role on different hormones like estrogens, androgens and thyroid hormones. Flavonoids like quercetin are shown to produce anti-inflammatory effect. The flavonoids in tea are found to be responsible for the prevention of osteoporosis. Quercetin is now found to show inhibiting effects against herpes simplex virus. Antidiarrheal effect is found to be shown by the flavonoids present in cocoa. -
Graphical Abstract CG 18-1-MS
Send Orders for Reprints to [email protected] 3 Current Genomics, 2017, 18, 3-26 REVIEW ARTICLE ISSN: 1389-2029 eISSN: 1875-5488 Impact Factor: 2.43 Established Human Cell Lines as Models to Study Anti-leukemic Effects of Flavonoids BENTHAM SCIENCE Katrin Sak* and Hele Everaus Department of Hematology and Oncology, University of Tartu, Tartu, Estonia Abstract: Despite the extensive work on pathological mechanisms and some recent advances in the treatment of different hematological malignancies, leukemia continues to present a significant challenge being frequently considered as incurable disease. Therefore, the development of novel therapeutic agents with high efficacy and low toxicity is urgently needed to improve the overall survival rate of pa- A R T I C L E H I S T O R Y tients. In this comprehensive review article, the current knowledge about the anticancer activities of Received: May 11, 2015 flavonoids as plant secondary polyphenolic metabolites in the most commonly used human established Revised: November 20, 2015 Accepted: November 27, 2015 leukemia cell lines (HL-60, NB4, KG1a, U937, THP-1, K562, Jurkat, CCRF- CEM, MOLT-3, and MOLT-4) is compiled, revealing clear anti-proliferative, pro-apoptotic, cell cycle arresting, and differ- DOI: 10.2174/138920291766616080316 entiation inducing effects for certain compounds. Considering the low toxicity of these substances in 5447 normal blood cells, the presented data show a great potential of flavonoids to be developed into novel anti-leukemia agents applicable also in the malignant cells resistant to the current conventional che- motherapeutic drugs. Keywords: Antiproliferation, Apoptosis, Cell cycle arrest, Cytotoxicity, Differentiation, Flavonoids, Leukemia, Human cell lines. -
Cytotoxic Activities of Flavonoids from Centaurea Scoparia
Hindawi Publishing Corporation e Scientific World Journal Volume 2014, Article ID 274207, 7 pages http://dx.doi.org/10.1155/2014/274207 Research Article Cytotoxic Activities of Flavonoids from Centaurea scoparia Sayed A. Ahmed and Emadeldin M. Kamel Chemistry Department, Faculty of Science, Beni Suef University, Salah Salem Street, P.O. Box 62514, Beni Suef 62514, Egypt Correspondence should be addressed to Sayed A. Ahmed; [email protected] Received 17 January 2014; Accepted 22 May 2014; Published 11 June 2014 Academic Editor: Diego Savoia Copyright © 2014 S. A. Ahmed and E. M. Kamel. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Phytochemical studies on the ethanolic extract of the aerial parts of Centaurea scoparia ledtotheisolationof two new flavonoids, 3 ,4 -dihydroxy-(3 ,4 -dihydro-3 -hydroxy-4 -acetoxy)-2 ,2 -dimethylpyrano-(5 ,6 :7,8)-flavone-3-O-- D-glucopyranoside (1)and3,3,4 -trihydroxy-(3 ,4 -dihydro-3 ,4 -dihydroxy)-2 ,2 -dimethylpyrano-(5 ,6 :7,8)-flavone (2), along with eight known flavonoids isolated for the first time from this plant, cynaroside (3), Apigetrin (4), centaureidin (5), oroxylin A(6), 5,7-dihydroxy-3 ,4 ,5 -trimethoxyflavone (7), atalantoflavone (8), 5-hydroxy-3 ,4 ,8-trimethoxy-2 ,2 -dimethylpyrano (5 ,6 :6,7)-flavone (9), and 3 ,4 ,5,8-tetramethoxy-2 ,2 -dimethylpyrano (5 ,6 :6,7)-flavone (10). The structures of the isolated compounds were elucidated by means of spectroscopic tools including 1D and 2D NMR, UV,IR, and mass spectroscopy. -
Isorhamnetin a Review of Pharmacological Effects
LJMU Research Online Gong, G, Guan, Y-Y, Zhang, Z-L, Rahman, K, Wang, S-J, Zhou, S, Luan, X and Zhang, H Isorhamnetin: A review of pharmacological effects. http://researchonline.ljmu.ac.uk/id/eprint/13470/ Article Citation (please note it is advisable to refer to the publisher’s version if you intend to cite from this work) Gong, G, Guan, Y-Y, Zhang, Z-L, Rahman, K, Wang, S-J, Zhou, S, Luan, X and Zhang, H (2020) Isorhamnetin: A review of pharmacological effects. Biomedicine & Pharmacotherapy, 128. ISSN 0753-3322 LJMU has developed LJMU Research Online for users to access the research output of the University more effectively. Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Users may download and/or print one copy of any article(s) in LJMU Research Online to facilitate their private study or for non-commercial research. You may not engage in further distribution of the material or use it for any profit-making activities or any commercial gain. The version presented here may differ from the published version or from the version of the record. Please see the repository URL above for details on accessing the published version and note that access may require a subscription. For more information please contact [email protected] http://researchonline.ljmu.ac.uk/ Biomedicine & Pharmacotherapy 128 (2020) 110301 Contents lists available at ScienceDirect Biomedicine & Pharmacotherapy journal homepage: www.elsevier.com/locate/biopha Review Isorhamnetin: A review -
Mechanisms of Toxic Action of the Flavonoid Quercetin and Its Phase II Metabolites
Mechanisms of toxic action of the flavonoid quercetin and its phase II metabolites Hester van der Woude Promotor: Prof. Dr. Ir. I.M.C.M. Rietjens Hoogleraar in de Toxicologie Wageningen Universiteit Co-promotor: Dr. G.M. Alink Universitair Hoofddocent, Sectie Toxicologie Wageningen Universiteit. Promotiecommissie: Prof. Dr. A. Bast Universiteit Maastricht Dr. Ir. P.C.H. Hollman RIKILT Instituut voor Voedselveiligheid, Wageningen Prof. Dr. Ir. F.J. Kok Wageningen Universiteit Prof. Dr. T. Walle Medical University of South Carolina, Charleston, SC, USA Dit onderzoek is uitgevoerd binnen de onderzoekschool VLAG Mechanisms of toxic action of the flavonoid quercetin and its phase II metabolites Hester van der Woude Proefschrift ter verkrijging van de graad van doctor op gezag van de rector magnificus van Wageningen Universiteit, Prof. Dr. M.J. Kropff, in het openbaar te verdedigen op vrijdag 7 april 2006 des namiddags te half twee in de Aula Title Mechanisms of toxic action of the flavonoid quercetin and its phase II metabolites Author Hester van der Woude Thesis Wageningen University, Wageningen, the Netherlands (2006) with abstract, with references, with summary in Dutch. ISBN 90-8504-349-2 Abstract During and after absorption in the intestine, quercetin is extensively metabolised by the phase II biotransformation system. Because the biological activity of flavonoids is dependent on the number and position of free hydroxyl groups, a first objective of this thesis was to investigate the consequences of phase II metabolism of quercetin for its biological activity. For this purpose, a set of analysis methods comprising HPLC-DAD, LC-MS and 1H NMR proved to be a useful tool in the identification of the phase II metabolite pattern of quercetin in various biological systems. -
(Piper Nigrum L.) Products Based on LC-MS/MS Analysis
molecules Article Nontargeted Metabolomics for Phenolic and Polyhydroxy Compounds Profile of Pepper (Piper nigrum L.) Products Based on LC-MS/MS Analysis Fenglin Gu 1,2,3,*, Guiping Wu 1,2,3, Yiming Fang 1,2,3 and Hongying Zhu 1,2,3,* 1 Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning 571533, China; [email protected] (G.W.); [email protected] (Y.F.) 2 National Center of Important Tropical Crops Engineering and Technology Research, Wanning 571533, China 3 Key Laboratory of Genetic Resources Utilization of Spice and Beverage Crops, Ministry of Agriculture, Wanning 571533, China * Correspondence: [email protected] (F.G.); [email protected] (H.Z.); Tel.: +86-898-6255-3687 (F.G.); +86-898-6255-6090 (H.Z.); Fax: +86-898-6256-1083 (F.G. & H.Z.) Received: 16 July 2018; Accepted: 7 August 2018; Published: 9 August 2018 Abstract: In the present study, nontargeted metabolomics was used to screen the phenolic and polyhydroxy compounds in pepper products. A total of 186 phenolic and polyhydroxy compounds, including anthocyanins, proanthocyanidins, catechin derivatives, flavanones, flavones, flavonols, isoflavones and 3-O-p-coumaroyl quinic acid O-hexoside, quinic acid (polyhydroxy compounds), etc. For the selected 50 types of phenolic compound, except malvidin 3,5-diglucoside (malvin), 0 L-epicatechin and 4 -hydroxy-5,7-dimethoxyflavanone, other compound contents were present in high contents in freeze-dried pepper berries, and pinocembrin was relatively abundant in two kinds of pepper products. The score plots of principal component analysis indicated that the pepper samples can be classified into four groups on the basis of the type pepper processing. -
IN SILICO ANALYSIS of FUNCTIONAL Snps of ALOX12 GENE and IDENTIFICATION of PHARMACOLOGICALLY SIGNIFICANT FLAVONOIDS AS
Tulasidharan Suja Saranya et al. Int. Res. J. Pharm. 2014, 5 (6) INTERNATIONAL RESEARCH JOURNAL OF PHARMACY www.irjponline.com ISSN 2230 – 8407 Research Article IN SILICO ANALYSIS OF FUNCTIONAL SNPs OF ALOX12 GENE AND IDENTIFICATION OF PHARMACOLOGICALLY SIGNIFICANT FLAVONOIDS AS LIPOXYGENASE INHIBITORS Tulasidharan Suja Saranya, K.S. Silvipriya, Manakadan Asha Asokan* Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Viswa Vidyapeetham University, AIMS Health Sciences Campus, Kochi, Kerala, India *Corresponding Author Email: [email protected] Article Received on: 20/04/14 Revised on: 08/05/14 Approved for publication: 22/06/14 DOI: 10.7897/2230-8407.0506103 ABSTRACT Cancer is a disease affecting any part of the body and in comparison with normal cells there is an elevated level of lipoxygenase enzyme in different cancer cells. Thus generation of lipoxygenase enzyme inhibitors have suggested being valuable. Individual variation was identified by the functional effects of Single Nucleotide Polymorphisms (SNPs). 696 SNPs were identified from the ALOX12 gene, out of which 73 were in the coding non-synonymous region, from which 8 were found to be damaging. In silico analysis was performed to determine naturally occurring flavonoids such as isoflavones having the basic 3- phenylchromen-4-one skeleton for the pharmacological activity, like Genistein, Diadzein, Irilone, Orobol and Pseudobaptigenin. O-methylated isoflavones such as Biochanin, Calycosin, Formononetin, Glycitein, Irigenin, 5-O-Methylgenistein, Pratensein, Prunetin, ψ-Tectorigenin, Retusin and Tectorigenine were also used for the study. Other natural products like Aesculetin, a coumarin derivative; flavones such as ajoene and baicalein were also used for the comparative study of these natural compounds along with acteoside and nordihydroguaiaretic acid (antioxidants) and active inhibitors like Diethylcarbamazine, Zileuton and Azelastine as standard for the computational analysis.