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(Hordeum Vulgare L.) Seedlings Via Their
Ra et al. Appl Biol Chem (2020) 63:38 https://doi.org/10.1186/s13765-020-00519-9 NOTE Open Access Evaluation of antihypertensive polyphenols of barley (Hordeum vulgare L.) seedlings via their efects on angiotensin-converting enzyme (ACE) inhibition Ji‑Eun Ra1, So‑Yeun Woo2, Hui Jin3, Mi Ja Lee2, Hyun Young Kim2, Hyeonmi Ham2, Ill‑Min Chung1 and Woo Duck Seo2* Abstract Angiotensin‑converting enzyme (ACE) is an important therapeutic target in the regulation of high blood pressure. This study was conducted to investigate the alterations in blood pressure associated with ACE inhibition activity of the polyphenols (1–10), including 3‑O‑feruloylquinic acid (1), lutonarin (2), saponarin (3), isoorientin (4), orientin (5), isovitexin (6), isoorientin‑7‑O‑[6‑sinapoyl]‑glucoside (7), isoorientin‑7‑O‑[6‑feruloyl]‑glucoside (8), isovitexin‑7‑O‑ [6‑sinapoyl]‑glucoside (9), and isovitexin‑7‑O‑[6‑feruloyl]‑glucoside (10), isolated from barley seedlings (BS). All the isolated polyphenols exhibited comparable IC50 values of ACE inhibition activity (7.3–43.8 µM) with quercetin (25.2 0.2 µM) as a positive control, and their inhibition kinetic models were identifed as noncompetitive inhibition. ± Especially, compound 4 was revealed to be an outstanding ACE inhibitor (IC50 7.3 0.1 µM, Ki 6.6 0.1 µM). Based on the compound structure–activity relationships, the free hydroxyl groups of =favone± ‑moieties =and glucose± connec‑ tions at the A ring of the favone moieties were important factors for inhibition of ACE. The alcohol extract of BS also 1 demonstrated potent ACE inhibition activity (66.5% 2.2% at 5000 µg mL− ). -
Characterization of C-Glycosidic Flavonoids from Brazilian Passiflora Species Using Lc/Ms Exact Mass Measurement
CHARACTERIZATION OF C-GLYCOSIDIC FLAVONOIDS FROM BRAZILIAN PASSIFLORA SPECIES USING LC/MS EXACT MASS MEASUREMENT 1 2 2 NOTE M. McCullagh , C.A.M. Pereira , J.H. Yariwake 1Waters Corporation, Floats Road, Wythenshawe, Manchester, M23 9LZ, UK 2Universidade de São Paulo, Instituto de Química de São Carlos, São Carlos, SP, Brazil OVERVIEW This application note describes the analysis of extracts Recently issues have arisen with Kava Kava, a natural from Passiflora species using real time centroid exact health product, which is used for its anti-depressant and mass measurement. The system used comprised of an anti-anxiety properties. Investigations into the safety of LCT™ orthogonal acceleration (oa-TOF) time of flight Kava have taken place within several European mass spectrometer with LockSpray™ source, Waters® countries, including Germany, U.K., Switzerland, 2996 PDA and Waters Alliance® HT 2795 France, Spain and parts of Scandinavia. In Switzerland Separations Module. and Germany cases of liver damage were reported. In Application the US the FDA has investigated Kava's safety, where INTRODUCTION as in Canada the public were advised not to take the EU Directive 2001/83/EC will regulate and produce a supplement until product safety could be assured. The set of harmonized assessment criteria for the efficacy Kava market in Germany alone is $25m. Proving the and safety "Herbal Medicinal Products for traditional efficacy of such a product is economically viable. use". The current and future E.U. member states will Such issues illustrate how regulation currently affects produce and abide by this directive, making 28 states the natural health product market and also why new in total. -
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. -
The Phytochemistry of Cherokee Aromatic Medicinal Plants
medicines Review The Phytochemistry of Cherokee Aromatic Medicinal Plants William N. Setzer 1,2 1 Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA; [email protected]; Tel.: +1-256-824-6519 2 Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA Received: 25 October 2018; Accepted: 8 November 2018; Published: 12 November 2018 Abstract: Background: Native Americans have had a rich ethnobotanical heritage for treating diseases, ailments, and injuries. Cherokee traditional medicine has provided numerous aromatic and medicinal plants that not only were used by the Cherokee people, but were also adopted for use by European settlers in North America. Methods: The aim of this review was to examine the Cherokee ethnobotanical literature and the published phytochemical investigations on Cherokee medicinal plants and to correlate phytochemical constituents with traditional uses and biological activities. Results: Several Cherokee medicinal plants are still in use today as herbal medicines, including, for example, yarrow (Achillea millefolium), black cohosh (Cimicifuga racemosa), American ginseng (Panax quinquefolius), and blue skullcap (Scutellaria lateriflora). This review presents a summary of the traditional uses, phytochemical constituents, and biological activities of Cherokee aromatic and medicinal plants. Conclusions: The list is not complete, however, as there is still much work needed in phytochemical investigation and pharmacological evaluation of many traditional herbal medicines. Keywords: Cherokee; Native American; traditional herbal medicine; chemical constituents; pharmacology 1. Introduction Natural products have been an important source of medicinal agents throughout history and modern medicine continues to rely on traditional knowledge for treatment of human maladies [1]. Traditional medicines such as Traditional Chinese Medicine [2], Ayurvedic [3], and medicinal plants from Latin America [4] have proven to be rich resources of biologically active compounds and potential new drugs. -
In Vitro Metabolism of Six C-Glycosidic Flavonoids from Passiflora Incarnata L
International Journal of Molecular Sciences Article In Vitro Metabolism of Six C-Glycosidic Flavonoids from Passiflora incarnata L. Martina Tremmel 1, Josef Kiermaier 2 and Jörg Heilmann 1,* 1 Department of Pharmaceutical Biology, Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany; [email protected] 2 Department of Central Analytics, Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany; [email protected] * Correspondence: [email protected] Abstract: Several medical plants, such as Passiflora incarnata L., contain C-glycosylated flavonoids, which may contribute to their efficacy. Information regarding the bioavailability and metabolism of these compounds is essential, but not sufficiently available. Therefore, the metabolism of the C-glycosylated flavones orientin, isoorientin, schaftoside, isoschaftoside, vitexin, and isovitexin was investigated using the Caco-2 cell line as an in vitro intestinal and epithelial metabolism model. Isovitexin, orientin, and isoorientin showed broad ranges of phase I and II metabolites containing hy- droxylated, methoxylated, and sulfated compounds, whereas schaftoside, isoschaftoside, and vitexin underwent poor metabolism. All metabolites were identified via UHPLC-MS or UHPLC-MS/MS using compound libraries containing all conceivable metabolites. Some structures were confirmed via UHPLC-MS experiments with reference compounds after a cleavage reaction using glucuronidase and sulfatase. Of particular interest is the observed cleavage of the C–C bonds between sugar and aglycone residues in isovitexin, orientin, and isoorientin, resulting in unexpected glucuronidated or sulfated luteolin and apigenin derivatives. These findings indicate that C-glycosidic flavones can be Citation: Tremmel, M.; Kiermaier, J.; highly metabolized in the intestine. -
Important Flavonoids and Their Role As a Therapeutic Agent
molecules Review Important Flavonoids and Their Role as a Therapeutic Agent Asad Ullah 1 , Sidra Munir 1 , Syed Lal Badshah 1,* , Noreen Khan 1, Lubna Ghani 2, Benjamin Gabriel Poulson 3 , Abdul-Hamid Emwas 4 and Mariusz Jaremko 3,* 1 Department of Chemistry, Islamia College University Peshawar, Peshawar 25120, Pakistan; [email protected] (A.U.); [email protected] (S.M.); [email protected] (N.K.) 2 Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad, Azad Kashmir 13230, Pakistan; [email protected] 3 Division of Biological and Environmental Sciences and Engineering (BESE), King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia; [email protected] 4 Core Labs, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia; [email protected] * Correspondence: [email protected] (S.L.B.); [email protected] (M.J.) Received: 20 September 2020; Accepted: 1 November 2020; Published: 11 November 2020 Abstract: Flavonoids are phytochemical compounds present in many plants, fruits, vegetables, and leaves, with potential applications in medicinal chemistry. Flavonoids possess a number of medicinal benefits, including anticancer, antioxidant, anti-inflammatory, and antiviral properties. They also have neuroprotective and cardio-protective effects. These biological activities depend upon the type of flavonoid, its (possible) mode of action, and its bioavailability. These cost-effective medicinal components have significant biological activities, and their effectiveness has been proved for a variety of diseases. The most recent work is focused on their isolation, synthesis of their analogs, and their effects on human health using a variety of techniques and animal models. -
Distribution of Flavonoids Among Malvaceae Family Members – a Review
Distribution of flavonoids among Malvaceae family members – A review Vellingiri Vadivel, Sridharan Sriram, Pemaiah Brindha Centre for Advanced Research in Indian System of Medicine (CARISM), SASTRA University, Thanjavur, Tamil Nadu, India Abstract Since ancient times, Malvaceae family plant members are distributed worldwide and have been used as a folk remedy for the treatment of skin diseases, as an antifertility agent, antiseptic, and carminative. Some compounds isolated from Malvaceae members such as flavonoids, phenolic acids, and polysaccharides are considered responsible for these activities. Although the flavonoid profiles of several Malvaceae family members are REVIEW REVIEW ARTICLE investigated, the information is scattered. To understand the chemical variability and chemotaxonomic relationship among Malvaceae family members summation of their phytochemical nature is essential. Hence, this review aims to summarize the distribution of flavonoids in species of genera namely Abelmoschus, Abroma, Abutilon, Bombax, Duboscia, Gossypium, Hibiscus, Helicteres, Herissantia, Kitaibelia, Lavatera, Malva, Pavonia, Sida, Theobroma, and Thespesia, Urena, In general, flavonols are represented by glycosides of quercetin, kaempferol, myricetin, herbacetin, gossypetin, and hibiscetin. However, flavonols and flavones with additional OH groups at the C-8 A ring and/or the C-5′ B ring positions are characteristic of this family, demonstrating chemotaxonomic significance. Key words: Flavones, flavonoids, flavonols, glycosides, Malvaceae, phytochemicals INTRODUCTION connate at least at their bases, but often forming a tube around the pistils. The pistils are composed of two to many connate he Malvaceae is a family of flowering carpels. The ovary is superior, with axial placentation, with plants estimated to contain 243 genera capitate or lobed stigma. The flowers have nectaries made with more than 4225 species. -
BIOLOGICAL PROPERTIES of SELECTED FLAVONOIDS of ROOIBOS (Aspalathus Linearis)
BIOLOGICAL PROPERTIES OF SELECTED FLAVONOIDS OF ROOIBOS (Aspalathus linearis) Petra W Snijman Thesis presented in partial fulfilment of the requirements for the degree of Master of Science in Chemistry at the University of the Western Cape Study Leader: Prof IR Green Co-study Leaders: Prof E Joubert Prof WCA Gelderblom June 2007 ii DECLARATION I, the undersigned, hereby declare that the work contained in this thesis is my own original work and that I have not previously in its entirety or in part submitted it at any university for a degree. _______________________________ ____________ Petra Wilhelmina Snijman Date Copyright © 2007 University of the Western Cape All rights reserved iii ABSTRACT Bioactivity-guided fractionation was used to identify the most potent antioxidant and antimutagenic fractions contained in the methanol extract of unfermented rooibos (Aspalathus linearis), as well as the bioactive principles for the most potent antioxidant fractions. The different extracts and fractions were screened using Salmonella typhimurium tester strain TA98 and metabolically activated 2- acetoaminofluorene (2-AAF) to evaluate antimutagenic potential, while the antioxidant potency was assessed by two different in vitro assays, i.e. the inhibition of Fe(II) induced microsomal lipid peroxidation and the scavenging of the 2,2'- azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation. The most polar XAD fraction displayed the most protection against 2-AAF induced mutagenesis in TA98. Successive fractionation of the two XAD fractions -
Biosynthesis of Vitexin and Isovitexin: Enzymatic Synthesis of the C-Glucosylflavones Vitexin and Isovitexin with an Enzyme Preparation Fromfagopyrum Esculentum M
Biosynthesis of Vitexin and Isovitexin: Enzymatic Synthesis of the C-Glucosylflavones Vitexin and Isovitexin with an Enzyme Preparation fromFagopyrum esculentum M. Seedlings F. Kerscher and G. Franz Lehrstuhl für Pharmazeutische Biologie, Universität Regensburg, Universitätsstraße 31, D-8400 Regensburg, Bundesrepublik Deutschland Z. Naturforsch. 42c, 519—524 (1987); received October 8/December 29, 1986 Biosynthesis of Vitexin, Fagopyrum esculentum M., Flavonoid-C-glucosylation, 2-Hydroxy- flavanones A C-glucosyltransferase from Fagopyrum esculentum seedlings catalyzes the transfer of glucose from UDP-glucose or ADP-glucose to 2-hydroxyflavanones. In cell-free enzyme preparations it was shown that only 2-hydroxyflavanones, e.g. 2,4',5,7-tetrahydroxyflavanone and 2,5,7-tri- hydroxyflavanone were appropriate substrates. Naringenin, naringenin-chalcone and the flavones apigenin and chrysin cannot act as glucosyl acceptors in C-glucosyl-flavonoid biosynthesis. This demonstrates that C-glucosylation occurs after oxidation of flavanones. Introduction Cotyledons of Fagopyrum esculentum are known C-glucosyl flavonoids are widespread in the plant to produce considerable amounts of vitexin and kingdom with the most important representatives isovitexin [ 8 ]. The aim of the present work was to being vitexin and isovitexin [1], The biosynthesis of demonstrate at which stage during biogenesis of the aglycon C-glucosylation occurs. Enzyme extracts the aglycon was subject of several investigations [ 2 ], Nothing, however, is known about the mechanism of were prepared from this cotyledon material and incu the C-glucosylation of these flavone compounds [3]. bated with several hypothetic glucosyldonors and In vivo experiments demonstrated that flavanones acceptors such as naringenin-chalcone, naringenin, might act as precursors for flavone-C-glucosides but 2 -hydroxynaringenin, apigenin and further with not the flavones [4], On the other hand the 2,5,7-trihydroxyflavanone and chrysin. -
Isovitexin Exerts Anti-Inflammatory and Anti-Oxidant Activities on Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting MA
Int. J. Biol. Sci. 2016, Vol. 12 72 Ivyspring International Publisher International Journal of Biological Sciences 2016; 12(1): 72-86. doi: 10.7150/ijbs.13188 Research Paper Isovitexin Exerts Anti-Inflammatory and Anti-Oxidant Activities on Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting MAPK and NF-κB and Activating HO-1/Nrf2 Pathways Hongming Lv1#, Zhenxiang Yu2#, Yuwei Zheng1, Lidong Wang1, Xiaofeng Qin1, Genhong Cheng1, Xinxin Ci1 1. Institute of Translational Medicine, The First Hospital of Jilin University, College of Veterinary Medicine, Jilin University, Changchun, China 2. Department of Respiratory Medicine, The First Hospital of Jilin University, Changchun, China. # These authors contributed equally to this work. Corresponding author: X.-X.Ci, Institute of Translational Medicine, The First Hospital, Jilin University, Changchun, 130001, China. Tel.: +86 431 88783044; E-mail addresses: [email protected] (X.-X.Ci.) © Ivyspring International Publisher. Reproduction is permitted for personal, noncommercial use, provided that the article is in whole, unmodified, and properly cited. See http://ivyspring.com/terms for terms and conditions. Received: 2015.07.08; Accepted: 2015.11.02; Published: 2016.01.01 Abstract Oxidative damage and inflammation are closely associated with the pathogenesis of acute lung injury (ALI). Thus, we explored the protective effect of isovitexin (IV), a glycosylflavonoid, in the context of ALI. To accomplish this, we created in vitro and in vivo models by respectively exposing macrophages to lipopolysaccharide (LPS) and using LPS to induce ALI in mice. In vitro, our results showed that IV treatment reduced LPS-induced pro-inflammatory cytokine secretion, iNOS and COX-2 expression and decreased the generation of ROS. -
Potential Role of Flavonoids in Treating Chronic Inflammatory Diseases with a Special Focus on the Anti-Inflammatory Activity of Apigenin
Review Potential Role of Flavonoids in Treating Chronic Inflammatory Diseases with a Special Focus on the Anti-Inflammatory Activity of Apigenin Rashida Ginwala, Raina Bhavsar, DeGaulle I. Chigbu, Pooja Jain and Zafar K. Khan * Department of Microbiology and Immunology, and Center for Molecular Virology and Neuroimmunology, Center for Cancer Biology, Institute for Molecular Medicine and Infectious Disease, Drexel University College of Medicine, Philadelphia, PA 19129, USA; [email protected] (R.G.); [email protected] (R.B.); [email protected] (D.I.C.); [email protected] (P.J.) * Correspondence: [email protected] Received: 28 November 2018; Accepted: 30 January 2019; Published: 5 February 2019 Abstract: Inflammation has been reported to be intimately linked to the development or worsening of several non-infectious diseases. A number of chronic conditions such as cancer, diabetes, cardiovascular disorders, autoimmune diseases, and neurodegenerative disorders emerge as a result of tissue injury and genomic changes induced by constant low-grade inflammation in and around the affected tissue or organ. The existing therapies for most of these chronic conditions sometimes leave more debilitating effects than the disease itself, warranting the advent of safer, less toxic, and more cost-effective therapeutic alternatives for the patients. For centuries, flavonoids and their preparations have been used to treat various human illnesses, and their continual use has persevered throughout the ages. This review focuses on the anti-inflammatory actions of flavonoids against chronic illnesses such as cancer, diabetes, cardiovascular diseases, and neuroinflammation with a special focus on apigenin, a relatively less toxic and non-mutagenic flavonoid with remarkable pharmacodynamics. Additionally, inflammation in the central nervous system (CNS) due to diseases such as multiple sclerosis (MS) gives ready access to circulating lymphocytes, monocytes/macrophages, and dendritic cells (DCs), causing edema, further inflammation, and demyelination.