Flavonoids As Anticancer Agents
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Identification of Compounds with Potential Therapeutic Uses From
International Journal of Molecular Sciences Article Identification of Compounds with Potential Therapeutic Uses from Sweet Pepper (Capsicum annuum L.) Fruits and Their Modulation by Nitric Oxide (NO) Lucía Guevara 1, María Ángeles Domínguez-Anaya 1, Alba Ortigosa 1, Salvador González-Gordo 1 , Caridad Díaz 2 , Francisca Vicente 2 , Francisco J. Corpas 1 , José Pérez del Palacio 2 and José M. Palma 1,* 1 Group of Antioxidant, Free Radicals and Nitric Oxide in Biotechnology, Food and Agriculture, Department of Biochemistry, Cell and Molecular Biology of Plants, Estación Experimental del Zaidín, CSIC, 18008 Granada, Spain; [email protected] (L.G.); [email protected] (M.Á.D.-A.); [email protected] (A.O.); [email protected] (S.G.-G.); [email protected] (F.J.C.) 2 Department of Screening & Target Validation, Fundación MEDINA, 18016 Granada, Spain; [email protected] (C.D.); [email protected] (F.V.); [email protected] (J.P.d.P.) * Correspondence: [email protected]; Tel.: +34-958-181-1600; Fax: +34-958-181-609 Abstract: Plant species are precursors of a wide variety of secondary metabolites that, besides being useful for themselves, can also be used by humans for their consumption and economic benefit. Pepper (Capsicum annuum L.) fruit is not only a common food and spice source, it also stands out for containing high amounts of antioxidants (such as vitamins C and A), polyphenols and capsaicinoids. Citation: Guevara, L.; Particular attention has been paid to capsaicin, whose anti-inflammatory, antiproliferative and Domínguez-Anaya, M.Á.; Ortigosa, A.; González-Gordo, S.; Díaz, C.; analgesic activities have been reported in the literature. -
Plant Phenolics: Bioavailability As a Key Determinant of Their Potential Health-Promoting Applications
antioxidants Review Plant Phenolics: Bioavailability as a Key Determinant of Their Potential Health-Promoting Applications Patricia Cosme , Ana B. Rodríguez, Javier Espino * and María Garrido * Neuroimmunophysiology and Chrononutrition Research Group, Department of Physiology, Faculty of Science, University of Extremadura, 06006 Badajoz, Spain; [email protected] (P.C.); [email protected] (A.B.R.) * Correspondence: [email protected] (J.E.); [email protected] (M.G.); Tel.: +34-92-428-9796 (J.E. & M.G.) Received: 22 October 2020; Accepted: 7 December 2020; Published: 12 December 2020 Abstract: Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom that can be categorized as flavonoids and non-flavonoids. Interest in phenolic compounds has dramatically increased during the last decade due to their biological effects and promising therapeutic applications. In this review, we discuss the importance of phenolic compounds’ bioavailability to accomplish their physiological functions, and highlight main factors affecting such parameter throughout metabolism of phenolics, from absorption to excretion. Besides, we give an updated overview of the health benefits of phenolic compounds, which are mainly linked to both their direct (e.g., free-radical scavenging ability) and indirect (e.g., by stimulating activity of antioxidant enzymes) antioxidant properties. Such antioxidant actions reportedly help them to prevent chronic and oxidative stress-related disorders such as cancer, cardiovascular and neurodegenerative diseases, among others. Last, we comment on development of cutting-edge delivery systems intended to improve bioavailability and enhance stability of phenolic compounds in the human body. Keywords: antioxidant activity; bioavailability; flavonoids; health benefits; phenolic compounds 1. Introduction Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom with around 8000 different phenolic structures [1]. -
And East Siberian Rhododendron (Rh. Adamsii) Using Supercritical CO2-Extraction and HPLC-ESI-MS/MS Spectrometry
molecules Article Comparative Analysis of Far East Sikhotinsky Rhododendron (Rh. sichotense) and East Siberian Rhododendron (Rh. adamsii) Using Supercritical CO2-Extraction and HPLC-ESI-MS/MS Spectrometry Mayya Razgonova 1,2,* , Alexander Zakharenko 1,2 , Sezai Ercisli 3 , Vasily Grudev 4 and Kirill Golokhvast 1,2,5 1 N.I. Vavilov All-Russian Institute of Plant Genetic Resources, 190000 Saint-Petersburg, Russia; [email protected] (A.Z.); [email protected] (K.G.) 2 SEC Nanotechnology, Far Eastern Federal University, 690950 Vladivostok, Russia 3 Agricultural Faculty, Department of Horticulture, Ataturk University, 25240 Erzurum, Turkey; [email protected] 4 Far Eastern Investment and Export Agency, 123112 Moscow, Russia; [email protected] 5 Pacific Geographical Institute, Far Eastern Branch of the Russian Academy of Sciences, 690041 Vladivostok, Russia * Correspondence: [email protected] Academic Editors: Seung Hwan Yang and Satyajit Sarker Received: 29 June 2020; Accepted: 12 August 2020; Published: 19 August 2020 Abstract: Rhododendron sichotense Pojark. and Rhododendron adamsii Rheder have been actively used in ethnomedicine in Mongolia, China and Buryatia (Russia) for centuries, as an antioxidant, immunomodulating, anti-inflammatory, vitality-restoring agent. These plants contain various phenolic compounds and fatty acids with valuable biological activity. Among green and selective extraction methods, supercritical carbon dioxide (SC-CO2) extraction has been shown to be the method of choice for the recovery of these naturally occurring compounds. Operative parameters and working conditions have been optimized by experimenting with different pressures (300–400 bar), temperatures (50–60 ◦C) and CO2 flow rates (50 mL/min) with 1% ethanol as co-solvent. The extraction time varied from 60 to 70 min. -
And Season-Dependent Pattern of Flavonol Glycosides In
www.nature.com/scientificreports OPEN Age‑ and season‑dependent pattern of favonol glycosides in Cabernet Sauvignon grapevine leaves Sakina Bouderias1,2, Péter Teszlák1, Gábor Jakab1,2 & László Kőrösi1* Flavonols play key roles in many plant defense mechanisms, consequently they are frequently investigated as stress sensitive factors in relation to several oxidative processes. It is well known that grapevine (Vitis vinifera L.) can synthesize various favonol glycosides in the leaves, however, very little information is available regarding their distribution along the cane at diferent leaf levels. In this work, taking into consideration of leaf position, the main favonol glycosides of a red grapevine cultivar (Cabernet Sauvignon) were profled and quantifed by HPLC–DAD analysis. It was found that amount of four favonol glycosides, namely, quercetin-3-O-galactoside, quercetin-3-O-glucoside, kaempferol-3-O-glucoside and kaempferol-3-O-glucuronide decreased towards the shoot tip. Since leaf age also decreases towards the shoot tip, the obtained results suggest that these compounds continuously formed by leaf aging, resulting in their accumulation in the older leaves. In contrast, quercetin-3-O-glucuronide (predominant form) and quercetin-3-O-rutinoside were not accumulated signifcantly by aging. We also pointed out that grapevine boosted the favonol biosynthesis in September, and favonol profle difered signifcantly in the two seasons. Our results contribute to the better understanding of the role of favonols in the antioxidant defense system of grapevine. Flavonoids are very important secondary metabolites, having various functional roles in diferent physiological and developmental processes in plants1–3. Flavonols as a group of favonoids are mainly accumulated in epidermal cells of plant tissues in response to solar radiation 4, 5, to flter the UV-B light while allowing to pass the photo- synthetically active visible light 6–8. -
Quercitrin and Afzelin Isolation: Chemical Synthesis of A
University of Mississippi eGrove Honors College (Sally McDonnell Barksdale Honors Theses Honors College) 2017 Quercitrin and Afzelin Isolation: Chemical Synthesis of a Novel Methicillin-Resistant Staphylococcus Aureus (MRSA) Antibiotic Analogue Taylor Ramsaroop University of Mississippi. Sally McDonnell Barksdale Honors College Follow this and additional works at: https://egrove.olemiss.edu/hon_thesis Part of the Chemistry Commons Recommended Citation Ramsaroop, Taylor, "Quercitrin and Afzelin Isolation: Chemical Synthesis of a Novel Methicillin-Resistant Staphylococcus Aureus (MRSA) Antibiotic Analogue" (2017). Honors Theses. 905. https://egrove.olemiss.edu/hon_thesis/905 This Undergraduate Thesis is brought to you for free and open access by the Honors College (Sally McDonnell Barksdale Honors College) at eGrove. It has been accepted for inclusion in Honors Theses by an authorized administrator of eGrove. For more information, please contact [email protected]. QUERCITRIN AND AFZELIN ISOLATION: CHEMICAL SYNTHESIS OF A NOVEL METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS (MRSA) ANTIBIOTIC ANALOGUE by Taylor Nichole Ramsaroop A thesis submitted to the faculty of The University of Mississippi in partial fulfillment of the requirements of the Sally McDonnell Barksdale Honors College. Oxford May 2017 Approved by ___________________________________ Advisor: Dr. James McChesney ___________________________________ Reader: Dr. Susan Pedigo ___________________________________ Reader: Dr. Nathan Hammer © 2017 Taylor Ramsaroop ii Acknowledgements I would like to thank my thesis advisors for making this project possible and the Sally McDonnell Barksdale Honors College for all the opportunities made available to me throughout my incredible four years at the University of Mississippi. A special thank you to Dr. McChesney for choosing to hire me at Ironstone Separations, Inc two years ago, his continued support, and patience throughout this process. -
Chemistry and Pharmacology of the Kazakh Crataegus Almaatensis Pojark: an Asian Herbal Medicine
antioxidants Article Chemistry and Pharmacology of the Kazakh Crataegus Almaatensis Pojark: An Asian Herbal Medicine 1,2, 3, 1,4,5 3 Sabrina S. Soares y , Elmira Bekbolatova y, Maria Dulce Cotrim , Zuriyadda Sakipova , Liliya Ibragimova 3, Wirginia Kukula-Koch 6,* , Thais B. Sardella Giorno 7, Patrícia D. Fernandes 7, Diogo André Fonseca 1,4,5 and Fabio Boylan 2,* 1 Laboratory of Pharmacy and Pharmaceutical care, Faculty of Pharmacy, University of Coimbra, 3000-548 Coimbra, Portugal 2 School of Pharmacy and Pharmaceutical Sciences & Trinity Biomedical Sciences Institute, Trinity College Dublin, Dublin 2 D02 PN40, Ireland 3 School of Pharmacy, JSC National Medical University, 050000 Almaty, Kazakhstan 4 Coimbra Institute for Clinical and Biomedical Research (iCBR), Faculty of Medicine, University of Coimbra, 3000-548 Coimbra, Portugal 5 CIBB Center for Innovative Biomedicine and Biotechnology, University of Coimbra, 3000-548 Coimbra, Portugal 6 Department of Pharmacognosy with Medicinal Plants Unit, Medical University of Lublin, 1 Chodzki str., 20-093 Lublin, Poland 7 Laboratório da Dor e Inflamação, Universidade Federal do Rio de Janeiro, 21941-902 Rio de Janeiro, Brazil * Correspondence: [email protected] (W.K.-K.); [email protected] (F.B.) Sabrina S. Soares and Elmira Bekbolatova contributed equally to this paper. y Received: 26 June 2019; Accepted: 6 August 2019; Published: 10 August 2019 Abstract: Crataegus almaatensis, an endemic ornamental plant in Kazakhstan is used in popular medicine due to its cardiotonic properties. The most studied species of the same genus are commonly found in Europe, which shows the importance of having the Kazakh species validated via its chemical and pharmacological studies. -
Phenolic Constituentswith Promising Antioxidant and Hepatoprotective
id27907328 pdfMachine by Broadgun Software - a great PDF writer! - a great PDF creator! - http://www.pdfmachine.com http://www.broadgun.com December 2007 Volume 3 Issue 3 NNaattuurraall PPrrAoon dIdnduuian ccJotutrnssal Trade Science Inc. Full Paper NPAIJ, 3(3), 2007 [151-158] Phenolic constituents with promising antioxidant and hepatoprotective activities from the leaves extract of Carya illinoinensis Haidy A.Gad, Nahla A.Ayoub*, Mohamed M.Al-Azizi Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo, (EGYPT) E-mail: [email protected] Received: 15th November, 2007 ; Accepted: 20th November, 2007 ABSTRACT KEYWORDS The aqueous ethanolic leaf extract of Carya illinoinensis Wangenh. K.Koch Carya illinoinensis; (Juglandaceae) showed a significant antioxidant and hepatoprotective Juglandaceae; activities in a dose of 100 mg/ kg body weight. Fifteen phenolic compounds Phenolic compounds; were isolated from the active extract among which ten were identified for Hepatoprotective activity. the first time from Carya illinoinensis . Their structures were elucidated to be gallic acid(1), methyl gallate(2), P-hydroxy benzoic acid(3), 2,3-digalloyl- 4 â 4 -D- C1-glucopyranoside(4), kaempferol-3-O- -D- C1-galactopyranoside, ’-O-galloyl)- 4 trifolin(8), querectin-3-O-(6' -D- C1-galactopyranoside(9), ’-O-galloyl)- 4 kaempferol-3-O-(6' -D- C1-galactopyranoside(10), ellagic acid(11), 3,3' dimethoxyellagic acid(12), epigallocatechin-3-O-gallate(13). Establishment of all structures were based on the conventional methods of analysis and confirmed by NMR spectral analysis. 2007 Trade Science Inc. - INDIA INTRODUCTION dition, caryatin(quercetin-3,5-dimethyl ether) , caryatin glucoside and rhamnoglucoside were also isolated from Family Juglandaceae includes the deciduous gen- the bark[4], while, quercetin glycoside, galactoside, rham- era, Juglans(walnuts) and Carya(hickories). -
Download Product Insert (PDF)
PRODUCT INFORMATION Quercitrin Item No. 19866 CAS Registry No.: 522-12-3 OH Formal Name: 3-[(6-deoxy-ɑ-L-mannopyranosyl) oxy]-2-(3,4-dihydroxyphenyl)-5,7- OH dihydroxy-4H-1-benzopyran-4-one Synonyms: C.I. 75720, NSC 9221, HO O Quercetin 3-rhamnoside Quercetin 3-L-rhamnoside O MF: C21H20O11 O FW: 448.4 OH HO Purity: ≥98% O UV/Vis.: λmax: 254, 351 nm Supplied as: A crystalline solid OH Storage: -20°C OH Stability: As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly Laboratory Procedures Quercitrin is supplied as a crystalline solid. A stock solution may be made by dissolving the quercitrin in the solvent of choice. Quercitrin is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of quercitrin in these solvents is approximately 1, 30, and 15 mg/ml, respectively. Quercitrin is sparingly soluble in aqueous solutions. To enhance aqueous solubility, dilute the organic solvent solution into aqueous buffers or isotonic saline. If performing biological experiments, ensure the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. We do not recommend storing the aqueous solution for more than one day. Description Quercitrin is a glycoside formed from the flavonoid quercetin (Item No. 10005169) and the deoxy sugar rhamnose. It can be found in a wide range of medicinal plants and has been reported to have antioxidant, antiviral, and anti-inflammatory properties.1,2,3 References 1. -
(12) United States Patent (10) Patent No.: US 7,399,783 B2 Rosenbloom (45) Date of Patent: Jul
US007399.783B2 (12) United States Patent (10) Patent No.: US 7,399,783 B2 Rosenbloom (45) Date of Patent: Jul. 15, 2008 (54) METHODS FOR THE TREATMENT OF SCAR Quercetin: Implications for the Treatment of Excessive Scars.” TSSUE Internet Web Page, vol. 57(5); Nov. 2004. Marilyn Sterling, R.D., Article: Science Beat, Internet Web Page, (75) Inventor: Richard A. Rosenbloom, Elkins Park, Natural Foods Merchandiser vol. XXIV, No. 10, p. 50, 2003. PA (US) Phan TT. See P. Tran E. Nguyen TT, Chan SY. Lee ST and Huynh H., PubMed, Internet Web Page, “Suppression of Insulin-like Growth (73) Assignee: The Quigley Corporation, Doylestown, Factor Signalling Pathway and Collagen Expression in Keloid-De rived Fibroblasts by Quercetin: It's Therapeutic Potential Use in the PA (US) Treatment and/or Prevention of Keloids.” Br. J. Dermatol., Mar. 2003, 148(3):544-52. (*) Notice: Subject to any disclaimer, the term of this Crystal Smith, Kevin A. Lombard, Ellen B. Peffley and Weixin Liu; patent is extended or adjusted under 35 "Genetic Analysis of Quercetin in Onion (Allium cepa L.) Lady U.S.C. 154(b) by 440 days. Raider.” The Texas Journal of Agriculture and Natural Resource, vol. 16 pp. 24-28, 2003. (21) Appl. No.: 11/158,986 Skin Actives Scientific L.L.C., Internet Web Page, “Quercetin.” Quercetin by Skinactives, printed on Apr. 10, 2006. (22) Filed: Jun. 22, 2005 Saulis, Alexandrina S. M.D.; Mogford, Jon H. Ph.D.; Mustoe, Tho mas A., M.D., Plastic and Reconstructive Surgery, “Effect of (65) Prior Publication Data Mederma on Hypertrophic Scarring in the Rabbit Ear Model.” Jour US 2006/O293257 A1 Dec. -
Synthesis, in Vitro Biological Evaluation, and Oxidative Transformation of New Flavonol Derivatives: the Possible Role of the Phenyl-N,N- Dimethylamino Group
Article Synthesis, in Vitro Biological Evaluation, and Oxidative Transformation of New Flavonol Derivatives: The Possible Role of the Phenyl-N,N- Dimethylamino Group Peter Szabados-Furjesi 1, David Pajtas 2, Aliz Barta 2, Evelin Csepanyi 1, Attila Kiss-Szikszai 3, Arpad Tosaki 4 and Istvan Bak 1,* 1 Department of Bioanalytical Chemistry, Faculty of Pharmacy, University of Debrecen, Debrecen H-4032, Hungary; [email protected] (P.S.-F.); [email protected] (E.C.) 2 Department of Biophysics and Cell Biology, Faculty of Medicine, University of Debrecen, Debrecen H- 4032, Hungary; [email protected] (D.P.); [email protected] (A.B.) 3 Department of Organic Chemistry, Faculty of Science and Technology, University of Debrecen, Debrecen Debrecen H-4032, Hungary; [email protected] 4 Department of Pharmacology, Faculty of Pharmacy, University of Debrecen, Debrecen H-4032, Hungary; [email protected] * Correspondence: [email protected]; Tel./Fax: 00-36-52-255-586 Academic Editor: Luciano Saso Received: 13 November 2018; Accepted: 29 November 2018; Published: 30 November 2018 Abstract: Six new flavonols (6a–f) were synthesized with Claisen–Schmidt and Suzuki reactions and they were fully characterized by spectroscopic methods. In order to evaluate their antioxidant activities, their oxygen radical absorption capacity and ferric reducing antioxidant power were measured, along with their free radical scavenging activity against 2,2’-azino-bis(3- ethylbenzothiazoline-6-sulphonic acid) and 2,2-diphenyl-1-picrylhydrazylradicals. In addition, their cytotoxicity on H9c2 cardiomyoblast cells was also assessed by a 3-(4,5-dimethylthiazol-2-yl)- 2,5-diphenyltetrazolium bromide assay. -
Asteraceae)§ Karin M.Valant-Vetscheraa and Eckhard Wollenweberb,*
Chemodiversity of Exudate Flavonoids in Seven Tribes of Cichorioideae and Asteroideae (Asteraceae)§ Karin M.Valant-Vetscheraa and Eckhard Wollenweberb,* a Department of Plant Systematics and Evolution Ð Comparative and Ecological Phytochemistry, University of Vienna, Rennweg 14, A-1030 Wien, Austria b Institut für Botanik der TU Darmstadt, Schnittspahnstrasse 3, D-64287 Darmstadt, Germany. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 62c, 155Ð163 (2007); received October 26/November 24, 2006 Members of several genera of Asteraceae, belonging to the tribes Mutisieae, Cardueae, Lactuceae (all subfamily Cichorioideae), and of Astereae, Senecioneae, Helenieae and Helian- theae (all subfamily Asteroideae) have been analyzed for chemodiversity of their exudate flavonoid profiles. The majority of structures found were flavones and flavonols, sometimes with 6- and/or 8-substitution, and with a varying degree of oxidation and methylation. Flava- nones were observed in exudates of some genera, and, in some cases, also flavonol- and flavone glycosides were detected. This was mostly the case when exudates were poor both in yield and chemical complexity. Structurally diverse profiles are found particularly within Astereae and Heliantheae. The tribes in the subfamily Cichorioideae exhibited less complex flavonoid profiles. Current results are compared to literature data, and botanical information is included on the studied taxa. Key words: Asteraceae, Exudates, Flavonoids Introduction comparison of accumulation trends in terms of The family of Asteraceae is distributed world- substitution patterns is more indicative for che- wide and comprises 17 tribes, of which Mutisieae, modiversity than single compounds. Cardueae, Lactuceae, Vernonieae, Liabeae, and Earlier, we have shown that some accumulation Arctoteae are grouped within subfamily Cichori- tendencies apparently exist in single tribes (Wol- oideae, whereas Inuleae, Plucheae, Gnaphalieae, lenweber and Valant-Vetschera, 1996). -
Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 600-OH Group
molecules Article Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 600-OH Group Xican Li 1,*, Qian Jiang 1, Tingting Wang 1, Jingjing Liu 1 and Dongfeng Chen 2,* 1 School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China; [email protected] (Q.J.); [email protected] (T.W.); [email protected] (J.L.) 2 School of Basic Medical Science, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China * Correspondence: [email protected] or [email protected] (X.L.); [email protected] (D.C.); Tel.: +86-203-935-8076 (X.L.) Academic Editor: Maurizio Battino Received: 6 July 2016; Accepted: 6 September 2016; Published: 19 September 2016 Abstract: The role of the 600-OH (!-OH) group in the antioxidant activity of flavonoid glycosides has been largely overlooked. Herein, we selected quercitrin (quercetin-3-O-rhamnoside) and isoquercitrin (quercetin-3-O-glucoside) as model compounds to investigate the role of the 600-OH group in several antioxidant pathways, including Fe2+-binding, hydrogen-donating (H-donating), and electron-transfer (ET). The results revealed that quercitrin and isoquercitrin both exhibited dose-dependent antioxidant activities. However, isoquercitrin showed higher levels of activity than quercitrin in the Fe2+-binding, ET-based ferric ion reducing antioxidant power, and multi-pathways-based superoxide anion-scavenging assays. In contrast, quercitrin exhibited greater activity than isoquercitrin in an H-donating-based 1,1-diphenyl-2-picrylhydrazyl radical-scavenging assay.