Antiviral Activities of Oleanolic Acid and Its Analogues
Total Page:16
File Type:pdf, Size:1020Kb
Load more
Recommended publications
-
Intestinal Anti-Inflammatory Activity of Terpenes in Experimental Models
molecules Review Intestinal Anti-Inflammatory Activity of Terpenes in Experimental Models (2010–2020): A Review Maria Elaine Araruna 1, Catarina Serafim 1, Edvaldo Alves Júnior 1, Clelia Hiruma-Lima 2, Margareth Diniz 1,3 and Leônia Batista 1,3,* 1 Postgraduate Program in Natural Products and Bioactive Synthetic, Health Sciences Center, Federal University of Paraiba, João Pessoa 58051-900, PB, Brazil; [email protected] (M.E.A.); [email protected] (C.S.); [email protected] (E.A.J.); [email protected] (M.D.) 2 Department of Structural and Functional Biology (Physiology), Institute of Biosciences, São Paulo State University, Botucatu 18618-970, SP, Brazil; [email protected] 3 Department of Pharmacy, Health Sciences Center, Federal University of Paraíba, João Pessoa 58051-900, PB, Brazil * Correspondence: [email protected]; Tel.: +55-83-32167003; Fax: +55-83-32167502 Academic Editors: Maurizio Battino, Jesus Simal-Gandara and Esra Capanoglu Received: 8 September 2020; Accepted: 28 September 2020; Published: 20 November 2020 Abstract: Inflammatory bowel diseases (IBDs) refer to a group of disorders characterized by inflammation in the mucosa of the gastrointestinal tract, which mainly comprises Crohn’s disease (CD) and ulcerative colitis (UC). IBDs are characterized by inflammation of the intestinal mucosa, are highly debilitating, and are without a definitive cure. Their pathogenesis has not yet been fully elucidated; however, it is assumed that genetic, immunological, and environmental factors are involved. People affected by IBDs have relapses, and therapeutic regimens are not always able to keep symptoms in remission over the long term. Natural products emerge as an alternative for the development of new drugs; bioactive compounds are promising in the treatment of several disorders, among them those that affect the gastrointestinal tract, due to their wide structural diversity and biological activities. -
Betulinic Acid and Its Derivatives As Anti-Cancer Agent: a Review
Available online a t www.scholarsresearchlibrary.com Scholars Research Library Archives of Applied Science Research, 2014, 6 (3):47-58 (http://scholarsresearchlibrary.com/archive.html) ISSN 0975-508X CODEN (USA) AASRC9 Betulinic acid and its derivatives as anti-cancer agent: A review Gomathi Periasamy*, Girma Teketelew, Mebrahtom Gebrelibanos, Biruk Sintayehu, Michael Gebrehiwot, Aman Karim and Gereziher Geremedhin Department of Pharmacy, College of Health Sciences, Mekelle University, Mekelle, Ethiopia _____________________________________________________________________________________________ ABSTRACT Betulinic acid is a known natural product which has gained a lot of attention in the recent years since it exhibits a variety of biological and medicinal properties. This review provides the most important anticancer properties of betulinic acid and its derivatives. _____________________________________________________________________________________________ INTRODUCTION Cancer is a group of diseases that cause cells in the body to change and grow out of control[1]. Cancer cell growth is different from normal cell growth. Instead of dying, cancer cells keep on growing and form new cancer cells. These cancer cells can grow into (invade) other tissues, something that normal cells cannot do. In most cases the cancer cells form a tumor. But some cancers, like leukemia, rarely form tumors. Instead, these cancer cells are in the blood and bone marrow[2]. Cancer cell escape from many of the normal homeostatic mechanism that control proliferation. They invade surrounding tissues, gets into the body’s circulating system and set up areas of proliferation away from the site of their original appearance[3]. Cancer is the second most important disease leading to death in both the developing and developed countries nowadays. The global burden of cancer continues to increase largely because of the aging and growth of the world population alongside an increasing adoption of cancer-causing behaviors, particularly smoking, in economically developing countries[4]. -
Possible Fungistatic Implications of Betulin Presence in Betulaceae Plants and Their Hymenochaetaceae Parasitic Fungi Izabela Jasicka-Misiak*, Jacek Lipok, Izabela A
Possible Fungistatic Implications of Betulin Presence in Betulaceae Plants and their Hymenochaetaceae Parasitic Fungi Izabela Jasicka-Misiak*, Jacek Lipok, Izabela A. S´wider, and Paweł Kafarski Faculty of Chemistry, Opole University, Oleska 48, 45-052 Opole, Poland. Fax: +4 87 74 52 71 15. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 65 c, 201 – 206 (2010); received September 23/October 26, 2009 Betulin and its derivatives (especially betulinic acid) are known to possess very interesting prospects for their application in medicine, cosmetics and as bioactive agents in pharmaceu- tical industry. Usually betulin is obtained by extraction from the outer layer of a birch bark. In this work we describe a simple method of betulin isolation from bark of various species of Betulaceae trees and parasitic Hymenochaetaceae fungi associated with these trees. The composition of the extracts was studied by GC-MS, whereas the structures of the isolated compounds were confi rmed by FTIR and 1H NMR. Additionally, the signifi cant fungistatic activity of betulin towards some fi lamentous fungi was determined. This activity was found to be strongly dependent on the formulation of this triterpene. A betulin-trimyristin emul- sion, in which nutmeg fat acts as emulsifi er and lipophilic carrier, inhibited the fungal growth even in micromolar concentrations – its EC50 values were established in the range of 15 up to 50 μM depending on the sensitivity of the fungal strain. Considering the lack of fungistatic effect of betulin applied alone, the application of ultrasonic emulsifi cation with the natural plant fat trimyristin appeared to be a new method of antifungal bioassay of water-insoluble substances, such as betulin. -
Assessment of Betulinic Acid Cytotoxicity and Mitochondrial Metabolism Impairment in a Human Melanoma Cell Line
International Journal of Molecular Sciences Article Assessment of Betulinic Acid Cytotoxicity and Mitochondrial Metabolism Impairment in a Human Melanoma Cell Line Dorina Coricovac 1,2,† , Cristina Adriana Dehelean 1,2,†, Iulia Pinzaru 1,2,* , Alexandra Mioc 1,2,*, Oana-Maria Aburel 3,4, Ioana Macasoi 1,2, George Andrei Draghici 1,2 , Crina Petean 1, Codruta Soica 1,2, Madalina Boruga 3, Brigitha Vlaicu 3 and Mirela Danina Muntean 3,4 1 Faculty of Pharmacy, “Victor Babes, ” University of Medicine and Pharmacy Timis, oara, Eftimie Murgu Square No. 2, RO-300041 Timis, oara, Romania; [email protected] (D.C.); [email protected] (C.A.D.); [email protected] (I.M.); [email protected] (G.A.D.); [email protected] (C.P.); [email protected] (C.S.) 2 Research Center for Pharmaco-toxicological Evaluations, Faculty of Pharmacy, “Victor Babes” University of Medicine and Pharmacy Timis, oara, Eftimie Murgu Square No. 2, RO-300041 Timis, oara, Romania 3 Faculty of Medicine “Victor Babes, ” University of Medicine and Pharmacy Timis, oara, Eftimie Murgu Square No. 2, RO-300041 Timis, oara, Romania; [email protected] (O.-M.A.); [email protected] (M.B.); [email protected] (B.V.); [email protected] (M.D.M.) 4 Center for Translational Research and Systems Medicine, Faculty of Medicine,” Victor Babes, ” University of Medicine and Pharmacy Timis, oara, Eftimie Murgu Sq. no. 2, RO-300041 Timis, oara, Romania * Correspondence: [email protected] (I.P.); [email protected] (A.M.); Tel.: +40-256-494-604 † Authors with equal contribution. Citation: Coricovac, D.; Dehelean, Abstract: Melanoma represents one of the most aggressive and drug resistant skin cancers with C.A.; Pinzaru, I.; Mioc, A.; Aburel, poor prognosis in its advanced stages. -
Plant-Derived Triterpenoid Biomarkers and Their Applications In
Plant-derived triterpeonid biomarkers: chemotaxonomy, geological alteration, and vegetation reconstruction Res. Org. Geochem. 35, 11 − 35 (2019) Reviews-2015 Taguchi Award Plant-derived triterpenoid biomarkers and their applications in paleoenvironmental reconstructions: chemotaxonomy, geological alteration, and vegetation reconstruction Hideto Nakamura* (Received November 22, 2019; Accepted December 27, 2019) Abstract Triterpenoids and their derivatives are ubiquitous in sediment samples. Land plants are major sources of non- hopanoid triterpenoids; these terpenoids comprise a vast number of chemotaxonomically distinct biomolecules. Hence, geologically occurring plant-derived triterpenoids (geoterpenoids) potentially record unique characteristics of paleovegetation and sedimentary environments, and serve as source-specific markers for studying paleoenviron- ments. This review is aimed at explaining the origin of triterpenoids and their use as biomarkers in elucidating paleo- environments. Herein, application of plant-derived triterpenoids is discussed in terms of: (i) their biosynthetic pathways. These compounds are primarily synthesized via oxidosqualene cyclase (OSCs) and serve as precursors for a variety of membrane sterols and steroid hormones. Studies on OSCs and resulting compounds have helped elucidate the diversity and origin of the parent terpenoids. (ii) their chemotaxonomic significance. Geochemically important classes of triterpenoid skeletons are useful in gathering and substantiating information on botanical ori- gin of -
Review Article Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development
Hindawi Publishing Corporation Evidence-Based Complementary and Alternative Medicine Volume 2015, Article ID 238482, 26 pages http://dx.doi.org/10.1155/2015/238482 Review Article Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development Charu Sharma,1 Bassem Sadek,2 Sameer N. Goyal,3 Satyesh Sinha,4 Mohammad Amjad Kamal,5,6 and Shreesh Ojha2 1 Department of Internal Medicine, College of Medicine and Health Sciences, United Arab Emirates University, P.O. Box 17666, Al Ain, Abu Dhabi, UAE 2Department of Pharmacology and Therapeutics, College of Medicine and Health Sciences, United Arab Emirates University, P.O. Box 17666, Al Ain, Abu Dhabi, UAE 3DepartmentofPharmacology,R.C.PatelInstituteofPharmaceuticalEducation&Research,Shirpur,Mahrastra425405,India 4Department of Internal Medicine, College of Medicine, Charles R. Drew University of Medicine and Science, Los Angeles, CA 90059, USA 5King Fahd Medical Research Center, King Abdulaziz University, Jeddah, Saudi Arabia 6Enzymoics, 7 Peterlee Place, Hebersham, NSW 2770, Australia Correspondence should be addressed to Shreesh Ojha; [email protected] Received 24 April 2015; Accepted 24 August 2015 Academic Editor: Ki-Wan Oh Copyright © 2015 Charu Sharma et al. 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. The cannabinoid molecules are derived from Cannabis sativa plant which acts on the cannabinoid receptors types 1 and 2 (CB1 and CB2) which have been explored as potential therapeutic targets for drug discovery and development. Currently, there are 9 numerous cannabinoid based synthetic drugs used in clinical practice like the popular ones such as nabilone, dronabinol, and Δ - tetrahydrocannabinol mediates its action through CB1/CB2 receptors. -
Integrated Metabolomics and Transcriptomics Study of Traditional Herb Astragalus Membranaceus Bge. Var. Mongolicus
Wu et al. BMC Genomics 2020, 21(Suppl 10):697 https://doi.org/10.1186/s12864-020-07005-y RESEARCH Open Access Integrated metabolomics and transcriptomics study of traditional herb Astragalus membranaceus Bge. var. mongolicus (Bge.) Hsiao reveals global metabolic profile and novel phytochemical ingredients Xueting Wu1†, Xuetong Li1,2†, Wei Wang3†, Yuanhong Shan1, Cuiting Wang1, Mulan Zhu1,4, Qiong La5, Yang Zhong3,5,YeXu6*, Peng Nan3* and Xuan Li1,2* From The 18th Asia Pacific Bioinformatics Conference Seoul, Korea. 18-20 August 2020 Abstract Background: Astragalus membranaceus Bge. var. mongolicus (Bge.) Hsiao is one of the most common herbs widely used in South and East Asia, to enhance people’s health and reinforce vital energy. Despite its prevalence, however, the knowledge about phytochemical compositions and metabolite biosynthesis in Astragalus membranaceus Bge. var. mongolicus (Bge.) Hsiao is very limited. (Continued on next page) * Correspondence: [email protected]; [email protected]; [email protected] †Xueting Wu, Xuetong Li and Wei Wang contributed equally to this work. 6Department of Colorectal Surgery, Fudan University Shanghai Cancer Center, Shanghai, China 3Ministry of Education Key Laboratory for Biodiversity Science and Ecological Engineering, School of Life Sciences, Fudan University, Shanghai 200438, China 1Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Institute of Plant Physiology and Ecology, Chinese Academy of Sciences, Shanghai 200032, China Full list of author information is available at the end of the article © The Author(s). 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. -
Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: a Route to New Bioactive Compounds
Review Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds Joana L. C. Sousa 1,2,*, Carmen S. R. Freire 2, Armando J. D. Silvestre 2 and Artur M. S. Silva 1,* 1 QOPNA & LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal 2 CICECO, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal; [email protected] (C.S.R.F.); [email protected] (A.J.D.S.) * Correspondence: [email protected] (J.L.C.S.); [email protected] (A.M.S.S.); Tel.: +351-234-370-714 (A.M.S.S.) Received: 29 December 2018; Accepted: 17 January 2019; Published: 19 January 2019 Abstract: Betulinic acid (BA) and its natural analogues betulin (BN), betulonic (BoA), and 23- hydroxybetulinic (HBA) acids are lupane-type pentacyclic triterpenoids. They are present in many plants and display important biological activities. This review focuses on the chemical transformations used to functionalize BA/BN/BoA/HBA in order to obtain new derivatives with improved biological activity, covering the period since 2013 to 2018. It is divided by the main chemical transformations reported in the literature, including amination, esterification, alkylation, sulfonation, copper(I)-catalyzed alkyne-azide cycloaddition, palladium-catalyzed cross-coupling, hydroxylation, and aldol condensation reactions. In addition, the synthesis of heterocycle-fused BA/HBA derivatives and polymer‒BA conjugates are also addressed. The new derivatives are mainly used as antitumor agents, but there are other biological applications such as antimalarial activity, drug delivery, bioimaging, among others. Keywords: triterpenes; betulinic acid; betulin; betulonic acid; 23-hydroxybetulinic acid; synthesis; functionalization; derivatization 1. -
Phytochemicals
Phytochemicals HO O OH CH OC(CH3)3 3 CH3 CH3 H H O NH O CH3 O O O O OH O CH3 CH3 OH CH3 N N O O O N N CH3 OH HO OH HO Alkaloids Steroids Terpenoids Phenylpropanoids Polyphenols Others Phytochemicals Phytochemical is a general term for natural botanical chemicals Asiatic Acid [A2475] is a pentacyclic triterpene extracted from found in, for example, fruits and vegetables. Phytochemicals are Centella asiatica which is a tropical medicinal plant. Asiatic Acid not necessary for human metabolism, in contrast to proteins, possess wide pharmacological activities. sugars and other essential nutrients, but it is believed that CH3 phytochemicals affect human health. Phytochemicals are CH3 components of herbs and crude drugs used since antiquity by humans, and significant research into phytochemicals continues today. H C CH H C OH HO 3 3 O Atropine [A0754], a tropane alkaloid, was first extracted from H CH3 the root of belladonna (Atropa belladonna) in 1830s. Atropine is a HO competitive antagonist of muscarine-like actions of acetylcholine CH3 H and is therefore classified as an antimuscarinic agent. OH [A2475] O NCH3 O C CHCH2OH Curcumin [C0434] [C2302], a dietary constituent of turmeric, has chemopreventive and chemotherapeutic potentials against various types of cancers. OO CH3O OCH3 [A0754] HO OH Galantamine Hydrobromide [G0293] is a tertiary alkaloid [C0434] [C2302] found in the bulbs of Galanthus woronowi. Galantamine has shown potential for the treatment of Alzheimer's disease. TCI provides many phytochemicals such as alkaloids, steroids, terpenoids, phenylpropanoids, polyphenols and etc. OH References O . HBr Phytochemistry of Medicinal Plants, ed. -
Naturally Occurring Saponins: Chemistry and Biology
Journal of Poisonous and Medicinal Plant Research Vol. 1(1), pp. 001-006, May, 2013 Available online at http://www.apexjournal.org ISSN 2315-8834© 2013 Apex Journal International Review Naturally occurring saponins: Chemistry and biology J. S. Negi 1*, P. S. Negi 2, G. J. Pant 2, M. S. M. Rawat 2, S. K. Negi 3 1Herbal Research and Development Institute, Mandal, Gopeshwar (Chamoli) - 246 401, Uttarakhand, India. 2Department of Chemistry, HNB Garhwal University, Srinagar (Garhwal)- 246 174, Uttarakhand, India. 3Department of Botany, HNB Garhwal University, Srinagar (Garhwal) - 246 174, Uttarakhand, India. Accepted 2 April, 2013 Naturally occurring saponins are glycosides of steroids, alkaloids and triterpenoids. They are widely distributed in nature and reported to be present in 500 genera of plants. A wide variety of plants belonging to family Liliaceae, Dioscoreaceae, Solanaceae, Sapindaceae and Agavaceae are the major source of saponins. They are amorphous substances having high molecular weight and are soluble in water and alcohol to produce foam but organic solvents inhibit their foaming property. Plants saponins are generally extracted into butanol through liquid-liquid partition and separated through column chromatography using silica gel as adsorbent and chloroform: methanol as mobile phase. HPLC, GC, Sephadex LH-20 Chromatography, DCCC, preparative paper chromatography and TLC were also used for the separation and isolation of saponins. The structures of saponins were determined by several spectroscopic techniques, viz., UV, IR, 1H NMR, 13 C NMR and Mass spectroscopy. Saponins possess several biological activities such as antioxidant, immunostimulant, antihepatotoxic, antibacterial, anticarcinogenic, antidiarrheal, antiulcerogenic, antioxytoxic, antihypoglycemic, anticytotoxic and antimolluscicidal. Saponins are biologically synthesized by C5 isoprene units through cytosolic mevalonate pathway. -
Biocatalysis in the Chemistry of Lupane Triterpenoids
molecules Review Biocatalysis in the Chemistry of Lupane Triterpenoids Jan Bachoˇrík 1 and Milan Urban 2,* 1 Department of Organic Chemistry, Faculty of Science, Palacký University in Olomouc, 17. listopadu 12, 771 46 Olomouc, Czech Republic; [email protected] 2 Medicinal Chemistry, Faculty of Medicine and Dentistry, Institute of Molecular and Translational Medicine, Palacký University in Olomouc, Hnˇevotínská 5, 779 00 Olomouc, Czech Republic * Correspondence: [email protected] Abstract: Pentacyclic triterpenes are important representatives of natural products that exhibit a wide variety of biological activities. These activities suggest that these compounds may represent potential medicines for the treatment of cancer and viral, bacterial, or protozoal infections. Naturally occurring triterpenes usually have several drawbacks, such as limited activity and insufficient solubility and bioavailability; therefore, they need to be modified to obtain compounds suitable for drug development. Modifications can be achieved either by methods of standard organic synthesis or with the use of biocatalysts, such as enzymes or enzyme systems within living organisms. In most cases, these modifications result in the preparation of esters, amides, saponins, or sugar conjugates. Notably, while standard organic synthesis has been heavily used and developed, the use of the latter methodology has been rather limited, but it appears that biocatalysis has recently sparked considerably wider interest within the scientific community. Among triterpenes, derivatives of lupane play important roles. This review therefore summarizes the natural occurrence and sources of lupane triterpenoids, their biosynthesis, and semisynthetic methods that may be used for the production of betulinic acid from abundant and inexpensive betulin. Most importantly, this article compares chemical transformations of lupane triterpenoids with analogous reactions performed by Citation: Bachoˇrík,J.; Urban, M. -
Oil–Source Correlation Studies in the Shallow Berea Sandstone
Oil–source correlation studies in AUTHORS the shallow Berea Sandstone Paul C. Hackley ~ US Geological Survey (USGS), Reston, Virginia; phackley@ petroleum system, eastern usgs.gov Paul C. Hackley is a research geologist at USGS in Reston, Virginia, where he oversees the Kentucky Organic Petrology Laboratory. He holds degrees from Shippensburg University (B.A.), Paul C. Hackley, Thomas M. (Marty) Parris, George Washington University (M.Sc.), and Cortland F. Eble, Stephen F. Greb, and David C. Harris George Mason University (Ph.D.). His primary research interests are in organic petrology and its application to fossil fuel assessment. Thomas M. (Marty) Parris ~ ABSTRACT Kentucky Geological Survey (KGS), University of Shallow production of sweet high-gravity oil from the Up- Kentucky, Lexington, Kentucky; mparris@ per Devonian Berea Sandstone in northeastern Kentucky has uky.edu caused the region to become the leading oil producer in the state. Thomas M. (Marty) Parris is a research Potential nearby source rocks, namely, the overlying Mississip- geologist at KGS, University of Kentucky, where pian Sunbury Shale and underlying Ohio Shale, are immature he uses gas and aqueous fluid geochemistry to for commercial oil generation according to vitrinite reflectance conduct research on petroleum systems, basin fl fl andprogrammedpyrolysisanalyses.Weusedorganicgeo- uid ow, diagenesis, and the environmental chemical measurements from Berea oils and solvent extracts impacts of energy development. He received his Ph.D. from the University of California, from potential Upper Devonian–Mississippian source rocks to – – Santa Barbara, and B.S. degree from better understand organic matter sources, oil oil and oil source Tennessee Tech University. rock correlations, and thermal maturity in the shallow Berea oil play.