Oil–Source Correlation Studies in the Shallow Berea Sandstone
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Antiviral Activities of Oleanolic Acid and Its Analogues
molecules Review Antiviral Activities of Oleanolic Acid and Its Analogues Vuyolwethu Khwaza, Opeoluwa O. Oyedeji and Blessing A. Aderibigbe * Department of Chemistry, University of Fort Hare, Alice Campus, Alice 5700, Eastern Cape, South Africa; [email protected] (V.K.); [email protected] (O.O.O) * Correspondence: [email protected]; Tel.: +27-406022266; Fax: +08-67301846 Academic Editors: Patrizia Ciminiello, Alfonso Mangoni, Marialuisa Menna and Orazio Taglialatela-Scafati Received: 27 July 2018; Accepted: 5 September 2018; Published: 9 September 2018 Abstract: Viral diseases, such as human immune deficiency virus (HIV), influenza, hepatitis, and herpes, are the leading causes of human death in the world. The shortage of effective vaccines or therapeutics for the prevention and treatment of the numerous viral infections, and the great increase in the number of new drug-resistant viruses, indicate that there is a great need for the development of novel and potent antiviral drugs. Natural products are one of the most valuable sources for drug discovery. Most natural triterpenoids, such as oleanolic acid (OA), possess notable antiviral activity. Therefore, it is important to validate how plant isolates, such as OA and its analogues, can improve and produce potent drugs for the treatment of viral disease. This article reports a review of the analogues of oleanolic acid and their selected pathogenic antiviral activities, which include HIV, the influenza virus, hepatitis B and C viruses, and herpes viruses. Keywords: HIV; influenza virus; HBV/HCV; natural product; triterpenoids; medicinal plant 1. Introduction Viral diseases remain a major problem for humankind. It has been reported in some reviews that there is an increase in the number of viral diseases responsible for death and morbidity around the world [1,2]. -
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 -
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. -
Geochemical Characterization of the Eocene Coal-Bearing Source
minerals Article Geochemical Characterization of the Eocene Coal-Bearing Source Rocks, Xihu Sag, East China Sea Shelf Basin, China: Implications for Origin and Depositional Environment of Organic Matter and Hydrocarbon Potential Xiong Cheng 1,2,* , Dujie Hou 1,2,*, Xinhuai Zhou 3, Jinshui Liu 4, Hui Diao 4 and Lin Wei 1,2 1 School of Energy Resources, China University of Geosciences, Beijing 100083, China; [email protected] 2 Key Laboratory of Marine Reservoir Evolution and Hydrocarbon Accumulation Mechanism, Ministry of Education, Beijing 100083, China 3 Hainan Branch of China National Offshore Oil Corporation, Haikou 570100, China; [email protected] 4 Shanghai Branch of China National Offshore Oil Corporation, Shanghai 200050, China; [email protected] (J.L.); [email protected] (H.D.) * Correspondence: [email protected] (X.C.); [email protected] (D.H.) Abstract: Eocene coal-bearing source rocks of the Pinghu Formation from the W-3 well in the western margin of the Xihu Sag, East China Sea Shelf Basin were analyzed using Rock-Eval pyrolysis and gas Citation: Cheng, X.; Hou, D.; Zhou, chromatography–mass spectrometry to investigate the samples’ source of organic matter, depositional X.; Liu, J.; Diao, H.; Wei, L. environment, thermal maturity, and hydrocarbon generative potential. The distribution patterns of Geochemical Characterization of the n-alkanes, isoprenoids and steranes, high Pr/Ph ratios, abundant diterpanes, and the presence of non- Eocene Coal-Bearing Source Rocks, hopanoid triterpanes indicate predominant source input from higher land plants. The contribution of Xihu Sag, East China Sea Shelf Basin, aquatic organic matter was occasionally slightly elevated probably due to a raised water table. -
Ethnomedicinal Plants Used Against Jaundice in Bangladesh and Its Economical Prospects
Bulletin of Pharmaceutical Research 2012;2(2):91-105 An Official Publication of Association of Pharmacy Professionals ISSN: 2249-6041 (Print); ISSN: 2249-9245 (Online) REVIEW ARTICLE ETHNOMEDICINAL PLANTS USED AGAINST JAUNDICE IN BANGLADESH AND ITS ECONOMICAL PROSPECTS Zahed Bin Rahim*, Muhammad Mahabubur Rahman, Dibyajyoti Saha, S.M. Zahid Hosen, Swati Paul and Shafiul Kader Department of Pharmacy, BGC Trust University, Chittagong, Bangladesh *E-mails: [email protected], [email protected] Tel.: +88-01755588624, +88-01752560434, +88-01715847075. Received: January 06, 2012 / Revised: July 28, 2012 / Accepted: July 29, 2012 In Bangladesh, traditional plant-based medicines have always been used to treat hepatitis and jaundice. In the present work, we focused on medicinal plants used to treat jaundice and hepatitis. About 95 plant species belonging to about 75 family were found to be used against jaundice or hepatitis by the traditional healers. The most important plant species are Alocasia indica, Aloe barbadensis, Asparagus racemosus, Averrhoa carambola, Bixa orellana, Boerhaavia diffusa, Cucumis sativus, Cajanus Cajan, Cassia fistula, Eclipta alba, Hemidesmus indicus, Lagenaria siceraria, Mentha arvensis, Momordica charantea, Oroxylum indicum, Saccharum officinarum, Tamarindus indica etc. The ethnomedicinal inventory is presented by plant name, local name, family, chemical constituents, parts used and distribution in Bangladesh. Key words: Ethnomedicinal plants, Jaundice, Hepatitis, Economical prospects. INTRODUCTION the skin, sclera and mucous membrane, it turns Ethnomedicine is a subfield of ethno botany or yellow. This yellowness is known as jaundice medical anthropology that deals with the study (icterus) and usually detectable when plasma of traditional medicines; not only those that have bilirubin is greater than 2 mg/dl (34 µmol/l). -
NIH Public Access Author Manuscript Nat Prod Rep
NIH Public Access Author Manuscript Nat Prod Rep. Author manuscript; available in PMC 2013 September 16. NIH-PA Author ManuscriptPublished NIH-PA Author Manuscript in final edited NIH-PA Author Manuscript form as: Nat Prod Rep. 2009 October ; 26(10): 1321–1344. doi:10.1039/b810774m. Plant-derived triterpenoids and analogues as antitumor and anti- HIV agents† Reen-Yen Kuo, Keduo Qian, Susan L. Morris-Natschke, and Kuo-Hsiung Lee* Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599-7568, USA. Abstract This article reviews the antitumor and anti-HIV activities of naturally occurring triterpenoids, including the lupane, ursane, oleanane, lanostane, dammarane, and miscellaneous scaffolds. Structure–activity relationships of selected natural compounds and their synthetic derivatives are also discussed. 1 Introduction Natural products are an excellent reservoir of biologically active compounds. For centuries, extracts from natural products have been a main source of folk medicines, and even today, many cultures still employ them directly for medicinal purposes. Among the classes of identified natural products, triterpenoids, one of the largest families, have been studied intensively for their diverse structures and variety of biological activities. As a continued study of naturally occurring drug candidates, this review describes the research progress over the last three years (2006–2008) on triterpenoids possessing cytotoxic or anti-HIV activity, with focus on the occurrence, biological activities, and structure–activity relationships of selected compounds and their synthetic derivatives. 2 Potential antitumor effects of triterpenoids 2.1 The lupane group Betulinic acid (1) is a naturally occurring pentacyclic triterpene belonging to the lupane family. -
Open Natural Products Research: Curation and Dissemination of Biological Occurrences of Chemical Structures Through Wikidata
bioRxiv preprint doi: https://doi.org/10.1101/2021.02.28.433265; this version posted March 1, 2021. The copyright holder has placed this preprint (which was not certified by peer review) in the Public Domain. It is no longer restricted by copyright. Anyone can legally share, reuse, remix, or adapt this material for any purpose without crediting the original authors. Open Natural Products Research: Curation and Dissemination of Biological Occurrences of Chemical Structures through Wikidata Adriano Rutz1,2, Maria Sorokina3, Jakub Galgonek4, Daniel Mietchen5, Egon Willighagen6, James Graham7, Ralf Stephan8, Roderic Page9, Jiˇr´ıVondr´aˇsek4, Christoph Steinbeck3, Guido F. Pauli7, Jean-Luc Wolfender1,2, Jonathan Bisson7, and Pierre-Marie Allard1,2 1School of Pharmaceutical Sciences, University of Geneva, CMU - Rue Michel-Servet 1, CH-1211 Geneva 4, Switzerland 2Institute of Pharmaceutical Sciences of Western Switzerland, University of Geneva, CMU - Rue Michel-Servet 1, CH-1211 Geneva 4, Switzerland 3Institute for Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Lessingstr. 8, 07732 Jena, Germany 4Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo n´amˇest´ı2, 166 10, Prague 6, Czech Republic 5School of Data Science, University of Virginia, Dell 1 Building, Charlottesville, Virginia 22904, United States 6Dept of Bioinformatics-BiGCaT, NUTRIM, Maastricht University, Universiteitssingel 50, NL-6229 ER, Maastricht, The Netherlands 7Center for Natural Product Technologies, Program for Collaborative Research -
(12) Patent Application Publication (10) Pub. No.: US 2016/0186168 A1 Konieczka Et Al
US 2016O1861 68A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0186168 A1 Konieczka et al. (43) Pub. Date: Jun. 30, 2016 (54) PROCESSES AND HOST CELLS FOR Related U.S. Application Data GENOME, PATHWAY. AND BIOMOLECULAR (60) Provisional application No. 61/938,933, filed on Feb. ENGINEERING 12, 2014, provisional application No. 61/935,265, - - - filed on Feb. 3, 2014, provisional application No. (71) Applicant: ENEVOLV, INC., Cambridge, MA (US) 61/883,131, filed on Sep. 26, 2013, provisional appli (72) Inventors: Jay H. Konieczka, Cambridge, MA cation No. 61/861,805, filed on Aug. 2, 2013. (US); James E. Spoonamore, Publication Classification Cambridge, MA (US); Ilan N. Wapinski, Cambridge, MA (US); (51) Int. Cl. Farren J. Isaacs, Cambridge, MA (US); CI2N 5/10 (2006.01) Gregory B. Foley, Cambridge, MA (US) CI2N 15/70 (2006.01) CI2N 5/8 (2006.01) (21) Appl. No.: 14/909, 184 (52) U.S. Cl. 1-1. CPC ............ CI2N 15/1082 (2013.01); C12N 15/81 (22) PCT Filed: Aug. 4, 2014 (2013.01); C12N 15/70 (2013.01) (86). PCT No.: PCT/US1.4/49649 (57) ABSTRACT S371 (c)(1), The present disclosure provides compositions and methods (2) Date: Feb. 1, 2016 for genomic engineering. Patent Application Publication Jun. 30, 2016 Sheet 1 of 4 US 2016/O186168 A1 Patent Application Publication Jun. 30, 2016 Sheet 2 of 4 US 2016/O186168 A1 &&&&3&&3&&**??*,º**)..,.: ××××××××××××××××××××-************************** Patent Application Publication Jun. 30, 2016 Sheet 3 of 4 US 2016/O186168 A1 No.vaegwzºkgwaewaeg Patent Application Publication Jun. 30, 2016 Sheet 4 of 4 US 2016/O186168 A1 US 2016/01 86168 A1 Jun. -
Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013
International Union of Pure and Applied Chemistry Division VIII Chemical Nomenclature and Structure Representation Division Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013. Prepared for publication by Henri A. Favre and Warren H. Powell, Royal Society of Chemistry, ISBN 978-0-85404-182-4 Appendix 3. STRUCTURES FOR ALKALOIDS, STEROIDS, TERPENOIDS, AND SIMILAR COMPOUNDS 1. Alkaloids H 13 12 16 17 H 14 1 H 2 10 9 11 15 HN20 8 3 5 4 H 7 H 6 19 H aconitane 16 17 H 5 9 6 21 19 18 8 N CH2-CH3 10 7 H 4 2 20 1 3 11 H 13 N H 14 15 12 CH3 22 ajmalan 17 CH3 16 6 5 H 21 9 4 H 8 N 10 7 2 20 19 1 3 CH 11 3 13 N H 14 15 18 12 akuammilan (named systematically by CAS) 24 17 H O 5 21 16 6 4 15 20 9 N 7 H3C 10 8 23 H CH2-CH3 14 19 18 1 2 3 11 13 N 12 CH3 22 alstophyllan (named systematically by CAS) 3 4 2 5 6 1 N 11b 6a CH3 H 12 11a 11 7 10 8 9 aporphine (named systematically by CAS) 8 7 9 N H 6 10 19 5 14 11 21 4 15 20 13 12 3 1 2 16 18 N 17 H aspidofractinine (named systematically by CAS) 8 7 9 6 N 10 19 CH2-CH3 5 20 21 14 11 H 4 15 13 12 2 3 1 16 18 N H 17 H aspidospermidine 17 12 CH 16 3 11 20 14 H 13 1 9 15 2 10 8 HN21 H 5 3 4 7 6 19 H CH3 18 atidane (named systematically by CAS) 17 24 12 16 CH2 23 O 11 20 14 13 22 1 9 H 2 15 10 8 OH N21 H 5 3 4 7 H 6 19 CH3 18 atisine (named systematically by CAS) 4 5 5’ 4’ 3 6 6’ 3’ 2 2 7’ ’ HN 1 7 1’ NH H 8 O 8’ H 10 14 15 ’ 11 13’ 15’ 9 9 O ’ 14 12 12’ 10’ 13 11’ berbaman (named systematically by CAS) 4 5 4a 3 6 7 2 13a N 13b 8 1 H 8a 13 9 12a 12 10 11 berbine (named systematically -
Saponins As Cytotoxic Agents: a Review
Phytochem Rev (2010) 9:425–474 DOI 10.1007/s11101-010-9183-z Saponins as cytotoxic agents: a review Irma Podolak • Agnieszka Galanty • Danuta Sobolewska Received: 13 January 2010 / Accepted: 29 April 2010 / Published online: 25 June 2010 Ó The Author(s) 2010. This article is published with open access at Springerlink.com Abstract Saponins are natural glycosides which Con A Concanavalin A possess a wide range of pharmacological properties ER Endoplasmic reticulum including cytotoxic activity. In this review, the recent ERK Extracellular signal-regulated studies (2005–2009) concerning the cytotoxic activity kinase of saponins have been summarized. The correlations GADD Growth arrest and DNA damage- between the structure and the cytotoxicity of both inducible gene steroid and triterpenoid saponins have been described GRP Glucose regulated protein as well as the most common mechanisms of action. hTERT Telomerase reverse transcriptase JAK Janus kinase Keywords Cytotoxic mechanisms Á MEK = MAPK Mitogen-activated protein kinase Glycosides Á Sar Á Steroid Á Triterpenoid MMP Matrix metalloproteinase mTOR Mammalian target of rapamycin Abbreviations NFjB Nuclear factor kappa-light-chain- AMPK AMP activated protein kinase enhancer of activated B cells BiP Binding protein NO Nitric oxide BrDU Bromodeoxyuridine PARP Poly ADP ribose polymerase CCAAT Cytidine-cytidine-adenosine- PCNA Proliferating cell nuclear antigen adenosine-thymidine PI3K Phosphoinositide-3-kinase CD Cluster of differentiation molecule PP Protein phosphatase CDK Cyclin-dependent kinase PPAR-c Peroxisome proliferator-activated CEBP CCAAT-enhancer-binding protein receptor c CHOP CEPB homology protein Raf Serine/threonine specific kinase STAT Signal transducer and activator of transcription TIMP Tissue inhibitor of metallo- proteinase TSC Tuberous sclerosis complex VEGF Vascular endothelial growth factor & I. -
Introduction (Pdf)
Dictionary of Natural Products on CD-ROM This introduction screen gives access to (a) a general introduction to the scope and content of DNP on CD-ROM, followed by (b) an extensive review of the different types of natural product and the way in which they are organised and categorised in DNP. You may access the section of your choice by clicking on the appropriate line below, or you may scroll through the text forwards or backwards from any point. Introduction to the DNP database page 3 Data presentation and organisation 3 Derivatives and variants 3 Chemical names and synonyms 4 CAS Registry Numbers 6 Diagrams 7 Stereochemical conventions 7 Molecular formula and molecular weight 8 Source 9 Importance/use 9 Type of Compound 9 Physical Data 9 Hazard and toxicity information 10 Bibliographic References 11 Journal abbreviations 12 Entry under review 12 Description of Natural Product Structures 13 Aliphatic natural products 15 Semiochemicals 15 Lipids 22 Polyketides 29 Carbohydrates 35 Oxygen heterocycles 44 Simple aromatic natural products 45 Benzofuranoids 48 Benzopyranoids 49 1 Flavonoids page 51 Tannins 60 Lignans 64 Polycyclic aromatic natural products 68 Terpenoids 72 Monoterpenoids 73 Sesquiterpenoids 77 Diterpenoids 101 Sesterterpenoids 118 Triterpenoids 121 Tetraterpenoids 131 Miscellaneous terpenoids 133 Meroterpenoids 133 Steroids 135 The sterols 140 Aminoacids and peptides 148 Aminoacids 148 Peptides 150 β-Lactams 151 Glycopeptides 153 Alkaloids 154 Alkaloids derived from ornithine 154 Alkaloids derived from lysine 156 Alkaloids