DOCSLIB.ORG

Biotransformation of Oleanane and Ursane Triterpenic Acids

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Biotransformation of Oleanane and Ursane Triterpenic Acids molecules Review Biotransformation of Oleanane and Ursane Triterpenic Acids Natalia A. Luchnikova 1,2 , Victoria V. Grishko 3 and Irina B. Ivshina 1,2,* 1 Institute of Ecology and Genetics of Microorganisms, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences, 614081 Perm, Russia; [email protected] 2 Department of Microbiology and Immunology, Perm State National Research University, 614990 Perm, Russia 3 Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences, 614013 Perm, Russia; [email protected] * Correspondence: [email protected]; Tel.: +7-342-2808114 Academic Editor: Derek J. McPhee Received: 9 October 2020; Accepted: 23 November 2020; Published: 25 November 2020 Abstract: Oleanane and ursane pentacyclic triterpenoids are secondary metabolites of plants found in various climatic zones and regions. This group of compounds is highly attractive due to their diverse biological properties and possible use as intermediates in the synthesis of new pharmacologically promising substances. By now, their antiviral, anti-inflammatory, antimicrobial, antitumor, and other activities have been confirmed. In the last decade, methods of microbial synthesis of these compounds and their further biotransformation using microorganisms are gaining much popularity. The present review provides clear evidence that industrial microbiology can be a promising way to obtain valuable pharmacologically active compounds in environmentally friendly conditions without processing huge amounts of plant biomass and using hazardous and expensive chemicals. This review summarizes data on distribution, microbial synthesis, and biological activities of native oleanane and ursane triterpenoids. Much emphasis is put on the processes of microbial transformation of selected oleanane and ursane pentacyclic triterpenoids and on the bioactivity assessment of the obtained derivatives. Keywords: biological activity; biotransformation; glycyrrhetinic acid; oleanolic acid; ursolic acid 1. Introduction Drugs derived from secondary plant metabolites make up about 25% of the global pharmaceutical market [1]. Secondary metabolites of plants are several groups of compounds; the most numerous (about 25,000 representatives) and diverse group is terpenic hydrocarbons and their oxygen-containing derivatives (terpenoids). Depending on the number of isoprene units (C5H8) in their structure, they contain a certain number of carbon atoms and are classified into mono-(C10), sesqui-(C15), di-(C20), triterpenoids (C30), etc. Naturally occurring triterpenoids are represented by more than 100 various types of skeletons [2]. Native triterpenoids, in particular, oleanane and ursane representatives, are of interest for researchers due to their availability and multiple biological activities, including antimicrobial, anti-inflammatory, antitumor, cytotoxic, hepatoprotective, and other activities [3–7]. Triterpenic molecules, however, are highly hydrophobic which significantly limits their use as effective pharmacological agents. At present, one of the most common ways to increase the effectiveness and bioavailability of triterpenoids is by chemical modification. This usually requires high temperature and pH, use of expensive reagents, and introduction of protective groups of molecule reactive centers [8–11]. An alternative way to obtain valuable derivatives is by biotransformation under normal and environmentally friendly conditions employing the catalytic activity of microorganisms with high regio- and stereoselectivity in one Molecules 2020, 25, 5526; doi:10.3390/molecules25235526 www.mdpi.com/journal/molecules Molecules 2020, 25, x FOR PEER REVIEW 2 of 34 Molecules 2020, 25, 5526 2 of 31 [8–11]. An alternative way to obtain valuable derivatives is by biotransformation under normal and environmentally friendly conditions employing the catalytic activity of microorganisms with high technologicalregio- and stereoselectivity stage. Furthermore, in one microbial technological conversion stage. Furthermore, ensures specific microbial modifications conversion of triterpenic ensures moleculespecific modifications sites that are ofeither triterpenic not modified molecule orsites poorly that are modified either not by modified synthetic or transformations poorly modified [12 by]. Notesynthetic that, transformations among the known [12]. microbialNote that, biocatalysts,among the known members microbial of mycelial biocatalysts, fungi are members the most of studiedmycelial[ 13fungi–15] arewhereas the most bacterial studied catalysts [13–15] are whereas only represented bacterial catalysts by a few are gram-positive only represented species by [16 a– few20]. Thegram-positive first papers species on microbial [16–20]. The transformation first papers ofon triterpenoids microbial transformation were published of triterpenoids in the 1960s were [21]. Thepublished earliest in informationthe 1960s [21]. related The earliest to bioconversion information processes related to of bioconversion oleanane derivatives processes catalyzed of oleanane by fungi,derivatives such catalyzed as Curvularia by fungi, lunata suchATCC as 13432,CurvulariaTrichotecium lunata ATCC roseum 13432,ATCC Trichotecium 8685, Cunninghamella roseum ATCCsp. ATCC8685, Cunninghamella 3229, Mucor griseo-cyanus sp. ATCC 3229,ATCC Mucor 1207-a, griseo-cyanusHelicostylum ATCC piriforme 1207-a, HelicostylumATCC 8992, piriformeFusarium ATCC lini, and8992,Cunninghamella Fusarium lini, and blakesleana Cunninghamelladates back blakesleana to about dates the sameback to time about [22– the25]. same The time data [22–25]. on bacterial The transformationdata on bacterial of oleananetransformation triterpenoids of oleanane by Streptomyces triterpenoidssp. G-20by Streptomyces and Chainia sp. antibiotica G-20 andIFO Chainia 12,246 wereantibiotica reported IFO in12,246 the second were reported half of the in1980s the second [26,27]. half As forof microbialthe 1980s transformations[26,27]. As for ofmicrobial ursane pentacyclictransformations triterpenoids of ursane bypentacyclic both fungal triterpenoids (Mucor plumbeus by both ATCCfungal 4740(Mucor [28 plumbeus]) and bacterial ATCC 4740 (Nocardia [28]) sp.and NRRLbacterial 5646 (Nocardia [29]) strains, sp. NRRL those 5646 studies [29]) were strains, initiated those only studies in the were 2000s. initiated Henceforth, only in the the interest 2000s. inHenceforth, the topic discussedthe interest has in beenthe topic increasing discussed and thehas Activebeen increasing Triterpenoid and Biocatalysts the Active ListTriterpenoid has been expandedBiocatalysts every List has year, been as isexpanded the number every of year, various as is bioactive the number triterpenic of various derivatives bioactive formed triterpenic via biotransformationsderivatives formed [via30– biot32].ransformations [30–32]. Now, preparationpreparation of biologicallybiologically active compounds based on pentacyclic triterpenoids is an actual research discussed in plenty of experimental and review publications [8,12,32–34]. [8,12,32–34]. However, However, the reviews are are overwhelmingly overwhelmingly focused focused on on chemical chemical transformations transformations or or describe describe specific specific types types of ofbiological biological activities activities of triterpenoids. of triterpenoids. Less Less frequently, frequently, they they deal dealwith with biological biological transformations. transformations. The Thelatest latest of the of thefew few reviews reviews on onmicrobial microbial transformati transformationsons of of pentacyclic pentacyclic triterpenoids triterpenoids include include literature data upup to to 2016 2016 [12 ,[12,32,33,35].32,33,35]. Our Our review review summarizes summarizes the data the from data 2013 from to the 2013 present to the on distribution,present on microbialdistribution, biosynthesis, microbial biosynthesis, biological activity, biological and ac mainlytivity, biotransformationand mainly biotransformation of oleanane of and oleanane ursane pentacyclicand ursane triterpenoidspentacyclic totriterpenoids obtain promising to obtain biologically promising active biologically compounds active or intermediatescompounds or of theirintermediates synthesis. of their synthesis. 2. Distribution in Nature Plant pentacyclic triterpenoids are represented by more than two dozen structural types; the most common are oleanane and ursane ones (Figure1 1).). InIn freefree forms,forms, triterpenoidstriterpenoids areare nonvolatilenonvolatile lipophilic substances that are soluble in organic solventssolvents andand insolubleinsoluble inin water.water. The mostmost availableavailable oleanane triterpenoids are oleanolic acid 1 (OA, 3β-hydroxy-olean-12-en-28-oic acid, C H O , CAS oleanane triterpenoids are oleanolic acid 1 (OA, 3β-hydroxy-olean-12-en-28-oic acid, C3030H4848O33, CAS 508-02-1) and glycyrrhetinic acid 2 (GA, 3β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid, C H O , 508-02-1) and glycyrrhetinic acid 2 (GA, 3β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid, C3030H4646O4, CAS 471-53-4), and ursolic acid 3 (UA, 3β-hydroxy-urs-12-en-28-oic acid, C H O , CAS 77-52-1) is CAS 471-53-4), and ursolic acid 3 (UA, 3β-hydroxy-urs-12-en-28-oic acid, C3030H4848O3, CAS 77-52-1) is the most available ursane triterpenoid. Biosynthesis of oleanane and ursane pentacyclic triterpenoids in plants occurs occurs by by conversion conversion of of the the acyclic acyclic triterpene triterpene squalene squalene (4) ( 4to) to2,3-oxidosqualene
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.
    [Show full text]
  • <I>Anemone Raddeana</I>
    REVIEW Pharmacochemistry & Biomacromolecule Research Laboratories1, Qiqihar Medical University, Qiqihar; College of Pharmacy2, Changchun University of Chinese Medicine, Changchun, P. R.China Phytochemicals and bioactivities of Anemone raddeana Regel: a review Yong-Xu Sun 1,∗, Ji-Cheng Liu 1,∗, Da-You Liu 2,∗ Received April 28, 2011, accepted May 27, 2011 Ji-Cheng Liu, Qiqihar Medical University, 333 BuKui Street, JianHua District, Qiqihar, 161006, China [email protected] Da-YouLiu, College of Pharmacy, Changchun University of Chinese Medicine, 1035 BoShuo Road, Jing Yue Economic Development District, Changchun, 130117, China [email protected] Yong-Xu Sun, Pharmacochemistry & Biomacromolecule Research Laboratories, Qiqihar Medical University, 333 BuKui Street, JianHua District, Qiqihar, 161006, China [email protected] ∗These authors contributed equally to this work. Pharmazie 66: 813–821 (2011) doi: 10.1691/ph.2011.1574 Anemone raddeana, usually called as “ToujianLiang” in China, is an Anemone herb belonging to the Ranun- culaceae family. Until now there are in total 67 of chemical components identified including triterpenoids, steroids, lactones, fats and oils, saccharide and alkaloids. A broad spectrum of pharmacological activity of A. raddeana compounds have been reported, such as antitumor, antimicrobial, anti-inflammatory, sedative and analgesic activites, as well as anti-convulsant and anti-histamine effects. In view of this, we initiated this short review to present the phytochemical and pharmacological profile of A. raddeana to support future studies in this discipline. 1. Introduction Anemone raddeana Regel is a traditional Chinese medicinal herb belonging to the Anemone genus (Ranunculaceae), which is widely distributed in Russia (Far east), northeast of China, Japan and Korea (Chen et al.
    [Show full text]
  • 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].
    [Show full text]
  • 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
    [Show full text]
  • 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.
    [Show full text]
  • Colletotrichum: a Catalogue of Confusion
    Online advance Fungal Diversity Colletotrichum: a catalogue of confusion Hyde, K.D.1,2*, Cai, L.3, McKenzie, E.H.C.4, Yang, Y.L.5,6, Zhang, J.Z.7 and Prihastuti, H.2,8 1International Fungal Research & Development Centre, The Research Institute of Resource Insects, Chinese Academy of Forestry, Bailongsi, Kunming 650224, PR China 2School of Science, Mae Fah Luang University, Thasud, Chiang Rai 57100, Thailand 3Novozymes China, No. 14, Xinxi Road, Shangdi, HaiDian, Beijing, 100085, PR China 4Landcare Research, Private Bag 92170, Auckland, New Zealand 5Guizhou Academy of Agricultural Sciences, Guiyang, Guizhou 550006 PR China 6Department of Biology and Geography, Liupanshui Normal College. Shuicheng, Guizhou 553006, P.R. China 7Institute of Biotechnology, College of Agriculture & Biotechnology, Zhejiang University, Kaixuan Rd 258, Hangzhou 310029, PR China 8Department of Biotechnology, Faculty of Agriculture, Brawijaya University, Malang 65145, Indonesia Hyde, K.D., Cai, L., McKenzie, E.H.C., Yang, Y.L., Zhang, J.Z. and Prihastuti, H. (2009). Colletotrichum: a catalogue of confusion. Fungal Diversity 39: 1-17. Identification of Colletotrichum species has long been difficult due to limited morphological characters. Single gene phylogenetic analyses have also not proved to be very successful in delineating species. This may be partly due to the high level of erroneous names in GenBank. In this paper we review the problems associated with taxonomy of Colletotrichum and difficulties in identifying taxa to species. We advocate epitypification and use of multi-locus phylogeny to delimit species and gain a better understanding of the genus. We review the lifestyles of Colletotrichum species, which may occur as epiphytes, endophytes, saprobes and pathogens.
    [Show full text]
  • Notes on Currently Accepted Species of Colletotrichum
    Mycosphere 7(8) 1192-1260(2016) www.mycosphere.org ISSN 2077 7019 Article Doi 10.5943/mycosphere/si/2c/9 Copyright © Guizhou Academy of Agricultural Sciences Notes on currently accepted species of Colletotrichum Jayawardena RS1,2, Hyde KD2,3, Damm U4, Cai L5, Liu M1, Li XH1, Zhang W1, Zhao WS6 and Yan JY1,* 1 Institute of Plant and Environment Protection, Beijing Academy of Agriculture and Forestry Sciences, Beijing 100097, People’s Republic of China 2 Center of Excellence in Fungal Research, Mae Fah Luang University, Chiang Rai 57100, Thailand 3 Key Laboratory for Plant Biodiversity and Biogeography of East Asia (KLPB), Kunming Institute of Botany, Chinese Academy of Science, Kunming 650201, Yunnan, China 4 Senckenberg Museum of Natural History Görlitz, PF 300 154, 02806 Görlitz, Germany 5State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China 6Department of Plant Pathology, College of Plant Protection, China Agricultural University, Beijing 100193, China. Jayawardena RS, Hyde KD, Damm U, Cai L, Liu M, Li XH, Zhang W, Zhao WS, Yan JY 2016 – Notes on currently accepted species of Colletotrichum. Mycosphere 7(8) 1192–1260, Doi 10.5943/mycosphere/si/2c/9 Abstract Colletotrichum is an economically important plant pathogenic genus worldwide, but can also have endophytic or saprobic lifestyles. The genus has undergone numerous revisions in the past decades with the addition, typification and synonymy of many species. In this study, we provide an account of the 190 currently accepted species, one doubtful species and one excluded species that have molecular data. Species are listed alphabetically and annotated with their habit, host and geographic distribution, phylogenetic position, their sexual morphs and uses (if there are any known).
    [Show full text]
  • Quantification, Chemical and Biological Characterization of the Saponosides Material from Sida Cordifolia L
    Revista Cubana de Plantas Medicinales. 2013;18(2):298-314 ARTÍCULO ORIGINAL Quantification, chemical and biological characterization of the saponosides material from Sida cordifolia L. (escobilla) Cuantificación, caracterización química y biológica del contenido saponósido de Sida cordifolia L. (escobilla) Biol. Oscar Julián Velásquez Ballesteros, MSc. Elizabeth Murillo Perea, Dr. John Jairo Méndez, Dr. Walter Murillo Arango, Biol. Diana Alexandra Noreña Universidad del Tolima. Colombia. ABSTRACT Introduction: Sida cordifolia L. (Malvaceae) is a weed about which not much is known in Colombia. This plant is used in folk medicine to treat oral mucosa, blennorrhea, asthma and bronchitis. In Brazil it finds application as an anti-inflammatory, while in Colombia its "baba" is used for treating hair loss, constipation and internal fever, among other ailments. Objectives: to quantify the saponoside content and evaluate its antioxidant and antifungal functionality. Methods: we prepared organic, aqueous and hydroalcoholic extracts from the aerial section of the plant. The saponoside material was quantified by the DNS and p-anisaldehyde methods. The most concentrated extracts were selected for antioxidant and antifungal assays. Results: it was found that Sida cordifolia, collected in Ibague-Colombia, is a good source of saponins with diverse chemical structures, mainly of steroidal nature, some of which may be hecogenin, diosgenin or a homologue. Conclusions: these factors may contribute, at least in part, to the antioxidant and antifungal functionality of Sida cordifolia L., but this capacity may be modified if these saponins act independently or together with some other metabolites of the plant such as tannins, flavonoids steroids, and alkaloids among others. Key words: Sida cordifolia, saponins, weed, antioxidant, p-anisaldhyde.
    [Show full text]
  • Colletotrichum: Biological Control, Bio- Catalyst, Secondary Metabolites and Toxins
    Mycosphere 7(8) 1164-1176(2016) www.mycosphere.org ISSN 2077 7019 Article Doi 10.5943/mycosphere/si/2c/7 Copyright © Guizhou Academy of Agricultural Sciences Mycosphere Essay 16: Colletotrichum: Biological control, bio- catalyst, secondary metabolites and toxins Jayawardena RS1,2, Li XH1, Liu M1, Zhang W1 and Yan JY1* 1 Institute of Plant and Environment Protection, Beijing Academy of Agriculture and Forestry Sciences, Beijing 100097, People’s Republic of China 2 Center of Excellence in Fungal Research and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand Jayawardena RS, Li XH, Liu M, Zhang W, Yan JY 2016 – Mycosphere Essay 16: Colletotrichum: Biological control, bio-catalyst, secondary metabolites and toxins. Mycosphere 7(8) 1164–1176, Doi 10.5943/mycosphere/si/2c/7 Abstract The genus Colletotrichum has received considerable attention in the past decade because of its role as an important plant pathogen. The importance of Colletotrichum with regard to industrial application has however, received little attention from scientists over many years. The aim of the present paper is to explore the importance of Colletotrichum species as bio-control agents and as a bio-catalyst as well as secondary metabolites and toxin producers. Often the names assigned to the above four industrial applications have lacked an accurate taxonomic basis and this needs consideration. The current paper provides detailed background of the above topics. Key words – biotransformation – colletotrichin – mycoherbicide – mycoparasites – pathogenisis – phytopathogen Introduction Colletotrichum was introduced by Corda (1831), and is a coelomycete belonging to the family Glomerellaceae (Maharachchikumbura et al. 2015, 2016). Species of this genus are widely known as pathogens of economical crops worldwide (Cannon et al.
    [Show full text]
  • Linu Ģenētisko Resursu Rezistence Pret Slimībām - Rezistences Izvērtējums Un Uzlabošanas Metodes
    DAUGAVPILS UNIVERSITĀTE DZĪVĪBAS ZINĀTĽU UN TEHNOLOĢIJU INSTITŪTS Linu ģenētisko resursu rezistence pret slimībām - rezistences izvērtējums un uzlabošanas metodes Promocijas darbs Zinātniskā doktora grāda, zinātnes doktora (Ph.D.) bioloģijā iegūšanai (ekoloģijas apakšnozarē) Promocijas darba autore: Inga Morozova Promocijas darba zinātniskā vadītāja: Asoc. profesore, Dr. biol. Dace Grauda Daugavpils 2020 Promocijas darbs izstrādāts: APP „Agroresursu ekonomikas institūta‖, Laukaugu selekcijas un agroekoloģijas nodaļas, Viļānu daļas izmēģinājumu demonstrējuma laukos un Latvijas Universitātes, Bioloģijas institūta, Vides ģenētikas laboratorijā laika periodā no 2014.- 2019. gadam. Darba raksturs: zinātniskā doktora grāda, zinātnes doktora (Ph.D.) bioloģijā iegūšanai ekoloģijas apakšnozarē Promocijas darba zinātniskais vadītājs: Dr. biol., asoc. prof., Dace Grauda (Latvijas Universitāte, Latvija) Recenzenti: Dr.biol., prof., Inese Kokina (Daugavpils Universitāte, Latvija) Ph.D.,vad.pētnieks, Petras Prakas (Lietuvas Valsts zinātniski pētnieciskā institūta Dabas izpētes centrs, Lietuva) Ph.D., pētnieks, Donatas Šneideris (Lietuvas Valsts zinātniski pētnieciskā institūta Dabas izpētes centrs, Lietuva) Promocijas padomes priekšsēdētājs: Dr. biol., prof. Arvīds Barševskis Promocijas darba aizstāvēšana notiks: Daugavpils Universitātes (DU) Bioloģijas zinātľu nozares promocijas padomes atklātā sēdē tiešsaistē ZOOM platformā, 2020. gada 19. novembrī plkst. 11.00. Ar promocijas darbu un tā kopsavilkumu var iepazīties Daugavpils Universitātes bibliotēkā,
    [Show full text]
  • Nomenclature of Steroids
    Pure&App/. Chern.,Vol. 61, No. 10, pp. 1783-1822,1989. Printed in Great Britain. @ 1989 IUPAC INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY and INTERNATIONAL UNION OF BIOCHEMISTRY JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE* NOMENCLATURE OF STEROIDS (Recommendations 1989) Prepared for publication by G. P. MOSS Queen Mary College, Mile End Road, London El 4NS, UK *Membership of the Commission (JCBN) during 1987-89 is as follows: Chairman: J. F. G. Vliegenthart (Netherlands); Secretary: A. Cornish-Bowden (UK); Members: J. R. Bull (RSA); M. A. Chester (Sweden); C. LiCbecq (Belgium, representing the IUB Committee of Editors of Biochemical Journals); J. Reedijk (Netherlands); P. Venetianer (Hungary); Associate Members: G. P. Moss (UK); J. C. Rigg (Netherlands). Additional contributors to the formulation of these recommendations: Nomenclature Committee of ZUB(NC-ZUB) (those additional to JCBN): H. Bielka (GDR); C. R. Cantor (USA); H. B. F. Dixon (UK); P. Karlson (FRG); K. L. Loening (USA); W. Saenger (FRG); N. Sharon (Israel); E. J. van Lenten (USA); S. F. Velick (USA); E. C. Webb (Australia). Membership of Expert Panel: P. Karlson (FRG, Convener); J. R. Bull (RSA); K. Engel (FRG); J. Fried (USA); H. W. Kircher (USA); K. L. Loening (USA); G. P. Moss (UK); G. Popjiik (USA); M. R. Uskokovic (USA). Correspondence on these recommendations should be addressed to Dr. G. P. Moss at the above address or to any member of the Commission. Republication of this report is permitted without the need for formal IUPAC permission on condition that an acknowledgement, with full reference together with IUPAC copyright symbol (01989 IUPAC), is printed.
    [Show full text]
  • Bright” Future?
    UNIVERSITÀ DEGLI STUDI DEL PIEMONTE ORIENTALE “AMEDEO AVOGADRO” DIPARTIMENTO DI SCIENZE DEL FARMACO Dottorato di Ricerca in Chemistry and Biology XXXI cycle PENTACYCLIC TRITERPENIC ACIDS AS MODULATORS OF TRANSCRIPTION FACTORS: OLD SCAFFOLDS WITH A “BRIGHT” FUTURE? Federica Rogati Supervised by Prof. Alberto Minassi Ph.D program co-ordinator Prof. Guido Lingua UNIVERSITÀ DEGLI STUDI DEL PIEMONTE ORIENTALE “AMEDEO AVOGADRO” DIPARTIMENTO DI SCIENZE DEL FARMACO Dottorato di Ricerca in Chemistry and Biology XXXI cycle PENTACYCLIC TRITERPENIC ACIDS AS MODULATORS OF TRANSCRIPTION FACTORS: OLD SCAFFOLDS WITH A “BRIGHT” FUTURE? Federica Rogati Supervised by Prof. Alberto Minassi Ph.D program co-ordinator Prof. Guido Lingua ai miei Nonni, ai miei angeli “una nave è al sicuro nel porto, ma questo non è il posto per cui le navi sono fatte” William G.T Shedd ~ CONTENTS ~ Preface 1 CHAPTER 1: DEOXYGENATION OF URSOLIC, OLEANOLIC AND 9 BETULINIC ACID TO THEIR CORRESPONDING C-28 METHYL DERIVATIVES (α-AMYRIN, β-AMYRIN, LUPEOL) 1.1 Introduction 10 1.2 Rationale of the project 13 1.3 Results and discussion 15 1.3.1 Chemistry 15 1.3.2 Biological evaluation 19 1.3.3 Conclusions 19 1.4 Experimental section 20 1.5 Bibliography 25 CHAPTER 2: TRITERPENOID HYDROXAMATES AS HIF PROLYL 27 HYDROLASE INHIBITORS 2.1 Introduction 28 2.2 Rationale of the project 32 2.3 Results and discussion 33 2.3.1 Chemistry 33 2.3.2 Biological evaluation 46 2.3.3 Conclusions 61 2.4 Experimental section 62 i 2.5 Bibliography 76 CHAPTER 3: STRIGOTERPENOIDS, A CLASS OF CROSS-KINGDOM 81 STRESS RESPONSE MODULATORS 3.1 Introduction 82 3.2 Rationale of the project 90 3.3 Results and discussion 94 3.3.1 Chemistry 94 3.3.2 Biological evaluation 101 3.3.3 Conclusions 104 3.4 Experimental section 105 3.5 Bibliography 118 CHAPTER 4: SYNTHESIS OF 1,2,3- TRIAZOLE ANALOGUES OF 121 ANTI-HIV DRUG BEVIRIMAT 4.1 Introduction 122 4.2 Rationale of the project 131 4.3 Results and discussion 132 4.3.1 Chemistry 132 4.3.2 Conclusions 139 4.4 Experimental section 140 4.5 Bibliography 151 5.
    [Show full text]