Isolation and Identification of Cyclic Polyketides From

Total Page:16

File Type:pdf, Size:1020Kb

Isolation and Identification of Cyclic Polyketides From ISOLATION AND IDENTIFICATION OF CYCLIC POLYKETIDES FROM ENDIANDRA KINGIANA GAMBLE (LAURACEAE), AS BCL-XL/BAK AND MCL-1/BID DUAL INHIBITORS, AND APPROACHES TOWARD THE SYNTHESIS OF KINGIANINS Mohamad Nurul Azmi Mohamad Taib, Yvan Six, Marc Litaudon, Khalijah Awang To cite this version: Mohamad Nurul Azmi Mohamad Taib, Yvan Six, Marc Litaudon, Khalijah Awang. ISOLATION AND IDENTIFICATION OF CYCLIC POLYKETIDES FROM ENDIANDRA KINGIANA GAMBLE (LAURACEAE), AS BCL-XL/BAK AND MCL-1/BID DUAL INHIBITORS, AND APPROACHES TOWARD THE SYNTHESIS OF KINGIANINS . Chemical Sciences. Ecole Doctorale Polytechnique; Laboratoires de Synthase Organique (LSO), 2015. English. tel-01260359 HAL Id: tel-01260359 https://pastel.archives-ouvertes.fr/tel-01260359 Submitted on 22 Jan 2016 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. ISOLATION AND IDENTIFICATION OF CYCLIC POLYKETIDES FROM ENDIANDRA KINGIANA GAMBLE (LAURACEAE), AS BCL-XL/BAK AND MCL-1/BID DUAL INHIBITORS, AND APPROACHES TOWARD THE SYNTHESIS OF KINGIANINS MOHAMAD NURUL AZMI BIN MOHAMAD TAIB FACULTY OF SCIENCE UNIVERSITY OF MALAYA KUALA LUMPUR, MALAYSIA AND ECOLE POLYTECHNIQUE PALAISEAU, FRANCE 2015 ISOLATION AND IDENTIFICATION OF CYCLIC POLYKETIDES FROM ENDIANDRA KINGIANA GAMBLE (LAURACEAE), AS BCL-XL/BAK AND MCL-1/BID DUAL INHIBITORS, AND APPROACHES TOWARD THE SYNTHESIS OF KINGIANINS MOHAMAD NURUL AZMI BIN MOHAMAD TAIB THESIS SUBMITTED IN FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY FACULTY OF SCIENCE UNIVERSITY OF MALAYA KUALA LUMPUR, MALAYSIA AND ECOLE POLYTECHNIQUE PALAISEAU, FRANCE 2015 Thesis submitted for the award of the degree of DOCTOR OF PHILOSOPHY In the field of CHEMISTRY by Mohamad Nurul Azmi MOHAMAD TAIB ISOLATION AND IDENTIFICATION OF CYCLIC POLYKETIDES FROM ENDIANDRA KINGIANA GAMBLE (LAURACEAE), AS BCL-XL/BAK AND MCL-1/BID DUAL INHIBITORS, AND APPROACHES TOWARD THE SYNTHESIS OF KINGIANINS Presented on 12th November 2015, to a committee composed of : Prof. Dr. Hasnah Mohd Sirat Referee Prof. Dr. Benoit Crousse Referee Prof. Dr. Sylvie Michel Referee Assoc. Prof. Dr. Rozana Othman Referee Prof. Dr. Khalijah Awang Examiner Dr. Yvan Six Examiner Dr. Marc Litaudon Examiner Dr. Fabien Gagosz President UNIVERSITY OF MALAYA ORIGINAL LITERARY WORK DECLARATION Name of Candidate: Mohamad Nurul Azmi MOHAMAD TAIB (I.C/Passport No: 851207-03-6031 ) Registration/Matric No: SHC110066 Name of Degree: Doctor of philosophy (PhD.) Title of Project Paper/Research Report/Dissertation/Thesis (“this Work”): Isolation and identification of cyclic polyketides from Endiandra kingiana Gamble (Lauraceae), as Bcl-xL/Bak and Mcl-1/Bid dual inhibitors, and approaches toward the synthesis of kingianins. Field of Study: Chemistry I do solemnly and sincerely declare that: (1) I am the sole author/writer of this Work; (2) This Work is original; (3) Any use of any work in which copyright exists was done by way of fair dealing and for permitted purposes and any excerpt or extract from, or reference to or reproduction of any copyright work has been disclosed expressly and sufficiently and the title of the Work and its authorship have been acknowledged in this Work; (4) I do not have any actual knowledge nor do I ought reasonably to know that the making of this work constitutes an infringement of any copyright work; (5) I hereby assign all and every rights in the copyright to this Work to the University of Malaya (“UM”), who henceforth shall be owner of the copyright in this Work and that any reproduction or use in any form or by any means whatsoever is prohibited without the written consent of UM having been first had and obtained; (6) I am fully aware that if in the course of making this Work I have infringed any copyright whether intentionally or otherwise, I may be subject to legal action or any other action as may be determined by UM. Candidate’s Signature Date: Subscribed and solemnly declared before, Witness’s Signature Date: Name: Dr. Khalijah Awang Designation: Professor iii ABSTRACT The preliminary screening showed that the bark of Endiandra kingiana Gamble exhibited potency as a modulating agent between Bcl-xL and Bak, which prompted its chemical investigation. Two groups of compounds were isolated and characterized; the endiandric acid series and the kingianin series. Eight new endiandric acid analogues (kingianic acids A-H [ 120 -127 ]) and three new kingianin analogues (kingianin O-Q [128 -130 ]) were isolated and structurally elucidated. The isolated compounds were evaluated for two bioassays; Bcl-xL/Bak and Mcl-1/Bid of binding affinities and cytotoxic effects against various human tumour cells. The second part describes the progression towards the total synthesis of kingianin analogues. The pentacyclic kingianin skeleton was formed by Diels-Alder reaction between two monomers having a bicyclo[4.2.0]octadiene backbone formed by a stereospecific electrocyclization of polyenes. The research was focusing on construction of bicyclo[4.2.0]octadiene monomer using [2+2] ketene cycloaddition approach at the early stage of the synthesis. One of the main advantages of such a strategy is the rapid assembly of the carbon skeleton of kingianins, thus maximizing the chances for good overall yields of the final products. So far, an efficient synthesis of the bicyclo[4.2.0]octene backbone was successfully achieved. Five approaches to synthesize this backbone starting from [2+2] cycloaddition of the cyclohexadienes to functionalized ketenes followed by functionalization of substituent at C-7 and C-8 positions with the correct relative configuration were described. From these approaches, compounds 280 and 311 were identified as the key intermediates. This key step of the synthesis provided an access to the kingianins skeleton. iv ABSTRAK Pemeriksaan awal menunjukkan bahawa kulit pokok Endiandra kingiana Gamble mempunyai potensi sebagai ejen modulasi antara protein Bcl-xL dan Bak, yang mendorong kepada penyiasatan sebatian kimianya. Dua kumpulan sebatian telah diasingkan dan dikenalpasti iaitu; siri asid endiandrik dan siri kingianin. Lapan analog asid endiandrik baharu (asid kingianik A-H [ 120 -127 ]) dan tiga analog kingianin baharu (kingianin O-Q [128 -130 ]) telah diasingkan dan dikenalpasti. Sebatian tulen yang diasingkan telah dinilai terhadap dua bioassei; kebolehan untuk mengikat antara protein Bcl-xL/Bak dan Mcl-1/Bid dan kesan sitotoksik terhadap sel tumor manusia. Bahagian kedua menerangkan perkembangan sintesis analog kingianin. Rangka pentasiklik kingianin adalah terbentuk daripada tindak balas Diels-Alder antara dua monomer yang mempunyai struktur bisiklo[4.2.0]oktadiena yang dibentuk daripada elektrosiklik poliena. Kajian ini memberi tumpuan kepada pembinaan bisiklo[4.2.0]oktadiena monomer dengan menggunakan pendekatan sikloadisi [2+2] ketena pada peringkat awal sintesis. Salah satu kelebihan utama strategi ini adalah pembentukan pantas rangka karbon kingianin, sekaligus meningkatkan peluang pembentukan hasil yang maksimum. Setakat ini, sintesis bisiklo[4.2.0]oktana telah berjaya dicapai. Sebanyak lima pendekatan telah dilakukan bermula dari sikloadisi [2+2] antara sikloheksadiena dengan ketena diikuti dengan fungsionalisasi kumpulan berfungsi dikedudukan C-7 dan C-8 dengan konfigurasi yang betul. Daripada pendekatan ini, sebatian 280 dan 311 telah dikenalpasti sebagai sebatian perantara yang terbaik bagi menghasilkan analog kingianin. v RÉSUMÉ Un criblage biologique préliminaire a montré que l'extrait des écorces d'Endiandrakingiana possédait une forte affinité pour la protéine anti-apoptotique Bcl- xL, motivant ainsi la réalisationd’une étude chimique complète. Deux groupes de composés ont été isolés et caractérisés: d’une part, huit nouveaux dérivés de l'acide endiandrique (les acides kingianiques A à H [ 120 −127 ]) et d’autre part, trois nouvelleskingianines (les kingianines O à Q [ 128 −130 ]). Le potentiel inhibiteur des nouvelles molécules vis-à-vis des interactionsBcl-xL/Bak et Mcl-1/Bida ensuite été évalué, ainsi que leurs propriétés cytotoxiques sur diverses lignées cellulaires tumorales humaines. La seconde partie du manuscrit présente une approche vers la synthèse totale des kingianines et de composés analogues.Le squelette pentacyclique des produits naturels résulte formellement d’une réaction de Diels-Alder entre deux unités bicyclo[4.2.0]octadiène, elles-mêmes issues d’une cascade d’électrocyclisation de tétraènes entièrement conjugués. Une stratégie de construction directe de motifs bicyclo[4.2.0]octadiènespar une cycloaddition [2+2] entre des cycloalcènes et des cétènes convenablement choisisdoit assurer l’obtention des molécules cibles avec de bons rendements globaux. Au total, cinq approches ont été implémentées. Elles débutent par la cycloaddition [2+2] entre des cyclohexadiènes et des cétènes fonctionnalisés et se poursuivent par la fonctionnalisation des positions C7 et C8 en contrôlant la configuration relative de ces centres. Les résultats obtenus ont conduit à identifier les composés 280 et 311 comme des intermédiaires clefs à même d’être convertis en diènes
Recommended publications
  • Enediynes, Enyneallenes, Their Reactions, and Beyond
    Advanced Review Enediynes, enyne-allenes, their reactions, and beyond Elfi Kraka∗ and Dieter Cremer Enediynes undergo a Bergman cyclization reaction to form the labile 1,4-didehy- drobenzene (p-benzyne) biradical. The energetics of this reaction and the related Schreiner–Pascal reaction as well as that of the Myers–Saito and Schmittel reac- tions of enyne-allenes are discussed on the basis of a variety of quantum chemical and available experimental results. The computational investigation of enediynes has been beneficial for both experimentalists and theoreticians because it has led to new synthetic challenges and new computational methodologies. The accurate description of biradicals has been one of the results of this mutual fertilization. Other results have been the computer-assisted drug design of new antitumor antibiotics based on the biological activity of natural enediynes, the investigation of hetero- and metallo-enediynes, the use of enediynes in chemical synthesis and C materials science, or an understanding of catalyzed enediyne reactions. " 2013 John Wiley & Sons, Ltd. How to cite this article: WIREs Comput Mol Sci 2013. doi: 10.1002/wcms.1174 INTRODUCTION symmetry-allowed pericyclic reactions, (ii) aromatic- ity as a driving force for chemical reactions, and (iii) review on the enediynes is necessarily an ac- the investigation of labile intermediates with biradical count of intense and successful interdisciplinary A character. The henceforth called Bergman cyclization interactions of very different fields in chemistry provided deeper insight into the electronic structure involving among others organic chemistry, matrix of biradical intermediates, the mechanism of organic isolation spectroscopy, quantum chemistry, biochem- reactions, and orbital symmetry rules.
    [Show full text]
  • Bruxner Park Flora Reserve Working Plan
    Bruxner Park Flora Reserve Working Plan Working Plan for Bruxner Park Flora Reserve No 3 Upper North East Forest Agreement Region North East Region Contents Page 1. DETAILS OF THE RESERVE 2 1.1 Introduction 2 1.2 Location 2 1.3 Key Attributes of the Reserve 2 1.4 General Description 2 1.5 History 6 1.6 Current Usage 8 2. SYSTEM OF MANAGEMENT 9 2.1 Objectives of Management 9 2.2 Management Strategies 9 2.3 Management Responsibility 11 2.4 Monitoring, Reporting and Review 11 3. LIST OF APPENDICES 11 Appendix 1 Map 1 Locality Appendix 1 Map 2 Cadastral Boundaries, Forest Types and Streams Appendix 1 Map 3 Vegetation Growth Stages Appendix 1 Map 4 Existing Occupation Permits and Recreation Facilities Appendix 2 Flora Species known to occur in the Reserve Appendix 3 Fauna records within the Reserve Y:\Tourism and Partnerships\Recreation Areas\Orara East SF\Bruxner Flora Reserve\FlRWP_Bruxner.docx 1 Bruxner Park Flora Reserve Working Plan 1. Details of the Reserve 1.1 Introduction This plan has been prepared as a supplementary plan under the Nature Conservation Strategy of the Upper North East Ecologically Sustainable Forest Management (ESFM) Plan. It is prepared in accordance with the terms of section 25A (5) of the Forestry Act 1916 with the objective to provide for the future management of that part of Orara East State Forest No 536 set aside as Bruxner Park Flora Reserve No 3. The plan was approved by the Minister for Forests on 16.5.2011 and will be reviewed in 2021.
    [Show full text]
  • Protein Phosphatases 1 and 2A and Their Naturally Occurring Inhibitors: Current Topics in Smooth Muscle Physiology and Chemical Biology
    J Physiol Sci (2018) 68:1–17 https://doi.org/10.1007/s12576-017-0556-6 REVIEW Protein phosphatases 1 and 2A and their naturally occurring inhibitors: current topics in smooth muscle physiology and chemical biology 1 2 3 1 Akira Takai • Masumi Eto • Katsuya Hirano • Kosuke Takeya • 4 5 Toshiyuki Wakimoto • Masaru Watanabe Received: 6 January 2017 / Accepted: 27 June 2017 / Published online: 5 July 2017 Ó The Author(s) 2017. This article is an open access publication Abstract Protein phosphatases 1 and 2A (PP1 and PP2A) Keywords Protein phosphorylation Á Protein phosphatase are the most ubiquitous and abundant serine/threonine 1 Á Protein phosphatase 2A Á Smooth muscle Á Phosphatase phosphatases in eukaryotic cells. They play fundamental inhibitors Á Signal transduction roles in the regulation of various cellular functions. This review focuses on recent advances in the functional studies of these enzymes in the field of smooth muscle physiology. Introduction Many naturally occurring protein phosphatase inhibitors with different relative PP1/PP2A affinities have been dis- Protein phosphatases 1 (PP1) and 2A (PP2A) are two of the covered and are widely used as powerful research tools. principal catalytic subunits that dephosphorylate proteins on Current topics in the chemical biology of PP1/PP2A inhi- serine and threonine residues in the cytosol of eukaryotic bitors are introduced and discussed, highlighting the cells. They are encoded by genes belonging to the PPP identification of the gene cluster responsible for the family and are abundantly expressed in all cell types. These biosynthesis of calyculin A in a symbiont microorganism enzymes achieve the substrate specificity and activity reg- of a marine sponge.
    [Show full text]
  • Principles and Practice of Forest Landscape Restoration Case Studies from the Drylands of Latin America Edited by A.C
    Principles and Practice of Forest Landscape Restoration Case studies from the drylands of Latin America Edited by A.C. Newton and N. Tejedor About IUCN IUCN, International Union for Conservation of Nature, helps the world find pragmatic solutions to our most pressing environment and development challenges. IUCN works on biodiversity, climate change, energy, human livelihoods and greening the world economy by supporting scientific research, managing field projects all over the world, and bringing governments, NGOs, the UN and companies together to develop policy, laws and best practice. IUCN is the world’s oldest and largest global environmental organization, with more than 1,000 government and NGO members and almost 11,000 volunteer experts in some 160 countries. IUCN’s work is supported by over 1,000 staff in 60 offices and hundreds of partners in public, NGO and private sectors around the world. www.iucn.org Principles and Practice of Forest Landscape Restoration Case studies from the drylands of Latin America Principles and Practice of Forest Landscape Restoration Case studies from the drylands of Latin America Edited by A.C. Newton and N. Tejedor This book is dedicated to the memory of Margarito Sánchez Carrada, a student who worked on the research project described in these pages. The designation of geographical entities in this book, and the presentation of the material, do not imply the expression of any opinion whatsoever on the part of IUCN or the European Commission concerning the legal status of any country, territory, or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries.
    [Show full text]
  • DPR Journal 2016 Corrected Final.Pmd
    Bul. Dept. Pl. Res. No. 38 (A Scientific Publication) Government of Nepal Ministry of Forests and Soil Conservation Department of Plant Resources Thapathali, Kathmandu, Nepal 2016 ISSN 1995 - 8579 Bulletin of Department of Plant Resources No. 38 PLANT RESOURCES Government of Nepal Ministry of Forests and Soil Conservation Department of Plant Resources Thapathali, Kathmandu, Nepal 2016 Advisory Board Mr. Rajdev Prasad Yadav Ms. Sushma Upadhyaya Mr. Sanjeev Kumar Rai Managing Editor Sudhita Basukala Editorial Board Prof. Dr. Dharma Raj Dangol Dr. Nirmala Joshi Ms. Keshari Maiya Rajkarnikar Ms. Jyoti Joshi Bhatta Ms. Usha Tandukar Ms. Shiwani Khadgi Mr. Laxman Jha Ms. Ribita Tamrakar No. of Copies: 500 Cover Photo: Hypericum cordifolium and Bistorta milletioides (Dr. Keshab Raj Rajbhandari) Silene helleboriflora (Ganga Datt Bhatt), Potentilla makaluensis (Dr. Hiroshi Ikeda) Date of Publication: April 2016 © All rights reserved Department of Plant Resources (DPR) Thapathali, Kathmandu, Nepal Tel: 977-1-4251160, 4251161, 4268246 E-mail: [email protected] Citation: Name of the author, year of publication. Title of the paper, Bul. Dept. Pl. Res. N. 38, N. of pages, Department of Plant Resources, Kathmandu, Nepal. ISSN: 1995-8579 Published By: Mr. B.K. Khakurel Publicity and Documentation Section Dr. K.R. Bhattarai Department of Plant Resources (DPR), Kathmandu,Ms. N. Nepal. Joshi Dr. M.N. Subedi Reviewers: Dr. Anjana Singh Ms. Jyoti Joshi Bhatt Prof. Dr. Ram Prashad Chaudhary Mr. Baidhya Nath Mahato Dr. Keshab Raj Rajbhandari Ms. Rose Shrestha Dr. Bijaya Pant Dr. Krishna Kumar Shrestha Ms. Shushma Upadhyaya Dr. Bharat Babu Shrestha Dr. Mahesh Kumar Adhikari Dr. Sundar Man Shrestha Dr.
    [Show full text]
  • Price List Aug.2020
    MALILIKO Prices are subject to change without notice. ESSENTIAL OILS SD: Steam distilled CP: Cold pressed SE: Solvent extracted Name Botanical name Extract. Part of plant Country Price/5ml Method All Spice Pimenta dioica SD Berry Jamaica 7.00 Angelica seed, organic 10% Angelica archangelica SD Seed England Angelica root, organic 10% Angelica archangelica SD Root France 13.00 Aniseed, wild Pimpinella anisum SD Seed Spain Basil Holy, organic Ocimum sanctum SD Herb India 11.50 Basil Sweet, Linalool, organic Ocimum basilicum SD Herb Egypt 11.00 Bay Laurel Laurus noblis SD Leaf Spain 9.50 Bay Pimenta, wild Pimenta racemosa SD Leaf West Indies 6.50 Benzoin Styrax benzoin SE Resin Sumatra Bergamot, organic Citrus bergamia CP Peel Italy 13.50 Bergamot FCF, organic Citrus bergamia CP Peel Italy 12.00 Bergamot FCF Citrus bergamia CP Peel Italy 9.00 Bergamot mint, wild Mentha citrata SD Herb India 9.50 Birch Sweet, wild Betula lenta SD Bark USA 8.00 Black Pepper Piper nigrum SD Dried fruit India 13.00 Black Pepper, organic Piper nigrum SD Dried fruit Madagascar 11.00 Black Pepper Piper nigrum SD Dried fruit India 7.00 Black Spruce, wild Picea mariana SD Needle Canada 8.00 Cajeput, organic Melaleuca leucadendron SD Leaf Vietnam 6.00 Cajeput Melaleuca leucadendron SD Leaf China 5.00 Camphor White Cinnamomum camphora SD Wood,branch China 5.00 Carrot seed Daucus carota SD Seed France 14.00 Cedar wood Atlas Cedrus atlantica SD Wood Morocco 6.00 Cedar wood Himalayan, wild Cerdrus deodora SD Wood India/Himalaya 5.50 Cedar wood Virginiana, wild Juniperus virginiana SD Wood USA 5.50 Chamomile German, org.
    [Show full text]
  • Gori River Basin Substate BSAP
    A BIODIVERSITY LOG AND STRATEGY INPUT DOCUMENT FOR THE GORI RIVER BASIN WESTERN HIMALAYA ECOREGION DISTRICT PITHORAGARH, UTTARANCHAL A SUB-STATE PROCESS UNDER THE NATIONAL BIODIVERSITY STRATEGY AND ACTION PLAN INDIA BY FOUNDATION FOR ECOLOGICAL SECURITY MUNSIARI, DISTRICT PITHORAGARH, UTTARANCHAL 2003 SUBMITTED TO THE MINISTRY OF ENVIRONMENT AND FORESTS GOVERNMENT OF INDIA NEW DELHI CONTENTS FOREWORD ............................................................................................................ 4 The authoring institution. ........................................................................................................... 4 The scope. .................................................................................................................................. 5 A DESCRIPTION OF THE AREA ............................................................................... 9 The landscape............................................................................................................................. 9 The People ............................................................................................................................... 10 THE BIODIVERSITY OF THE GORI RIVER BASIN. ................................................ 15 A brief description of the biodiversity values. ......................................................................... 15 Habitat and community representation in flora. .......................................................................... 15 Species richness and life-form
    [Show full text]
  • Principles and Practice of Forest Landscape Restoration Case Studies from the Drylands of Latin America Edited by A.C
    Principles and Practice of Forest Landscape Restoration Case studies from the drylands of Latin America Edited by A.C. Newton and N. Tejedor About IUCN IUCN, International Union for Conservation of Nature, helps the world find pragmatic solutions to our most pressing environment and development challenges. IUCN works on biodiversity, climate change, energy, human livelihoods and greening the world economy by supporting scientific research, managing field projects all over the world, and bringing governments, NGOs, the UN and companies together to develop policy, laws and best practice. IUCN is the world’s oldest and largest global environmental organization, with more than 1,000 government and NGO members and almost 11,000 volunteer experts in some 160 countries. IUCN’s work is supported by over 1,000 staff in 60 offices and hundreds of partners in public, NGO and private sectors around the world. www.iucn.org Principles and Practice of Forest Landscape Restoration Case studies from the drylands of Latin America Principles and Practice of Forest Landscape Restoration Case studies from the drylands of Latin America Edited by A.C. Newton and N. Tejedor This book is dedicated to the memory of Margarito Sánchez Carrada, a student who worked on the research project described in these pages. The designation of geographical entities in this book, and the presentation of the material, do not imply the expression of any opinion whatsoever on the part of IUCN or the European Commission concerning the legal status of any country, territory, or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries.
    [Show full text]
  • Trade-Offs Between Drought Survival and Rooting Strategy of Two South American Mediterranean Tree Species: Implications for Dryland Forests Restoration
    Forests 2015, 6, 3733-3747; doi:10.3390/f6103733 OPEN ACCESS forests ISSN 1999-4907 www.mdpi.com/journal/forests Article Trade-Offs between Drought Survival and Rooting Strategy of Two South American Mediterranean Tree Species: Implications for Dryland Forests Restoration Juan F. Ovalle 1, Eduardo C. Arellano 1,2,* and Rosanna Ginocchio 1,2 1 Center of Applied Ecology & Sustainability, Avenida Libertador Bernardo O’Higgins 340, Santiago 8320000, Chile; E-Mails: [email protected] (J.F.O.); [email protected] (R.G.) 2 Departamento de Ecosistemas y Medio Ambiente, Facultad de Agronomía e Ingeniería Forestal, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna 4860, Santiago 8320000, Chile * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +56-2-2354-1216. Academic Editors: M. Altaf Arain and Eric J. Jokela Received: 18 August 2015 / Accepted: 10 October 2015 / Published: 15 October 2015 Abstract: Differences in water-acquisition strategies of tree root systems can determine the capacity to survive under severe drought. We evaluate the effects of field water shortage on early survival, growth and root morphological variables of two South American Mediterranean tree species with different rooting strategies during two growing seasons. One year-old Quillaja saponaria (deep-rooted) and Cryptocarya alba (shallow-rooted) seedlings were established under two watering treatments (2 L·week−1·plant−1 and no water) in a complete randomized design. Watering improved the final survival of both species, but the increase was only significantly higher for the shallow-rooted species. The survival rates of deep- and shallow-rooted species was 100% and 71% with watering treatment, and 96% and 10% for the unwatered treatment, respectively.
    [Show full text]
  • Chec List What Survived from the PLANAFLORO Project
    Check List 10(1): 33–45, 2014 © 2014 Check List and Authors Chec List ISSN 1809-127X (available at www.checklist.org.br) Journal of species lists and distribution What survived from the PLANAFLORO Project: PECIES S Angiosperms of Rondônia State, Brazil OF 1* 2 ISTS L Samuel1 UniCarleialversity of Konstanz, and Narcísio Department C.of Biology, Bigio M842, PLZ 78457, Konstanz, Germany. [email protected] 2 Universidade Federal de Rondônia, Campus José Ribeiro Filho, BR 364, Km 9.5, CEP 76801-059. Porto Velho, RO, Brasil. * Corresponding author. E-mail: Abstract: The Rondônia Natural Resources Management Project (PLANAFLORO) was a strategic program developed in partnership between the Brazilian Government and The World Bank in 1992, with the purpose of stimulating the sustainable development and protection of the Amazon in the state of Rondônia. More than a decade after the PLANAFORO program concluded, the aim of the present work is to recover and share the information from the long-abandoned plant collections made during the project’s ecological-economic zoning phase. Most of the material analyzed was sterile, but the fertile voucher specimens recovered are listed here. The material examined represents 378 species in 234 genera and 76 families of angiosperms. Some 8 genera, 68 species, 3 subspecies and 1 variety are new records for Rondônia State. It is our intention that this information will stimulate future studies and contribute to a better understanding and more effective conservation of the plant diversity in the southwestern Amazon of Brazil. Introduction The PLANAFLORO Project funded botanical expeditions In early 1990, Brazilian Amazon was facing remarkably in different areas of the state to inventory arboreal plants high rates of forest conversion (Laurance et al.
    [Show full text]
  • Annona Muricata L. = Soursop = Sauersack Guanabana, Corosol
    Annona muricata L. = Soursop = Sauersack Guanabana, Corosol, Griarola Guanábana Guanábana (Annona muricata) Systematik Einfurchenpollen- Klasse: Zweikeimblättrige (Magnoliopsida) Unterklasse: Magnolienähnliche (Magnoliidae) Ordnung: Magnolienartige (Magnoliales) Familie: Annonengewächse (Annonaceae) Gattung: Annona Art: Guanábana Wissenschaftlicher Name Annona muricata Linnaeus Frucht aufgeschnitten Zweig, Blätter, Blüte und Frucht Guanábana – auch Guyabano oder Corossol genannt – ist eine Baumart, aus der Familie der Annonengewächse (Annonaceae). Im Deutschen wird sie auch Stachelannone oder Sauersack genannt. Inhaltsverzeichnis [Verbergen] 1 Merkmale 2 Verbreitung 3 Nutzen 4 Kulturgeschichte 5 Toxikologie 6 Quellen 7 Literatur 8 Weblinks Merkmale [Bearbeiten] Der Baum ist immergrün und hat eine nur wenig verzweigte Krone. Er wird unter normalen Bedingungen 8–12 Meter hoch. Die Blätter ähneln Lorbeerblättern und sitzen wechselständig an den Zweigen. Die Blüten bestehen aus drei Kelch- und Kronblättern, sind länglich und von grüngelber Farbe. Sie verströmen einen aasartigen Geruch und locken damit Fliegen zur Bestäubung an. Die Frucht des Guanábana ist eigentlich eine große Beere. Sie wird bis zu 40 Zentimeter lang und bis zu 4 Kilogramm schwer. In dem weichen, weißen Fruchtfleisch sitzen große, schwarze (giftige) Samen. Die Fruchthülle ist mit weichen Stacheln besetzt, welche die Überreste des weiblichen Geschlechtsapparates bilden. Die Stacheln haben damit keine Schutzfunktion gegenüber Fraßfeinden. Verbreitung [Bearbeiten] Die Stachelannone
    [Show full text]
  • Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae)
    Biomolecules 2015, 5, 910-942; doi:10.3390/biom5020910 OPEN ACCESS biomolecules ISSN 2218-273X www.mdpi.com/journal/biomolecules/ Review Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae) Bruno Ndjakou Lenta 1,2,*, Jean Rodolphe Chouna 3, Pepin Alango Nkeng-Efouet 3 and Norbert Sewald 2 1 Department of Chemistry, Higher Teacher Training College, University of Yaoundé 1, P.O. Box 47, Yaoundé, Cameroon 2 Organic and Bioorganic Chemistry, Chemistry Department, Bielefeld University, P.O. Box 100131, 33501 Bielefeld, Germany; E-Mail: [email protected] 3 Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon; E-Mails:[email protected] (J.R.C.); [email protected] (P.A.N.-E.) * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +2376-7509-7561. Academic Editor: Jürg Bähler Received: 3 March 2015 / Accepted: 6 May 2015 / Published: 14 May 2015 Abstract: Plants of the Lauraceae family are widely used in traditional medicine and are sources of various classes of secondary metabolites. Two genera of this family, Beilschmiedia and Endiandra, have been the subject of numerous investigations over the past decades because of their application in traditional medicine. They are the only source of bioactive endiandric acid derivatives. Noteworthy is that their biosynthesis contains two consecutive non-enzymatic electrocyclic reactions. Several interesting biological activities for this specific class of secondary metabolites and other constituents of the two genera have been reported, including antimicrobial, enzymes inhibitory and cytotoxic properties. This review compiles information on the structures of the compounds described between January 1960 and March 2015, their biological activities and information on endiandric acid biosynthesis, with 104 references being cited.
    [Show full text]