Structure of the Stem
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Tropane and Granatane Alkaloid Biosynthesis: a Systematic Analysis
Office of Biotechnology Publications Office of Biotechnology 11-11-2016 Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis Neill Kim Texas Tech University Olga Estrada Texas Tech University Benjamin Chavez Texas Tech University Charles Stewart Jr. Iowa State University, [email protected] John C. D’Auria Texas Tech University Follow this and additional works at: https://lib.dr.iastate.edu/biotech_pubs Part of the Biochemical and Biomolecular Engineering Commons, and the Biotechnology Commons Recommended Citation Kim, Neill; Estrada, Olga; Chavez, Benjamin; Stewart, Charles Jr.; and D’Auria, John C., "Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis" (2016). Office of Biotechnology Publications. 11. https://lib.dr.iastate.edu/biotech_pubs/11 This Article is brought to you for free and open access by the Office of Biotechnology at Iowa State University Digital Repository. It has been accepted for inclusion in Office of Biotechnology Publicationsy b an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis Abstract The tropane and granatane alkaloids belong to the larger pyrroline and piperidine classes of plant alkaloids, respectively. Their core structures share common moieties and their scattered distribution among angiosperms suggest that their biosynthesis may share common ancestry in some orders, while they may be independently derived in others. Tropane and granatane alkaloid diversity arises from the myriad modifications occurring ot their core ring structures. Throughout much of human history, humans have cultivated tropane- and granatane-producing plants for their medicinal properties. This manuscript will discuss the diversity of their biological and ecological roles as well as what is known about the structural genes and enzymes responsible for their biosynthesis. -
A Molecular Phylogeny of the Solanaceae
TAXON 57 (4) • November 2008: 1159–1181 Olmstead & al. • Molecular phylogeny of Solanaceae MOLECULAR PHYLOGENETICS A molecular phylogeny of the Solanaceae Richard G. Olmstead1*, Lynn Bohs2, Hala Abdel Migid1,3, Eugenio Santiago-Valentin1,4, Vicente F. Garcia1,5 & Sarah M. Collier1,6 1 Department of Biology, University of Washington, Seattle, Washington 98195, U.S.A. *olmstead@ u.washington.edu (author for correspondence) 2 Department of Biology, University of Utah, Salt Lake City, Utah 84112, U.S.A. 3 Present address: Botany Department, Faculty of Science, Mansoura University, Mansoura, Egypt 4 Present address: Jardin Botanico de Puerto Rico, Universidad de Puerto Rico, Apartado Postal 364984, San Juan 00936, Puerto Rico 5 Present address: Department of Integrative Biology, 3060 Valley Life Sciences Building, University of California, Berkeley, California 94720, U.S.A. 6 Present address: Department of Plant Breeding and Genetics, Cornell University, Ithaca, New York 14853, U.S.A. A phylogeny of Solanaceae is presented based on the chloroplast DNA regions ndhF and trnLF. With 89 genera and 190 species included, this represents a nearly comprehensive genus-level sampling and provides a framework phylogeny for the entire family that helps integrate many previously-published phylogenetic studies within So- lanaceae. The four genera comprising the family Goetzeaceae and the monotypic families Duckeodendraceae, Nolanaceae, and Sclerophylaceae, often recognized in traditional classifications, are shown to be included in Solanaceae. The current results corroborate previous studies that identify a monophyletic subfamily Solanoideae and the more inclusive “x = 12” clade, which includes Nicotiana and the Australian tribe Anthocercideae. These results also provide greater resolution among lineages within Solanoideae, confirming Jaltomata as sister to Solanum and identifying a clade comprised primarily of tribes Capsiceae (Capsicum and Lycianthes) and Physaleae. -
Application of Metabolic Engineering to the Production of Scopolamine
Molecules 2008, 13, 1722-1742; DOI: 10.3390/molecules13081722 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.org/molecules Review Application of Metabolic Engineering to the Production of Scopolamine Javier Palazón 1,*, Arturo Navarro-Ocaña 2, Liliana Hernandez-Vazquez 1 and Mohammad Hossein Mirjalili 3 1 Laboratori de Fisiologia Vegetal, Facultat de Farmacia, Universitat de Barcelona, Avda Diagonal 643, E-08028 Barcelona, Spain; E-mail: [email protected] 2 Departamento de Alimentos y Biotecnologia, Facultad de Química, Universidad Nacional Autónoma de México, México DF, México; E-mail: [email protected] 3 Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran; E-mail: [email protected] * Author to whom correspondence should be addressed; E-mail: [email protected]. Received: 3 June 2008; in revised form: 12 August 2008 / Accepted: 14 August 2008 / Published: 18 August 2008 Abstract: Scopolamine is an alkaloid widely used in medicine for its anticholinergic activity. The aim of this review is to show that metabolic engineering techniques constitute a suitable tool to improve the production of tropane alkaloids, focusing in particular on scopolamine. We present an overview of results obtained by various research groups, including our own, who have studied the overexpression of genes involved in the biosynthesis of scopolamine in different plant species that produce tropane alkaloids. Experiments carried out to improve production in hairy root cultures will also be described, as well as those attempting to biotransform hyoscyamine into scopolamine in roots and transgenic tobacco cells. Keywords: Scopolamine, hyoscyamine, hairy roots, putrescine N-methyltransferase, hyoscyamine-6-β-hydroxylase. Molecules 2008, 13 1723 Introduction In developing countries, plants are the main source of medicines: according to the World Health Organization, as much as 80% of the world’s population in developing countries relies on traditional medicine for its primary health care, and this is mainly based on plant remedies. -
Tropane the Bicyclic Amine That Is the Precursor to ~ $4 Billion Pharmaceutical Industries QH
Tropane The bicyclic amine that is the precursor to ~ $4 billion pharmaceutical industries QH Shahjalal University of Science & Technology, Bangladesh. Molecule of the Month – June 2012 What is tropane? Tropane is a bicyclic amine that has a pyrrolidine and a piperidine ring sharing a common nitrogen atom and 2 carbon atoms. It is the common structural element of all tropane alkaloids (Lounasmaa and Tamminen, 1993). Fig. 1 Tropane; (1R, 5S)-8-methyl-8-azabicyclo [3.2.1] octane In what form is it found in nature or used as? Tropane does not occur naturally in free form rather it is found as part of esters in plant species. Esters of tropane are generally secondary metabolites of these plants. Fig. 2 Some natural esters of tropane Almost all of the tropane based pharmaceuticals are natural or semi-synthetic esters. There are also alkylated or arylated tropane-compounds known as phenyltropanes. Fig. 3 Arylated or alkylated tropane (left) and semi-synthetic esters (right) Why is tropane important? Tropane derivatives are among the economically most important pharmaceuticals (Rates 2001; Raskin 2002). Various pharmaceutical industries are manufacturing over 20 active pharmaceutical ingredients (APIs) containing the tropane moiety in their structures; they are applied as mydriatics, antiemetics, antispasmodics, anesthetics, and bronchodilators (Grynkiewicz and Gadzikowska, 2008). Fig. 4 Tropane in APIs, their major applications, and annual global revenue When was its chemistry developed? Although alkaloids with the tropane moiety are the oldest medicines known to man, only recently they have been isolated, purified and studied. K. Mein First to isolate atropine in 1831 P. L. Geiger First to isolate hyoscyamine in 1833 Friedrich Gaedcke First to isolate cocaine in 1855 K. -
The Coloured Atlas of Medicinal and Aromatic Plants of Jordan and Their Uses (Volume Three)
The Coloured Atlas of Medicinal and Aromatic Plants of Jordan and Their Uses (Volume Three) The Coloured Atlas of Medicinal and Aromatic Plants of Jordan and Their Uses (Volume Three) By Jamal Ragheb Said Qasem The Coloured Atlas of Medicinal and Aromatic Plants of Jordan and Their Uses (Volume Three) By Jamal Ragheb Said Qasem This book first published 2020 Cambridge Scholars Publishing Lady Stephenson Library, Newcastle upon Tyne, NE6 2PA, UK British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library Copyright © 2020 by Jamal Ragheb Said Qasem All rights for this book reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without the prior permission of the copyright owner. ISBN (10): 1-5275-4561-X ISBN (13): 978-1-5275-4561-8 DEDICATION • In the name of God, who created, invented and sustained all these wonderful, valuable, diverse plant species, His mercy and His blessing, and who said “We will show them our signs in the horizons and within themselves until it becomes clear to them that it is the truth. But is it not sufficient concerning your Lord that He is, over all things, a Witness?” (Sura Fussilat 041-053). • To my homeland and to all who bless its soil. • To the memory of my parents, who made sacrifices for my education and taught me that the land is faith and life. • To all my grandchildren, to learn and to know the value of the source and the product. -
Molecular Cloning and Characterization of a New Cdna Encoding Hyoscyamine 6Β-Hydroxylase from Roots of Anisodus Acutangulus
Journal of Biochemistry and Molecular Biology, Vol. 40, No. 5, September 2007, pp. 715-722 Molecular Cloning and Characterization of a New cDNA Encoding Hyoscyamine 6β-hydroxylase from Roots of Anisodus acutangulus Guoyin Kai1,*, Junfeng Chen1, Li Li1, Genyu Zhou1, Limin Zhou1, Lei Zhang2, Yuhui Chen3 and Linxia Zhao3 1Laboratory of Plant Biotechnology, College of Life and Environment Sciences, Shanghai Normal University, Shanghai 200234, People’s Republic of China 2School of Pharmacy, Second Military Medical University, Shanghai 200433, People’s Republic of China 3Fudan-SJTU-Nottingham Plant Biotechnology R&D Center, School of Agriculture and Biology, Shanghai Jiaotong University, Shanghai 200030, People’s Republic of China Received 29 January 2007, Accepted 23 April 2007 A new full-length cDNA encoding hyoscyamine 6β- Keywords: Anisodus acutangulus, Bioinformatics analysis, hydroxylase (designated as aah6h, GenBank Accession No. Expression pattern, Hyoscyamine 6β-hydroxylase (H6H), EF187826), which catalyzes the last committed step in the Southern blotting scopolamine biosynthetic pathway, was isolated from young roots of Anisodus acutangulus by rapid amplification of cDNA ends (RACE) for the first time. The full-length cDNA of aah6h was 1380 bp and contained a 1035 bp open Introduction reading frame (ORF) encoding a deduced protein of 344 amino acid residues. The deduced protein had an A few genera of the plant family Solanaceae icluding isoelectric point (pI) of 5.09 and a calculated molecular Anisodus, Atropa, Datura, Duboisia, Hyoscyamus and mass of about 38.7 kDa. Sequence analyses showed that Scopolia are able to produce biologically active tropane AaH6H had high homology with other H6Hs isolated from alkaloids simultaneously (Hsiao et al., 1973; Endo et al., some scopolamine-producing plants such as Hyoscyamus 1991; Christen et al., 1993; Hashimoto and Yamada 1994; niger, Datura metel and Atropa belladonna etc. -
Solanaceae) Growing in Turkey
Bangladesh J. Bot. 44(1): 37-43, 2015 (March) COMPARATIVE ANATOMICAL STUDIES ON SOME SPECIES OF HYOSCYAMUS L. (SOLANACEAE) GROWING IN TURKEY 1 FATIİH SATIL, MUSTAFA ASLAN , EYÜP ERDOĞAN*, 2 3 RIDVAN POLAT AND SELAMİ SELVİ Department of Biology, Faculty of Science & Art, Balıkesir University, Çağış Campus, 10145 Balıkesir, Turkey Key words: Comparative anatomy, Leaf, Stem, Hyoscyamus, Solanaceae Abstract A comparative study based on leaf and stem anatomical structure was made using light microscopy (LM) techniques on five species of Hyoscyamus L. (Solanaceae) in Turkey. Some characters are found important to distinguish the species within the genera. The investigated species can be divided as mesophyll type: bifacial (H. niger L., H. albus L. ) and equifacial (H. aureus L., H. pusillus L., H. reticulatus L.). Druse crystals are recorded only in mesophyll of H. albus. Stomata present on both surfaces, are anisocytic (usually) and anomocytic types. H. reticulatus can be distinguished from other species considering types of trichomes in the stem. Vascular bundles are bicollateral types. Introduction The cosmopolitan Solanaceae family includes 102 genera with 2460 species in the world. In Turkey, there are 12 genera and 36 species of the Solanaceae and most of them are wild herbs (Erik and Tarıkahya 2004; Selvi et al. 2009). The plants of this family are well known as a natural source of tropan alkaloids including hyoscyamine, scopolamine and atropine (Kartle et al. 2003) and are cultivated for their medicinal importance (Etminan et al. 2012). The genus Hyoscyamus occupies the phyto-geographical region of Sino-Japanese. Hyoscyamus a small herbaceous genus having 26 species all over the world (Yousaf et al. -
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J. Plant Protection and Pathology, Mansoura University, Vol.1(8): 627 - 633, 2010 EFFICIENCY OF CERTAIN PLANT EXTRARACTS ON Aphis craccivoa koch. AND Chrysoperla carnea (STEPH) IN SOUTHERN VALLEY, EGYPT. El-Arnaouty, S. A.*; E. A. Eweis* and H. A. Haddad** * Dept. Economic Entomology and pesticides, Fac. Agric., Cairo Univ. ** Center of Bio-Organic Agricultural Services, Aswan, Egypt ABSTRACT Two plants; Hyoscyamus muticus and Ambrosia maritime were chosen in order to investigate the toxticty of their leave, stem, flower or root extracts (using ethanol, acetone, chloroform and hexane) to nymph and adults of Aphis craccivora and its predator Chrysoperla carnea. The plant extracts were treated using direct spraying on infested bean seedlings. The results showed that for the two plant species, high concentration of leave extract in ethanol and acetone gave a high mortality rate after 24 and 48 h. For the flower extracts, high concentration in ethanol and chloroform resulted as well in high mortality rate of the pest after 24 and 48 h. As far as the root extracts are concerned only H.muticus at a high concentration in ethanol gave high mortality rate after 24 and 48 h. For the stem extracts, only H.muticus, at a high concentration in hexane resulted in a high mortality rate after 24 and 48 h. Moreover these high plant extract concentration were not detrimental Ch. carnea and thus can be considered as safe adjuvant in the prospect of integrated pest control. Keywords: Plant extract, Aphis craccivora Koch, Chrysoperla carnea (Steph.) INTRODUCTION The relations between human and plant have been very close throughout the development of human cultures. -
Solanaceae) from the New World to Eurasia in the Early Miocene and Their Biogeographic Diversification Within Eurasia ⇑ ⇑⇑ Tieyao Tu A,1, Sergei Volis B, Michael O
Molecular Phylogenetics and Evolution 57 (2010) 1226–1237 Contents lists available at ScienceDirect Molecular Phylogenetics and Evolution journal homepage: www.elsevier.com/locate/ympev Dispersals of Hyoscyameae and Mandragoreae (Solanaceae) from the New World to Eurasia in the early Miocene and their biogeographic diversification within Eurasia ⇑ ⇑⇑ Tieyao Tu a,1, Sergei Volis b, Michael O. Dillon c, Hang Sun a, , Jun Wen a,d, a Key Laboratory of Biodiversity and Biogeography, Kunming Institute of Botany, Chinese Academic of Sciences, Kunming 650204, PR China b Department of Life Science, Ben Gurion University of the Negev, Israel c Department of Botany, The Field Museum, 1400 South Lake Shore Drive, Chicago, IL, USA d Department of Botany, National Museum of Natural History, Smithsonian Institution, Washington, DC, USA article info abstract Article history: The cosmopolitan Solanaceae contains 21 tribes and has the greatest diversity in South America. Received 1 June 2010 Hyoscyameae and Mandragoreae are the only tribes of this family distributed exclusively in Eurasia Revised 8 September 2010 with two centers of diversity: the Mediterranean–Turanian (MT) region and the Tibetan Plateau (TP). Accepted 9 September 2010 In this study, we examined the origins and biogeographical diversifications of the two tribes based Available online 19 September 2010 on the phylogenetic framework and chronogram inferred from a combined data set of six plastid DNA regions (the atpB gene, the ndhF gene, the rps16-trnK intergenic spacer, the rbcL gene, the trnC- Keywords: psbM region and the psbA-trnH intergenic spacer) with two fossil calibration points. Our data suggest Biogeography that Hyoscyameae and Mandragoreae each forms a monophyletic group independently derived from Disjunction Dispersal different New World lineages in the early Miocene. -
Genetically Engineered Hairy Root Cultures of Hyoscyamus Senecionis and H
NRC Publications Archive Archives des publications du CNRC Genetically engineered hairy root cultures of Hyoscyamus senecionis and H. muticus: ploidy as a promising parameter in the metabolic engineering of tropane alkaloids Dehghan, E.; Reed, D. W.; Covello, P. S.; Hasanpour, Z.; Palazon, J.; Oksman-Caldentey, K. M.; Ahmadi, F. S This publication could be one of several versions: author’s original, accepted manuscript or the publisher’s version. / La version de cette publication peut être l’une des suivantes : la version prépublication de l’auteur, la version acceptée du manuscrit ou la version de l’éditeur. For the publisher’s version, please access the DOI link below./ Pour consulter la version de l’éditeur, utilisez le lien DOI ci-dessous. Publisher’s version / Version de l'éditeur: https://doi.org/10.1007/s00299-017-2178-0 Plant Cell Reports, 2017-07-13 NRC Publications Record / Notice d'Archives des publications de CNRC: https://nrc-publications.canada.ca/eng/view/object/?id=eb694767-af9a-4600-9206-72799a8bad9d https://publications-cnrc.canada.ca/fra/voir/objet/?id=eb694767-af9a-4600-9206-72799a8bad9d Access and use of this website and the material on it are subject to the Terms and Conditions set forth at https://nrc-publications.canada.ca/eng/copyright READ THESE TERMS AND CONDITIONS CAREFULLY BEFORE USING THIS WEBSITE. L’accès à ce site Web et l’utilisation de son contenu sont assujettis aux conditions présentées dans le site https://publications-cnrc.canada.ca/fra/droits LISEZ CES CONDITIONS ATTENTIVEMENT AVANT D’UTILISER CE SITE WEB. Questions? Contact the NRC Publications Archive team at [email protected]. -
Study of Inheritance and Environment on Tropane Alkaloids Within Hyoscyamus Species
AJCS 6(10):1428-1434 (2012) ISSN:1835-2707 Study of inheritance and environment on tropane alkaloids within Hyoscyamus species Fatemeh Nejadhabibvash*1, Fatemeh Rahmani1, Reza Heidari1, Rashid Jamei1 and Farzaneh Azimi2 1Department of Biology‚ Faculty of Science‚ Urmia University‚ Urmia, Iran 2Agriculture Research Center of Ardabil Herbarium, Ardabil, Iran *Corresponding author: [email protected] Abstract In the present study, HPLC technique was applied to determine scopolamine and hyoscyamine contents in five Hyoscyamus species including H.niger L., H.reticulatus L., H.pusillus L., H.arachnoideus Pojark., and H.kurdicus Bornm., collected from different geographical origins of North West of Iran. The range of genetic similarity was obtained between 91.07 and 99.89 within Hyoscyamus accessions based on scopolamine and hyoscyamine alkaloids composition. Estimated heritability was high for both traits and ranged from 0.82 to 0.99. The existance of high GCV indicates the genetical control of tropane alkaloids which leads us to achivement of genetic improvement by selection of desirable plants for breeding. Our data also implies the positive assosiation between N, P, K, Ca & EC and alkaloids yield in plants which will be useful for production programs in the future. Keywords: environment; hyoscyamine; HPLC; Iran; scopolamine. Abbreviations: HPLC-high performance liquid chromatography; GCV-genotypic coefficient of variability; PCV-phenotypic coefficient of variability; CV-coefficient of variability; LOD-limit of detection; LOQ-limit of quantification; RSD-relative standard deviation; EC-electrical conductivity; UPGMA-unweighted pair group method arithmetic average. Introduction The genus Hyoscyamus L. belongs to the tribe Hyoscyameae plant species, genotype, availability and mobility of the Miers of Solanaceae family with 18 species all over the minerals in the soil, soil properties, such as, pH, organic world (Yousaf et al., 2008) and 13 species in Iran matter, clay content and etc. -
Tropane Alkaloids Production from Callus Culture of Atropa Belladonna L
Mohamed I. Elshorbagy et al. Int. Res. J. Pharm. 2018, 9 (7) INTERNATIONAL RESEARCH JOURNAL OF PHARMACY www.irjponline.com ISSN 2230 – 8407 Research Article TROPANE ALKALOIDS PRODUCTION FROM CALLUS CULTURE OF ATROPA BELLADONNA L. AS AFFECTED BY ELICITORS AND PRECURSOR FEEDING Mohamed I. Elshorbagy 1*, Souzan M. Ibrahim 1, Kamilia A. Abo El-Seoud 1 and Ahmed I. Abd El-Maksoud 2 1Department of Pharmacognosy, Faculty of Pharmacy, Tanta University, Tanta (31527), Egypt 2Department of Industrial Biotechnology, Genetic Engineering and Biotechnology Research Institute, Sadat City University, Sadat City (32897), Egypt *Corresponding Author Email: [email protected] Article Received on: 03/07/18 Approved for publication: 30/07/18 DOI: 10.7897/2230-8407.097135 ABSTRACT Atropa belladonna L is most important commercial source of pharmaceutical tropane alkaloids. Initiation of callus culture on MS solid media with different concentrations of growth regulators as BA and 2,4 D from different explants shows that 2,4-D only at 1.0mg/L and 2.0mg/l gave the highest callus formation score after 21 days. The highest concentration of atropine (376.62 µg/g DW) and scopolamine (103.16 µg/g DW) were obtained from leaf callus on MS medium supplemented with 2,4 D at 0.5 mg/L after 28 days. The effect of elicitors and precursor feeding on tropane alkaloids production in callus culture were examined. Accumulation of both alkaloids; atropine and scopolamine in callus were enhanced after 8 days with jasmonic acid at concentrations (50 µM), after 15 days with yeast extract at concentrations (0.5 g/L) and after 21days with ornithine at 1mM in comparison with control callus.