DOCSLIB.ORG

<I>Triphyophyllum Peltatum</I>

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
<I>Triphyophyllum Peltatum</I> BIOLOGICALL Y ACTIVE AGENTS IN NATURE 18 CHIMIA 52 (1998) Nr. 1/2 (Jannar/Fcb"mr) Chimia 52 (1998) 18-28 methods. The first alkaloid to be investi- © Neue Sclnveizerische Chemische Gesellschaft gated was dioncophylline A [18][19], the ISSN 0009-4293 main secondary metabolite ofT. peltatum. It is easily accessible by standard isolation procedures, and was found to have a naph- The Alkaloids of Triphyophyllum thylisoquinoline basic structure mainly by NMR investigations (Fig. 4). It has three peltatum (Dioncophyllaceae) [1] stereogenic units: two stereocenters (C( I), C(3»and astereogenic axis (C(7) ~C(I'». Its structural elucidation thus requires at Gerhard Bringrnanna)*, Guido Fran~oisb), Laurent Ake Assn, and least three pieces of stereochemical infor- U Jan Schlauer ) mation. Dedicated to Professor Meinhart H. Zenk, University of Munich, on the occasion of his 2.1. The Relative Configuration at the 65th birthday. Stereocenters: through NMR From an NOE interaction of the axial proton at C(3) (Fig. 5) with the likewise Abstract. A great diversity of naphthylisoquinolines, presumably acetogenic biaryl axial Me group at C( 1), a relative cis-array alkaloids, has been obtained from the West-African liana Triphyophyllumpeltatum. By of these two spin systems and thus trans- the example of dioncophylline A, the main alkaloid from T. peltatum, we illustrate the orientation of the two Me groups was various methods of structural elucidation established in our laboratory. The structural deduced, establishing an (R,R)- (or an peculiarities of some of the minor alkaloids from the same species are discussed. A (5,5)-!) configuration [18] - the first re- perspective on the interesting biological activities of various alkaloids from T.peltatum quired stereochemical information. and related plants is given. The most promising lead is dioncophylline C, marked by pronounced antiplasmodial activity. Chemical syntheses, especially dimerization of 2.2. The Absolute Configuration at naphthylisoquinolines, and QSAR-guided modifications of the most active structures C(3) (and thus C(1)): through Total are featured as rewarding strategies in the search for improved drugs. A chemotaxo- Synthesis nomic summary is presented. The absolute configuration at C(3) was established by a stereochemically unam- 1. Introduction precursors, named korupensamines, into biguous total synthesis of the alkaloid micheUamines [13]. from alanine (Scheme 1) [19][20]. For the Dimeric naphthylisoquinoline alka- This paper will deal mainly with such regio- and stereoselective construction of loids, e.g. michellamine B (1, Fig. ]), are monomers, especially those from Tri- the biaryl axis, the 'lactone method' was most promising novel antiviral compounds phyophyllum peltatum, since they like- applied, an efficient synthetic procedure from African plants [2-4]. They occur in wise display intriguing structural, biosyn- developed in our group [21][22]: Prefix- one single species, Ancistrocladus koru- thetic, and pharmacological (in particular ation of the two molecular moieties via an pens is, which is endemic to a small region antimalarial) properties. T. peltatum is the ester bridge «(f 2) and subsequent in- at the Cameroonian/Nigerian border and most widespread species of the Dionco- tramolecularC,C-bond formation gave the has been discovered within an anti-HIV phyllaceae, a small plant family consist- lactone-bridged biaryl 3, which is config- screening program initiated by the US ing of only three species oflianas climbing uratively unstable - it rapidly isomerizes National Cancer Institute [5][6]. In collab- up high trees, by means of hooked leaves at the axis. But out of this equilibrium of oration with Dr. Boyd and his NCI group, (cf Fig. ]9) [14]. Unique are the large thin helimericforms3aand3b, itcan be cleaved we have elucidated the stereostructure of seeds with large membranous wings (Fig. such that optionally either ofthe atropiso- michellamine B and related compounds 2), which during maturation exceed the [2][6-8] and have achieved first total syn- size ofthe fruits they are borne from [15]. theses of these challenging and attractive From these seeds, we have succeeded in target molecules [9-12]. One of the latest cultivating juvenile plants of T. peltatum achievements of our group is the detection (Fig. 3). At the end of the juvenile growth and characterization of dimerization en- period, just before it starts climbing, T. zymes which transform the monomeric peltatum forms leaves with stalked glands and reduced lamina that capture and digest invertebrates [16]; it is a 'part-time' car- *Correspondence: Prof. Dr. G. Bringmann nivorous plant [17]. Phytochemically, T. a) Institut fUrOrganische Chemie der Universitat peltatum proved to be a rich source of Am Hubland D-97074 Wi.irzburg novel alkaloids. Tel.: +49931 8885323 Fax: +49 931 8884755 E-Mail: [email protected] 2. Dioncophylline A as a Probe Alka- b) Prins Leopold Instituut voor Tropische loid for the Analytical Methodology Geneeskunde Nationalestraat 155 For the rapid and unambiguous attri- B-2000 Antwerpen o configuratively unstable C) Centre National de Floristique bution of the full stereostructures of such Universite d' Abidjan compounds, we have established and fur- Fig. I. Michellamille n, a dimeric naphthyliso- 22 B.P. 582 Abidjan 22, Ivory Coast ther developed a broad series of analytical quinoline with high anti-HIV activity BIOLOGICALL Y ACTIVE AGENTS IN NATURE 19 CHIMIA 52 (1998) Nr. 1/2 (Jan"ar/Fehn,"r) Fig. 2. Seeds of Triphyophyllum peltatum (Dioncophyllaceae), showing Fig. 3. A juvenile plant ofT. peltatum, several weeks after germination the large circular wing meric products is obtained in high selec- possible conditions to avoid isomeriza- tivity [20] - a stereochemically efficient tion at the axis. From the positive first and mechanistically remarkable reaction. Cotton effect in the experimental CD spec- One of the products ultimately obtained is trum of 5, a likewise 'positive chirality' fully identical with natural dioncophylline was deduced, thus establishing P-config- A, whereas the other one is diastereomeric uration at the biaryl axis. - when starting from D-alanine, while L- alanine leads to the wrong enantiomeric 2.4. Further Support for the Axial series [19]. This shows dioncophylline A Configuration: Quantum Chemical CD to have (R)-configuration at C(3) (and Calculations thus also at C(l)) - the second stereoinfor- By these three pieces of stereoin- mation achieved. formation, the full absolute stereostruc- ture 4 of dioncophylline A as shown in 2.3. The Absolute Axial Configuration: Scheme 2 had become evident. Possibly Fig. 4. Constitution ofdioncophylline A by select- by Experimental CD Spectroscopy the same compound, but named 'triphyo- ed HMBC and NOE interactions and chemical While we had selectively produced phylline', had previously been isolated by shifts dioncophylline A and its stereoisomers, a French group [24][25], who had correct- its axial configuration was still unclear at ly assigned the constitution and the rela- ~H~N~Me this point. This missing third stereoinfor- tive configuration at C(l) and C(3), but 1 H 3 mation was acquired by CD spectroscopy, had erroneously assumed the absolute con- Me H for which the molecule first had to be figuration at the stereocenters to be (5,5), modified by dehydrogenation to give 5 so while the chirality of the biaryl axis had that, by enlargement of the isoquinoline been disregarded. Additional severe in- u chromophor, the Exciton Chirality meth- consistencies in the literature [24-26] ne- ~ trans od [23] became applicable (Scheme 2). cessitated a new naming for 4, subse- Fig. 5. Relative configuration at C( J) VS. C(2) of This had to be done under the mildest quently termed dioncophylline A [18]. dioncophylline A by NOE BIOLOGICALLY ACTIVE AGENTS IN NATURE 20 CHIMIA 52 (1998) Nr. 1/2 (JonunrlFebl1lnr) Scheme 1. Total Synthesis Establishing the Absolute Configuration at C(3) (and C(1)) e R 04- H02C~Me I • 04- Br:::"" R N .... ;::,... I R RN.... : Bn "\ MeO M ~(- Bn NH2 Wo Me HO Me 2 D-Ala o MeO CI 0 Me Me MeO Me MeO Me (rapid) 3a o - 7-epi- atropisomer- Dioncophylline A selective 1~fast cleavage ~ Me Me MeO - Me Me 3b MeO o Bn = CH Ph 2 (slow) Dioncophylline A m.p.214 o,[a]D-14.9 natural m.p.215°,[a]D-14 Scheme 2. Absolute Configuration at the Axis by Scheme 3. An Atropisomer-Dif.ferentiating Reaction for the Chemical Analysis of the Relative Exciton Chirality CD Configuration at the Axis 7-epi-6 (Dioncophylline A, full absolute stereostructure) 7-epi-4 4 PdlC ~ toluene, 1200 Me MeO MeO Forthis reason, we kept looking for further further developed in our group [27-29]. confirmation of our revised structure 4. As shown in Fig. 6, the theoretical CD Therefore, any new method that we in- spectrum (dotted) for the dehydrogena- troduced into naphthylisoquinoline chem- tion product of dioncophylline A matches istry was first tested on this important very well with the experimental one (full alkaloid, exemplarily. line), in particular in the region of the For a first additional support of the crucial couplet. This unambiguously con- absolute stereostructure, we have applied firms the absolute axial P-configuration the quantum chemical calculation and thus of dioncophylline A [30] - stereochemi- prediction of CD spectra, established and cal information no. 4. BIOLOGICALLY ACTIVE AGENTS IN NATURE 21 CHI MIA 52 (1998) Nr, 1/2 (Jnnunr/Fcbruor) 2.5. Relative Axial vs. Centrochirality: 200 positive first a Chemical Method / Cotton effect Furthermore, we have developed a 120 chemical method for the analysis of the .. relative configuration at the biaryl axis as 40 compared to the stereocenters [31]. Ofthe L1£ -40 two atropo-diastereomeric synthetic pre- -- experimental cursors 6 and 7 to dioncophylline A -epi-6 -120 calculated (4) and its atropisomer (7-epi-4) (Scheme A 3), specifically only the syn-compound 7- -200 epi-6 can be bridged by a succinate unit to 200 230 260 290 320 give 7, whereas the anti-diastereomer 6 Fig.
Load more

Recommended publications
  • Universidade Estadual Paulista Câmpus De
    Campus de Botucatu UNESP - UNIVERSIDADE ESTADUAL PAULISTA CÂMPUS DE BOTUCATU INSTITUTO DE BIOCIÊN CIAS GENÔMICA ORGANELAR E EVOLUÇÃO DE GENLISEA E UTRICULARIA (LENTIBULARIACEAE) SAURA RODRIGUES DA SILVA Tese apresentada ao Instituto de Biociências, Câmpus de Botucatu, UNESP, para obtenção do título de Doutor em Ciências Biológicas (Botânica) BOTUCATU - SP - 2018 - Insti tuto de Biociências – Departamento de Botânica Distrito de Rubião Júnior s/n CEP 18618 - 000 Botucatu SP Brasil Tel 14 3811 6265/6053 fax 14 3815 3744 [email protected] Campus de Botucatu UNESP - UNIVERSIDADE ESTADUAL PAULISTA CÂMPUS DE BOTUCATU INSTITUTO DE BIOCIÊN CIAS GENÔMICA ORGANELAR E EVOLUÇÃO DE GENLISEA E UTRICULARIA (LENTIBULARIACEAE) SAUR A RODRIGUES DA SILVA PROF. DR. VITOR FERN ANDES OLIVEIRA DE MI RANDA ORIENTADOR PROF. DR. ALESSANDRO DE MEL L O VARANI Coorientador Tese apresentada ao Instituto de Biociências, Câmpus de Botucatu, UNESP, para obtenção do título de Doutor em Ciên cias Biológicas (Botânica) BOTUCATU - SP - 2018 - Instituto de Biociências – Departamento de Botânica Distrito de Rubião Júnior s/n CEP 18618 - 000 Botucatu SP Brasil Tel 14 3811 6265/6053 fax 14 3815 3744 [email protected] 2 Campus de Botucatu FICHA CATALOGRÁFIC A ELABORADA PELA SEÇÃO TÉCNICA DE AQUISIÇÃO E TRATAMENTO DA INFORMAÇÃO DIVISÃO TÉCNICA DE BIBLIOTECA E DOCUMENTAÇÃO - CAMPUS DE BOTUCATU - UNESP Silva, Saura Rodrigues. Genômica organelar e evolução d e Genlisea e Utricularia (Lentibulariaceae) / Saura Rodrigues da Silva. – 2018. Tese (doutorado) – Universidade Estadual Paulista, Instituto de Biociências de Botucatu, 2018. Orientador: Vitor Fernandes Oliveira de Miranda Co - orientador: Alessandro de Mello Varani Assunto CAPES: 1. Sistemática Vegetal CDD 581.1 Palavras - c have: Utricularia ; Genlisea ; genômica de organelas; ndhs; Evolução de organelas.
    [Show full text]
  • (±)-Dioncophyllacine A, a Naphthylisoquinoline Alkaloid with a 4-Methoxy Substituent from the Leaves of Triphyophyllum Peltatum*
    Phytochemistry, Vo\. 31, No. 11, pp. 40154018,1992 0031-9422/92 $5.00 + 0.00 Printed in Great Britain. (!'J 1992 Pergamon Press Lld (±)-DIONCOPHYLLACINE A, A NAPHTHYLISOQUINOLINE ALKALOID WITH A 4-METHOXY SUBSTITUENT FROM THE LEAVES OF TRIPHYOPHYLLUM PELTATUM* GERHARD BRINGMANNt, THOMAS ORTMANN, RAINER ZAGST, BERND ScH6NER, LAURENT AKE ASSIt and CHRISTIAN BURSCHKA§ Institute of Organic Chemistry, University of Wiirzburg, Am Hubland, 0-8700 Wiirzburg, Germany; ~Centre National de Floristique (Conservatoire et Jardin Botaniques), Universite d'Abidjan, 22 b.p. 582 Abidjan 22, Ivory Coast; §Institute of Inorganic Chemistry, University of Wiirzburg, Am Hubland, D-8700 Wiirzburg, Germany (Received 31 January 1992) Key Word Index-Triphyophyl/um peltaturn; Dioncophyllaceae; leaves; (± )-dioncophyllacine A; naphthylisoquino­ line alkaloids; biaryls, naturally occurring; structure elucidation. Abstract-The isolation and structure elucidation of rac-dioncophyllacine A from the leaves of Triphyophyllwn peltatum, is described. Unlike all other naphthylisoquinoline alkaloids, this fully dehydrogenated representative has an additional methoxy group at C-4, the position of which is deduced from NOE results. Dioncophyllacine A has a 7,1'­ site of the biaryl axis, as in dioncophylline A. Its constitution is confirmed by an X-ray structure analysis, which shows that the crystalline form of this new alkaloid is racemic. INTRODUCTION RESULTS AND DISCUSSION The genus Triphyophyllum with its only species The leaves of T. peltatum were extracted with di­ T. peltatum Airy Shaw belongs to the family of the chloromethane. The early fractions obtained on CC of the Dioncophyllaceae, a very small group of African medi­ extract yielded a nitrogen-containing crystalline solid cinal plants [2], the taxonomical position of which in the (130 mg).
    [Show full text]
  • Ancistrocladaceae
    Soltis et al—American Journal of Botany 98(4):704-730. 2011. – Data Supplement S2 – page 1 Soltis, Douglas E., Stephen A. Smith, Nico Cellinese, Kenneth J. Wurdack, David C. Tank, Samuel F. Brockington, Nancy F. Refulio-Rodriguez, Jay B. Walker, Michael J. Moore, Barbara S. Carlsward, Charles D. Bell, Maribeth Latvis, Sunny Crawley, Chelsea Black, Diaga Diouf, Zhenxiang Xi, Catherine A. Rushworth, Matthew A. Gitzendanner, Kenneth J. Sytsma, Yin-Long Qiu, Khidir W. Hilu, Charles C. Davis, Michael J. Sanderson, Reed S. Beaman, Richard G. Olmstead, Walter S. Judd, Michael J. Donoghue, and Pamela S. Soltis. Angiosperm phylogeny: 17 genes, 640 taxa. American Journal of Botany 98(4): 704-730. Appendix S2. The maximum likelihood majority-rule consensus from the 17-gene analysis shown as a phylogram with mtDNA included for Polyosma. Names of the orders and families follow APG III (2009); other names follow Cantino et al. (2007). Numbers above branches are bootstrap percentages. 67 Acalypha Spathiostemon 100 Ricinus 97 100 Dalechampia Lasiocroton 100 100 Conceveiba Homalanthus 96 Hura Euphorbia 88 Pimelodendron 100 Trigonostemon Euphorbiaceae Codiaeum (incl. Peraceae) 100 Croton Hevea Manihot 10083 Moultonianthus Suregada 98 81 Tetrorchidium Omphalea 100 Endospermum Neoscortechinia 100 98 Pera Clutia Pogonophora 99 Cespedesia Sauvagesia 99 Luxemburgia Ochna Ochnaceae 100 100 53 Quiina Touroulia Medusagyne Caryocar Caryocaraceae 100 Chrysobalanus 100 Atuna Chrysobalananaceae 100 100 Licania Hirtella 100 Euphronia Euphroniaceae 100 Dichapetalum 100
    [Show full text]
  • Carnivorous Plants with Hybrid Trapping Strategies
    CARNIVOROUS PLANTS WITH HYBRID TRAPPING STRATEGIES BARRY RICE • P.O. Box 72741 • Davis, CA 95617 • USA • [email protected] Keywords: carnivory: Darlingtonia californica, Drosophyllum lusitanicum, Nepenthes ampullaria, N. inermis, Sarracenia psittacina. Recently I wrote a general book on carnivorous plants, and while creating that work I spent a great deal of time pondering some of the bigger issues within the phenomenon of carnivory in plants. One of the basic decisions I had to make was select what plants to include in my book. Even at the genus level, it is not at all trivial to produce a definitive list of all the carnivorous plants. Seventeen plant genera are commonly accused of being carnivorous, but not everyone agrees on their dietary classifications—arguments about the status of Roridula can result in fistfights!1 Recent discoveries within the indisputably carnivorous genera are adding to this quandary. Nepenthes lowii might function to capture excrement from birds (Clarke 1997), and Nepenthes ampullaria might be at least partly vegetarian in using its clusters of ground pitchers to capture the dead vegetable mate- rial that rains onto the forest floor (Moran et al. 2003). There is also research that suggests that the primary function of Utricularia purpurea bladders may be unrelated to carnivory (Richards 2001). Could it be that not all Drosera, Nepenthes, Sarracenia, or Utricularia are carnivorous? Meanwhile, should we take a closer look at Stylidium, Dipsacus, and others? What, really, are the carnivorous plants? Part of this problem comes from the very foundation of how we think of carnivorous plants. When drafting introductory papers or book chapters, we usually frequently oversimplify the strategies that carnivorous plants use to capture prey.
    [Show full text]
  • Abstract an Examination of Possible Carnivory in Silene
    ABSTRACT AN EXAMINATION OF POSSIBLE CARNIVORY IN SILENE REGIA, A MEMBER OF THE CARYOPHYLLACEAE by Garrett John Dienno Silene regia, commonly known as Royal Catchfly, a member of the Caryophyllaceae, is known to ensnare small insects with its glandular trichomes. This morphological adaptation is primarily thought to deter herbivory, but it has been speculated that S. regia may also be carnivorous. To demonstrate that S. regia is carnivorous the following objectives must be shown: S. regia can attract, capture, and retain prey; secrete proteinases to facilitate nutrient absorption; and absorb/translocate the resultant nutrients. This study addressed the first two of these objectives through field observations, UV photography, SEM imaging, and a series of experiments designed to examine a capture- induced proteinase response. While S. regia was able to ensnare insects and possessed highly specialized morphological structures for doing so a form of active attractant could not be demonstrated, and as such failed to support the first objective in its entirety. Negative test results for a capture-induced proteinase response failed to support the second objective. As both objectives were unsupported it was concluded that S. regia is not carnivorous. AN EXAMINATION OF POSSIBLE CARNIVORY IN SILENE REGIA, A MEMBER OF THE CARYOHPYLLACEAE A Thesis Submitted to the Faculty of Miami University in partial fulfillment of the requirements for the degree of Master of Science by Garrett John Dienno Miami University Oxford, Ohio 2017 Advisor: R. James Hickey Reader: Alfredo J. Huerta Reader: Richard C. Moore Reader: Richard H. Munson ©2017 Garrett John Dienno This thesis titled AN EXAMINATION OF POSSIBLE CARNIVORY IN SILENE REGIA, A MEMBER OF THE CARYOHPYLLACEAE by Garrett John Dienno has been approved for publication by The College of Arts and Science and Department of Biology ____________________________________________________ R.
    [Show full text]
  • Universidade Estadual Paulista Câmpus De
    Campus de Botucatu UNESP - UNIVERSIDADE ESTADUAL PAULISTA CÂMPUS DE BOTUCATU INSTITUTO DE BIOCIÊNCIAS GENÔMICA ORGANELAR E EVOLUÇÃO DE GENLISEA E UTRICULARIA (LENTIBULARIACEAE) SAURA RODRIGUES DA SILVA Tese apresentada ao Instituto de Biociências, Câmpus de Botucatu, UNESP, para obtenção do título de Doutor em Ciências Biológicas (Botânica) BOTUCATU - SP - 2018 - 1 Instituto de Biociências – Departamento de Botânica Distrito de Rubião Júnior s/n CEP 18618-000 Botucatu SP Brasil Tel 14 3811 6265/6053 fax 14 3815 3744 [email protected] Campus de Botucatu UNESP - UNIVERSIDADE ESTADUAL PAULISTA CÂMPUS DE BOTUCATU INSTITUTO DE BIOCIÊNCIAS GENÔMICA ORGANELAR E EVOLUÇÃO DE GENLISEA E UTRICULARIA (LENTIBULARIACEAE) SAURA RODRIGUES DA SILVA PROF. DR. VITOR FERNANDES OLIVEIRA DE MIRANDA ORIENTADOR PROF. DR. ALESSANDRO DE MELLO VARANI Coorientador Tese apresentada ao Instituto de Biociências, Câmpus de Botucatu, UNESP, para obtenção do título de Doutor em Ciências Biológicas (Botânica) BOTUCATU - SP - 2018 - 2 Instituto de Biociências – Departamento de Botânica Distrito de Rubião Júnior s/n CEP 18618-000 Botucatu SP Brasil Tel 14 3811 6265/6053 fax 14 3815 3744 [email protected] Campus de Botucatu FICHA CATALOGRÁFICA ELABORADA PELA SEÇÃO TÉCNICA DE AQUISIÇÃO E TRATAMENTO DA INFORMAÇÃO DIVISÃO TÉCNICA DE BIBLIOTECA E DOCUMENTAÇÃO - CAMPUS DE BOTUCATU - UNESP Silva, Saura Rodrigues. Genômica organelar e evolução de Genlisea e Utricularia (Lentibulariaceae) / Saura Rodrigues da Silva. – 2018. Tese (doutorado) – Universidade Estadual Paulista, Instituto de Biociências de Botucatu, 2018. Orientador: Vitor Fernandes Oliveira de Miranda Co-orientador: Alessandro de Mello Varani Assunto CAPES: 1. Sistemática Vegetal CDD 581.1 Palavras-chave: Utricularia; Genlisea; genômica de organelas; ndhs; Evolução de organelas.
    [Show full text]
  • The Roots of Carnivorous Plants
    Plant and Soil (2005) 274:127–140 Ó Springer 2005 DOI 10.007/s11104-004-2754-2 The roots of carnivorous plants Wolfram Adlassnig1, Marianne Peroutka1, Hans Lambers2 & Irene K. Lichtscheidl1,3 1Institute of Ecology and Conservation Biology, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria. 2School of Plant Biology, Faculty of Natural and Agricultural Sciences, The University of Western Australia, Crawley WA 6009, Australia. 3Corresponding author* Received 30 April 2004. Accepted in revised form 31 August 2004 Key words: carnivorous plants, insectivorous plants, morphology, nutrition, root Abstract Carnivorous plants may benefit from animal-derived nutrients to supplement minerals from the soil. Therefore, the role and importance of their roots is a matter of debate. Aquatic carnivorous species lack roots completely, and many hygrophytic and epiphytic carnivorous species only have a weakly devel- oped root system. In xerophytes, however, large, extended and/or deep-reaching roots and sub-soil shoots develop. Roots develop also in carnivorous plants in other habitats that are hostile, due to flood- ing, salinity or heavy metal occurance. Information about the structure and functioning of roots of car- nivorous plants is limited, but this knowledge is essential for a sound understanding of the plants’ physiology and ecology. Here we compile and summarise available information on: (1) The morphology of the roots. (2) The root functions that are taken over by stems and leaves in species without roots or with poorly developed root systems; anchoring and storage occur by specialized chlorophyll-less stems; water and nutrients are taken up by the trap leaves. (3) The contribution of the roots to the nutrient supply of the plants; this varies considerably amongst the few investigated species.
    [Show full text]
  • Carnivorous Plantsplants –– Classicclassic Perspectivesperspectives Andand Newnew Researchresearch
    CarnivorousCarnivorous plantsplants –– classicclassic perspectivesperspectives andand newnew researchresearch Barry Rice The Nature Conservancy, Davis, USA The ranks of known carnivorous plants have grown to approximately 600 species. We are learning that the relationships between these feeders and their prey are more complex, and perhaps gentler, than previously suspected. Unfortunately, these extraordinary life forms are becoming extinct before we can even document them! Carnivorous plants are able to do four things: they attract, false signals, the trigger hairs must be bent, not once, but trap, digest and absorb animal life forms. While these four two or more times in rapid succession. In effect, the plant abilities may seem remarkable in combination, they are, can count! When the trap first closes, the lobes fit together individually, quite common in the plant kingdom. All very loosely, the marginal spines interweaving to form a plants that produce flowers for the purpose of summoning botanical jail. Prey items that are too small to be worth pollinators are already skilled at attracting animals. Many digesting can quickly escape, and the trap will reopen the plants trap animals at least temporarily, usually for the next day. But, large prey remain trapped, and their purposes of pollination. Digestion may seem odd, but all panicked motions continue to stimulate the trigger hairs. plants produce enzymes that have digestive capabilities – This encourages the traps to seal completely, suffocating carnivorous plants have only relocated the site of enzy- the prey, and to release digestive enzymes. (Children who matic activity to some external pitcher or leaf surface. feed dead flies to their pet Venus flytraps are often disap- Finally, absorption of nutrients is something that all pointed when, the next day, the uninterested plants open plants do (or, at least, all that survive past the cotyledon their traps and reject the inanimate morsels – only live stage).
    [Show full text]
  • Cornelissen Et Al. 2003. a Handbook of Protocols for Standardised And
    CSIRO PUBLISHING www.publish.csiro.au/journals/ajb Australian Journal of Botany, 2003, 51, 335–380 A handbook of protocols for standardised and easy measurement of plant functional traits worldwide J. H. C. CornelissenA,J, S. LavorelB, E. GarnierB, S. DíazC, N. BuchmannD, D. E. GurvichC, P. B. ReichE, H. ter SteegeF, H. D. MorganG, M. G. A. van der HeijdenA, J. G. PausasH and H. PoorterI ADepartment of Systems Ecology, Institute of Ecological Science, Faculty of Earth and Life Sciences, Vrije Universiteit, De Boelelaan 1087, 1081 HV Amsterdam, The Netherlands. BC.E.F.E.–C.N.R.S., 1919, Route de Mende, 34293 Montpellier Cedex 5, France. CInstituto Multidisciplinario de Biología Vegetal, F.C.E.F.yN., Universidad Nacional de Córdoba - CONICET, CC 495, 5000 Córdoba, Argentina. DMax-Planck-Institute for Biogeochemistry, PO Box 10 01 64, 07701 Jena, Germany; current address: Institute of Plant Sciences, Universitätstrasse 2, ETH Zentrum LFW C56, CH-8092 Zürich, Switzerland. EDepartment of Forest Resources, University of Minnesota, 1530 N. Cleveland Ave., St Paul, MN 55108, USA. FNational Herbarium of the Netherlands NHN, Utrecht University branch, Plant Systematics, PO Box 80102, 3508 TC Utrecht, The Netherlands. GDepartment of Biological Sciences, Macquarie University, Sydney, NSW 2109, Australia. HCentro de Estudios Ambientales del Mediterraneo (CEAM), C/ C.R. Darwin 14, Parc Tecnologic, 46980 Paterna, Valencia, Spain. IPlant Ecophysiology Research Group, Faculty of Biology, Utrecht University, PO Box 800.84, 3508 TB Utrecht, The Netherlands. JCorresponding author; email: [email protected] Contents Abstract. 336 Physical strength of leaves . 350 Introduction and discussion . 336 Leaf lifespan.
    [Show full text]
  • From Flypaper to Pitfall Traps: Function and Evolution of Trapping Fluids
    From flypaper to pitfall traps: function and evolution of trapping fluids Supervisors: Dr Carmen Galan (School of Chemistry, University of Bristol) – Main supervisor Dr Heather Whitney (School of Biological Sciences, University of Bristol) Dr Ulrike Bauer (School of Biological Sciences, University of Bristol) Dr Monica Berry (NSQI, University of Bristol) Host institution: University of Bristol Project descriptor: Importance: The traps of carnivorous plants are examples of drastic structural and functional modifications of plant organs and provide a unique opportunity to study evolution. Pitcher leaves are thought to have evolved from simpler flypaper leaves on several independent occasions. Spontaneous mutations can cause the formation of epiascidiate (tubular) leaves in various non- carnivorous plants, e.g. in Codiaeum variegatum or Ficus benghalensis. Virtually nothing is known about the detailed function or the evolution of the trapping fluid, a key component of both flypaper and pitcher traps and milestone invention on the evolutionary road to plant carnivory. Aims: This project investigates the properties and function of the trap fluids in a group of closely related flypaper and pitcher plants, comprising the sundews (Drosera and Drosophyllum), pitcher plants (Nepenthes) and a carnivorous liana (Triphyophyllum). All these employ polysaccharide-based secretions to aid in the trapping, retention and killing of insects, but the composition and rheology of these fluids remains largely unknown. Chemical analyses of the sticky mucilage of Drosera capensis and Drosophyllum lusitanicum (overview in Juniper et. al 1989) indicate small differences in the polysaccharide composition. Gaume et al. (2007) investigated the rheology of Nepenthes rafflesiana pitcher fluid and reported a highly viscoelastic behaviour which plays a key role in trapping.
    [Show full text]
  • Micropropagation of Carnivorous Plants
    University of Rhode Island DigitalCommons@URI Open Access Dissertations 2003 Micropropagation of Carnivorous Plants Kenneth Stephen Uhnak University of Rhode Island Follow this and additional works at: https://digitalcommons.uri.edu/oa_diss Recommended Citation Uhnak, Kenneth Stephen, "Micropropagation of Carnivorous Plants" (2003). Open Access Dissertations. Paper 471. https://digitalcommons.uri.edu/oa_diss/471 This Dissertation is brought to you for free and open access by DigitalCommons@URI. It has been accepted for inclusion in Open Access Dissertations by an authorized administrator of DigitalCommons@URI. For more information, please contact [email protected]. MICROPROPAGATION OF CARNIVOROUS PLANTS BY KENNETH STEPHEN UHNAK A DISSERTATION IN PARTIAL FULFILLMENT OF THE REQUIREMENT FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN BIOLOGICAL SCIENCES • UNIVERSITY OF RHODE ISLAND 2003 DOCTOR OF PHILOSOPHY DISSERTATION OF KENNETH S. UHNAK APPROVED: Dissertation Committee Major Pro fes so r_ ___,#"=<f----'--:;_:__;;~----l'-----''---"'--'-------,-..,.._- UNIVERSITY OF RHODE ISLAND 2003 ABSTRACT A simple, efficient system for seed surface disinfestation and in vitro germination was developed for the carnivorous pitcher plants Darlingtonia californica and Sarracenia leucophylla. Of the disinfectants tested, hydrogen peroxide or 10% Clorox® were most effective for disinfesting seeds of D. californica, while concentrated sulfuric acid worked best for S. leucophylla. Differences in the effectiveness of sterilants were associated by differences in seed coat morphology. Seeds of D. californica imbibed at 4-7°C in sterile deionized water with surfactant and gibberellin germinated earlier than seeds without exposure to gibberellin. Unimbibed seeds of S. leucophylla germinated rapidly in sterile water after treatment in concentrated sulfuric acid. Scanning electron microscopy of D.
    [Show full text]
  • What Exactly Is a Carnivorous Plant?
    7HFKQLFDO5HIHUHHG&RQWULEXWLRQ What exactly is a carnivorous plant? Barry A. Rice • Center for Plant Diversity • University of California • One Shields Avenue • Davis, California 95616 • USA • [email protected] We all find carnivorous plants fascinating, beautiful, and interesting. But just what is a carnivo- rous plant? What are the attributes that transform a mundane vegetable into a hungry killer? For a long time I preached that a plant is carnivorous if it attracts, captures, digests, and absorbs prey. This four-point definition seemed to work. In 2009 I was asked to write a scientific review of carnivorous plants for a technical volume (Rice 2010). I used this opportunity to review prior definitions of carnivory in plants. The first carefully stated definition I could find had two parts: (1) a plant must have at least one adaptation for attraction, capture, or digestion of prey, and (2) that the plant must be able to absorb the nutrients from the prey (Givnish et al. 1984). Juniper et al. (1989) also offered a definition with two criteria—the possession of both traps and digestive organs. To the common four-point definition (attract, capture, digest, and absorb), Schnell (2002) added that a carnivorous plant must clearly benefit from the obtained nutrients. Why is it so difficult to easily define what we mean by carnivorous plants? The problem is rooted in two underlying issues: paracarnivory, and hunting inefficiency. Paracarnivorous Plants Paracarnivorous plants are those that have some, but not all, of the characteristics of a carnivo- rous plant. The situation is exemplified by the two species in the genus Roridula (Anderson 2005; Anderson & Midgley 2002).
    [Show full text]