4, Mohammed Nour 1 and Phila Raharivelomanana 5,*

Total Page:16

File Type:pdf, Size:1020Kb

4, Mohammed Nour 1 and Phila Raharivelomanana 5,* molecules Article Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily Benjamin Métoyer 1, Nicolas Lebouvier 1, Edouard Hnawia 1, Gaëtan Herbette 2 ID , Louis Thouvenot 3, Yoshinori Asakawa 4, Mohammed Nour 1 and Phila Raharivelomanana 5,* 1 Institut des Sciences Exactes et Appliquées (ISEA) EA 7484, Université de la Nouvelle-Calédonie, 98851 Nouméa, New Caledonia; [email protected] (B.M.); [email protected] (N.L.); [email protected] (E.H.); [email protected] (M.N.) 2 Aix Marseille Univ, CNRS, Centrale Marseille, FSCM, Spectropole, Service 511, Campus Saint-Jérome, 13397 Marseille CEDEX 20, France; [email protected] 3 Independent Researcher, 11, Rue Saint-Léon, 66000 Perpignan, France; [email protected] 4 Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 7708514, Japan; [email protected] 5 UMR 241 EIO, Université de la Polynésie Française, 98702 Faaa, Tahiti, French Polynesia * Correspondence: [email protected] Received: 21 May 2018; Accepted: 31 May 2018; Published: 5 June 2018 Abstract: Volatile components of seven species of the Bazzanioideae sub-family (Lepidoziaceae) native to New Caledonia, including three endemic species (Bazzania marginata, Acromastigum caledonicum and A. tenax), were analyzed by GC-FID-MS in order to index these plants to known or new chemotypes. Detected volatile constituents in studied species were constituted mainly by sesquiterpene, as well as diterpene compounds. All so-established compositions cannot successfully index some of them to known chemotypes but afforded the discovery of new chemotypes such as cuparane/fusicoccane. The major component of B. francana was isolated and characterized as a new zierane-type sesquiterpene called ziera-12(13),10(14)-dien-5-ol (23). In addition, qualitative intraspecies variations of chemical composition were very important particularly for B. francana which possessed three clearly defined different compositions. We report here also the first phytochemical investigation of Acromastigum species. Moreover, crude diethyl ether extract of B. vitatta afforded a new bis(bibenzyl) called vittatin (51), for which a putative biosynthesis was suggested. Keywords: liverwort; Bazzania; Acromastigum; sesquiterpene; diterpene; bis(bibenzyl); biosynthesis; zierane; vittatin 1. Introduction Liverworts are part of Bryoflora (mosses: 14,000 species, liverworts: 6000 species and hornworts: 300 species), considered as the first terrestrial plants and taxonomically indexed between algae and pteridophytes. Bryophytes possess archaic characteristics such as the absence of seeds and vascularized leaves [1]. Morphological traits such as small size of organs or relatively simple structure or high intraspecies variability and fugacity of some microscopic details (which may disappear within the plant dryness such as oil bodies), add difficulties for liverwort’s taxonomic identification. Nevertheless, many liverworts have unique organelles called oil bodies in their cells which are linked to the biosynthesis of original secondary metabolites such as mono-, sesqui- and diterpenes or phenolic compounds that could be cladistic biomarker. Most of liverwort’s sesquiterpenes are enantiomers of those found in higher plants [2]. Molecules 2018, 23, 1353; doi:10.3390/molecules23061353 www.mdpi.com/journal/molecules MoleculesMolecules 20182018,, 2323,, 1353x 2 of 27 2 of 27 New Caledonia is an archipelago of 18,600 km2 located in South Pacific region and considered as a Newhotspot Caledonia of biodiversity is an archipelago [3]. In New of Caledonia, 18,600 km2 482located species in South and infraspecific Pacific region taxa and of considered liverworts ashave a hotspot been described of biodiversity in a recent [3]. Inchecklist New Caledonia, [4]. The rate 482 of species endemism and is infraspecific comprised taxabetween of liverworts 13% and have39% that been makes described New in Caledonia a recent checklist as one of [4 ].the The richest rate of liverwort endemism areas is comprised in the world, between together 13% with and 39%Japan, that New makes Zealand, New Caledoniaand Costa asRica one [5]. of the richest liverwort areas in the world, together with Japan, NewBazzanioideae Zealand, and Costa is a Ricasubfamily [5]. of the Lepidoziaceae family including three genera Bazzania, AcromaBazzanioideaestigum and Mastigopelma is a subfamily, this of latter the Lepidoziaceaeone had never familybeen inventoried including threein New genera CaledoniaBazzania [4],. AcromastigumThrough the world,and Mastigopelma nearly 280 ,Bazzania this latter species one had and never 40 Acromastigum been inventoried species in are New described Caledonia [6]. [ 4In]. ThroughNew Caledonia, the world, 20 nearlyBazzania 280 speciesBazzania or speciesvarieties and including 40 Acromastigum 12 endemicsspecies and are 16 describedAcromastigum [6]. Inspecies New Caledonia,or varieties 20includingBazzania 10species endemics or varieties have been including described 12 endemics[4]. Usually, and Bazzania 16 Acromastigum species arespecies divided or varietiesinto two includingchemotypes 10: endemics albicanyl(drimenyl) have been described-caffeate-cuparane [4]. Usually, (I) Bazzaniaand calamenanespecies are(II) divided [7]. into two chemotypes:Volatile albicanyl(drimenyl)-caffeate-cuparanecompounds of 27 specimens belonging (I)and to seven calamenane different (II) [species,7]. including three endemicsVolatile (marked compounds with an of 27asterisk) specimens were belonging investigated to seven in order different to check species, intra including- and inter three-variability endemics of (markedmolecular with contents. an asterisk) Studied were Bazzanioideae investigated inspecies order belong to check to intra- the following and inter-variability genera: Acromastigum of molecular contents.(A. tenax*, Studied A. caledonicum Bazzanioideae*) and Bazzania species ( belongB. parisii to, B. the marginata following*, B. genera: vittata, AcromastigumB. francana, B. bernieri (A. tenax and*, A.B. caledonicumserrifolia). B.*) serrifolia and Bazzania is a synonym (B. parisii of, B. B. marginata bernieri according*, B. vittata ,toB. Kitagawa francana, B.(1973) bernieri [8] andbut B.we serrifolia studied). B.here serrifolia its putativeis a synonym specific status of B. by bernieri separatingaccording the samples to Kitagawa in two (1973) lots of [8 ]specimens but we studied on the herebasis itsof putativetheir morphological specific status traits. by separating the samples in two lots of specimens on the basis of their morphologicalVolatile components traits. of diethyl ether extracts were analyzed by GC-MS-FID in order to index theseVolatile plants componentsinto knownof Bazzania diethyl etherchemotypes. extracts wereIn the analyzed present bywork, GC-MS-FID two new in ordermolecules: to index an theseoxygenated plants intodimer known of Bazzanialunularicchemotypes. acid (51) and In the an present alcohol work, zierane two new-type molecules: sesquiterpene an oxygenated (23) are dimercharacterized of lunularic for the acid first (51 time) and (Tables an alcohol 1 and zierane-type 2). They were sesquiterpene respectively (23 isolated) are characterized from diethyl for ether the firstextract time of (Tables B. vittata1 and and2). TheyB. francana were respectively. To our best isolated knowledge from diethyl, this etheris the extract first ofphytochemicalB. vittata and B.investigation francana. To ourof all best these knowledge, species this and is thethe first first phytochemical chemical analysis investigation of those of all belonging these species to andthe theAcromastigum first chemical genus. analysis of those belonging to the Acromastigum genus. InIn orderorder toto sortsort thethe detected volatile compounds in this study, diterpene-typediterpene-type contentscontents areare listedlisted (Table(Table 33),), listedlisted sesquiterpenesesquiterpene moleculesmolecules werewere classifiedclassified followingfollowing theirtheir firstfirst cyclizationcyclization precursorsprecursors (Figure(Figure1 1),), and and their their sesquiterpene sesquiterpene types types (Tables (Table4–6)s related4–6) related to the correspondingto the corresponding biosynthesis biosynthesis pathway schemepathway from scheme the literature from the data literature [9–19]. data So, compilation [9–19]. So, ofcompilation chemical composition of chemical of composition all studied species of all arestudied gathered species in Tableare gathered7. List of in identified Table 7. andList unknownof identified compounds and unknown is shown compounds in Tables is8 –shown10. Most in importantTables 8–10. detected Most important compounds detected for chemotaxonomy compounds for are chemotaxonomy shown in Figure are2. shown in Figure 2. 14 5 8 7 4 ionization isomerization 6 + 9 3 H C 10 2 2 15 11 + 12 1 CH2 13 OPP Farnesyl diphosphate Farnesyl Nerolidyl RC1 10,1 RC1 11,1 RC1 6,1 RC1 10,1 RC1 11,1 + C + + + C CH CH + C (E-E)-Germacradienyl (E-E)-Humulyl Bisabolyl (Z-E)-Germacradienyl (Z-E)-Humulyl FigureFigure 1. SchemeScheme of ofcationic cationic first first cyclizat cyclizationion precursor precursor for the for detected the detected sesquiterpenes sesquiterpenes (1 ring closure) (1 ring closure)[19]. [19]. Molecules 2018, 23, 1353 3 of 27 Molecules 2018, 23, x 3 of 27 OH HO 1 2 3 4 5 6 7 OH 8 9 10 11 12 13 H H 14 15 16 17 18 H H HO H HO OH H H HO 19 20 21 22 23 H H O 24 25 26 27 28 29 H H HO OH H H H H 30 31 32 33 34 35 36 OH OH OH
Recommended publications
  • University of Cape Town
    The copyright of this thesis rests with the University of Cape Town. No quotation from it or information derived from it is to be published without full acknowledgement of the source. The thesis is to be used for private study or non-commercial research purposes only. University of Cape Town Addendum (1) Soon after submitting this thesis a more recent comprehensive classification by Crandall-Stotler et al. (2009)1 was published. This recent publication does not undermine the information presented in this thesis. The purpose of including the comprehensive classification of Crandall-Stotler and Stotler (2000) was specifically to introduce some of the issues regarding the troublesome classification of this group of plants. Crandall-Stotler and Stotler (2000), Grolle and Long (2000) for Europe and Macaronesia and Schuster (2002) for Austral Hepaticae represent three previously widely used yet differing opinions regarding Lophoziaceae classification. They thus reflect a useful account of some of the motivation for initiating this project in the first place. (2) Concurrently or soon after chapter 2 was published by de Roo et al. (2007)2 more recent relevant papers were published. These include Heinrichs et al. (2007) already referred to in chapter 4, and notably Vilnet et al. (2008)3 examining the phylogeny and systematics of the genus Lophozia s. str. The plethora of new information regarding taxa included in this thesis is encouraging and with each new publication we gain insight and a clearer understanding these fascinating little plants. University of Cape Town 1 Crandall-Stotler, B., Stotler, R.E., Long, D.G. 2009. Phylogeny and classification of the Marchantiophyta.
    [Show full text]
  • Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily
    molecules Article Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily Benjamin Métoyer 1, Nicolas Lebouvier 1, Edouard Hnawia 1, Gaëtan Herbette 2 ID , Louis Thouvenot 3, Yoshinori Asakawa 4, Mohammed Nour 1 and Phila Raharivelomanana 5,* 1 Institut des Sciences Exactes et Appliquées (ISEA) EA 7484, Université de la Nouvelle-Calédonie, 98851 Nouméa, New Caledonia; [email protected] (B.M.); [email protected] (N.L.); [email protected] (E.H.); [email protected] (M.N.) 2 Aix Marseille Univ, CNRS, Centrale Marseille, FSCM, Spectropole, Service 511, Campus Saint-Jérome, 13397 Marseille CEDEX 20, France; [email protected] 3 Independent Researcher, 11, Rue Saint-Léon, 66000 Perpignan, France; [email protected] 4 Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 7708514, Japan; [email protected] 5 UMR 241 EIO, Université de la Polynésie Française, 98702 Faaa, Tahiti, French Polynesia * Correspondence: [email protected] Received: 21 May 2018; Accepted: 31 May 2018; Published: 5 June 2018 Abstract: Volatile components of seven species of the Bazzanioideae sub-family (Lepidoziaceae) native to New Caledonia, including three endemic species (Bazzania marginata, Acromastigum caledonicum and A. tenax), were analyzed by GC-FID-MS in order to index these plants to known or new chemotypes. Detected volatile constituents in studied species were constituted mainly by sesquiterpene, as well as diterpene compounds. All so-established compositions cannot successfully index some of them to known chemotypes but afforded the discovery of new chemotypes such as cuparane/fusicoccane. The major component of B.
    [Show full text]
  • Molecular Insights Into the Phylogeny of the Leafy Liverwort Family Lophoziaceae Cavers
    TAXON 56 (2) • May 2007: 301–314 De Roo & al. • Molecular phylogeny of Lophoziaceae MOLECULAR PHYLOGENETICS Molecular insights into the phylogeny of the leafy liverwort family Lophoziaceae Cavers Ryan Thomas de Roo1, Terry A. Hedderson1 & Lars Söderström2 1 Bolus Herbarium, Department of Botany, University of Cape Town, Private Bag, Rondebosch 7701, South Africa. [email protected] (author of correspondence) 2 Department of Biology, Norwegian University of Science and Technology, 7491 Trondheim, Norway Delimitation and classification of the large, cosmopolitan liverwort family Lophoziaceae is controversial. Many recent workers have included it in Jungermanniaceae, and even in its strictest sense, internal classifica- tion has varied widely among different treatments. We analyse variation in DNA sequences of the chloroplast rps4 gene and the trnG intron to provide resolution of phylogenetic relationships in the leafy liverworts with emphasis on the various elements usually placed in Lophoziaceae. The following conclusions are drawn. Lophoziaceae is not closely related to Jungermanniaceae. Lophoziaceae, and perhaps also Cephaloziellaceae, should be included in Scapaniaceae unless many small families are recognised. Delavayella and Blepharido- phyllum are excluded from Scapaniaceae. Jamesonielloideae is a family of its own (Jamesoniellaceae) sister to Adelanthaceae (or a subfamily of Adelanthaceae). The genus Anastrophyllum should be split into Anastrophyl- lum and Sphenolobus. Lophozia is polyphyletic and the genera Isopaches and Schistochilopsis, and perhaps Obtusifolium, should be recognised while L. sudetica could be transferred to Barbilophozia. Barbilophozia s.str. is monophyletic while Orthocaulis is polyphyletic with the four sampled species appearing in 3 different clades; their relationships are poorly resolved. Lophozia silvicola Buch is clearly separated from L.
    [Show full text]
  • Chemotypes and Biomarkers of Seven Species of New Caledonian
    Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily Benjamin Métoyer, Nicolas Lebouvier, Edouard Hnawia, Gaëtan Herbette, Louis Thouvenot, Yoshinori Asakawa, Mohammed Nour, Phila Raharivelomanana To cite this version: Benjamin Métoyer, Nicolas Lebouvier, Edouard Hnawia, Gaëtan Herbette, Louis Thouvenot, et al.. Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily. Molecules, MDPI, 2018, 23 (6), 27 p. 10.3390/molecules23061353. hal-02146432 HAL Id: hal-02146432 https://hal.archives-ouvertes.fr/hal-02146432 Submitted on 3 Jun 2019 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. molecules Article Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily Benjamin Métoyer 1, Nicolas Lebouvier 1, Edouard Hnawia 1, Gaëtan Herbette 2 ID , Louis Thouvenot 3, Yoshinori Asakawa 4, Mohammed Nour 1 and Phila Raharivelomanana 5,* 1 Institut des Sciences Exactes et Appliquées (ISEA) EA 7484, Université de la Nouvelle-Calédonie,
    [Show full text]
  • Jubulaceae, Marchantiophyta)
    A peer-reviewed open-access journal PhytoKeys 50: 101–122The resurrection(2015) of Neohattoria Kamim. (Jubulaceae, Marchantiophyta)... 101 doi: 10.3897/phytokeys.50.4940 RESEARCH ARTICLE http://phytokeys.pensoft.net Launched to accelerate biodiversity research The resurrection of Neohattoria Kamim. (Jubulaceae, Marchantiophyta): a six decade systematic conflict resolved through a molecular perspective Juan Larraín1, Benjamin Carter2, Blanka Shaw2, Jörn Hentschel3, Lynika S. Strozier1, Tatsuwo Furuki4, Jochen Heinrichs5, Barbara Crandall-Stotler6, John Engel1, Matt von Konrat1 1 Science & Education, The Field Museum, 1400 South Lake Shore Drive, Chicago, IL 60605-2496, U.S.A. 2 Department of Biology, Duke University, Durham, NC 27708-0338, U.S.A. 3 Department of Systematic Botany with Herbarium Haussknecht and Botanical Garden, Friedrich Schiller University, Fürstengraben 1, 07743 Jena, Germany 4 Natural History Museum & Institute, 955-2 Aoba-cho, Chuo-ku, Chiba-shi, Chiba 260-8682, Japan 5 Ludwig-Maximilians-Universität München, Department für Biologie I, Systematische Botanik und Mykologie, GeoBio-Center, Menzinger Straße 67, 80638 München, Germany 6 Southern Illinois University, Department of Plant Biology, Mail Code 6509, wCarbondale IL 62901-6509, U.S.A. Corresponding author: Juan Larraín ([email protected]) Academic editor: E. Cooper | Received 20 March 2015 | Accepted 16 April 2015 | Published 16 June 2015 Citation: Larraín J, Carter B, Shaw B, Hentschel J, Strozier LS, Furuki T, Heinrichs J, Crandall-Stotler B, Engel J, von Konrat M (2015) The resurrection ofNeohattoria Kamim. (Jubulaceae, Marchantiophyta): a six decade systematic conflict resolved through a molecular perspective. PhytoKeys 50: 101–122. doi: 10.3897/phytokeys.50.4940 Abstract The systematic placement ofFrullania herzogii has been contentious since its description six decades ago.
    [Show full text]
  • Checklist of the Bryophytes of Tamil Nadu, India 1
    Checklist of the bryophytes of Tamil Nadu, India 1 Checklist of the bryophytes of Tamil Nadu, India A. E. D. Daniels Botany Department, Scott Christian College, Nagercoil - 629 003, Tamil Nadu, India Abstract: The checklist reports 712 taxa of bryophytes from Tamil Nadu, India, comprising 211 taxa in 56 genera and 32 families of liverworts, 8 taxa in 4 genera and 2 families of hornworts, and 493 taxa in 189 genera and 44 families of mosses. Literature sources for Tamil Nadu records are included for each taxon, and an extensive synonymy is provided. For currently accepted taxa, the details of types from Tamil Nadu are indicated. A map of Tamil Nadu, a synopsis of families and genera, and a bibliography are provided. INTRODUCTION India is one of the 12 megabiodiversity countries in the world (Nayar, 1996). The large area and the variety of phytoclimatic conditions met within its different biogeographical zones contribute to the great diversity of the Indian flora (Singh, 1997; 2001). These biogeographical zones, with diverse topographical variations and climatic conditions, have been divided into seven bryogeographical regions. They are (1) Western Himalayas, (2) Eastern Himalayas, (3) Punjab and West Rajasthan, (4) Gangetic Plains, (5) Central India, (6) Western and Eastern Ghats and (7) Deccan Plateau (Pandé 1958). Recently, Andaman and Nicobar Islands in the Bay of Bengal have been proposed as the eighth region to be included (Singh & Semwal, 1995). Currently, about 2480 taxa of bryophytes (including infraspecific taxa) are reported from India (including island groups, and Sikkim), comprising about 722 taxa of liverworts in 128 genera and 52 families, 36 taxa in 6 genera and 2 families of hornworts (M.J.Wigginton database) and about 1623 taxa in 342 genera and 57 families of mosses (Lal, 2005).
    [Show full text]