DOCSLIB.ORG

Isolation, Structure Determination, and Biosynthetic Studies of Secondary Metabolites from Dorid Nudlbranchs

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Isolation, Structure Determination, and Biosynthetic Studies of Secondary Metabolites from Dorid Nudlbranchs ISOLATION, STRUCTURE DETERMINATION, AND BIOSYNTHETIC STUDIES OF SECONDARY METABOLITES FROM DORID NUDLBRANCHS by EDMUND IDRIS GRAZIANI B.Sc, Trinity College, University of Toronto, 1991 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY in THE FACULTY OF GRADUATE STUDIES (Department of Chemistry) We accept this thesis as conforming to the required standard THE UNIVERSITY OF BRITISH COLUMBIA July 1996 © Edmund I. Graziani 1996 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the head of my department or by his or her representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department The University of British Columbia Vancouver, Canada DE-6 (2/88) ABSTRACT Investigations of the skin extracts from a number of dorid nudibranchs have led to the isolation of two novel compounds, lovenone (2) and limaciamine (8). Lovenone (2), isolated from the North Sea dorid Adalaria loveni, represents the first triterpenoid isolated from a nudibranch, and is only the second triterpenoid ever isolated from a marine mollusc. The structure of lovenone (2) was solved using a number of two-dimensional NMR techniques. Similarly, the isolation of limaciamine (8) from the North Sea dorid Limacia clavigera, represents the only naturally occurring analogue reported to date of triophamine (9). Triophamine (9) was originally isolated from the British Columbia dorids, Triopha catalinae and Polycera tricolor. (2) (9) The isolation and structure determination of these novel compounds led directly to an investigation into the biosynthesis of secondary metabolites by dorid nudibranchs. By taking advantage of the unique biology of dorid nudibranchs, a protocol has been developed whereby 13 multiple injections over time of [1,2- C2] acetate has afforded irrefutable proof for de novo biosynthesis in a number of dorid nudibranchs. Terpenoic acid glycerides have been isolated from skin extracts of a number of dorid nudibranchs collected worldwide. Herein is reported the first unambiguous proof for the de novo synthesis of terpenoic acid glycerides 28 and 29, isolated from Archidoris odhneri and A. 13 13 montereyensis, respectively, by NMR analysis of C- C coupling arising from incorporation of intact doubly labeled acetate. Stable isotope incorporation studies with [1,2-^C2] acetate have been used to investigate the biosynthesis of the sesquiterpenoids nanaimoal (38), acanthodoral (39), and isoacanthodoral (40) by the dorid nudibranch Acanthodoris nanaimoensis. The results have shown that: i) the sesquiterpenoids are synthesized de novo by A. nanaimoensis and ii) that a previously proposed biogenetic pathway to the isoacanthodoral skeleton was not tenable and required modification. The use of stable isotope methodology has been extended to probe polyketide biosynthesis by the dorid nudibranch, Triopha catalinae. Incorporation of [ 1,2-* ^C2]acetate into triophamine (9) has clearly shown the biogenesis of (9) from two units of butyrate and one unit of acetate. This work represents the first experimental evidence for de novo polyketide biosynthesis by a dorid nudibranch; moreover, the use of doubly-labeled [1,2-13C2] acetate has provided clear evidence in support of one pathway where a number of biosynthetic pathways were possible. iv TABLE OF CONTENTS Page Abstract ii Table of Contents iv List of Tables vi List of Figures vii List of Schemes " x List of Abbreviations xi Acknowledgments xiii Dedication xiv I. General Introduction 1 LA. Introduction to Marine Natural Products 1 I.B. Introduction to Dorid Nudibranchs and Their Secondary Metabolism 3 I.C. Research Summary 6 I. D. Endnotes: Chapter I: General Introduction 6 II. Isolation and Structure Determination of Lovenone, A Cytotoxic Degraded Triterpenoid from the North Sea Dorid Nudibranch, Adalaria loveni 8 II. A. Taxonomy 9 II.B. Collection and Isolation 10 II.C. Structure Determination 10 U.D. Biological Activity 37 II. E. Origin and Proposed Biogenesis 37 H.F. Endnotes: Chapter II: A. loveni 40 III. Isolation and Structure Determination of Limaciamine, A Diacylguanidine from the North Sea Dorid Nudibranch, Limacia clavigera 41 m.A. Taxonomy 42 III. B. Collection and Isolation 43 ITJ.C. Structure Determination 52 m.D. Endnotes: Chapter ITJ: Limacia clavigera 56 v IV. Biosynthetic Studies of Isoprenoid Secondary Metabolites from Dorid Nudibranchs Using Stable Isotopes 57 IV.I.A. Introduction 57 IV.I.B. Biosynthetic Studies with Marine Invertebrates: Practical Considerations 59 IV.I.C. Introduction to Isoprenoid Biosynthesis 63 rV.I.D. Previous Studies into the Biosynthesis of Terpenoids by Marine Invertebrates 67 IV.II. Biosynthesis of Terpenoic Acid Glycerides by the Dorid Nudibranchs Archidoris odhneri and A. montereyensis 75 IV.II.A. Preamble 76 IV.II.B. Preliminary Results Using Liposomes 78 IV. II.C. Successful Incorporation Studies 82 IV.III. Stable Isotope Incorporation Studies on Sesquiterpenoids from the Dorid Nudibranch Acanthodoris nanaimoensis 99 IV. IV. Endnotes: Chapter IV: Biosynthesis of Isoprenoids 130 V. Stable Isotope Investigations on the Biosynthesis of Triophamine by Triopha catalinae 134 V. A. Introduction to Polyketide Biosynthesis 135 V.B. Precedents for a Polyketide Origin of Triophamine 137 V.C. Feeding Experiments with Triopha catalinae 149 V.D. Endnotes: Chapter V: Biosynthesis of Triophamine 160 VI. Concluding Remarks 162 VLB. Endnotes: Chapter VI: Concluding Remarks 171 VII. Experimental 172 VII.B. Endnotes: Chapter VU: Experimental 181 VIII: Appendix A: Nuclear Magnetic Resonance Techniques 182 IX. Appendix B: Isolation of Known Compounds from New Sources 190 vi LIST OF TABLES Page Table 1: lH, 13C, COSY, HMBC, and nOe NMR Data for lovenone (2) 19 Table 2: 1H,13C, COSY, and HMBC Data for limaciamine (8) 53 Table 3: Specific Incorporation Data for the [1,2-13C2] acetate Feeding Experiments with Archidoris odhneri and A. montereyensis 95 Table 4: NMR Data for nanaimool (41) and isoacanthodorol (43) 121 Table 5: NMR Incorporation Data for Labeled nanaimool (41) and isoacanthodorol (43) 127 Table 6: Specific Incorporation Data for triophamine (9) 159 vii LIST OF FIGURES Page Figure 1: Anatomy of a Typical Dorid Nudibranch 5 Figure 2: Color Plate of Adalaria loveni 8 Figure 3: 1H NMR Spectrum of lovenone (2) [500 MHz, C^] 12 Figure 4: 13C Spectrum of lovenone (2) [ 125 MHz, C&>6\ 13 Figure 5: APT Spectrum of lovenone (2) [125 MHz, C^Dd 14 Figure 6: HMQC Spectrum of lovenone (2) [500 MHz, QDg] 15 Figure 7: Expanded Upfield Region of HMQC Spectrum of lovenone (2) [500 MHz, C6D6] 16 Figure 8: Electron Impact Mass Spectrum of lovenone (2) 17 Figure 9: Fourier Transform Infrared (FT-IR) Spectrum of lovenone (2) 18 Figure 10: Fragment Describing Ring C of lovenone (2) 21 Figure 11: COSY Spectrum of lovenone (2) [500 MHz, C6D6] 22 Figure 12: Expanded Upfield Region of COSY Spectrum of lovenone (2) [500 MHz, C6D6] 23 Figure 13: Expanded Methyl Region of HMBC Spectrum of lovenone (2) [500 MHz, C6D6] 24 Figure 14: Fragment Describing Ring B of lovenone (2) 25 Figure 15: Expanded Region of HMBC Spectrum of lovenone (2) [500 MHz, C6D6] Showing Correlations from the lH at 5 3.67 26 Figure 16: Expanded Region of HMBC Spectrum of lovenone (2) [500 MHz, C6D6] Showing Correlations from the *H at 8 2.05 27 Figure 17: Expanded Downfield Region of HMBC Spectrum of lovenone (2) [500 MHz, C6D6] 28 Figure 18: Fragment Describing Ring D of lovenone (2) 29 Figure 19: Downfield Region of ]H Spectrum of lovenone (2) Recorded in d6-DMSO [500 MHz] 30 Figure 20: Downfield Region of !H Spectrum of lovenone (2) Recorded in d6-DMSO + D20 [500 MHz] 30 Figure 21: Expanded Region of COSY Spectrum of lovenone (2) in d6-DMSO 500 MHz] 31 Figure 22: Fragment Describing Side-Chain of lovenone (2) 33 Figure 23: Expanded Region (*H 8 1.5 to 1.8) of HMBC Spectrum of lovenone (2) [500 MHz, C^] 34 Figure 24: Proposed Conformation of lovenone (2) 35 Figure 25: Selected Difference nOe Spectra of lovenone (2) 36 Figure 26: Color Plate of Limacia clavigera 41 Figure 27: !H Spectrum of limaciamine (8) [500 MHz, CDCI3] 44 Figure 28: FT-IR Spectrum of limaciamine (8) [NaCl, thin film, neat] 45 Vlll Figure 29: Electron Impact Mass Spectrum of limaciamine (8) 46 Figure 30: 13C Spectrum of limaciamine (8) [125 MHz, CDCI3] 47 Figure 31: HMQC Spectrum of limaciamine (8) [500 MHz, CDCI3] 48 Figure 32: COSY Spectrum of limaciamine (8) [500 MHz, CDCI3] 49 Figure 33: Selected Region of HMBC Spectrum of limaciamine (8) [500 MHz, CDCI3] 50 Figure 34: Methyl Region of HMBC Spectrum of limaciamine (8) [500 MHz, CDCI3] 51 Figure 35: Color Plates of Archidoris odhneri (top) and A. montereyensis (bottom) 75 Figure 36: 1H Spectrum of farnesic acid glyceride (28) [500 MHz, CDCI3] 83 Figure 37: 13C Spectrum of farnesic acid glyceride (28) [125 MHz, CDCI3] 84 Figure 38: HMQC Spectrum of farnesic acid glyceride (28) [500 MHz, CDCI3] 85 Figure 39: Expanded Upfield Region of HMQC Spectrum of farnesic acid glyceride (28) [500 MHz, CDCI3] 86 Figure 40: HMBC Spectrum of farnesic acid glyceride (28) [500 MHz, CDCI3] 87 Figure 41: Expanded Upfield Region of HMBC Spectrum of farnesic acid glyceride (28) [500 MHz, CDCI3] 88 Figure 42: Expanded Region (Upfield
Load more

Recommended publications
  • A Radical Solution: the Phylogeny of the Nudibranch Family Fionidae
    RESEARCH ARTICLE A Radical Solution: The Phylogeny of the Nudibranch Family Fionidae Kristen Cella1, Leila Carmona2*, Irina Ekimova3,4, Anton Chichvarkhin3,5, Dimitry Schepetov6, Terrence M. Gosliner1 1 Department of Invertebrate Zoology, California Academy of Sciences, San Francisco, California, United States of America, 2 Department of Marine Sciences, University of Gothenburg, Gothenburg, Sweden, 3 Far Eastern Federal University, Vladivostok, Russia, 4 Biological Faculty, Moscow State University, Moscow, Russia, 5 A.V. Zhirmunsky Instutute of Marine Biology, Russian Academy of Sciences, Vladivostok, Russia, 6 National Research University Higher School of Economics, Moscow, Russia a11111 * [email protected] Abstract Tergipedidae represents a diverse and successful group of aeolid nudibranchs, with approx- imately 200 species distributed throughout most marine ecosystems and spanning all bio- OPEN ACCESS geographical regions of the oceans. However, the systematics of this family remains poorly Citation: Cella K, Carmona L, Ekimova I, understood since no modern phylogenetic study has been undertaken to support any of the Chichvarkhin A, Schepetov D, Gosliner TM (2016) A Radical Solution: The Phylogeny of the proposed classifications. The present study is the first molecular phylogeny of Tergipedidae Nudibranch Family Fionidae. PLoS ONE 11(12): based on partial sequences of two mitochondrial (COI and 16S) genes and one nuclear e0167800. doi:10.1371/journal.pone.0167800 gene (H3). Maximum likelihood, maximum parsimony and Bayesian analysis were con- Editor: Geerat J. Vermeij, University of California, ducted in order to elucidate the systematics of this family. Our results do not recover the tra- UNITED STATES ditional Tergipedidae as monophyletic, since it belongs to a larger clade that includes the Received: July 7, 2016 families Eubranchidae, Fionidae and Calmidae.
    [Show full text]
  • Diversity of Norwegian Sea Slugs (Nudibranchia): New Species to Norwegian Coastal Waters and New Data on Distribution of Rare Species
    Fauna norvegica 2013 Vol. 32: 45-52. ISSN: 1502-4873 Diversity of Norwegian sea slugs (Nudibranchia): new species to Norwegian coastal waters and new data on distribution of rare species Jussi Evertsen1 and Torkild Bakken1 Evertsen J, Bakken T. 2013. Diversity of Norwegian sea slugs (Nudibranchia): new species to Norwegian coastal waters and new data on distribution of rare species. Fauna norvegica 32: 45-52. A total of 5 nudibranch species are reported from the Norwegian coast for the first time (Doridoxa ingolfiana, Goniodoris castanea, Onchidoris sparsa, Eubranchus rupium and Proctonotus mucro- niferus). In addition 10 species that can be considered rare in Norwegian waters are presented with new information (Lophodoris danielsseni, Onchidoris depressa, Palio nothus, Tritonia griegi, Tritonia lineata, Hero formosa, Janolus cristatus, Cumanotus beaumonti, Berghia norvegica and Calma glau- coides), in some cases with considerable changes to their distribution. These new results present an update to our previous extensive investigation of the nudibranch fauna of the Norwegian coast from 2005, which now totals 87 species. An increase in several new species to the Norwegian fauna and new records of rare species, some with considerable updates, in relatively few years results mainly from sampling effort and contributions by specialists on samples from poorly sampled areas. doi: 10.5324/fn.v31i0.1576. Received: 2012-12-02. Accepted: 2012-12-20. Published on paper and online: 2013-02-13. Keywords: Nudibranchia, Gastropoda, taxonomy, biogeography 1. Museum of Natural History and Archaeology, Norwegian University of Science and Technology, NO-7491 Trondheim, Norway Corresponding author: Jussi Evertsen E-mail: [email protected] IntRODUCTION the main aims.
    [Show full text]
  • Phylum MOLLUSCA
    285 MOLLUSCA: SOLENOGASTRES-POLYPLACOPHORA Phylum MOLLUSCA Class SOLENOGASTRES Family Lepidomeniidae NEMATOMENIA BANYULENSIS (Pruvot, 1891, p. 715, as Dondersia) Occasionally on Lafoea dumosa (R.A.T., S.P., E.J.A.): at 4 positions S.W. of Eddystone, 42-49 fm., on Lafoea dumosa (Crawshay, 1912, p. 368): Eddystone, 29 fm., 1920 (R.W.): 7, 3, 1 and 1 in 4 hauls N.E. of Eddystone, 1948 (V.F.) Breeding: gonads ripe in Aug. (R.A.T.) Family Neomeniidae NEOMENIA CARINATA Tullberg, 1875, p. 1 One specimen Rame-Eddystone Grounds, 29.12.49 (V.F.) Family Proneomeniidae PRONEOMENIA AGLAOPHENIAE Kovalevsky and Marion [Pruvot, 1891, p. 720] Common on Thecocarpus myriophyllum, generally coiled around the base of the stem of the hydroid (S.P., E.J.A.): at 4 positions S.W. of Eddystone, 43-49 fm. (Crawshay, 1912, p. 367): S. of Rame Head, 27 fm., 1920 (R.W.): N. of Eddystone, 29.3.33 (A.J.S.) Class POLYPLACOPHORA (=LORICATA) Family Lepidopleuridae LEPIDOPLEURUS ASELLUS (Gmelin) [Forbes and Hanley, 1849, II, p. 407, as Chiton; Matthews, 1953, p. 246] Abundant, 15-30 fm., especially on muddy gravel (S.P.): at 9 positions S.W. of Eddystone, 40-43 fm. (Crawshay, 1912, p. 368, as Craspedochilus onyx) SALCOMBE. Common in dredge material (Allen and Todd, 1900, p. 210) LEPIDOPLEURUS, CANCELLATUS (Sowerby) [Forbes and Hanley, 1849, II, p. 410, as Chiton; Matthews. 1953, p. 246] Wembury West Reef, three specimens at E.L.W.S.T. by J. Brady, 28.3.56 (G.M.S.) Family Lepidochitonidae TONICELLA RUBRA (L.) [Forbes and Hanley, 1849, II, p.
    [Show full text]
  • Nudibranquios De La Costa Vasca: El Pequeño Cantábrico Multicolor
    Nudibranquios de la Costa Vasca: el pequeño Cantábrico multicolor Recopilación de Nudibranquios fotografiados en Donostia-San Sebastián Luis Mª Naya Garmendia Título: Nudibranquios de la Costa Vasca: el pequeño Cantábrico multicolor © Texto y Fotografías: Luis Mª Naya. Las fotografías del Thecacera pennigera fueron reali- zadas por Michel Ranero y Jesús Carlos Preciado. Editado por el Aquarium de Donostia-San Sebastián Carlos Blasco de Imaz Plaza, 1 20003 Donostia-San Sebastián Tfno.: 943 440099 www.aquariumss.com 2016 Maquetación: Imanol Tapia ISBN: 978-84-942751-04 Dep. Legal: SS-????????? Imprime: Michelena 4 Índice Prólogo, Vicente Zaragüeta ...................................................................... 9 Introducción ................................................................................................... 11 Nudibranquios y otras especies marinas ............................................... 15 ¿Cómo es un nudibranquio? ..................................................................... 18 Una pequeña Introducción Sistemática a los Opistobranquios, Jesús Troncoso ........................................................................................... 25 OPISTOBRANQUIOS .................................................................................... 29 Aplysia fasciata (Poiret, 1789) .............................................................. 30 Aplysia parvula (Morch, 1863) ............................................................. 32 Aplysia punctata (Cuvier, 1803) ..........................................................
    [Show full text]
  • Rachor, E., Bönsch, R., Boos, K., Gosselck, F., Grotjahn, M., Günther, C
    Rachor, E., Bönsch, R., Boos, K., Gosselck, F., Grotjahn, M., Günther, C.-P., Gusky, M., Gutow, L., Heiber, W., Jantschik, P., Krieg, H.J., Krone, R., Nehmer, P., Reichert, K., Reiss, H., Schröder, A., Witt, J. & Zettler, M.L. (2013): Rote Liste und Artenlisten der bodenlebenden wirbellosen Meerestiere. – In: Becker, N.; Haupt, H.; Hofbauer, N.; Ludwig, G. & Nehring, S. (Red.): Rote Liste gefährdeter Tiere, Pflanzen und Pilze Deutschlands, Band 2: Meeresorganismen. – Münster (Landwirtschaftsverlag). – Na- turschutz und Biologische Vielfalt 70 (2): S. 81-176. Die Rote Liste gefährdeter Tiere, Pflanzen und Pilze Deutschlands, Band 2: Meeres- organismen (ISBN 978-3-7843-5330-2) ist zu beziehen über BfN-Schriftenvertrieb – Leserservice – im Landwirtschaftsverlag GmbH 48084 Münster Tel.: 02501/801-300 Fax: 02501/801-351 http://www.buchweltshop.de/bundesamt-fuer-naturschutz.html bzw. direkt über: http://www.buchweltshop.de/nabiv-heft-70-2-rote-liste-gefahrdeter-tiere-pflanzen-und- pilze-deutschlands-bd-2-meeresorganismen.html Preis: 39,95 € Naturschutz und Biologische Vielfalt 70 (2) 2013 81 –176 Bundesamtfür Naturschutz Rote Liste und Artenlisten der bodenlebenden wirbellosen Meerestiere 4. Fassung, Stand Dezember 2007, einzelne Aktualisierungenbis 2012 EIKE RACHOR,REGINE BÖNSCH,KARIN BOOS, FRITZ GOSSELCK, MICHAEL GROTJAHN, CARMEN- PIA GÜNTHER, MANUELA GUSKY, LARS GUTOW, WILFRIED HEIBER, PETRA JANTSCHIK, HANS- JOACHIM KRIEG,ROLAND KRONE, PETRA NEHMER,KATHARINA REICHERT, HENNING REISS, ALEXANDER SCHRÖDER, JAN WITT und MICHAEL LOTHAR ZETTLER unter Mitarbeit von MAREIKE GÜTH Zusammenfassung Inden hier vorgelegten Listen für amMeeresbodenlebende wirbellose Tiere (Makrozoo- benthos) aus neun Tierstämmen wurden 1.244 Arten bewertet. Eszeigt sich, dass die Verhältnis- se in den deutschen Meeresgebietender Nord-und Ostsee (inkl.
    [Show full text]
  • Full Text in Pdf Format
    Vol. 9: 57–71, 2017 AQUACULTURE ENVIRONMENT INTERACTIONS Published February 8§ doi: 10.3354/aei00215 Aquacult Environ Interact OPEN ACCESS Successional changes of epibiont fouling communities of the cultivated kelp Alaria esculenta: predictability and influences A. M. Walls1,*, M. D. Edwards1, L. B. Firth2, M. P. Johnson1 1Irish Seaweed Research Group, Ryan Institute, National University of Ireland, Galway, Ireland 2School of Geography, Earth & Environmental Science, Plymouth University, Drake Circus, Plymouth PL4 8AA, UK ABSTRACT: There has been an increase in commercial-scale kelp cultivation in Europe, with fouling of cultivated kelp fronds presenting a major challenge to the growth and development of the industry. The presence of epibionts decreases productivity and impacts the commercial value of the crop. Several abiotic and biotic factors may influence the occurrence and degree of fouling of wild and cultivated fronds. Using a commercial kelp farm on the SW coast of Ireland, we studied the development of fouling communities on cultivated Alaria esculenta fronds over 2 typical grow- ing seasons. The predictability of community development was assessed by comparing mean occurrence-day. Hypotheses that depth, kelp biomass, position within the farm and the hydrody- namic environment affect the fouling communities were tested using species richness and com- munity composition. Artificial kelp mimics were used to test whether local frond density could affect the fouling communities. Species richness increased over time during both years, and spe- cies composition was consistent over years with early successional communities converging into later communities (no significant differences between June 2014 and June 2015 communities, ANOSIM; R = −0.184, p > 0.05).
    [Show full text]
  • Seasearch North Wales 2019 Summary Report
    Seasearch North Wales 2019 Summary Report Report prepared by Lucy Kay, Seasearch Tutor Seasearch Gogledd Cymru 2019 Cynllun gwirfoddol sy’n arolygu rhywogaethau a chynefinoedd morol yw Seasearch ar gyfer deifwyr sy’n deifio yn eu hamser hamdden ym Mhrydain ac Iwerddon. Mae’r cynllun yn cael ei gydlynu yn genedlaethol gan y Gymdeithas Cadwraeth Forol. Mae’r adroddiad hwn yn crynhoi gweithgareddau Seasearch yng Ngogledd Cymru yn ystod 2019. Mae’n cynnwys crynodebau o’r safleoedd a arolygwyd ac yn nodi rhywogaethau a chynefinoedd prin neu anghyffredin a welwyd. Mae’r rhain yn cynnwys nifer o gynefinoedd a rhywogaethau â blaenoriaeth yng Nghymru. Nid yw’r adroddiad hwn yn cynnwys yr holl fanylion data gan fod y rhain wedi eu cofnodi yn y gronfa ddata Marine Recorder a gyflwynwyd i Cyfoeth Naturiol Cymru i’w defnyddio yn ei weithgareddau cadwraeth forol. Mae’r data rhywogaethau hefyd ar gael ar-lein drwy Rwydwaith Bioamrywiaeth Cenedlaethol Atlas. Yn ystod 2019, roedd Seasearch yng Ngogledd Cymru yn parhau i ganolbwyntio ar rywogaethau a chynefinoedd â blaenoriaeth yn ogystal â chasglu gwybodaeth am wely’r môr a bywyd morol ar gyfer safleoedd nad oeddent wedi cael eu harolygu yn flaenorol. Mae’r data o Ogledd Cymru yn 2019 yn cynnwys 15 o Ffurflenni Arolygu a 34 o Ffurflenni Arsylwi, sef 49 ffurflen i gyd. Yn 2019 cyflawnwyd gwaith Seasearch yng Ngogledd Cymru gan Holly Date, cydlynydd rhanbarthol Seasearch yng Ngogledd Cymru; mae ardal Seasearch Gogledd Cymru yn ymestyn o Aberystwyth i Afon Dyfrdwy. Mae’r cydlynydd yn cael ei gynorthwyo gan nifer o Diwtoriaid gweithredol Seasearch, Tiwtoriaid Cynorthwyol a Threfnwyr Deifio.
    [Show full text]
  • <I>Hypselodoris Picta</I>
    BULLETIN OF MARINE SCIENCE, 63(1): 133–141, 1998 ANATOMICAL DATA ON A RARE HYPSELODORIS PICTA (SCHULTZ, 1836) (GASTROPODA, DORIDACEA) FROM THE COAST OF BRAZIL WITH DESCRIPTION OF A NEW SUBSPECIES J. S. Troncoso, F. J. Garcia and V. Urgorri ABSTRACT A rare specimen of the chromodorid doridacean Hypselodoris picta (Schultz, 1836), is described from the southeast coast of Brazil. The coloration of this specimen differs from the typical pattern of the species, mainly due to the presence of a white marginal notal band and dark blue gills without yellow lines on their rachis, as is typical in H. picta. Along with this, the morphology of the reproductive system and the radular teeth of this specimen differs from those of other H. picta. The results of a comparative analysis of Hypselodoris picta is presented in this paper, with description of a new subspecies. As was stated by Gosliner (1990), the large species of Atlantic Hypselodoris Stimpson,1855, have been the subject of some taxonomical confusion. Ortea, et al. (1996) studied many specimens of Hypselodoris from diferent Atlantic and Mediterranean re- gions which allowed them to conclude that H. webbi (d’Orbigny, 1839) and H. valenciennesi (Cantraine, 1841) have to be considered as synonyms of H. picta (Schultz, 1836). H. picta is a known amphi-Atlantic species from Florida, Puerto Rico and Brazil (Marcus, 1977, cited as H. sycilla), Azores islands (Gosliner, 1990), Canary Islands (Bouchet and Ortea, 1980), the Atlantic coasts of France and Spain (Bouchet and Ortea, 1980; Cervera, et al. 1988) and the Mediterranean Sea (Thompson and Turner, 1983).
    [Show full text]
  • ZM75-01 | Yonow 11-01-2007 15:03 Page 1
    ZM75-01 | yonow 11-01-2007 15:03 Page 1 Results of the Rumphius Biohistorical Expedition to Ambon (1990) Part 11. Doridacea of the families Chromodorididae and Hexa- branchidae (Mollusca, Gastropoda, Opisthobranchia, Nudibranchia), including additional Moluccan material N. Yonow Yonow, N. Results of the Rumphius Biohistorical Expedition to Ambon (1990). Part 11. Doridacea of the families Chromodorididae and Hexabranchidae (Mollusca, Gastropoda, Opisthobranchia, Nudibran- chia), including additional Moluccan material. Zool. Med. Leiden 75 (1), 24.xii.2001: 1-50, figs 1-12, colour plts 1-5— ISSN 0024-0672. Nathalie Yonow, School of Biological Sciences, University of Wales, Singleton Park, Swansea SA2 8PP, Wales, U.K. (e-mail: [email protected]). Key words: Indonesia; Ambon; Chromodorididae; Hexabranchidae; Nudibranchia; Opisthobranchia; Gastropoda; systematics; taxonomy. Twenty-one species belonging to the family Chromodorididae and one species of Hexabranchus (Hexa- branchidae) are present in the 1990 Rumphius Biohistorical Expedition (RBE) collection. The 1996 Fauna Malesiana Marine Maluku Expedition (Mal) collected 43 lots of nudibranchs, mostly chromodorids: 17 species were identified, six of which were not represented in the RBE collection. A total of 35 chro- modorid species, belonging to nine genera, are described from Ambon and nearby localities. Four species are new to science, and seventeen species are recorded from Indonesian waters for the first time. Brief descriptions are given for the species which are well known, highlighting significant features, dif- ferentiating characters from similar species, and allowing recognition. A number of species are less well known and described and figured in more detail. The name Chromodoris marindica nom. nov. is proposed for Chromodoris reticulata sensu Eliot, 1904, and Farran, 1905 (not C.
    [Show full text]
  • Temperature-Mediated Outbreak Dynamics of the Invasive Bryozoan Membranipora Membranacea in Nova Scotian Kelp Beds
    Vol. 390: 1–13, 2009 MARINE ECOLOGY PROGRESS SERIES Published September 18 doi: 10.3354/meps08207 Mar Ecol Prog Ser OPENPEN ACCESSCCESS FEATURE ARTICLE Temperature-mediated outbreak dynamics of the invasive bryozoan Membranipora membranacea in Nova Scotian kelp beds Robert E. Scheibling1,*, Patrick Gagnon1, 2 1Department of Biology, Dalhousie University, Halifax, Nova Scotia B3H 4J1, Canada 2Present address: Ocean Sciences Centre, Memorial University of Newfoundland, St. John’s, Newfoundland A1C 5S7, Canada ABSTRACT: We used underwater videography to examine seasonal and interannual patterns in the cover (on kelp) of the encrusting epiphytic bryo- zoan Membranipora membranacea, and associated changes in the structure and abundance of native kelp (Saccharina longicruris) populations, at 2 sites on the Atlantic coast of Nova Scotia and over 4 to 11 yr since initial introduction of this invasive species around 1992. We show that (1) changes in the cover of M. membranacea on kelp, and in the cover of kelp on the seabed, are reciprocal and seasonal; (2) ther- mal history during the summer/fall period of bryo- zoan colony growth explains a large proportion (83%) of the interannual variation in peak cover of M. membranacea on kelp; and (3) annual decreases The epiphytic bryozoan Membranipora membranacea en- in kelp cover and blade size are related to the crusting blades of kelp Saccharina longicruris in Nova Scotia degree of infestation by M. membranacea, and not to Photo: Robert Scheibling wave action alone. Particularly severe outbreaks of M. membranacea, resulting in extensive defoliation of kelp beds, occurred in 1993, 1997 and 1999. Our field observations indicate that recurrent seasonal outbreaks of this invasive bryozoan can have a INTRODUCTION devastating effect on native kelp populations in Nova Scotia, which, in turn, facilitates the establish- Marine ecosystems worldwide are impacted by a ment and growth of the invasive green alga Codium high and accelerating rate of human-mediated species fragile ssp.
    [Show full text]
  • The Extraordinary Genus Myja Is Not a Tergipedid, but Related to the Facelinidae S
    A peer-reviewed open-access journal ZooKeys 818: 89–116 (2019)The extraordinary genusMyja is not a tergipedid, but related to... 89 doi: 10.3897/zookeys.818.30477 RESEARCH ARTICLE http://zookeys.pensoft.net Launched to accelerate biodiversity research The extraordinary genus Myja is not a tergipedid, but related to the Facelinidae s. str. with the addition of two new species from Japan (Mollusca, Nudibranchia) Alexander Martynov1, Rahul Mehrotra2,3, Suchana Chavanich2,4, Rie Nakano5, Sho Kashio6, Kennet Lundin7,8, Bernard Picton9,10, Tatiana Korshunova1,11 1 Zoological Museum, Moscow State University, Bolshaya Nikitskaya Str. 6, 125009 Moscow, Russia 2 Reef Biology Research Group, Department of Marine Science, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand 3 New Heaven Reef Conservation Program, 48 Moo 3, Koh Tao, Suratthani 84360, Thailand 4 Center for Marine Biotechnology, Department of Marine Science, Faculty of Science, Chulalongkorn Univer- sity, Bangkok 10330, Thailand5 Kuroshio Biological Research Foundation, 560-I, Nishidomari, Otsuki, Hata- Gun, Kochi, 788-0333, Japan 6 Natural History Museum, Kishiwada City, 6-5 Sakaimachi, Kishiwada, Osaka Prefecture 596-0072, Japan 7 Gothenburg Natural History Museum, Box 7283, S-40235, Gothenburg, Sweden 8 Gothenburg Global Biodiversity Centre, Box 461, S-40530, Gothenburg, Sweden 9 National Mu- seums Northern Ireland, Holywood, Northern Ireland, UK 10 Queen’s University, Belfast, Northern Ireland, UK 11 Koltzov Institute of Developmental Biology RAS, 26 Vavilova Str., 119334 Moscow, Russia Corresponding author: Alexander Martynov ([email protected]) Academic editor: Nathalie Yonow | Received 10 October 2018 | Accepted 3 January 2019 | Published 23 January 2019 http://zoobank.org/85650B90-B4DD-4FE0-8C16-FD34BA805C07 Citation: Martynov A, Mehrotra R, Chavanich S, Nakano R, Kashio S, Lundin K, Picton B, Korshunova T (2019) The extraordinary genus Myja is not a tergipedid, but related to the Facelinidae s.
    [Show full text]
  • The Opisthobranchs of Cape Arago. Oregon. with Notes
    THE OPISTHOBRANCHS OF CAPE ARAGO. OREGON. WITH NOTES ON THEIR NATURAL HISTORY AND A SUMMARY OF BENTHIC OPISTHOBRANCHS KNOWN FROM OREGON by JEFFREY HAROLD RYAN GODDARD A THESIS Presented to the Department of Biology and the Graduate School of the University of Oregon in partial fulfillment of the requirements for the degree of Master of Science December 1983 !tIl. ii I :'" APPROVED: -------:n:pe:;-;t::;e:;:-rt;l;1T:-.JF~r:aaD:inkk--- i I-I 1 iii An Abstract of the Thesis of Jeffrey Harold Ryan Goddard for the degree of Master of Science in the Department of Biology to be taken December 1983 TITLE: THE OPISTHOBRANCHS OF CAPE ARAGO, OREGON, WITH NOTES ON THEIR NATURAL HISTORY AND A SUM}~Y OF BENTHIC OPISTHOBRANCHS KNOWN FROM OREGON Approved: Peter W. Frank The opisthobranch molluscs of Oregon have been little studied, and little is known about the biology of many species. The present study consisted of field and laboratory observations of Cape Arago opistho- branchs. Forty-six species were found, extending the range of six north- ward and two southward. New food records are presented for nine species; an additional 20 species were observed feeding on previously recorded prey. Development data are given for 21 species. Twenty produce plank- totrophic larvae, and Doto amyra produces lecithotrophic larvae, the first such example known from Eastern Pacific opisthobranchs. Hallaxa chani appears to be the first eudoridacean nudibranch known to have a subannual life cycle. Development, life cycles, food and competition, iv ranges, and the ecological role of nudibranchs are discussed. Nudi- branchs appear to significantly affect the diversity of the Cape Arago encrusting community.
    [Show full text]