DOCSLIB.ORG

Profiling of Heterobranchia Sea Slugs from Portuguese

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Profiling of Heterobranchia Sea Slugs from Portuguese molecules Article Profiling of Heterobranchia Sea Slugs from Portuguese Coastal Waters as Producers of Anti-Cancer and Anti-Inflammatory Agents Nelson G. M. Gomes 1,* ID ,Fátima Fernandes 1, Áurea Madureira-Carvalho 1,2 ID , Patrícia Valentão 1 ID , Alexandre Lobo-da-Cunha 3,4, Gonçalo Calado 5,6 and Paula B. Andrade 1,* ID 1 REQUIMTE/LAQV, Laboratory of Pharmacognosy, Departament of Chemistry, Faculty of Pharmacy, University of Porto, R. Jorge Viterbo Ferreira, no. 228, 4050-313 Porto, Portugal; [email protected] (F.F.); [email protected] (Á.M.-C.); [email protected] (P.V.) 2 IINFACTS—Institute of Research and Advanced Training in Health Sciences and Technologies, Department of Sciences, University Institute of Health Sciences (IUCS), CESPU, CRL, Central de Gandra Street, 1317, 4585-116 Gandra PRD, Portugal 3 Departamento de Microscopia, Instituto de Ciências Biomédicas Abel Salazar (ICBAS), Universidade do Porto, 4050-313 Porto, Portugal; [email protected] 4 Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), 4450-208 Matosinhos, Portugal 5 Departamento de Ciências da Vida, Universidade Lusófona de Humanidades e Tecnologia, 1749-024 Lisboa, Portugal; [email protected] 6 MARE NOVA. Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Departamento de Ciências e Engenharia do Ambiente, Campus da Caparica, 2829-516 Caparica, Portugal * Correspondence: [email protected] (N.G.M.G.); [email protected] (P.B.A.); Tel.: +35-122-042-8500 (N.G.M.G.); +35-122-042-8654 (P.B.A.) Received: 15 March 2018; Accepted: 25 April 2018; Published: 27 April 2018 Abstract: Bioprospection of marine invertebrates has been predominantly biased by the biological richness of tropical regions, thus neglecting macro-organisms from temperate ecosystems. Species that were not the object of studies on their biochemical composition include the Heterobranchia gastropods Armina maculata, Armina tigrina and Aglaja tricolorata, inhabitants of the Portuguese Atlantic coastal waters. Here, we present for the first time the fatty acid profile of neutral lipids and homarine content of these three species. Qualitative and quantitative differences in the fatty acid content among species points to the existence of a fatty acid profile of neutral lipids, particularly of each genus. The results from cytotoxicity assays, using the acetonic extracts of the gastropods on human gastric adenocarcinoma (AGS) and human lung adenocarcinoma (A549) cell lines, revealed a pronounced cytotoxic effect of the A. tigrina extract on both cell lines (IC50 values of 68.75 and 69.77 µg mL−1 for AGS and A549, respectively). It is worth noting the significant reduction of NO levels in LPS-challenged RAW 264.7 macrophages exposed to A. tricolorata extract, at concentrations as low as 125 µg mL−1. Keywords: Armina spp.; Aglaja tricolorata; sea slugs; fatty acids; PUFA; EPA; DHA; homarine 1. Introduction The increasing number of reports on the structural variety and pharmacological properties of naturally occurring compounds obtained from marine invertebrates [1,2] has been driving the focus on several taxonomic groups, namely Heterobranchia mollusks [3,4]. Molecules 2018, 23, 1027; doi:10.3390/molecules23051027 www.mdpi.com/journal/molecules Molecules 2018, 23, 1027 2 of 15 Driven by the richer biological diversity compared to temperate regions, marine organisms from tropical ecosystems have been preferentially targeted as sources of therapeutically useful chemical agents [5]. Despite the geographical trends, bioprospection of temperate environments has been rewarding, leading to the discovery of a significant number of compounds from marine invertebrates [6]. Several species of nudibranchs, such as Armina spp., are widely distributed in the Mediterranean and Atlantic coasts, namely Armina maculata Rafinesque, 1814 and Armina tigrina Rafinesque, 1814 [7]. The cephalaspidean Aglaja tricolorata Renier, 1807 shares a similar geographical distribution, being also recorded along the Atlantic coast [8]. Despite their ubiquitous distribution, inhabiting sub-tropical and temperate shores [9], the above-mentioned species are considered scarce and/or seldom found, the chemical investigation of both genera being virtually absent [10]. There is a single study on the isolation of briarane and cembrane diterpenoids from A. maculata, and their subsequent identification in its prey Veretillum cynomorium [11]. As building blocks of several biologically relevant molecules, fatty acids act as biochemical mediators, energy sources and structural components [12], being obtained through heterotrophic and autotrophic pathways. They are frequently used as chemotaxonomic and chemo-ecological markers in some taxonomic groups [13]. While the fatty acid profile of a marine invertebrate is predominantly determined by its dietary sources, environmental and biotic factors can influence on the profile, providing valuable information on its ecological traits and supporting their chemotaxonomic discrimination [13,14]. Several experimental and epidemiological studies have demonstrated that specific classes of fatty acids, namely polyunsaturated fatty acids (PUFA), exhibit anti-cancer effects and immunoactive functions [15,16], playing also a pivotal role on the inflammatory process as precursors of eicosanoids [17]. Given the regression of the shell, and lack of an acquired immune system, some mollusks have evolved alternative mechanisms of defense, being active producers of bioactive metabolites for circulation in the hemolymph, as well as toxic and deterrent secretions, frequently containing molecules exhibiting anti-inflammatory and cytotoxic properties [18]. In addition to fatty acids, the biosynthetic machinery of marine macro-organisms enables the production of secondary metabolites falling into a wide range of structural classes. With the current study, we aimed to investigate the chemical profiles of A. maculata, A. tigrina and A. tricolorata, providing further insights on their metabolome. Considering that Heterobranchia sea slugs rely mainly on chemical defenses through the production of intrinsically active molecules, it was also our aim to assess their cytotoxicity towards human gastric (AGS) and human lung (A549) adenocarcinoma cell lines, as well as the anti-inflammatory potential, evaluated through the interference with the production of nitric oxide (NO) in lipopolysaccharide (LPS)-challenged RAW 264.7 macrophages. 2. Results 2.1. Chemical Characterization 2.1.1. Fatty Acid Profiles As shown in Table1, specimens under study are characterized by a complex fatty acid profile, their quantification revealing total fatty acid concentrations ranging from 136.21 to 165.81 µg mg−1 dry extract. In A. maculata and A. tigrina extracts, 23 and 26 fatty acids were characterized, respectively, while, in A. tricolorata extract, 18 fatty acids were identified, indicating clear differences between the two genera. Concerning the main constituents, the fatty acids contents of A. maculata and A. tigrina were rather similar, C16:0, C18:0, C20:4n-6, and C20:5n-3 being identified as the main components (>10%, each), accounting for approximately 63% of the total fatty acid content. Nonetheless, the saturated fatty acids (SFA) C21:0 and C22:0, and the PUFA C18:2n-6t were detected only in A. tigrina extract. While C16:0, C18:0 and C20:5n-3 were also identified as main components, the acetone extract of A. tricolorata exhibited high contents of C20:2n-6 (ca. 12%) and C22:6n-3 (ca. 13%). Moreover, distinct proportions of the different classes of fatty acids was also evidenced for the two genera (Figure1). Molecules 2018, 23, 1027 3 of 15 A. maculata and A. tigrina presented a similar qualitative profile concerning the SFA, monounsaturated fatty acids (MUFA) and PUFA content, while A. tricolorata was significantly richer in PUFA (ca. 57%). The cephalaspidean A. tricolorata exhibited a significantly higher proportion of n-3 PUFA (n-6/n-3 < 1), in contrast with the nudibranchs A. maculata and A. tigrina with a n-6/n-3 ratio higher than 1.75 (Table1). Table 1. Fatty acid content of A. maculata, A. tigrina and A. tricolorata extracts (µg mg−1 dry extract) 1. Compound A. maculata A. tigrina A. tricolorata µg mg−1 Relative µg mg−1 Relative µg mg−1 Relative dry extract % dry extract % dry extract % SFA C12:0 nq nq nq nq - - C13:0 nq nq nq nq - - C14:0 1.20 (0.05) 0.75 1.64 (0.04) 1.20 1.18 (0.16) 0.71 C15:0 1.14 (0.04) 0.87 1.14 (0.06) 0.84 1.69 (0.07) 1.02 C16:0 30.43 (2.82) 19.08 25.73 (1.10) 18.89 21.28 (1.67) 12.84 C17:0 14.60 (0.38) 9.16 13.38 (0.50) 9.82 9.71 (0.61) 5.86 C18:0 18.42 (0.49) 11.55 15.20 (0.69) 11.16 15.99 (1.05) 9.64 C20:0 1.36 (0.02) 0.85 3.70 (0.11) 2.72 nq nq C21:0 - - nq nq - - C22:0 - - 2.79 (0.14) 2.05 - - MUFA C14:1n-5 nq nq nq nq nq nq C15:1n-5 1.39 (0.14) 0.87 1.48 (0.17) 1.09 - - C16:1n-7 1.72 (0.07) 1.08 2.78 (0.33) 2.04 3.46 (0.17) 2.09 C17:1n-7 1.13 (0.17) 0.71 1.79 (0.11) 1.32 - - C18:1n-9c 3.91 (0.20) 2.45 3.91 (0.42) 2.87 9.81 (0.64) 5.92 C18:1n-9t 3.56 (0.28) 2.23 1.71 (0.22) 1.25 7.43 (0.46) 4.48 C22:1n-9 1.07 (0.14) 0.67 nq nq - - PUFA C18:2n-6c 4.27 (0.27) 2.68 2.36 (0.15) 1.74 3.16 (0.14) 1.91 C18:2n-6t - - nq nq - - C20:2n-6 11.05 (1.23) 6.93 6.68 (0.89) 4.91 19.38 (0.81) 11.69 C18:3n-6c nq nq nq nq 2.18 (0.09) 1.31 C18:3n-3c 4.37 (0.44) 2.74 1.99 (0.24) 1.46 4.20 (0.25) 2.53 C20:3n-6 5.95 (0.72) 3.73 4.30 (0.78) 3.16 9.63 (0.33) 5.81 C20:4n-6 30.34 (2.18) 19.03 25.54 (0.93) 18.75 11.38 (0.72) 6.87 C20:5n-3 20.00 (1.22) 12.54 18.42 (0.87) 13.52 24.02 (1.59) 14.49 C22:6n-3
Load more

Recommended publications
  • Some Opisthobranchs from West Africa
    SOME OPISTHOBRANCHS FROM WEST AFRICA BY KATHLEEN M. WHITE, Ph. D., M. Se. (Reading) 12 SOME OPISTHOBRANCHS FR OM WEST AFRICA The following report is based upon material submitted to me by the Director oi' the Institut Royal des 'Sciences Naturelles of Belgium whom I wish to thank for the opportunity of examining it. It comprises material eollected by the training-ship « Mercator » on lier 9th voyage in 1935-6, her llth voyage in 1936-7 and her 14th voyage in 1937-8. Additional specimens were eollected by the Belgian expédition to the South Atlantic in 1948-49 and from West Afriea in 1953. The région covered is the west coast of Africa from Bio de Oro in the north to Angola on the south, and it lies roughly between longitudes 17° West to 13° East and latitudes 26° North and 15° South. The depths extend from shore down to 50 fathoms. The Opisthobranchs of tliis région have received no attention. Collections from Morocco in the north have been reported upon bv A. Pruvot-Fol in 1927 and 1953 and bv J. Risbec in 1931. Collections from S. Africa have been described bv R. Bergh in 1908, K. H. Barnard in 1927, C. H. O'Donoghue in 1928 and N. B. Eales and H. Engel in 1935. References to these reports have heen made and to A. Vayssiere's accounts of the Mediterranean fauna publislied between 1865 and 1919. In all twenty-six species of Opisthobranchs have been recognised of which eighteen are previously described species, two are new varieties of know species and four appear to be new species.
    [Show full text]
  • Prey Preference Follows Phylogeny: Evolutionary Dietary Patterns Within the Marine Gastropod Group Cladobranchia (Gastropoda: Heterobranchia: Nudibranchia) Jessica A
    Goodheart et al. BMC Evolutionary Biology (2017) 17:221 DOI 10.1186/s12862-017-1066-0 RESEARCHARTICLE Open Access Prey preference follows phylogeny: evolutionary dietary patterns within the marine gastropod group Cladobranchia (Gastropoda: Heterobranchia: Nudibranchia) Jessica A. Goodheart1,2* , Adam L. Bazinet1,3, Ángel Valdés4, Allen G. Collins2 and Michael P. Cummings1 Abstract Background: The impact of predator-prey interactions on the evolution of many marine invertebrates is poorly understood. Since barriers to genetic exchange are less obvious in the marine realm than in terrestrial or freshwater systems, non-allopatric divergence may play a fundamental role in the generation of biodiversity. In this context, shifts between major prey types could constitute important factors explaining the biodiversity of marine taxa, particularly in groups with highly specialized diets. However, the scarcity of marine specialized consumers for which reliable phylogenies exist hampers attempts to test the role of trophic specialization in evolution. In this study, RNA- Seq data is used to produce a phylogeny of Cladobranchia, a group of marine invertebrates that feed on a diverse array of prey taxa but mostly specialize on cnidarians. The broad range of prey type preferences allegedly present in two major groups within Cladobranchia suggest that prey type shifts are relatively common over evolutionary timescales. Results: In the present study, we generated a well-supported phylogeny of the major lineages within Cladobranchia using RNA-Seq data, and used ancestral state reconstruction analyses to better understand the evolution of prey preference. These analyses answered several fundamental questions regarding the evolutionary relationships within Cladobranchia, including support for a clade of species from Arminidae as sister to Tritoniidae (which both preferentially prey on Octocorallia).
    [Show full text]
  • An Annotated Checklist of the Marine Macroinvertebrates of Alaska David T
    NOAA Professional Paper NMFS 19 An annotated checklist of the marine macroinvertebrates of Alaska David T. Drumm • Katherine P. Maslenikov Robert Van Syoc • James W. Orr • Robert R. Lauth Duane E. Stevenson • Theodore W. Pietsch November 2016 U.S. Department of Commerce NOAA Professional Penny Pritzker Secretary of Commerce National Oceanic Papers NMFS and Atmospheric Administration Kathryn D. Sullivan Scientific Editor* Administrator Richard Langton National Marine National Marine Fisheries Service Fisheries Service Northeast Fisheries Science Center Maine Field Station Eileen Sobeck 17 Godfrey Drive, Suite 1 Assistant Administrator Orono, Maine 04473 for Fisheries Associate Editor Kathryn Dennis National Marine Fisheries Service Office of Science and Technology Economics and Social Analysis Division 1845 Wasp Blvd., Bldg. 178 Honolulu, Hawaii 96818 Managing Editor Shelley Arenas National Marine Fisheries Service Scientific Publications Office 7600 Sand Point Way NE Seattle, Washington 98115 Editorial Committee Ann C. Matarese National Marine Fisheries Service James W. Orr National Marine Fisheries Service The NOAA Professional Paper NMFS (ISSN 1931-4590) series is pub- lished by the Scientific Publications Of- *Bruce Mundy (PIFSC) was Scientific Editor during the fice, National Marine Fisheries Service, scientific editing and preparation of this report. NOAA, 7600 Sand Point Way NE, Seattle, WA 98115. The Secretary of Commerce has The NOAA Professional Paper NMFS series carries peer-reviewed, lengthy original determined that the publication of research reports, taxonomic keys, species synopses, flora and fauna studies, and data- this series is necessary in the transac- intensive reports on investigations in fishery science, engineering, and economics. tion of the public business required by law of this Department.
    [Show full text]
  • Australasian Nudibranch News
    australasian nudibranchNEWS No.6 February 1999 Ceratosoma brevicuadatum Editors Notes Abraham, 1867 Helmut Debilius’s second edition of Nudibranchs and Sea Snails is now This species is endemic to the temper- available (see review page 4). Neville Coleman has supplied the updated spe- ate southern Australia, from Cape Byron in cies list for his Nudibranchs of the South Pacific (see page 3). For the full up- the east to Houtman Abrolhos in the west. It date, including the new distribution notes, send an email and we will forward a is the dominate species in Victorian waters. copy. The body and mantle colour can be The Port Stephens nudibranch list has drawn some attention, a film maker bright red, pink, orange, pale brown or yel- recently contacted us after seeing the list on our web site. We are now looking low and bear red, blue or purple spots often at how we can assist him in making a documentory on the Rocky Shore. All with white rings. The rhinophores and specimens are to be photographed and then released unharmed. tripinnate gills are the same colour as the Surfing the nudibranch sites recently I came across a site created by Lim mantle and foot. Yun Ping. Have a look at http://arl.nus.edu.sg/mandar/yp/EPIC/nudi.html The body is firm, high, slender and in- flexible. The mantle has a continuous wavy notal ridge which develops into a posterior Feedback mantle projection. This distinguishes it from In answer to Lindsay Warren's request for information: tropical species which have elongated and Helmut's book (Edition one): recurved projections.This species can grow page 139 (middle): is Philinopsis cyanea.
    [Show full text]
  • Armina Maculata Rafinesque, 1814 (Nudibranchia: Arminidae): a New Record for the Turkish Mollusc Fauna
    Turkish Journal of Zoology Turk J Zool (2014) 38: 508-509 http://journals.tubitak.gov.tr/zoology/ © TÜBİTAK Short Communication doi:10.3906/zoo-1309-26 Armina maculata Rafinesque, 1814 (Nudibranchia: Arminidae): a new record for the Turkish mollusc fauna Okan AKYOL*, Cemil SAĞLAM Faculty of Fisheries, Ege University, Urla, İzmir, Turkey Received: 18.09.2013 Accepted: 14.01.2014 Published Online: 20.05.2014 Printed: 19.06.2014 Abstract: A specimen of Armina maculata was collected on 10 July 2013 from İzmir Bay, north-eastern Aegean coast of Turkey. This short note represents a clear indication of the unique occurrence of an A. maculata in Turkish seas. Key words: Armina maculata, new record, İzmir Bay, Aegean Sea, Turkey The genus Armina, with more than 50 nominal species, fisherman using a trammel net (mesh size: 40 mm). The has a worldwide distribution; they are poorly known capture location was on the Urla coast (38°22′N, 26°46′E), nudibranchs (Kolb, 1998). Arminids are characterised İzmir Bay, at a depth of 25 m on a sandy-muddy bottom. by having an elongated, flattened body and a narrow The specimen was fixed in 4% formaldehyde solution posterior end with longitudinal ridges or pustules on the notum (Baez et al., 2011). Armina maculata Rafinesque, 1814 is 1 of the 3 Mediterranean arminids, along with A. neapolitana (delle Chiaje, 1824) and A. tigrina Rafinesque, 1814 (http://www. medslugs.de/E/mssmain.htm). Kolb (1998) described the external morphology of A. maculata as not having notal ridges, although irregularly arranged pustules occur on the notum; the living animals have white pustules; the ground colour of the mantle is orange.
    [Show full text]
  • On Melanochlamys Cheeseman, 1881, a Genus of the Aglajidae (Opisthobranchia, Gastropoda) 1
    On Melanochlamys Cheeseman, 1881, a Genus of the Aglajidae (Opisthobranchia, Gastropoda) 1 W. B. RUDMAN2 ABSTRACT: Melanochlamys Cheeseman, 1881, long considered to be a synonym of Aglaja Renier, 1807, is shown to be a distinct genus of the Aglajidae differing from other genera in external body form, shape of shell, alimentary canal, and re­ productive system. Specimens of the type species, M. cylindrica Cheeseman, 1881, are compared with M. lorrainae (Rudman, 1968), M. queritor (Burn, 1958), and M. diomedea (Bergh, 1893). It is suggested that Aglaja dubia O'Donoghue, 1929, A. ezoensis Baba, 1957, A. henri Burn, 1969, A. nana Steinberg & Jones, 1960, and A. seurati Vayssiere, 1926, also belong to Melanochlamys. IN 1881, Cheeseman described a new species the anterior half of the dorsum and posteriorly of aglajid from New Zealand, and, because of the edge is rounded forming a small loose flap. differences in the external form of the body Sometimes there is a small central indentation and nature of the shell, he erected a new genus on the posterior edge of the headshield. A Melanochlamys. From that date all subsequent slightly visible median line runs from the an­ workers (Pilsbry, 1896; Eliot, 1903; Bergh, terior end to halfway down the headshield. The 1907; O'Donoghue, 1929) have considered this posterior half of the dorsum forms a posterior name to be a junior synonym of Aglaja Renier, shield. The hind end of this shield overhangs 1807. However, after an extensive study of the the posterior end of the body and encloses the family, I have come to the conclusion that reduced shell.
    [Show full text]
  • Design and Implementation of a Biodiversity Information Management System: Electronic Catalogue of Known Indian Fauna – a Case Study
    DESIGN AND IMPLEMENTATION OF A BIODIVERSITY INFORMATION MANAGEMENT SYSTEM: ELECTRONIC CATALOGUE OF KNOWN INDIAN FAUNA – A CASE STUDY A THESIS SUBMITTED TO THE UNIVERSITY OF PUNE FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN BIOINFORMATICS BY VISHWAS CHAVAN UNDER THE GUIDANCE OF DR. S. KRISHNAN NATIONAL CHEMICAL LABORATORY PUNE SEPTEMBER 2007 DESIGN AND IMPLEMENTATION OF A BIODIVERSITY INFORMATION MANAGEMENT SYSTEM: ELECTRONIC CATALOGUE OF KNOWN INDIAN FAUNA – A CASE STUDY A THESIS SUBMITTED TO THE UNIVERSITY OF PUNE FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN BIOINFORMATICS BY VISHWAS CHAVAN UNDER THE GUIDANCE OF DR. S. KRISHNAN NATIONAL CHEMICAL LABORATORY PUNE SEPTEMBER 2007 DECLARATION I hereby declare that the work embodied in this thesis entitled “DESIGN AND IMPLEMENTATION OF A BIODIVERSITY INFORMATION MANAGEMENT SYSTEM: ELECTRONIC CATALOGUE OF KNOWN INDIAN FAUNA – A CASE STUDY” represents original work carried out by me under the supervision of Dr. S. Krishnan, Head, Information Division, National Chemical Laboratory, Pune. It has not been submitted previously for any other research degree of this or any other University. September 25, 2007 Vishwas Chavan National Chemical Laboratory Pune 411008, INDIA CERTIFICATE Certified that the work incorporated in the thesis entitled “DESIGN AND IMPLEMENTATION OF A BIODIVERSITY INFORMATION MANAGEMENT SYSTEM: ELECTRONIC CATALOGUE OF KNOWN INDIAN FAUNA – A CASE STUDY” submitted by Mr. Vishwas Chavan, was carried out by the candidate under my supervision. Materials obtained from other sources have been duly acknowledged in the thesis. September 25, 2007 Dr. S. Krishnan Head, Information Division National Chemical Laboratory Pune 411008, INDIA Dedicated to Mother Earth who nurtures life, my parents who brought me in to this world, my teachers who taught me to understand nature, and my daughter who I believe would continue to care for life«« Acknowledgements Biodiversity informatics is a passion for me.
    [Show full text]
  • A New Phylogeny of the Cephalaspidea (Gastropoda: Heterobranchia) Based on Expanded Taxon Sampling and Gene Markers Q ⇑ Trond R
    Molecular Phylogenetics and Evolution 89 (2015) 130–150 Contents lists available at ScienceDirect Molecular Phylogenetics and Evolution journal homepage: www.elsevier.com/locate/ympev A new phylogeny of the Cephalaspidea (Gastropoda: Heterobranchia) based on expanded taxon sampling and gene markers q ⇑ Trond R. Oskars a, , Philippe Bouchet b, Manuel António E. Malaquias a a Phylogenetic Systematics and Evolution Research Group, Section of Taxonomy and Evolution, Department of Natural History, University Museum of Bergen, University of Bergen, PB 7800, 5020 Bergen, Norway b Muséum National d’Histoire Naturelle, UMR 7205, ISyEB, 55 rue de Buffon, F-75231 Paris cedex 05, France article info abstract Article history: The Cephalaspidea is a diverse marine clade of euthyneuran gastropods with many groups still known Received 28 November 2014 largely from shells or scant anatomical data. The definition of the group and the relationships between Revised 14 March 2015 members has been hampered by the difficulty of establishing sound synapomorphies, but the advent Accepted 8 April 2015 of molecular phylogenetics is helping to change significantly this situation. Yet, because of limited taxon Available online 24 April 2015 sampling and few genetic markers employed in previous studies, many questions about the sister rela- tionships and monophyletic status of several families remained open. Keywords: In this study 109 species of Cephalaspidea were included covering 100% of traditional family-level Gastropoda diversity (12 families) and 50% of all genera (33 genera). Bayesian and maximum likelihood phylogenet- Euthyneura Bubble snails ics analyses based on two mitochondrial (COI, 16S rRNA) and two nuclear gene markers (28S rRNA and Cephalaspids Histone-3) were used to infer the relationships of Cephalaspidea.
    [Show full text]
  • Cuthona Sp. 1 Baeolidia Japonica Aeolidiella Alba Armina Californica
    Austraeolis stearnsi Hermosita hakunamatata Protaeolidiella atra Phidiana militaris Protaeolidiella juliae Moridilla brockii Noumeaella sp. 4 Cerberilla sp. A Cerberilla sp. C Noumeaella sp. B Facelina sp. A Dermatobranchus semistriatus Cratena peregrina Tritoniella belli Hermissenda crassicornis Facelina bostoniensis Notaeolidia depressa Tethys fimbria Armina neapolitana Flabellina pedata Armina californica Charcotia granulosa Armina sp. 3 Armina sp. 9 Dermatobranchus sp. A Leminda millecra Caloria elegans Pteraeolidia ianthina 1 Anteaeolidiella sp. B 0.88 Anteaeolidiella sp. A 0.67 Anteaeolidiella takanosimensis 0.81 Anteaeolidiella cacaotica 0.82 Anteaeolidiella saldanhensis Anteaeolidiella lurana 1 Pruvotfolia longicirrha Pruvotfolia pselliotes 1 Phidiana hiltoni Phidiana lynceus 1 Limenandra sp. B 1 Limenandra fusiformis 0.74 Limenandra sp. C 0.99 Limenandra sp. A Baeolidia nodosa 1 Armina semperi Armina sp. 0.74 Spurilla sp. A 1 Spurilla braziliana 0.52 Spurilla sargassicola Spurilla neapolitana 1 Aeolidia sp. B 0.99 Aeolidia sp. A Aeolidia papillosa 1 Noumeaella sp. 3 Noumeaella rehderi 0.99 Facelina annulicornis Facelina punctata 0.97 Dermatobranchus sp. 12 0.99 Dermatobranchus sp. 7 0.93 Dermatobranchus sp. 17 Dermatobranchus pustulosus 0.98 Aeolidiella sanguinea Aeolidiella alderi 0.97 Spurilla creutzbergi 0.99 Berghia verrucicornis 0.76 Berghia coerulescens 0.87 Aeolidiella stephanieae 0.99 Berghia rissodominguezi 0.86 Berghia columbina Berghia sp. A 0.97 Hancockia californica 0.99 Hancockia uncinata Hancockia cf. uncinata 0.96 Pruvotfolia sp. A Pruvotfolia sp. B 0.94 Spurilla chromosoma Anteaeolidiella oliviae 0.93 Noumeaella isa Noumeaella sp. A 0.92 Facelina sp. C 0.98 Austraeolis ornata 0.99 Facelinidae sp. A Godiva quadricolor 0.89 Crosslandia daedali Scyllaea pelagica 1 Tritonia sp.
    [Show full text]
  • Terpenoids in Marine Heterobranch Molluscs
    marine drugs Review Terpenoids in Marine Heterobranch Molluscs Conxita Avila Department of Evolutionary Biology, Ecology, and Environmental Sciences, and Biodiversity Research Institute (IrBIO), Faculty of Biology, University of Barcelona, Av. Diagonal 643, 08028 Barcelona, Spain; [email protected] Received: 21 February 2020; Accepted: 11 March 2020; Published: 14 March 2020 Abstract: Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, and steroids. This review evaluates the different kinds of terpenoids found in heterobranchs and reports on their bioactivity. It includes more than 330 metabolites isolated from ca. 70 species of heterobranchs. The monoterpenoids reported may be linear or monocyclic, while sesquiterpenoids may include linear, monocyclic, bicyclic, or tricyclic molecules. Diterpenoids in heterobranchs may include linear, monocyclic, bicyclic, tricyclic, or tetracyclic compounds. Sesterterpenoids, instead, are linear, bicyclic, or tetracyclic. Triterpenoids, tetraterpenoids, and steroids are not as abundant as the previously mentioned types. Within heterobranch molluscs, no terpenoids have been described in this period in tylodinoideans, cephalaspideans, or pteropods, and most terpenoids have been found in nudibranchs, anaspideans, and sacoglossans, with very few compounds in pleurobranchoideans and pulmonates. Monoterpenoids are present mostly in anaspidea, and less abundant in sacoglossa. Nudibranchs are especially rich in sesquiterpenes, which are also present in anaspidea, and in less numbers in sacoglossa and pulmonata. Diterpenoids are also very abundant in nudibranchs, present also in anaspidea, and scarce in pleurobranchoidea, sacoglossa, and pulmonata.
    [Show full text]
  • The Bubble Snails (Gastropoda, Heterobranchia) of Mozambique: an Overlooked Biodiversity Hotspot
    Mar Biodiv DOI 10.1007/s12526-016-0500-7 ORIGINAL PAPER The bubble snails (Gastropoda, Heterobranchia) of Mozambique: an overlooked biodiversity hotspot Yara Tibiriçá1,2 & Manuel António E. Malaquias3 Received: 9 October 2015 /Revised: 14 March 2016 /Accepted: 17 April 2016 # The Author(s) 2016. This article is published with open access at Springerlink.com Abstract This first account, dedicated to the shallow water Keywords Mollusca . Acteonoidea . Cephalaspidea . Sea marine heterobranch gastropods of Mozambique is presented slugs . Taxonomy . Biodiversity . Africa . Western Indian with a focus on the clades Acteonoidea and Cephalaspidea. Ocean Specimens were obtained as a result of sporadic sampling and two dedicated field campaigns between the years of 2012 and 2015, conducted along the northern and southern coasts of Introduction Mozambique. Specimens were collected by hand in the inter- tidal and subtidal reefs by snorkelling or SCUBA diving down The shallow water marine heterobranch gastropods (sea slugs to a depth of 33 m. Thirty-two species were found, of which and alikes) of the Western Indian Ocean (WIO), an area con- 22 are new records to Mozambique and five are new for the fined between the East African coast and the Saya de Malha, Western Indian Ocean. This account raises the total number of Nazareth, and Cargados Carajos banks of the Mascarene shallow water Acteonoidea and Cephalaspidea known in Plateau (Obura 2012), have received little attention when Mozambique to 39 species, which represents approximately compared to other parts of the Indo-West Pacific, and most 50 % of the Indian Ocean diversity and 83 % of the diversity accounts are relatively old with few recent contributions (e.g.
    [Show full text]
  • The Chemistry and Chemical Ecology of Nudibranchs Cite This: Nat
    Natural Product Reports View Article Online REVIEW View Journal | View Issue The chemistry and chemical ecology of nudibranchs Cite this: Nat. Prod. Rep.,2017,34, 1359 Lewis J. Dean and Mich`ele R. Prinsep * Covering: up to the end of February 2017 Nudibranchs have attracted the attention of natural product researchers due to the potential for discovery of bioactive metabolites, in conjunction with the interesting predator-prey chemical ecological interactions that are present. This review covers the literature published on natural products isolated from nudibranchs Received 30th July 2017 up to February 2017 with species arranged taxonomically. Selected examples of metabolites obtained from DOI: 10.1039/c7np00041c nudibranchs across the full range of taxa are discussed, including their origins (dietary or biosynthetic) if rsc.li/npr known and biological activity. Creative Commons Attribution-NonCommercial 3.0 Unported Licence. 1 Introduction 6.5 Flabellinoidea 2 Taxonomy 6.6 Tritonioidea 3 The origin of nudibranch natural products 6.6.1 Tethydidae 4 Scope of review 6.6.2 Tritoniidae 5 Dorid nudibranchs 6.7 Unassigned families 5.1 Bathydoridoidea 6.7.1 Charcotiidae 5.1.1 Bathydorididae 6.7.2 Dotidae This article is licensed under a 5.2 Doridoidea 6.7.3 Proctonotidae 5.2.1 Actinocyclidae 7 Nematocysts and zooxanthellae 5.2.2 Cadlinidae 8 Conclusions 5.2.3 Chromodorididae 9 Conicts of interest Open Access Article. Published on 14 November 2017. Downloaded 9/28/2021 5:17:27 AM. 5.2.4 Discodorididae 10 Acknowledgements 5.2.5 Dorididae 11
    [Show full text]