DOCSLIB.ORG

Batrachotoxin Alkaloids from Passerine Birds: a Second Toxic Bird Genus (Ifrita Kowaldi) from New Guinea

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Batrachotoxin Alkaloids from Passerine Birds: a Second Toxic Bird Genus (Ifrita Kowaldi) from New Guinea Batrachotoxin alkaloids from passerine birds: A second toxic bird genus (Ifrita kowaldi) from New Guinea J. P. Dumbacher*†, T. F. Spande‡, and J. W. Daly‡ *Molecular Genetics Laboratory, National Zoological Park, Smithsonian Institution, 3001 Connecticut Avenue NW, Washington, DC 20008; and ‡Laboratory of Bioorganic Chemistry, Room 1A-15, Building 8, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892-0820 Contributed by J. W. Daly, July 24, 2000 Batrachotoxins, including many congeners not previously de- scribed, were detected, and relative amounts were measured by using HPLC-mass spectrometry, in five species of New Guinean birds of the genus Pitohui as well as a species of a second toxic bird genus, Ifrita kowaldi. The alkaloids, identified in feathers and skin, were batrachotoxinin-A cis-crotonate (1), an allylically rearranged 16-acetate (2), which can form from 1 by sigmatropic rearrange- ment under basic conditions, batrachotoxinin-A and an isomer (3 -and 3a, respectively), batrachotoxin (4), batrachotoxinin-A 3؅ hydroxypentanoate (5), homobatrachotoxin (6), and mono- and dihydroxylated derivatives of homobatrachotoxin. The highest levels of batrachotoxins were generally present in the contour feathers of belly, breast, or legs in Pitohui dichrous, Pitohui kirho- cephalus, and Ifrita kowaldi. Lesser amounts are found in head, back, tail, and wing feathers. Batrachotoxin (4) and homobatra- chotoxin (6) were found only in feathers and not in skin. The levels of batrachotoxins varied widely for different populations of Pito- hui and Ifrita, a result compatible with the hypothesis that these birds are sequestering toxins from a dietary source. omobatrachotoxin (6) was reported in 1992 to occur in the Hskins and feathers of three passerine bird species in the genus Pitohui (family Pachycephalidae) endemic to New Guinea and considered toxic by New Guineans (1). No defensive toxin had been previously isolated and identified from avian skin or feathers. Homobatrachotoxin is a member of a group of neu- rotoxic steroidal alkaloids, collectively called batrachotoxins, that stabilize the open form of voltage-gated sodium channels in nerve and muscle membranes (2). Previously, batrachotoxins Fig. 1. Batrachotoxins found in feathers and͞or skins of New Guinean ͞ ϭ ϩ were known only from the skins of five neotropical frog species passerine birds. The protonated parent ion (m z [molecular ion 1]) and major fragment ion in chemical ionization mass spectrometry (CIMS) is indi- in the genus Phyllobates (family Dendrobatidae). Batrachotoxins cated in brackets for each structure. occur at high levels in three species of the true poison-dart frogs of western Colombia (Phyllobates terribilis, Phyllobates bicolor, and Phyllobates aurotaenia), while being present only at trace We have now examined feather and skin extracts of Pitohui levels in the two Central American species (Phyllobates vittatus birds by using HPLC-CIMS and have discovered several other and Phyllobates lugubris) (3). In the frogs, batrachotoxin (4), batrachotoxin alkaloids (Fig. 1). Additionally, we examined skin homobatrachotoxin (6), and batrachotoxinin-A (BTX-A; 3) are and feathers from 11 specimens of an unrelated passerine the major alkaloids (for structures, see Fig. 1). Poison-dart frogs, species, Ifrita kowaldi, which New Guineans also report as toxic when raised in captivity, lack batrachotoxins (4) and thus appear (8, 9). In some Ifrita specimens we detected high levels of 6, lesser in the wild to obtain their skin alkaloids from some source, levels of 4, as well as most of the other batrachotoxin alkaloids probably a dietary arthropod. Dendrobatid frogs, when raised in now found in the Pitohui birds. captivity, readily accumulate alkaloids, including BTX-A (3) The amounts and relative proportions of batrachotoxins var- ied widely among different populations of Pitohui and Ifrita, from an alkaloid-containing diet, unchanged into their skin (5, some specimens having none detectable. Such results are com- 6), lending support to such a dietary hypothesis. Previous studies of Pitohui birds by using direct-probe mass spectrometry and TLC with a sensitive colorimetric reagent Abbreviations: CIMS, chemical ionization mass spectrometry; BTX-A, batrachotoxinin-A. revealed only the presence of homobatrachotoxin (6) and, in See commentary on page 12948. 4 some samples, traces of batrachotoxin ( ) (1, 7). The colorimet- †To whom reprint requests should be addressed. E-mail: [email protected]. ric assay using the modified Ehrlich reagent detects only batra- The publication costs of this article were defrayed in part by page charge payment. This chotoxins containing the pyrrole moiety—i.e., 4 and 6. Pharma- article must therefore be hereby marked “advertisement” in accordance with 18 U.S.C. cological assays suggested, however, that some extracts were §1734 solely to indicate this fact. slightly more toxic than homobatrachotoxin levels alone could Article published online before print: Proc. Natl. Acad. Sci. USA, 10.1073͞pnas.200346897. explain (7). Article and publication date are at www.pnas.org͞cgi͞doi͞10.1073͞pnas.200346897 12970–12975 ͉ PNAS ͉ November 21, 2000 ͉ vol. 97 ͉ no. 24 Downloaded by guest on September 24, 2021 patible with the hypothesis that these birds obtain batrachotoxin double bond) and mono- and dihydroxylated derivatives of 6 alkaloids from an environmental source and do not produce were commonly detected at trace to minor levels in feather them de novo. extracts (M ϩ H, m͞z 569 3 400; 585 3 416; 585 3 400; data not shown). In addition, a number of other minor alkaloids, some Materials and Methods undoubtedly artifacts, were characterized; their tentative struc- Field Collection and Preparation of Samples. Pitohui and Ifrita tures will be presented elsewhere. However, the methyl ketal (8) samples were collected from a variety of localities in Papua New of 1 was important in determining the crotonate stereochemistry Guinea (see footnote, Table 1). Ifrita is normally found at higher of 1 and is discussed below. It is probably an artifact of storage altitudes than Pitohui dichrous, so the two species were never of samples in methanol. collected at the same locality. Wet tissues were placed in glass vials with Teflon-lined lids in 95% (vol͞vol) or 100% ethanol, Characterization of BTX-A cis-Crotonate (1). Natural BTX-A (3) (40 and feathers were placed dry in Ziploc bags (S. C. Johnson & ␮gin5␮l of methanol) was converted to a C-20 crotonate with Son). Tissues were stored cold (4°C) whenever possible. Crude a 1:9 mixture of cis and trans-crotonic anhydride by treatment ethanol or methanol extracts were made from each sample. For with excess reagent at room temperature for 18 hr. It had on feather extracts, approximately 30–60 mg of feathers was ex- HPLC-CIMS, a mass spectrum, and retention time on coinjec- tracted with 2.0 ml of methanol in 3-ml vials with Teflon-lined tion identical to a new and often major batrachotoxin analog caps by vigorously shaking for a few minutes. The methanol and found in feathers or skin of Pitohui or Ifrita species that did not two additional 2-ml methanol washes were withdrawn and absorb UV at 260 nm and had a CIMS showing a m͞z 486 3 400 concentrated under a stream of nitrogen to approximately 50 ␮l. fragmentation. A synthetic 20S-epimer of BTX-A, dideuterated A 10-␮l aliquot corresponding to 6–12 mg of feathers was at C-22 (10), was crotonylated as above. The resulting 20S- injected onto the HPLC column as described below. Skin crotonate coeluted on HPLC-MS with 1 as did the starting samples, prepared in the field, were trimmed of feathers (some epimeric C-20 alcohols. The epimeric alcohol and ester pairs had feather stubs remained) and were extracted with 95% ethyl virtually identical mass spectra outside of the effect of the two alcohol. Typically samples representing about 50% of total skin deuterium atoms and thus under our conditions, HPLC-CIMS is from one bird were concentrated to 50 ␮l before analysis (data unable to distinguish C-20 epimers, either of the alcohols or not shown). crotonates. Since HPLC was also evidently not able to separate the 1:9 mixture of cis and trans crotonates expected from 3,we HPLC-MS Analysis. A Hewlett Packard (HP) model 1100 liquid could not establish the crotonate stereochemistry of 1.Inan chromatograph with variable wavelength detector set at 260 nm attempt to prove the structure of another new batrachotoxin, (long-wavelength absorption maximum of the pyrrole moiety of namely the methyl ketal (8)of1, we were able to observe a 1:9 4 and 6) was interfaced with a Finnigan LCQ mass spectrometer ratio of HPLC peaks, evidently isomers, of identical chemical operating in the atmospheric pressure chemical ionization ionization mass spectra (m͞z 500 3 414) resulting when an (APCI) mode. Under these conditions, the batrachotoxin alka- authentic sample of the methyl ketal (7)of3 was crotonylated (18 loids yield a protonated molecular ion and only losses of neutral hr, room temperature). The methyl ketal prepared from 1 moieties are observed (e.g., H2O, HOAc, crotonic acid, or (MeOH, p-toluenesulfonic acid, 4 hr) cochromatographed with substituted pyrrolecarboxylic acids. An HP Zorbax column the minor, leading peak of the mixture of crotonates resulting (SB-C18 column of 4.6 mm ϫ 23 cm, 5-␮m particle size) was used from 7, and consequently 1 has a cis-crotonate moiety. The ketal with a 0.5-ml͞min flow rate of 90:10 A:B 3 1:1 A:B over 30 min, crotonates on mild acid hydrolysis (3 hr, 0.1 M HCl) gave a single ϭ ϭ ͞ 3 where A 1% HOAc in H2O and B 1% HOAc in CH3CN. peak on HPLC with m z 486 400, proving that our HPLC HPLC-grade solvents were used. Typically 10-␮l injections were conditions cannot separate the cis and trans crotonates of 3.
Load more

Recommended publications
  • Article Look but Don't Lick! Find out How These Brightly Colored Frogs
    The Power of Poison Look But Don’t Lick! GRADES K-2 NOTES FOR EDUCATORS Common Core State Standards: W.K-2.2, W.K-2.8 Have students read the article “Look but Don’t Lick!” Have them write notes RI.K-2.1, RI.K-2.2, RI.K-2.4, RI.K-2.7, RI.K-2.10 in the large right-hand margin. For example, they could underline key passages, paraphrase important information, or write down questions that New York State Science Core Curriculum: they have. LE 3.1a Next Generation Science Standards: If it is not possible to create color handouts, use a computer projector to PE 1-LS1-2 display the reading so that students can see the colorful frog photos. You DCI LS1.A: Structure and Function may also have them color their black and white copies to match the actual All organisms have external parts. Different colors. animals use their body parts in different ways to see, hear, grasp objects, protect Ask: themselves, move from place to place, and • What does it mean for an animal to be poisonous? (A: An animal is seek, find, and take in food, water and air. poisonous if its body contains a substance that is harmful or fatal to other Plants also have different parts (roots, animals.) stems, leaves, flowers, fruits) that help • How does being poisonous help the frogs in this article survive? (A: them survive and grow. Predators will not eat an animal that is poisonous to them. The frogs signal that they are poisonous by their bright colors, which warn predators not to eat them.
    [Show full text]
  • Toxic Birds Not of a Feather
    Commentary Avian chemical defense: Toxic birds not of a feather Paul J. Weldon Conservation and Research Center, Smithsonian Institution, 1500 Remount Road, Front Royal, VA 22630 n 1992, Dumbacher et al. (1) substan- Itially altered prevailing views of avian physiology, biochemistry, and chemical ecology with their report of the potent neurotoxin homobatrachotoxinin in feathers and other tissues of several spe- cies of New Guinean passerine birds of the genus Pitohui. Their discovery was signif- icant not only for suggesting a protective mechanism rarely considered for birds (i.e., chemical defense) but for the nature of the compound they discovered, a struc- turally complex alkaloid that binds Naϩ channels and depolarizes electrogenic membranes. Alkaloids in tetrapods gen- erally had been thought to be confined to amphibians, whose skins have long been acknowledged as arsenals of these biolog- Fig. 1. Hornets (Vespa orientalis) attacking a freshly skinned carcass of a laughing dove (Steptopelia ically active compounds (2). Indeed, be- senegalensis)(Left) while ignoring that of a pied kingfisher (Ceryle rudis). This observation prompted H. B. fore its discovery in Pitohui, homobatra- Cott (4) to undertake an extensive investigation of avian chemical defense. [Reproduced with permission chotoxinin, a member of a family of from ref. 4 (Copyright 1947, The Zoological Society of London).] steroidal alkaloids called batrachotoxinins (BTXs), had been found only in skin se- cretions of Central and South American dichrous), the most toxic of the birds they An additional enigma described by poison-dart frogs (Dendrobatidae) of the examined, is aposematic and may be Dumbacher et al. (3) is the profound genus Phyllobates.
    [Show full text]
  • Poison Dart Frogs of the Genus Phyllobates Secrete Lipophilic Alkaloid
    Cloning and Sequence Analysis of the Voltage-Gated Muscle Na + Channel from the Poison Dart Frog Phyllobates aurotaenia . Castano, S. 1, 2 , Frezza, L. 1, Labro, A. 3, Fierro, L. 2, Bezanilla, F. 1, Correa, A.M. 1 1The University of Chicago, Chicago, IL, USA. 1Grupo de Biología Integrativa (BINTE), Escuela de Ciencias Básicas, Facultad de Salud, Universidad del Valle. 3University of Antwerp, Wilrijk, Belgium. Poison dart frogs of the genus Phyllobates secrete lipophilic alkaloid toxins through their skin that were used by Colombian Amerindians to poison the tips of blowdarts. One of the most potent toxins identified is batrachotoxin (BTX) which is an activator of voltage-gated Na+ channels. BTX causes sustained opening of these channels by shifting the voltage-dependent activation to more hyperpolarized potentials and by disabling both fast and slow inactivation. It also alters pore conductance and selectivity. Endogenous Na+ channels of the poison arrow frog have been proposed to be insensitive to lethal amounts of BTX. In this project we aim to identify what confers BTX insensitivity to Na+ channels of the host frog Phyllobates aurotaenia, therefore we cloned its skeletal muscle NaV channel. Total RNA from skeletal muscle of Phyllobates aurotaenia was isolated and cDNA was obtained with degenerate primers. The 1819 amino acids sequence shares 72% sequence identity with the rat Na+ channel NaV1.4, and 73% with that of the snake Thamnophis sirtalis. The TMs are extremely well conserved (87%) with absolute conservation of S4 in all domains. The N-and C- termini as well as the cytoplasmic linkers between domains are more divergent.
    [Show full text]
  • Visual Signaling in Anuran Amphibians
    .. Hödl, W. and Amezquita, A. (2001). Visual signaling in anuran amphibians. In: Anuran communication, (M.J. Ryan, ed.). .. Smithsonian lust. Press, Washington. Pp. 121-141. 10 WALTER HÖDL AND ADOLFO AMEZQUITA Visual Signaling in Anuran Amphibians lntroduction cation. social behavior, or natural history. visual signaling was either not considered or was treated as a minor subject Acoustic communication plays a fundamental role in an- (Wells 1977a, 1977b; Arak 1983; Duellman and Trueb 1986; uran reproduction and thus is involved in evolutionary Rand 1988; Halliday and Tejedo 1995; Stebbins and Cohen processes such as mate recognition. reproductive isolation. 1995; Sullivan et al. 1995). The most detailed review ofthe speciation. and character displacement (Wells 1977a. 1977b. subject is now more than 20 years old (Wells 1977b). Never- 1988;Rand 1988;Gerhardt and Schwartz 1995;Halliday and theless some authors have discussed the possible evolution- Tejedo 1995;Sullivan et al. 1995).Visual cues. however. have ary link between visual signaling and the reproductive ecol- been thought to function only during dose-range inter- ogy of species, such as reproduction associated with streams actions (Wells 1977c; Duellman and Trueb 1986). Visual sig- (Heyer et aI. 1990; Lindquist and Hetherington 1996. 1998; naling is predicted to be predominantly employed by diur- Hödl et al. 1997;Haddad and Giaretta 1999) or reproduction nal species at sites with an unobstructed view (Endler 1992). within feeding territories (Wells 1977c). Diurnality. however. is not common for the majority offrog Our aim in this review is (1) to propose a dassmcation of species. Thus vocalizations. which are highly efficient for reported behavioral patterns of visual signaling in frags; (2) communicating at night or in dense vegetation, are by far to describe the diversity of visual signals among living an- the best studied anuran signals (Duellman and Trueb 1986; uran taxa; and (3) to apply a comparative approach to explor- Fritzsch et aI.
    [Show full text]
  • A Review of Chemical Defense in Poison Frogs (Dendrobatidae): Ecology, Pharmacokinetics, and Autoresistance
    Chapter 21 A Review of Chemical Defense in Poison Frogs (Dendrobatidae): Ecology, Pharmacokinetics, and Autoresistance Juan C. Santos , Rebecca D. Tarvin , and Lauren A. O’Connell 21.1 Introduction Chemical defense has evolved multiple times in nearly every major group of life, from snakes and insects to bacteria and plants (Mebs 2002 ). However, among land vertebrates, chemical defenses are restricted to a few monophyletic groups (i.e., clades). Most of these are amphibians and snakes, but a few rare origins (e.g., Pitohui birds) have stimulated research on acquired chemical defenses (Dumbacher et al. 1992 ). Selective pressures that lead to defense are usually associated with an organ- ism’s limited ability to escape predation or conspicuous behaviors and phenotypes that increase detectability by predators (e.g., diurnality or mating calls) (Speed and Ruxton 2005 ). Defended organisms frequently evolve warning signals to advertise their defense, a phenomenon known as aposematism (Mappes et al. 2005 ). Warning signals such as conspicuous coloration unambiguously inform predators that there will be a substantial cost if they proceed with attack or consumption of the defended prey (Mappes et al. 2005 ). However, aposematism is likely more complex than the simple pairing of signal and defense, encompassing a series of traits (i.e., the apose- matic syndrome) that alter morphology, physiology, and behavior (Mappes and J. C. Santos (*) Department of Zoology, Biodiversity Research Centre , University of British Columbia , #4200-6270 University Blvd , Vancouver , BC , Canada , V6T 1Z4 e-mail: [email protected] R. D. Tarvin University of Texas at Austin , 2415 Speedway Stop C0990 , Austin , TX 78712 , USA e-mail: [email protected] L.
    [Show full text]
  • WILDLIFE TRADE in AMAZON COUNTRIES: an ANALYSIS of TRADE in CITES-LISTED SPECIES Note by the Executive Secretary 1
    CBD Distr. GENERAL CBD/SBSTTA/21/INF/8 17 November 2017 ENGLISH ONLY SUBSIDIARY BODY ON SCIENTIFIC, TECHNICAL AND TECHNOLOGICAL ADVICE Twenty-first meeting Montreal, Canada, 11-14 December 2017 Item 4 of the provisional agenda* WILDLIFE TRADE IN AMAZON COUNTRIES: AN ANALYSIS OF TRADE IN CITES-LISTED SPECIES Note by the Executive Secretary 1. The Executive Secretary is circulating herewith, for the information of participants in the twenty-first meeting of the Subsidiary Body on Scientific, Technical and Technological Advice, a report presenting a comprehensive overview of international trade in wildlife species listed in the Convention on International Trade in Endangered Species of Wild Fauna and Flora (CITES) in the Amazon countries: Bolivia; Brazil; Colombia; Ecuador; Guyana; Peru; Suriname; and Venezuela. The analysis provides a baseline of information on trade levels and trends in these countries for the 10-year period 2005-2014, in order to inform trade management in the region. It has been produced in close collaboration with national experts, presenting contextual information and insights into the management of wildlife trade in the region. 2. The report is relevant to the work of the Convention on Biological Diversity, in particular with regard to decision XIII/8, paragraph 5(d), in which the Conference of the Parties requests the Executive Secretary, in collaboration with other members of the Collaborative Partnership on Sustainable Wildlife Management, to continue to support efforts by Parties to combat illicit trafficking in wildlife, in line with United Nations General Assembly resolution 69/314 of 30 July 2015, and to enhance institutional capacities on wildlife conservation and law enforcement with relevant law enforcement bodies, such as the International Consortium on Combating Wildlife Crime.
    [Show full text]
  • Taxonomic Checklist of Amphibian Species Listed in the CITES
    CoP17 Doc. 81.1 Annex 5 (English only / Únicamente en inglés / Seulement en anglais) Taxonomic Checklist of Amphibian Species listed in the CITES Appendices and the Annexes of EC Regulation 338/97 Species information extracted from FROST, D. R. (2015) "Amphibian Species of the World, an online Reference" V. 6.0 (as of May 2015) Copyright © 1998-2015, Darrel Frost and TheAmericanMuseum of Natural History. All Rights Reserved. Additional comments included by the Nomenclature Specialist of the CITES Animals Committee (indicated by "NC comment") Reproduction for commercial purposes prohibited. CoP17 Doc. 81.1 Annex 5 - p. 1 Amphibian Species covered by this Checklist listed by listed by CITES EC- as well as Family Species Regulation EC 338/97 Regulation only 338/97 ANURA Aromobatidae Allobates femoralis X Aromobatidae Allobates hodli X Aromobatidae Allobates myersi X Aromobatidae Allobates zaparo X Aromobatidae Anomaloglossus rufulus X Bufonidae Altiphrynoides malcolmi X Bufonidae Altiphrynoides osgoodi X Bufonidae Amietophrynus channingi X Bufonidae Amietophrynus superciliaris X Bufonidae Atelopus zeteki X Bufonidae Incilius periglenes X Bufonidae Nectophrynoides asperginis X Bufonidae Nectophrynoides cryptus X Bufonidae Nectophrynoides frontierei X Bufonidae Nectophrynoides laevis X Bufonidae Nectophrynoides laticeps X Bufonidae Nectophrynoides minutus X Bufonidae Nectophrynoides paulae X Bufonidae Nectophrynoides poyntoni X Bufonidae Nectophrynoides pseudotornieri X Bufonidae Nectophrynoides tornieri X Bufonidae Nectophrynoides vestergaardi
    [Show full text]
  • Silverstone, 1976
    A REVISION OF THE POISON-ARROW FROGS OF THE GENUS PHYLLOBATES BIBRON IN SAGRA (FAMILY DENDROBATIDAE) By PHILIP A. SILVERSTOi'E NATURAL HISTORY M US EU ~ l OF LOS ANGELES COUNTY SCIEl'CE BULLETI!" ~ 7 • :-,:ovEMBER 25. 197b A REVISIO:\, OF THE POISO:\'-ARRO\\' FROGS OF THE GE:\'US PHYUOBATES BIBRO:-': IS SAGRA ( FA ~ lI lY DE:-':DROBATIDAE) A REVISION OF THE POISON-ARROW FROGS OF THE GENUS PHYLLOBATES BIBRON IN SAGRA (FAMILY DENDROBATIDAE) By PHILIP A. SILVERSTONE :-<ATU RAL HISTORY :\1U SElJ~ l OF LOS AV iELES COUI\TY SCIE!\CE BULLETl I\ 17 • :-;OVBlB ER ~5. 1976 T AB LE OF CON TE NTS AC,,"OWLEDGMESTS ~h T U I " LS ""D ~l ET HOOS ~ u-e um abbrevialion$ 3 PNlUJJA< 1a BIB_ ,.,S..u...1841 J Ddinilion J D i a ~ nos i s J Descripelon J Conten t , Tad poles , Specie, group' 7 Life history 7 Food , Summary of distribution 9 Key 10 the genera of Dendrobatidac 9 Key 10 the species of Ph.l'lIoh/ll'-f 9 8 K."OW ~ (ilt 0\Jl' 20 Phylloha tt!_, ,pec ies 20 PhylloM tt!s aurorut!nio 21 Phyllooott!Sbiro /or 2J Phylloha lt!S lugubris 24 Phy/foha tt!s ,';IlOlll.S zs F EMoifAUS (iltOliP 27 PhylJoM u s a'llltwly'; 27 Ph)·fJobou s bol'lt!ngt!ri •• aa Phy/Jobatu t!spino so; 29 Phy/Jobatt!Sjt!mo ralis 50 Phyllobau s tricohv J2 Ph,.llobau s zapar o JJ P O f!S (; 10l/P' as Phyllobatt!s bolMu lllU Phyllooolt!S ingt!r; " Phyllohult' J pan'ulus "J6 Phyllobalt!S peters! J7 Phyllohules plctu s aa Phvltobates pulrhripeclu .f 4J PhyIJob/lles ,marulld;nus 44 T~ lVm A I /JS (; IO\; P Phyllobalt!s bault! ri " Ph.l'lIobalt!s triviuOl,.s " " U TElt U l,IRE CnED 50 FRONTI,PII:n: II.
    [Show full text]
  • Poison Dart Frogs
    POISON DART FROGS Anura Dendrobates tinctorius Family: Dendrobatidae Genus: multiple Range: Southern Central America and north and central South America Habitat: tropical rainforests Niche: Diurnal, terrestrial; breed in trees, carnivorous Wild diet: small invertebrates, particularly ants, which give them their poisonous properties in most cases Zoo diet: pinhead crickets, fruitflies Life Span: (Wild) 3-15 years (Captivity) up to 20 years Sexual dimorphism: Males slightly smaller Location in SF Zoo: South American Tropical Rainforest and Aviary APPEARANCE & PHYSICAL ADAPTATIONS: There are 40 species of Dendrobates poison dart frogs. All have bright coloration (aposematic coloration), which warns predators of their toxic skin secretions (alkaloids obtained from insects they eat). They are small frogs (most are no bigger than a paper clip). They have a good vision used to help capture prey. Their long, sticky tongue darts out and captures their prey once spoted. Each foot contains four toes which each have a flattened tip with a suction cup pad which is used for gripping and clinging to vegetation in its habitat. They lack webbing and are poor swimmers and are found near water but not in it. Weight: < 1 oz (< 28 g) Poison Dart Frogs have no webbing between the toes on their feet, so Length: 1 - 6 cm they are poor swimmers and are not often found in the water. STATUS & CONSERVATION: Many species are threatened by habitat loss and over-collection for the pet trade. COMMUNICATION AND OTHER BEHAVIOR The males are territorial, calling to advertise to females and to defend their area. Calls are species dependent and can be anything from a buzz to trilling whistles.
    [Show full text]
  • Note to Users
    Odors And Ornaments In Crested Auklets (Aethia Cristatella): Signals Of Mate Quality? Item Type Thesis Authors Douglas, Hector D., Iii Download date 24/09/2021 03:31:59 Link to Item http://hdl.handle.net/11122/8905 NOTE TO USERS Page(s) missing in number only; text follows. Page(s) were scanned as received. 61 , 62 , 201 This reproduction is the best copy available. ® UMI Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ODORS AND ORNAMENTS IN CRESTED AUKLETS (AETHIA CRISTATELLA): SIGNALS OF MATE QUALITY ? A DISSERTATION Presented to the Faculty of the University of Alaska Fairbanks in Partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILOSOPHY By Hector D. Douglas III, B.A., B.S., M.S., M.F.A. Fairbanks, Alaska August 2006 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number: 3240323 Copyright 2007 by Douglas, Hector D., Ill All rights reserved. INFORMATION TO USERS The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleed-through, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. ® UMI UMI Microform 3240323 Copyright 2007 by ProQuest Information and Learning Company. All rights reserved.
    [Show full text]
  • First Characterization of Toxic Alkaloids and Volatile Organic Compounds
    Gonzalez et al. Frontiers in Zoology (2021) 18:39 https://doi.org/10.1186/s12983-021-00420-1 RESEARCH Open Access First characterization of toxic alkaloids and volatile organic compounds (VOCs) in the cryptic dendrobatid Silverstoneia punctiventris Mabel Gonzalez1* , Pablo Palacios-Rodriguez2 , Jack Hernandez-Restrepo2 , Marco González-Santoro2 , Adolfo Amézquita2, Andrés E. Brunetti3,4 and Chiara Carazzone1* Abstract Background: Poison frogs are known for the outstanding diversity of alkaloid-based chemical defences with promising therapeutic applications. However, current knowledge about chemical defences in Dendrobatoidea superfamily has two sources of bias. First, cryptic, brown-colored species have been neglected in comparison to those conspicuously colored, and second, there has been little interest in characterizing metabolites other than alkaloids mediating defensive functions. In an effort to contribute to fill the gap of knowledge about cryptic species and broadening the spectrum of compounds analyzed we have applied head-space solid phase microextraction coupled to gas chromatography and mass spectrometry (HS-SPME/GC-MS) for extracting amphibian alkaloids and volatile organic compounds (VOCs) from Silverstoneia punctiventris. Results: Using the skin from 8 specimens in 4 biological replicates we have found 33 different compounds. Twenty of them were classified as VOCs into 15 chemical classes including alkanes, alcohols, carbonyl compounds, methylpyridines, benzothiazoles, N-alkylpyrrolidines, pyrazines, and sesquiterpenoids, some of which were previously reported as repellents, defence compounds or defence pheromones in other organisms, and as sex pheromones in a treefrog. Interestingly, six of the remaining compounds were identified as alkaloids previously reported in other toxic/unpalatable dendrobatid frogs. Conclusions: This is the first report of alkaloids and VOCs found in the Silverstoneia genus, which has been assumed for decades as non-chemically defended.
    [Show full text]
  • BOA5.1-2 Frog Biology, Taxonomy and Biodiversity
    The Biology of Amphibians Agnes Scott College Mark Mandica Executive Director The Amphibian Foundation [email protected] 678 379 TOAD (8623) Phyllomedusidae: Agalychnis annae 5.1-2: Frog Biology, Taxonomy & Biodiversity Part 2, Neobatrachia Hylidae: Dendropsophus ebraccatus CLassification of Order: Anura † Triadobatrachus Ascaphidae Leiopelmatidae Bombinatoridae Alytidae (Discoglossidae) Pipidae Rhynophrynidae Scaphiopopidae Pelodytidae Megophryidae Pelobatidae Heleophrynidae Nasikabatrachidae Sooglossidae Calyptocephalellidae Myobatrachidae Alsodidae Batrachylidae Bufonidae Ceratophryidae Cycloramphidae Hemiphractidae Hylodidae Leptodactylidae Odontophrynidae Rhinodermatidae Telmatobiidae Allophrynidae Centrolenidae Hylidae Dendrobatidae Brachycephalidae Ceuthomantidae Craugastoridae Eleutherodactylidae Strabomantidae Arthroleptidae Hyperoliidae Breviceptidae Hemisotidae Microhylidae Ceratobatrachidae Conrauidae Micrixalidae Nyctibatrachidae Petropedetidae Phrynobatrachidae Ptychadenidae Ranidae Ranixalidae Dicroglossidae Pyxicephalidae Rhacophoridae Mantellidae A B † 3 † † † Actinopterygian Coelacanth, Tetrapodomorpha †Amniota *Gerobatrachus (Ray-fin Fishes) Lungfish (stem-tetrapods) (Reptiles, Mammals)Lepospondyls † (’frogomander’) Eocaecilia GymnophionaKaraurus Caudata Triadobatrachus 2 Anura Sub Orders Super Families (including Apoda Urodela Prosalirus †) 1 Archaeobatrachia A Hyloidea 2 Mesobatrachia B Ranoidea 1 Anura Salientia 3 Neobatrachia Batrachia Lissamphibia *Gerobatrachus may be the sister taxon Salientia Temnospondyls
    [Show full text]