Literature DB >> 16195851

Scheloribatid mites as the source of pumiliotoxins in dendrobatid frogs.

Wataru Takada1, Tomoyo Sakata, Satoshi Shimano, Yoshinari Enami, Naoki Mori, Ritsuo Nishida, Yasumasa Kuwahara.   

Abstract

The strawberry poison frog Dendrobates pumilio (Anura: Dendrobatidae) and related poison frogs contain a variety of dendrobatid alkaloids that are considered to be sequestered through the consumption of alkaloid-containing arthropods microsympatrically distributed in the habitat. In addition to ants, beetles, and millipedes, we found that adults of two species of oribatid mites belonging to the cohort Brachypylina, trophically a lower level of animal than ants and beetles, contain dendrobatid alkaloids. Gas chromatography/mass spectrometry (GC/MS) of hexane extracts of adult Scheloribates azumaensis (Oribatida: Acari) revealed the presence of not only pumiliotoxin 251D (8-hydroxy-8-methyl-6-(2'-methylhexylidene)-1-azabicyclo[4.3.0]nonane), but also precoccinelline 193C and another coccinelline-type alkaloid. From the corresponding extracts of an unidentified Scheloribates sp., pumiliotoxin 237A (8-hydroxy-8-methyl-6-(2'-methylpentylidene)-1-azabicyclo[4.3.0]nonane) was detected as a minor component, and identified by synthesis. The presence of related alkaloids, namely deoxypumiliotoxin 193H, a 6,8-diethyl-5-propenylindolizidine, and tentatively, a 1-ethyl-4-pentenynylquinolizidine, were indicated by the GC/MS fragmentation patterns, along with at least another six unidentified alkaloid components. Thus, one possible origin of pumiliotoxins, coccinellid alkaloids, and certain izidines found in poison frogs may be mites of the genus Scheloribates and perhaps related genera in the suborder Oribatida.

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Year:  2005        PMID: 16195851     DOI: 10.1007/s10886-005-7109-9

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  21 in total

1.  Structural elucidation and synthesis of 3-hydroxybenzene-1,2-dicarbaldehyde from astigmatid mites.

Authors:  T Sakata; Y Kuwahara
Journal:  Biosci Biotechnol Biochem       Date:  2001-10       Impact factor: 2.043

2.  Synthesis of alkaloid 223A and a structural revision.

Authors:  Naoki Toyooka; Ayako Fukutome; Hideo Nemoto; John W Daly; Thomas F Spande; H Martin Garraffo; Tetsuo Kaneko
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

3.  Chemistry of the oil gland secretion of Collohmannia gigantea (Acari: Oribatida).

Authors:  G Raspotnig; R Schuster; G Krisper; G Fauler; H J Leis
Journal:  Exp Appl Acarol       Date:  2001       Impact factor: 2.132

4.  Multiple, recurring origins of aposematism and diet specialization in poison frogs.

Authors:  Juan Carlos Santos; Luis A Coloma; David C Cannatella
Journal:  Proc Natl Acad Sci U S A       Date:  2003-10-10       Impact factor: 11.205

5.  Alkaloid 223A: the first trisubstituted indolizidine from dendrobatid frogs.

Authors:  H M Garraffo; P Jain; T F Spande; J W Daly
Journal:  J Nat Prod       Date:  1997-01       Impact factor: 4.050

6.  Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.

Authors:  John W Daly; Tetsuo Kaneko; Jason Wilham; H Martin Garraffo; Thomas F Spande; Alex Espinosa; Maureen A Donnelly
Journal:  Proc Natl Acad Sci U S A       Date:  2002-10-14       Impact factor: 11.205

7.  An uptake system for dietary alkaloids in poison frogs (Dendrobatidae).

Authors:  J W Daly; S I Secunda; H M Garraffo; T F Spande; A Wisnieski; J F Cover
Journal:  Toxicon       Date:  1994-06       Impact factor: 3.033

8.  Occurrence of skin alkaloids in non-dendrobatid frogs from Brazil (Bufonidae), Australia (Myobatrachidae) and Madagascar (Mantellinae).

Authors:  J W Daly; R J Highet; C W Myers
Journal:  Toxicon       Date:  1984       Impact factor: 3.033

9.  Formicine ants: An arthropod source for the pumiliotoxin alkaloids of dendrobatid poison frogs.

Authors:  Ralph A Saporito; H Martin Garraffo; Maureen A Donnelly; Adam L Edwards; John T Longino; John W Daly
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-05       Impact factor: 11.205

10.  Main alkaloids from the Brazilian dendrobatidae frog Epipedobates flavopictus: pumiliotoxin 251D, histrionicotoxin and decahydroquinolines.

Authors:  Márcia Renata Mortari; Elisabeth N Ferroni Schwartz; Carlos Alberto Schwartz; Osmindo Rodrigues Pires; Marcello Moreira Santos; Carlos Bloch; Antonio Sebben
Journal:  Toxicon       Date:  2004-03-01       Impact factor: 3.033

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  24 in total

1.  Taxonomic distribution of defensive alkaloids in Nearctic oribatid mites (Acari, Oribatida).

Authors:  Ralph A Saporito; Roy A Norton; Martin H Garraffo; Thomas F Spande
Journal:  Exp Appl Acarol       Date:  2015-08-12       Impact factor: 2.132

2.  Oribatid mites and skin alkaloids in poison frogs.

Authors:  Günther Raspotnig; Roy A Norton; Michael Heethoff
Journal:  Biol Lett       Date:  2011-02-23       Impact factor: 3.703

3.  Individual variation in alkaloid content of poison frogs of Madagascar (Mantella; Mantellidae).

Authors:  Valerie C Clark; Valérie Rakotomalala; Olga Ramilijaona; Leif Abrell; Brian L Fisher
Journal:  J Chem Ecol       Date:  2006-10       Impact factor: 2.626

4.  Once Again: Oribatid Mites and Skin Alkaloids in Poison Frogs.

Authors:  Michael Heethoff; Roy A Norton; Günther Raspotnig
Journal:  J Chem Ecol       Date:  2016-08       Impact factor: 2.626

5.  Alkaloids in the mite Scheloribates laevigatus: further alkaloids common to oribatid mites and poison frogs.

Authors:  Ralph A Saporito; Roy A Norton; Nirina R Andriamaharavo; Hugo Martin Garraffo; Thomas F Spande
Journal:  J Chem Ecol       Date:  2011-02-12       Impact factor: 2.626

6.  Chemical polymorphism in defense secretions during ontogenetic development of the millipede Niponia nodulosa.

Authors:  Yasumasa Kuwahara; Yayoi Ichiki; Masashi Morita; Tsutomu Tanabe; Yasuhisa Asano
Journal:  J Chem Ecol       Date:  2014-12-20       Impact factor: 2.626

7.  Individual and Geographic Variation of Skin Alkaloids in Three Swamp-Forest Species of Madagascan Poison Frogs (Mantella).

Authors:  Nirina R Andriamaharavo; H Martin Garraffo; Thomas F Spande; Lesley-Ann Giddings; David R Vieites; Miguel Vences; Ralph A Saporito
Journal:  J Chem Ecol       Date:  2015-09-02       Impact factor: 2.626

8.  Indolizidine 239Q and quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus).

Authors:  John W Daly; H Martin Garraffo; Thomas F Spande; Herman J C Yeh; Paola M Peltzer; Pedro M Cacivio; J Diego Baldo; Julián Faivovich
Journal:  Toxicon       Date:  2008-09-20       Impact factor: 3.033

9.  N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).

Authors:  John W Daly; Nathaniel Ware; Ralph A Saporito; Thomas F Spande; H Martin Garraffo
Journal:  J Nat Prod       Date:  2009-06       Impact factor: 4.050

10.  Individual and geographic variation of skin alkaloids in three species of Madagascan poison frogs (Mantella).

Authors:  John W Daly; H Martin Garraffo; Thomas F Spande; Lesley-Ann Giddings; Ralph A Saporito; David R Vieites; Miguel Vences
Journal:  J Chem Ecol       Date:  2008-01-15       Impact factor: 2.626

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