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Table 1 Summary of alkaloid occurrence by extract

From: Alkaloids from single skins of the Argentinian toad Melanophryniscus rubriventris (ANURA, BUFONIDAE): An unexpected variability in alkaloid profiles and a profusion of new structures

Province

Salta

Salta

Jujuy

Salta

Jujuy

 

Locale

El Nogalar

Huaico Chico

Los Paños

Tablada

El Cucho

 

Alkaloida

Classb

Toad 1

Toad 2

Toad 3

Toad 4

Toad 5

Toad 6

Toad 7

Toad 8

Toad 9

Toad 10

Nc

169A *

Unclass

x

         

1

181F *

Iz

 

x

       

x

2

183C

Unclass

-/x

  

-/x

  

-/x

  

x*/- d

4

193C

Tri

   

x

    

x

x

3

193G

5,6,8-I

    

x*

     

1

193N *

Tri

x

x

x

x

x

x

    

7

193O *

Tri

-/x

  

-/x

  

-/x

  

x/-

4

195G

5,6,8-I

x/-

x/-

x/-

x/-

 

-/x*

 

x/-

  

6

195L

Unclass

        

x*

x*

2

195N *

Iz

     

x

    

1

196

Q

x

x

  

x

x

  

x

x

6

199B *

Unclass

      

x

   

1

203B

Tri

x

x

 

x

  

x

x

  

5

203C *

Iz

 

x

        

1

203D *

Unclass

 

x

        

1

205G

Iz

x*

x*

x*

x*

      

4

205H

Tri

x

x

    

x

x

  

4

205K

Tri

      

x

   

1

205M *

Tri

      

x

   

1

207J

Tri

 

x*

 

x*

x*

x*

    

4

207N

Unclass

-/x*

-/x*

-/x*

     

x*/x*

x*/-

6

207U

Tri

      

x

x

  

2

207X *

Unclass

x

x

x

x

      

4

207Y *

Tri

      

x

x

  

2

207Z *

Tri

      

x

   

1

209B

5,8-I

         

x

1

209N

Iz

    

x

x

    

2

209T *

Unclass

   

-/x

  

x/-

   

2

211P

Iz

     

x*

    

1

211U *

Unclass

  

x

       

1

221Q

5,6,8-I

x

x

 

x

  

x

x

  

5

221R

Iz

x/-

x/x*

x/-

x/-

x/-

 

x/-

   

7

221S

Tri

x*

     

x*

x*

  

3

221Z *

Tri

  

-/x

-/x

    

x/-

x/-

4

221A2 *

Tri

    

x

     

1

221B2 *

Tri

      

x

   

1

223H

3,5-P

x/-

     

x/x

  

x/-

4

223T

Unclass

 

-/x/−/−

-/x/x*/x

-/x/-/x

 

-/x/-/x

  

x*/x/x*/x

x*/x/x*/x

16

223X

5,6,8-I

-/x

     

x/-

   

2

223AB e

3,5-I

-/x

  

x/x

      

3

223E2 *

Unclass

   

x

      

1

225B

Pip

    

x*

x*

    

2

225O *

Unclass

        

x

x

2

225P *

Tri

x

         

1

225Q *

Iz

    

x/-

x/x

    

3

231B

5,6,8-I

  

x

x

      

2

231J

Unclass

      

x

x

  

2

235E

5,6,8-I

      

x*

   

1

235D2 *

Tri

 

x

    

x

   

2

235E2 *

Unclass

       

x

  

1

236

Spiro

   

x

 

x

    

2

237A

PTX

x

x

x

 

x

  

x

x

x

7

237O

Tri

     

x*

x*

x*

  

3

237W *

Unclass

    

.

x

    

1

239D2 *

5,6,8-I

    

x

x

    

2

239E2 *

4,6-Q

   

x

x

x

    

3

239F2 *

Amine

        

x

x

2

241J *

Amine

       

x

  

1

247Q *

Unclass

x

         

1

247R *

Tri

x

x

x

x

 

x

x

x

  

7

247S *

Tri

     

x

    

1

249P

Unclass

x*/x

     

x*/x

x*/x

  

6

249C2 *

Unclass

      

x

   

1

249D2 *

Unclass

       

x

  

1

251D

PTX

x

x

x

x

x

x

x

x

x

x

10

251S

5,6,8-I

      

x*/x/x

-/x/-

  

4

251F2 *

Tri

x/x

         

2

253O

Unclass

  

-/x*

     

x*/-

x*/-

3

253W *

Unclass

x

 

x

x

    

x

x

5

261D

5,8-I

      

x*

x*

  

2

261I *

Unclass

   

x

 

x

x

x

  

4

263U *

Tri

x

x

x

x

x

x

x

x

  

8

263V *

Unclass

      

x

x

  

2

263W *

Tri

      

x

x

  

2

265D2 *

Tri

x

x

 

x

x

x

x

x

  

7

265E2 *

PTX

x

x

x

x

      

4

267R

5,6.8-I

x

x

x

x

x

 

x

   

6

267Z *

Unclass

     

x

   

x

2

267A2 *

Unclass

        

x/x

x/x

4

267B2 *

Unclass

         

x

1

273E *

De-5,8-I

 

x

        

1

275D

De-5,8-I

 

x*

        

1

277B

PTX

   

x

x

 

x

x

x

 

5

277G

PTX

x

x

x

x

      

4

281P *

Unclass

x

         

1

281Q *

5,8-I

 

x/x

        

2

283G *

Iz

x

x

x

x

x

  

x

x

 

7

291G

PTX

x/x

x/x

x/x

x/x

-/x

-/x

  

-/x

 

11

305B

PTX

x

x

x

x

      

4

305I *

PTX

-/x

x/x

x/x

x/x

   

-/x

  

8

307A

PTX

x

x

x

x

   

x

  

5

307E

PTX

x

x

x

x

      

4

307G

PTX

x/x*

x

x

x

x

x

x

x

x

 

10

309A

PTX

x

      

x

  

2

309K *

PTX

x

x

x

x

      

4

321F *

PTX

       

x

  

1

323A

PTX

x

x

x

x

x

x

x

x

x

x

10

337D *

PTX

x

x

x

x

      

4

341A

aPTX

x

x

x

x

x

  

x

x

x

8

348A *

Unclass

        

x

x

2

364A *

Unclass

        

x

 

1

374A *

Unclass

   

x

  

x

x

  

3

379 f

PTX

    

x

 

x

x

  

3

380A *

Unclass

      

x/x

   

2

104 alk.

 

46g

42g

34g

45g

24g

26g

43g

35g

27g

28g

 
  1. a An asterisk after an alkaloid code name indicates an unreported alkaloid, or after an "x" indicates an unreported diastereomer on GC Rt. See Additional file 1 for HRMS data on 19 fragments of the 56 new alkaloids. See Additional file 1 Tables S1-S10 for observed and corrected GC retention times and relevant literature Rt data.
  2. b Abbreviations used: 3,5-P, 3,5-disubstituted pyrrolizidine; 3,5-I, 3,5-disubstituted indolizidine; 5,8-I, 5,8-disubstituted indolizidine; 5,6,8-I, 5,6,8-trisubstituted indolizidine; De-5,8-I, dehydro-5,8-disubstituted indolizidine; Q, quinolizidine; Iz, izidine; 4,6-Q, 4,6-disubstituted quinolizidine; PTX, pumiliotoxin; aPTX, allopumiliotoxin; Spiro, spiropyrrolizidine; Tri, tricyclic; Unclass, unclassified as to structural type.
  3. c Number of occurrences of the coded alkaloid and diastereomers throughout the ten skins.
  4. d Where one or more diastereomers are indicated for a formula, these are listed in the order of increasing Rt on GC.
  5. e The indolizidine of shorter Rt is the 5Z,9Z diastereomer; the indolizidine of the longer Rt is the 5E,9Z diastereomer.
  6. f Alkaloid 323A is occasionally observed at m/z 379 as the dimethylsiloxane, a GC artifact.
  7. g Total number of alkaloids including diastereomers detected in each extract.
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