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Table 1 Volatile profiles of Silverstoneia punctiventris using HS-SPME/GC-MS. IUPAC nomenclature or amphibian alkaloid name are presented, in addition to chemical class/subclass following Classyfire taxonomy or alkaloid family according to Daly et al. database [10], respectively. The retention time in minutes and peak area of each compound has also been specified for each replicate

From: First characterization of toxic alkaloids and volatile organic compounds (VOCs) in the cryptic dendrobatid Silverstoneia punctiventris

Compound

Class/subclass

Alkaloid family

Rt (min)

Replicate

BF

1

2

3

4

3-methylpentane

Alkanes

2.27

705,879

 

1,124,419

 

nd

3-methylbutan-1-ol

Alcohols and polyols

4.47

372,701

314,028

1,120,769

924,992

D 2

hexanal

Carbonyl compounds

6.05

214,369

319,896

360,387

235,433

D 2

2,4,6-trimethylpyridine

Methylpyridines

11.52

1,075,816

742,879

514,956

1,386,495

nd

2-ethylhexan-1-ol

Fatty alcohols

12.57

926,002

504,742

387,674

353,196

nd

N,N-dimethyl-1-phenylmethanamine

Phenylmethylamines

12.89

1,372,753

718,613

1,524,860

6,240,599

nd

octan-1-ol

Fatty alcohols

13.72

 

166,013

  

R 2

nonanal

Carbonyl compounds

14.65

443,257

1,896,061

1,554,323

1,845,908

nd

1,2-dimethoxybenzene

Methoxybenzenes

15.85

616,333

  

545,145

D 2

nonan-1-ol

Fatty alcohols

16.61

 

193,102

117,130

 

nd

167E

3,5-I

17.43

   

305,129

t B* 1

decanal

Carbonyl compounds

17.63

278,696

700,648

1,604,149

1,134,669

D 2

1,2-benzothiazole

Benzothiazoles

18.25

144,183

74,430

800,979

136,283

nd

Unknown1

 

18.55

   

75,485

–

3,5-dimethyl-2-(2-methylbutyl)pyrazine

Pyrazines

18.61

4,599,780

276,403

322,721

 

DP 1

Unknown2

 

18.92

8,629,722

   

–

Unknown3

 

19.18

31,992,502

 

667,980

 

–

Unknown4

 

19.86

1,087,042

   

–

1,2,2-triethylpyrrolidine

N-alkylpyrrolidines

20.01

  

229,410

 

R 1

Unknown5

 

20.49

 

213,285

  

–

207I

1,4-Q

20.59

511,736

   

B* 1

(3-hydroxy-2,4,4-trimethylpentyl) 2-methylpropanoate

Carboxylic acid derivatives

22.79

463,512

1,601,188

1,534,685

1,913,640

nd

277E

5,6,8-I

23.09

659,662

 

515,089

149,741

B* 1

4-(2,6,6-trimethylcyclohexen-1-yl)butan-2-one

Sesquiterpenoids

24.77

499,394

178,155

394,571

620,594

nd

(E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one

Sesquiterpenoids

26.18

298,444

231,400

597,650

1,081,089

nd

223AB (5E,9Z)

3,5-I

27.08

3,807,696

  

8,685,370

t B* 1

223AB (5E,9E)

3,5-I

27.49

264,366

  

618,971

t B* 1

223AB (5Z,9Z)

3,5-I

27.96

650,603

  

1,623,468

t B* 1

Unknown6

 

28.52

 

536,527

 

556,661

–

tetradecanal

Fatty aldehydes

29.76

 

460,880

  

R 2

Unknown7

 

30.24

443,555

387,061

427,026

783,730

–

N-butyl-N-(2-oxochromen-3-yl)acetamide

Coumarins and derivatives

31.02

864,020

  

2,087,588

nd

3-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one

Sesquiterpenoids

31.34

403,695

212,268

398,450

789,925

nd

  1. Abbreviations: 3,5-I 3,5-Disubstituted indolizidines, 1,4-Q 1,4-disubstituted quinolizidines, 5,6,8-I 5,6,8-Trisubstituted indolizidines, BF Behavioral function, nd not determined, t low toxicity, B* Presumed bitter, D Defence substance, DP Defence pheromone, R Repellent, 1 Defensive/antipredator properties measured in the class/subclass/alkaloid family, not with specific chemical structure, 2 Behavioral test with organisms other than amphibians