Table 3.
Summarized information about the discovery of families of alkaloids that can be found in dendrobatoids. Extended information about the conditions employed for the structure elucidation and the availability of their chromatograms, mass spectra and mass spectra fragments could be found in Online Resource 1
| Alkaloid type | Alkaloids detected | Quantity of Alkaloid | Analytic technique | Ref |
|---|---|---|---|---|
| Batrachotoxins | BTX, BTXa, pBTX, hBTX | 28 mg hBTX, 43 mg BTX + pBTX + BTXa, 39 mg BTXa | HR-MS, NMR, UV, X-ray crystallography | (Tokuyama et al. 1968) |
| Batrachotoxins | BTX, BTXa, BTXb, BTXc | 30 mg | NMR, IR, HR-MS | (Daly et al. 1965) |
| Batrachotoxins | BTX, hBTX, BTXa, DQH (195B) | 500 ug BTX, 300 ug hBTX, | HRMS, GC–MS | (Myers et al. 1978) |
| Batrachotoxins | BTX, BTXa, pBTX, hBTX | 20 ug BTX, 10 ug hBTX, 20 ug pBTX, 30 ug BTXa per skin | TLC, MS(EI), MS(CI), MS(quantitative), GC–MS, GC-FID | (Myers and Daly 1976a) |
| Histrionicotoxins | HTX 283, isodihydroHTX 285, neodihydrohistrionicotoxin 285, allodihydrohistrionicotoxin 285, isotetradihydrohistrionicotoxin 287, tetrahydrohistrionicotoxin 287, octahydrohistrionicotoxin 291, HTX-D 287, HTX-267, HTX-259, HTX-239, Others: 219–1, 219–2, 223, 231, 235, 237, 239 243, 259, 283, 323 (maybe PTX-B) | 190 ug HTX 283, 290 ug isodihydroHTX 285, < 15 ug neodihydrohistrionicotoxin 285, > 15 ug allodihydrohistrionicotoxin 285, < 10 ug isotetradihydrohistrionicotoxin 287, < 5 ug tetrahydrohistrionicotoxin 287, < 10 ug octahydrohistrionicotoxin 291, 40 ug HTX-D 287, < 5 ug HTX-267, < 5 ug HTX-259, < 5 ug HTX-239 per skin | TLC, MS(EI), MS(CI), MS(quantitative), GC–MS, GC-FID | (Myers and Daly 1976a) |
| Histrionicotoxins | HTX, dihydroisohistrionicotoxin | 53 mg HTX, 7 mg dihydroisohistrionicotoxin and 49 mg of other alkaloids | X-ray crystallography | (Daly et al. 1971) |
| Pumiliotoxins | PTXa (307A, 307A”), PTXb (323A), DQH (195B) | 80 ug PTXa, 120 ug PTXb, 0–70 ug PTXc per skin | TLC, MS(EI), MS(CI), MS(quantitative), GC–MS, GC-FID | (Myers and Daly 1976a) |
| Gephyrotoxins | GTX (called HTX-D) | Not reported | HR-MS, NMR | (Tokuyama et al. 1974) |
| Gephyrotoxins | Gephyrotoxin and dehydrogephyrotoxin | Not reported | NMR, HR-MS, X-ray crystallography | (Daly et al. 1977) |
| Pumiliotoxins | PTXa (307A, 307A”), PTXb (323A) | 1.5 mg PTXa, 1.5 mg PTXb | UV, NMR, IR, HR-MS | (Myers and Daly 1976b) |
| Pumiliotoxins | PTX 251D, PTX 307A, PTX 323A | Not reported | X-ray crystallography, NMR | (Daly and Myers 1967) |
| Pumiliotoxins | PTX 251D, PTX 307A’, PTX 307A” PTX 323A, alloPTX 267A, alloPTX 323B’, alloPTX 323B”, alloPTX 339A, alloPTX 339B | Not reported | NMR, IR | (Daly et al. 1980) |
| Pumiliotoxins | 237A, 253, PTX-B(323-A), an isomer of PTX-B(323-B), 237B, 265 (degradation artifact?), 281A | 115 ug of 237A, 34 ug of 253, 8 ug of 323A, 3 ug of 323B, per 100 mg of skin | MS(CI), MS(EI), GC–MS | (Tokuyama et al. 1984) |
| Allopumiliotoxins | alloPTX 253, alloPTX 267A, alloPTX 297A, alloPTX 323B | Not reported | NMR, HR-MS | (Daly et al. 1980) |
| Homopumiliotoxins | hPTX 223G | 8 mg | HRMS, GC–MS, NMR | (Tokuyama et al. 1987) |
| Decahydroquinolines | DQH (195B) | 17 mg PTXa, 20 mg PTXb, 16 mg PTXc | HR-MS, NMR, X-ray crystallography | (Daly et al. 1969) |
| Pyrrolizidines | 223B, 223H, 237G, 251 K | Not reported | GC–MS(EI), GC–FTIR | (Garraffo et al. 1993) |
| Indolizidines | 223AB, 239AB | Not reported | GC–MS(CI), GC–MS(EI), HR-MS | (Daly et al. 1978) |
| Indolizidines | 223AB | Not reported | GC–MS and NMR of synthetic diastereoisomers | (Spande et al. 1981) |
|
2,5-disubstituted pyrrolidines |
197B | Not reported | GC–MS(CI-NH3), GC–MS(CI-ND3), GC-FID, GC-HRMS, NMR | (Daly et al. 1986) |
| Lehmizidines | 275 | Not reported | GC–MS(CI-NH3), GC–MS(CI-ND3), GC-FID, GC-HRMS, NMR | (Daly et al. 1986) |
| 2,6-disubstituted piperidines | 225B | Not reported | GC–MS(CI-NH3), GC–MS(CI-ND3), GC-FID, GC-HRMS, NMR | (Daly et al. 1986) |
| 2,6-disubstituted piperidines | 241D | Not reported | GC–MS, NMR | (Edwards et al. 1988) |
| Quinolizidines | 195C | Not reported | HR-MS, GC–MS(CI-NH3), GC–MS(EI), GC–FTIR | (Jones and Gorman 1999) |
| Epibatidines | 208/210 Epibatidine | 60 mg | HR-MS, NMR, GC–FTIR | (Spande et al. 1992) |
| Tetrodotoxins | TTX | Not reported | NMR, IR, TLC | (Mosher et al. 1964) |
| Tetrodotoxins | TTX, 4-epiTTX, 4,9-anhydroTTX | Not reported | HPLC-FLD, TLC | (Daly et al. 1994a) |