Samandarin

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Samandarin
Samandarin.svg
Identifiers
CAS number 467-51-6 N
ChemSpider 16736008 YesY
ChEBI CHEBI:36324 YesY
Jmol-3D images Image 1
Properties
Molecular formula C19H31NO2
Molar mass 305.45 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Samandarin is the main steroidal alkaloid of the skin glands of the fire salamander (Salamandra salamandra).[1] It is extremely toxic, causing strong muscle convulsions and high blood pressure combined with hyperventilation in vertebrates.[citation needed]

Samandarines[edit]

Samandarines are a class of compounds with chemical structure related to samandarin. They are biologically active, lipid soluble alkaloids that can be isolated from the skin of certain salamanders (Urodela).

Fire salamander (Salamandra salamandra).

Samandarines have been isolated in the toxic principles of the fire salamander and alpine salamanders (Salamandra atra). Samandarines are the major component in the parotoid glands of these salamanders and are more prevalent in the fire salamander. The high toxicity (LD50 of 70 μg in mice) is likely due to potent local anesthetic activity. The toxic secretions from these granular skin glands can serve to protect the amphibian from predators due to their noxious effects on buccal tissue. They may even serve to help protect amphibians from bacterial or protozoan infections.[2]

Nine samandarines have been characterized and their structures determined.[3]

Structures of the nine known Samandarines.

It is common for alkaloids to be sequestered into the skin glands of amphibians unchanged from dietary sources. Many of the dietary origins of toxins in these amphibians are ants, mites, beetles, and millipedes. But evidence that the salamanders synthesize the samandarines, presumably from cholesterol, has recently been provided.[4]

Many steroidal alkaloids from amphibians such as the reticulated poison dart frog (Dendrobates reticulates) figure prominently in research on sodium channel function and as a radioligand in defining local anesthetic, anticonvulsant, and antiarrhymic activity. More research needs to be done with samandarines to determine their potential to impact on biomedical research.

See also[edit]

References[edit]

  1. ^ Schöpf, C.; Koch, K. (1942). "Über Samandaron und Samandaridin, Nebenalkaloide im Gift des Feuer- und Alpensalamanders" [Salamander alkaloids. II. Samandarone and samandaridine, secondary alkaloids in the poison of the fire and alpine salamanders]. Justus Liebigs Annalen der Chemie 552 (1): 37–61. doi:10.1002/jlac.19425520103. 
  2. ^ Smith, B. P.; Tyler, M. J.; Kaneko, T.; Garraffo, H. M.; Spande, T. F.; Daly, J. W. (2002). "Evidence for Biosynthesis of Pseudophrynamine Alkaloids by an Australian Myobatrachid Frog (Pseudophryne) and for Sequestration of Dietary Pumiliotoxins". Journal of Natural Products 65 (4): 439–47. doi:10.1021/np010506a. PMID 11975476. 
  3. ^ Daly, John W.; Spande, Thomas F.; Garraffo, H. Martin (2005). "Alkaloids from Amphibian Skin:  A Tabulation of over Eight-Hundred Compounds". Journal of Natural Products 68 (10): 1556–75. doi:10.1021/np0580560. PMID 16252926. 
  4. ^ Daly, J. W.; Garraffo, H. M.; Pannell, L. K.; Spande, T. F.; Severini, C.; Erspamer, V. (1990). "Alkaloids from Australian Frogs (Myobatrachidae): Pseudophrynamines and Pumiliotoxins". Journal of Natural Products 53 (2): 407–21. doi:10.1021/np50068a020. PMID 2380714. 

Further reading[edit]

  • Shimizu, Yuzuru. (1976). "Synthesis of samandarine-type alkaloids and analogues". The Journal of Organic Chemistry 41 (11): 1930. doi:10.1021/jo00873a009. 
  • Sirotenko, Aleksey A.; Ciavarri, Peter A. (1966). "Some Hydrazones of 5-Phenyl-2,4-thiazolidinedione". Journal of Medicinal Chemistry 9 (4): 642–3. doi:10.1021/jm00322a061. PMID 5968048. 

External links[edit]