Salamander alkaloids

Fire salamander ( Salamandra salamandra )

The salamander alkaloids are naturally occurring chemical compounds from the group of alkaloids . They are secreted by salamanders, such as the fire salamander ( Salamandra salamandra ) or the alpine salamander ( Salamandra atra ), as defense substances against bacteria and fungi from skin glands .

Representative

The salamander alkaloids are structurally derived from 3- aza- A -homo-5 β -androstane, Neosaman (C ₁₀ H ₃₃ N) is given as the oxygen-free base . The group, which includes about ten representatives, includes samandarine (C ₁₉ H ₃₁ NO ₂ ), its acetylated analogue 16- O -acetylsamandarine and the oxidized compound samandarone (C ₁₉ H ₂₉ NO ₂ , 16-dehydrosamandarin). Furthermore, samanine (without the 1 α , 4 α -epoxy bridge), samandione (C ₁₉ H ₂₉ NO ₂ ), cycloneosamandione (C ₁₉ H ₂₉ NO ₂ ), samandaridine (C ₂₁ H ₃₁ NO ₃ ) and samanderon (C ₂₂ H ₃₁ NO ₂ ) counted among the salamander alkaloids.

• 

  Samandarin

• 

  Samandaridin

biosynthesis

The biogenetic starting substance for the development of the androstane system is cholesterol , while glutamine serves as the nitrogen source for the N atom .

effect

Samandarin shows respiratory-inhibiting effects in humans, leads to high blood pressure , cardiac arrhythmias and haemolysis . It is highly effective as a local anesthetic , but unsuitable for medical applications due to its high toxicity.

literature

• Entry to salamander alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on July 6, 2014.
• Spectrum Online Lexicon of Biochemistry: Salamander Alkaloids
• C. Schöpf, K. Koch: About Samandaron and Samandaridin, secondary alkaloids in the poison of the fire and alpine salamander . In: Justus Liebig's Annals of Chemistry. 1942, 552 (1): 37-61, doi : 10.1002 / jlac.19425520103

Individual evidence

1. ↑ ^{a b c d} C. Schöpf, OW Möller: About Samandarin and related alkaloids, VI. Cycloneosamandion, a new minor alkaloid from the fire salamander (Salamandra maculosa Laur.) . European Journal of Organic Chemistry 1960, 633 (1): 127-156, doi : 10.1002 / jlac. 19606330116
2. ↑ Lou Feierabend: Too stupid for traffic, too clever for the East . In: Welt Online, June 6, 2007, accessed December 29, 2016.
3. ↑ Robert Lücke: From rain mollies and fire newts . In: Naturgucker-Magazin, accessed on December 29, 2016.