Dysidenin

Last updated
Dysidenin
Dysidenin Structure.png
Names
Systematic IUPAC name
(2S,4S)-5,5,5-Trichloro-4-methyl-N-[(1S)-1-(1,3-thiazol-2-yl)ethyl]-2-[(3S)-4,4,4-trichloro-N,3-dimethylbutanamido]pentanamide
Other names
Dysidenine;Pentanamide, 5,5,5-trichloro-4-methyl-2-(methyl(4,4,4-trichloro-3-methyl-1-oxobutyl)amino)-N-(1-(2-thiazolyl)ethyl)-;(2S,4S)-5,5,5-Trichloro-4-methyl-2-[methyl[(S)-4,4,4-trichloro-3-methyl-1-oxobutyl]amino]-N-[(S)-1-(2-thiazolyl)ethyl]pentanamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C17H23Cl6N3O2S/c1-9(16(18,19)20)7-12(14(28)25-11(3)15-24-5-6-29-15)26(4)13(27)8-10(2)17(21,22)23/h5-6,9-12H,7-8H2,1-4H3,(H,25,28)/t9-,10-,11-,12-/m0/s1
    Key: BFVRAKVNXYQMID-BJDJZHNGSA-N
  • InChI=1/C17H23Cl6N3O2S/c1-9(16(18,19)20)7-12(14(28)25-11(3)15-24-5-6-29-15)26(4)13(27)8-10(2)17(21,22)23/h5-6,9-12H,7-8H2,1-4H3,(H,25,28)/t9-,10-,11-,12-/m0/s1
    Key: BFVRAKVNXYQMID-BJDJZHNGBV
  • C[C@@H](C[C@@H](C(=O)N[C@@H](C)C1=NC=CS1)N(C)C(=O)C[C@H](C)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
Properties
C17H23Cl6N3O2S
Molar mass 546.166
AppearanceFine white crystalline powder
Melting point 98 °C (208 °F; 371 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dysidenin is an alkaloid toxin found in the marine sponge Lamellodysidea herbacea (previously known as Dysidea herbacea) [1] which has a lethal effect on certain fish species and other marine organisms. The toxic mechanism of dysidenin is linked to its ability to inhibit iodide transport in thyroid cells. [2] Dysidenin was originally isolated in 1977. [3]

There is a regional variation in the metabolites produced by L. herbacea, as evidenced by the isolation of dysidenin from organism samples obtained from the Great Barrier Reef, while it was absent in samples from the Caroline Islands. [4] This variation has been attributed to different strains of the cyanobacterium Hormoscilla spongeliae that are hosted by different morphological variations of the sponge. [5] [6]

References

  1. ↑ "WoRMS - World Register of Marine Species - Dysidea herbacea (Keller, 1889)". www.marinespecies.org. Retrieved 2025-09-22.
  2. ↑ Van Sande, J; Deneubourg, F; Beauwens, R; Braekman, JC; Daloze, D; Dumont, JE (April 1990). "Inhibition of iodide transport in thyroid cells by dysidenin, a marine toxin, and some of its analogs". Molecular Pharmacology. 37 (4): 583–9. doi:10.1016/S0026-895X(25)10846-8. PMID   2157965.
  3. ↑ Kazlauskas, R.; Lidgard, R.O.; Wells, R.J.; Vetter, W. (January 1977). "A novel hexachloro-metabolite from the sponge dysidea herbacea". Tetrahedron Letters. 18 (36): 3183–3186. doi:10.1016/S0040-4039(01)83192-0.
  4. ↑ Scheuer, Paul J., ed. (1978). Marine Natural Products: Chemical and Biological Perspectives. Vol. 2. Oxford: Elsevier Science. p. 370. ISBN   9780323151863.
  5. ↑ Thacker, R. W.; Starnes, S. (April 2003). "Host specificity of the symbiotic cyanobacterium Oscillatoria spongeliae in marine sponges, Dysidea spp". Marine Biology. 142 (4): 643–648. doi:10.1007/s00227-002-0971-x. ISSN   0025-3162.
  6. ↑ Ridley, Christian P.; Bergquist, Patricia R.; Harper, Mary Kay; Faulkner, D. John; Hooper, John N.A.; Haygood, Margo G. (March 2005). "Speciation and Biosynthetic Variation in Four Dictyoceratid Sponges and Their Cyanobacterial Symbiont, Oscillatoria spongeliae". Chemistry & Biology. 12 (3): 397–406. doi:10.1016/j.chembiol.2005.02.003.
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