Dysidenin

Dysidenin is a toxin from the sponge Lamellodysidea herbacea. It has a lethal effect on fishes and some marine organisms. It has been found to inhibit iodide transport in thyroid cells.[1]

Dysidenin
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
  • 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
Appearance Fine colorless needles
Melting point 98°
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Since Metabolites of the sponge exhibit regional variation, it has been isolated from samples from the Great Barrier Reef, while being absent in samples from the Caroline Islands.[2] It was first isolated in 1977.[3]

References
  1. 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. PMID 2157965.
  2. Scheuer, Paul J., ed. (1978). Marine Natural Products V2 Chemical and Biological Perspectives. Oxford: Elsevier Science. p. 370. ISBN 9780323151863.
  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.
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