An ETP mycotoxin
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Sporidesmin A

Item No. 46282

Product Insert (PDF)
Technical Information
Formal Name
(3R,5aR,10bS,11R,11aR)-9-chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-3,11a-epidithio-11aH-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-dione
CAS Number
1456-55-9
Synonyms
  • Hydroxysporidesmin B
  • Sporidesmin A
  • NSC 246152
Molecular Formula
C18H20ClN3O6S2
Formula Weight
473.9
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O[C@H]1[C@]23N(C([C@](N(C2=O)C)(SS3)C)=O)[C@]4([H])[C@]1(C5=CC(Cl)=C(OC)C(OC)=C5N4C)O
InChi Code
InChI=1S/C18H20ClN3O6S2/c1-16-14(24)22-13-17(26,12(23)18(22,30-29-16)15(25)21(16)3)7-6-8(19)10(27-4)11(28-5)9(7)20(13)2/h6,12-13,23,26H,1-5H3/t12-,13-,16-,17-,18-/m1/s1
InChi Key
QTONANGUNATZOU-ICTVWZTPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sporidesmin A is an epidithiodioxopiperazine (ETP) mycotoxin that has been found in P. chartarum.1,2 It is the active toxin responsible for facial eczema in livestock, a syndrome characterized by photosensitization, cholestasis, phylloerythrin accumulation in the circulation and tissues, and bile duct stenosis.3,4,1 Sporidesmin A is a substrate for human glutaredoxin 1 (Grx1) in the presence of glutathione (GSH).2 It selectively inactivates human Grx1 over yeast glutathione disulfide (GSSG) reductase, E. coli thioredoxin (Trx), and mammalian thioredoxin reductase (TrxR) at 1 mM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jordan, T.W. The cellular and molecular toxicity of sporidesmin. N. Z. Vet. J. 68(4), 203-213 (2020).

    2. Srinivasan, U., Bala, A., Jao, S.C., et al. Selective inactivation of glutaredoxin by sporidesmin and other epidithiopiperazinediones. Biochemistry 45(29), 8978-8987 (2006).

    3. Percival, J.C., and Thornton, R.H. Sporidesmium Bakeri recorded from Victoria, Australia. Nature 182, 1095 (1958).

    4. Leaver, D.D. Sporidesmin poisoning in the sheep. Res. Vet. Sci. 9(3), 255-264 (1968).