Cereulide

Cereulide is a toxin produced by some strains of Bacillus cereus, Bacillus megaterium and related species. It is a potent cytotoxin that destroys mitochondria. It causes nausea and vomiting.

Cereulide
Names
IUPAC name
cyclo[D-alanyl-N-oxa-L-valyl-L-valyl-N-oxa-D-leucyl-D-alanyl-N-oxa-L-valyl-L-valyl-N-oxa-D-leucyl-D-alanyl-N-oxa-L-valyl-L-valyl-N-oxa-D-leucyl]
Other names
1,7,13,19,25,31-Hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane, cyclic peptide derivate;
Cyclo(D-alanyl-3-methyl-L-2-hydroxybutanoyl-L-valyl-4-methyl-D-2-hydroxypentanoyl-D-alanyl-3-methyl-L-2-hydroxybutanoyl-L-valyl-4-methyl-D-2-hydroxypentanoyl-D-alanyl-3-methyl-L-2-hydroxybutanoyl-L-valyl-4-methyl-D-2-hydroxypentanoyl)
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C57H96N6O18/c1-25(2)22-37-46(64)58-34(19)52(70)79-44(32(15)16)50(68)62-41(29(9)10)56(74)77-39(24-27(5)6)48(66)60-36(21)54(72)81-45(33(17)18)51(69)63-42(30(11)12)57(75)78-38(23-26(3)4)47(65)59-35(20)53(71)80-43(31(13)14)49(67)61-40(28(7)8)55(73)76-37/h25-45H,22-24H2,1-21H3,(H,58,64)(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)/t34-,35-,36-,37-,38-,39-,40+,41+,42+,43+,44+,45+/m1/s1
    Key: JWWAHGUHYLWQCQ-UHZBFKKDSA-N
  • InChI=1/C57H96N6O18/c1-25(2)22-37-46(64)58-34(19)52(70)79-44(32(15)16)50(68)62-41(29(9)10)56(74)77-39(24-27(5)6)48(66)60-36(21)54(72)81-45(33(17)18)51(69)63-42(30(11)12)57(75)78-38(23-26(3)4)47(65)59-35(20)53(71)80-43(31(13)14)49(67)61-40(28(7)8)55(73)76-37/h25-45H,22-24H2,1-21H3,(H,58,64)(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)/t34-,35-,36-,37-,38-,39-,40+,41+,42+,43+,44+,45+/m1/s1
    Key: JWWAHGUHYLWQCQ-UHZBFKKDBT
SMILES
  • O=C1N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H]1C(C)C)C)CC(C)C)C(C)C)C(C)C)C)CC(C)C)C(C)C)C(C)C)C)CC(C)C)C(C)C
Properties
C57 H96 N6 O18
(D-Ala-D-O-Leu-L-Val)3
Molar mass 1152
extremely low
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Neurotoxicant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YN ?)
Infobox references

Cereulide acts as ionophore with a high affinity to potassium cations. Exposure to cereulide causes loss of the membrane potential and uncoupling of oxidative phosphorylation in the mitochondria. The nausea and vomiting is believed to be caused by cereulide's binding and activation of 5-HT3 receptors, leading to increased afferent vagus nerve stimulation.

Cereulide is a cyclic dodecadepsipeptide resembling valinomycin; it contains three repeats of four amino acids: D-Oxy-Leu—D-Ala—L-Oxy-Val—L-Val. It is produced by a dedicated non-ribosomal peptide synthesis (NRPS) system in B. cereus.

The spores of cereulide-producing strains of B. cereus and related species are manyfold more heat resistant than spores of cereulide non-producers. The toxin has no loss of activity upon autoclaving, cooking, or baking.

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