Cereulide

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
  • 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
  • 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).
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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 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.[1][2] 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.[3]

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.[4]

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.[1]

  1. ^ a b News on cereulide, the emetic toxin of Bacillus Cereus
  2. ^ M. A. Andersson; R. Mikkola; J. Helin; M. C. Andersson; M. Salkinoja-Salonen (April 1998). "A Novel Sensitive Bioassay for Detection of Bacillus cereus Emetic Toxin and Related Depsipeptide Ionophores". Applied and Environmental Microbiology. 64 (4): 1338–1343. Bibcode:1998ApEnM..64.1338A. doi:10.1128/AEM.64.4.1338-1343.1998. PMC 106152. PMID 9546170.
  3. ^ Agata N, Ohta M, Mori M, Isobe M (1995). "A novel dodecadepsipeptide, cereulide, is an emetic toxin of Bacillus cereus". FEMS Microbiol Lett. 129 (1): 17–20. doi:10.1016/0378-1097(95)00119-P. PMID 7781985.
  4. ^ Alonzo, Diego A.; Magarvey, Nathan A.; Schmeing, T. Martin (2015). "Characterization of Cereulide Synthetase, a Toxin-Producing Macromolecular Machine". PLOS ONE. 10 (6): e0128569. Bibcode:2015PLoSO..1028569A. doi:10.1371/journal.pone.0128569. PMC 4455996. PMID 26042597.