Cereulide

Cereulide

Names
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
CAS Number	157232-64-9
3D model (Jmol)	Interactive image
ChemSpider	8232646
PubChem	10057089
InChI 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
Chemical formula	C57 H96 N6 O18 (D-Ala-D-O-Leu-L-Val)3
Molar mass	1152
Solubility in water	extremely low
Hazards
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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Infobox references

Cereulide is a toxin produced by Bacillus cereus. 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 a potent cytotoxin that destroys mitochondria. 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 spores of cereulide-producing strains of B. cereus are manyfold more heat resistant than spores of cereulide non-producers. It has no loss of activity upon autoclaving, cooking, or baking.^[1]

In addition to its cytotoxicity, cereulide causes nausea and vomiting. This effect is believed to be caused by its binding and activation of 5-HT₃ receptors, leading to increased afferent vagus nerve stimulation.^[3]

References

1. 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.
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.

External links

• Peltola; et al. (2004). "News on cereulide, the emetic toxin of Bacillus Cereus".
• S. Pitchayawasin; M. Isobe; M. Kuse; T. Franz; N. Agata; M. Ohta (May 19, 2004). "Molecular diversity of cereulide" (PDF). Archived from the original (PDF) on March 13, 2005. Archive.org