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 (JSmol)	Interactive image;
ChemSpider	8232646 ;
PubChem CID	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).
	(what is ?)
	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] Cereulide is produced by a dedicated non-ribosomal peptide synthesis (NRPS) system in B. cereus.^[3]

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.^[4]

References

1 2 News on cereulide, the emetic toxin of Bacillus Cereus
↑ 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.
↑ http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0128569
↑ 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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[Heatnews-1] 1 2 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] ttp://journals.plos.org/plosone/article?id=10.1371/journal.pone.0128569

[4] 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.