Tenuazonic acid

Tenuazonic acid
Names
	Preferred IUPAC name (5S)-3-Acetyl-5-[(2S)-butan-2-yl]-4-hydroxy-1,5-dihydro-2H-pyrrol-2-one
Identifiers
CAS Number	610-88-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9440;
ChEMBL	ChEMBL511015 ;
ChemSpider	19953674 ;
ECHA InfoCard	100.164.201
PubChem CID	101949;
UNII	Y2J8Y1TO29 ;
CompTox Dashboard (EPA)	DTXSID701017805 ;
	InChI InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1 Key: CEIZFXOZIQNICU-XNCJUZBTSA-N ;
	SMILES O=C1C(C(C)=O)=C(O)[C@@]([C@H](CC)C)([H])N1;
Properties
Chemical formula	C10H15NO3
Molar mass	197.234 g·mol−1
Appearance	White crystalline powder
Acidity (pKa)	3.5
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	* 182 mg kg−1 (Mice, ♂, oral) 225 mg kg−1 (Mice, ♂, oral); 81 mg kg−1 (Mice, ♀, oral);
Pharmacology
Routes of; administration	Ingested or Inhaled
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tenuazonic acid is a mycotoxin produced by Alternaria species.^[3] It is a powerful eukaryotic protein synthesis inhibitor.^[4] It is a tetrameric acid that is ubiquitous in biological environments and prevents the release of newly synthesized protein from the ribosome. Its toxicity is the highest among all Alternaria mycotoxins and has both phytotoxic and cytotoxic properties.^[5] In 1991 Tenuazonic acid was reported to inhibit skin tumor promotion in mice.^[6]

^ ^a ^b Miller, F. A. et al.; Nature, 200 (1963), S. 1338–1339
^ Smith, E. R. et al.; Cancer Chemother. Rep. 52 (1968), S. 579–585.
^ Alisa D. Hocking (Editor), John I. Pitt (Editor) and Robert A. Samson (Editor): Advances in Food Mycology. Springer 2006; ISBN 978-0-387-28385-2; p. 23
^ Dilip K. Arora and Arora K. Arora: Fungal Biotechnology in Agricultural, Food, and Environmental Applications. Marcel Dekker Inc; illustrated edition 2003; ISBN 978-0-8247-4770-1; p. 336
^ Mikula, Hannes; Horkel, Ernst; Hans, Philipp; Hametner, Christian; Fröhlich, Johannes (2013-04-15). "Structure and tautomerism of tenuazonic acid--a synergetic computational and spectroscopic approach". Journal of Hazardous Materials. 250–251: 308–317. Bibcode:2013JHzM..250..308M. doi:10.1016/j.jhazmat.2013.02.006. ISSN 1873-3336. PMID 23474405.
^ Tenuazonic acid page from Fermentek

[Miller1963-1] Miller, F. A. et al.; Nature, 200 (1963), S. 1338–1339

[2] Smith, E. R. et al.; Cancer Chemother. Rep. 52 (1968), S. 579–585.

[3] Alisa D. Hocking (Editor), John I. Pitt (Editor) and Robert A. Samson (Editor): Advances in Food Mycology. Springer 2006; ISBN 978-0-387-28385-2; p. 23

[4] Dilip K. Arora and Arora K. Arora: Fungal Biotechnology in Agricultural, Food, and Environmental Applications. Marcel Dekker Inc; illustrated edition 2003; ISBN 978-0-8247-4770-1; p. 336

[5] Mikula, Hannes; Horkel, Ernst; Hans, Philipp; Hametner, Christian; Fröhlich, Johannes (2013-04-15). "Structure and tautomerism of tenuazonic acid--a synergetic computational and spectroscopic approach". Journal of Hazardous Materials. 250–251: 308–317. Bibcode:2013JHzM..250..308M. doi:10.1016/j.jhazmat.2013.02.006. ISSN 1873-3336. PMID 23474405.

[6] Tenuazonic acid page from Fermentek

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