Tenuazonic acid

Specifications / Handling

More Information
Product Details
Synonyms	3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one; 3-Acetyl-5-sec-butyltetramic acid; Vivotoxin; AAC-toxin
Product Type	Chemical
Properties
Formula	C₁₀H₁₅NO₃
MW	197.2
Merck Index	14: 9149
CAS	610-88-8
RTECS	UY7425000
Source/Host Chemicals	Isolated from Alternaria alternate.
Purity Chemicals	≥98% (HPLC, NMR)
Appearance	Brownish viscous oil.
Solubility	Soluble in DMSO, methanol, acetone or dichloromethane.
Identity	Determined by ¹H-NMR and MS. The ¹H-NMR in CDCl3 shows a mixture of two tautomers as part of an equilibrium.
Declaration	Manufactured by BioViotica.
InChi Key	CEIZFXOZIQNICU-XNCJUZBTSA-N
Smiles	[H][C@]1(NC(=O)C(C(C)=O)=C1O)[C@@H](C)CC
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	+4°C
Handling Advice	Protect from light.
Use/Stability	Stable for at least 1 year after receipt when stored at +4°C. Store solutions at -20°C in the dark.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Description

Mycotoxin. Tremorgenic toxin.
Exhibits antibacterial, antiviral, insecticidal and antitumor activity.
Phytotoxic agent. New type of photosystem II inhibitor.
Protein synthesis inhibitor in vitro by suppression of the release of newly formed proteins from the ribosomes.
Antitubercular agent. Active against Mycobacteria.
Inhibits TPA-induced ornithine decarboxylase (ODC) activity in mice. Suppressed mouse skin tumor promotion.

Product References

Metabolites of Alternaria tenius auct.: The structure of tenuazonic acid: C.E. Stickings; Biochem. J. 72, 332 (1959)
The biological activity of Tenuazonic acid: H.T. Shigeura & C.N. Gordon; Biochem. 2, 1132 (1963)
Antiviral activity of Tenuazonic acid: F.A. Miller, et al.; Nature 200, 1338 (1963)
Discovery of inhibitory activity of tenuazonic acid for growth of human adenocarcinoma-1: E.A. Kaczka, et al.; BBRC 14, 54 (1964)
Antitumor, cytotoxic, and antibacterial activities of tenuazonic acid and congeneric tetramic acids: C.O. Gitterman; J. Med. Chem. 8, 483 (1965)
Influence of inhibitors of protein synthesis on interferon formation in mice. II. Comparison of effects of glutarimide antibiotics and tenuazonic acid: J.S. Youngner; Virology 40, 335 (1970)
Microbial metabolites with insecticidal properties: M. Cole & G.N. Rolinson; Appl. Microbiol. 24, 660 (1972)
Crystal structure of copper bis(tenuazonate) monohydrate: A. Dippenaar, et al.; J. Cryst. Mol. Struct. 7, 189 (1977)
Inhibition of mouse skin tumor promotion by tenuazonic acid: M. Antony, et al.; Cancer Lett. 61, 21 (1991)
Spectrometric studies on stability of tenuazonic acid (TeA) solution in organic solvents: M. Combina, et al.; Mycotoxin Res. 14, 54 (1998)
Identification of tenuazonic acid as a novel type of natural photosystem II inhibitor binding in QB-site of Chlamydomonas reinhardtii: S. Chen, et al.; Biochim. Biophys. Acta, Bioener. 1767, 306 (2007)
Chloroplastic oxidative burst induced by tenuazonic acid, a natural photosynthesis inhibitor, triggers cell necrosis in Eupatorium adenophorum Spreng: S. Chen, et al.; Biochim. Biophys. Acta, Bioener.1797, 391 (2010)
Tenuazonic acid: a promising antitubercular principle from Alternaria alternata: V. Sonaimuthu, et al.; Microbiol. Res. 2, 63 (2010)
Inhibition of marine biofouling by bacterial quorum sensing inhibitors: S. Dobretsov, et al.; Biofouling 27, 893 (2011)
In vivo assessment of effect of phytotoxin tenuazonic acid on PSII reaction centers: S. Chen, et al.; Plant Physiol. Biochem. 84, 10 (2014)
Mycotoxins from Alternaria: toxicological implications: C. Dall'Asta, et al.; Adv. Mol. Toxicol. 8, 107 (2014)

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