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Tenuazonic acid

BVT-0463-M001 1 mg $40.00
BVT-0463-M005 5 mg $140.00
BVT-0463-M010 10 mg $250.00
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Product Data
Synonyms 3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one; 3-Acetyl-5-sec-butyltetramic acid; Vivotoxin; AAC-toxin
Properties
Formula C10H15NO3
MW 197.2
Merck Index 14: 9149
CAS 610-88-8
RTECS UY7425000
Source/Host Chemicals Isolated from Alternaria alternate.
Purity ≥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.
Origin Manufactured by BioViotica.
InChi Key CEIZFXOZIQNICU-XNCJUZBTSA-N
Product Type Chemical
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.
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Product 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

  1. Metabolites of Alternaria tenius auct.: The structure of tenuazonic acid: C.E. Stickings; Biochem. J. 72, 332 (1959)
  2. The biological activity of Tenuazonic acid: H.T. Shigeura & C.N. Gordon;  Biochem.  2, 1132 (1963)
  3. Antiviral activity of Tenuazonic acid: F.A. Miller, et al.; Nature 200, 1338 (1963)
  4. Discovery of inhibitory activity of tenuazonic acid for growth of human adenocarcinoma-1: E.A. Kaczka, et al.; BBRC 14, 54 (1964)
  5. Antitumor, cytotoxic, and antibacterial activities of tenuazonic acid and congeneric tetramic acids: C.O. Gitterman; J. Med. Chem. 8, 483 (1965)
  6. 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)
  7. Microbial metabolites with insecticidal properties: M. Cole & G.N. Rolinson; Appl. Microbiol. 24, 660 (1972)
  8. Crystal structure of copper bis(tenuazonate) monohydrate: A. Dippenaar, et al.; J. Cryst. Mol. Struct. 7, 189 (1977)
  9. Inhibition of mouse skin tumor promotion by tenuazonic acid: M. Antony, et al.; Cancer Lett. 61, 21 (1991)
  10. Spectrometric studies on stability of tenuazonic acid (TeA) solution in organic solvents: M. Combina, et al.; Mycotoxin Res. 14, 54 (1998)
  11. 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)
  12. 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)
  13. Tenuazonic acid: a promising antitubercular principle from Alternaria alternata: V. Sonaimuthu, et al.; Microbiol. Res. 2, 63 (2010)
  14. Inhibition of marine biofouling by bacterial quorum sensing inhibitors: S. Dobretsov, et al.; Biofouling 27, 893 (2011)
  15. In vivo assessment of effect of phytotoxin tenuazonic acid on PSII reaction centers: S. Chen, et al.; Plant Physiol. Biochem. 84, 10 (2014)
  16. Mycotoxins from Alternaria: toxicological implications: C. Dall'Asta, et al.; Adv. Mol. Toxicol. 8, 107 (2014)
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