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Tentoxin

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Tentoxin
Chemical structure of tentoxin
Chemical structure of tentoxin
Names
IUPAC name Cyclo(N-methyl-L-alanyl-L-leucyl-alpha,beta-didehydro-N-methylphenylalanylglycyl)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1Key: SIIRBDOFKDACOK-LFXZBHHUSA-N
  • InChI=1/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1Key: SIIRBDOFKDACOK-LFXZBHHUBW
SMILES
  • O=C1N(C(=O)N(/C(C(=O)NCC(=O)N(C)1C)=C\c2ccccc2)C)CC(C)C
Properties
Chemical formula C22H30N4O4
Molar mass 414.498 g/mol
Melting point 172 to 175 °C (342 to 347 °F; 445 to 448 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Tentoxin is a natural cyclic tetrapeptide produced by phytopathogenic fungus Alternaria alternata. It selectively induces chlorosis in several germinating seedling plants. Therefore, tentoxin may be used as a potential natural herbicide, and is a lactam.

Tentoxin was first isolated from Alternaria alternata (syn. tenuis) and characterized by George Templeton et al. in 1967.

Tentoxin has also been used in recent research to eliminate the polyphenol oxidase (PPO) activity from seedlings of higher plants.

References

  1. PubChem. "Tentoxin". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-09-25.
  2. Templeton, G. E., C. 1. Grable, N. D. Fulton, W. L. Meyer. 1967. Tentoxin from Alternaria tenuis: its isolation and characterization. Proceedings of the Mycotoxin Research Seminar, Washington, D. C., June 8–9, 1967. United States Department of Agriculture. pp. 27-29
  3. Duke, S.O. & Vaughn, K.C. 1982. Lack of involvement of polyphenol oxidase in ortho-hydroxylation of phenolic compounds in mung bean seedlings. Physiol. Plant. 54: 381-385.
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