Tentoxin

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.[1]

Tentoxin
Chemical structure of tentoxin
Names
IUPAC name
Cyclo(N-methyl-L-alanyl-L-leucyl-alpha,beta-didehydro-N-methylphenylalanylglycyl)
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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/s1 checkY
    Key: SIIRBDOFKDACOK-LFXZBHHUSA-N checkY
  • 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/s1
    Key: SIIRBDOFKDACOK-LFXZBHHUBW
  • O=C1N[C@H](C(=O)N(/C(C(=O)NCC(=O)N(C)[C@H]1C)=C\c2ccccc2)C)CC(C)C
Properties
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Tentoxin was first isolated from Alternaria alternata (syn. tenuis) and characterized by George Templeton et al. in 1967.[2]

Tentoxin has also been used in recent research to eliminate the polyphenol oxidase (PPO) activity from seedlings of higher plants.[3]

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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