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.

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 Y
    Key: SIIRBDOFKDACOK-LFXZBHHUSA-N Y
  • 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 YN ?)
Infobox references

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.

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