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]
Quick Facts Names, Identifiers ...
Tentoxin
Chemical structure of tentoxin
Names
IUPAC name
Cyclo(N -methyl-L -alanyl-L -leucyl-alpha,beta-didehydro-N -methylphenylalanylglycyl)
Identifiers
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
C22 H30 N4 O4
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).
Close
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]