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T8019

Sigma-Aldrich

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

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About This Item

Formule empirique (notation de Hill):
C22H30N4O4
Numéro CAS:
28540-82-1
Poids moléculaire :
414.50
Numéro MDL:
MFCD00133844
Code UNSPSC :
12352200
ID de substance PubChem :
24900492
Nomenclature NACRES :
NA.56

Source biologique

fungus (Alternaria tenuis)

Niveau de qualité

200

Pureté

≥95% (HPLC)

Température de stockage

2-8°C

Chaîne SMILES 

CC(C)CC1NC(=O)C(C)N(C)C(=O)CNC(=O)\C(=C/c2ccccc2)N(C)C1=O

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

Clé InChI

SIIRBDOFKDACOK-LFXZBHHUSA-N

Description générale

Tentoxin is a majorly occurring cyclic tetrapeptide mycotoxin that is excreted by the Alternaria fungal species like Alternaria alternata and Alternaria tenuis.

Actions biochimiques/physiologiques

It induces chlorosis in germinating seedlings of many dicotyledonous plants. Tentoxin has been postulated to inhibit cyclic photophosphorylation by acting as an energy transfer inhibitor at the terminal steps of ATP synthesis and to target the F1 moiety of photosynthetic H+-ATPases. A kinetic analysis of the action of tentoxin on the chloroplast F1 H+-ATPase (CF1) portion of chloroplast ATP synthase has been reported.
Tentoxin is phytotoxic, which induces chlorosis in plant leaves and germinating seedlings. It also halts photophosphorylation by inhibiting chloroplastic ATP synthase. Tentoxin over energizes thylakoids and is converted to isotentoxin by UV irradiation.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide.
C J Arntzen
Biochimica et biophysica acta, 283(3), 539-542 (1972-12-14)
C Sigalat et al.
FEBS letters, 368(2), 253-256 (1995-07-17)
The effect of tentoxin at high concentrations was investigated in thylakoids and proteoliposomes containing bacteriorhodopsin and CF0CF1. Venturicidin-sensitive ATP hydrolysis, ATP-generated delta pH and ATP synthesis were practically 100% inhibited at 2 microM tentoxin, and restored to various extents beyond
Feng He et al.
Biochemistry, 47(2), 836-844 (2007-12-21)
Two highly conserved amino acid residues, an arginine and a glutamine, located near the C-terminal end of the gamma subunit, form a "catch" by hydrogen bonding with residues in an anionic loop on one of the three catalytic beta subunits
J Santolini et al.
The Journal of biological chemistry, 274(2), 849-858 (1999-01-05)
The mechanism of action of tentoxin on the soluble part (chloroplast F1 H+-ATPase; CF1) of chloroplast ATP synthase was analyzed in the light of new kinetic and equilibrium experiments. Investigations were done regarding the functional state of the enzyme (activation
Stephen O Duke et al.
Toxins, 3(8), 1038-1064 (2011-11-10)
Some of the most potent phytotoxins are synthesized by microbes. A few of these share molecular target sites with some synthetic herbicides, but many microbial toxins have unique target sites with potential for exploitation by the herbicide industry. Compounds from
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