T8019
Tentoxin from Alternaria tenuis
Naturally occurring phytotoxic cyclic tetrapeptide
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About This Item
Empirical Formula (Hill Notation):
C22H30N4O4
CAS Number:
Molecular Weight:
414.50
NACRES:
NA.56
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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
SMILES string
CC(C)CC1NC(=O)C(C)N(C)C(=O)CNC(=O)\C(=C/c2ccccc2)N(C)C1=O
InChI key
SIIRBDOFKDACOK-LFXZBHHUSA-N
biological source
fungus (Alternaria tenuis)
assay
≥95% (HPLC)
storage temp.
2-8°C
Quality Level
General description
Tentoxin is a majorly occurring cyclic tetrapeptide mycotoxin that is excreted by the Alternaria fungal species like Alternaria alternata and Alternaria tenuis.
Biochem/physiol Actions
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Alternaria mycotoxins in food and feed: an overview
Escriva L, et al.
Journal of Food Quality, 2017 (2017)
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
Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide.
C J Arntzen
Biochimica et biophysica acta, 283(3), 539-542 (1972-12-14)
Cytotoxicity of Extracts from Alternaria alternata against Cultured Tobacco BY-2Cells
OH KB, et al.
Biocontrol Science, 7(2), 127-130 (2002)
Jingfeng Lou et al.
Molecules (Basel, Switzerland), 18(5), 5891-5935 (2013-05-24)
Alternaria is a cosmopolitan fungal genus widely distributing in soil and organic matter. It includes saprophytic, endophytic and pathogenic species. At least 268 metabolites from Alternaria fungi have been reported in the past few decades. They mainly include nitrogen-containing metabolites
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