T8019

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

• Empirical Formula (Hill Notation): C₂₂H₃₀N₄O₄
• CAS Number: 28540-82-1
• Molecular Weight: 414.50
• NACRES: NA.56
• PubChem Substance ID: 24900492
• UNSPSC Code: 12352200
• MDL number: MFCD00133844

Properties

• biological source: fungus (Alternaria tenuis)
• Quality Segment: 200
• assay: ≥95% (HPLC)
• storage temp.: 2-8°C
• SMILES string: 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
• InChI key: SIIRBDOFKDACOK-LFXZBHHUSA-N

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)