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Merck

T8019

Sigma-Aldrich

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

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About This Item

Wzór empiryczny (zapis Hilla):
C22H30N4O4
Numer CAS:
Masa cząsteczkowa:
414.50
Numer MDL:
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
NACRES:
NA.56

pochodzenie biologiczne

fungus (Alternaria tenuis)

Poziom jakości

Próba

≥95% (HPLC)

temp. przechowywania

2-8°C

ciąg 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

Klucz InChI

SIIRBDOFKDACOK-LFXZBHHUSA-N

Opis ogólny

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

Działania biochem./fizjol.

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.
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Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Gloves, type N95 (US)


Certyfikaty analizy (CoA)

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

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
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
Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide.
C J Arntzen
Biochimica et biophysica acta, 283(3), 539-542 (1972-12-14)
Nicolas Loiseau et al.
Biopolymers, 69(3), 363-385 (2003-07-02)
Biologically active cyclic tetrapeptides, usually found among fungi metabolites, exhibit phytotoxic or cytostatic activities that are likely to be governed by specific conformations adopted in solution. For conformational studies and drug design, there is a strong interest in using fast

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