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Merck
모든 사진(1)

문서

T8019

Sigma-Aldrich

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

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About This Item

실험식(Hill 표기법):
C22H30N4O4
CAS Number:
Molecular Weight:
414.50
MDL number:
UNSPSC 코드:
12352200
PubChem Substance ID:
NACRES:
NA.56

생물학적 소스

fungus (Alternaria tenuis)

Quality Level

분석

≥95% (HPLC)

저장 온도

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

일반 설명

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

생화학적/생리학적 작용

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


시험 성적서(COA)

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문서 라이브러리 방문

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
Lionel Perrin et al.
The FEBS journal, 278(12), 2167-2178 (2011-04-27)
We report unambiguous proof of the stability of a carbinol intermediate in the case of P450 metabolism of an N-methylated natural cyclo-peptide, namely tentoxin. Under mild acidic or neutral conditions, the lifetime of carbinol-amide is long enough to be fully

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