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T8019

Sigma-Aldrich

Tentoxin from Alternaria tenuis

Naturally occurring phytotoxic cyclic tetrapeptide

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250 μG
$334.00
1 MG
$1,090.00

$334.00

Available to ship onMay 01, 2025Details

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250 μG
$334.00
1 MG
$1,090.00

About This Item

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

$334.00

Available to ship onMay 01, 2025Details

biological source

fungus (Alternaria tenuis)

Quality Level

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

General description

Tentoxin is a majorly occurring cyclic tetrapeptide mycotoxin that is excreted by the Alternaria fungal species like Alternaria alternata and Alternaria tenuis.[1]

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.[2] It also halts photophosphorylation[1] by inhibiting chloroplastic ATP synthase.[2] Tentoxin over energizes thylakoids and is converted to isotentoxin by UV irradiation.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000165435
0000165434
089M4098V
14160612
058M4115V

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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
Cytotoxicity of Extracts from Alternaria alternata against Cultured Tobacco BY-2Cells
OH KB, et al.
Biocontrol Science, 7(2), 127-130 (2002)
Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide.
C J Arntzen
Biochimica et biophysica acta, 283(3), 539-542 (1972-12-14)
Alternaria mycotoxins in food and feed: an overview
Escriva L, et al.
Journal of Food Quality, 2017 (2017)
Jérôme Santolini et al.
Biochemistry, 41(19), 6008-6018 (2002-05-08)
The mechanism of inhibition and reactivation of chloroplast ATP-synthase by the fungal cyclotetrapeptide tentoxin was investigated by photolabeling experiments, binding studies, and kinetic analysis using synthetic analogues of tentoxin. The alpha-subunit of chloroplast F(1)-ATPase (CF(1)) was specifically labeled by a
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