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Tenuazonic acid

CAS# 610-88-8

Tenuazonic acid

Catalog No. BCN1859----Order now to get a substantial discount!

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Quality Control of Tenuazonic acid

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Chemical structure

Tenuazonic acid

3D structure

Chemical Properties of Tenuazonic acid

Cas No. 610-88-8 SDF Download SDF
PubChem ID 54683011 Appearance Powder
Formula C10H15NO3 M.Wt 197.23
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-4-acetyl-2-[(2S)-butan-2-yl]-3-hydroxy-1,2-dihydropyrrol-5-one
SMILES CCC(C)C1C(=C(C(=O)N1)C(=O)C)O
Standard InChIKey CEIZFXOZIQNICU-XNCJUZBTSA-N
Standard InChI InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Tenuazonic acid

Description1. Tenuazonic acid, an active component in the A. alternata toxin. 2. Tenuazonic acid exhibits a strong inhibition in photosystem II (PSII) activity. 3. Tenuazonic acid causes cell necrosis of host-plants by oxidative damage from chloroplast-mediated ROS eruption, and enhances the plant's resistances against rose aphids.
TargetsATPase | ROS

Tenuazonic acid Dilution Calculator

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Tenuazonic acid Molarity Calculator

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Preparing Stock Solutions of Tenuazonic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.0702 mL 25.3511 mL 50.7022 mL 101.4045 mL 126.7556 mL
5 mM 1.014 mL 5.0702 mL 10.1404 mL 20.2809 mL 25.3511 mL
10 mM 0.507 mL 2.5351 mL 5.0702 mL 10.1404 mL 12.6756 mL
50 mM 0.1014 mL 0.507 mL 1.014 mL 2.0281 mL 2.5351 mL
100 mM 0.0507 mL 0.2535 mL 0.507 mL 1.014 mL 1.2676 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Tenuazonic acid

Chloroplastic oxidative burst induced by tenuazonic acid, a natural photosynthesis inhibitor, triggers cell necrosis in Eupatorium adenophorum Spreng.[Pubmed:20026008]

Biochim Biophys Acta. 2010 Mar;1797(3):391-405.

Tenuazonic acid (TeA), a nonhost-specific phytotoxin produced by Alternaria alternata, was determined to be a novel natural photosynthesis inhibitor owning several action sites in chloroplasts. To further elucidate the mode of its action, studies were conducted to assess the production and involvement of reactive oxygen species (ROS) in the toxic activity of TeA. A series of experiments indicated that TeA treatment can induce chloroplast-derived ROS generation including not only (1)O(2) but also superoxide radical, H(2)O(2) and hydroxyl radicals in Eupatorium adenophorum mesophyll cells, resulting from electron leakage and charge recombination in PSII as well as thylakoid overenergization due to inhibition of the PSII electron transport beyond Q(A) and the reduction of end acceptors on the PSI acceptor side and chloroplast ATPase activity. The initial production of TeA-induced ROS was restricted to chloroplasts and accompanied with a certain degree of chloroplast damage. Subsequently, abundant ROS were quickly dispersed throughout whole cell and cellular compartments, causing a series of irreversible cellular harm such as chlorophyll breakdown, lipid peroxidation, plasma membrane rupture, chromatin condensation, DNA cleavage, and organelle disintegration, and finally resulting in rapid cell destruction and leaf necrosis. These results show that TeA causing cell necrosis of host-plants is a result of direct oxidative damage from chloroplast-mediated ROS eruption.

In vivo assessment of effect of phytotoxin tenuazonic acid on PSII reaction centers.[Pubmed:25240106]

Plant Physiol Biochem. 2014 Nov;84:10-21.

Tenuazonic acid (TeA), a phytotoxin produced by the fungus Alternaria alternata isolated from diseased croftonweed (Ageratina adenophora), exhibits a strong inhibition in photosystem II (PSII) activity. In vivo chlorophyll fluorescence transients of the host plant croftonweed, show that the dominant effect of TeA is not on the primary photochemical reaction but on the biochemical reaction after QA. The most important action site of TeA is the QB site on the PSII electron-acceptor side, blocking electron transport beyond QA(-) by occupying the QB site in the D1 protein. However, TeA does not affect the antenna pigments, the energy transfer from antenna pigment molecules to reaction centers (RCs), and the oxygen-evolving complex (OEC) at the donor side of PSII. TeA severely inactivated PSII RCs. The fraction of non-QA reducing centers and non-QB reducing centers show a time- and concentration-dependent linear increase. Conversely, the amount of active QA or QB reducing centers declined sharply in a linear way. The fraction of non-QB reducing centers calculated from data of fluorescence transients is close to the number of PSII RCs with their QB site filled by TeA. An increase of the step-J level (VJ) in the OJIP fluorescence transients attributed to QA(-) accumulation due to TeA bound to the QB site is a typical characteristic response of the plants leaf with respect to TeA penetration.

Determination of tenuazonic acid in human urine by means of a stable isotope dilution assay.[Pubmed:23397093]

Anal Bioanal Chem. 2013 May;405(12):4149-58.

The content of Tenuazonic acid in human urine was determined by a stable isotope dilution assay (SIDA) that was recently developed for the analysis of food commodities and extensively re-validated for urine matrix in this study. Linearity of the response curve was proven between molar ratios n(labeled standard)/n(analyte) of 0.02-100. The limits of detection and determination were 0.2 and 0.6 mug/L, respectively. The mean recovery of the stable isotope dilution assay was 102 +/- 3 % in the range between 1.0 and 100 mug/L. Interassay precision was 6.7 % (relative standard deviation of three triplicate analyses of a human urine sample during 3 weeks). The method was applied to two studies dealing with urinary excretion of Tenuazonic acid: In the first study, Tenuazonic acid was quantified in the 24-h urine of six volunteers from Germany (three female, three male) in a concentration range of 1.3-17.3 mug/L or 2.3-10.3 ng/mg(-1) creatinine, respectively. In the second study, two volunteers (one female, one male) ingested 30 mug Tenuazonic acid by consumption of naturally contaminated whole meal sorghum infant cereals and tomato juice, respectively. The urinary excretion of the ingested Tenuazonic acid was 54-81 % after 6 h, depending on matrix and volunteer. After 24 h, 87-93 % of the ingested amount of Tenuazonic acid was excreted, but the fate of the remaining about 10 % is open. Thus, it is not possible to exclude potential health hazards for the consumer, completely.

Alternaria toxin-induced resistance in rose plants against rose aphid (Macrosiphum rosivorum): effect of tenuazonic acid.[Pubmed:25845360]

J Zhejiang Univ Sci B. 2015 Apr;16(4):264-74.

Many different types of toxins are produced by the fungus, Alternaria alternata (Fr.) Keissler. Little is known, however, regarding the influence of these toxins on insects. In this study, we investigated the toxin-induced inhibitory effects of the toxin produced by A. alternata on the rose aphid, Macrosiphum rosivorum, when the toxin was applied to leaves of the rose, Rosa chinensis. The results demonstrated that the purified crude toxin was non-harmful to rose plants and rose aphids, but had an intensive inhibitory effect on the multiplication of aphids. The inhibitory index against rose aphids reached 87.99% when rose plants were sprayed with the toxin solution at a low concentration. Further results from bioassays with aphids and high performance liquid chromatography (HPLC) analyses demonstrated that Tenuazonic acid (TeA) was one of the most important resistance-related active components in the crude toxin. The content of TeA was 0.1199% in the crude toxin under the HPLC method. Similar to the crude toxin, the inhibitory index of pure TeA reached 83.60% 15 d after the rose plants were sprayed with pure TeA solution at the lower concentration of 0.060 mug/ml, while the contents of residual TeA on the surface and in the inner portion of the rose plants were only 0.04 and 0.00 ng/g fresh weight of TeA-treated rose twigs, respectively, 7 d after the treatment. Our results show that TeA, an active component in the A. alternata toxin, can induce the indirect plant-mediated responses in rose plants to intensively enhance the plant's resistances against rose aphids, and the results are very helpful to understand the plant-mediated interaction between fungi and insects on their shared host plants.

Description

Tenuazonic acid, belonging to tetramic acids that are the largest family of natural products, is a putative nonhost-selective mycotoxin isolated from Alternaria alternate. Tenuazonic acid blocks electron transport beyond primary quinone acceptor (QA) by interacting with D1 protein and it is a broad-spectrum and effective photosystem II (PSII) inhibitor.

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