AAL Toxin TA2CAS# 79367-51-4 |
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| Cas No. | 79367-51-4 | SDF | Download SDF |
| PubChem ID | 102004519 | Appearance | Powder |
| Formula | C25H47NO10 | M.Wt | 521.65 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-[2-[(3R,4R,5S,7S,13R,14S,16S)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy-2-oxoethyl]butanedioic acid | ||
| SMILES | CCC(C)C(C(CC(C)CCCCCC(C(CC(CN)O)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O | ||
| Standard InChIKey | DOFQASYPBACFKP-DHHJSWHASA-N | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | 1. AAL toxins TA and TB are phytotoxins, isolated from corn cultures by aqueous extraction. 2. AAL-toxin has a wide range of phytotoxicity, it has potential as a natural herbicide because several important weeds including jimsonweed, black nightshade, prickly sida and hemp sesbania are quite sensitive, while some crops such as cotton and maize are not affected. |
| Targets | Antifection |
AAL Toxin TA2 Dilution Calculator
AAL Toxin TA2 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.917 mL | 9.585 mL | 19.1699 mL | 38.3399 mL | 47.9249 mL |
| 5 mM | 0.3834 mL | 1.917 mL | 3.834 mL | 7.668 mL | 9.585 mL |
| 10 mM | 0.1917 mL | 0.9585 mL | 1.917 mL | 3.834 mL | 4.7925 mL |
| 50 mM | 0.0383 mL | 0.1917 mL | 0.3834 mL | 0.7668 mL | 0.9585 mL |
| 100 mM | 0.0192 mL | 0.0958 mL | 0.1917 mL | 0.3834 mL | 0.4792 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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Critical Role of COI1-Dependent Jasmonate Pathway in AAL toxin induced PCD in Tomato Revealed by Comparative Proteomics.[Pubmed:27324416]
Sci Rep. 2016 Jun 21;6:28451. doi: 10.1038/srep28451.
Alternaria alternata f.sp. Lycopersici AAL Toxin TA2) toxin induces programmed cell death (PCD) in susceptible tomato (Solanum lycopersicum) leaves. Jasmonate (JA) promotes AAL Toxin TA2 induced PCD in a COI1 (coronatine insensitive 1, JA receptor)-dependent manner by enhancement of reactive oxygen species (ROS) production. To further elucidate the underlying mechanisms of this process, we performed a comparative proteomic analysis using tomato jasmonic acid insensitive1 ( jai1), the receptor mutant of JA, and its wild type (WT) after AAL Toxin TA2 treatment with or without JA treatment. A total of 10367 proteins were identified in tomato leaves using isobaric tags for relative and absolute quantitation (iTRAQ) quantitative proteomics approach. 2670 proteins were determined to be differentially expressed in response to AAL toxin and JA. Comparison between AAL Toxin TA2 treated jai1 and its WT revealed the COI1-dependent JA pathway regulated proteins, including pathways related to redox response, ceramide synthesis, JA, ethylene (ET), salicylic acid (SA) and abscisic acid (ABA) signaling. Autophagy, PCD and DNA damage related proteins were also identified. Our data suggest that COI1-dependent JA pathway enhances AAL Toxin TA2 induced PCD through regulating the redox status of the leaves, other phytohormone pathways and/or important PCD components.
Nonhost resistance of Arabidopsis thaliana against Alternaria alternata involves both pre- and postinvasive defenses but is collapsed by AAL-toxin in the absence of LOH2.[Pubmed:23360532]
Phytopathology. 2013 Jul;103(7):733-40.
The tomato pathotype of Alternaria alternata causes Alternaria stem canker on tomato depending upon the production of the host-specific AAL-toxin. Host defense mechanisms to A. alternata, however, are largely unknown. Here, we elucidate some of the mechanisms of nonhost resistance to A. alternata using Arabidopsis mutants. Wild-type Arabidopsis showed either no symptoms or a hypersensitive reaction (HR) when inoculated with both strains of AAL-toxin-producing and non-producing A. alternata. Yet, when these Arabidopsis penetration (pen) mutants, pen2 and pen3, were challenged with both strains of A. alternata, fungal penetration was possible. However, further fungal development and conidiation were limited on these pen mutants by postinvasion defense with HR-like cell death. Meanwhile, only AAL-toxin-producing A. alternata could invade lag one homologue (loh)2 mutants, which have a defect in the AAL Toxin TA2 resistance gene, subsequently allowing the fungus to complete its life cycle. Thus, the nonhost resistance of Arabidopsis thaliana to A. alternata consists of multilayered defense systems that include pre-invasion resistance via PEN2 and PEN3 and postinvasion resistance. However, our study also indicates that the pathogen is able to completely overcome the multilayered nonhost resistance if the plant is sensitive to the AAL Toxin TA2, which is an effector of the toxin-dependent necrotrophic pathogen A. alternata.
Biological activities of synthetic analogues of Alternaria alternata toxin (AAL-toxin) and fumonisin in plant and mammalian cell cultures.[Pubmed:8590636]
Phytochemistry. 1995 Dec;40(6):1681-9.
In a search for an analogue of AAL Toxin TA2 with high phytotoxicity and low mammalian toxicity, aminopentols [(AP1), hexacetyl AP1 and N-acetyl AP1], and nine analogues (1-9), were tested for toxicity to duckweed (Lemna pausicostata), susceptible tomato (asc/asc) leaf discs, black nightshade leaf discs and mammalian cell lines, including dog kidney (MDCK), rat liver hepatoma (H4TG) and mouse fibroblasts (NIH3T3). These were compared with AAL Toxin TA2 and fumonisin B1 (FB1). Analogue 9 at 10 microM increased cellular leakage and chlorophyll loss from both tomato and black nightshade leaf discs. The diester 9 was the most active in the duckweed bioassay, but it was much less toxic to MDCK and H4TG cells with an IC50 of 200 microM compared to 10 microM for FB1. Analogue 9 and FB1 showed similar low toxicities (IC50 = 150 microM) to NIH3T3 cells. Among the substances tested, only analogue 9 had significant phytotoxicity and low mammalian toxicity, indicating some potential for development of safe and effective natural herbicides.
Susceptibility of Phelipanche and Orobanche species to AAL-toxin.[Pubmed:19705146]
Planta. 2009 Oct;230(5):1047-55.
Fusarium and Alternaria spp. are phytopathogenic fungi which are known to be virulent on broomrapes and to produce sphinganine-analog mycotoxins (SAMs). AAL Toxin TA2 is a SAM produced by Alternaria alternata which causes the inhibition of sphinganine N-acyltransferase, a key enzyme in sphingolipid biosynthesis, leading to accumulation of sphingoid bases. These long chain bases (LCBs) are determinant in the occurrence of programmed cell death (PCD) in susceptible plants. We showed that broomrapes are sensitive to AAL Toxin TA2, which is not common plant behavior, and that AAL-toxin triggers cell death at the apex of the radicle as well as LCB accumulation and DNA laddering. We also demonstrated that three Lag1 homologs, encoding components of sphinganine N-acyltransferase in yeast, are present in the Orobanche cumana genome and two of them are mutated leading to an enhanced susceptibility to AAL Toxin TA2. We therefore propose a model for the molecular mechanism governing broomrape susceptibility to the fungus Alternaria alternata.
