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Thaxtomin A

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Thaxtomin A是一种由Streptomyces scabies等植物病原菌产生的二酮哌嗪类植物毒素。

Thaxtomin A Chemical Structure

Cas No.:122380-18-1

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1mg
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Description

Thaxtomin A is a diketopiperazine phytotoxin produced by plant pathogenic bacteria such as Streptomyces scabies[1-2]. Thaxtomin A disrupts cell wall integrity by inhibiting plant cellulose biosynthesis and induces programmed cell death (PCD) in plant cells. Thaxtomin A can be used in research related to the pathogenic mechanisms of Streptomyces scabiesand the development of novel natural herbicides[3-4].

In vitro, A. thaliana cells were treated with Thaxtomin A (10μM) for 6 hours. Thaxtomin A induced an early, transient Ca²⁺ influx. N. tabacum BY2 cells were treated with Thaxtomin A (20μM) for 6 hours, which did not cause an increase in cytoplasmic Ca²⁺ concentration[5]. A. thaliana cells were treated with Thaxtomin A (2.0–10.0μM) for 24–72 hours. Thaxtomin A caused DNA fragmentation in the nucleus and induced programmed cell death (PCD)[6].

References:
[1] Clarke CR, Kramer CG, Kotha RR, et al. The Phytotoxin Thaxtomin A Is the Primary Virulence Determinant for Scab Disease of Beet, Carrot, and Radish Caused by Streptomyces scabiei. Phytopathology. 2022 Nov;112(11):2288-2295.
[2] Li Y, Liu J, Adekunle D, et al. TxtH is a key component of the thaxtomin biosynthetic machinery in the potato common scab pathogen Streptomyces scabies. Mol Plant Pathol. 2019 Oct;20(10):1379-1393.
[3] Casey C, Köcher T, Champion C, et al. Reduced coenzyme Q synthesis confers non-target site resistance to the herbicide thaxtomin A. PLoS Genet. 2023 Jan 6;19(1):e1010423.
[4] Zhang H, Wang Q, Ning X, et al. Synthesis and biological evaluations of a series of thaxtomin analogues. J Agric Food Chem. 2015 Apr 15;63(14):3734-41.
[5] Meimoun P, Tran D, Baz M, et al. Two different signaling pathways for thaxtomin A-induced cell death in Arabidopsis and tobacco BY2. Plant Signal Behav. 2009 Feb;4(2):142-4.
[6] Duval I, Brochu V, Simard M, et al. Thaxtomin A induces programmed cell death in Arabidopsis thaliana suspension-cultured cells. Planta. 2005 Nov;222(5):820-31.

Thaxtomin A是一种由Streptomyces scabies等植物病原菌产生的二酮哌嗪类植物毒素[1-2]。Thaxtomin A可通过抑制植物纤维素合成来破坏细胞壁完整性,同时通过诱导植物细胞程序性死亡。Thaxtomin A可用于Streptomyces scabies致病机理和新型天然除草剂开发的相关研究[3-4]

在体外,Thaxtomin A(10μM)处理A. thaliana细胞6小时,可诱导一个早期、短暂的Ca²⁺内流。Thaxtomin A(20μM)处理N. tabacum BY2细胞6小时,不会引起胞质Ca²⁺浓的增加[5]。Thaxtomin A(2.0–10.0μM)处理A. thaliana细胞24–72h。Thaxtomin A引起了细胞核DNA片段化,诱导了程序性细胞死亡(PCD)[6]

实验参考方法

Cell experiment [1]:

Cell lines

Arabidopsis thaliana (A. thaliana) suspension-cultured cells; Nicotiana tabacum BY2 suspension-cultured cells.

Preparation Method

Arabidopsis thaliana suspension cells were grown in Gamborg medium (pH=5.8). Nicotiana tabacum BY2 suspension cells were grown in Murashige and Skoog medium (pH=5.8). All experiments were performed using log-phase cells (4 days after sub-culture for Arabidopsis and 6 days for BY2). Arabidopsis treated with Thaxtomin A (10μM) for 6h, BY2 treated with Thaxtomin A (20μM) for 6h.

Reaction Conditions

10 or 20μM; 6h.

Applications

In A. thaliana cells, 10μM Thaxtomin A induces an early, short-lived Ca2+ influx, which is an upstream event in the signaling pathway leading to Thaxtomin A-induced cell death. In BY2 cells, 20μM Thaxtomin A did not induce a significant increase in cytosolic calcium concentration.

References:
[1] Meimoun P, Tran D, Baz M, et al. Two different signaling pathways for thaxtomin A-induced cell death in Arabidopsis and tobacco BY2. Plant Signal Behav. 2009 Feb;4(2):142-4.

化学性质

Cas No. 122380-18-1 SDF
化学名 (3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione
Canonical SMILES O=C(N(C)[C@H]1CC2=CNC3=C2C([N+]([O-])=O)=CC=C3)[C@@](CC4=CC=CC(O)=C4)(O)N(C)C1=O
分子式 C22H22N4O6 分子量 438.4
溶解度 DMF: Soluble,DMSO: Soluble,Ethanol: Partially soluble,Methanol: Partially soluble 储存条件 Store at -20°C
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1 mM 2.281 mL 11.4051 mL 22.8102 mL
5 mM 456.2 μL 2.281 mL 4.562 mL
10 mM 228.1 μL 1.1405 mL 2.281 mL
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