Indole-3-acetamide is a biosynthesis intermediate of indole-3-acetic acid[1]. Indole-3-acetamide is formed directly from tryptophan by tryptophan monooxygenase or, indirectly, through indole-3-acetonitrile or indole-3-acetaldoxime intermediates, and converted to indole-3-acetic acid(IAA) by amidase[2]. IAA is the most common natural plant growth hormone of the auxin class, mainly regulating growth and development in plants and microorganisms by binding to the auxin receptor TIR1[3][4]. Indole-3-acetamide is usually used in the fileds of plant growth regulation, biochemistry, intestinal microbiota metabolism[5-7].
In vitro, treatment of HepG2 cells with Indole-3-acetamide (0-600μM) for 12 hours bolstered cell viability, decreased levels of ALT, AST, TC, and TG, reduced ROS production, attenuated EtOH-induced oxidative damage, activated AhR gene and protein expression, and significantly upregulated ADH and ALDH gene expression while downregulating inflammatory gene expression[6].
References:
[1] Lehmann, T., Hoffmann, M., Hentrich, M., & Pollmann, S. (2010). Indole-3-acetamide-dependent auxin biosynthesis: a widely distributed way of indole-3-acetic acid production?. European journal of cell biology, 89(12), 895–905.
[2] Pérez-Alonso, M. M., Ortiz-García, P., Moya-Cuevas, J., Lehmann, T., Sánchez-Parra, B., Björk, R. G., Karim, S., Amirjani, M. R., Aronsson, H., Wilkinson, M. D., & Pollmann, S. (2021). Endogenous indole-3-acetamide levels contribute to the crosstalk between auxin and abscisic acid, and trigger plant stress responses in Arabidopsis. Journal of experimental botany, 72(2), 459–475.
[3] Dimkpa, C. O., Zeng, J., McLean, J. E., Britt, D. W., Zhan, J., & Anderson, A. J. (2012). Production of indole-3-acetic acid via the indole-3-acetamide pathway in the plant-beneficial bacterium Pseudomonas chlororaphis O6 is inhibited by ZnO nanoparticles but enhanced by CuO nanoparticles. Applied and environmental microbiology, 78(5), 1404–1410.
[4] Duca, D. R., & Glick, B. R. (2020). Indole-3-acetic acid biosynthesis and its regulation in plant-associated bacteria. Applied microbiology and biotechnology, 104(20), 8607–8619.
[5] Ortiz-García, P., Pérez-Alonso, M. M., González Ortega-Villaizán, A., Sánchez-Parra, B., Ludwig-Müller, J., Wilkinson, M. D., & Pollmann, S. (2022). The Indole-3-Acetamide-Induced Arabidopsis Transcription Factor MYB74 Decreases Plant Growth and Contributes to the Control of Osmotic Stress Responses. Frontiers in plant science, 13, 928386.
[6] Wang, M., Feng, X., Zhao, Y., Lan, Y., & Xu, H. (2023). Indole-3-acetamide from gut microbiota activated hepatic AhR and mediated the remission effect of Lactiplantibacillus plantarum P101 on alcoholic liver injury in mice. Food & function, 14(23), 10535–10548.
[7] Eguchi, N., Watanabe, Y., Kawanishi, K., Hashimoto, Y., & Hayaishi, O. (1984). Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives. Archives of biochemistry and biophysics, 232(2), 602–609.
Indole-3-acetamide是吲哚-3-乙酸的生物合成中间体[1]。Indole-3-acetamide可以直接由色氨酸通过色氨酸单加氧酶形成，也可以通过吲哚-3-乙腈或吲哚-3-乙醛肟中间体间接形成，并且可以在酰胺酶的作用下转化为吲哚-3-乙酸（IAA）[2]。IAA是最常见的天然植物生长素类激素，主要通过与生长素受体TIR1结合来调节植物和微生物的生长和发育[3][4]。Indole-3-acetamide通常用于植物生长调节、生物化学以及肠道微生物群代谢等领域的研究[5-7]。
在体外实验中，用Indole-3-acetamide（0-600μM）处理HepG2细胞12小时，可以增强细胞活性，降低ALT、AST、TC和TG水平，减少活性氧（ROS）的产生，减轻乙醇诱导的氧化损伤，激活AhR基因和蛋白表达，并显著上调乙醇脱氢酶（ADH）和乙醛脱氢酶（ALDH）基因表达，同时下调炎症基因表达[6]。