229018-17-1
Chemical Structure
2-Hydroxymelatonin
- CAS No.: 229018-17-1
- Formula:C13H16N2O3
- Molecular Weight:248.28
IUPAC Name: N-(2-(2-hydroxy-5-methoxy-1H-indol-3-yl)ethyl)acetamide
InChIKey: CIEAUFSGHUWAMC-UHFFFAOYSA-N
SMILES: CC(NCCC1=C(O)NC2=C1C=C(OC)C=C2)=O
Biological Activity: 2-Hydroxymelatonin is a major hydroxylated metabolite of Melatonin (HY-B0075). It is enzymatically produced in plants by melatonin 2-hydroxylase (M2H/AsMT), while in animals, it is generated in trace amounts via CYP450 or spontaneous oxidation. 2-Hydroxymelatonin acts as a respiratory burst oxidase homolog (RBOH)-dependent ROS burst inducer, thereby regulating stress tolerance, seed germination and growth in plants. In animal cells, 2-Hydroxymelatonin synergizes with BMP-4 to promote osteogenesis, and exerts pro-apoptotic and anti-metastatic activities against colorectal cancer cells. 2-Hydroxymelatonin can be used in studies related to plant premature senescence, osteoporosis and colorectal cancer[1][2][3][4][5].
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2-Hydroxymelatonin | 2-Hydroxymelatonin is a major hydroxylated metabolite of Melatonin (HY-B0075). It is enzymatically produced in plants by melatonin 2-hydroxylase (M2H/AsMT), while in animals, it is generated in trace amounts via CYP450 or spontaneous oxidation. 2-Hydroxymelatonin acts as a respiratory burst oxidase homolog (RBOH)-dependent ROS burst inducer, thereby regulating stress tolerance, seed germination and growth in plants. In animal cells, 2-Hydroxymelatonin synergizes with BMP-4 to promote osteogenesis, and exerts pro-apoptotic and anti-metastatic activities against colorectal cancer cells. 2-Hydroxymelatonin can be used in studies related to plant premature senescence, osteoporosis and colorectal cancer. | |||||||||||||||||||||
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References
- [1]. Shah AA, et al. 2-Hydroxymelatonin mitigates cadmium stress in cucumis sativus seedlings: Modulation of antioxidant enzymes and polyamines. Chemosphere. 2020 Mar;243:125308. [Content Brief]
- [2]. Lee HY, et al. 2-Hydroxymelatonin, Rather Than Melatonin, Is Responsible for RBOH-Dependent Reactive Oxygen Species Production Leading to Premature Senescence in Plants. Antioxidants (Basel, Switzerland). 2021 Oct 29;10(11):1728. [Content Brief]
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[3]. Lee HY, Back K. 2-Hydroxymelatonin Promotes Seed Germination by Increasing Reactive Oxygen Species Production and Gibberellin Synthesis in Arabidopsis thaliana. Antioxidants (Basel). 2022 Apr 8;11(4):737.
[Content Brief] - [4]. Lee SH, et al. Synergistic stimulating effect of 2-hydroxymelatonin and BMP-4 on osteogenic differentiation in vitro. Biochemical and biophysical research communications. 2020 Jul 05;527(4):941-946. [Content Brief]
- [5]. Yang Y, et al. 2-Hydroxymelatonin, a Predominant Hydroxylated Melatonin Metabolite in Plants, Shows Antitumor Activity against Human Colorectal Cancer Cells. Molecules (Basel, Switzerland). 2017 Mar 14;22(3):453. [Content Brief]
