2-Hydroxymelatonin
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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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- CAS. Nr.: 229018-17-1
- Formel: C13H16N2O3
- Molecular Weight:248.28
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Speicherung:
Store at room temperature, keep dry and cool.
In solvent -80°C, 1 year , -20°C, 6 months
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Biologische Aktivität
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Chemical Information
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- Verweise
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Help & FAQs
Biologische Aktivität
2-Hydroxymelatonin (50-150 μM; 15 days) exerts the optimal effect on alleviating cadmium toxicity in cucumber seedlings at a concentration of 100 μM. It promotes seedling growth, increases photosynthetic and gas exchange parameters, antioxidant enzyme activities, polyamine levels, and the expression of the CS-ERS gene, while reducing cadmium uptake and the levels of oxidative stress markers[1].
2-Hydroxymelatonin (5-20 μM; 40 h) potently promotes the germination of non-dormant and dormant seeds of Arabidopsis thaliana (L.) Heynh. Columbia-0 wild type, with the germination rate increased to 80% and 40%, respectively, after treatment with 20 μM for 40 h[3].
2-Hydroxymelatonin (20 μM; 24 h) upregulates the expression of gibberellin (GA) biosynthesis and response genes in non-dormant *Arabidopsis thaliana* (L.) Heynh. Columbia-0 wild-type seeds after 24 h of incubation[3].
2-Hydroxymelatonin (20 μM) promotes the production of superoxide anions (ROS) in non-dormant seeds of Arabidopsis thaliana (L.) Heynh. Columbia-0 wild type, which is confirmed by enhanced NBT staining[3].
2-Hydroxymelatonin (20 μM; 40 h) increases the germination rate of non-dormant Arabidopsis thaliana m2h knockout mutant seeds from 20% to 80%, fully restoring it to the wild-type level after 40 h of incubation[3].
2-Hydroxymelatonin (125-2000 μM; 48 h) potently reduces the viability of Caco2, HCT116, DLD1, and CT26 colorectal cancer cells, with IC50 values of 1010.3 μM, 1482.3 μM, 2136.5 μM, and 1036.1 μM, respectively[5].
2-Hydroxymelatonin (1000 μM; 24 h) induces significant apoptosis and nuclear pyknosis in Caco2 colorectal cancer cells[5].
2-Hydroxymelatonin (50-100 μM; 24 h) inhibits the invasive ability of Caco2 colorectal cancer cells[5].
2-Hydroxymelatonin (50-100 μM; 24 h) inhibits the invasive ability of Caco2 colorectal cancer cells by downregulating the mRNA expression of EMT markers (Snail, Twist, N-cadherin) and the Wnt pathway marker β-catenin[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:human colorectal cancer Caco2, HCT116, DLD1 cells; mouse colorectal cancer CT26 cells
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Concentration:125 μM, 250 μM, 500 μM, 1000 μM, 2000 μM
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Incubation Time:48 h
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Result:Reduced cell viability across all four cell lines, with stronger cytotoxicity than melatonin at high concentrations (1000 or 2000 μM) in HCT116, DLD1, and CT26 cells.
Reduced CT26 cell viability by 90% at 2000 μM.
Exhibited stronger cytotoxicity in Caco2 cells at intermediate concentrations (250 or 500 μM).
Had significantly lower IC50 values than melatonin in all cell lines: 1010.3 μM for Caco2, 1482.3 μM for HCT116, 2136.5 μM for DLD1, and 1036.1 μM for CT26.
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Cell Line:human colorectal cancer Caco2 cells
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Concentration:1000 μM
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Incubation Time:24 h
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Result:Resulted in significantly more Caco2 cells with condensed or fragmented nuclei compared to melatonin-treated and ethanol control cells.\nResulted in a large population of Caco2 cells that were both Annexin V-FITC- and PI-positive, with 61.65% late apoptotic cells and only 34.12% live cells, which was a significantly higher apoptotic rate than in melatonin-treated and ethanol control cells.
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Cell Line:human colorectal cancer Caco2 cells
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Concentration:50 μM, 100 μM
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Incubation Time:24 h
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Result:Reduced the number of invaded Caco2 cells compared to the ethanol control group.
Inhibited invasion by 25% more at 50 μM than at 100 μM, with an inhibitory effect comparable to that of melatonin at equivalent sub-lethal concentrations.
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Cell Line:human colorectal cancer Caco2 cells
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Concentration:50 μM, 100 μM
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Incubation Time:24 h
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Result:Significantly downregulated the mRNA levels of Snail, Twist, N-cadherin, and β-catenin in Caco2 cells at 50 μM.
Downregulated the mRNA levels of Snail, Twist, N-cadherin, and β-catenin in Caco2 cells at 100 μM but to a lesser extent.
Caused no significant effect on E-cadherin mRNA levels with either concentration.
Chemical Information
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CAS. Nr. 229018-17-1
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Appearance Solid
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Molecular Weight 248.28
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Formel C13H16N2O3
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SMILES
CC(NCCC1=C(O)NC2=C1C=C(OC)C=C2)=O
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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
Store at room temperature, keep dry and cool
In solvent -80°C 1 year -20°C 6 months
Reinheit & Dokumentation
Verweise
[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]
[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]
Calculators
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
2-Hydroxymelatonin Related Classifications
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