108605-69-2
Chemical Structure
Avenanthramide B
- CAS No.: 108605-69-2
- Formula:C17H15NO6
- Molecular Weight:329.31
IUPAC Name: (E)-5-hydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)benzoic acid
InChIKey: JXFZHMCSCYADIX-XVNBXDOJSA-N
SMILES: C(O)(=O)C1=C(NC(/C=C/C2=CC(OC)=C(O)C=C2)=O)C=CC(O)=C1
Biological Activity: Avenanthramide B is an oat phytoalexin, a porcine liver esterase inhibitor, and an amyloglucosidase inhibitor, with an IC50 of 4.4 mg/mL against Aspergillus niger amyloglucosidase. Avenanthramide B increases the activation status of Akt1 and the expression level of eNOS, elevates the levels of NO and cGMP, and reduces the level of superoxide anions. Avenanthramide B acts on amyloglucosidase via a competitive mixed mechanism, functions as a fluorescence quencher, and exerts bidirectional regulatory effects on protein thermal stability. Avenanthramide B serves as a substrate for oat leaf peroxidase. Avenanthramide B can be used in research related to type 2 diabetes[1][2][3][4].
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Avenanthramide B | Avenanthramide B is an oat phytoalexin, a porcine liver esterase inhibitor, and an amyloglucosidase inhibitor, with an IC50 of 4.4 mg/mL against Aspergillus niger amyloglucosidase. Avenanthramide B increases the activation status of Akt1 and the expression level of eNOS, elevates the levels of NO and cGMP, and reduces the level of superoxide anions. Avenanthramide B acts on amyloglucosidase via a competitive mixed mechanism, functions as a fluorescence quencher, and exerts bidirectional regulatory effects on protein thermal stability. Avenanthramide B serves as a substrate for oat leaf peroxidase. Avenanthramide B can be used in research related to type 2 diabetes. | |||||||||||||||||||||
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References
- [1]. Lim H, et al. Compared Inhibitory Activities of Tamoxifen and Avenanthramide B on Liver Esterase and Correlation Based on the Superimposed Structure Between Porcine and Human Liver Esterase. International journal of molecular sciences. 2024 Dec 11;25(24):13291. [Content Brief]
- [2]. Serreli G, et al. Ferulic Acid Derivatives and Avenanthramides Modulate Endothelial Function through Maintenance of Nitric Oxide Balance in HUVEC Cells. Nutrients. 2021 Jun 12;13(6):2026. [Content Brief]
- [3]. Feng W, et al. Unraveling the inhibition mechanism of avenanthramides on amyloglucosidase: Probing by multi-spectroscopic techniques, enzyme kinetics, and molecular docking simulations. Food chemistry. 2026 Apr 30;509:148552. [Content Brief]
- [4]. Okazaki Y, et al. New dimeric compounds of avenanthramide phytoalexin in oats. The Journal of organic chemistry. 2007 May 11;72(10):3830-9. [Content Brief]
