Product name: Avenanthramide A
Synonym name: Avenanthramide 2p;Avenanthramide Bp
Catalogue No.: BP5205
Cas No.: 108605-70-5
Formula: C₁₆H₁₃NO₅
Mol Weight: 299.282
Botanical Source:
Type of Compound: Alkaloids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams
Inquire for bulk scale.

For Reference Standard and R&D, Not for Human Use Directly.

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Avenanthramide A (CAS No.: 108605-70-5) is a unique class of natural phenolic compounds mainly found in oats (Avena sativa ). L.). As a characteristic secondary metabolite in oats, oat anthramide A plays an important role in plant defense mechanisms and has attracted widespread attention in pharmacology due to its multiple biological activities. In recent years, with the deepening development of natural product pharmacology, oatmeal anthramide A has become a research hotspot due to its remarkable antioxidant, anti-inflammatory, and antitumor activities, especially its potential application value in colorectal cancer (CRC) treatment.

This review systematically reviews the chemical structure and physicochemical properties of oat anthamide A, plant origin, and extraction methods, focusing on analyzing its pharmacological activity and mechanism of action, exploring its pharmacokinetic characteristics in combination with druggability parameters, and looking ahead to its clinical application prospects. Its aim is to provide comprehensive references for researchers in natural product pharmacology and new drug development.

Chemical structure and physicochemical properties

Oat anthranamide A belongs to the anthranamide compounds, formed by the formation of phenylpropanoids and aniline structures connected by amide bonds. Its molecular formula is C17H17NO5, and its molecular weight is 299.2820. Structurally, oat anthramide A contains a hydroxyl-modified benzene ring and an aromatic amine group with amide bonds, forming a stable conjugated system that imparts excellent antioxidant activity.

In terms of physicochemical properties, the LogP value of oat anthramide A is 3.1365, indicating moderate lipid solubility, which facilitates cell membrane penetration. Its topological polar surface area (TPSA) is 106.8600, suggesting that the molecule has a certain polarity that helps bind to biological targets. Low water solubility (0.0987 mg/mL) suggests limited solubility in the aqueous phase, which may affect its bioavailability. The blood-brain barrier has low permeability, indicating it mainly acts on peripheral tissues. Importantly, oat anthramide A did not show hERG channel inhibitory activity, and the Ames mutagenic test result was 0.0, indicating high safety and promising drug development potential.

Plant Origins and Extraction Methods

Oat anthrasamide A is mainly found in the seed endosperm and ectoderm of oats, and is a secondary metabolite unique to oats. Its content is significantly influenced by variety, planting environment, maturity, and processing methods. Among common oat varieties, anthrasamide A content is about several hundred micrograms to several milligrams per gram of dry weight.

The extraction method typically uses organic solvent extraction combined with liquid chromatography separation technology. Ethanol or methanol is used as the main extraction solvent, with ultrasound-assisted extraction or hot reflux extraction to improve efficiency. After purification steps such as liquid-liquid distribution and solid-phase extraction, the extract is analyzed qualitatively and quantitatively using high-performance liquid chromatography (HPLC) combined with mass spectrometry (MS) or nuclear magnetic resonance (NMR). In recent years, supercritical CO2 extraction and membrane separation technologies have also been attempted to improve extraction purity and yield.

Pharmacological activity research

Antioxidant and anti-inflammatory activities

Oat anthramide A has significant antioxidant capacity, capable of scavenging free radicals and reducing cell damage caused by oxidative stress. By activating the NFE2L2 (nuclear factor 2-related factor 2, NRF2) signaling pathway, it induces the expression of downstream antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1), thereby enhancing the intracellular antioxidant defense system. Multiple in vitro cell models and animal experiments have confirmed that oat anthramide A effectively reduces oxidative damage and protects nerve cells and the cardiovascular system.

Additionally, oat anthramide A demonstrates good anti-inflammatory activity by inhibiting pro-inflammatory factor expression and the NF-κB signaling pathway. This dual antioxidant and anti-inflammatory action lays the foundation for its application in chronic inflammation-related diseases.

Antitumor activity

Oat anthramide A exhibits significant cytotoxicity in colorectal cancer (CRC) cells. Its mechanism involves targeting RNA heliase DDX3, leading to mitochondrial swelling and increased reactive oxygen species (ROS) production, which in turn induce apoptosis. DDX3, as a multifunctional RNA helisase, plays a key role in tumor cell proliferation, migration, and transcriptional regulation. Oat anthramide A achieves anti-tumor effects by regulating this target.

In vivo mouse model studies show that orally administered oatmeal anthramide A significantly inhibits tumor growth without obvious toxic side effects, indicating good efficacy and safety. This discovery provides a theoretical basis for developing natural anti-cancer drugs based on oatanthamide A.

Mechanism of action and molecular targets

The main mechanisms of action of oat anthramide A include the following aspects:

1. Activate the NFE2L2/NRF2 signaling pathway
   Oat anthramide A enhances cellular resistance to oxidative stress by promoting the translocation of NRF2 from the cytoplasm to the nucleus, binding to antioxidant response elements (ARE), and upregulating the expression of antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1.

2. Targeting RNA helicase DDX3
   DDX3 plays an important role in RNA metabolism and tumor cell survival. Oat anthranamide A binds DDX3, inhibiting its function, leading to loss of mitochondrial membrane potential, mitochondrial swelling, increased ROS production, and induce apoptosis of CRC cells.

3. Regulates apoptosis-related signaling pathways
   By activating mitochondrial pathways, it promotes the release of cytochrome C, activates caspase family proteins, and ultimately triggers programmed cell death.

4. Anti-inflammatory pathway regulation
   Inhibits the NF-κB signaling pathway, reduces the expression of pro-inflammatory cytokines (such as TNF-α, IL-6), and alleviates chronic inflammatory states.

Overall, oat anthramide A exhibits its complex and effective pharmacological activity through multi-target and multi-pathway synergistic effects.

Druggability evaluation and pharmacokinetics

The druggability parameters of oat anthramide A indicate that it has certain potential for drug development. The molecular weight is 299.2820, meeting the basic requirements of Lipinski's rules for oral active drugs. A LogP value of 3.1365 indicates moderate lipid solubility, which facilitates cell membrane permeability, but low water solubility (0.0987 mg/mL) may limit oral bioavailability, requiring formulation optimization to improve leaching.

The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects. The hERG channel was inhibited negatively and the Ames test showed no mutagenicity, indicating good safety.

Currently, pharmacokinetic research on oat anthramide A is relatively limited. Oral administration experiments in mice have shown that it has oral activity, can be absorbed by the body, and exert its efficacy. In the future, systematic in vivo absorption, distribution, metabolism, and excretion (ADME) studies are needed to clarify its half-life, metabolic pathways, and potential drug interactions, providing data support for clinical translation.

Prospects and outlooks for clinical applications

Based on the significant antioxidant, anti-inflammatory, and antitumor activities of oat anthramide A, it has broad clinical application prospects across various disease fields.

1. Adjuvant therapy for colorectal cancer
   Its mechanism of targeting DDX3 to induce tumor cell apoptosis offers new ideas for CRC treatment. As an orally active natural product, oatmeal anthramide A is expected to serve as an adjunct to chemotherapy, enhancing efficacy and reducing side effects.

2. Chronic inflammatory and oxidative stress-related diseases
   Including cardiovascular diseases, neurodegenerative diseases, and metabolic syndromes, it provides protection by activating the NRF2 pathway, reducing oxidative damage and inflammatory responses.

3. Functional foods and nutritional supplements
   Oat anthranamide A, as a natural ingredient in oats, is suitable for development as a functional food ingredient to promote health and prevent chronic diseases.

Future research should focus on optimizing extraction and purification processes, improving bioavailability, and conducting systematic toxicological evaluations and preclinical efficacy validation. At the same time, by combining modern drug design with nanocarrier technology, it enhances its targeting and stability, promoting the clinical translation of oat anthramide A.

Conclusion

Oat anthrasamide A, as an important natural product in oats, shows great potential in antioxidant, anti-inflammatory, and antitumor fields due to its unique chemical structure and multi-target pharmacological activity. Its discovery of DDX3-targeted induction of apoptosis in colorectal cancer cells provides a new direction for the development of natural anticancer drugs. Druggability evaluations show good safety and oral activity, but water solubility and pharmacokinetic characteristics still require further optimization and in-depth research.

With continuous advances in natural product pharmacology and modern drug development technologies, oatmeal anthramide A is expected to become an important candidate for the treatment and prevention of various diseases, promoting the application of natural products in precision medicine. Future systematic mechanistic research, pharmacokinetic analysis, and preclinical evaluation will lay a solid foundation for clinical translation.