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Usage

Uses

Used in Pharmaceutical Applications:
Avenanthramide C is used as an antioxidant and anti-inflammatory agent for its potential health benefits. Its antioxidant properties help to neutralize harmful free radicals, while its anti-inflammatory effects can reduce inflammation and oxidative stress in the body.
Used in Cancer Prevention and Treatment:
Avenanthramide C is used as a chemopreventive and therapeutic agent for colonic cancer. It has been shown to reduce and attenuate the proliferation of colonic cancer cells, potentially offering a natural approach to cancer prevention and treatment.
Used in Enzyme Inhibition:
Avenanthramide C is used as an enzyme inhibitor, specifically targeting chymotrypsin and trypsin activities. By inhibiting these enzymes, Avenanthramide C may contribute to the regulation of various physiological processes and help maintain overall health.

Upstream product

• 130514-71-5 2-[(E)-2-(3,4-Dihydroxy-phenyl)-vinyl]-6-hydroxy-benzo[d][1,3]oxazin-4-one 
• 88623-81-8 3,4-diacetoxycinnamic acid 
• 331-39-5 caffeic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 67727-64-4 3,4-diacetoxybenzaldehyde 
• 108-24-7 acetic anhydride 

Relevant academic research and scientific papers

Oat polyphenol avenanthramide-2c confers protection from oxidative stress by regulating the Nrf2-ARE signaling pathway in PC12 cells

Accumulating evidence has demonstrated that cellular antioxidant systems play essential roles in retarding oxidative stress-related diseases, such as Parkinson's disease. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is a chief regulator of c

Synthetic method of oat alkaloids

The invention provides a synthetic method of oat alkaloid and studies a chemical synthesis process of oat alkaloids A, B and C. The oat alkaloids A, B and C are synthesized by taking 2-amino-5-hydroxybenzoic acid, meldrum's acid, 4-hydroxybenzaldehyde, 4-hydroxyl-3-methoxybenzaldehyde and 3,4-dihydroxy benzaldehyde as raw materials and using a Knoevenagel condensation reaction. Analysis means suchas infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectroscopy and elemental analysis are applied to perform structural characterization on a compound, so that the feasibility of a process route of synergizing the oat alkaloids is demonstrated, and the synthetic process conditions are optimized; the synthetic method has important research significance for further developmentof application of oat alkaloids with multiple bioactive functions such as oxidation resistance. The development of the chemical synthesis technology has a very broad application prospect.

Key Phytochemicals Contributing to the Bitter Off-Taste of Oat (Avena sativa L.)

Sensory-directed fractionation of extracts prepared from oat flour (Avena sativa L.) followed by LC-TOF-MS, LC-MS/MS, and 1D/2D-NMR experiments revealed avenanthramides and saponins as the key phytochemicals contributing to the typical astringent and bitter off-taste of oat. Besides avenacosides A and B, two previously unreported bitter-tasting bidesmosidic saponins were identified, namely, 3-(O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→3)-β-d-glucopyranosyl(1→4)]-β-d-glucopyranosid)-26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22,26-triol, and 3-(O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→4)]-β-d-glucopyranosid)-26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22,26-triol. Depending on the chemical structure of the saponins and avenanthramides, sensory studies revealed human orosensory recognition thresholds of these phytochemicals to range between 3 and 170 μmol/L.

Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships

Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure-antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.

Induction of hydroxyanthranilate hydroxycinnamoyl transferase activity by oligo-N-acetylchitooligosaccharides in oats

An assay method for hydroxycinnamoyl-CoA: hydroxyanthranilate N- hydroxycinnamoyl transferase (HHT) in oat leaves (Avena sativa L.), which is thought to be one of the key enzymes for the biosynthesis of avenanthramides, phytoalexins in this plant, was established. HHT activity was induced by treating the leaves with oligo-N-acetylchitooligosaccharides. Among the chitooligosaccharides tested, penta-N-acetylchitopentaose ((GlcNAc)5) was the most effective in inducing activity. The induction by (GlcNAc)5 was dose-dependent, in which case HHT activity was initially detected after 6 hr and reached a maximum by 12 hr. All of the putative precursors of avenanthramides acted as substrates for HHT, with 5-hydroxyanthranilic acid and feruloyl-CoA being the best substrates for the anthranilic moiety and the cinnamoyl moiety of avenanthramides, respectively.

The Phytoalexins of Oat Leaves: 4H-3,1-Benzoxazin-4-ones or Amides?

Synthetic evidence is presented that the major phytoalexin of oat leaves is not the 4H-3,1-benzoxazin-4-one previously reported, but the corresponding amide.Other oat and carnation phytoalexins are prepared.