Avenanthramide

Avenanthramides (anthranilic acid amides, formerly called "avenalumins")[1][2][3] are a group of phenolic alkaloids found mainly in oats (Avena sativa), but also present in white cabbage butterfly eggs (Pieris brassicae and P. rapae),[4] and in fungus-infected carnation (Dianthus caryophyllus).

[6][7] Oat kernel extracts with standardized levels of avenanthramides are used for skin, hair, baby, and sun care products.

[14][15] It was later found that three avenanthramides were the open-ring amides of avenalumins I, II, and III, which were previously reported as oat phytoalexins by Mayama and co-workers.

[18] However, little thought had been given to the active ingredient in oats responsible for the anti-inflammatory effect until more attention was paid to avenanthramides, which were first isolated and characterized in the 1980s by Collins.

[20][21] Since then, many congeners have been characterized and purified, and it is known that avenanthramides have antioxidant, anti-inflammatory, and anti-atherosclerotic properties, and may be used as a treatment for people with inflammatory, allergy, or cardiovascular diseases.

[21] More recent studies made by the University of Minnesota showed that the antioxidant and anti-inflammatory activities can be increased through the consumption of 0.4 to 9.2 mg/day of avenanthramides over eight weeks.

[24] Inflammation is a complex and self-protection reaction that occurs in the body against foreign substance, cell damage, infections, and pathogens.

[citation needed] Avenanthramides are known to have potent antioxidant activity, acting primarily by donating a hydrogen atom to a radical.

The effects of the avenanthramide-enriched extract of oats has been investigated in animals, and a diet of 20 mg avenanthramide per kilogram body weight in rats has been shown to increase the superoxide dismutase (SOD) activity in skeletal muscle, liver, and kidneys.

[33] Also, a diet based on avenanthramides enhances glutathione peroxidase activity in heart and skeletal muscles, protecting the organism from oxidative damages.

There is evidence that the amount of avenanthramides found in the grains is related to genotype, environment, crop year and location, and tissue (Matsukawa et al., 2000).

Dimberg found that the three avenanthramides tested (A, B, and C) remained in the trans conformation after 18 hours of exposure to UV light at 254 nm.

Structures of avenanthramides
Structures of avenanthramides