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avenanthramide
Avenanthramides (Anthranilic acid amides) are a group of phenolic alkaloids found mainly in oats (''Avena Sativa''), but also present in white cabbage butterflies eggs (''Pieris brassicae and P. rapae'') and in fungus infected carnation (''Dianthus caryophyllus'').〔Chu Y. (2014). "Oats nutrition and technology". (1 edition). Wiley Blacwell〕 A number of studies demonstrate that these natural products have anti-inflammatory, antioxidant, anti-itch, anti-irritant, and antiatherogenic activities.〔Koening, R.T., Dickman, J.R., Wise, M.L., Ji,L.L. (2011). "Avenanthramides Are Bioavailable and Accumulate in Hepatic,Cardiac, and Skeletal Muscle Tissue Following Oral Gavage in Rats". Journal of Agricultural and food chemistry, 6438 – 6443〕〔Kurtz, E.S.; Wallo, W. "Colloidal oatmeal: history, chemistry and clinical properties". Journal Drugs Dermatol. 2007,6,167-170〕 Oat kernel extracts with standardized levels of Avenanthramides are ideal for skin, hair, baby and sun care products.〔Ceapro Inc, Canada. CP Oat Avenanthramide Extract. Available at: http://ceapro.com/wp-content/uploads/2012/09/CPOatAvenanthramideExtract-902-3043-Jun-131.pdf . Accessed at August, 10th of 2014.〕〔Oat cosmetics – Advancing Oat Technology. CP Oat Avenanthramides. Available at: http://oat.co.uk/ingredients-formulations/oat-av/. Accessed at August, 10th of 2014.〕 〔Oat cosmetics – The natural ingredient house. CP Oat Avenanthramides. Available at: https://www.in-cosmetics.com/__novadocuments/2746. Accessed at August, 10th of 2014.〕 〔Agriculture and Agri-Food Canada (2013). Innovation Express Vol.4 No 2. Available at: http://www.agr.gc.ca/eng/science-and-innovation/science-publications-and-resources/innovation-express-magazine/innovation-express-volume-4-no-2-2013/?id=1372115512470. Accessed at August, 11th of 2014〕 〔Cosmetic & Toiletries – Science Applied. CP Oats Avenanthramides. Available at: http://dir.cosmeticsandtoiletries.com/detail/tradeName.html?id=20310. Accessed at August 11th of 2014.〕 〔AveenoMD Active naturals (2014). Oats. Available at: https://www.aveenomd.com/active-naturals-ingredients/oats. Accessed at August 11th of 2014.〕 The name “Avenanthramides” was coined by Collins when he reported the presence of these compounds in oat kernels.〔Collins FW and Mullin WJ (1988) "High-performance liquid chromatographic determination of avenanthramides, N-aroylanthranilic acid alkaloids from oats". Journal of Chromatography A, 445, 363-370〕 〔"Oat phenolics: avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls". Journal of Agriculture and Food Chemistry 37, 60-66.〕 It was later found that three avenanthamides were the open ring amides of Avenalumins I, II and III which were previously reported as oat phytoalexins by Mayama and co-workers.〔Mayama S, Tani T, Matsuura Y, Ueno T. and Fukami H. (1981) "The production of phytoalexins by oat in response to Crown Rust, Puccina coronate f. sp. Avenae". Physiological Plant Pathology 19, 217-226.〕 〔Crombie L and Mistry J. (1990) "The phytoalexins of oat leaves: 4-3,1-benzoazin-4-onmes or amides?" Tetrahedron Lettres 31, 2647-2648.〕
== History ==
Oat has been used for personal care purposes since antiquity. Indeed, wild oats (''Avena sativa'') was used in skin care in Egypt and the Arabian peninsula 2000 BC.〔"Less-known botanical cosmeceuticals". Dermatologic Therapy, Vo. 20, 330-342〕 Oat bath was a common treatment of insomnia, anxiety and skin diseases such as eczema and burns.〔 In Roman times, its use as a medication for dermatological issues was reported by Pliny, Columella, and Theophrastus.〔Melardi MG. (2013) "Avena". Available at: http://www.lapelle.it/alimentazione/avena.htm〕 In the 19th century, oatmeal baths were often used to treat many cutaneous conditions, especially pruritic inflammatory eruptions. In the 1930s, the literature provided further evidence about the cleansing action of oat along with its ability to relieve itching and protect skin. In 2003, colloidal oatmeal was officially approved as a skin protectant by the FDA.〔 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.〔Dimberg LH. Theander O, Lingnert H. "Avenanthramides - a group of phenolic antioxidants in oats". Cereal Chem. 1992;70:637–641.〕 〔Carder G., Chu, Y. Chung, Y. French, J.A., O'Shea, M., Jan-Willem, B.K. (2013). U. S. Patent No. 833,717. Chicago, IL (US), "United States Patent Application Publication".〕
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.〔 In 1999 studies made by Tufts University showed that avenanthramides are bioavailable and keep bioactive in humans after consumption.〔 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 during 8 weeks.〔Chatel, R.E., Chu, Y.F., Chung, Y., French, J.A., O'Shea, M., (2013). Publication number US20130183405 A1. "Method of Processing Oats to Achieve Oats with an Increased Avenanthramide Content".〕
The International Nomenclature of Cosmetic Ingredients (INCI) originally called an oat extract with a standardized level of Avenanthramides as “Avena sativa kernel extract” however, recently, they also accepted the INCI name “Avenanthramides” to describe an extract containing 80% of these oat phenolic alkaloids.〔 〔Fowler, J. J., (2007) "Examining options for Barrier Protection in Atopic Dermatitis and Eczema". Clinical update – Recent insights into the origin and management of atopic dermatitis. Supported by Johnson & Johnson.〕
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