Avenanthramide
Avenanthramides (anthranilic acid amides, formerly called "avenalumins")
History
Oat has been used for personal care purposes since antiquity. Indeed, wild oats (Avena sativa) was used in skin care in
Colloidal oatmeal
In 2003, colloidal oatmeal was officially approved as a skin protectant by the
Since then, many
Function in Avena sativa
A. sativa produces avenanthramides as defensive
Medical and personal care uses
Anti-inflammatory and anti-itch activity
Studies made by Sur (2008) provide evidence that avenanthramides significantly reduce the inflammatory response.
Redness reduction
Avenanthramides have effective antihistaminic activity; they significantly reduce itch and redness compared with untreated areas.[28]
Suggested mechanism of action
According to Sur (2008), the anti-inflammatory effect of the avenanthramides is due to the inhibition of the
Antioxidant activity
Avenanthramides are known to have potent antioxidant activity, acting primarily by donating a hydrogen atom to a radical. An antioxidant is “any substance that, when present at low concentrations compared to those of an oxidisable substrate, significantly delays or prevents oxidation of that substrate” ( Halliwell, 1990). These phytochemicals are able to combat the oxidative stress present in the body that is responsible for causing cancer and cardiovascular disease.[32] Among the avenanthramides, there are different antioxidant capacities, where C has the highest capacity, followed by B and A.[5]
Dietary supplement
Avenanthramides extracted from oats show potent antioxidant properties in vitro and in vivo, and according to studies made by Dimberg (1992), its antioxidant activity is many times greater than other antioxidants such as caffeic acid and vanillin.[20] Aven-C is one of the most significant avenanthramides present in the oats, and it is responsible for oats' antioxidant activity. 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.[34]
Nomenclature
Avenanthramides consist of conjugates of one of three
Collins | Dimberg's original | Dimberg's modified | n | R1 | R2 | R3 |
---|---|---|---|---|---|---|
A | Bp | 2p | 1 | H | H | OH |
B | Bf | 2f | 1 | OCH3 | H | OH |
C | Bc | 2c | 1 | OH | H | OH |
O | 2pd | 2 | H | H | OH | |
P | 2fd | 2 | OCH3 | H | OH |
Biosynthesis
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). The environmental factors are not clearly known, but it is believed that lower levels of avenanthramides are produced in oats when they are grown in a dry environment, which disfavors crown rust, a kind of fungus that has been shown to stimulate avenanthramides production in oats grains.[5]
Chemical stability
pH
Avenanthramides are not all sensitive to pH and temperature. This was well illustrated in a study conducted on avenanthramides A, B and C.[5] In this study it was found that avenanthramide A (2p) concentration was essentially unchanged in sodium phosphate buffer after three hours at either room temperature or at 95 °C. Avenanthramides B (2f) appeared to be more sensitive to the higher temperature at pH 7 and 12. Avenanthramides C (2c) underwent chemical reorganization at pH 12 at both temperatures and diminished by more than 85% at 95 °C, even at pH 7 (Dimberg et al., 2001).[5]
UV
Avenanthramides are also affected by
Synthetic avenanthramides
Avenanthramides can be artificially synthesized. Avenanthramides A, B, D, and E were synthesized by Collins (1989), using chromatography methods, and adapting Bain and Smalley's procedure (1968).[35] All four synthetic substances were identical to the ones extracted from oats.[15]
References
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- ^ 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
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- ^ "AveenoMD Active naturals". aveenomd.com. 2014. Retrieved 8 April 2019.
- ^ 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
- ^ a b "Oat phenolics: avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls". Journal of Agriculture and Food Chemistry 37, 60–66.
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- ^ Crombie L and Mistry J. (1990) "The phytoalexins of oat leaves: 4-3,1-benzoazin-4-onmes or amides?" Tetrahedron Lettres 31, 2647–2648.
- ^ a b c "Less-known botanical cosmeceuticals". Dermatologic Therapy, Vol. 20, 330–342
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- ^ a b c 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".
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- ^ Kim, E.O., Min, K.J, Know, T.K., Um, B.H., Moreau, R. H., Choi, S.W.(2012) "Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated" Raw 264.7 macrophages. Elsevier, 1309-1316.
- ^ Chu, Y.F., Wise, M.L., Gulvady, A.A., Chang, T., Kendra, D.F., Klinken, B.J.V., Shi, Y., O’Shea, M. (2013). "In vitro antioxidant capacity and anti-inflammatory activity of seven common oats". Elsevier, 426-431.
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- ^ Guo W, Wise ML, Collins FW, Meydani M (2008) "Avenanthramides, polyphenols from oats, inhibit IL-1beta-induced NF-kappaB activation in endothelial cells". Free Radic Biol Med 44:415–429
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- ^ Bloom RZ. (2009). "Antioxidant and Anti-proliferative Properties of Selected Grape Seed Extracts". ProQuest, 13-16.
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- ^ Bain D., Smalley R. K. "Synthesis of 2-substituted-4(H)-3.1-benzoxazin-4-ones". J. Chem. Soc. C. 1968, 1593-1597.