Antioxidant Properties of Ethyl Vanillinin Vitroandin Vivo

Abstract

We systematically evaluated the antioxidant activity of ethyl vanillin, a vanillin analog, as compared with the activities of vanillin and other vanillin analogs using multiple assay systems. Ethyl vanillin and vanillin exerted stronger antioxidant effects than did vanillyl alcohol or vanillic acid in the oxygen radical absorbance capacity (ORAC) assay, although the antioxidant activities of vanillyl alcohol and vanillic acid were clearly superior to those of ethyl vanillin and vanillin in the three model radical assays. The antioxidant activity of ethyl vanillin was much stronger than that of vanillin in the oxidative hemolysis inhibition assay, but was the same as that of vanillin in the ORAC assay. Oral administration of ethyl vanillin to mice increased the concentration of ethyl vanillic acid, and effectively raised antioxidant activity in the plasma as compared to the effect of vanillin. These data suggest that the antioxidant activity of ethyl vanillin might be more beneficial than has been thought in daily health practice.Key words: ethyl vanillin; ABTS radical cation; oxygen radical absorbance capacity (ORAC); oxidative hemolysis inhibition assay; plasma antioxidant activityThe association of reactive oxygen species and free radicals with many disease states is now well recognized, and antioxidants have attracted considerable attention.1,2) It has been reported that there are two types of antioxidants that scavenge radicals quickly and quench many radicals, and it has been proposed that reactivity should be assessed on the basis of both reaction rate and stoichiometry, 3) and that multiple methods should be used, since the activities of some antioxidants vary depending on the assay method.3-6) In addition, comparative studies using common antioxidants appear to be essential to clarify the biological significance of the activities of samples. We have assessed antioxidant activities with attention to the above-mentioned proposals and points of view. We found that 2-O--D-glucopyranosyl-L-ascorbic acid (AA-2G), a stable ascorbic acid derivative, exerted radical-scavenging activity toward unnatural model radicals, including DPPH radical [7][8][9][10] and ABTS radical cation (ABTS þ ). 9,11) The chemical properties of AA-2G as a radical scavenger were widely different from those of ascorbic acid, in that the reaction rate with these model radicals of AA-2G was much slower, but the long-term radical scavenging ability per molecule of AA-2G was superior to that of ascorbic acid. Recently, we reassessed the antioxidant activity of arbutin using five in vitro assay systems, though arbutin has been reported to possess weak antioxidant activity as compared to its precursor, hydroquinone.12) We found that arbutin exerted strong antioxidant activity, comparable or even superior to that of hydroquinone in the ABTS þ -scavenging assay, the ORAC assay, and two cell-based antioxidant assays.Vanillin is widely used in foods, beverages, cosmetics, and drugs. It has been reported to have multifunctional effects, including an...

Vanillin and Vanillin Analogs Relax Porcine Coronary and Basilar Arteries by Inhibiting L-Type Ca2+Channels

“…The order of relaxing potencies of VA and its analogs may be related to their varying hydrophobicity which, to judge from the elution time during reversed-phase high-performance liquid chromatography separation (Shyamala et al, 2007;Tai et al, 2011), follows the same ranking as observed in the present experiments. Such a difference in hydrophobicity of VA, VAA, and EtVA may be responsible not only for their different antioxidant activities/capacities (Tai et al, 2011) but also for their varying potencies in inhibiting L-type Ca 21 channels (as discussed herein), which are involved in contractions to KCl, U46619, and endothelin-1 Kasuya et al, 1989;Sato et al, 2000;Nobe and Paul, 2001).…”

“…Based on these properties, VA, VAA, and EtVA could be used to prevent or relieve exaggerated Ca 21 influx resulting in PKC activation in coronary (Ito et al, 1994;Kadokami, et al, 1996) or cerebral (Laher and Zhang, 2001) vasospasm and other cardiovascular disorders (Khalil, 2013). However, the concentrations of VA and its analogs needed to act as antioxidants (Shyamala et al, 2007;Jung et al, 2010;Kwon et al, 2013;Lee et al, 2013) or as vasodilators (present study) are larger than the measured plasma level [0.0005 mM] reached after oral administration of 30 mg/kg VA in male ICR (imprinting control region) mice (Tai et al, 2011). This comparison implies that to obtain a therapeutically favorable coronary and/or cerebral vasodilator, larger doses of VA and its analogs would be required than are achieved with their use as additives.…”

“…Such a difference in hydrophobicity of VA, VAA, and EtVA may be responsible not only for their different antioxidant activities/capacities (Tai et al, 2011) but also for their varying potencies in inhibiting L-type Ca 21 channels (as discussed herein), which are involved in contractions to KCl, U46619, and endothelin-1 Kasuya et al, 1989;Sato et al, 2000;Nobe and Paul, 2001). U46619 (n = 8-10) coronary artery 3.31 6 0.06 154.9 6 14.9 2.49 6 0.10* 73.5 6 6.4* 4.03 6 0.07* 223.5 6 8.6* U46619 (n = 8) basilar artery 2.77 6 0.15 118.9 6 7.9 2.22 6 0.29* 81.5 6 11.5* 3.16 6 0.16 145.4 6 10.9 40 mM KCl (n = 8-9) coronary artery 3.26 6 0.03 151.2 6 5.2 3.20 6 0.07 148.6 6 6.7 3.49 6 0.04* 173.9 6 3.4* Endothelin-1 (n = 10-11) coronary artery 3.64 6 0.09 206.5 6 12.2 3.30 6 0.10* 170.9 6 9.1* 4.13 6 0.07* 253.0 6 8.5* *Statistically significant difference (P , 0.05) from vanillin group.…”

“…They are commonly used as flavoring agents or as additives by the food, cosmetic, and pharmaceutic industries. VA and its analogs have antioxidant (Shyamala et al, 2007;Jung et al, 2010;Tai et al, 2011;Kwon et al, 2013;Lee et al, 2013), antiinflammatory (Jung et al, 2010;Kwon et al, 2013;Lee et al, 2013), antiproliferative, and antiangiogenic (Fukuoka et al, 2004;Lirdprapamongkol et al, 2009;Jung et al, 2010) properties as well as antitumor properties (Lirdprapamongkol et al, 2009) in vitro and in vivo. VA provides protection against global cerebral ischemia in Mongolian gerbils (Kim et al, 2007), and VAA protects against apoptosis induced by a neurotoxin )] in dopaminergic MN9D cells (a mesencephalic cell line) (Kim et al, 2011).…”

A Comparative Study on Propolis and Pollen Extracts: Chemical Profile Analysis, Antioxidant and Anticancer Activity

“…Apoptosis of MCF-7 cells may be due to the DNA damage and expression of apoptotic proteins (Natarajan et al, 2011). Ethyl vanillin and vanillin exerted stronger antioxidant effects than did vanillyl alcohol or vanillic acid (Tai et al, 2011) . Rosmarinic acid has antioxidant, anti-inflammatory and antimicrobial activities.…”