Effect of vanillin and ethyl vanillin on cytochrome P450 activity in vitro and in vivo

Vanillin is widely used as a flavoring agent in foods, perfumes and in several other applications. Even if huge amounts of vanillin are annually employed in these manufacturing processes, its reactivity is underexplored, especially for the formation of potentially toxic substances. In this context, we observed the formation of orange to red crystalline compounds Vanillin (4-hydroxy-3-methoxybenzaldehyde) is one of the most important flavoring compounds used in foods, beverages, food supplements, perfumes and pharmaceuticals. [1] This compound, in its natural form, is extracted from orchids of the genus Vanilla (e.g. Vanilla planifolia Jacks. ex Andrews). However, being the extraction very expensive and covering just a little percentage of the market request, synthetic vanillin (or more recently "ethylvanillin", 3-ethoxy-4-hydroxybenzaldeyde, "bourbonal", characterized by a stronger and persistent aroma) is nowadays the most used by industry. Vanillin is commonly synthesized using guaiacol, eugenol [2][3][4] or 4-hydroxybenzaldehyde [5] as starting materials or can be also easily prepared starting from different molecules (often from ferulic acid or eugenol), following different enzymatic/microbial routes, [6,7] allowing to fulfil the market demand. The annual worldwide consumption of vanillin exceeds 16,000 tons, even if the estimation of consumed vanillin originated from vanilla pods is only about 0.25 %. The expected global market of natural and synthetic vanillin will grow at a CAGR of 8.2 % in the forecast period 2019-2024, reaching USD 493 million. [8] Vanillin was recognized as suitable for food use by FDA since 1977. [9] Additionally, several studies on bioactivity of this aromatic compound were produced, displaying potential anti-bacterial, [10][11][12] anti-mutagen [13,14] and anti-oxidant [15] activities. Despite this safe profile, some drug interactions between vanillin/ethylvanillin and drugs metabolized by CYP2E1/ CYP1A2 might be possible. [16] No data [a]

show abstract

“…[1] This compound, in its natural form, is extracted from orchids of the genus Vanilla (e.g. [16] No data [a] ex Andrews).…”

mentioning

confidence: 99%

Unprecedented Formation of 2,5‐Diaminoquinones from the Reaction of Vanillin with Secondary Amines in Aerobic Conditions

et al. 2019

View full text Add to dashboard Cite

show abstract

“…EVA has been used as an antioxidant agent for oxidative injury. This compound has been examined for antioxidant properties via in vivo and in vitro studies (21,28,29). The present study investigated the effect of EVA on Aβ 1-42 -induced PC12 cells, a common in vitro model of AD (31).…”

Section: Discussionmentioning

confidence: 99%

“…A previous study suggested that the antioxidative activity of EVA is more potent compared with vanillin, as demonstrated by oxidative hemolysis inhibition assays (28). In addition, EVA can reduce the increase in ROS levels and metalloproteinase-9 expression levels in lipopolysaccharide (LPS)-stimulated macrophages, indicating that it could protect from neurodegeneration and oxidative damage (21,29). Based on the above evidence, the current study investigated the pro-survival activity of EVA against the oxidative damage caused by Aβ 1-42 -induced toxicity in PC12 cells.…”

Section: Introductionmentioning

confidence: 99%

Protective effect of ethyl vanillin against Aβ‑induced neurotoxicity in PC12 cells via the reduction of oxidative stress and apoptosis

et al. 2019

View full text Add to dashboard Cite

Increased aggregation of β-amyloid (Aβ) peptides induces oxidative stress, which is considered a major contributor in the development of Alzheimer's disease (AD). Prevention of Aβ-induced neurotoxicity is proposed as a possible modality for treatment of AD. The present study aimed to elucidate possible effects of ethyl vanillin (EVA), an analog of vanillin isolated from vanilla beans, on the Aβ1-42-induced oxidative injury in PC12 cells. EVA restrained the decrease in PC12 cell viability and apoptosis induction caused by treatment with Aβ1-42. In addition, EVA markedly alleviated intracellular lipid peroxidation as demonstrated by malondialdehyde levels and reactive oxygen species production in Aβ1-42-treated PC12 cells. In addition, the reduction in the activity levels of the antioxidative enzymes superoxide dismutase, catalase and glutathione peroxidase was detected in Aβ1-42-treated PC12 cells. This effect was partially reversed by treatment with EVA. Furthermore, the results indicated that EVA attenuated Aβ1-42-induced caspase-3 activation and the increase noted in the apoptosis regulator Bcl-2/apoptosis regulator Bax ratio of PC12 cells. These results indicated that EVA could be used as an efficient and novel agent for the prevention of neurodegenerative diseases via inhibition of oxidative stress and cell apoptosis.

show abstract

“…Recently, several researches suggested that the antioxidant activity of EVA was much stronger than that of vanillin in the oxidative hemolysis inhibition assay [22]. In addition, EVA has an ability against the enhanced ROS level and metalloproteinase-9 in the LPS-stimulated macrophage cells, indicating that it could protect neurodegeneration from oxidative damage [23, 24]. It has been reported that EVA plays a protective role against protein oxidation and apoptosis in rotenone-induced rat model of Parkinson's disease [25].…”

Section: Introductionmentioning

confidence: 99%

Ethyl Vanillin Protects against Kidney Injury in Diabetic Nephropathy by Inhibiting Oxidative Stress and Apoptosis

Tong

Liu

Gong

et al. 2019

Oxidative Medicine and Cellular Longevity

View full text Add to dashboard Cite

Diabetes-induced oxidative stress and apoptosis is regarded as a critical role in the pathogenesis of diabetic nephropathy (DN). Treating diabetes-induced kidney damage and renal dysfunction has been thought a promising therapeutic option to attenuate the development and progression of DN. In this study, we investigated the renoprotective effect of ethyl vanillin (EVA), an active analogue of vanillin isolated from vanilla beans, on streptozotocin- (STZ-) induced rat renal injury model and high glucose-induced NRK-52E cell model. The EVA treatment could strongly improve the deterioration of renal function and kidney cell apoptosis in vivo and in vitro. Moreover, treating with EVA significantly decreased the level of MDA and reactive oxygen species (ROS) and stabilized antioxidant enzyme system in response to oxidative stress by enhancing the activity of superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-Px) in vivo and in vitro. Furthermore, EVA also markedly suppressed cleaved caspase-3, Bax, and nuclear transcription factor erythroid 2-related factor (Nrf2) expression in STZ-induced rats. Therefore, these results of our investigation provided that EVA might protect against kidney injury in DN by inhibiting oxidative stress and cell apoptosis.

show abstract

Effect of vanillin and ethyl vanillin on cytochrome P450 activity in vitro and in vivo

Cited by 22 publications

References 15 publications

Unprecedented Formation of 2,5‐Diaminoquinones from the Reaction of Vanillin with Secondary Amines in Aerobic Conditions

Unprecedented Formation of 2,5‐Diaminoquinones from the Reaction of Vanillin with Secondary Amines in Aerobic Conditions

Protective effect of ethyl vanillin against Aβ‑induced neurotoxicity in PC12 cells via the reduction of oxidative stress and apoptosis

Ethyl Vanillin Protects against Kidney Injury in Diabetic Nephropathy by Inhibiting Oxidative Stress and Apoptosis

Contact Info

Product

Resources

About