Antimicrobial and Antioxidant Activities of Clove Essential Oil and Eugenyl Acetate Produced by Enzymatic Esterification

Vanin, Adriana Biasi; Orlando, Tainára; Piazza, Suelen P.; Puton, Bruna Maria Saorin; Cansian, Rogério Luís; Oliveira, Débora de; Paroul, Natália

doi:10.1007/s12010-014-1113-x

Cited by 58 publications

(43 citation statements)

References 30 publications

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“…The results obtained in this work were similar to obtained by Vanin et al (2014), where the results of esterification of clove essential oil are better discussed. The low lethal concentrations obtained for both clove essential oil and eugenyl acetate could also indicate toxicity to other organisms such as larvae of insects vector of diseases.…”

Section: Determination Of Toxicity Against Artemia Salinasupporting

confidence: 89%

“…The production of eugenyl acetate via enzymatic esterification was carried out in the experimental condition optimized by Vanin et al (2014). The scheme of the reaction is presented in Figure 1.…”

Section: Methodsmentioning

confidence: 99%

“…Following the experimental condition described in the previous section (Vanin et al, 2014), the eugenyl acetate conversion was 95.6%. These results are similar to other studies from the literature.…”

Section: Enzymatic Production Of Eugenyl Acetatementioning

confidence: 99%

“…The acaricide activity of eugenyl acetate was related by Pasay et al (2010), since eugenyl acetate presented high toxicity against human scabies mites. This compound was also described as a potent antioxidant agent by Vanin et al (2014). The authors observed that the clove essential oil after esterification presented higher antioxidant activity compared to crude essential oil (IC 50 of 283.9 μg.mL -1 and 367.5 μg.mL -1 , respectively).…”

Section: Introductionmentioning

confidence: 96%

“…The oil also presents other components of terpenes source as β-cariofilen, α-humulen and eugenyl acetate (Chaieb et al, 2007;Dzamic et al, 2009). Eugenol has different biological properties confirmed: bactericide (Moon et al, 2011), antifungal (Rana et al, 2011), larvicidal (Pandey et al, 2013), antioxidant (Chiaradia et al, 2012;Vanin et al, 2014), anti-inflammatory (Daniel et al, 2009), among others.…”

Section: Introductionmentioning

confidence: 99%

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Toxicity of clove essential oil and its ester eugenyl acetate against Artemia salina

et al. 2017

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The production of compounds via enzymatic esterification has great scientific and technological interest due to the several inconveniences related to acid catalysis, mainly by these systems do not fit to the concept of "green chemistry". Besides, natural products as clove oil present compounds with excellent biological potential. Bioactives compounds are often toxic at high doses. The evaluation of lethality in a less complex animal organism can be used to a monitoring simple and rapid, helping the identification of compounds with potential insecticide activity against larvae of insect vector of diseases. In this sense, the toxicity against Artemia salina of clove essential oil and its derivative eugenyl acetate obtained by enzymatic esterification using Novozym 435 as biocatalyst was evaluated. The conversion of eugenyl acetate synthesis was 95.6%. The results about the evaluation of toxicity against the microcrustacean Artemia salina demonstrated that both oil (LC 50 = 0.5993 µg.mL -1 ) and ester (LC 50 = 0.1178 µg.mL -1 ) presented high toxic potential, being the eugenyl acetate almost 5 times more toxic than clove essential oil. The results reported here shows the potential of employing clove oil and eugenyl acetate in insecticide formulations.Keywords: Novozym 435, Caryophyllus aromaticus, enzymatic esterification.Toxicidade do óleo essencial de cravo e seu éster acetato de eugenila contra Artemia salina ResumoA produção de compostos via esterificação enzimática possui grande interesse científico e tecnológico devido às inúmeras inconveniências relacionadas com a catálise ácida, principalmente por estes sitemas não se adequarem ao atual termo "tecnologias limpas". Além disso, produtos naturais como o óleo de cravo, apresentam compostos com excelentes potenciais biológicos. Compostos bioativos são quase sempre tóxicos em altas doses. A avaliação da letalidade em um organismo animal menos complexo pode ser usada para um monitoramento simples e rápido, servindo também para a identificação de compostos com potencial atividade inseticida contra larvas de insetos vetores de doenças. Neste sentido, foi determinada a toxicidade frente a Artemia salina do óleo essencial de cravo e do seu derivado acetato de eugenila obtido por esterificação enzimática com lipase Novozym 435. A conversão da reação de síntese de acetato de eugenila foi de 95,6%. Os resultados referentes à avaliação da toxicidade frente ao microcrustáceo Artemia salina demonstraram que tanto o óleo (LC 50 = 0,5993 µg.mL -1 ) quanto o éster (LC 50 = 0,1178 µg.mL -1 ) apresentam elevado potencial toxicológico, sendo que o éster apresenta aproximadamente 5 vezes mais toxicidade em relação ao óleo. Estes resultados demonstram o potencial emprego do óleo de cravo e de acetato de eugenila em formulações de inseticidas.Palavras-chave: Novozym 435, Caryophyllus aromaticus, esterificação enzimática.

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Section: Determination Of Toxicity Against Artemia Salinasupporting

confidence: 89%

Section: Methodsmentioning

confidence: 99%

Section: Enzymatic Production Of Eugenyl Acetatementioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Toxicity of clove essential oil and its ester eugenyl acetate against Artemia salina

et al. 2017

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Continuous production of eugenol esters using enzymatic packed‐bed microreactors and an evaluation of the products as antifungal agents

Giovannini

Catani

Massi

et al. 2019

Flavour & Fragrance J

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The enzymatic synthesis of biologically active compounds is receiving increasing interest from academic and industrial researchers. Herein, we report on the continuous‐flow enzymatic production of eugenol esters with packed‐bed microreactors prepared with the Novozym 435 and Lipozyme RM IM lipases. After optimization of the independent process variables, namely temperature (68 °C), flow rate (8 μL min−1), and eugenol/isobutyric anhydride molar ratio (1 : 5) by means of experimental design methodologies, the unprecedented continuous‐flow production of eugenyl isobutyrate has been achieved with steady‐state conversions of 77 and 70%, using packed‐bed microreactors prepared with Novozym 435 and Lipozyme RM IM, respectively. With acetic anhydride as the acylating agent, the same reactors, under the same conditions, afforded eugenyl acetate with steady‐state conversions of 82% (Novozym 435) and 90% (Lipozyme RM IM). The two ester products have been tested against phytopathogenic and dermatophytic fungi, demonstrating interesting action against dermatophytic fungi. The reported results demonstrated the suitability of the enzymatic packed‐bed microreactors as a sustainable and scalable technology for the solvent‐free continuous‐flow production of biologically active esters of eugenol.

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Response surface methodology for optimization of enzymatic acylation of (R)‐(‒)‐linalool application to essential oils

Naouel

Zeror

Merabet‐Khelassi

et al. 2023

Flavour & Fragrance J

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Linalool (3, 7-dimethylocta−1,6-dien-3-ol) is an acyclic tertiary monoterpene alcohol that is present naturally in almost all essential oils in varying concentration degrees. 1,2 It is utilized generally in perfumery and many flowery fragrance compositions for fruityfresh odours such as neroli, lavender, and lily of the valley. 3 Linalool was included in the list of class "A" substances due to its usefulness as primal matter for the synthesis of high-value added compounds, such as their ester derivatives, 4,5 especially the acetate form. 6,7 Unlike linalool, linalyl acetate is also used as safe flavour adjuvants in food industries due to their high stability and low toxicity and in addition to their pharmacological properties such as antioxidant, antibacterial, or anti-inflammatory activities. [8][9][10] Linalool exists naturally as two isomeric forms, the 3R-(−)-linalool called licareol (odour threshold 0.8 ppb) that has a lavender or lily-of-the-valley odour and the dextrorotatory isomer is 3 S-(+)-linalool called coriandrol (odour threshold 7.4 ppb) that has a herbaceous and musty green smell 11 Licareol is the most common isomeric form; both enantiomers are available in nature, and the stereoisomeric composition of this alcohol influences the olfactory properties of the essential oils containing it. 4,5 For example, the enantiomeric distribution of (R)-(−) and (S)-(+) forms of linalool and linalyl acetate are important indicators of lavender oil purity. 12 Traditionally, monoterpene esters are obtained by conventional chemical synthesis or by extraction from plants. 13,14 However, the extraction and purification way remains less viable due to the large amount of raw material needed, high costs, and the smaller essential oil yield to meet the high industrial demand, 15 while the chemical ways use harmful reagents and causing environment pollution. 16,17 To circumvent those disadvantages and according to the increase demand for greener, environment-friendly processes, biocatalysis seems the ideal

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Antimicrobial and Antioxidant Activities of Clove Essential Oil and Eugenyl Acetate Produced by Enzymatic Esterification

Cited by 58 publications

References 30 publications

Toxicity of clove essential oil and its ester eugenyl acetate against Artemia salina

Toxicity of clove essential oil and its ester eugenyl acetate against Artemia salina

Continuous production of eugenol esters using enzymatic packed‐bed microreactors and an evaluation of the products as antifungal agents

Response surface methodology for optimization of enzymatic acylation of (R)‐(‒)‐linalool application to essential oils

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