Chemical composition and antifungal activity of Illicium verum and Eugenia caryophyllata essential oils

Džamić, Ana M.; Sokóvić, Marina; Ristić, Mihailo; Grijic-Jovanovic, Slavica; Vukojevic, Jelena; Marin, Petar D.

doi:10.1007/s10600-009-9283-4

Cited by 49 publications

(29 citation statements)

References 13 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Various techniques can be used for extraction of essential oil from star anise fruit, such as hydrodistillation (HD), steam distillation (SD), solvent extraction (SE), supercritical fluid CO 2 extraction (SFE), hydrodistillation-headspace solvent microextraction (HD-HSME), and microwave-assisted extraction (MAE) (Zhai et al, 2009;Dzamic et al, 2009;Gholivand et al, 2009;Wang et al, 2007a,b;Lee et al, 2007;Yan et al, 2002).…”

Section: Volatiles and Extraction Techniquesmentioning

confidence: 99%

Illicium verum: A review on its botany, traditional use, chemistry and pharmacology

Wang

Huang

et al. 2011

Journal of Ethnopharmacology

231

149

View full text Add to dashboard Cite

Section: Volatiles and Extraction Techniquesmentioning

confidence: 99%

Illicium verum: A review on its botany, traditional use, chemistry and pharmacology

Wang

Huang

et al. 2011

Journal of Ethnopharmacology

231

149

View full text Add to dashboard Cite

“…The concentration of eugenol varies from 77-95% (Trajano et al, 2010;Singh et al, 2012). 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%

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

et al. 2017

View full text Add to dashboard Cite

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.

show abstract

“…Three new (1-3) and seven known compounds (4)(5)(6)(7)(8)(9)(10) were isolated by various chromatographic separations from the EtOAc extract of the fruits of I. verum (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…1,2) Several sesquiterpenoids, flavonoids, phenylpropanoids and lignans have been previously isolated from this plant [3][4][5][6] and been reported to possess anti-human immunodeficiency virus (HIV), cancer chemopreventive and antifungal activities. [7][8][9] The authors previously reported medicinal plant derived compounds that inhibit topoisomerases I and II. [10][11][12][13][14][15] Topoisomerases are enzymes that control DNA topology in cells and are targets of anticancer drugs.…”

mentioning

confidence: 99%

DNA Topoisomerase Inhibitory Activity of Constituents from the Fruits of <i>Illicium verum</i>

et al. 2017

View full text Add to dashboard Cite

Three new compounds, a sesquilignan (1) and two glucosylated phenylpropanoids (2, 3), and seven known compounds (4-10), were isolated from the fruits of Illicium verum HOOK. FIL. (Illiciaceae). The structures of 1-3 were determined based on one and two dimensional (1D-and 2D-) NMR data and electronic circular dichroism (ECD) spectra analyses. Compounds 3, 5, 6, and 8-10 exhibited potent inhibitory activities against topoisomerase II with IC 50 values of 54.6, 25.5, 17.9, 12.1, 0.3 and 1.0 µM, respectively, compared to etoposide, the positive control, with an IC 50 of 43.8 µM.Key words Illicium verum; topoisomerase I; topoisomerase II; cytotoxicity Star anise (the fruits of Illicium verum HOOK. FIL., Illiciaceae) has been used as a traditional medicine to treat diverse disease such as stomach aches, insomnia, and skin inflammation in Asia.1,2) Several sesquiterpenoids, flavonoids, phenylpropanoids and lignans have been previously isolated from this plant [3][4][5][6] and been reported to possess anti-human immunodeficiency virus (HIV), cancer chemopreventive and antifungal activities.7-9) The authors previously reported medicinal plant derived compounds that inhibit topoisomerases I and II. [10][11][12][13][14][15] Topoisomerases are enzymes that control DNA topology in cells and are targets of anticancer drugs.16,17) Topoisomerase I cleaves and reseals one DNA strand at a time without requiring ATP to pass the complementary strand through the enzyme-linked strand break, and thus affect DNA relaxation. On the other hand, topoisomerase II cleaves both strands of DNA during catalysis. In a reaction coupled to ATP binding and hydrolysis, these proteins were found to cleave one DNA duplex, transport a second duplex through the break, and then ligate the cleaved duplex. [18][19][20] Camptothecin (CPT) and etoposide (VP-16) are well-known inhibitors of topoisomerases I and II, respectively. 16,17) Here, the authors report the isolation of ten compounds, including a new sesquilignan and two new glycosylated phenylpropanoids, from the fruits of I. verum, and describe cytotoxicity and their DNA topoisomerases I and II inhibitory activities. Results and DiscussionThree new (1-3) and seven known compounds (4-10) were isolated by various chromatographic separations from the EtOAc extract of the fruits of I. verum (Fig. 1). The molecular formula of 1 was established as C 30

show abstract

Chemical composition and antifungal activity of Illicium verum and Eugenia caryophyllata essential oils

Cited by 49 publications

References 13 publications

Illicium verum: A review on its botany, traditional use, chemistry and pharmacology

Illicium verum: A review on its botany, traditional use, chemistry and pharmacology

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

DNA Topoisomerase Inhibitory Activity of Constituents from the Fruits of <i>Illicium verum</i>

Contact Info

Product

Resources

About