Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.)

Radulović, Niko S.; Mladenović, Marko Z.; Blagojević, Polina D.; Stojanović-Radić, Zorica; Ilić-Tomič, Tatjana; Šenerović, Lidija; Nikodinovic-Runic, Jasmina

doi:10.1016/j.fct.2013.09.017

Cited by 43 publications

(47 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A solution of (1 R* ,3 S* ,5 R* )‐sabinol (200 mg, 1.3 mmol), nonanoic or decanoic acid (1.5 mmol), DMAP (37 mg, 0.3 mmol) and DCC (310 mg, 1.5 mmol) in 30 ml of dry CH 2 Cl 2 was stirred overnight at room temperature protected from atmosphere moisture by a CaCl 2 guard tube . The precipitated urea was filtered off and the filtrate was concentrated in vacuo .…”

Section: Methodsmentioning

confidence: 99%

The essential oil of Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl (Asteraceae) revisited: the stereochemical nomenclature issues, structural elucidation and synthesis of (new) sabinyl esters

Mladenović

Radulović

2016

Flavour & Fragrance J

Self Cite

View full text Add to dashboard Cite

Serbian Yarrow (Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl, Asteraceae) is a poorly investigated taxon, endemic to the Central Balkan Peninsula area. A combination of chromatographic and spectroscopic techniques enabled the identification of, in total, 300 constituents (comprising 95.5–97.2% of the total essential oil compositions) from the essential oils of the A. ageratifolia ssp. serbica dry aerial parts. A comparison of the essential‐oil compositions from plant material collected from two populations (Jelašnička klisura gorge and Suva Planina mountain, SE Serbia) in two consecutive years (2013 and 2014) confirmed that the biosynthesis/accumulation of the volatile metabolites for this species is not dependent on the environmental conditions and suggested the existence of a single chemotype of this species. The essential oil compositions were dominated by (1R*,3S*,5R*)‐sabinyl derivatives, including two completely new natural products: (1R*,3S*,5R*)‐sabinyl nonanoate and (1R*,3S*,5R*)‐sabinyl decanoate. The identity of these new esters was unambiguously confirmed by co‐injection of the essential oil samples with synthesized standards and their structure was elucidated by NMR (1D and 2D), IR and MS, whereas the stereochemistry of the esters was studied by an NMR methodology that employed lanthanide‐induced shift reagents. Additionally, a nomenclature confusion regarding the relative stereochemistry of sabinyl esters, that came from the opposing use of cis and trans for the parent alcohols and the derived esters, was addressed. We propose the use of CIP notation in connection with the trivial names to avoid further ambiguities. Copyright © 2016 John Wiley & Sons, Ltd.

show abstract

Section: Methodsmentioning

confidence: 99%

The essential oil of Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl (Asteraceae) revisited: the stereochemical nomenclature issues, structural elucidation and synthesis of (new) sabinyl esters

Mladenović

Radulović

2016

Flavour & Fragrance J

Self Cite

View full text Add to dashboard Cite

show abstract

“…Teixeira et al (2014), com avaliação de óleo essencial de alecrim-pimenta da região de Lavras, MG, corroboram com os aqui descritos, sendo os componentes majoritários carvacrol (41,51%), p--cimeno (18.36%), γ-terpineno (17,03 %) e timol (4,86%). Guimarães et al (2014) As diferenças de sensibilidade de óleos essenciais descritas na literatura estão associadas também a metodologia adotada incluindo na extração dos compostos ativos (Othman et al 2011, Radulović et al 2013). Acredita-se que a atividade antimicrobiana é dependente de vários alvos de ação dos óleos na célula que podem potencializar a atividade (Negi 2012).…”

Section: Discussionunclassified

Atividade antisséptica do óleo essencial de Lippia origanoides Cham. (Alecrim-pimenta) na presença de leite bovino

et al. 2016

View full text Add to dashboard Cite

905RESUMO.-Objetivou-se determinar atividade antisséptica do óleo essencial de Lippia origanoides na presença de leite bovino. A composição química do óleo essencial de alecrim pimenta foi determinada por cromatografia gasosa acoplada à espectrometria de massas (CG-EM), sendo detectados 53 compostos, dos quais 16 foram identificados (>0,1% área total). O carvacrol (32,7%), p-cimeno (23%), timilmetil éter, cariofileno (7,98%) e o γ-terpineno (5,40%) foram os componentes mais abundantes. A concentração inibitória mínima para Staphylococcus aureus ATCC 25923 e E. coli ATCC 8739 foi de 60µL/mL, enquanto para Salmonella Choleraesuis ATCC 35640 foi de 90µL/mL. A concentração bactericida mínima foi de 120µL/mL para as três bacté-rias. Avaliou-se a atividade antisséptica do óleo essencial na concentração de 120µL/mL na presença de leite bovino sobre as mesmas cepas bacterianas. O óleo em estudo apresentou efeito inibitório do crescimento das cepas em diferentes tempos de ação (p<0,05). S. aureus apresentou maiores índices de inibição após 5 min de contato e Escherichia coli e Salmonella Choleraesuis após 15 min. O óleo essencial de alecrim-pimenta revelou ser um potencial antimicrobiano natural, mesmo na presença de matéria orgâ-nica constituída de uma matriz nutricional complexa que é o leite bovino. This study aimed to determine the antiseptic activity of the essential oil of Lippia origanoides in the presence of bovine milk. The essential oil chemical composition was determined by gas chromatography-mass spectrometry (CG EM) 53 compounds were detected, of which 16 were identified (>0.1% total area). The carvacrol (32.7%), p-cymene (23%), thymil methyl ether (10.03%), caryophyllene (7.98 %) and γ-terpinene (5.40%) were the most abundant components. The minimum inhibitory concentration for Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 8739 was 60uL/mL, as for this Salmonella Choleraesuis ATCC 35640 was 90uL/mL. The minimum bactericidal concentration was 120μL/ mL for all three bacteria. We evaluated the antiseptic activity of the essential oil in the concentration of 120μL/mL in the presence of bovine milk for the same bacterial strains. The oil under study It showed an inhibitory effect of growth of the strains in different action times (p <0.05). S. aureus showed higher inhibition rates after 5 min of contact and E. coli and Salmonella Choleraesuis after 15 min. The essential oil Lippia origanoides proved to be a natural antimicrobial potential even in the presence of organic matter consists of a complex nutritional matrix is bovine milk.

show abstract

“…All NMR spectra were measured at 25°C in CDCl 3 with tetramethylsilane (TMS) as an internal standard. Chemical shifts are reported in ppm (δ) and referenced to TMS (δ H = 0 ppm) inH NMR spectra and/or to solvent protons (deuterated chloroform: δ H = 7.26 ppm and δ C = 77.16 ppm) in 13 C and heteronuclear 2D spectra. Scalar couplings are reported in hertz (Hz).…”

Section: Methodsmentioning

confidence: 99%

“…The statistical evaluation (regression analysis) of the data (the correlation coefficient (R) and root mean square of the errors (RMSE) were used as the statistical parameters for testing the quality of the regression equations) was performed by the program Microsoft Office Excel 2010 and/or Easy QSAR 1.0. The experimental data used in the models came from the compounds that were synthesized in this study and were treated as a learning set, while the retention indices of another set of esters previously prepared in our lab (C 5 esters (2‐methylbutanoates, 3‐methylbutanoates (isovalerates), pentanoates (valerates), ( Z )‐2‐methyl‐2‐butenoates (angelates), ( E )‐2‐methyl‐2‐butenoates (tiglates), and 3‐methyl‐2‐butenoates (senecioates))) and already published were used to test the model prediction set‐up using the training set. Thus, a model was sought for that could be used to calculate the value of RI for esters of regioisomeric allylmethoxypenols.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

Mladenović

Radulović

2019

Flavour & Fragrance J

Self Cite

View full text Add to dashboard Cite

A recent identification of eugenyl (allylmethoxyphenyl) esters as Anthemis segetalis Ten. (Asteraceae) essential oil constituents, accomplished by means of organic synthesis, motivated us to expand the existing synthetic library with an aim to examine the generality of structure‐chromatographic property relationships within this series of volatiles. Herein, the design, synthesis, gas–chromatographic and spectral characterization of members of a library of 85 allylmethoxyphenyl esters (64 are completely new) were described. Analysis of experimentally obtained RI data showed that esters of the same acid and different allylmethoxyphenols always elute in the same order from an apolar gas chromatography (DB‐5MS) column: 2‐allyl‐6‐methoxyphenyl < 2‐allyl‐3‐methoxyphenyl < 2‐allyl‐5‐methoxyphenyl < 2‐allyl‐4‐methoxyphenyl < 4‐allyl‐2‐methoxyphenyl esters. Based on the obtained RI values, several quantitative structure–property relationship models were built up that correlated several easily available parameters (e.g. Wiener [WI], Balaban [BI], and molecular topological [MTI] indices) of the mentioned esters and their RI data. The generated various quantitative structure–property relationships models (equations that predict RIs of esters of different regioisomers of allylmethoxyphenols with the same acids and the ones that predict RIs of esters of different acids with the same allylmethoxyphenols) were tested on data of previously known related esters. RI data of esters of allylmethoxyphenol regioisomers could be successfully predicted based on 1D topological indices, such as the Balaban, Wiener, and molecular topological indices. Together with RI and MS data accumulated in this work, these models represent a new and simple tool for the identification of allylmethoxyphenyl esters that might potentially represent new or rare natural products.

show abstract

Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.)

Cited by 43 publications

References 26 publications

The essential oil of Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl (Asteraceae) revisited: the stereochemical nomenclature issues, structural elucidation and synthesis of (new) sabinyl esters

The essential oil of Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl (Asteraceae) revisited: the stereochemical nomenclature issues, structural elucidation and synthesis of (new) sabinyl esters

Atividade antisséptica do óleo essencial de Lippia origanoides Cham. (Alecrim-pimenta) na presença de leite bovino

A synthetic library of allylmethoxyphenyl esters: spectral characterization and gas chromatographic behavior

Contact Info

Product

Resources

About