Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.)
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2013
Authors
Radulović, Niko S.Mladenović, Marko Z.
Blagojević, Polina D.
Stojanović-Radić, Zorica Z.
Ilić-Tomić, Tatjana
Šenerović, Lidija
Nikodinović-Runić, Jasmina
Article (Published version)
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To determine the exact structure of previously tentatively identified minor essential-oil constituents of a Chamomile species (Antemis segetalis Ten. (Asteraceae)), we have synthesized a small combinatorial library of 54 regioisomeric allylmethoxyphenyl pentanoates and 2-pentenoates (49 completely new compounds). GC-MS in combination with 1D- and 2D-NMR analyses of the library compounds provided unambiguous data that led to a straightforward identification of the mentioned A. segetalis constituents as eugenyl angelate, 2-methylbutanoate and 3-methylbutanoate (0.21, 0.22, and 0.13 mg/100 g of fresh plant material, respectively). To assess the safety and potential beneficial pharmacological uses of these naturally occurring esters and several other library compounds (these were tested to provide relevant data for a SAR (structure-activity relationship) analysis), we have studied the effect of these compounds in several models of toxicity (acute toxicity against Artemia sauna, cytotoxicit...y against two cell lines (fibroblast and melanoma)), as well as their acetylcholinesterase inhibitory and antibacterial activities. Anthemis segetalis constituents showed low to moderate activity in all tests. The obtained results suggest that the intake of these compounds in naturally available amounts, on their own, would probably not represent a risk to human health but the possible adverse interactions with the plant matrix should not be neglected.
Keywords:
Eugenyl angelate / Eugenyl 3-methylbutanoate / Eugenyl 2-methylbutanoate / Essential oil / Anthemis segetalis Ten / AllylmethoxyphenolSource:
Food and Chemical Toxicology, 2013, 62, 554-565Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Combinatorial libraries of heterogeneous catalysts, natural products, and their derivatives and analogues: the way to biologically active compounds (RS-MESTD-Basic Research (BR or ON)-172061)
DOI: 10.1016/j.fct.2013.09.017
ISSN: 0278-6915
PubMed: 24055768
WoS: 000329960400073
Scopus: 2-s2.0-84885336587
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Radulović, Niko S. AU - Mladenović, Marko Z. AU - Blagojević, Polina D. AU - Stojanović-Radić, Zorica Z. AU - Ilić-Tomić, Tatjana AU - Šenerović, Lidija AU - Nikodinović-Runić, Jasmina PY - 2013 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/694 AB - To determine the exact structure of previously tentatively identified minor essential-oil constituents of a Chamomile species (Antemis segetalis Ten. (Asteraceae)), we have synthesized a small combinatorial library of 54 regioisomeric allylmethoxyphenyl pentanoates and 2-pentenoates (49 completely new compounds). GC-MS in combination with 1D- and 2D-NMR analyses of the library compounds provided unambiguous data that led to a straightforward identification of the mentioned A. segetalis constituents as eugenyl angelate, 2-methylbutanoate and 3-methylbutanoate (0.21, 0.22, and 0.13 mg/100 g of fresh plant material, respectively). To assess the safety and potential beneficial pharmacological uses of these naturally occurring esters and several other library compounds (these were tested to provide relevant data for a SAR (structure-activity relationship) analysis), we have studied the effect of these compounds in several models of toxicity (acute toxicity against Artemia sauna, cytotoxicity against two cell lines (fibroblast and melanoma)), as well as their acetylcholinesterase inhibitory and antibacterial activities. Anthemis segetalis constituents showed low to moderate activity in all tests. The obtained results suggest that the intake of these compounds in naturally available amounts, on their own, would probably not represent a risk to human health but the possible adverse interactions with the plant matrix should not be neglected. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Food and Chemical Toxicology T1 - Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.) EP - 565 SP - 554 VL - 62 DO - 10.1016/j.fct.2013.09.017 ER -
@article{ author = "Radulović, Niko S. and Mladenović, Marko Z. and Blagojević, Polina D. and Stojanović-Radić, Zorica Z. and Ilić-Tomić, Tatjana and Šenerović, Lidija and Nikodinović-Runić, Jasmina", year = "2013", abstract = "To determine the exact structure of previously tentatively identified minor essential-oil constituents of a Chamomile species (Antemis segetalis Ten. (Asteraceae)), we have synthesized a small combinatorial library of 54 regioisomeric allylmethoxyphenyl pentanoates and 2-pentenoates (49 completely new compounds). GC-MS in combination with 1D- and 2D-NMR analyses of the library compounds provided unambiguous data that led to a straightforward identification of the mentioned A. segetalis constituents as eugenyl angelate, 2-methylbutanoate and 3-methylbutanoate (0.21, 0.22, and 0.13 mg/100 g of fresh plant material, respectively). To assess the safety and potential beneficial pharmacological uses of these naturally occurring esters and several other library compounds (these were tested to provide relevant data for a SAR (structure-activity relationship) analysis), we have studied the effect of these compounds in several models of toxicity (acute toxicity against Artemia sauna, cytotoxicity against two cell lines (fibroblast and melanoma)), as well as their acetylcholinesterase inhibitory and antibacterial activities. Anthemis segetalis constituents showed low to moderate activity in all tests. The obtained results suggest that the intake of these compounds in naturally available amounts, on their own, would probably not represent a risk to human health but the possible adverse interactions with the plant matrix should not be neglected.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Food and Chemical Toxicology", title = "Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.)", pages = "565-554", volume = "62", doi = "10.1016/j.fct.2013.09.017" }
Radulović, N. S., Mladenović, M. Z., Blagojević, P. D., Stojanović-Radić, Z. Z., Ilić-Tomić, T., Šenerović, L.,& Nikodinović-Runić, J.. (2013). Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.). in Food and Chemical Toxicology Pergamon-Elsevier Science Ltd, Oxford., 62, 554-565. https://doi.org/10.1016/j.fct.2013.09.017
Radulović NS, Mladenović MZ, Blagojević PD, Stojanović-Radić ZZ, Ilić-Tomić T, Šenerović L, Nikodinović-Runić J. Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.). in Food and Chemical Toxicology. 2013;62:554-565. doi:10.1016/j.fct.2013.09.017 .
Radulović, Niko S., Mladenović, Marko Z., Blagojević, Polina D., Stojanović-Radić, Zorica Z., Ilić-Tomić, Tatjana, Šenerović, Lidija, Nikodinović-Runić, Jasmina, "Toxic essential oils. Part III: Identification and biological activity of new allylmethoxyphenyl esters from a Chamomile species (Anthemis segetalis Ten.)" in Food and Chemical Toxicology, 62 (2013):554-565, https://doi.org/10.1016/j.fct.2013.09.017 . .