TY  - JOUR
AU  - Trifunović, Snežana S.
AU  - Milosavljević, Slobodan M.
AU  - Vajs, Vlatka
AU  - Macura, Slobodan
AU  - Todorović, Nina
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/935
AB  - From detailed study of 1D and 2D NMR spectra of ten natural 1,2-epoxyguaianolides (bis-1,2:3,4-epoxyguaianolides and guaianolide-1,2-epoxychlorohydrins), we identified general spectral traits helpful for stereochemical assignment of such sesquiterpene lactones. We found that the chemical shifts of certain H-1 and 13 C nuclei are consistently dependent on the configuration of 1,2-epoxy-ring which could be used as a simple rule for establishing this configuration. Then, from 1 D and 2D (COSY, NOESY, HMQC, HMBC) NMR data, applying the observed rule, the structure and stereochemistry of two new, diastereomeric guaianolide-1,2-epoxychlorohydrins, isolated from Achillea serbica, are determined. The NMR data, namely, nuclear overhauser enhancement (NOE) correlations, pointed out two conformations of guaianolide's cycloheptane ring. The semiempirical calculations (AM1 and PM3 methods), performed in order to gain additional information regarding conformations, resulted in three geometries of investigated lactones. Even so, the conformations derived from the NMR data agreed well with those calculated by semiempirical methods. Copyright (C) 2008 John Wiley & Sons, Ltd.
PB  - Wiley, Hoboken
T2  - Magnetic Resonance in Chemistry
T1  - Stereochemistry and conformations of natural 1,2-epoxy-guaianolides based on 1D and 2D NMR data and semiempirical calculations
VL  - 46
IS  - 5
SP  - 427
EP  - 431
DO  - 10.1002/mrc.2193
ER  - 

@article{
author = "Trifunović, Snežana S. and Milosavljević, Slobodan M. and Vajs, Vlatka and Macura, Slobodan and Todorović, Nina",
year = "2008",
abstract = "From detailed study of 1D and 2D NMR spectra of ten natural 1,2-epoxyguaianolides (bis-1,2:3,4-epoxyguaianolides and guaianolide-1,2-epoxychlorohydrins), we identified general spectral traits helpful for stereochemical assignment of such sesquiterpene lactones. We found that the chemical shifts of certain H-1 and 13 C nuclei are consistently dependent on the configuration of 1,2-epoxy-ring which could be used as a simple rule for establishing this configuration. Then, from 1 D and 2D (COSY, NOESY, HMQC, HMBC) NMR data, applying the observed rule, the structure and stereochemistry of two new, diastereomeric guaianolide-1,2-epoxychlorohydrins, isolated from Achillea serbica, are determined. The NMR data, namely, nuclear overhauser enhancement (NOE) correlations, pointed out two conformations of guaianolide's cycloheptane ring. The semiempirical calculations (AM1 and PM3 methods), performed in order to gain additional information regarding conformations, resulted in three geometries of investigated lactones. Even so, the conformations derived from the NMR data agreed well with those calculated by semiempirical methods. Copyright (C) 2008 John Wiley & Sons, Ltd.",
publisher = "Wiley, Hoboken",
journal = "Magnetic Resonance in Chemistry",
title = "Stereochemistry and conformations of natural 1,2-epoxy-guaianolides based on 1D and 2D NMR data and semiempirical calculations",
volume = "46",
number = "5",
pages = "427-431",
doi = "10.1002/mrc.2193"
}

Trifunović, S. S., Milosavljević, S. M., Vajs, V., Macura, S.,& Todorović, N.. (2008). Stereochemistry and conformations of natural 1,2-epoxy-guaianolides based on 1D and 2D NMR data and semiempirical calculations. in Magnetic Resonance in Chemistry
Wiley, Hoboken., 46(5), 427-431.
https://doi.org/10.1002/mrc.2193

Trifunović SS, Milosavljević SM, Vajs V, Macura S, Todorović N. Stereochemistry and conformations of natural 1,2-epoxy-guaianolides based on 1D and 2D NMR data and semiempirical calculations. in Magnetic Resonance in Chemistry. 2008;46(5):427-431.
doi:10.1002/mrc.2193 .

Trifunović, Snežana S., Milosavljević, Slobodan M., Vajs, Vlatka, Macura, Slobodan, Todorović, Nina, "Stereochemistry and conformations of natural 1,2-epoxy-guaianolides based on 1D and 2D NMR data and semiempirical calculations" in Magnetic Resonance in Chemistry, 46, no. 5 (2008):427-431,
https://doi.org/10.1002/mrc.2193 . .

TY  - JOUR
AU  - Vučković, Ivan M.
AU  - Trajković, Vladimir S.
AU  - Macura, Slobodan
AU  - Tešević, Vele
AU  - Janaćković, Peđa T.
AU  - Milosavljević, Slobodan M.
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/854
AB  - A new tetrahydrofuranoid lignan named seselinone was isolated from the aerial parts of Seseli annuum, together with three known lignans (eudesmin, magnone A and hernone) and prenylated coumarin umbeffiprenin. Seselinone and eudesmin showed cytotoxic activity against C6 rat glioma cell cultures. Copyright (c) 2007 John Wiley & Sons, Ltd.
PB  - John Wiley & Sons Ltd, Chichester
T2  - Phytotherapy Research
T1  - A novel cytotoxic lignan from Seseli annuum L.
VL  - 21
IS  - 8
SP  - 790
EP  - 792
DO  - 10.1002/ptr.2152
ER  - 

@article{
author = "Vučković, Ivan M. and Trajković, Vladimir S. and Macura, Slobodan and Tešević, Vele and Janaćković, Peđa T. and Milosavljević, Slobodan M.",
year = "2007",
abstract = "A new tetrahydrofuranoid lignan named seselinone was isolated from the aerial parts of Seseli annuum, together with three known lignans (eudesmin, magnone A and hernone) and prenylated coumarin umbeffiprenin. Seselinone and eudesmin showed cytotoxic activity against C6 rat glioma cell cultures. Copyright (c) 2007 John Wiley & Sons, Ltd.",
publisher = "John Wiley & Sons Ltd, Chichester",
journal = "Phytotherapy Research",
title = "A novel cytotoxic lignan from Seseli annuum L.",
volume = "21",
number = "8",
pages = "790-792",
doi = "10.1002/ptr.2152"
}

Vučković, I. M., Trajković, V. S., Macura, S., Tešević, V., Janaćković, P. T.,& Milosavljević, S. M.. (2007). A novel cytotoxic lignan from Seseli annuum L.. in Phytotherapy Research
John Wiley & Sons Ltd, Chichester., 21(8), 790-792.
https://doi.org/10.1002/ptr.2152

Vučković IM, Trajković VS, Macura S, Tešević V, Janaćković PT, Milosavljević SM. A novel cytotoxic lignan from Seseli annuum L.. in Phytotherapy Research. 2007;21(8):790-792.
doi:10.1002/ptr.2152 .

Vučković, Ivan M., Trajković, Vladimir S., Macura, Slobodan, Tešević, Vele, Janaćković, Peđa T., Milosavljević, Slobodan M., "A novel cytotoxic lignan from Seseli annuum L." in Phytotherapy Research, 21, no. 8 (2007):790-792,
https://doi.org/10.1002/ptr.2152 . .

TY  - JOUR
AU  - Đorđević, Iris
AU  - Jadranin, Milka
AU  - Vajs, Vlatka
AU  - Menkovic, Nebojsa
AU  - Tešević, Vele
AU  - Macura, Slobodan
AU  - Milosavljević, Slobodan M.
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/817
AB  - The aerial parts of Amphoricarpos neumayeri ssp. murbeckii afforded eleven guaianolides with the same relative (1 alpha H,4 beta H,5 alpha H, 7 alpha H) configuration of the basic skeleton. All of them contained a CH2OX (X = H, acetyl or isovaleroyl) group in 4 alpha-position, typical for amphoricarpolides. Four compounds (1-4) were isolated before from the same species, originating from different localities. Guaianolides 5-11 are new compounds. Compounds 7 and 8 were epoxidized at the 10 alpha(14)-position. Instead of the Delta(11(13))-double bond, observed in all previously isolated guaianolides from the same species, the four lactones contained 11 alpha,13-diol (8-10) or 11 alpha-OH, 13-chloro (11) moieties respectively.
PB  - Verlag Z Naturforsch, Tubingen
T2  - Zeitschrift fur Naturforschung. Section B: Journal of Chemical Sciences
T1  - Further guaianolides from Amphoricarpos neumayeri ssp murbeckii from Montenegro
VL  - 61
IS  - 11
SP  - 1437
EP  - 1442
DO  - 10.1515/znb-2006-1119
ER  - 

@article{
author = "Đorđević, Iris and Jadranin, Milka and Vajs, Vlatka and Menkovic, Nebojsa and Tešević, Vele and Macura, Slobodan and Milosavljević, Slobodan M.",
year = "2006",
abstract = "The aerial parts of Amphoricarpos neumayeri ssp. murbeckii afforded eleven guaianolides with the same relative (1 alpha H,4 beta H,5 alpha H, 7 alpha H) configuration of the basic skeleton. All of them contained a CH2OX (X = H, acetyl or isovaleroyl) group in 4 alpha-position, typical for amphoricarpolides. Four compounds (1-4) were isolated before from the same species, originating from different localities. Guaianolides 5-11 are new compounds. Compounds 7 and 8 were epoxidized at the 10 alpha(14)-position. Instead of the Delta(11(13))-double bond, observed in all previously isolated guaianolides from the same species, the four lactones contained 11 alpha,13-diol (8-10) or 11 alpha-OH, 13-chloro (11) moieties respectively.",
publisher = "Verlag Z Naturforsch, Tubingen",
journal = "Zeitschrift fur Naturforschung. Section B: Journal of Chemical Sciences",
title = "Further guaianolides from Amphoricarpos neumayeri ssp murbeckii from Montenegro",
volume = "61",
number = "11",
pages = "1437-1442",
doi = "10.1515/znb-2006-1119"
}

Đorđević, I., Jadranin, M., Vajs, V., Menkovic, N., Tešević, V., Macura, S.,& Milosavljević, S. M.. (2006). Further guaianolides from Amphoricarpos neumayeri ssp murbeckii from Montenegro. in Zeitschrift fur Naturforschung. Section B: Journal of Chemical Sciences
Verlag Z Naturforsch, Tubingen., 61(11), 1437-1442.
https://doi.org/10.1515/znb-2006-1119

Đorđević I, Jadranin M, Vajs V, Menkovic N, Tešević V, Macura S, Milosavljević SM. Further guaianolides from Amphoricarpos neumayeri ssp murbeckii from Montenegro. in Zeitschrift fur Naturforschung. Section B: Journal of Chemical Sciences. 2006;61(11):1437-1442.
doi:10.1515/znb-2006-1119 .

Đorđević, Iris, Jadranin, Milka, Vajs, Vlatka, Menkovic, Nebojsa, Tešević, Vele, Macura, Slobodan, Milosavljević, Slobodan M., "Further guaianolides from Amphoricarpos neumayeri ssp murbeckii from Montenegro" in Zeitschrift fur Naturforschung. Section B: Journal of Chemical Sciences, 61, no. 11 (2006):1437-1442,
https://doi.org/10.1515/znb-2006-1119 . .

TY  - JOUR
AU  - Trifunović, Snežana S.
AU  - Vajs, Vlatka
AU  - Juranić, Zorica D.
AU  - Žižak, Željko S.
AU  - Tešević, Vele
AU  - Macura, Slobodan
AU  - Milosavljević, Slobodan M.
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/779
AB  - Examination of the aerial parts of Achillea clavennae afforded eight guaianolides (1-8), three bisabolenes (9 11), four flavonols (12-15), sesamin (lignan) and isofraxidin (coumarin). The structures of the new compounds (2, 4, 5, 7 and 10) were determined by spectroscopic methods. The antiproliferative action of 2, 8, 9 and 12 were tested to HeLa, K562 and Fem-X human cancer cell lines. Guaianolides 2 (9 alpha-acetoxyartecanin) and 8 (apressin) showed significant cytotoxic effects to all tested lines and inducumenone (9) exhibited a moderate activity. The most active was flavonol centaureidin (12), already known as cytotoxic compound. (c) 2006 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Phytochemistry
T1  - Cytotoxic constituents of Achillea clavennae from Montenegro
VL  - 67
IS  - 9
SP  - 887
EP  - 893
DO  - 10.1016/j.phytochem.2006.02.026
ER  - 

@article{
author = "Trifunović, Snežana S. and Vajs, Vlatka and Juranić, Zorica D. and Žižak, Željko S. and Tešević, Vele and Macura, Slobodan and Milosavljević, Slobodan M.",
year = "2006",
abstract = "Examination of the aerial parts of Achillea clavennae afforded eight guaianolides (1-8), three bisabolenes (9 11), four flavonols (12-15), sesamin (lignan) and isofraxidin (coumarin). The structures of the new compounds (2, 4, 5, 7 and 10) were determined by spectroscopic methods. The antiproliferative action of 2, 8, 9 and 12 were tested to HeLa, K562 and Fem-X human cancer cell lines. Guaianolides 2 (9 alpha-acetoxyartecanin) and 8 (apressin) showed significant cytotoxic effects to all tested lines and inducumenone (9) exhibited a moderate activity. The most active was flavonol centaureidin (12), already known as cytotoxic compound. (c) 2006 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Phytochemistry",
title = "Cytotoxic constituents of Achillea clavennae from Montenegro",
volume = "67",
number = "9",
pages = "887-893",
doi = "10.1016/j.phytochem.2006.02.026"
}

Trifunović, S. S., Vajs, V., Juranić, Z. D., Žižak, Ž. S., Tešević, V., Macura, S.,& Milosavljević, S. M.. (2006). Cytotoxic constituents of Achillea clavennae from Montenegro. in Phytochemistry
Pergamon-Elsevier Science Ltd, Oxford., 67(9), 887-893.
https://doi.org/10.1016/j.phytochem.2006.02.026

Trifunović SS, Vajs V, Juranić ZD, Žižak ŽS, Tešević V, Macura S, Milosavljević SM. Cytotoxic constituents of Achillea clavennae from Montenegro. in Phytochemistry. 2006;67(9):887-893.
doi:10.1016/j.phytochem.2006.02.026 .

Trifunović, Snežana S., Vajs, Vlatka, Juranić, Zorica D., Žižak, Željko S., Tešević, Vele, Macura, Slobodan, Milosavljević, Slobodan M., "Cytotoxic constituents of Achillea clavennae from Montenegro" in Phytochemistry, 67, no. 9 (2006):887-893,
https://doi.org/10.1016/j.phytochem.2006.02.026 . .