TY  - JOUR
AU  - Trifunović, Snežana
AU  - Milosavljević, Slobodan
AU  - Vajs, Vlatka
AU  - Macura, Slobodan
AU  - Todorović, Nina
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/476
AB  - From detailed study of ID 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 1H and 13C 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 1D 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 (AMI and PM3 methods), performed inordertogainadditional 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
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 and Milosavljević, Slobodan and Vajs, Vlatka and Macura, Slobodan and Todorović, Nina",
year = "2008",
abstract = "From detailed study of ID 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 1H and 13C 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 1D 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 (AMI and PM3 methods), performed inordertogainadditional 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",
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., Milosavljević, S., 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, 46(5), 427-431.
https://doi.org/10.1002/mrc.2193

Trifunović S, Milosavljević S, 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, Milosavljević, Slobodan, 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  - Trifunović, Snežana
AU  - Vajs, Vlatka
AU  - Juranić, Zorica
AU  - Žižak, Željko
AU  - Tešević, Vele
AU  - Macura, Slobodan
AU  - Milosavljević, Slobodan
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2713
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  - Oxford : Pergamon-Elsevier Science Ltd
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 and Vajs, Vlatka and Juranić, Zorica and Žižak, Željko and Tešević, Vele and Macura, Slobodan and Milosavljević, Slobodan",
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 = "Oxford : Pergamon-Elsevier Science Ltd",
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., Vajs, V., Juranić, Z., Žižak, Ž., Tešević, V., Macura, S.,& Milosavljević, S.. (2006). Cytotoxic constituents of Achillea clavennae from Montenegro. in Phytochemistry
Oxford : Pergamon-Elsevier Science Ltd., 67(9), 887-893.
https://doi.org/10.1016/j.phytochem.2006.02.026

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

Trifunović, Snežana, Vajs, Vlatka, Juranić, Zorica, Žižak, Željko, Tešević, Vele, Macura, Slobodan, Milosavljević, Slobodan, "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 . .

TY  - JOUR
AU  - Đorđević, Iris
AU  - Jadranin, Milka
AU  - Vajs, Vlatka
AU  - Menković, Nebojša
AU  - Tešević, Vele
AU  - Macura, Slobodan
AU  - Milosavljević, Slobodan
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2711
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 Menković, Nebojša and Tešević, Vele and Macura, Slobodan and Milosavljević, Slobodan",
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., Menković, N., Tešević, V., Macura, S.,& Milosavljević, S.. (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, Menković N, Tešević V, Macura S, Milosavljević S. 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, Menković, Nebojša, Tešević, Vele, Macura, Slobodan, Milosavljević, Slobodan, "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  - Đorđević, Iris
AU  - Vajs, Vlatka
AU  - Bulatović, V.
AU  - Menkovic, N
AU  - Tešević, Vele
AU  - Macura, S
AU  - Janaćković, Peđa T.
AU  - Milosavljević, Slobodan
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4148
AB  - Quantitative H-1 NMR measurements revealed Delta(11(13)) sesquiterpene gamma-lactones as the main constituents (greater than or equal to 1% per weight of dried plant material) in the crude extracts of the aerial parts of Amphoricarpos neumayeri ssp. neumayeri and ssp. murbeckii from mountains Orjen and Visitor (Montenegro), respectively. Preparative silica gel chromatography afforded thirteen guai-11(13)-en-12,6alpha-olides, named amphoricarpolides (1-13), with the same relative (1alphaH,4PH,5alphaH,7betaH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3beta,15-dioxygenation pattern. The only exception was 1 (3-deoxyamphoricarpolide), containing a single oxygen substituent (15-OH). Eight of them exhibited an additional oxygen substituent, 9beta-OH (5 and 6), 2alpha-OH (8-12), or 2alpha-OAc (13). Compound 7 was epoxydated at 10alpha(14)-position, whereas the remaining lactones contained a 10(14) double bond. (C) 2004 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Phytochemistry
T1  - Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro
VL  - 65
IS  - 16
SP  - 2337
EP  - 2345
DO  - 10.1016/j.phytochem.2004.07.014
ER  - 

@article{
author = "Đorđević, Iris and Vajs, Vlatka and Bulatović, V. and Menkovic, N and Tešević, Vele and Macura, S and Janaćković, Peđa T. and Milosavljević, Slobodan",
year = "2004",
abstract = "Quantitative H-1 NMR measurements revealed Delta(11(13)) sesquiterpene gamma-lactones as the main constituents (greater than or equal to 1% per weight of dried plant material) in the crude extracts of the aerial parts of Amphoricarpos neumayeri ssp. neumayeri and ssp. murbeckii from mountains Orjen and Visitor (Montenegro), respectively. Preparative silica gel chromatography afforded thirteen guai-11(13)-en-12,6alpha-olides, named amphoricarpolides (1-13), with the same relative (1alphaH,4PH,5alphaH,7betaH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3beta,15-dioxygenation pattern. The only exception was 1 (3-deoxyamphoricarpolide), containing a single oxygen substituent (15-OH). Eight of them exhibited an additional oxygen substituent, 9beta-OH (5 and 6), 2alpha-OH (8-12), or 2alpha-OAc (13). Compound 7 was epoxydated at 10alpha(14)-position, whereas the remaining lactones contained a 10(14) double bond. (C) 2004 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Phytochemistry",
title = "Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro",
volume = "65",
number = "16",
pages = "2337-2345",
doi = "10.1016/j.phytochem.2004.07.014"
}

Đorđević, I., Vajs, V., Bulatović, V., Menkovic, N., Tešević, V., Macura, S., Janaćković, P. T.,& Milosavljević, S.. (2004). Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro. in Phytochemistry
Oxford : Pergamon-Elsevier Science Ltd., 65(16), 2337-2345.
https://doi.org/10.1016/j.phytochem.2004.07.014

Đorđević I, Vajs V, Bulatović V, Menkovic N, Tešević V, Macura S, Janaćković PT, Milosavljević S. Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro. in Phytochemistry. 2004;65(16):2337-2345.
doi:10.1016/j.phytochem.2004.07.014 .

Đorđević, Iris, Vajs, Vlatka, Bulatović, V., Menkovic, N, Tešević, Vele, Macura, S, Janaćković, Peđa T., Milosavljević, Slobodan, "Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro" in Phytochemistry, 65, no. 16 (2004):2337-2345,
https://doi.org/10.1016/j.phytochem.2004.07.014 . .

TY  - JOUR
AU  - Milosavljević, Slobodan
AU  - Juranić, Ivan
AU  - Bulatovic, V
AU  - Macura, Slobodan
AU  - Juranić, Nenad
AU  - Limbach, HH
AU  - Weisz, K
AU  - Vajs, Vlatka
AU  - Todorović, Nina
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2731
AB  - Conformational analysis of 9alpha-acetoxycumambrine A 1 and 8-O-isobutiryl-9alpha-acetoxycumambrine B 2 was carried out by low-temperature NMR studies. Results suggested that lactones 1 and 2 are mixtures of two distinctive conformers, I and II. Based on low-temperature H-1 NMR spectra, in four solvents, the thermodynamic parameters of I reversible arrow II exchange process were assessed. Energy of activation of I -- gt  II reaction was obtained by dynamic NMR simulations for both compounds. Results revealed that conformational exchange of lactones 1 and 2 occurs due to "chair reversible arrow twisted chair" interconversion of a heptane ring. The same PM3 semiempirical method was applied for geometry optimization of lactones 1 and 2, as well as of 9alpha-hydroxycumambrine A 3, 9alpha-acetoxycumambrine B 4, and cumambrine B 5.
PB  - Kluwer Academic/Plenum Publ, New York
T2  - Structural Chemistry
T1  - Conformational analysis of guaianolide-type sesquiterpene lactones by low-temperature NMR spectroscopy and semiempirical calculations
VL  - 15
IS  - 3
SP  - 237
EP  - 245
DO  - 10.1023/B:STUC.0000021533.65546.57
ER  - 

@article{
author = "Milosavljević, Slobodan and Juranić, Ivan and Bulatovic, V and Macura, Slobodan and Juranić, Nenad and Limbach, HH and Weisz, K and Vajs, Vlatka and Todorović, Nina",
year = "2004",
abstract = "Conformational analysis of 9alpha-acetoxycumambrine A 1 and 8-O-isobutiryl-9alpha-acetoxycumambrine B 2 was carried out by low-temperature NMR studies. Results suggested that lactones 1 and 2 are mixtures of two distinctive conformers, I and II. Based on low-temperature H-1 NMR spectra, in four solvents, the thermodynamic parameters of I reversible arrow II exchange process were assessed. Energy of activation of I -- gt  II reaction was obtained by dynamic NMR simulations for both compounds. Results revealed that conformational exchange of lactones 1 and 2 occurs due to "chair reversible arrow twisted chair" interconversion of a heptane ring. The same PM3 semiempirical method was applied for geometry optimization of lactones 1 and 2, as well as of 9alpha-hydroxycumambrine A 3, 9alpha-acetoxycumambrine B 4, and cumambrine B 5.",
publisher = "Kluwer Academic/Plenum Publ, New York",
journal = "Structural Chemistry",
title = "Conformational analysis of guaianolide-type sesquiterpene lactones by low-temperature NMR spectroscopy and semiempirical calculations",
volume = "15",
number = "3",
pages = "237-245",
doi = "10.1023/B:STUC.0000021533.65546.57"
}

Milosavljević, S., Juranić, I., Bulatovic, V., Macura, S., Juranić, N., Limbach, H., Weisz, K., Vajs, V.,& Todorović, N.. (2004). Conformational analysis of guaianolide-type sesquiterpene lactones by low-temperature NMR spectroscopy and semiempirical calculations. in Structural Chemistry
Kluwer Academic/Plenum Publ, New York., 15(3), 237-245.
https://doi.org/10.1023/B:STUC.0000021533.65546.57

Milosavljević S, Juranić I, Bulatovic V, Macura S, Juranić N, Limbach H, Weisz K, Vajs V, Todorović N. Conformational analysis of guaianolide-type sesquiterpene lactones by low-temperature NMR spectroscopy and semiempirical calculations. in Structural Chemistry. 2004;15(3):237-245.
doi:10.1023/B:STUC.0000021533.65546.57 .

Milosavljević, Slobodan, Juranić, Ivan, Bulatovic, V, Macura, Slobodan, Juranić, Nenad, Limbach, HH, Weisz, K, Vajs, Vlatka, Todorović, Nina, "Conformational analysis of guaianolide-type sesquiterpene lactones by low-temperature NMR spectroscopy and semiempirical calculations" in Structural Chemistry, 15, no. 3 (2004):237-245,
https://doi.org/10.1023/B:STUC.0000021533.65546.57 . .

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Nevescanin, M
AU  - Macura, S
AU  - Juranic, Nenad
AU  - Menkovic, N
AU  - Milosavljević, Slobodan
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4154
AB  - Pulchellin E (1) and gaillardin (2) were isolated from the aerial parts of Inula oculus-christi, along with the flavone hispidulin. The C-13-NMR chemical shifts of 1 and 2 are reported.
PB  - Elsevier
T2  - Fitoterapia
T1  - Sesquiterpene lactones from the aerial parts of Inula oculus-christi
VL  - 74
IS  - 5
SP  - 508
EP  - 510
DO  - 10.1016/S0367-326X(03)00115-1
ER  - 

@article{
author = "Vajs, Vlatka and Nevescanin, M and Macura, S and Juranic, Nenad and Menkovic, N and Milosavljević, Slobodan",
year = "2003",
abstract = "Pulchellin E (1) and gaillardin (2) were isolated from the aerial parts of Inula oculus-christi, along with the flavone hispidulin. The C-13-NMR chemical shifts of 1 and 2 are reported.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Sesquiterpene lactones from the aerial parts of Inula oculus-christi",
volume = "74",
number = "5",
pages = "508-510",
doi = "10.1016/S0367-326X(03)00115-1"
}

Vajs, V., Nevescanin, M., Macura, S., Juranic, N., Menkovic, N.,& Milosavljević, S.. (2003). Sesquiterpene lactones from the aerial parts of Inula oculus-christi. in Fitoterapia
Elsevier., 74(5), 508-510.
https://doi.org/10.1016/S0367-326X(03)00115-1

Vajs V, Nevescanin M, Macura S, Juranic N, Menkovic N, Milosavljević S. Sesquiterpene lactones from the aerial parts of Inula oculus-christi. in Fitoterapia. 2003;74(5):508-510.
doi:10.1016/S0367-326X(03)00115-1 .

Vajs, Vlatka, Nevescanin, M, Macura, S, Juranic, Nenad, Menkovic, N, Milosavljević, Slobodan, "Sesquiterpene lactones from the aerial parts of Inula oculus-christi" in Fitoterapia, 74, no. 5 (2003):508-510,
https://doi.org/10.1016/S0367-326X(03)00115-1 . .

TY  - JOUR
AU  - Savikin-Fodulovic, K
AU  - Aljančić, Ivana
AU  - Vajs, Vlatka
AU  - Menkonic, N
AU  - Macura, S
AU  - Gojgić-Cvijović, Gordana
AU  - Milosavljević, Slobodan
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4155
AB  - As shown by quantitative 1H NMR measurements, a lipophilic extract of the aerial parts of Hypericum atomarium ssp. degenii contained a high percentage (3.1% per weight of dried plant material) of a prenylated phloroglucinol (1). Compound 1, named hyperatomarin, occurring in two tautomeric forms (1a ⇆ 1b), was isolated by bioactivity-guided preparative TLC and was identified on the basis of spectral data interpretation. This isolated phloroglucinol exhibited activity against Gram-positive (Staphyloccocus aureus and Microccocus luteus) and Gram-positive spore-forming bacteria (Bacillus subtilis and B. IP 5832).
PB  - American Chemical Society (ACS)
T2  - Journal of Natural Products
T1  - Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericum atomarium ssp degenii
VL  - 66
IS  - 9
SP  - 1236
EP  - 1238
DO  - 10.1021/np030131o
ER  - 

@article{
author = "Savikin-Fodulovic, K and Aljančić, Ivana and Vajs, Vlatka and Menkonic, N and Macura, S and Gojgić-Cvijović, Gordana and Milosavljević, Slobodan",
year = "2003",
abstract = "As shown by quantitative 1H NMR measurements, a lipophilic extract of the aerial parts of Hypericum atomarium ssp. degenii contained a high percentage (3.1% per weight of dried plant material) of a prenylated phloroglucinol (1). Compound 1, named hyperatomarin, occurring in two tautomeric forms (1a ⇆ 1b), was isolated by bioactivity-guided preparative TLC and was identified on the basis of spectral data interpretation. This isolated phloroglucinol exhibited activity against Gram-positive (Staphyloccocus aureus and Microccocus luteus) and Gram-positive spore-forming bacteria (Bacillus subtilis and B. IP 5832).",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Natural Products",
title = "Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericum atomarium ssp degenii",
volume = "66",
number = "9",
pages = "1236-1238",
doi = "10.1021/np030131o"
}

Savikin-Fodulovic, K., Aljančić, I., Vajs, V., Menkonic, N., Macura, S., Gojgić-Cvijović, G.,& Milosavljević, S.. (2003). Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericum atomarium ssp degenii. in Journal of Natural Products
American Chemical Society (ACS)., 66(9), 1236-1238.
https://doi.org/10.1021/np030131o

Savikin-Fodulovic K, Aljančić I, Vajs V, Menkonic N, Macura S, Gojgić-Cvijović G, Milosavljević S. Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericum atomarium ssp degenii. in Journal of Natural Products. 2003;66(9):1236-1238.
doi:10.1021/np030131o .

Savikin-Fodulovic, K, Aljančić, Ivana, Vajs, Vlatka, Menkonic, N, Macura, S, Gojgić-Cvijović, Gordana, Milosavljević, Slobodan, "Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericum atomarium ssp degenii" in Journal of Natural Products, 66, no. 9 (2003):1236-1238,
https://doi.org/10.1021/np030131o . .

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Vugdelija, S
AU  - Trifunović, Snežana S.
AU  - Karadžić, Ivanka M.
AU  - Juranic, N
AU  - Macura, S
AU  - Milosavljevic, Slobodan
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4156
AB  - Repeated examination of the aerial parts of Hypericum Perfomtum yielded a new degradation product of hyperforin (1) namely deoxyfurohyperforin A (2), together with the previously identified furohyperforin (3), furoadhyperforin (4), furohyperforin A (5a and 5b), pyrano[7,28-b]hyperforin (6) and 3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)-cyclohexanone (7). The antimicrobial activity of the compounds 3, 5a and 5b, 6 and 7 was tested against Staphylococcus aureus, Candida albicans, Bacillus subtilis and Escherichia coli. (C) 2003 Elsevier Science B.V. All rights reserved.
PB  - Elsevier
T2  - Fitoterapia
T1  - Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort)
VL  - 74
IS  - 5
SP  - 439
EP  - 444
DO  - 10.1016/S0367-326X(03)00114-X
ER  - 

@article{
author = "Vajs, Vlatka and Vugdelija, S and Trifunović, Snežana S. and Karadžić, Ivanka M. and Juranic, N and Macura, S and Milosavljevic, Slobodan",
year = "2003",
abstract = "Repeated examination of the aerial parts of Hypericum Perfomtum yielded a new degradation product of hyperforin (1) namely deoxyfurohyperforin A (2), together with the previously identified furohyperforin (3), furoadhyperforin (4), furohyperforin A (5a and 5b), pyrano[7,28-b]hyperforin (6) and 3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)-cyclohexanone (7). The antimicrobial activity of the compounds 3, 5a and 5b, 6 and 7 was tested against Staphylococcus aureus, Candida albicans, Bacillus subtilis and Escherichia coli. (C) 2003 Elsevier Science B.V. All rights reserved.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort)",
volume = "74",
number = "5",
pages = "439-444",
doi = "10.1016/S0367-326X(03)00114-X"
}

Vajs, V., Vugdelija, S., Trifunović, S. S., Karadžić, I. M., Juranic, N., Macura, S.,& Milosavljevic, S.. (2003). Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort). in Fitoterapia
Elsevier., 74(5), 439-444.
https://doi.org/10.1016/S0367-326X(03)00114-X

Vajs V, Vugdelija S, Trifunović SS, Karadžić IM, Juranic N, Macura S, Milosavljevic S. Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort). in Fitoterapia. 2003;74(5):439-444.
doi:10.1016/S0367-326X(03)00114-X .

Vajs, Vlatka, Vugdelija, S, Trifunović, Snežana S., Karadžić, Ivanka M., Juranic, N, Macura, S, Milosavljevic, Slobodan, "Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort)" in Fitoterapia, 74, no. 5 (2003):439-444,
https://doi.org/10.1016/S0367-326X(03)00114-X . .

TY  - JOUR
AU  - Menkovic, N
AU  - Savikin-Fodulovic, K
AU  - Bulatović, V.
AU  - Aljančić, Ivana
AU  - Juranic, N
AU  - Macura, S
AU  - Vajs, Vlatka
AU  - Milosavljević, Slobodan
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4151
AB  - Isolation of 1-O-primeverosyl-3,8-dihydroxy-5-methoxyxanthone and 1-O-gentiobiosyl- 3,7-dimethoxy-8-hydroxyxanthone, along with five known xanthones, isobellidifolin, methylbellidifolin, isoswertianin, methylswertianin and norswertianin-1-O-beta-D-glucoside, from the roots of Swertia punctata is reported. In the aerial parts four xanthones, bellidifolin, methylbellidifolin, swertianolin and mangiferin, and flavone-C-gluco side, isoorientin were identified. The chemotaxonomic and pharmacological significance of these results is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd.
T2  - Phytochemistry
T1  - Xanthones from Swertia punctata
VL  - 61
IS  - 4
SP  - 415
EP  - 420
DO  - 10.1016/S0031-9422(02)00231-5
ER  - 

@article{
author = "Menkovic, N and Savikin-Fodulovic, K and Bulatović, V. and Aljančić, Ivana and Juranic, N and Macura, S and Vajs, Vlatka and Milosavljević, Slobodan",
year = "2002",
abstract = "Isolation of 1-O-primeverosyl-3,8-dihydroxy-5-methoxyxanthone and 1-O-gentiobiosyl- 3,7-dimethoxy-8-hydroxyxanthone, along with five known xanthones, isobellidifolin, methylbellidifolin, isoswertianin, methylswertianin and norswertianin-1-O-beta-D-glucoside, from the roots of Swertia punctata is reported. In the aerial parts four xanthones, bellidifolin, methylbellidifolin, swertianolin and mangiferin, and flavone-C-gluco side, isoorientin were identified. The chemotaxonomic and pharmacological significance of these results is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd.",
journal = "Phytochemistry",
title = "Xanthones from Swertia punctata",
volume = "61",
number = "4",
pages = "415-420",
doi = "10.1016/S0031-9422(02)00231-5"
}

Menkovic, N., Savikin-Fodulovic, K., Bulatović, V., Aljančić, I., Juranic, N., Macura, S., Vajs, V.,& Milosavljević, S.. (2002). Xanthones from Swertia punctata. in Phytochemistry
Oxford : Pergamon-Elsevier Science Ltd.., 61(4), 415-420.
https://doi.org/10.1016/S0031-9422(02)00231-5

Menkovic N, Savikin-Fodulovic K, Bulatović V, Aljančić I, Juranic N, Macura S, Vajs V, Milosavljević S. Xanthones from Swertia punctata. in Phytochemistry. 2002;61(4):415-420.
doi:10.1016/S0031-9422(02)00231-5 .

Menkovic, N, Savikin-Fodulovic, K, Bulatović, V., Aljančić, Ivana, Juranic, N, Macura, S, Vajs, Vlatka, Milosavljević, Slobodan, "Xanthones from Swertia punctata" in Phytochemistry, 61, no. 4 (2002):415-420,
https://doi.org/10.1016/S0031-9422(02)00231-5 . .

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Todorović, Nina
AU  - Bulatović, V
AU  - Menković, Nebojša
AU  - Macura, Slobodan
AU  - Juranić, Nenad
AU  - Milosavljević, Slobodan
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2816
AB  - A new germacranolide, (E)-1α, 10β-epoxy-3β-acetoxy-6α-hydroxygermacra-4,11(13)-dien-12,8α-o lide, together with nine new highly oxygenated guaiadien-12,6α-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering Anthemis carpatica. In addition, six known guaianolides belonging to the same groups, also isolated previously from A. carpatica, along with two guaianolides, 2β-hydroxyepiligustrin and cumambrin B, not found before in this species, were isolated this time. (C) 2000 Elsevier Science Ltd.
PB  - Pergamon
T2  - Phytochemistry
T1  - Further sesquiterpene lactones from Anthemis carpatica
VL  - 54
IS  - 6
SP  - 625
EP  - 633
DO  - 10.1016/S0031-9422(00)00160-6
ER  - 

@article{
author = "Vajs, Vlatka and Todorović, Nina and Bulatović, V and Menković, Nebojša and Macura, Slobodan and Juranić, Nenad and Milosavljević, Slobodan",
year = "2000",
abstract = "A new germacranolide, (E)-1α, 10β-epoxy-3β-acetoxy-6α-hydroxygermacra-4,11(13)-dien-12,8α-o lide, together with nine new highly oxygenated guaiadien-12,6α-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering Anthemis carpatica. In addition, six known guaianolides belonging to the same groups, also isolated previously from A. carpatica, along with two guaianolides, 2β-hydroxyepiligustrin and cumambrin B, not found before in this species, were isolated this time. (C) 2000 Elsevier Science Ltd.",
publisher = "Pergamon",
journal = "Phytochemistry",
title = "Further sesquiterpene lactones from Anthemis carpatica",
volume = "54",
number = "6",
pages = "625-633",
doi = "10.1016/S0031-9422(00)00160-6"
}

Vajs, V., Todorović, N., Bulatović, V., Menković, N., Macura, S., Juranić, N.,& Milosavljević, S.. (2000). Further sesquiterpene lactones from Anthemis carpatica. in Phytochemistry
Pergamon., 54(6), 625-633.
https://doi.org/10.1016/S0031-9422(00)00160-6

Vajs V, Todorović N, Bulatović V, Menković N, Macura S, Juranić N, Milosavljević S. Further sesquiterpene lactones from Anthemis carpatica. in Phytochemistry. 2000;54(6):625-633.
doi:10.1016/S0031-9422(00)00160-6 .

Vajs, Vlatka, Todorović, Nina, Bulatović, V, Menković, Nebojša, Macura, Slobodan, Juranić, Nenad, Milosavljević, Slobodan, "Further sesquiterpene lactones from Anthemis carpatica" in Phytochemistry, 54, no. 6 (2000):625-633,
https://doi.org/10.1016/S0031-9422(00)00160-6 . .

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Bulatovic, V
AU  - Fodulovic-Savikin, K
AU  - Menković, Nebojša
AU  - Macura, Slobodan
AU  - Juranić, Nenad
AU  - Milosavljević, Slobodan
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2812
AB  - Two new guaianolides, i.e. anthemolide B and 8-O-angeloyl-9-O- acetylanthemolide B, in addition to 12 known closely related guaianolides were identified in the aerial parts of the flowering plant Anthemis cretica subsp. cretica.
PB  - Elsevier
T2  - Phytochemistry
T1  - Highly oxygenated guaianolides from Anthemis cretica subsp. cretica
VL  - 50
IS  - 2
SP  - 287
EP  - 291
DO  - 10.1016/S0031-9422(98)00504-4
ER  - 

@article{
author = "Vajs, Vlatka and Bulatovic, V and Fodulovic-Savikin, K and Menković, Nebojša and Macura, Slobodan and Juranić, Nenad and Milosavljević, Slobodan",
year = "1999",
abstract = "Two new guaianolides, i.e. anthemolide B and 8-O-angeloyl-9-O- acetylanthemolide B, in addition to 12 known closely related guaianolides were identified in the aerial parts of the flowering plant Anthemis cretica subsp. cretica.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Highly oxygenated guaianolides from Anthemis cretica subsp. cretica",
volume = "50",
number = "2",
pages = "287-291",
doi = "10.1016/S0031-9422(98)00504-4"
}

Vajs, V., Bulatovic, V., Fodulovic-Savikin, K., Menković, N., Macura, S., Juranić, N.,& Milosavljević, S.. (1999). Highly oxygenated guaianolides from Anthemis cretica subsp. cretica. in Phytochemistry
Elsevier., 50(2), 287-291.
https://doi.org/10.1016/S0031-9422(98)00504-4

Vajs V, Bulatovic V, Fodulovic-Savikin K, Menković N, Macura S, Juranić N, Milosavljević S. Highly oxygenated guaianolides from Anthemis cretica subsp. cretica. in Phytochemistry. 1999;50(2):287-291.
doi:10.1016/S0031-9422(98)00504-4 .

Vajs, Vlatka, Bulatovic, V, Fodulovic-Savikin, K, Menković, Nebojša, Macura, Slobodan, Juranić, Nenad, Milosavljević, Slobodan, "Highly oxygenated guaianolides from Anthemis cretica subsp. cretica" in Phytochemistry, 50, no. 2 (1999):287-291,
https://doi.org/10.1016/S0031-9422(98)00504-4 . .

TY  - JOUR
AU  - Aljančić, Ivana
AU  - Vajs, Vlatka
AU  - Menković, Nebojša
AU  - Karadžić, Ivanka
AU  - Juranić, Nenad
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2809
AB  - Four flavones (1-4) and nine sesquiterpene lactones (5-13), one of them (5) a new compound, were isolated from the aerial parts of Achillea atrata L. subsp, multifida. Although the crude extract demonstrated in vitro inhibitory activity against Candida albicans and Bacillus subtilis, all isolated flavones were active against B. subtilis. Flavones 1, 2, and 3 were also active against C. albicans, while 1 and 3 exhibited activity against E. coli, as well. None of the tested lactones (7, 9, 12, and 13) showed any antimicrobial activity.
PB  - American Chemical Society (ACS)
T2  - Journal of Natural Products
T1  - Flavones and sesquiterpene lactones from Achillea atrata subsp, multifida: Antimicrobial activity
VL  - 62
IS  - 6
SP  - 909
EP  - 911
DO  - 10.1021/np980536m
ER  - 

@article{
author = "Aljančić, Ivana and Vajs, Vlatka and Menković, Nebojša and Karadžić, Ivanka and Juranić, Nenad and Milosavljević, Slobodan and Macura, Slobodan",
year = "1999",
abstract = "Four flavones (1-4) and nine sesquiterpene lactones (5-13), one of them (5) a new compound, were isolated from the aerial parts of Achillea atrata L. subsp, multifida. Although the crude extract demonstrated in vitro inhibitory activity against Candida albicans and Bacillus subtilis, all isolated flavones were active against B. subtilis. Flavones 1, 2, and 3 were also active against C. albicans, while 1 and 3 exhibited activity against E. coli, as well. None of the tested lactones (7, 9, 12, and 13) showed any antimicrobial activity.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Natural Products",
title = "Flavones and sesquiterpene lactones from Achillea atrata subsp, multifida: Antimicrobial activity",
volume = "62",
number = "6",
pages = "909-911",
doi = "10.1021/np980536m"
}

Aljančić, I., Vajs, V., Menković, N., Karadžić, I., Juranić, N., Milosavljević, S.,& Macura, S.. (1999). Flavones and sesquiterpene lactones from Achillea atrata subsp, multifida: Antimicrobial activity. in Journal of Natural Products
American Chemical Society (ACS)., 62(6), 909-911.
https://doi.org/10.1021/np980536m

Aljančić I, Vajs V, Menković N, Karadžić I, Juranić N, Milosavljević S, Macura S. Flavones and sesquiterpene lactones from Achillea atrata subsp, multifida: Antimicrobial activity. in Journal of Natural Products. 1999;62(6):909-911.
doi:10.1021/np980536m .

Aljančić, Ivana, Vajs, Vlatka, Menković, Nebojša, Karadžić, Ivanka, Juranić, Nenad, Milosavljević, Slobodan, Macura, Slobodan, "Flavones and sesquiterpene lactones from Achillea atrata subsp, multifida: Antimicrobial activity" in Journal of Natural Products, 62, no. 6 (1999):909-911,
https://doi.org/10.1021/np980536m . .

TY  - JOUR
AU  - Trifunović, Snežana
AU  - Vajs, Vlatka
AU  - Macura, Slobodan
AU  - Juranić, Nenad
AU  - Djarmati, Z
AU  - Jankov, Ratko
AU  - Milosavljević, Slobodan
PY  - 1998
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2807
AB  - The isolation of two oxidation products of hyperforin from the aerial parts of Hypericum perforatum and their structure determination by means of 2D NMR methods is reported. The products had the same 1-(2-methyl-1- oxopropyl)-2,12-dioxo-3,10β-bis(3-methyl-2-butenyl)-11β-methyl-11α-(4- methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0 4,8 ]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C 35 H 52 O 5 ), contained a 1-methyl-1-hydroxyethyl group in the 6β- position, whereas the other compound (a hemiacetal, C 32 H 46 O 5 ), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6α- and 6β-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.
PB  - Elsevier
T2  - Phytochemistry
T1  - Oxidation products of hyperforin from Hypericum perforatum
VL  - 49
IS  - 5
SP  - 1305
EP  - 1310
DO  - 10.1016/S0031-9422(97)00903-5
ER  - 

@article{
author = "Trifunović, Snežana and Vajs, Vlatka and Macura, Slobodan and Juranić, Nenad and Djarmati, Z and Jankov, Ratko and Milosavljević, Slobodan",
year = "1998",
abstract = "The isolation of two oxidation products of hyperforin from the aerial parts of Hypericum perforatum and their structure determination by means of 2D NMR methods is reported. The products had the same 1-(2-methyl-1- oxopropyl)-2,12-dioxo-3,10β-bis(3-methyl-2-butenyl)-11β-methyl-11α-(4- methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0 4,8 ]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C 35 H 52 O 5 ), contained a 1-methyl-1-hydroxyethyl group in the 6β- position, whereas the other compound (a hemiacetal, C 32 H 46 O 5 ), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6α- and 6β-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Oxidation products of hyperforin from Hypericum perforatum",
volume = "49",
number = "5",
pages = "1305-1310",
doi = "10.1016/S0031-9422(97)00903-5"
}

Trifunović, S., Vajs, V., Macura, S., Juranić, N., Djarmati, Z., Jankov, R.,& Milosavljević, S.. (1998). Oxidation products of hyperforin from Hypericum perforatum. in Phytochemistry
Elsevier., 49(5), 1305-1310.
https://doi.org/10.1016/S0031-9422(97)00903-5

Trifunović S, Vajs V, Macura S, Juranić N, Djarmati Z, Jankov R, Milosavljević S. Oxidation products of hyperforin from Hypericum perforatum. in Phytochemistry. 1998;49(5):1305-1310.
doi:10.1016/S0031-9422(97)00903-5 .

Trifunović, Snežana, Vajs, Vlatka, Macura, Slobodan, Juranić, Nenad, Djarmati, Z, Jankov, Ratko, Milosavljević, Slobodan, "Oxidation products of hyperforin from Hypericum perforatum" in Phytochemistry, 49, no. 5 (1998):1305-1310,
https://doi.org/10.1016/S0031-9422(97)00903-5 . .

TY  - JOUR
AU  - Bulatovic, V
AU  - Vajs, Vlatka
AU  - Macura, Slobodan
AU  - Juranić, Nenad
AU  - Milosavljević, Slobodan
PY  - 1997
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2802
AB  - Twelve new guaianolides, (1-12), six of them (2-5, 9 and 12) containing a hydroperoxy function, were isolated from the aerial parts of the flowering plant Anthemis carpatica. Their structures were elucidated by spectroscopic methods including 2D NMR experiments.
PB  - American Chemical Society (ACS)
T2  - Journal of Natural Products
T1  - Highly oxygenated guaianolides from Anthemis carpatica
VL  - 60
IS  - 12
SP  - 1222
EP  - 1228
DO  - 10.1021/np970185w
ER  - 

@article{
author = "Bulatovic, V and Vajs, Vlatka and Macura, Slobodan and Juranić, Nenad and Milosavljević, Slobodan",
year = "1997",
abstract = "Twelve new guaianolides, (1-12), six of them (2-5, 9 and 12) containing a hydroperoxy function, were isolated from the aerial parts of the flowering plant Anthemis carpatica. Their structures were elucidated by spectroscopic methods including 2D NMR experiments.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Natural Products",
title = "Highly oxygenated guaianolides from Anthemis carpatica",
volume = "60",
number = "12",
pages = "1222-1228",
doi = "10.1021/np970185w"
}

Bulatovic, V., Vajs, V., Macura, S., Juranić, N.,& Milosavljević, S.. (1997). Highly oxygenated guaianolides from Anthemis carpatica. in Journal of Natural Products
American Chemical Society (ACS)., 60(12), 1222-1228.
https://doi.org/10.1021/np970185w

Bulatovic V, Vajs V, Macura S, Juranić N, Milosavljević S. Highly oxygenated guaianolides from Anthemis carpatica. in Journal of Natural Products. 1997;60(12):1222-1228.
doi:10.1021/np970185w .

Bulatovic, V, Vajs, Vlatka, Macura, Slobodan, Juranić, Nenad, Milosavljević, Slobodan, "Highly oxygenated guaianolides from Anthemis carpatica" in Journal of Natural Products, 60, no. 12 (1997):1222-1228,
https://doi.org/10.1021/np970185w . .

TY  - JOUR
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
AU  - Stefanović, Milutin
AU  - Aljančić, Ivana
AU  - Milinković, Darinka
PY  - 1994
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4375
AB  - The isolation of three highly oxygenated guaianolides, desacetyl-1α-4α- dihydroxybishopsolicepolide [1], its 4β-hydroxy epimer 2 (a new compound), and 1β,2β:3β,4β-diepoxy-8α,10α-dihydroxyguai-12(13)-en-12,6α-olide [3], from the aerial parts of Achillea crithmifolia is reported. Because lactone 3 was shown to be identical with rupin A, the initially proposed 1α,2α:3α,4α-diepoxy stereochemistry of rupin A should be revised.
PB  - American Chemical Society
T2  - Journal of Natural Products
T1  - Sesquiterpene lactones from Achillea crithmifolia
VL  - 57
IS  - 1
SP  - 64
EP  - 67
DO  - 10.1021/np50103a008
ER  - 

@article{
author = "Milosavljević, Slobodan and Macura, Slobodan and Stefanović, Milutin and Aljančić, Ivana and Milinković, Darinka",
year = "1994",
abstract = "The isolation of three highly oxygenated guaianolides, desacetyl-1α-4α- dihydroxybishopsolicepolide [1], its 4β-hydroxy epimer 2 (a new compound), and 1β,2β:3β,4β-diepoxy-8α,10α-dihydroxyguai-12(13)-en-12,6α-olide [3], from the aerial parts of Achillea crithmifolia is reported. Because lactone 3 was shown to be identical with rupin A, the initially proposed 1α,2α:3α,4α-diepoxy stereochemistry of rupin A should be revised.",
publisher = "American Chemical Society",
journal = "Journal of Natural Products",
title = "Sesquiterpene lactones from Achillea crithmifolia",
volume = "57",
number = "1",
pages = "64-67",
doi = "10.1021/np50103a008"
}

Milosavljević, S., Macura, S., Stefanović, M., Aljančić, I.,& Milinković, D.. (1994). Sesquiterpene lactones from Achillea crithmifolia. in Journal of Natural Products
American Chemical Society., 57(1), 64-67.
https://doi.org/10.1021/np50103a008

Milosavljević S, Macura S, Stefanović M, Aljančić I, Milinković D. Sesquiterpene lactones from Achillea crithmifolia. in Journal of Natural Products. 1994;57(1):64-67.
doi:10.1021/np50103a008 .

Milosavljević, Slobodan, Macura, Slobodan, Stefanović, Milutin, Aljančić, Ivana, Milinković, Darinka, "Sesquiterpene lactones from Achillea crithmifolia" in Journal of Natural Products, 57, no. 1 (1994):64-67,
https://doi.org/10.1021/np50103a008 . .

TY  - JOUR
AU  - Milosavljević, Slobodan
AU  - Aljančić, Ivana
AU  - Macura, Slobodan
AU  - Milinković, Darinka
AU  - Stefanović, Milutin
PY  - 1991
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4376
AB  - The isolation of guaianolides rupicolin-A, rupicolin-B, their acetates and a new germacranolide 1β,10α-epoxy-3β,9β-diacetoxy-11α,13-dihydrocostunolide, identified by means of PS DQF COSY and PS NOESY, from Achillea crithmifolia is reported. A flavonoid jaceidin was also isolated from the same extract.
PB  - Elsevier
T2  - Phytochemistry
T1  - Sesquiterpene lactones from Achillea crithmifolia
VL  - 30
IS  - 10
SP  - 3464
EP  - 3466
DO  - 10.1016/0031-9422(91)83232-A
ER  - 

@article{
author = "Milosavljević, Slobodan and Aljančić, Ivana and Macura, Slobodan and Milinković, Darinka and Stefanović, Milutin",
year = "1991",
abstract = "The isolation of guaianolides rupicolin-A, rupicolin-B, their acetates and a new germacranolide 1β,10α-epoxy-3β,9β-diacetoxy-11α,13-dihydrocostunolide, identified by means of PS DQF COSY and PS NOESY, from Achillea crithmifolia is reported. A flavonoid jaceidin was also isolated from the same extract.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Sesquiterpene lactones from Achillea crithmifolia",
volume = "30",
number = "10",
pages = "3464-3466",
doi = "10.1016/0031-9422(91)83232-A"
}

Milosavljević, S., Aljančić, I., Macura, S., Milinković, D.,& Stefanović, M.. (1991). Sesquiterpene lactones from Achillea crithmifolia. in Phytochemistry
Elsevier., 30(10), 3464-3466.
https://doi.org/10.1016/0031-9422(91)83232-A

Milosavljević S, Aljančić I, Macura S, Milinković D, Stefanović M. Sesquiterpene lactones from Achillea crithmifolia. in Phytochemistry. 1991;30(10):3464-3466.
doi:10.1016/0031-9422(91)83232-A .

Milosavljević, Slobodan, Aljančić, Ivana, Macura, Slobodan, Milinković, Darinka, Stefanović, Milutin, "Sesquiterpene lactones from Achillea crithmifolia" in Phytochemistry, 30, no. 10 (1991):3464-3466,
https://doi.org/10.1016/0031-9422(91)83232-A . .

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Jeremić, Dragoslav
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
PY  - 1989
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2792
AB  - The isolation of 11(13)-dehydrocriolin [a germacranolide also known as 11(13)-dehydroivaxillin], 2α-hydroxyalantolactone, 4α,5α-epoxy-10α,14-H-inuviscolide (the major component) and carabrone from the aerial parts of Inula helenium is reported. The first two lactones were isolated for the first time from this plant. © 1989.
PB  - Pergamon Press
T2  - Phytochemistry
T1  - Sesquiterpene lactones from Inula helenium
VL  - 28
IS  - 6
SP  - 1763
EP  - 1764
DO  - 10.1016/S0031-9422(00)97842-7
ER  - 

@article{
author = "Vajs, Vlatka and Jeremić, Dragoslav and Milosavljević, Slobodan and Macura, Slobodan",
year = "1989",
abstract = "The isolation of 11(13)-dehydrocriolin [a germacranolide also known as 11(13)-dehydroivaxillin], 2α-hydroxyalantolactone, 4α,5α-epoxy-10α,14-H-inuviscolide (the major component) and carabrone from the aerial parts of Inula helenium is reported. The first two lactones were isolated for the first time from this plant. © 1989.",
publisher = "Pergamon Press",
journal = "Phytochemistry",
title = "Sesquiterpene lactones from Inula helenium",
volume = "28",
number = "6",
pages = "1763-1764",
doi = "10.1016/S0031-9422(00)97842-7"
}

Vajs, V., Jeremić, D., Milosavljević, S.,& Macura, S.. (1989). Sesquiterpene lactones from Inula helenium. in Phytochemistry
Pergamon Press., 28(6), 1763-1764.
https://doi.org/10.1016/S0031-9422(00)97842-7

Vajs V, Jeremić D, Milosavljević S, Macura S. Sesquiterpene lactones from Inula helenium. in Phytochemistry. 1989;28(6):1763-1764.
doi:10.1016/S0031-9422(00)97842-7 .

Vajs, Vlatka, Jeremić, Dragoslav, Milosavljević, Slobodan, Macura, Slobodan, "Sesquiterpene lactones from Inula helenium" in Phytochemistry, 28, no. 6 (1989):1763-1764,
https://doi.org/10.1016/S0031-9422(00)97842-7 . .

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Jeremić, Dragoslav
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
PY  - 1987
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2784
AB  - The application of two‐dimensional NOE NMR spectroscopy (NOESY) for the stereochemical assignment of isomeric 14‐acetoxy‐13‐hydroxy‐ and 13‐acetoxy‐14‐hydroxy‐5,6‐caryophyllen‐7‐ones, and their acetylation products, is reported. Copyright © 1987 John Wiley & Sons Ltd.
PB  - John Wiley & Sons Ltd.
T2  - Magnetic Resonance in Chemistry
T1  - Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia
VL  - 25
IS  - 10
SP  - 889
EP  - 891
DO  - 10.1002/mrc.1260251012
ER  - 

@article{
author = "Vajs, Vlatka and Jeremić, Dragoslav and Milosavljević, Slobodan and Macura, Slobodan",
year = "1987",
abstract = "The application of two‐dimensional NOE NMR spectroscopy (NOESY) for the stereochemical assignment of isomeric 14‐acetoxy‐13‐hydroxy‐ and 13‐acetoxy‐14‐hydroxy‐5,6‐caryophyllen‐7‐ones, and their acetylation products, is reported. Copyright © 1987 John Wiley & Sons Ltd.",
publisher = "John Wiley & Sons Ltd.",
journal = "Magnetic Resonance in Chemistry",
title = "Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia",
volume = "25",
number = "10",
pages = "889-891",
doi = "10.1002/mrc.1260251012"
}

Vajs, V., Jeremić, D., Milosavljević, S.,& Macura, S.. (1987). Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia. in Magnetic Resonance in Chemistry
John Wiley & Sons Ltd.., 25(10), 889-891.
https://doi.org/10.1002/mrc.1260251012

Vajs V, Jeremić D, Milosavljević S, Macura S. Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia. in Magnetic Resonance in Chemistry. 1987;25(10):889-891.
doi:10.1002/mrc.1260251012 .

Vajs, Vlatka, Jeremić, Dragoslav, Milosavljević, Slobodan, Macura, Slobodan, "Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia" in Magnetic Resonance in Chemistry, 25, no. 10 (1987):889-891,
https://doi.org/10.1002/mrc.1260251012 . .

TY  - JOUR
AU  - Jeremić, Dragoslav
AU  - Macura, Slobodan
AU  - Milosavljević, Slobodan
AU  - Vajs, Vlatka
PY  - 1985
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2786
AB  - Identification of a novel trioxygenated Δ8(9),15_ pimaric acid methyl ester from plant species Lycopus europaeus by means of two-dimensional 1H NMR spectroscopy (COSY and NOESY) is reported. © 1985.
PB  - Pergamon Press
T2  - Tetrahedron
T1  - A novel pimara-8(9),15-diene from lycopus europaeus
VL  - 41
IS  - 2
SP  - 357
EP  - 364
DO  - 10.1016/S0040-4020(01)96427-0
ER  - 

@article{
author = "Jeremić, Dragoslav and Macura, Slobodan and Milosavljević, Slobodan and Vajs, Vlatka",
year = "1985",
abstract = "Identification of a novel trioxygenated Δ8(9),15_ pimaric acid methyl ester from plant species Lycopus europaeus by means of two-dimensional 1H NMR spectroscopy (COSY and NOESY) is reported. © 1985.",
publisher = "Pergamon Press",
journal = "Tetrahedron",
title = "A novel pimara-8(9),15-diene from lycopus europaeus",
volume = "41",
number = "2",
pages = "357-364",
doi = "10.1016/S0040-4020(01)96427-0"
}

Jeremić, D., Macura, S., Milosavljević, S.,& Vajs, V.. (1985). A novel pimara-8(9),15-diene from lycopus europaeus. in Tetrahedron
Pergamon Press., 41(2), 357-364.
https://doi.org/10.1016/S0040-4020(01)96427-0

Jeremić D, Macura S, Milosavljević S, Vajs V. A novel pimara-8(9),15-diene from lycopus europaeus. in Tetrahedron. 1985;41(2):357-364.
doi:10.1016/S0040-4020(01)96427-0 .

Jeremić, Dragoslav, Macura, Slobodan, Milosavljević, Slobodan, Vajs, Vlatka, "A novel pimara-8(9),15-diene from lycopus europaeus" in Tetrahedron, 41, no. 2 (1985):357-364,
https://doi.org/10.1016/S0040-4020(01)96427-0 . .

TY  - JOUR
AU  - Vitorović, Dragomir K.
AU  - Vučelić, D.
AU  - Gašič, M. J.
AU  - Juranić, Nenad
AU  - Macura, Slobodan
PY  - 1978
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2760
AB  - 13C NMR spectroscopy was applied in the investigation of the structure of the organic matter in oil shales. By using Proton Enhanced Nuclear Induction Spectroscopy, a fair resolution of aliphatic and aromatic carbon signals was achieved. This method provided information on the relative ratio of aliphatic and aromatic carbons within a given set of samples (Aleksinac, Kimmeridge, Colorado, Australian torbanite and Estonian kukersite). © 1978.
PB  - Pergamon Press
T2  - Organic Geochemistry
T1  - Analysis of the organic matter of oil shales by nuclear magnetic resonance
VL  - 1
IS  - 2
SP  - 89
EP  - 91
DO  - 10.1016/0146-6380(78)90005-0
ER  - 

@article{
author = "Vitorović, Dragomir K. and Vučelić, D. and Gašič, M. J. and Juranić, Nenad and Macura, Slobodan",
year = "1978",
abstract = "13C NMR spectroscopy was applied in the investigation of the structure of the organic matter in oil shales. By using Proton Enhanced Nuclear Induction Spectroscopy, a fair resolution of aliphatic and aromatic carbon signals was achieved. This method provided information on the relative ratio of aliphatic and aromatic carbons within a given set of samples (Aleksinac, Kimmeridge, Colorado, Australian torbanite and Estonian kukersite). © 1978.",
publisher = "Pergamon Press",
journal = "Organic Geochemistry",
title = "Analysis of the organic matter of oil shales by nuclear magnetic resonance",
volume = "1",
number = "2",
pages = "89-91",
doi = "10.1016/0146-6380(78)90005-0"
}

Vitorović, D. K., Vučelić, D., Gašič, M. J., Juranić, N.,& Macura, S.. (1978). Analysis of the organic matter of oil shales by nuclear magnetic resonance. in Organic Geochemistry
Pergamon Press., 1(2), 89-91.
https://doi.org/10.1016/0146-6380(78)90005-0

Vitorović DK, Vučelić D, Gašič MJ, Juranić N, Macura S. Analysis of the organic matter of oil shales by nuclear magnetic resonance. in Organic Geochemistry. 1978;1(2):89-91.
doi:10.1016/0146-6380(78)90005-0 .

Vitorović, Dragomir K., Vučelić, D., Gašič, M. J., Juranić, Nenad, Macura, Slobodan, "Analysis of the organic matter of oil shales by nuclear magnetic resonance" in Organic Geochemistry, 1, no. 2 (1978):89-91,
https://doi.org/10.1016/0146-6380(78)90005-0 . .