Four sesquiterpene lactones (SLs), including three undescribed proline-SL conjugates, the guaianolides calophyllamine A and 8-epiixerisamine A, and the eudesmanolide calophyllamine B, were isolated from the methanol extract of Hieracium calophyllum R. Uechtr. (Compositae) flowering heads. Another known guaianolide, crepiside E, was detected in Hieracium L. species for the first time. Their structures were elucidated using extensive 1D and 2D NMR spectroscopy in combination with HRMS. The isolated SLs were used as external standards for qualitative and quantitative LC-MS analysis of the dry methanol extracts of the flowering aerial parts of 28 Hieracium species from the Balkan Peninsula. Guaianolides were the dominant SLs in 27 species studied. The chemosystematic significance of detected SLs was evaluated using multivariate statistics (PCA, nMDS and UPGMA). Differentiation between the main groups was well supported. All four compounds significantly and equally contributed to the differ...ences between the species. In addition, the eudesmanolide calophyllamine B could be a significant chemosystematic marker for H. sect. Villosa (Griseb.) Gremli s.l. and Glauciformia (Freyn) Zahn-Italica (Fr.) Av. Touv.
TY - JOUR
AU - Milutinović, Violeta
AU - Niketić, Marjan
AU - Krunić, Aleksej
AU - Nikolić, Dejan
AU - Petković, Miloš
AU - Ušjak, Ljuboš
AU - Petrović, Silvana
PY - 2018
UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3077
AB - Four sesquiterpene lactones (SLs), including three undescribed proline-SL conjugates, the guaianolides calophyllamine A and 8-epiixerisamine A, and the eudesmanolide calophyllamine B, were isolated from the methanol extract of Hieracium calophyllum R. Uechtr. (Compositae) flowering heads. Another known guaianolide, crepiside E, was detected in Hieracium L. species for the first time. Their structures were elucidated using extensive 1D and 2D NMR spectroscopy in combination with HRMS. The isolated SLs were used as external standards for qualitative and quantitative LC-MS analysis of the dry methanol extracts of the flowering aerial parts of 28 Hieracium species from the Balkan Peninsula. Guaianolides were the dominant SLs in 27 species studied. The chemosystematic significance of detected SLs was evaluated using multivariate statistics (PCA, nMDS and UPGMA). Differentiation between the main groups was well supported. All four compounds significantly and equally contributed to the differences between the species. In addition, the eudesmanolide calophyllamine B could be a significant chemosystematic marker for H. sect. Villosa (Griseb.) Gremli s.l. and Glauciformia (Freyn) Zahn-Italica (Fr.) Av. Touv.
PB - Pergamon-Elsevier Science Ltd, Oxford
T2 - Phytochemistry
T1 - Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance
VL - 154
SP - 19
EP - 30
DO - 10.1016/j.phytochem.2018.06.008
ER -
@article{
author = "Milutinović, Violeta and Niketić, Marjan and Krunić, Aleksej and Nikolić, Dejan and Petković, Miloš and Ušjak, Ljuboš and Petrović, Silvana",
year = "2018",
abstract = "Four sesquiterpene lactones (SLs), including three undescribed proline-SL conjugates, the guaianolides calophyllamine A and 8-epiixerisamine A, and the eudesmanolide calophyllamine B, were isolated from the methanol extract of Hieracium calophyllum R. Uechtr. (Compositae) flowering heads. Another known guaianolide, crepiside E, was detected in Hieracium L. species for the first time. Their structures were elucidated using extensive 1D and 2D NMR spectroscopy in combination with HRMS. The isolated SLs were used as external standards for qualitative and quantitative LC-MS analysis of the dry methanol extracts of the flowering aerial parts of 28 Hieracium species from the Balkan Peninsula. Guaianolides were the dominant SLs in 27 species studied. The chemosystematic significance of detected SLs was evaluated using multivariate statistics (PCA, nMDS and UPGMA). Differentiation between the main groups was well supported. All four compounds significantly and equally contributed to the differences between the species. In addition, the eudesmanolide calophyllamine B could be a significant chemosystematic marker for H. sect. Villosa (Griseb.) Gremli s.l. and Glauciformia (Freyn) Zahn-Italica (Fr.) Av. Touv.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Phytochemistry",
title = "Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance",
volume = "154",
pages = "19-30",
doi = "10.1016/j.phytochem.2018.06.008"
}
Milutinović, V., Niketić, M., Krunić, A., Nikolić, D., Petković, M., Ušjak, L.,& Petrović, S.. (2018). Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance. in Phytochemistry
Pergamon-Elsevier Science Ltd, Oxford., 154, 19-30.
https://doi.org/10.1016/j.phytochem.2018.06.008
Milutinović V, Niketić M, Krunić A, Nikolić D, Petković M, Ušjak L, Petrović S. Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance. in Phytochemistry. 2018;154:19-30.
doi:10.1016/j.phytochem.2018.06.008 .
Milutinović, Violeta, Niketić, Marjan, Krunić, Aleksej, Nikolić, Dejan, Petković, Miloš, Ušjak, Ljuboš, Petrović, Silvana, "Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance" in Phytochemistry, 154 (2018):19-30,
https://doi.org/10.1016/j.phytochem.2018.06.008 . .
