Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae
Nema prikaza
Autori
Trifunović, Snežana S.Isaković, Anđelka M.
Isaković, Aleksandra J.
Vučković, Ivan M.
Mandić, Boris
Novaković, Miroslav M.
Vajs, Vlatka
Milosavljević, Slobodan M.
Trajković, Vladimir S.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Further phytochemical investigation of the aerial parts of Achillea clavennae has resulted in the isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and the iso-seco-guaianolide 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known compounds were also found, of which 9-acetoxycanin (5), sintenin (6), and oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were elucidated by combined spectroscopic methods (1D and 2DNMR, HRESIMS, CIMS, and FTIR). While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.
Ključne reči:
Achillea clavennae L. / Asteraceae / sesquiterpene lactones / iso-seco-guaianolide / NMR / cytotoxicity / apoptosisIzvor:
Planta Medica, 2014, 80, 4, 297-305Izdavač:
- Georg Thieme Verlag Kg, Stuttgart
Finansiranje / projekti:
- Bioaktivni prirodni proizvodi samoniklih, gajenih i jestivih biljaka: određivanje struktura i aktivnosti (RS-MESTD-Basic Research (BR or ON)-172053)
- Modulacija signalnih puteva koji kontrolišu intracelularni energetski balans u terapiji tumora i neuro-imuno-endokrinih poremećaja (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41025)
DOI: 10.1055/s-0033-1360312
ISSN: 0032-0943
PubMed: 24510367
WoS: 000332395000008
Scopus: 2-s2.0-84895928430
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Trifunović, Snežana S. AU - Isaković, Anđelka M. AU - Isaković, Aleksandra J. AU - Vučković, Ivan M. AU - Mandić, Boris AU - Novaković, Miroslav M. AU - Vajs, Vlatka AU - Milosavljević, Slobodan M. AU - Trajković, Vladimir S. PY - 2014 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1511 AB - Further phytochemical investigation of the aerial parts of Achillea clavennae has resulted in the isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and the iso-seco-guaianolide 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known compounds were also found, of which 9-acetoxycanin (5), sintenin (6), and oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were elucidated by combined spectroscopic methods (1D and 2DNMR, HRESIMS, CIMS, and FTIR). While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines. PB - Georg Thieme Verlag Kg, Stuttgart T2 - Planta Medica T1 - Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae VL - 80 IS - 4 SP - 297 EP - 305 DO - 10.1055/s-0033-1360312 ER -
@article{ author = "Trifunović, Snežana S. and Isaković, Anđelka M. and Isaković, Aleksandra J. and Vučković, Ivan M. and Mandić, Boris and Novaković, Miroslav M. and Vajs, Vlatka and Milosavljević, Slobodan M. and Trajković, Vladimir S.", year = "2014", abstract = "Further phytochemical investigation of the aerial parts of Achillea clavennae has resulted in the isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and the iso-seco-guaianolide 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known compounds were also found, of which 9-acetoxycanin (5), sintenin (6), and oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were elucidated by combined spectroscopic methods (1D and 2DNMR, HRESIMS, CIMS, and FTIR). While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.", publisher = "Georg Thieme Verlag Kg, Stuttgart", journal = "Planta Medica", title = "Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae", volume = "80", number = "4", pages = "297-305", doi = "10.1055/s-0033-1360312" }
Trifunović, S. S., Isaković, A. M., Isaković, A. J., Vučković, I. M., Mandić, B., Novaković, M. M., Vajs, V., Milosavljević, S. M.,& Trajković, V. S.. (2014). Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae. in Planta Medica Georg Thieme Verlag Kg, Stuttgart., 80(4), 297-305. https://doi.org/10.1055/s-0033-1360312
Trifunović SS, Isaković AM, Isaković AJ, Vučković IM, Mandić B, Novaković MM, Vajs V, Milosavljević SM, Trajković VS. Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae. in Planta Medica. 2014;80(4):297-305. doi:10.1055/s-0033-1360312 .
Trifunović, Snežana S., Isaković, Anđelka M., Isaković, Aleksandra J., Vučković, Ivan M., Mandić, Boris, Novaković, Miroslav M., Vajs, Vlatka, Milosavljević, Slobodan M., Trajković, Vladimir S., "Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae" in Planta Medica, 80, no. 4 (2014):297-305, https://doi.org/10.1055/s-0033-1360312 . .