Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae
Authors
Trifunović, Snežana
Isaković, Anđelka M.

Isaković, Aleksandra

Vučković, Ivan

Mandić, Boris

Novaković, Miroslav

Vajs, Vlatka
Milosavljević, Slobodan

Trajković, Vladimir

Article (Accepted Version)
Metadata
Show full item recordAbstract
Further phytochemical investigation into the aerial parts of Achillea clavennae has resulted in the 3 isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and 4 the iso-seco-guaianolide, 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known 5 compounds were also found in this plant species, of which 9 α -acetoxycanin (5), sintenin (6) and 6 oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were 7 elucidated by combined spectroscopic methods (1D and 2D NMR, HRESIMS, CIMS, FTIR). 8 While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-9 seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone 10 apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.
Keywords:
Chemosystematics / Natural ProductsSource:
Planta medica, 2014, 80, 4, 275-305Publisher:
- Georg Thieme Verlag
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
Note:
- This is the peer-reviewed version of the article: https://dx.doi.org/10.1055/s-0033-1360312
- http://cer.ihtm.bg.ac.rs/handle/123456789/1534
DOI: 10.1055/s-0033-1360312
ISSN: 0032-0943
WoS: 000332395000008
Scopus: 2-s2.0-84895928430
Collections
Institution/Community
IHTMTY - JOUR AU - Trifunović, Snežana AU - Isaković, Anđelka M. AU - Isaković, Aleksandra AU - Vučković, Ivan AU - Mandić, Boris AU - Novaković, Miroslav AU - Vajs, Vlatka AU - Milosavljević, Slobodan AU - Trajković, Vladimir PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3120 AB - Further phytochemical investigation into the aerial parts of Achillea clavennae has resulted in the 3 isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and 4 the iso-seco-guaianolide, 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known 5 compounds were also found in this plant species, of which 9 α -acetoxycanin (5), sintenin (6) and 6 oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were 7 elucidated by combined spectroscopic methods (1D and 2D NMR, HRESIMS, CIMS, FTIR). 8 While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-9 seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone 10 apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines. PB - Georg Thieme Verlag T2 - Planta medica T1 - Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae VL - 80 IS - 4 SP - 275 EP - 305 DO - 10.1055/s-0033-1360312 ER -
@article{ author = "Trifunović, Snežana and Isaković, Anđelka M. and Isaković, Aleksandra and Vučković, Ivan and Mandić, Boris and Novaković, Miroslav and Vajs, Vlatka and Milosavljević, Slobodan and Trajković, Vladimir", year = "2014", abstract = "Further phytochemical investigation into the aerial parts of Achillea clavennae has resulted in the 3 isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and 4 the iso-seco-guaianolide, 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known 5 compounds were also found in this plant species, of which 9 α -acetoxycanin (5), sintenin (6) and 6 oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were 7 elucidated by combined spectroscopic methods (1D and 2D NMR, HRESIMS, CIMS, FTIR). 8 While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-9 seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone 10 apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.", publisher = "Georg Thieme Verlag", journal = "Planta medica", title = "Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae", volume = "80", number = "4", pages = "275-305", doi = "10.1055/s-0033-1360312" }
Trifunović, S., Isaković, A. M., Isaković, A., Vučković, I., Mandić, B., Novaković, M., Vajs, V., Milosavljević, S.,& Trajković, V.. (2014). Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae. in Planta medica Georg Thieme Verlag., 80(4), 275-305. https://doi.org/10.1055/s-0033-1360312
Trifunović S, Isaković AM, Isaković A, Vučković I, Mandić B, Novaković M, Vajs V, Milosavljević S, Trajković V. Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae. in Planta medica. 2014;80(4):275-305. doi:10.1055/s-0033-1360312 .
Trifunović, Snežana, Isaković, Anđelka M., Isaković, Aleksandra, Vučković, Ivan, Mandić, Boris, Novaković, Miroslav, Vajs, Vlatka, Milosavljević, Slobodan, Trajković, Vladimir, "Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae" in Planta medica, 80, no. 4 (2014):275-305, https://doi.org/10.1055/s-0033-1360312 . .