Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae
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2014
Authors
Trifunović, SnežanaIsaković, Anđelka M.
Isaković, Aleksandra
Vučković, Ivan
Mandić, Boris
Novaković, Miroslav
Vajs, Vlatka
Milosavljević, Slobodan
Trajković, Vladimir
Article (Published version)
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Show full item recordAbstract
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.
Keywords:
Achillea clavennae L. / Asteraceae / sesquiterpene lactones / iso-seco-guaianolide / NMR / cytotoxicity / apoptosisSource:
Planta Medica, 2014, 80, 4, 297-305Publisher:
- Georg Thieme Verlag Kg, Stuttgart
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-MESTD-Basic Research (BR or ON)-172053)
- Modulation of intracellular energy balance-controlling signalling pathways in therapy of cancer and neuro-immuno-endocrine disorders (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41025)
Note:
- The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/3120
DOI: 10.1055/s-0033-1360312
ISSN: 0032-0943
PubMed: 24510367
WoS: 000332395000008
Scopus: 2-s2.0-84895928430
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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/123456789/1534 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 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 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., 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 Kg, Stuttgart., 80(4), 297-305. 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):297-305. 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):297-305, https://doi.org/10.1055/s-0033-1360312 . .