Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone
Sixteen derivatives, eight of which are new compounds, were prepared from cycloartenone (1) and cycloartanone (2), and the cytotoxic activity of 14 of these compounds, together with 1 and 2, was evaluated against a panel of four cell lines. Compound 1 was obtained from the epiphyte plant Tillandsia...
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todo:paper_18743900_v21_n_p200_Zambrano2023-10-03T16:34:04Z Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone Zambrano, E.E. Casas, A.G. Di Venosa, G.M. Uriburu, M.L. Duran, F.J. Palermo, J.A. Cycloartanes Cycloartanone Cytotoxicity Synthetic derivatives Tillandsia tenuifolia 2 amino cycloart 1 en 3 one 2 chloro cycloart 1 en 3 one 2 hydroxy cycloart 1 en 3 one 2,2 dibromo cycloartan 3 one 2,2 dichloro cycloartan 3 one 2alpha azido cycloartan 3 one 2alpha chloro cycloartan 3 one 2alpha fluor cycloartan 3 one 2beta fluor cycloartan 3 one 3 benzoyl cycloart 2 ene antineoplastic agent cycloartane derivative cycloartenone derivative diosphenol doxorubicin triterpene derivative unclassified drug animal cell Article carbon nuclear magnetic resonance chemical phenomena chemoselectivity chlorination controlled study cytotoxicity cytotoxicity assay drug isolation drug synthesis heteronuclear multiple bond correlation high performance liquid chromatography human human cell hydrogenation IC50 keratinocyte cell line MCF-7 cell line nonhuman nuclear Overhauser effect priority journal proton nuclear magnetic resonance regioselectivity structure activity relation thin layer chromatography Tillandsia Tillandsia tenuifolia Sixteen derivatives, eight of which are new compounds, were prepared from cycloartenone (1) and cycloartanone (2), and the cytotoxic activity of 14 of these compounds, together with 1 and 2, was evaluated against a panel of four cell lines. Compound 1 was obtained from the epiphyte plant Tillandsia tenuifolia collected at Salta, Argentina. Due to chemoselectivity and regioselectivity problems observed in the reactions of compound 1, this substance was hydrogenated to compound 2. The attempted transformations were focused on ring A of the cited triterpenes with the aim to verify previous structure-activity relationships obtained from related compounds. The cytotoxicity results of the derivatives showed that only the diosphenol 13 displayed significant activity against all the tested cell lines. These results show that an oxidized side chain, for example an ether bridge between the side chain and ring D, is necessary for the cytotoxic activity of cycloartane derivatives. © 2017 Phytochemical Society of Europe Fil:Casas, A.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Di Venosa, G.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Duran, F.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Palermo, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_18743900_v21_n_p200_Zambrano |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Cycloartanes Cycloartanone Cytotoxicity Synthetic derivatives Tillandsia tenuifolia 2 amino cycloart 1 en 3 one 2 chloro cycloart 1 en 3 one 2 hydroxy cycloart 1 en 3 one 2,2 dibromo cycloartan 3 one 2,2 dichloro cycloartan 3 one 2alpha azido cycloartan 3 one 2alpha chloro cycloartan 3 one 2alpha fluor cycloartan 3 one 2beta fluor cycloartan 3 one 3 benzoyl cycloart 2 ene antineoplastic agent cycloartane derivative cycloartenone derivative diosphenol doxorubicin triterpene derivative unclassified drug animal cell Article carbon nuclear magnetic resonance chemical phenomena chemoselectivity chlorination controlled study cytotoxicity cytotoxicity assay drug isolation drug synthesis heteronuclear multiple bond correlation high performance liquid chromatography human human cell hydrogenation IC50 keratinocyte cell line MCF-7 cell line nonhuman nuclear Overhauser effect priority journal proton nuclear magnetic resonance regioselectivity structure activity relation thin layer chromatography Tillandsia Tillandsia tenuifolia |
| spellingShingle |
Cycloartanes Cycloartanone Cytotoxicity Synthetic derivatives Tillandsia tenuifolia 2 amino cycloart 1 en 3 one 2 chloro cycloart 1 en 3 one 2 hydroxy cycloart 1 en 3 one 2,2 dibromo cycloartan 3 one 2,2 dichloro cycloartan 3 one 2alpha azido cycloartan 3 one 2alpha chloro cycloartan 3 one 2alpha fluor cycloartan 3 one 2beta fluor cycloartan 3 one 3 benzoyl cycloart 2 ene antineoplastic agent cycloartane derivative cycloartenone derivative diosphenol doxorubicin triterpene derivative unclassified drug animal cell Article carbon nuclear magnetic resonance chemical phenomena chemoselectivity chlorination controlled study cytotoxicity cytotoxicity assay drug isolation drug synthesis heteronuclear multiple bond correlation high performance liquid chromatography human human cell hydrogenation IC50 keratinocyte cell line MCF-7 cell line nonhuman nuclear Overhauser effect priority journal proton nuclear magnetic resonance regioselectivity structure activity relation thin layer chromatography Tillandsia Tillandsia tenuifolia Zambrano, E.E. Casas, A.G. Di Venosa, G.M. Uriburu, M.L. Duran, F.J. Palermo, J.A. Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
| topic_facet |
Cycloartanes Cycloartanone Cytotoxicity Synthetic derivatives Tillandsia tenuifolia 2 amino cycloart 1 en 3 one 2 chloro cycloart 1 en 3 one 2 hydroxy cycloart 1 en 3 one 2,2 dibromo cycloartan 3 one 2,2 dichloro cycloartan 3 one 2alpha azido cycloartan 3 one 2alpha chloro cycloartan 3 one 2alpha fluor cycloartan 3 one 2beta fluor cycloartan 3 one 3 benzoyl cycloart 2 ene antineoplastic agent cycloartane derivative cycloartenone derivative diosphenol doxorubicin triterpene derivative unclassified drug animal cell Article carbon nuclear magnetic resonance chemical phenomena chemoselectivity chlorination controlled study cytotoxicity cytotoxicity assay drug isolation drug synthesis heteronuclear multiple bond correlation high performance liquid chromatography human human cell hydrogenation IC50 keratinocyte cell line MCF-7 cell line nonhuman nuclear Overhauser effect priority journal proton nuclear magnetic resonance regioselectivity structure activity relation thin layer chromatography Tillandsia Tillandsia tenuifolia |
| description |
Sixteen derivatives, eight of which are new compounds, were prepared from cycloartenone (1) and cycloartanone (2), and the cytotoxic activity of 14 of these compounds, together with 1 and 2, was evaluated against a panel of four cell lines. Compound 1 was obtained from the epiphyte plant Tillandsia tenuifolia collected at Salta, Argentina. Due to chemoselectivity and regioselectivity problems observed in the reactions of compound 1, this substance was hydrogenated to compound 2. The attempted transformations were focused on ring A of the cited triterpenes with the aim to verify previous structure-activity relationships obtained from related compounds. The cytotoxicity results of the derivatives showed that only the diosphenol 13 displayed significant activity against all the tested cell lines. These results show that an oxidized side chain, for example an ether bridge between the side chain and ring D, is necessary for the cytotoxic activity of cycloartane derivatives. © 2017 Phytochemical Society of Europe |
| format |
JOUR |
| author |
Zambrano, E.E. Casas, A.G. Di Venosa, G.M. Uriburu, M.L. Duran, F.J. Palermo, J.A. |
| author_facet |
Zambrano, E.E. Casas, A.G. Di Venosa, G.M. Uriburu, M.L. Duran, F.J. Palermo, J.A. |
| author_sort |
Zambrano, E.E. |
| title |
Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
| title_short |
Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
| title_full |
Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
| title_fullStr |
Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
| title_full_unstemmed |
Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
| title_sort |
synthesis and cytotoxicity evaluation of a-ring derivatives of cycloartanone |
| url |
http://hdl.handle.net/20.500.12110/paper_18743900_v21_n_p200_Zambrano |
| work_keys_str_mv |
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1807322183616167936 |