Sesquiterpene lactones from the extracts of two Balkan endemic Laserpitium species and their cytotoxic activity
Само за регистроване кориснике
2013
Аутори
Popović, VišnjaHeyerick, Arne
Petrović, Silvana
Van Calenbergh, Serge
Karalić, Izet
Niketić, Marjan
Deforce, Dieter
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Chloroform extracts of the underground parts of two Balkan endemic Laserpitium species, Laserpitium zernyi Hayek and Laserpitium ochridanum Micevski, were chemically investigated. Five unknown guaianolides from the class of slovanolides, of which four were additionally 2 beta-esterified, as well as two lactones, previously identified in other Laserpitium species, were isolated from the L. ochridanum extract. From the L. zernyi extract one slovanolide derivative was isolated for the first time in the genus Laserpitium. In addition, the phenylpropanoid latifolone and six known sesquiterpene lactones, characterised as derivatives of slovanolide and silerolide, were isolated from the extracts of both species. The cytotoxic activities of the total extracts and the isolated compounds were tested using MTT and SRB assays on the two human breast cancer cell lines, MCF 7/6 and MCF 7/AZ. The extracts exerted cytotoxic activities with the IC50 values ranging 65.21-348.25 mu g/mL. The L ochridanum... extract was most potent in the MTT test with IC50 values of 65.21 and 66.09 mu g/mL in the MCF 7/AZ and MCF 7/6 cell lines, respectively. The highest cytotoxic activity exerted 2 beta,8 alpha-di-angeloyloxy-10 beta-hydroxy-6 alpha H-guaian-3,(7-11)-dien-12,6-olide, a slovanolide derivative with an additional double bond in lactone ring, on highly invasive MCF 7/6 cell line, with IC50 value 0.7 mu M in both assays tested. Generally, guaianolides with a higher number of ester moieties at the positions 2 beta, 8 alpha, 10 beta or 11 alpha exhibited IC50 values in the micromolar range, while eudesmanolides and guaianolides with a lower number of esters did not induce significant cytotoxicity.
Кључне речи:
Laserpitium zernyi / Laserpitium ochridanum / Apiaceae / Structure elucidation / Guaianolides / Slovanolides / Eudesmanolides / Cytotoxic activityИзвор:
Phytochemistry, 2013, 87, 102-111Издавач:
- Pergamon-Elsevier Science Ltd, Oxford
Финансирање / пројекти:
- Erasmus Mundus Action 2 program of European Comission, no. 1011092
DOI: 10.1016/j.phytochem.2012.11.011
ISSN: 0031-9422
PubMed: 23246199
WoS: 000315078900012
Scopus: 2-s2.0-84872761685
Институција/група
PharmacyTY - JOUR AU - Popović, Višnja AU - Heyerick, Arne AU - Petrović, Silvana AU - Van Calenbergh, Serge AU - Karalić, Izet AU - Niketić, Marjan AU - Deforce, Dieter PY - 2013 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1954 AB - Chloroform extracts of the underground parts of two Balkan endemic Laserpitium species, Laserpitium zernyi Hayek and Laserpitium ochridanum Micevski, were chemically investigated. Five unknown guaianolides from the class of slovanolides, of which four were additionally 2 beta-esterified, as well as two lactones, previously identified in other Laserpitium species, were isolated from the L. ochridanum extract. From the L. zernyi extract one slovanolide derivative was isolated for the first time in the genus Laserpitium. In addition, the phenylpropanoid latifolone and six known sesquiterpene lactones, characterised as derivatives of slovanolide and silerolide, were isolated from the extracts of both species. The cytotoxic activities of the total extracts and the isolated compounds were tested using MTT and SRB assays on the two human breast cancer cell lines, MCF 7/6 and MCF 7/AZ. The extracts exerted cytotoxic activities with the IC50 values ranging 65.21-348.25 mu g/mL. The L ochridanum extract was most potent in the MTT test with IC50 values of 65.21 and 66.09 mu g/mL in the MCF 7/AZ and MCF 7/6 cell lines, respectively. The highest cytotoxic activity exerted 2 beta,8 alpha-di-angeloyloxy-10 beta-hydroxy-6 alpha H-guaian-3,(7-11)-dien-12,6-olide, a slovanolide derivative with an additional double bond in lactone ring, on highly invasive MCF 7/6 cell line, with IC50 value 0.7 mu M in both assays tested. Generally, guaianolides with a higher number of ester moieties at the positions 2 beta, 8 alpha, 10 beta or 11 alpha exhibited IC50 values in the micromolar range, while eudesmanolides and guaianolides with a lower number of esters did not induce significant cytotoxicity. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Phytochemistry T1 - Sesquiterpene lactones from the extracts of two Balkan endemic Laserpitium species and their cytotoxic activity VL - 87 SP - 102 EP - 111 DO - 10.1016/j.phytochem.2012.11.011 ER -
@article{ author = "Popović, Višnja and Heyerick, Arne and Petrović, Silvana and Van Calenbergh, Serge and Karalić, Izet and Niketić, Marjan and Deforce, Dieter", year = "2013", abstract = "Chloroform extracts of the underground parts of two Balkan endemic Laserpitium species, Laserpitium zernyi Hayek and Laserpitium ochridanum Micevski, were chemically investigated. Five unknown guaianolides from the class of slovanolides, of which four were additionally 2 beta-esterified, as well as two lactones, previously identified in other Laserpitium species, were isolated from the L. ochridanum extract. From the L. zernyi extract one slovanolide derivative was isolated for the first time in the genus Laserpitium. In addition, the phenylpropanoid latifolone and six known sesquiterpene lactones, characterised as derivatives of slovanolide and silerolide, were isolated from the extracts of both species. The cytotoxic activities of the total extracts and the isolated compounds were tested using MTT and SRB assays on the two human breast cancer cell lines, MCF 7/6 and MCF 7/AZ. The extracts exerted cytotoxic activities with the IC50 values ranging 65.21-348.25 mu g/mL. The L ochridanum extract was most potent in the MTT test with IC50 values of 65.21 and 66.09 mu g/mL in the MCF 7/AZ and MCF 7/6 cell lines, respectively. The highest cytotoxic activity exerted 2 beta,8 alpha-di-angeloyloxy-10 beta-hydroxy-6 alpha H-guaian-3,(7-11)-dien-12,6-olide, a slovanolide derivative with an additional double bond in lactone ring, on highly invasive MCF 7/6 cell line, with IC50 value 0.7 mu M in both assays tested. Generally, guaianolides with a higher number of ester moieties at the positions 2 beta, 8 alpha, 10 beta or 11 alpha exhibited IC50 values in the micromolar range, while eudesmanolides and guaianolides with a lower number of esters did not induce significant cytotoxicity.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Phytochemistry", title = "Sesquiterpene lactones from the extracts of two Balkan endemic Laserpitium species and their cytotoxic activity", volume = "87", pages = "102-111", doi = "10.1016/j.phytochem.2012.11.011" }
Popović, V., Heyerick, A., Petrović, S., Van Calenbergh, S., Karalić, I., Niketić, M.,& Deforce, D.. (2013). Sesquiterpene lactones from the extracts of two Balkan endemic Laserpitium species and their cytotoxic activity. in Phytochemistry Pergamon-Elsevier Science Ltd, Oxford., 87, 102-111. https://doi.org/10.1016/j.phytochem.2012.11.011
Popović V, Heyerick A, Petrović S, Van Calenbergh S, Karalić I, Niketić M, Deforce D. Sesquiterpene lactones from the extracts of two Balkan endemic Laserpitium species and their cytotoxic activity. in Phytochemistry. 2013;87:102-111. doi:10.1016/j.phytochem.2012.11.011 .
Popović, Višnja, Heyerick, Arne, Petrović, Silvana, Van Calenbergh, Serge, Karalić, Izet, Niketić, Marjan, Deforce, Dieter, "Sesquiterpene lactones from the extracts of two Balkan endemic Laserpitium species and their cytotoxic activity" in Phytochemistry, 87 (2013):102-111, https://doi.org/10.1016/j.phytochem.2012.11.011 . .