Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols
Plants of the genus <i>Pulicaria</i> are known for providing traditional medicines, spices, herbal teas, and insect deterrents. <i>Pulicaria inuloides</i> (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aeria...
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/2/480 |
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| author | Janusz Malarz Klaudia Michalska Agnieszka Galanty Anna Karolina Kiss Anna Stojakowska |
| author_facet | Janusz Malarz Klaudia Michalska Agnieszka Galanty Anna Karolina Kiss Anna Stojakowska |
| author_sort | Janusz Malarz |
| collection | DOAJ |
| description | Plants of the genus <i>Pulicaria</i> are known for providing traditional medicines, spices, herbal teas, and insect deterrents. <i>Pulicaria inuloides</i> (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aerial parts of <i>P. inuloides</i> were analyzed using the UHPLC-PAD-MS<sup>n</sup> technique and revealed the presence of six caffeoylquinic and eleven caffeoylhexaric conjugates together with hydroxykaempferol dimethyl ether and quercetagetin trimethyl ether. Moreover, constituents of chloroform extract from the whole <i>P. inuloides</i> plants were isolated and identified by spectroscopic methods. One new and four known caryophyllene derivatives, three thymol derivatives, and four polymethoxylated flavonols were found in the analyzed extract. The structure of the new compound was established by spectroscopic methods (HRESIMS, <sup>1</sup>H NMR, <sup>13</sup>C NMR, COSY, HSQC, HMBC, NOESY). The cytotoxicity of 6-Hydroxykaempferol 3,7-dimethyl ether and quercetagetin 3,7,3’-trimethyl ether (chrysosplenol C), which are major flavonols isolated from the plant, were tested on prostate epithelial cells (PNT2), prostate cancer cells (DU145 and PC3), human keratinocytes (HaCaT), and melanoma cells (HTB140 and A375). Both flavonols demonstrated moderate cytotoxic activity against PC3 cells (IC<sub>50</sub> = 59.5 µM and 46.6 µM, respectively). The remaining cell lines were less affected (IC<sub>50</sub> > 150 µM). |
| first_indexed | 2024-03-09T11:36:52Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:36:52Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4629f9223e884b30a2d01614dc6532262023-11-30T23:40:27ZengMDPI AGMolecules1420-30492023-01-0128248010.3390/molecules28020480Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated FlavonolsJanusz Malarz0Klaudia Michalska1Agnieszka Galanty2Anna Karolina Kiss3Anna Stojakowska4Maj Institute of Pharmacology, Polish Academy of Sciences, Smętna Street 12, 31-343 Kraków, PolandMaj Institute of Pharmacology, Polish Academy of Sciences, Smętna Street 12, 31-343 Kraków, PolandDepartment of Pharmacognosy, Jagiellonian University Medical College, Medyczna Street 9, 30-688 Kraków, PolandDepartment of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, PolandMaj Institute of Pharmacology, Polish Academy of Sciences, Smętna Street 12, 31-343 Kraków, PolandPlants of the genus <i>Pulicaria</i> are known for providing traditional medicines, spices, herbal teas, and insect deterrents. <i>Pulicaria inuloides</i> (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aerial parts of <i>P. inuloides</i> were analyzed using the UHPLC-PAD-MS<sup>n</sup> technique and revealed the presence of six caffeoylquinic and eleven caffeoylhexaric conjugates together with hydroxykaempferol dimethyl ether and quercetagetin trimethyl ether. Moreover, constituents of chloroform extract from the whole <i>P. inuloides</i> plants were isolated and identified by spectroscopic methods. One new and four known caryophyllene derivatives, three thymol derivatives, and four polymethoxylated flavonols were found in the analyzed extract. The structure of the new compound was established by spectroscopic methods (HRESIMS, <sup>1</sup>H NMR, <sup>13</sup>C NMR, COSY, HSQC, HMBC, NOESY). The cytotoxicity of 6-Hydroxykaempferol 3,7-dimethyl ether and quercetagetin 3,7,3’-trimethyl ether (chrysosplenol C), which are major flavonols isolated from the plant, were tested on prostate epithelial cells (PNT2), prostate cancer cells (DU145 and PC3), human keratinocytes (HaCaT), and melanoma cells (HTB140 and A375). Both flavonols demonstrated moderate cytotoxic activity against PC3 cells (IC<sub>50</sub> = 59.5 µM and 46.6 µM, respectively). The remaining cell lines were less affected (IC<sub>50</sub> > 150 µM).https://www.mdpi.com/1420-3049/28/2/480caffeic acid derivativescaffeoylhexaric acidscaryopyllene derivativescytotoxicitypolymethoxylated flavonolsthymol derivatives |
| spellingShingle | Janusz Malarz Klaudia Michalska Agnieszka Galanty Anna Karolina Kiss Anna Stojakowska Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols Molecules caffeic acid derivatives caffeoylhexaric acids caryopyllene derivatives cytotoxicity polymethoxylated flavonols thymol derivatives |
| title | Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols |
| title_full | Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols |
| title_fullStr | Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols |
| title_full_unstemmed | Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols |
| title_short | Constituents of <i>Pulicaria inuloides</i> and Cytotoxic Activities of Two Methoxylated Flavonols |
| title_sort | constituents of i pulicaria inuloides i and cytotoxic activities of two methoxylated flavonols |
| topic | caffeic acid derivatives caffeoylhexaric acids caryopyllene derivatives cytotoxicity polymethoxylated flavonols thymol derivatives |
| url | https://www.mdpi.com/1420-3049/28/2/480 |
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