Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation
In an in vitro screening for human carbonic anhydrase (hCA) inhibiting agents from higher plants, the petroleum ether and ethyl acetate extracts of Magydaris pastinacea seeds selectively inhibited hCA IX and hCA XII isoforms. The phytochemical investigation of the extracts led to the isolation of te...
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2020-01-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | http://dx.doi.org/10.1080/14756366.2020.1713114 |
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doaj-ba38eeee14924a808934f20776c11ded2021-07-15T13:10:32ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742020-01-0135153954810.1080/14756366.2020.17131141713114Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluationBenedetta Fois0Simona Distinto1Rita Meleddu2Serenella Deplano3Elias Maccioni4Costantino Floris5Antonella Rosa6Mariella Nieddu7Pierluigi Caboni8Claudia Sissi9Andrea Angeli10Claudiu T. Supuran11Filippo Cottiglia12Department of Life and Environmental Sciences, University of CagliariDepartment of Life and Environmental Sciences, University of CagliariDepartment of Life and Environmental Sciences, University of CagliariDepartment of Life and Environmental Sciences, University of CagliariDepartment of Life and Environmental Sciences, University of CagliariDepartment of Chemical and Geological Sciences, University of CagliariDepartment of Biomedical Sciences, University of Cagliari, Cittadella Universitaria di MonserratoDepartment of Biomedical Sciences, University of Cagliari, Cittadella Universitaria di MonserratoDepartment of Life and Environmental Sciences, University of CagliariDepartment of Pharmaceutical and Pharmacological Sciences, University of PadovaNEUROFARBA Department, Sezione di Scienze Farmaceutiche e Nutraceutiche, Università degli Studi di FirenzeNEUROFARBA Department, Sezione di Scienze Farmaceutiche e Nutraceutiche, Università degli Studi di FirenzeDepartment of Life and Environmental Sciences, University of CagliariIn an in vitro screening for human carbonic anhydrase (hCA) inhibiting agents from higher plants, the petroleum ether and ethyl acetate extracts of Magydaris pastinacea seeds selectively inhibited hCA IX and hCA XII isoforms. The phytochemical investigation of the extracts led to the isolation of ten linear furocoumarins (1–10), four simple coumarins (12–15) and a new angular dihydrofurocoumarin (11). The structures of the isolated compounds were elucidated based on 1 D and 2 D NMR, MS, and ECD data analysis. All isolated compounds were inactive towards the ubiquitous cytosolic isoform hCA I and II (Ki > 10,000 nM) while they were significantly active against the tumour-associated isoforms hCA IX and XII. Umbelliprenin was the most potent coumarin inhibiting hCA XII isoform with a Ki of 5.7 nM. The cytotoxicity of the most interesting compounds on HeLa cancer cells was also investigated.http://dx.doi.org/10.1080/14756366.2020.1713114carbonic anhydrasecoumarininhibitornatural productmagydaris pastinacea |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Benedetta Fois Simona Distinto Rita Meleddu Serenella Deplano Elias Maccioni Costantino Floris Antonella Rosa Mariella Nieddu Pierluigi Caboni Claudia Sissi Andrea Angeli Claudiu T. Supuran Filippo Cottiglia |
| spellingShingle |
Benedetta Fois Simona Distinto Rita Meleddu Serenella Deplano Elias Maccioni Costantino Floris Antonella Rosa Mariella Nieddu Pierluigi Caboni Claudia Sissi Andrea Angeli Claudiu T. Supuran Filippo Cottiglia Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation Journal of Enzyme Inhibition and Medicinal Chemistry carbonic anhydrase coumarin inhibitor natural product magydaris pastinacea |
| author_facet |
Benedetta Fois Simona Distinto Rita Meleddu Serenella Deplano Elias Maccioni Costantino Floris Antonella Rosa Mariella Nieddu Pierluigi Caboni Claudia Sissi Andrea Angeli Claudiu T. Supuran Filippo Cottiglia |
| author_sort |
Benedetta Fois |
| title |
Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation |
| title_short |
Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation |
| title_full |
Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation |
| title_fullStr |
Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation |
| title_full_unstemmed |
Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation |
| title_sort |
coumarins from magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases ix and xii: isolation, biological studies and in silico evaluation |
| publisher |
Taylor & Francis Group |
| series |
Journal of Enzyme Inhibition and Medicinal Chemistry |
| issn |
1475-6366 1475-6374 |
| publishDate |
2020-01-01 |
| description |
In an in vitro screening for human carbonic anhydrase (hCA) inhibiting agents from higher plants, the petroleum ether and ethyl acetate extracts of Magydaris pastinacea seeds selectively inhibited hCA IX and hCA XII isoforms. The phytochemical investigation of the extracts led to the isolation of ten linear furocoumarins (1–10), four simple coumarins (12–15) and a new angular dihydrofurocoumarin (11). The structures of the isolated compounds were elucidated based on 1 D and 2 D NMR, MS, and ECD data analysis. All isolated compounds were inactive towards the ubiquitous cytosolic isoform hCA I and II (Ki > 10,000 nM) while they were significantly active against the tumour-associated isoforms hCA IX and XII. Umbelliprenin was the most potent coumarin inhibiting hCA XII isoform with a Ki of 5.7 nM. The cytotoxicity of the most interesting compounds on HeLa cancer cells was also investigated. |
| topic |
carbonic anhydrase coumarin inhibitor natural product magydaris pastinacea |
| url |
http://dx.doi.org/10.1080/14756366.2020.1713114 |
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