Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa
Acetylcholinesterase inhibitors remain the mainstay of symptomatic treatment for Alzheimer’s disease. The natural world is rich in acetylcholinesterase inhibitory molecules, and research efforts to identify novel leads is ongoing. Cladonia portentosa, commonly known as reindeer lichen, is an abundan...
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ftmdpi:oai:mdpi.com:/1420-3049/28/10/4145/ 2023-08-20T04:09:27+02:00 Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa Shipra Nagar Maria Pigott Wirginia Kukula-Koch Helen Sheridan agris 2023-05-17 application/pdf https://doi.org/10.3390/molecules28104145 EN eng Multidisciplinary Digital Publishing Institute Natural Products Chemistry https://dx.doi.org/10.3390/molecules28104145 https://creativecommons.org/licenses/by/4.0/ Molecules; Volume 28; Issue 10; Pages: 4145 usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism placodiolic acid pseudoplacodiolic acid Text 2023 ftmdpi https://doi.org/10.3390/molecules28104145 2023-08-01T10:06:31Z Acetylcholinesterase inhibitors remain the mainstay of symptomatic treatment for Alzheimer’s disease. The natural world is rich in acetylcholinesterase inhibitory molecules, and research efforts to identify novel leads is ongoing. Cladonia portentosa, commonly known as reindeer lichen, is an abundant lichen species found in Irish Boglands. The methanol extract of Irish C. portentosa was identified as an acetylcholinesterase inhibitory lead using qualitative TLC-bioautography in a screening program. To identify the active components, the extract was deconvoluted using a successive extraction process with hexane, ethyl acetate and methanol to isolate the active fraction. The hexane extract demonstrated the highest inhibitory activity and was selected for further phytochemical investigations. Olivetolic acid, 4-O-methylolivetolcarboxylic acid, perlatolic acid and usnic acid were isolated and characterized using ESI-MS and two-dimensional NMR techniques. LC-MS analysis also determined the presence of the additional usnic acid derivatives, placodiolic and pseudoplacodiolic acids. Assays of the isolated components confirmed that the observed anticholinesterase activity of C. portentosa can be attributed to usnic acid (25% inhibition at 125 µM) and perlatolic acid (20% inhibition at 250 µM), which were both reported inhibitors. This is the first report of isolation of olivetolic and 4-O-methylolivetolcarboxylic acids and the identification of placodiolic and pseudoplacodiolic acids from C. portentosa. Text Reindeer lichen MDPI Open Access Publishing Molecules 28 10 4145 |
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language |
English |
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usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism placodiolic acid pseudoplacodiolic acid |
spellingShingle |
usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism placodiolic acid pseudoplacodiolic acid Shipra Nagar Maria Pigott Wirginia Kukula-Koch Helen Sheridan Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa |
topic_facet |
usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism placodiolic acid pseudoplacodiolic acid |
description |
Acetylcholinesterase inhibitors remain the mainstay of symptomatic treatment for Alzheimer’s disease. The natural world is rich in acetylcholinesterase inhibitory molecules, and research efforts to identify novel leads is ongoing. Cladonia portentosa, commonly known as reindeer lichen, is an abundant lichen species found in Irish Boglands. The methanol extract of Irish C. portentosa was identified as an acetylcholinesterase inhibitory lead using qualitative TLC-bioautography in a screening program. To identify the active components, the extract was deconvoluted using a successive extraction process with hexane, ethyl acetate and methanol to isolate the active fraction. The hexane extract demonstrated the highest inhibitory activity and was selected for further phytochemical investigations. Olivetolic acid, 4-O-methylolivetolcarboxylic acid, perlatolic acid and usnic acid were isolated and characterized using ESI-MS and two-dimensional NMR techniques. LC-MS analysis also determined the presence of the additional usnic acid derivatives, placodiolic and pseudoplacodiolic acids. Assays of the isolated components confirmed that the observed anticholinesterase activity of C. portentosa can be attributed to usnic acid (25% inhibition at 125 µM) and perlatolic acid (20% inhibition at 250 µM), which were both reported inhibitors. This is the first report of isolation of olivetolic and 4-O-methylolivetolcarboxylic acids and the identification of placodiolic and pseudoplacodiolic acids from C. portentosa. |
format |
Text |
author |
Shipra Nagar Maria Pigott Wirginia Kukula-Koch Helen Sheridan |
author_facet |
Shipra Nagar Maria Pigott Wirginia Kukula-Koch Helen Sheridan |
author_sort |
Shipra Nagar |
title |
Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa |
title_short |
Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa |
title_full |
Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa |
title_fullStr |
Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa |
title_full_unstemmed |
Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa |
title_sort |
unravelling novel phytochemicals and anticholinesterase activity in irish cladonia portentosa |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2023 |
url |
https://doi.org/10.3390/molecules28104145 |
op_coverage |
agris |
genre |
Reindeer lichen |
genre_facet |
Reindeer lichen |
op_source |
Molecules; Volume 28; Issue 10; Pages: 4145 |
op_relation |
Natural Products Chemistry https://dx.doi.org/10.3390/molecules28104145 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/molecules28104145 |
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Molecules |
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28 |
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10 |
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4145 |
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1774722400831668224 |