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 abunda...
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ftdoajarticles:oai:doaj.org/article:813c3f28131048dfa489eaecd1739fac 2023-06-11T04:16:17+02:00 Unravelling Novel Phytochemicals and Anticholinesterase Activity in Irish Cladonia portentosa Shipra Nagar Maria Pigott Wirginia Kukula-Koch Helen Sheridan 2023-05-01T00:00:00Z https://doi.org/10.3390/molecules28104145 https://doaj.org/article/813c3f28131048dfa489eaecd1739fac EN eng MDPI AG https://www.mdpi.com/1420-3049/28/10/4145 https://doaj.org/toc/1420-3049 doi:10.3390/molecules28104145 1420-3049 https://doaj.org/article/813c3f28131048dfa489eaecd1739fac Molecules, Vol 28, Iss 4145, p 4145 (2023) usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism Organic chemistry QD241-441 article 2023 ftdoajarticles https://doi.org/10.3390/molecules28104145 2023-05-28T00:33:29Z 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 . Article in Journal/Newspaper Reindeer lichen Directory of Open Access Journals: DOAJ Articles Molecules 28 10 4145 |
institution |
Open Polar |
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Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism Organic chemistry QD241-441 |
spellingShingle |
usnic acid olivetolic acid 4- O -methylolivetolcarboxylic acid perlatolic acid LC-MS fragmentation mechanism Organic chemistry QD241-441 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 Organic chemistry QD241-441 |
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 |
Article in Journal/Newspaper |
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 |
MDPI AG |
publishDate |
2023 |
url |
https://doi.org/10.3390/molecules28104145 https://doaj.org/article/813c3f28131048dfa489eaecd1739fac |
genre |
Reindeer lichen |
genre_facet |
Reindeer lichen |
op_source |
Molecules, Vol 28, Iss 4145, p 4145 (2023) |
op_relation |
https://www.mdpi.com/1420-3049/28/10/4145 https://doaj.org/toc/1420-3049 doi:10.3390/molecules28104145 1420-3049 https://doaj.org/article/813c3f28131048dfa489eaecd1739fac |
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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