Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol...
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todo:paper_00320943_v76_n6_p607_Gurovic2023-10-03T14:45:06Z Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) Gurovic, M.S.V. Castro, M.J. Richmond, V. Faraoni, M.B. Maier, M.S. Murray, A.P. Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol (2), heliantriol B2 (3), lupeol (4), and a mixture of -and -amyrin (5a and 5b) as active constituents. Pseudotaraxasterol (6) and taraxasterol (7) were also isolated from this extract and showed no activity at the same analytical conditions. Compound 1 showed the highest AChE inhibitory activity with 31.2% of inhibition at 0.5mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1% of inhibition at 0.5mM (IC50=0. 1900.003mM). Compounds 1, 2, 3, 5, 6, and 7 are reported here for the first time in C. erinacea. This is the first report of AChE inhibition from calenduladiol (1) as well as from a sulfate derived from a natural product. © Georg Thieme Verlag KG Stuttgart - New York. Fil:Maier, M.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00320943_v76_n6_p607_Gurovic |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea |
| spellingShingle |
Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea Gurovic, M.S.V. Castro, M.J. Richmond, V. Faraoni, M.B. Maier, M.S. Murray, A.P. Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) |
| topic_facet |
Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea |
| description |
A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol (2), heliantriol B2 (3), lupeol (4), and a mixture of -and -amyrin (5a and 5b) as active constituents. Pseudotaraxasterol (6) and taraxasterol (7) were also isolated from this extract and showed no activity at the same analytical conditions. Compound 1 showed the highest AChE inhibitory activity with 31.2% of inhibition at 0.5mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1% of inhibition at 0.5mM (IC50=0. 1900.003mM). Compounds 1, 2, 3, 5, 6, and 7 are reported here for the first time in C. erinacea. This is the first report of AChE inhibition from calenduladiol (1) as well as from a sulfate derived from a natural product. © Georg Thieme Verlag KG Stuttgart - New York. |
| format |
JOUR |
| author |
Gurovic, M.S.V. Castro, M.J. Richmond, V. Faraoni, M.B. Maier, M.S. Murray, A.P. |
| author_facet |
Gurovic, M.S.V. Castro, M.J. Richmond, V. Faraoni, M.B. Maier, M.S. Murray, A.P. |
| author_sort |
Gurovic, M.S.V. |
| title |
Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) |
| title_short |
Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) |
| title_full |
Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) |
| title_fullStr |
Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) |
| title_full_unstemmed |
Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) |
| title_sort |
triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea d. don. subsp. erinacea (asteraceae) |
| url |
http://hdl.handle.net/20.500.12110/paper_00320943_v76_n6_p607_Gurovic |
| work_keys_str_mv |
AT gurovicmsv triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae AT castromj triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae AT richmondv triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae AT faraonimb triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae AT maierms triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae AT murrayap triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae |
| _version_ |
1782024926220255232 |