Acylphloroglucinols with acetylcholinesterase inhibitory effects from the fruits of Eucalyptus robusta.
Bioorg Chem
; 103: 104127, 2020 10.
Article
en En
| MEDLINE
| ID: mdl-32745755
ABSTRACT
Eleven new acylphloroglucinols, including six new formylated phloroglucinol-monoterpene meroterpenoids, eucalyprobusals A-F (1-6), one monomeric acylphloroglucinol, eucalyprobusone B (7), and four dimeric acylphloroglucinols, eucalyprobusones C-F (8-11) were purified from the fruits of Eucalyptus robusta. The establishment of the structures of 1-11 was achieved by a combination of NMR and HRESIMS data analyses, electron circular dichroism (ECD), and single-crystal X-ray diffraction. Compounds 6, 8, and an inseparable mixture of 10 and 11 were found to be potent AChE inhibitors with IC50 values of 3.22 ± 0.36, 3.82 ± 0.22, and 2.55 ± 0.28 µΜ, respectively. Possible interaction sites of 6, 8, 10, and 11 with AChE were investigated by means of molecular docking studies, and the results revealed that AChE residues Asn87, Ser125, Thr83, Tyr133, Tyr124, Tyr337, and Tyr341 played crucial roles in the observed activity of the aforementioned compounds.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Floroglucinol
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Acetilcolinesterasa
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Inhibidores de la Colinesterasa
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Eucalyptus
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Frutas
Límite:
Humans
Idioma:
En
Año:
2020
Tipo del documento:
Article