Phenolic Lipids Affect the Activity and Conformation of Acetylcholinesterase from Electrophorus electricus (Electric eel)

Abstract

Phenolic lipids were isolated from rye grains, cashew nutshell liquid (CNSL) from Anacardium occidentale, and fruit bodies of Merrulius tremellosus, and their effects on the electric eel acetylcholinesterase activity and conformation were studied. The observed effect distinctly depended on the chemical structure of the phenolic lipids that were available for interaction with the enzyme. All of the tested compounds reduced the activity of acetylcholinesterase. The degree of inhibition varied, showing a correlation with changes in the conformation of the enzyme tested by the intrinsic fluorescence of the Trp residues of the protein.

Cashew Nut Shell Liquid (CNSL) as a Source of Drugs for Alzheimer’s Disease

“…From the data collected in Table 6, it seems that the same applies to CNSL phenolic lipids-purified or as mixtures-, as well as their derivatives. For instance, in vitro and in vivo studies have shown that anacardic acid (14) may serve as a valuable anti-AD privileged scaffold thanks to its antioxidant and anti-inflammatory properties [76,92,93]. Beneficial anti-AD multi-target profiles have been reported for cardanol-derived cholinesterase inhibitors with antioxidant and anti-amyloid properties (49)(50)(51)(52)(53)(54)(55)(56)(57)(58) [89], CNSL-derived HDAC inhibitors 59-62 [91], and CNSL-derived compounds-tacrine hybrids (63)(64)(65)(66)(67)(68)(69)(70)(71)(72)(73)(74)(75) [94].…”

“…In contrast, 2-methylcardol (17c) and cardanol (15a) did not show any inhibitory effect [75]. Further, Stasiuk et al [76] tested the effects of the same phenolic lipids on AChE from Electrophorus electricus (Ee) and confirmed that those from A. occidentale (14a, 15a, 16c and 17c) were the most active, inhibiting the enzyme activity at micromolar level. The resorcinolic lipids from rye bran (16a, 18 and 19) showed moderate AChE inhibition, which increased with the number of carbon atoms of the alkyl chain.…”

“…We combined in a single chemical entity tacrine moieties (76-78, Figure 10) with a modified CNSL framework (79)(80)(81)(82). Considering that the presence of the long alkyl chain (C15) of 14a might limit drug-likeness due to excessive lipophilicity, we turned our attention to the shorter-chain (C8) CNSL derivatives (76)(77)(78)(79). In this way, we aimed to create new CNSL-tacrine hybrids which in principle maintained the tacrines' anticholinesterase activity, combined with the antiinflammatory activity of CNSL compounds, and possessed drug-like properties.…”

Inhibitory Effects of Sodium Arsenite and Acacia Honey on Acetylcholinesterase in Rats

“…It is also possible that the potentiation of sodium arsenite inhibitory activity was due to the identified phenolic compounds such as p-hydroxybenzoic acid, cinnamic acid, and chrysin present in the Acacia honey which could also inhibit the AChE. Indeed, phenolics such as anacardic acids, cardols, cardanols, and methylcardols have been reported to inhibit AChE [ 29 ]. Overall, the foregoing observations suggest that sodium arsenite and/or Acacia honey could be beneficial in the management of Alzheimer's disease in this regard.…”

The nutritional and bio‐active constituents, functional activities, and industrial applications of cashew (Anacardium occidentale): A review

“…For instance, Silva's research TA B L E 3 New compounds of cashew nuts (Suo et al, 2012). methylcardol were 4 ± 0.24, 3 ± 0.24, 3.5 ± 0.2, and 5 ± 0.41 μM, respectively (Stasiuk et al, 2014).…”