New AChE inhibitors from microbial transformation of trachyloban-19-oic acid by Syncephalastrum racemosum

[Display omitted] •Biotransformation of trachyloban-19-oic acid (1) by Syncephalastrum racemosum produced three products.•Two biotransformation products have never been reported so far.•All the products (2–4) presented AChE inhibitory activity higher than starting material 1.•Product 3 presented IC5...

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Bibliographic Details
Published in:Bioorganic chemistry 2018-09, Vol.79, p.60-63
Main Authors: dos Santos, Gabriel Franco, da Silva Lima, Gesiane, Pereira de Oliveira, Geane, de Souza Filho, José Dias, da Silva Amaral, Luciana, Rodrigues-Filho, Edson, Takahashi, Jacqueline Aparecida
Format: Article
Language:English
Subjects:
Acetylcholinesterase
Acetylcholinesterase - metabolism
Alzheimer’s disease
Animals
Biotransformation
Cholinesterase Inhibitors - chemistry
Diterpenes - chemistry
Diterpenes - metabolism
Electrophorus
Enzyme Assays
Fruit - chemistry
Molecular Structure
Mucorales - metabolism
Oxidation-Reduction
Syncephalastrum racemosum
Trachyloban-19-oic acid
Xylopia - chemistry
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Summary:[Display omitted] •Biotransformation of trachyloban-19-oic acid (1) by Syncephalastrum racemosum produced three products.•Two biotransformation products have never been reported so far.•All the products (2–4) presented AChE inhibitory activity higher than starting material 1.•Product 3 presented IC50 = 0.06 μM, which is about six times higher than activity found for the positive control. Trachyloban-19-oic acid (1) is a diterpene very abundant in nature and its structural modification can furnish new bioactive compounds. Biotransformation of 1 by fungus Syncephalastrum racemosum provided three derivatives, two hydroxylated products (2–3) and one product of rearrangement (4). Products 3 and 4 have never been reported so far, to the best of our knowledge. Structure of 3 was formed after oxidation and rearrangement of compound 2. Compounds 1–4 were evaluated for inhibition of acetylcholinesterase, enzyme linked to the symptomatic control of Alzheimer’s disease. All the compounds presented inhibitory activity higher than starting material 1, and product 3 presented IC50 = 0.06 μM, which is about six times higher than activity found for galanthamine (IC50 = 0.38 μM), the positive control used in this assay.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2018.04.011