Hydrolases-mediated transformation of oleuropein into demethyloleuropein

[Display omitted] •Demethyloleuropein was synthesized from oleuropein via the screening of a panel of hydrolases (EC 3).•α-chymotrypsin was the best biocatalyst, thus revealing a classical example of enzyme promiscuity.•The enzymatic reaction proceeded with complete chemoselectivity at pH 7 and 4 °C...

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Published in:Bioorganic chemistry 2019-03, Vol.84, p.384-388
Main Authors: Cariati, Luca, Oliverio, Manuela, Mutti, Francesco G., Bonacci, Sonia, Knaus, Tanja, Costanzo, Paola, Procopio, Antonio
Format: Article
Language:English
Subjects:
Animals
Biocatalysis
Cattle
Chymotrypsin - metabolism
Demethyloleuropein
Enzyme promiscuity
Hydrolases
Hydrolases - metabolism
Hydrolysis
Iridoid Glucosides - chemistry
Iridoid Glucosides - metabolism
Iridoids - chemistry
Iridoids - metabolism
Olea - chemistry
Olea - metabolism
Oleuropein
Pancreas - enzymology
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Summary:[Display omitted] •Demethyloleuropein was synthesized from oleuropein via the screening of a panel of hydrolases (EC 3).•α-chymotrypsin was the best biocatalyst, thus revealing a classical example of enzyme promiscuity.•The enzymatic reaction proceeded with complete chemoselectivity at pH 7 and 4 °C. Phenolic compounds present in extra virgin olive oil have recently attracted considerable attention due to their pharmacological activities. Among them oleacein (3,4-DHPEA-EDA), structurally related to oleochantal (4-HPEA-EDA), is one of the most studied. 3,4-DHPEA-EDA has been synthesized through decarboxylation of demethyloleuropein catalyzed by Er(OTf)3. Demethyloleuropein is extracted from black olives drupes in very limited amounts and only in particular periods of the year. The availability of demethyloleuropein could be increased by a selective hydrolysis of the methyl ester moiety of oleuropein, a secoiridoid present in large amount in olive leaves. In this work we describe a new enzymatic method for carrying out a selective hydrolysis of oleuropein via the screening of a panel of hydrolases (lipases, esterases and proteases). Among all the enzymes tested the best results was obtained using α-chymotrypsyn from bovine pancreas as biocatalyst, thus revealing a classic example of catalytic enzyme promiscuity.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2018.12.005