Microbial production of 4-hydroxybenzylidene acetone, the direct precursor of raspberry ketone

• Published in: Letters in applied microbiology Vol. 45; no. 1; pp. 29 - 35
• Main Authors: Feron, G, Mauvais, G, Martin, F, Sémon, E, Blin-Perrin, C
• Format: Journal Article
• Language: English
• Published: Oxford, UK Oxford, UK : Blackwell Publishing Ltd 01.07.2007; Blackwell Publishing Ltd; Blackwell Science
• Subjects: 4-hydroxybenzylidene acetone; aldolase; Bacillus (bacteria); Bacillus cereus - enzymology; Bacillus cereus - growth & development; Bacillus cereus - metabolism; Bacillus sp; Bacillus subtilis - enzymology; Bacillus subtilis - growth & development; Bacillus subtilis - metabolism; Biological and medical sciences; Butanones - chemistry; Butanones - metabolism; Culture Media; Escherichia coli; Escherichia coli - enzymology; Escherichia coli - growth & development; Escherichia coli - metabolism; fructose-bisphosphate aldolase; Fructose-Bisphosphate Aldolase - metabolism; Fundamental and applied biological sciences. Psychology; Fungi - growth & development; Fungi - metabolism; Industrial Microbiology - methods; Microbiology; raspberry ketone; Ribosemonophosphates - metabolism; Enzyme; Applied microbiology; raspberry ketone; Escherichia coli; 4-hydroxybenzylidene acétone; Lyases; Aldehyde-lyases; Bacillaceae; Ketone; Precursor; Carbon-carbon lyases; Bacillales; Bacillus sp; Bacillus; Production; Fructose-bisphosphate aldolase; Bacteria; Microorganism; aldolase; Enterobacteriaceae; Acetone
• ISSN: 0266-8254; 1472-765X
• DOI: 10.1111/j.1472-765X.2007.02147.x

To investigate the enzymatic aldol reaction between acetone as a donor and 4-hydroxybenzaldehyde as a receptor to generate 4-(4-hydroxyphenyl)-but-3-ene-2-one or 4-hydroxybenzylidene acetone, the direct precursor of 4-(4-hydroxyphenyl)-butan-2-one or raspberry ketone, using different species of filamentous fungi and bacteria. Different classes of micro-organisms were tested in a medium containing mainly acetone and 4-hydoxybenzaldehyde. Of the micro-organisms tested, only bacteria were able to synthesize significant amounts of 4-hydroxybenzylidene acetone, ranging from 15 to 160 mg l⁻¹ after 21 h of bioconversion, as a function of the bacteria tested. The biological production of 4-hydroxybenzylidene acetone has been described with bacteria possessing 2-deoxyribose-5-phosphate aldolase (DERA, EC 4·1·2·4). This result suggests that DERA is involved in the catalytic aldolization of precursors for the production of 4-hydroxybenzylidene acetone. Raspberry ketone or frambinone represents a total market value of between [Euro Sign]6 million and [Euro Sign]10 million. The possibility of producing its direct precursor through a simple process using bacteria is of considerable interest to the flavour market and the food industry as a whole. This paper broadens the spectrum for the use of aldolase to achieve the biological synthesis of compounds of interest.