Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2014 May 29:4:46.
doi: 10.1186/s13568-014-0046-7. eCollection 2014.

The chemical nature of phenolic compounds determines their toxicity and induces distinct physiological responses in Saccharomyces cerevisiae in lignocellulose hydrolysates

Peter Temitope Adeboye  1 , Maurizio Bettiga  1 , Lisbeth Olsson  1
Affiliations

The chemical nature of phenolic compounds determines their toxicity and induces distinct physiological responses in Saccharomyces cerevisiae in lignocellulose hydrolysates

Peter Temitope Adeboye et al. AMB Express. .

Abstract

We investigated the severity of the inhibitory effects of 13 phenolic compounds usually found in spruce hydrolysates (4-hydroxy-3-methoxycinnamaldehyde, homovanilyl alcohol, vanillin, syringic acid, vanillic acid, gallic acid, dihydroferulic acid, p-coumaric acid, hydroquinone, ferulic acid, homovanillic acid, 4-hydroxybenzoic acid and vanillylidenacetone). The effects of the selected compounds on cell growth, biomass yield and ethanol yield were studied and the toxic concentration threshold was defined for each compound. Using Ethanol Red, the popular industrial strain of Saccharomyces cerevisiae, we found the most toxic compound to be 4-hydroxy-3-methoxycinnamaldehyde which inhibited growth at a concentration of 1.8 mM. We also observed that toxicity did not generally follow a trend based on the aldehyde, acid, ketone or alcohol classification of phenolic compounds, but rather that other structural properties such as additional functional groups attached to the compound may determine its toxicity. Three distinctive growth patterns that effectively clustered all the compounds involved in the screening into three categories. We suggest that the compounds have different cellular targets, and that. We suggest that the compounds have different cellular targets and inhibitory mechanisms in the cells, also compounds who share similar pattern on cell growth may have similar inhibitory effect and mechanisms of inhibition.

Keywords: Conversion; Inhibition; Phenolics; Saccharomyces cerevisiae; Tolerance; Toxicity.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Three distinct growth profiles ofSaccharomyces cerevisiaein the presence of phenolic compounds with: a. vanillin; c.p-Coumaric acid; d. Vanillylidenacetone representing common growth profiles within the three cluster groups. Elongation in lag phase was only shown in figure b for the first cluster since there was no lag phase elongation in the second and third clusters of compounds.
Figure 2
Figure 2
Bar chart showing concentrations at which different phenolic compounds within each growth-based cluster became too toxic for the growth of Saccharomyces cerevisiae .
Figure 3
Figure 3
Metabolite profiles representatives of Saccharomyces cerevisiae cultivations in the presence of: a. YMMM; b. syringic acid; c. dihydroferulic acid; d. homovanillic acid; e. 4-hydroxybenzoic acid; f. vanillylidenacetone and g. gallic acid.
Figure 4
Figure 4
Intra-cluster comparison of the effects of phenolic compounds on: a. ethanol yield; b. acetate yield; c. biomass yield; and d. glycerol yield from glucose. Syringic and dihydroferulic acids were selected from cluster 1, homovanillic and 4-hydroxybenzoic acid from cluster 2, vanillylidenacetone and gallic acid from cluster 3.
Figure 5
Figure 5
Structures of coniferyl aldehyde, ferulic acid and vanillin.
See this image and copyright information in PMC

References

    1. Ando S, Arai I, Kiyoto K, Hanai S. Identification of Aromatic Monomers in Steam-Exploded Poplar and Their Influences on Ethanol Fermentation by Saccharomyces cerevisiae. Journal of Fermentation Technology. 1986;4(6):567–570. doi: 10.1016/0385-6380(86)90084-1. - DOI
    1. Almeida J, Modig T, Petersson A, Hähn-Hägerdal B, Liden G, Gorwa-Grauslund M. Increased tolerance and conversion of inhibitors in lignocellulosic hydrolysates by Saccharomyces cerevisiae. J Chem Technol Biotechnol. 2007;4:340–349. doi: 10.1002/jctb.1676. - DOI
    1. Balasundram N, Sundram K, Samman S. Phenolic compounds in plants and agri-industrial by-products: antioxidant activity, occurrence, and potential uses. Food Chem. 2006;4:191–203. doi: 10.1016/j.foodchem.2005.07.042. - DOI
    1. Benavente-Garcia O, Castillo J, Marin FR, Ortuno A, Del Rio JA. Uses and properties of citrus flavonoids. J Agric Food Chem. 1997;4:4505–4515. doi: 10.1021/jf970373s. - DOI
    1. Bhattacharya A, Sood P, Citovsky V. The roles of plant phenolics in defence and communication during Agrobacterium and Rhizobium infection. Mol Plant Pathol. 2010;4:705–719. - PMC - PubMed