Fatty Acids and Oxylipins as Antifungal and Anti-Mycotoxin Agents in Food: A Review

Abstract

Fungal contamination of food, especially by mycotoxigenic fungi, not only reduces the quality of the food, but can also cause serious diseases, thus posing a major food safety challenge to humans. Apart from sound food control systems, there is also a continual need to explore antifungal agents that can inhibit fungal growth and mycotoxin production in food. Many types of fatty acids (FAs) and their oxidized derivatives, oxylipins, have been found to exhibit such effects. In this review, we provide an update on the most recent literature on the occurrence and formation of FAs and oxylipins in food, their effects on fungal growth and mycotoxin synthesis, as well as the genetic and molecular mechanisms of actions. Research gaps in the field and needs for further studies in order to realizing the potential of FAs and oxylipins as natural antifungal preservatives in food are also discussed.

Chemical Composition, Antifungal and Anti-Biofilm Activities of Volatile Fractions of Convolvulus althaeoides L. Roots from Tunisia

“…In agreement with the photochemical results of the two VFs, the diversity and the richness of the two VFs in volatile compounds can explain their antifungal potential. Indeed, the main active compounds of the VFs of C. althaeoides L. roots were n -hexadecenoic acid [ 23 ], bis (2-ethylhexyl) adipate [ 24 ], benzyl alcohol [ 25 ] and linoleic acid [ 26 ] which are known as antifungal agents. In fact, it was reported previously that the n -hexadecanoic acid or palmitic acid, a saturated fatty acid, abundant compound in VF1 and VF2, showed antifungal activities against mycelial growth and spore production reaching 37.20% and 71.70% by 2 mM concentration [ 27 ], respectively.…”

“…Indeed, the high amounts of fatty acids and terpenoids were attributed to a better anti-biofilm activity [ 36 , 37 ]. n -Hexadecanoic acid (C 16 H 32 O 2 ), namely, palmitic acid, a saturated long-chain fatty acid with a 16-carbon backbone [ 23 ]; cuminaldehyde (C 10 H 12 O), a benzaldehyde substituted by an isopropyl group at position 4 [ 38 ]; linoleic acid (C 18 H 32 O 2 ), an octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry [ 39 ]; and benzyl alcohol (C 7 H 8 O), an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent [ 25 ] were the main compounds present in these fractions that were associated with anti-biofilm activities. The synergistic effects of such compounds might be responsible for the observed anti-biofilm activity [ 40 ].…”

Aspergillus flavus YRB2 from Thymelaea hirsuta (L.) Endl., a non-aflatoxigenic endophyte with ability to overexpress defense-related genes against Fusarium root rot of maize

“…Among the identified secondary metabolites, three fatty acids, namely palmitic acid, α-linolenic acid, and stearic acid constituted 43.3% of the produced metabolites. Antifungal activity of these fatty acids has been reported in many researches [37,38]. Different modes of action have been discussed in this concern including disruption of the cell membrane permeability leading to electrolyte leakage and cell death, and inhibition of protein synthesis and fatty acids metabolism [39].…”

Role of Tocochromanols in Tolerance of Cereals to Biotic Stresses: Specific Focus on Pathogenic and Toxigenic Fungal Species

“…There has been growing evidence that oxylipins can modulate spore production, fungal development, reproduction and secondary metabolites biosynthesis [ 127 , 129 , 130 ]. Investigations focusing on the biosynthesis of aflatoxins and fumonisins have demonstrated the opposite effect of 13-lipoxygenase and 9-lipoxygenase oxidation products (recently reviewed in Qiu et al [ 131 ]). Whereas fatty acid hydroperoxides generated through the 9-lipoxygenase pathway were shown to mimic the fungal oxylipins called psi factors for precocious sexual inducers and promote the production of mycotoxins, products derived from the action of 13-lipoxygenase exhibited a significant inhibitor effect [ 132 , 133 ].…”