Structure-function relationships of antifungal monohydroxy unsaturated fatty acids (HUFA) of plant and bacterial origin.

This study investigated the relationships between the structures of hydroxy unsaturated fatty acids (HUFA) and their antifungal activities. Structurally diverse HUFA, including four monohydroxy-18:1 isomers, two monohydroxy 18:2 isomers and two monohydroxy 18:2 isomers were extracted from seeds of plants (Coriaria nepalensis, Thymus vulgaris, Mallotus philippensis and Dimorphotheca sinuata) for which information was available on PlantFAdb database, and from culture supernatants of lactobacilli. They were purified by high-speed counter current chromatography (HSCCC) and identified by LC-MS/MS. The minimum inhibitory concentrations of HUFA were tested against a panel of five yeasts and five mycelial fungi. The membrane phase changes under HUFA treatment and the content of ergosterol were both measured to differentiate HUFA-sensitive and HUFA-resistant fungi. HUFA with a hydroxyl group near the center of the 18-carbon fatty acid chains were found to contribute strongly to HUFA antifungal activity. Antifungal HUFA targeted filamentous fungi but not yeasts. HUFA didn't alter the overall membrane fluidity of sensitive fungi, but the most HUFA-sensitive fungi had a lower average ergosterol content compared to the resistant yeasts. This indicates the possible interaction of HUFA with fungal membrane with low sterol content, which partially support the previous proposed mode of action. Findings here provide insight on further development of HUFA application in food products.