Institut für Lebensmittelchemie

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    The furan fatty acids 11M5 and 11D5 can act as activators of human peroxisome proliferator‐activated receptor gamma
    (2025) Pospiech, Jonas; Caspi, Ayelet; Vetter, Walter; Kerem, Zohar; Frank, Jan; Kufer, Thomas A.; Pospiech, Jonas; Institute of Nutritional Medicine, University of Hohenheim, Stuttgart, Germany; Caspi, Ayelet; Robert H. Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, Rehovot, Israel; Vetter, Walter; Institute of Food Chemistry (170b), University of Hohenheim, Stuttgart, Germany; Kerem, Zohar; Robert H. Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, Rehovot, Israel; Frank, Jan; Department of Food Biofunctionality, Institute of Nutritional Sciences, University of Hohenheim, Stuttgart, Germany; Kufer, Thomas A.; Institute of Nutritional Medicine, University of Hohenheim, Stuttgart, Germany
    Furan fatty acids (FuFA) are a minor class of fatty acids in food that are characterized by a furan ring within the alkyl chain. Furan fatty acids have strong antioxidant properties but their biological functions remain largely elusive. Using molecular docking combined with biomolecular validation, we investigated the regulatory activities of the key furan fatty acids 9M5, 11M5, and 11D5 on human nuclear receptors, including PPARγ, LXR, PXR, FXR, and HNF4α. Using computational methods, 11M5 and 11D5 and to a lesser extend 9M5 were predicted to bind to PPARγ. The activation of both PPARγ1 and PPARγ2 was confirmed in human HEK293T cells and structure‐activity experiments revealed that this was dependent on the furan fatty acid backbone. In summary, our data provide novel insights into the biological activities of furan fatty acids in human cells and indicate that activation of peroxisome proliferator‐activated receptor gamma underlies their beneficial health effects. These findings establish a clear mechanistic basis, supported by the inactivity of related compounds, and we are confident that future expanded studies will further confirm this mechanism.
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    LC‐Orbitrap‐HRMS determination of two novel plastochromanol homologues
    (2023) Hammerschick, Tim; Graf, Jana; Vetter, Walter
    Scope: The antioxidant plastochromanol-8 (PC-8) is a tocochromanol which differs from γ-tocotrienol in having an unsaturated side chain of eight instead of three isoprene units. The recent isolation of PC-8 from flaxseed oil indicates the additional presence of lower shares of two previously unknown homologues, plastochromanol-7 (PC-7) and plastochromanol-9 (PC-9), which feature seven and nine isoprenoid units respectively on the γ-chromanol backbone. Here, a fast LC-Orbitrap-HRMS method is applied for the determination of PC-7 and PC-9 in seven plant oils and a plant extract. Methods and results: The presence of PC-7, PC-8, and PC-9 is confirmed in all eight investigated samples by LC-Orbitrap-HRMS analysis after saponification. PC-8 amounts of ≈315–350 mg kg−1 in two flaxseed oils, ≈75 mg kg−1 in rapeseed oil, ≈38 mg kg−1 in camelina oil, ≈80–120 mg kg−1 in two mustard oils, ≈90 mg kg−1 in candle nut oil, and ≈900 mg kg−1 dry weight in Cecropia leaves are determined by quantification. Semi-quantification of PC-7 and PC-9 indicated the presence of ≈0.1–1% of PC-7 and PC-9 in varied relative ratios. Conclusion: The novel plastochromanol homologues are of particular interest to researchers with focus on vitamin E and other tocochromanols because of their unexplored bioactivity.