Institut für Lebensmittelchemie

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Characterization of the major odor-active compounds in fresh rhizomes and leaves of Houttuynia cordata by comparative aroma extract dilution analysis
(2025) Xu, Zhenli; Liu, Jing; Kreissl, Johanna; Oellig, Claudia; Vetter, Walter; Steinhaus, Martin; Frank, Stephanie; Rodov, Victor
Houttuynia cordata is a culinary herb from Asia. Its edible rhizomes and leaves have a fishy aroma, the molecular background of which was unknown. A comparative aroma extract dilution analysis applied to fresh rhizomes and leaves resulted in 44 and 41 odorants, respectively, 38 of which were present with FD factors ≥1 in both samples. The odorant with the highest FD factors, whether in the rhizomes or leaves, was identified as metallic, soapy, fishy smelling 3-oxododecanal. Toward clarifying its tautomeric composition, quantum calculations suggested a predominance of the enol forms in the plant. However, the form perceived at the sniffing port during GC–O remained unclear.
Enzymatically formed fatty acid hydroperoxides determined through GC‐MS analysis of enantiomeric excess of hydroxy fatty acids after reduction and ibuprofen derivatization
(2025) Hotz, Lisa; Zartmann, Anne; Noack, Isabelle; Drees, Luca J.; Kuschow, Meret K.; Heinrich, Markus R.; Janssen, Hans‐Gerd; Hammann, Simon
Unsaturated fatty acids are susceptible to lipid oxidation through autoxidation, photooxygenation or enzymatical oxidation. A characteristic feature of enzyme‐catalyzed oxidation is the high regio‐ and stereospecificity of the formed fatty acid hydroperoxides. In this study, we present a method to quantify enzymatic lipid oxidation through reducing hydroperoxy fatty acid methyl esters to hydroxy fatty acid methyl esters and derivatizing them with enantiopure (S)‐ibuprofen, allowing the resolution of the enantiomer pairs as diastereomers via achiral GC‐MS. After application to enantiopure reference fatty acids, the approach was applied to autoxidation products of linoleic acid, and the expected racemic mixtures of the 9‐ and 13‐hydroperoxide derived hydroxy fatty acids were detected. On the other hand, when linoleic acid was oxidized using soybean lipoxygenase, clear enantiomeric excess of the (13S) enantiomer could be detected, proving the applicability of this method to detect enzymatic oxidation through enantiomeric excess.
GC/EI-MS method for the determination of phytosterols in vegetable oils
(2021) Schlag, Sarah; Huang, Yining; Vetter, Walter
Sterols are a highly complex group of lipophilic compounds present in the unsaponifiable matter of virtually all living organisms. In this study, we developed a novel gas chromatography with mass spectrometry selected ion monitoring (GC/MS-SIM) method for the comprehensive analysis of sterols after saponification and silylation. A new referencing system was introduced by means of a series of saturated fatty acid pyrrolidides (FAPs) as internal standards. Linked with retention time locking (RTL), the resulting FAP retention indices (RIFAP) of the sterols could be determined with high precision. The GC/MS-SIM method was based on the parallel measurement of 17 SIM ions in four time windows. This set included eight molecular ions and seven diagnostic fragment ions of silylated sterols as well as two abundant ions of FAPs. Altogether, twenty molecular ions of C27- to C31-sterols with 0–3 double bonds were included in the final method. Screening of four common vegetable oils (sunflower oil, hemp oil, rapeseed oil, and corn oil) enabled the detection of 30 different sterols and triterpenes most of which could be identified.
Monodopsis subterranea is a source of α‐tocomonoenol, and its concentration, in contrast to α‐tocopherol, is not affected by nitrogen depletion
(2024) Montoya‐Arroyo, Alexander; Muñoz‐González, Alejandra; Lehnert, Katja; Frick, Konstantin; Schmid‐Staiger, Ulrike; Vetter, Walter; Frank, Jan
α-Tomonoenols (αT1) are tocochromanols structurally related to tocopherols (T) and tocotrienols (T3), the bioactive members of the vitamin E family. However, limited evidence exists regarding the sources and biosynthesis of tocomonoenols. Nitrogen depletion increases the content of α-tocopherol (αT), the main vitamin E congener, in microalgae, but little is known regarding its effect on other tocochromanols, such as tocomonoenols and tocotrienols. We therefore quantified the concentrations of T, T1, and T3, in freeze-dried biomass from nitrogen-sufficient, and nitrogen-depleted Monodopsis subterranea (Eustigmatophyceae). The identities of isomers of αT1 were confirmed by LC–MS and GC–MS. αT was the predominant tocochromanol (82% of total tocochromanols). αT1 was present in higher quantities than the sum of all T3 (6% vs. 1% of total tocochromanols). 11′-αT1 was the main αT1 isomer. Nitrogen depletion increased αT, but not αT1 or T3 in M. subterranea. In conclusion, nitrogen depletion increased the content of αT, the biologically most active form of vitamin E, in M. subterranea without affecting αT1 and T3 and could potentially be used as a strategy to enhance its nutritional value but not to increase αT1 content, indicating that αT1 accumulation is independent of that of αT in microalgae.
The natural product 2,4,6-tribromoanisole is the predominant polyhalogenated compound in representative Australian passive air samples
(2025) Schweizer, Sina; Wang, Xianyu; Paxman, Chris; Mueller, Jochen F.; Vetter, Walter; Schweizer, Sina; Institute of Food Chemistry, Department of Food Chemistry (170B), University of Hohenheim, 70599, Stuttgart, Germany; Wang, Xianyu; University of Queensland, Queensland Alliance for Environmental Health Sciences, 4102, Brisbane, Australia; Paxman, Chris; University of Queensland, Queensland Alliance for Environmental Health Sciences, 4102, Brisbane, Australia; Mueller, Jochen F.; University of Queensland, Queensland Alliance for Environmental Health Sciences, 4102, Brisbane, Australia; Vetter, Walter; Institute of Food Chemistry, Department of Food Chemistry (170B), University of Hohenheim, 70599, Stuttgart, Germany
Passive air samplers are well-suited for monitoring persistent organic pollutants (POPs) in ambient air. While the presence of POPs had been documented in Australian air, no data existed on structurally similar, halogenated natural products (HNPs), although these were frequently found in marine biota samples from Australia at levels exceeding those of anthropogenic POPs. This study reports quantitative data of the HNP 2,4,6-tribromoanisole (2,4,6-TBA) along with three POPs (polychlorinated biphenyls (PCBs) 153 and 138 as well as hexachlorobenzene (HCB)) in six selected passive air samples from different Australian regions (islands, coastal cities, and inland). For the most abundant HNP, 2,4,6-TBA, time-averaged concentrations for one year were determined at up to 420 pg/m 3 (One Tree Island), indicating its predominant natural production in the Great Barrier Reef (GBR). High concentrations of 2,4,6-TBA (17 pg/m 3 ), even in the remote inland sample (~ 800 km from the sea), led to the conclusion that the marine-derived 2,4,6-TBA was transported over long distances in air and can be found ubiquitously in Australian air. Even in the coastal cities of Brisbane and Darwin, 2,4,6-TBA levels were comparable to those of the PCBs. The HNP 2,3,3',4,4',5,5'-heptachloro-1'-methyl-1,2'-bipyrrole (Q1) was also detected in air from two islands. Its presence in air from One Tree Island was in line with expectations, given the high levels in marine mammal samples from the GBR. In direct comparison, the ~15 times higher ratio of Q1/2,4,6-TBA in air from Phillip Island indicated Q1 could be even more abundant in this marine region than in the GBR.
Potentially beneficial effects on healthy aging by supplementation of the EPA-rich microalgae phaeodactylum tricornutum or its supernatant - a randomized controlled pilot trial in elderly individuals
(2022) Stiefvatter, Lena; Frick, Konstantin; Lehnert, Katja; Vetter, Walter; Montoya-Arroyo, Alexander; Frank, Jan; Schmid-Staiger, Ulrike; Bischoff, Stephan C.
Dietary supplements that promote healthy aging are mostly warranted in an aging society. Because of age-related risks, anti-inflammatory and anti-oxidative agents such as microalgae are potential candidates for intervention. In a randomized controlled trial, we tested Phaeodactylum tricornutum (PT), a microalgae rich in eicosapentaenoic acid (EPA), carotenoids, vitamins, and β-glucans, cultured in bioreactors. In this pilot trial, 19 healthy elderly received supplements for two weeks based on either the whole PT (A), the β-1,3-glucan-rich PT supernatant (SupB), the combination thereof (A+SupB), or a Comparator product (Comp). The primary outcome variable plasma interleukin-6 was reduced after treatment with A+SupB compared to the Comp group (p = 0.04). The mobility parameters 5 s sit-to-stand test (p = 0.04 in the A group) and by trend gait speed (p = 0.08 in the A+SupB diet) were improved compared to Comp. No treatment effects were observed for fatty acids, compared to Comp but omega-6 to -3 fatty acid ratio (p = 0.006) and arachidonic acid/EPA ratio (p = 0.006) were reduced within group A+SupB. Further, the SupB study product reduced faecal zonulin (p = 0.03) compared to the Comp. The data revealed an anti-inflammatory and potentially anti-oxidative effect of particular PT preparations, suggesting that they might be suitable for effects in healthy elderly.
Stable isotope analysis confirms substantial changes in the fatty acid composition of bacteria treated with antimicrobial random peptide mixtures (RPMs)
(2022) Wiedmaier-Czerny, Nina; Schroth, Dorothee; Krauß, Stephanie; Topman-Rakover, Shiri; Brill, Aya; Burdman, Saul; Hayouka, Zvi; Vetter, Walter
Resistance of plant-pathogenic bacteria to classic antibiotics has prompted the search for suitable alternative antimicrobial substances. One promising strategy could be the use of purposely synthesized random peptide mixtures (RPMs). Six plant-pathogenic bacteria were cultivated and treated with two RPMs previously found to show antimicrobial activity mainly by bacterial membrane disruption. Here, we show that bacteria treated with RPMs showed partly remarkable changes in the fatty acid pattern while those unaffected did not. Quantitative changes could be verified by compound specific isotope analysis of δ 13 C values (‰). This technique was employed due to the characteristic feature of stronger bonds between heavier isotopes in (bio)chemical reactions. As a proof of concept, the increase in abundance of a fatty acid group after RPM treatment was accompanied with a decrease in the 13 C content and vice versa. We propose that our findings will help designing and synthesizing more selective antimicrobial peptides.

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