Institut für Lebensmittelchemie

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Antifungal properties of bioactive compounds isolated from Fucus vesiculosus supercritical carbon dioxide extract
(2024) Tyśkiewicz, Katarzyna; Rüttler, Felix; Tyśkiewicz, Renata; Nowak, Artur; Gruba, Marcin; Wziątek, Anita; Dębczak, Agnieszka; Sandomierski, Michał; Vetter, Walter; Cacciola, Francesco
The exploration of natural antifungal substances from algal origins is significant due to the increasing resistance of pathogens to conventional antifungal agents and the growing consumer demand for natural products. This manuscript represents the inaugural investigation into the antifungal attributes of bioactive compounds extracted from Fucus vesiculosus via supercritical carbon dioxide (scCO2) extraction utilizing contemporary countercurrent chromatography (CCC). In aligning with the prospective utilization of this extract within the agricultural sector, this study also serves as the preliminary report demonstrating the capability of Fucus vesiculosus scCO2 extract to enhance the activity of plant resistance enzymes. The fractions obtained through CCC were subjected to evaluation for their efficacy in inhibiting the macrospores of Fusarium culmorum. The CCC methodology facilitated the successful separation of fatty acids (reaching up to 82.0 wt.% in a given fraction) and fucosterol (attaining up to 79.4 wt.% in another fraction). All CCC fractions at the concentration of 1.0% were found to inhibit 100% of Fusarium culmorum growth. Moreover, Fucus vesiculosus scCO2 extract was able to activate plant resistance enzymes (Catalase, Ascorbic Peroxidase, Guaiacol Peroxidase, Phenylalanine Ammonia-Lyase, and Phenylalanine Ammonia-Lyase Activity).
Hydroxylated transformation products obtained after UV irradiation of the current-use brominated flame retardants hexabromobenzene, pentabromotoluene, and pentabromoethylbenzene
(2023) Klimm, Alexandra; Vetter, Walter
Hexabromobenzene (HBB), pentabromotoluene (PBT), and pentabromoethylbenzene (PBEB) are current-use brominated flame retardants (cuBFRs) which have been repeatedly detected in environmental samples. Since information on hydroxylated transformation products (OH-TPs) was scarcely available, the three polybrominated compounds were UV irradiated for 10 min in benzotrifluoride. Fractionation on silica gel enabled the separate collection and identification of OH-TPs. For more insights, aliquots of the separated OH-TPs were UV irradiated for another 50 min (60 min total UV irradiation time). The present investigation of polar UV irradiation products of HBB, PBT, and PBEB was successful in each case. Altogether, eight bromophenols were detected in the case of HBB (three Br3-, four Br4-, and one Br5-isomer), and nine OH-TPs were observed in the case of PBT/PBEB (six Br3- and three Br4-congeners). In either case, Br➔OH exchange was more relevant than H➔OH exchange. Also, such exchange was most relevant in meta- and ortho-positions. As a further point, and in agreement with other studies, the transformation rate decreased with decreasing degree of bromination. UV irradiation of HBB additionally resulted in the formation of tri- and tetrabrominated dihydroxylated compounds (brominated diphenols) that were subsequently identified. These dihydroxylated transformation products were found to be more stable than OH-TPs.
Effect of relative humidity on the thin-layer chromatographic separation of E 472 emulsifiers
(2023) Schuster, Katharina; Oellig, Claudia
E 472 emulsifiers are organic acid esters of mono- and diacylglycerides. These emulsifiers are categorized into six subgroups (E 472a-f) based on the specific acid component, e.g., acetic acid, lactic acid, citric acid, tartaric acid, or mixtures of tartaric and acetic acid. The present study investigated the effect of relative humidity (RH) on the thin-layer chromatographic separation of four E 472 emulsifier subgroups, addressing practical concerns due to RH variations between seasons and within laboratories. Three RH-setting techniques affecting plate activity and chamber climate were assessed using saturated salt and aqueous sulfuric acid solutions. Aqueous sulfuric acid solutions for RH adjustment resulted in decreased hRF values, while no trends in hRF value changes were observed for saturated salt solutions. Unlike RH itself, the RH setting technique led to substantial changes in the chromatographic fingerprint. Thus, the choice of the RH setting method should be tailored to the specific analyte and analysis goal. Despite variations in chromatographic fingerprints between the three RH setting techniques, the fingerprint remained consistent within the same technique across the tested RH range.
Analysis of acrylamide in vegetable chips after derivatization with 2-mercaptobenzoic acid by liquid chromatography–mass spectrometry
(2022) Oellig, Claudia; Gottstein, Eva; Granvogl, Michael
Since many years, acrylamide (AA) is a well-known toxicologically relevant processing contaminant (“food-borne toxicant”). However, only during the recent years, high levels of acrylamide have been reported in vegetable chips. In the present study, AA was quantitated via a modified derivatization procedure with 2-mercaptobenzoic acid based on stable isotope dilution analysis and liquid chromatography–mass spectrometry. Extraction with a modified QuEChERS (quick, easy, cheap, efficient, rugged, safe) method, defatting with n -hexane, and a solid phase extraction clean-up with strong cation-exchange material were performed prior to the derivatization step. Limits of detection and quantitation (LoD and LoQ) were 12 and 41 µg of AA/kg of vegetable chips (estimated via signal-to-noise ratios of 3:1 and 10:1, respectively), and thus below the LoQ of 50 µg/kg requested by the European Food Safety Authority. Recovery rates between 92 and 101% at four spiking levels with a good precision expressed as a relative standard deviation < 7% were determined. With this method at hand, a survey of the current AA amounts in 38 vegetable chips from the worldwide market was performed, showing a remarkable variability between the different vegetables, but also between different products of the same vegetable. Thereby, the AA amounts ranged between 77.3 and 3090 µg/kg, with an average of 954 µg/kg which was distinctly higher in comparison to commercially available potato chips also analyzed in the present study (12 samples, range: 117–832 µg/kg, average: 449 µg/kg). While for sweet potato and parsnip relatively low AA amounts were found, beetroot and carrot showed rather high contents.
High-performance thin-layer chromatography for the detection of compositional changes in LACTEM emulsifiers during storage
(2025) Schuster, Katharina; Blankart, Max; Hinrichs, Jörg; Oellig, Claudia
Quality control of food emulsifiers, such as lactic acid esters of mono- and diacylglycerols (LACTEM), is crucial in the reproducible production of food products. The current study investigated compositional changes of LACTEM emulsifiers using high-performance thin-layer chromatography (HPTLC) during storage at 60 °C for 8 weeks. Ultraviolet (UV) and fluorescence images of the HPTLC silica gel F254s plates after primuline derivatization and densitometric data were analyzed to assess changes in the composition. Significant changes were observed for minor LACTEM components (< 10% relative intensity), specifically a decrease in higher-lactylated monoacylglycerols and an increase in triacylglycerols. Techno-functional properties, such as particle size distribution, apparent viscosity, overrun, foam firmness, drainage, and residual cream of aerosol whipping cream (0.8 g 100 g−1 LACTEM) were investigated. While emulsion stability was not affected, the foam firmness increased significantly, corresponding to a visibly more brittle foam. On the basis of these results, monitoring compositional changes in the food-manufacturing process is necessary to maintain constant food quality.
Influence of distillation parameters on the fractionation behaviour of aroma compounds in the production of Williams-Christ pear brandies and Golden Delicious apple brandies
(2025) Yagishita, Manami; Vetter, Walter
Aroma compounds are central to the sensory attributes and overall organoleptic quality of fruit brandies, yet their behavior during distillation remains insufficiently understood. The relative volatility of these compounds, a fundamental property that defines their evaporation tendency in relation to ethanol, plays a crucial role in distillation, governing their separation efficiency, distribution between vapor and liquid phases, and overall impact on the composition and sensory quality of the final product. Despite its importance, the concept of relative volatility has not been introduced in the production of fruit brandies. The aim of the first publication was to develop a quick and simple method using a basic distillation apparatus to determine the relative volatilities of flavor compounds in hydro-alcoholic solutions. This approach provides a practical alternative to the time-consuming and costly Gillespie dynamic recirculation method. Seventeen representative flavor compounds from apple and pear brandies were investigated, including unpublished data for five compounds. Relative volatilities of methanol, isobutanol, isoamyl alcohol, ethyl acetate, acetaldehyde, and 1,1-diethoxyethane were compared to reference data, showing high correlation for all compounds except 1,1-diethoxyethane. Vapor-liquid equilibrium data for an ethanol-water mixture also exhibited strong agreement with reference data. These results demonstrate that the proposed method is a reliable, fast, and cost-effective alternative to standard techniques for determining relative volatilities. The second publication investigated the impact of partial condensation in dephlegmators on the behavior of ethanol and flavor compounds, comparing setups with and without dephlegmators in both lab-scale and large-scale experiments. Lab-scale experiments demonstrated that dephlegmation led to significant enrichment of ethanol in the distillate through the selective condensation of water. The behavior of flavor compounds varied, with some showing enrichment, others depletion, and some remaining unaffected. In large-scale experiments, a distillation apparatus relying solely on dephlegmation was compared with a standard setup containing an enrichment section with three trays. The dephlegmator-based system exhibited less efficient separation of tail components, such as fusel alcohols, resulting in a lower yield of hearts fraction. Sensory triangle tests confirmed that the spirits from the two systems were distinguishable, though no clear preference emerged. This study provides the first detailed insights into the influence of dephlegmators on flavor compound behavior and separation efficiency during fruit brandy distillation, offering valuable guidance for optimizing distillation processes. The third publication explored distillation processes from the perspective of relative volatility, aiming to control behaviors of key odor-active compounds in pear brandies and enhance product quality through novel fractionation strategies. Two novel fractionation strategies were tested: one involving a high cooling water flow rate combined with a slow distillate flow, and the other employing a 12-tray distillation column. Both approaches successfully increased ethanol concentration on the top tray, altering the relative volatility of compounds in the liquid phase. Elevated ethanol concentrations reduced the relative volatility of higher alcohols, delaying their release and producing sharper, well defined peaks compared to broader profiles observed in the control distillation. This enabled selective separation of desirable compounds, such as beta-damascenone and ethyl (E,Z)-2,4-decadienoate (pear ester), from higher alcohols, resulting in an aroma-rich tails fraction. Blending this enriched tails fraction with the hearts fraction produced a final product that was significantly preferred in sensory evaluations over the standard hearts fraction. These findings demonstrate the importance of tailoring operational distillation conditions to exploit differential volatility, enabling more effective compound separation and improving the sensory quality of fruit brandies.
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
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.
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.
A sterol database: GC/MS data and occurrence of 150 sterols in seventy-four oils
(2024) Schlag, Sarah; Schäfer, Sabrina; Sommer, Katrin; Vetter, Walter
Comprehensive data on the occurrence of sterols in plant oils is currently hardly available since only a few sterols are obtainable as standard compounds. Accordingly, many peaks are rarely labeled in gas chromatograms due to missing or outdated information. This lack of information hampers the progress in sterol research. For this reason, gas chromatography with mass spectrometry in selected ion monitoring mode (GC/MS-SIM) was used to create a database that summarizes the occurrence and semi-quantitative levels of 150 sterols with 27–32 carbon atoms and 0–4 double bonds in 66 different vegetable oils and eight other matrices. The highest number of sterols was detected in rice bran and tamanu oil (40 sterols), eggplant (39 sterols), moringa, chili seed, and amaranth oil (37 sterols). Several sterols were detected in >60 of the 74 matrices. This detailed information in the database will serve users working in food authentication and the biosynthesis of sterols.
Characterization of the key odorants in goji wines in three levels of sweetness by applications of sensomics approach
(2024) Zheng, Yan; Oellig, Claudia; Zhang, Youfeng; Liu, Yuan; Chen, Yanping; Zhang, Yanyan
The correlations and differences of the key odorants were systematically conducted among three sweetness of goji wines by the sensomics approach. After aroma (extract) dilution analysis, 67, 67, and 66 odorants were screened in sweet goji wine, semi-dry goji wine, and dry goji wine, in which, 63 odorants were identified in all goji wines. Determination of 53 odorants revealed a total of 30 odorants with the concentrations surpassing their olfactory thresholds. Overall, the odor activity values (OAVs) of ketones decreased, while esters, alcohols, phenols, and aldehydes increased with the decrease in sweetness in goji wine samples. Nevertheless, (E)-β-damascenone, trans- and cis-whisky lactones, and 3-methyl-2,4-nonanedione, evoked cooked apple-like, coconut-like, and hay-like odor impressions in goji wines and showed the highest OAVs. A reliable evaluation of the aroma contributions was executed as aroma recombinations and suggested a successful evaluation of key odorants in goji wines.
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.
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.
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.
Effect of the Mediterranean diet on the faecal long-chain fatty acid composition and intestinal barrier integrity: An exploratory analysis of the randomised controlled LIBRE trial
(2024) Seethaler, Benjamin; Basrai, Maryam; Neyrinck, Audrey M.; Vetter, Walter; Delzenne, Nathalie M.; Kiechle, Marion; Bischoff, Stephan C.
We recently showed that adherence to the Mediterranean diet increased the proportion of plasma n-3 PUFA, which was associated with an improved intestinal barrier integrity. In the present exploratory analysis, we assessed faecal fatty acids in the same cohort, aiming to investigate possible associations with intestinal barrier integrity. Women from the Lifestyle Intervention Study in Women with Hereditary Breast and Ovarian Cancer (LIBRE) randomised controlled trial, characterised by an impaired intestinal barrier integrity, followed either a Mediterranean diet (intervention group, n 33) or a standard diet (control group, n 35). At baseline (BL), month 3 (V1) and month 12 (V2), plasma lipopolysaccharide-binding protein, faecal zonulin and faecal fatty acids were measured. In the intervention group, faecal proportions of palmitoleic acid (16:1, n-7) and arachidonic acid (20:4, n-6) decreased, while the proportion of linoleic acid (18:2, n-6) and α linoleic acid (18:3, n-3) increased (BL-V1 and BL-V2, all P < 0·08). In the control group, faecal proportions of palmitic acid and arachidic acid increased, while the proportion of linoleic acid decreased (BL-V1, all P < 0·05). The decrease in the proportion of palmitoleic acid correlated with the decrease in plasma lipopolysaccharide-binding protein (ΔV1-BL r = 0·72, P < 0·001; ΔV2-BL r = 0·39, P < 0·05) and correlated inversely with adherence to the Mediterranean diet (Mediterranean diet score; ΔV1-BL r = –0·42, P = 0·03; ΔV2-BL r = -0·53, P = 0·005) in the intervention group. Our data show that adherence to the Mediterranean diet induces distinct changes in the faecal fatty acid composition. Furthermore, our data indicate that the faecal proportion of palmitoleic acid, but not faecal n-3 PUFA, is associated with intestinal barrier integrity in the intervention group.
Risk assessment of caffeine and epigallocatechin gallate in coffee leaf tea
(2022) Tritsch, Nadine; Steger, Marc C.; Segatz, Valerie; Blumenthal, Patrik; Rigling, Marina; Schwarz, Steffen; Zhang, Yanyan; Franke, Heike; Lachenmeier, Dirk W.
Coffee leaf tea is prepared as an infusion of dried leaves of Coffea spp. in hot water. It is a traditional beverage in some coffee-producing countries and has been authorized in 2020 within the European Union (EU) according to its novel food regulation. This article reviews current knowledge on the safety of coffee leaf tea. From the various ingredients contained in coffee leaves, only two were highlighted as possibly hazardous to human health, namely, caffeine and epigallocatechin gallate (EGCG), with maximum limits implemented in EU legislation, which is why this article focuses on these two substances. While the caffeine content is comparable to that of roasted coffee beans and subject to strong fluctuations in relation to the age of the leaves, climate, coffee species, and variety, a maximum of 1–3 cups per day may be recommended. The EGCG content is typically absent or below the intake of 800 mg/day classified as hepatotoxic by the European Food Safety Authority (EFSA), so this compound is suggested as toxicologically uncritical. Depending on selection and processing (age of the leaves, drying, fermentation, roasting, etc.), coffee leaf tea may exhibit a wide variety of flavors, and its full potential is currently almost unexplored. As a coffee by-product, it is certainly interesting to increase the income of coffee farmers. Our review has shown that coffee leaf tea is not assumed to exhibit risks for the consumer, apart from the well-known risk of caffeine inherent to all coffee-related beverages. This conclusion is corroborated by the history of its safe use in several countries around the world.
Effect of wort boiling on volatiles formation and sensory properties of mead
(2022) Starowicz, Małgorzata; Granvogl, Michael
Mead is an alcoholic beverage based on bee honey, which can be prepared in different variations such as modified honey-water compositions, the addition of spices, and the use of different yeast strains. Moreover, the technological process of mead production such as the step of wort preparation (with or without boiling of wort before fermentation) can be modified. All these factors might have a significant impact on the formation of aroma-active compounds, and therefore, sensory acceptance by consumers. High vacuum distillation, using the so-called solvent assisted flavor evaporation (SAFE) technique, or headspace-solid phase microextraction (HS-SPME) were applied for the isolation of the odorants. A sensory profile was used to monitor the changes in the aroma of the mead samples. Twenty-eight aroma-active compounds were detected during aroma extract dilution analysis (AEDA) based on gas chromatography-olfactometry (GC-O) and were finally identified by gas chromatography-mass spectrometry (GC-MS) using authentic reference compounds, including methyl propanoate, methyl 3-(methylthio)propanoate, and methional, all of them were identified for the first time in mead. Compounds with high flavor dilution (FD) factors were quantitated via stable isotope dilution analysis (SIDA) and revealed ethyl acetate (16.4 mg/L) to be the most abundant volatile compound, increasing to 57 mg/L after wort boiling, followed by ethyl hexanoate (both 1.2 mg/L). Furthermore, key aroma compounds were esters such as ethyl hexanoate, ethyl octanoate, and ethyl 3-methylbutanoate. The sensory panel evaluated ethanolic, honey-like, clove-like, sweet, and fruity notes as the main aroma descriptors of mead. The significant change in sensory evaluation was noted in the sweet odor of the heat-treated mead.
Tocochromanol profiles in Chlorella sorokiniana, Nannochloropsis limnetica and Tetraselmis suecica confirm the presence of 11′-α-tocomonoenol in cultured microalgae independently of species and origin
(2022) Montoya-Arroyo, Alexander; Lehnert, Katja; Muñoz-González, Alejandra; Schmid-Staiger, Ulrike; Vetter, Walter; Frank, Jan
11′-α-Tocomonoenol (11′-αT1) is structurally related to vitamin E and has been quantified in the microalgae Tetraselmis sp. and Nannochloropsis oceanica. However, it is not known whether 11′-αT1 is present in other microalgae independent of species and origin. The aim of this study was to analyze the tocochromanol profiles of Chlorella sorokiniana, Nannochloropsis limnetica, and Tetraselmis suecica and to determine if 11′-αT1 is present in these microalgae. Cultured microalgae were freeze-dried and the presence and identity of α-tocomonoenols were confirmed by LC-MSn (liquid chromatography coupled to mass spectroscopy) and GC-MS (gas chromatography coupled to mass spectroscopy). Tocochromanol profiles were determined by HPLC-FLD (liquid chromatography with fluorescence detection) and fatty acid profiles (as fatty acid methyl esters; FAME) by GC-MS. As confirmed by LC-MSn and GC-MS, 11′-αT1 was the dominant αT1 isomer in cultured microalgae instead of 12′-αT1, the isomer also known as marine-derived tocopherol. αT1 represented less than 1% of total tocochromanols in all analyzed samples and tended to be more abundant in microalgae with higher proportions of polyunsaturated fatty acids. In conclusion, our findings confirm that αT1 is not restricted to terrestrial photosynthetic organisms, but can also accumulate in microalgae of different species, with 11′-αT1—and not the marine-derived tocopherol (12′-αT1)—as the predominant αT1 isomer.
Exploration of surfactin production by newly isolated Bacillus and Lysinibacillus strains from food‐related sources
(2022) Akintayo, Stephen Olusanmi; Treinen, Chantal; Vahidinasab, Maliheh; Pfannstiel, Jens; Bertsche, Ute; Fadahunsi, I.; Oellig, Claudia; Granvogl, Michael; Henkel, Marius; Lilge, Lars; Hausmann, Rudolf
As a lipopeptide (LP), surfactin exhibits properties, such as emulsifying and dispersing ability, which are useful in food industry. Discovery of new LP‐producing strains from food sources is an important step towards possible application of surfactin in foods. A total of 211 spore‐forming, Gram‐positive, and catalase‐positive bacterial strains were isolated from fermented African locust beans (iru) and palm oil mill effluents in a screening process and examined for their ability to produce surfactin. This was achieved by a combination of methods, which included microbiological and molecular classification of strains, along with chemical analysis of surfactin production. Altogether, 29 isolates, positive for oil spreading and emulsification assays, were further identified with 16S rDNA analysis. The strains belonged to nine species including less commonly reported strains of Lysinibacillus, Bacillus flexus, B. tequilensis, and B. aryabhattai. The surfactin production was quantitatively and qualitatively analysed by high‐performance thin‐layer chromatography and liquid chromatography‐mass spectrometry (LC–MS). Confirmation of surfactin by MS was achieved in all the 29 strains. Highest surfactin production capability was found in B. subtilis IRB2‐A1 with a titre of 1444·1 mg L−1.
A fast gas chromatography coupled with electron capture negative ion mass spectrometry in selected ion monitoring mode screening method for short‐chain and medium‐chain chlorinated paraffins
(2022) Schweizer, Sina; Schulz, Tobias; Vetter, Walter
Rationale: Chlorinated paraffins (CPs) are a group of anthropogenic pollutants that consist of complex mixtures of polychlorinated n-alkanes of different chain lengths (~C10 to C30). Persistence, bioaccumulation, toxicity, and long-range transport of short-chain chlorinated paraffins (SCCPs, C10- to C13-CPs) have prompted their classification as persistent organic pollutants (POPs) by the Stockholm Convention in 2017. Due to the varying chain lengths and chlorination degrees, quantification of SCCPs and medium-chain chlorinated paraffins (MCCPs, C14- to C17) using gas chromatography coupled with electron capture negative ion mass spectrometry in selected ion monitoring mode (GC/ECNI-MS-SIM) is not only challenging but also very time consuming. In particular, up to eight GC runs per sample are required for the comprehensive GC/ECNI-MS-SIM quantification of SCCPs and MCCPs. These efforts are high especially if the samples do not contain CPs above the limit of detection (LOD), subsequently. Methods: We developed a semi-quantitative and sensitive method for the examination of SCCPs and MCCPs in one GC run. This GC/ECNI-MS-SIM screening method was based on the recording of Cl− (m/z 35 and 37), Cl2− (m/z 70 and 72), and HCl2− (m/z 71 and 73) isotope ions and evaluation of the ratios between them. Results: Correctness of the results of the screening method was verified by analysis of edible oils with and without CPs, CP standards, as well as a technical CP mixture. Polychlorinated biphenyls (PCBs) and other polyhalogenated aromatic compounds, as well as brominated flame retardants, do not form all of the fragment ions analyzed by the screening method. Conclusions: After the screening, only CP-positive samples may need to be measured in detail. Measurement time will already be gained in the case of ~10% samples without CPs.
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.

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