Grapevine canes are an important source of bioactive compounds, such as stilbenoids. This study a... more Grapevine canes are an important source of bioactive compounds, such as stilbenoids. This study aimed to evaluate an in silico method, based on the Conductor-like Screening Model for Real Solvents (COSMO-RS) to isolate stilbenoids from a grapevine cane extract by offline heart-cut high-performance countercurrent chromatography (HPCCC). For the following extraction of resveratrol and ε-viniferin from grapevine canes, natural deep eutectic solvents (NADES) were used as an environmentally friendly alternative to the traditionally used organic solvents. In order to evaluate a variety of combinations of hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs) for the targeted extraction of stilbenoids, COSMO-RS was applied. In particular, ultrasonic-assisted extraction using a solvent mixture of choline chloride/1,2-propanediol leads to higher extraction yields of resveratrol and ε-viniferin. COSMO-RS calculations for NADES extraction combined with HPCCC biphasic solvent system cal...
This study presents the novel direct coupling of preparative high-speed counter-current chromatog... more This study presents the novel direct coupling of preparative high-speed counter-current chromatography with electrospray ionization mass spectrometry (HSCCC/ESI-MS–MS) for continuous MS data acquisition, and ‘target’-guided fractionation of polyphenolic compounds from sea buckthorn juice concentrate (Hippophaë rhamnoides L. ssp. rhamnoides, Elaeagnaceae). It was demonstrated that a combination of HSCCC and ESI-MS–MS is a versatile tool for fast screening and sensitive detection
International Journal of Pharmaceutics, Dec 1, 2017
Different methods are being deployed for non-viral DNA/RNA delivery. However non-viral formulatio... more Different methods are being deployed for non-viral DNA/RNA delivery. However non-viral formulations for DNA/RNA-delivery are often accompanied by severe toxicity and thus low efficiency. Particular costly cell culture media are required as well. Here we introduce sapofection as a valuable enhancing method for non-viral DNA/RNA delivery. Sapofection is based on the application of DNA/RNA nanoplexes and sapofectosid, a plant derived natural transfection reagent. Sapofectosid was produced from plant raw material by chromatographic methods and characterized by tandem mass spectrometry and intensive one and two dimensional NMR-spectroscopy. Sapofectosid did enhance the transfection efficiency of different DNA-and RNA-nanoplexes formulated with liposomes, polyethylenimine (PEI) or targeted and non-targeted oligo-lysine peptides. All nanoplexes were characterized physicochemically and the influence of sapofectosid on the nanoplex integrity was determined by DNA complexation assays. The nanoplexes and sapofectosid were administered to a variety of cancer cell lines and the transfection efficiency was investigated by flow cytometry and confocal microscopy. Dependent on the cell line the transfection efficiencies varied from 6 to 76%. The saponin-and receptor-mediated endocytosis of nanoplexes was investigated by flow cytometry. As demonstrated by impedance based live cell imaging sapofection was non-toxic. The findings show the great potential of sapofection to be used as an effective and nontoxic transfection enhancing method. Recently, we have reported that a complex extract of natural
A new chromatographic purification of single-walled carbon nanotubes using high-speed countercurr... more A new chromatographic purification of single-walled carbon nanotubes using high-speed countercurrent chromatography is reported. The purification was accomplished on the basis of experiment that dispersed the single-walled carbon nanotubes with sodium dodecyl sulfate, and the result mixture was separated using the two phase system composed of n-butanol/water = 1/1 (v/v). The sizes of SWNTs separated were observed by scanning electron microscopy. The results demonstrated that the high-speed countercurrent chromatography possessed a good efficency for purification of single-walled carbon nanotubes.
International Journal of Pharmaceutics, Nov 1, 2020
Transfection is the process to deliver nucleic acid into eukaryotic cells. Different transfection... more Transfection is the process to deliver nucleic acid into eukaryotic cells. Different transfection techniques already exist. However, they can be expensive and toxic toward subjected cells. Previous research shed light on natural occurring molecules called triterpene saponins that have great potential for the non-viral gene delivery. Using a combination of different chromatographic techniques and in vitro transfection bioassays, a new triterpenoid saponin (agrostemmoside E) from the plant Agrostemma githago L. was isolated. Agrostemmoside E was characterized by mass spectrometry, intense NMR spectroscopy and was identified as 3-{O-ß-D-Galactopyranosyl-(1→2)]-[ß-D-xylopyranosyl-(1→3)]-ß-D-glucuronopyranosyl} quillaic acid 28-O-{[ß-D-4,6-di-(O-acetyl)-glucopyranosyl-(1→3)]-[ß-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)}-[3,4-di-(O-acetyl)-ß-D-quinovopyranosyl-(1→4)]-ß-D-fucopyranoside ester. Agrostemmoside E has a great potential for delivery of gene loaded nanoplexes and increased the transfection efficiency by 70% compared to 2% without agrostemmoside E. By comparative toxicity studies, we show that agrostemmoside E can be applied at high concentrations without toxicity, justifying its use as a new tool for gene transfections.
The 10th International Countercurrent Chromatography Conference (CCC 2018) was held at Technische... more The 10th International Countercurrent Chromatography Conference (CCC 2018) was held at Technische Universität Braunschweig, Germany, from August 1st-3rd, 2018. The presentations in the scientific program demonstrated the progress in the field of countercurrent chromatography (CCC) and centrifugal partition chromatography (CPC) in recent years and numerous applications have impressively proven the potential of this all-liquid separation technique not only for academic research but also for industry. Special highlights of the conference were the celebration of the 90th birthday of Dr. Yoichiro Ito, the pioneer of countercurrent chromatography, as well as the foundation of an international "Society of Partition and Countercurrent Chromatography (SPCC)".
Pyrrolizidine alkaloids (PAs) are genotoxic natural products. Almost 350 PAs are known with respe... more Pyrrolizidine alkaloids (PAs) are genotoxic natural products. Almost 350 PAs are known with respective N-oxides. Legal regulations of PAs in food, and feed are discussed. There is a lack of available reference substances for targeted quantification [1]. PA-contamination was reported for honey, and bee products [2,3]. PA-contamination of retail ready-to-use lettuce was demonstrated. Morphological similarities of rocket salad (Diplotaxis tenuifolia, syn.: rucola), and the PA-plant Senecio vulgaris resulted in unintentional co-harvesting. In our study, PA-extract of J. vulgaris flower heads (Asteraceae) was fractionated by prep. spiral-coil countercurrent chromatography (spCCC, 5.7 L coil). The system n-hexane – EtOAc – MeOH – H2O (3:7:5:5) was used to separate 5 g of crude alkaloid extract. Obtained fractions were sequentially off-line injected to ESI-MS/MS. This target-guided isolation procedure [4] made use of selected ion traces of PAs. Elution of major (2, 5, 7), and minor (1, 3, 4, 6) PAs were monitored (altern. mode MS2, m/z 100 – 1500). The spCCC elution resulted in the fractionation of PAs, and one non-PA (8) in the extrusion-mode (8 not presented) [5]. Almost pure compounds were obtained for PAs 1, 2, 5, 7, and the non-PA 8 could be used as reference materials. Minor PAs were enriched and will be further purified with other separation techniques. References: [1] BfR, Nr. 038/2011, http://www.bfr.bund.de/cm/343/analytik-und-toxizitaet-von-pyrrolizidinalkaloiden.pdf [2] Kempf et al., Mol. Nutr. Food Res. 2010, 54, 158. [3] Kempf et al., Food Addit. Contam., Part A, 2011, 28, 325. [4] Jerz et al., In: ACS Symp. Series 1098; 2012. [5] Fragoso-Serrano et al., J. Nat. Prod. 2012, 75, 890.
Opuntia stricta var. dillenii and Atriplex hortensis var. rubra, two plant species with abundant ... more Opuntia stricta var. dillenii and Atriplex hortensis var. rubra, two plant species with abundant betalain and flavonoid content, were studied by high performance countercurrent chromatography (HPCCC) coupled with ESI-MS/MS in an off-line detection process. Both CCC runs used tert.-butyl-methyl-ether/n-butanol/acetonitrile/water 1% trifluoroacetic acid (v/v/v/v, 2:2:1:5) as a biphasic solvent system within an elution-extrusion mode. The resulting fractions were scanned by an off-line sequential injection to ESI-MS/MS approach. The separation of Opuntia stricta var. dillenii extract showed a partial isolation of principal betalains (betanin) from their derivatives (betanidin, phyllocactin, feruloyl-betanin, betaxanthin), degraded products (hydroxyl-neobetanin, mono decarboxy-betanins), and flavonoid glycosides (isorhamnetin-rutinoside, kaempferol-rutinoside). In case of Atriplex hortensis var. rubra, this study confirmed the coexistence of several flavonoids (quercetin-O-malonyl gluco...
Highlights Off-line electrospray mass-spectrometry of countercurrent chromatography fractions ... more Highlights Off-line electrospray mass-spectrometry of countercurrent chromatography fractions Analytical and semi-preparative elution profiles monitored by single ion traces Accurate measurement of compound retention volumes, peak widths and co-elution Partition ratio KD based metabolite projection in countercurrent chromatography Detection of forthy-three metabolites and identification of twenty by fragmentation
Zeitschrift für Kristallographie - New Crystal Structures, 2016
The crystal structure is shown in the gure. Tables 1-3 contain details of the measurement method ... more The crystal structure is shown in the gure. Tables 1-3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of material Plant material of Heliotropium taltalense (Phil.) I. M. Johnst. (aerial parts) were collected in Quebrada de Paposo in
Peanut hulls (Arachis hypogaea, Leguminosae), which are a side stream of global peanut processing... more Peanut hulls (Arachis hypogaea, Leguminosae), which are a side stream of global peanut processing, are rich in bioactive flavonoids such as luteolin, eriodictyol, and 5,7-dihydroxychromone. This study aimed to isolate these flavonoid derivatives by liquid-liquid chromatography with as few steps as possible. To this end, luteolin, eriodictyol and 5,7-dihydroxychromone were isolated from peanut hulls using two different techniques, high-performance countercurrent chromatography (HPCCC) and fast-centrifugal partition chromatography (FCPC). The suitability of the biphasic solvent system composed of n-hexane/ethyl acetate/methanol/water (1.0/1.0/1.0/1.5; v/v/v/v) was determined by the Conductor like Screening Model for Real Solvents (COSMO-RS), which allowed the partition ratio KD-values of the three main flavonoids to be calculated. After a one-step HPCCC separation of ~1000 mg of an ethanolic peanut hull extract, 15 mg of luteolin and 8 mg of eriodictyol were isolated with purities ove...
Previously, different Hydrangea macrophylla ssp. serrata cultivars were investigated by untargete... more Previously, different Hydrangea macrophylla ssp. serrata cultivars were investigated by untargeted LC-MS analysis. From this, a list of tentatively identified and unknown compounds that differ significantly between these cultivars was obtained. Due to the lack of reference compounds, especially for dihydro-isocoumarins, we aimed to isolate and structurally characterise these compounds from the cultivar ‘Yae-no-amacha’ using NMR and LC-MS methods. For purification and isolation, counter-current chromatography was used in combination with reversed-phase preparative HPLC as an orthogonal and enhanced purification workflow. Thirteen dihydro-isocoumarins in combination with other metabolites could be isolated and structurally identified. Particularly interesting was the clarification of dihydrostilbenoid glycosides, which were described for the first time in H. macrophylla ssp. serrata. These results will help us in further studies on the biological interpretation of our data.
Grapevine canes are an important source of bioactive compounds, such as stilbenoids. This study a... more Grapevine canes are an important source of bioactive compounds, such as stilbenoids. This study aimed to evaluate an in silico method, based on the Conductor-like Screening Model for Real Solvents (COSMO-RS) to isolate stilbenoids from a grapevine cane extract by offline heart-cut high-performance countercurrent chromatography (HPCCC). For the following extraction of resveratrol and ε-viniferin from grapevine canes, natural deep eutectic solvents (NADES) were used as an environmentally friendly alternative to the traditionally used organic solvents. In order to evaluate a variety of combinations of hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs) for the targeted extraction of stilbenoids, COSMO-RS was applied. In particular, ultrasonic-assisted extraction using a solvent mixture of choline chloride/1,2-propanediol leads to higher extraction yields of resveratrol and ε-viniferin. COSMO-RS calculations for NADES extraction combined with HPCCC biphasic solvent system cal...
This study presents the novel direct coupling of preparative high-speed counter-current chromatog... more This study presents the novel direct coupling of preparative high-speed counter-current chromatography with electrospray ionization mass spectrometry (HSCCC/ESI-MS–MS) for continuous MS data acquisition, and ‘target’-guided fractionation of polyphenolic compounds from sea buckthorn juice concentrate (Hippophaë rhamnoides L. ssp. rhamnoides, Elaeagnaceae). It was demonstrated that a combination of HSCCC and ESI-MS–MS is a versatile tool for fast screening and sensitive detection
International Journal of Pharmaceutics, Dec 1, 2017
Different methods are being deployed for non-viral DNA/RNA delivery. However non-viral formulatio... more Different methods are being deployed for non-viral DNA/RNA delivery. However non-viral formulations for DNA/RNA-delivery are often accompanied by severe toxicity and thus low efficiency. Particular costly cell culture media are required as well. Here we introduce sapofection as a valuable enhancing method for non-viral DNA/RNA delivery. Sapofection is based on the application of DNA/RNA nanoplexes and sapofectosid, a plant derived natural transfection reagent. Sapofectosid was produced from plant raw material by chromatographic methods and characterized by tandem mass spectrometry and intensive one and two dimensional NMR-spectroscopy. Sapofectosid did enhance the transfection efficiency of different DNA-and RNA-nanoplexes formulated with liposomes, polyethylenimine (PEI) or targeted and non-targeted oligo-lysine peptides. All nanoplexes were characterized physicochemically and the influence of sapofectosid on the nanoplex integrity was determined by DNA complexation assays. The nanoplexes and sapofectosid were administered to a variety of cancer cell lines and the transfection efficiency was investigated by flow cytometry and confocal microscopy. Dependent on the cell line the transfection efficiencies varied from 6 to 76%. The saponin-and receptor-mediated endocytosis of nanoplexes was investigated by flow cytometry. As demonstrated by impedance based live cell imaging sapofection was non-toxic. The findings show the great potential of sapofection to be used as an effective and nontoxic transfection enhancing method. Recently, we have reported that a complex extract of natural
A new chromatographic purification of single-walled carbon nanotubes using high-speed countercurr... more A new chromatographic purification of single-walled carbon nanotubes using high-speed countercurrent chromatography is reported. The purification was accomplished on the basis of experiment that dispersed the single-walled carbon nanotubes with sodium dodecyl sulfate, and the result mixture was separated using the two phase system composed of n-butanol/water = 1/1 (v/v). The sizes of SWNTs separated were observed by scanning electron microscopy. The results demonstrated that the high-speed countercurrent chromatography possessed a good efficency for purification of single-walled carbon nanotubes.
International Journal of Pharmaceutics, Nov 1, 2020
Transfection is the process to deliver nucleic acid into eukaryotic cells. Different transfection... more Transfection is the process to deliver nucleic acid into eukaryotic cells. Different transfection techniques already exist. However, they can be expensive and toxic toward subjected cells. Previous research shed light on natural occurring molecules called triterpene saponins that have great potential for the non-viral gene delivery. Using a combination of different chromatographic techniques and in vitro transfection bioassays, a new triterpenoid saponin (agrostemmoside E) from the plant Agrostemma githago L. was isolated. Agrostemmoside E was characterized by mass spectrometry, intense NMR spectroscopy and was identified as 3-{O-ß-D-Galactopyranosyl-(1→2)]-[ß-D-xylopyranosyl-(1→3)]-ß-D-glucuronopyranosyl} quillaic acid 28-O-{[ß-D-4,6-di-(O-acetyl)-glucopyranosyl-(1→3)]-[ß-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)}-[3,4-di-(O-acetyl)-ß-D-quinovopyranosyl-(1→4)]-ß-D-fucopyranoside ester. Agrostemmoside E has a great potential for delivery of gene loaded nanoplexes and increased the transfection efficiency by 70% compared to 2% without agrostemmoside E. By comparative toxicity studies, we show that agrostemmoside E can be applied at high concentrations without toxicity, justifying its use as a new tool for gene transfections.
The 10th International Countercurrent Chromatography Conference (CCC 2018) was held at Technische... more The 10th International Countercurrent Chromatography Conference (CCC 2018) was held at Technische Universität Braunschweig, Germany, from August 1st-3rd, 2018. The presentations in the scientific program demonstrated the progress in the field of countercurrent chromatography (CCC) and centrifugal partition chromatography (CPC) in recent years and numerous applications have impressively proven the potential of this all-liquid separation technique not only for academic research but also for industry. Special highlights of the conference were the celebration of the 90th birthday of Dr. Yoichiro Ito, the pioneer of countercurrent chromatography, as well as the foundation of an international "Society of Partition and Countercurrent Chromatography (SPCC)".
Pyrrolizidine alkaloids (PAs) are genotoxic natural products. Almost 350 PAs are known with respe... more Pyrrolizidine alkaloids (PAs) are genotoxic natural products. Almost 350 PAs are known with respective N-oxides. Legal regulations of PAs in food, and feed are discussed. There is a lack of available reference substances for targeted quantification [1]. PA-contamination was reported for honey, and bee products [2,3]. PA-contamination of retail ready-to-use lettuce was demonstrated. Morphological similarities of rocket salad (Diplotaxis tenuifolia, syn.: rucola), and the PA-plant Senecio vulgaris resulted in unintentional co-harvesting. In our study, PA-extract of J. vulgaris flower heads (Asteraceae) was fractionated by prep. spiral-coil countercurrent chromatography (spCCC, 5.7 L coil). The system n-hexane – EtOAc – MeOH – H2O (3:7:5:5) was used to separate 5 g of crude alkaloid extract. Obtained fractions were sequentially off-line injected to ESI-MS/MS. This target-guided isolation procedure [4] made use of selected ion traces of PAs. Elution of major (2, 5, 7), and minor (1, 3, 4, 6) PAs were monitored (altern. mode MS2, m/z 100 – 1500). The spCCC elution resulted in the fractionation of PAs, and one non-PA (8) in the extrusion-mode (8 not presented) [5]. Almost pure compounds were obtained for PAs 1, 2, 5, 7, and the non-PA 8 could be used as reference materials. Minor PAs were enriched and will be further purified with other separation techniques. References: [1] BfR, Nr. 038/2011, http://www.bfr.bund.de/cm/343/analytik-und-toxizitaet-von-pyrrolizidinalkaloiden.pdf [2] Kempf et al., Mol. Nutr. Food Res. 2010, 54, 158. [3] Kempf et al., Food Addit. Contam., Part A, 2011, 28, 325. [4] Jerz et al., In: ACS Symp. Series 1098; 2012. [5] Fragoso-Serrano et al., J. Nat. Prod. 2012, 75, 890.
Opuntia stricta var. dillenii and Atriplex hortensis var. rubra, two plant species with abundant ... more Opuntia stricta var. dillenii and Atriplex hortensis var. rubra, two plant species with abundant betalain and flavonoid content, were studied by high performance countercurrent chromatography (HPCCC) coupled with ESI-MS/MS in an off-line detection process. Both CCC runs used tert.-butyl-methyl-ether/n-butanol/acetonitrile/water 1% trifluoroacetic acid (v/v/v/v, 2:2:1:5) as a biphasic solvent system within an elution-extrusion mode. The resulting fractions were scanned by an off-line sequential injection to ESI-MS/MS approach. The separation of Opuntia stricta var. dillenii extract showed a partial isolation of principal betalains (betanin) from their derivatives (betanidin, phyllocactin, feruloyl-betanin, betaxanthin), degraded products (hydroxyl-neobetanin, mono decarboxy-betanins), and flavonoid glycosides (isorhamnetin-rutinoside, kaempferol-rutinoside). In case of Atriplex hortensis var. rubra, this study confirmed the coexistence of several flavonoids (quercetin-O-malonyl gluco...
Highlights Off-line electrospray mass-spectrometry of countercurrent chromatography fractions ... more Highlights Off-line electrospray mass-spectrometry of countercurrent chromatography fractions Analytical and semi-preparative elution profiles monitored by single ion traces Accurate measurement of compound retention volumes, peak widths and co-elution Partition ratio KD based metabolite projection in countercurrent chromatography Detection of forthy-three metabolites and identification of twenty by fragmentation
Zeitschrift für Kristallographie - New Crystal Structures, 2016
The crystal structure is shown in the gure. Tables 1-3 contain details of the measurement method ... more The crystal structure is shown in the gure. Tables 1-3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of material Plant material of Heliotropium taltalense (Phil.) I. M. Johnst. (aerial parts) were collected in Quebrada de Paposo in
Peanut hulls (Arachis hypogaea, Leguminosae), which are a side stream of global peanut processing... more Peanut hulls (Arachis hypogaea, Leguminosae), which are a side stream of global peanut processing, are rich in bioactive flavonoids such as luteolin, eriodictyol, and 5,7-dihydroxychromone. This study aimed to isolate these flavonoid derivatives by liquid-liquid chromatography with as few steps as possible. To this end, luteolin, eriodictyol and 5,7-dihydroxychromone were isolated from peanut hulls using two different techniques, high-performance countercurrent chromatography (HPCCC) and fast-centrifugal partition chromatography (FCPC). The suitability of the biphasic solvent system composed of n-hexane/ethyl acetate/methanol/water (1.0/1.0/1.0/1.5; v/v/v/v) was determined by the Conductor like Screening Model for Real Solvents (COSMO-RS), which allowed the partition ratio KD-values of the three main flavonoids to be calculated. After a one-step HPCCC separation of ~1000 mg of an ethanolic peanut hull extract, 15 mg of luteolin and 8 mg of eriodictyol were isolated with purities ove...
Previously, different Hydrangea macrophylla ssp. serrata cultivars were investigated by untargete... more Previously, different Hydrangea macrophylla ssp. serrata cultivars were investigated by untargeted LC-MS analysis. From this, a list of tentatively identified and unknown compounds that differ significantly between these cultivars was obtained. Due to the lack of reference compounds, especially for dihydro-isocoumarins, we aimed to isolate and structurally characterise these compounds from the cultivar ‘Yae-no-amacha’ using NMR and LC-MS methods. For purification and isolation, counter-current chromatography was used in combination with reversed-phase preparative HPLC as an orthogonal and enhanced purification workflow. Thirteen dihydro-isocoumarins in combination with other metabolites could be isolated and structurally identified. Particularly interesting was the clarification of dihydrostilbenoid glycosides, which were described for the first time in H. macrophylla ssp. serrata. These results will help us in further studies on the biological interpretation of our data.
Uploads
Papers by Gerold Jerz