Article
Chemistry, Medicinal
Philipp Schmidt, Christine Kolb, Andreas Reiser, Markus Philipp, Hans-Christian Mueller, Konstantin Karaghiosoff
Summary: This study reports the isolation and characterization of a methylene bridged dimer of naloxone, which can be formed via aldol addition and condensation reaction under acidic conditions and freely interconvert in solvent.
JOURNAL OF PHARMACEUTICAL SCIENCES
(2022)
Article
Chemistry, Analytical
Philipp Schmidt, Christine Kolb, Markus Godejohann, Andreas Reiser, Markus Philipp, Hans-Christian Mueller, Konstantin Karaghiosoff
Summary: In this study, we report the use of a hyphenated HPLC-DAD-HRMS/SPE NMR system for the separation and isolation of a complex mixture of esters. By utilizing this system, sixteen highly similar individual esters were successfully isolated and differentiated, demonstrating its applicability in pharmaceutical analysis and drug quality control.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2023)
Article
Plant Sciences
Chao Liang, Chi Ndi, Louise Kjaerulff, Susan Semple, Bevan Buirchell, Sonia Coriani, Birger Lindberg Moller, Dan Staerk
Summary: Extracts of Eremophila phyllopoda subsp. phyllopoda demonstrated inhibitory activity against alpha-glucosidase and PTP1B. Through extensive analysis, 21 previously undescribed serrulatane diterpenoids, two known serrulatane diterpenoids, and five known furofuran lignans were identified. These compounds showed potential as inhibitors against alpha-glucosidase and PTP1B.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Plant Sciences
Chao Liang, Chi Ndi, Louise Kjaerulff, Susan Semple, Bevan Buirchell, Sonia Coriani, Birger Lindberg Moller, Dan Staerk
Summary: Extracts of Eremophila phyllopoda subsp. phyllopoda exhibited inhibitory activity against alpha-glucosidase and PTP1B. Through high-resolution profiling, 21 new serrulatane diterpenoids and five known furofuran lignans were identified. The structures were elucidated using HRMS and NMR spectroscopic data. The compounds showed potential as inhibitors for alpha-glucosidase and PTP1B.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Biochemical Research Methods
Jing Jing, Tian Tian, Yang Wang, Xin Xu, Yuanhong Shan
Summary: In this study, a screening assay was developed to detect prohibited small peptides and related substances in urine. The method showed good purification effect for both basic and acidic peptides, expanding the coverage of detection substances. The method met the relevant criteria of WADA and was validated with satisfactory qualitative parameters.
JOURNAL OF CHROMATOGRAPHY A
(2022)
Review
Cell Biology
Christoph Seger, Sonja Sturm
Summary: NMR spectroscopy is essential for determining the structural information of analytes from natural sources in liquid state. While mass spectrometry can differentiate and group biomarkers, the structural characterization often requires the use of NMR spectroscopy.
Article
Biochemical Research Methods
Sachin D. Pawar, Gangasani J. Kumar, Aruna Chikkondra, Banwari Lal, P. Radhakrishnanand, Upadhyayula S. Murty, P. L. Sahu, Sachin Dubey, Arpit Soni, Pramod Kumar
Summary: Ethylmorphine and its metabolite nor-ethylmorphine are used for therapeutic purposes, with the synthesis of stable reference material being necessary for differentiation in doping control analysis in sports. In this study, nor-ethylmorphine HCl was synthesized and characterized, providing a reference material with high purity and potency suitable for doping control analysis in sports.
DRUG TESTING AND ANALYSIS
(2022)
Article
Agriculture, Multidisciplinary
Jesus Marin-Saez, Rosalia Lopez-Ruiz, Roberto Romero-Gonzalez, Antonia Garrido Frenich, Ismael Zamora Rico
Summary: A comprehensive evaluation of myclobutanil dissipation in tomato and grape samples was conducted, with a biphasic kinetic model providing a suitable adjustment. Six myclobutanil metabolites were identified, four of which were described for the first time. The degradation curves of the metabolites and the coformulants present in the commercial formulation were studied.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Analytical
Zheyuan Shi, Zhu Rao, Jun Zhao, Ming Liang, Tao Zhu, Yuan Wang, Hamidreza Arandiyan
Summary: The study optimized and validated an analytical method for nine kinds of OH-PAHs and one kind of NPAHs in environmental water samples, with a wide linear range, high correlation coefficients, and applicability in environmental water sample analysis.
Article
Biochemistry & Molecular Biology
Gertrud E. Morlock, Abera Belay, Julia Heil, Annabel Mehl, Hannelore Borck
Summary: Bioactive compounds in different types of Ethiopian monofloral honey were analyzed, revealing varying antibacterial, free-radical scavenging, and enzyme inhibitory activities. Some honeys showed low activity, while others showed strong and diverse activity profiles. High-performance thin-layer chromatography combined with multi-imaging and planar effect-directed assays proved to be an effective method. This study is valuable for quality designation, branding, and differentiation of honey, with implications for food science, nutrition, and the market.
Article
Environmental Sciences
Federica Dal Bello, Enrica Mecarelli, Riccardo Aigotti, Enrico Davoli, Paola Calza, Claudio Medana
Summary: Terpenes play a major role in the pleasant or unpleasant odors near active or inactive landfills. This study focused on the environmental degradation products of R-limonene and p-cymene using photocatalysis mediated by titanium dioxide. Mass spectrometry methods with GC and HPLC were developed to identify and characterize the transformation products derived from the photodegradation of these terpenes. The methods were then applied to real environmental samples from landfills in northern Italy, revealing the presence of transformation products together with R-limonene and p-cymene in both active and inactive landfills. These findings highlight the importance of reducing these molecules in the environment to minimize pollution and human risks.
JOURNAL OF ENVIRONMENTAL MANAGEMENT
(2022)
Article
Biochemistry & Molecular Biology
Iva Habinovec, Ivana Mikulandra, Lucia Ema Sekula, Jana Gasperov, Sasa Kazazic, Predrag Novak
Summary: LC-SPE/cryo NMR and MS methodologies have been developed and employed for rapid structure determination of 4'-tetrahydrofurfuryl macrozone reaction mixture components, showing high efficiency and low solvent consumption. The method is able to identify and structurally characterize main compounds even at low concentration levels, making it a reliable and effective platform for macrolides reaction components structure profiling.
Review
Chemistry, Analytical
Khaja Moinuddin Shaik, Bhaskar Sarmah, Gaurav Suresh Wadekar, Pramod Kumar
Summary: This review discusses the recent detection of nitrosamine impurities in pharmaceutical products, including various detection methods, mechanisms of action, sample preparation techniques, and regulatory limits.
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Hilal Kilinc, Gilda D'Urso, Annunziata Paolillo, Ozgen Alankus, Sonia Piacente, Milena Masullo
Summary: The application of metabolomics to the study of plants is growing due to the development of analytical techniques. LC-MS and 1H NMR were used to comprehensively analyze the phytochemical composition of Symphytum anatolicum, revealing the presence of various primary and specialized metabolites. The analysis also showed that Symphytum anatolicum is a rich source of metabolites with health-promoting activities.
Article
Biochemical Research Methods
Ignacio Perez-Victoria, Gloria Crespo, Fernando Reyes
Summary: The determination of amino acid chirality in natural peptides can be achieved through Marfey's analysis. However, for certain amino acids with a second chiral center, distinguishing between the two possible epimers can be challenging. This study presents a new approach using HPLC-SPE-NMR to overcome this challenge.
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Malene J. Petersen, Chao Liang, Louise Kjaerulff, Chi Ndi, Susan Semple, Bevan Buirchell, Sonia Coriani, Birger Lindberg Moller, Dan Staerk
Summary: Eremophila, a genus of Australian desert plants, has traditionally been used by Australian Aboriginal people for medicinal purposes. Extracts from Eremophila glabra showed inhibitory activity against alpha-glucosidase and protein tyrosine phosphatase 1B. The study identified new serrulatane diterpenoids and confirmed the presence of previously known compounds, some of which exhibited PTP1B inhibitory activities.
Article
Multidisciplinary Sciences
Elise Nordin, Stine K. Steffensen, Bente B. Laursen, Sven-Olof Andersson, Jan-Erik Johansson, Per Aman, Goran Hallmans, Michael Borre, Dan Staerk, Kati Hanhineva, Inge S. Fomsgaard, Rikard Landberg
Summary: In this study, a quantitative method for analysis of benzoxazinoids (BXs) was established, and the plasma levels of BXs after consumption of whole grain/bran rye or refined wheat were investigated in men with prostate cancer. The results showed that BX metabolites were significantly higher after rye consumption compared to refined wheat. Additionally, four BX-related metabolites were inversely associated with PSA levels in plasma. These findings suggest that rye may have potential preventive effects against prostate cancer.
SCIENTIFIC REPORTS
(2022)
Article
Plant Sciences
Susan J. Semple, Dan Staerk, Bevan J. Buirchell, Rachael M. Fowler, Oliver Gericke, Louise Kjaerulff, Yong Zhao, Hans Albert Pedersen, Malene J. Petersen, Line Fentz Rasmussen, Emilie Kold Bredahl, Gustav Blichfeldt Pedersen, Laura Mikel McNair, Chi P. Ndi, Nikolaj Lervad Hansen, Allison M. Heskes, Michael J. Bayly, Claus J. Loland, Nanna Heinz, Birger Lindberg Moller
Summary: In this study, we used DNA sequencing, chemical profiling, and molecular networking analyses to investigate the Eremophila genus and discovered new natural products and their bioactivities. Despite our intention to share the benefits with Australia's First Peoples according to the Nagoya Protocol, we encountered difficulties and conflicts in practice.
Article
Multidisciplinary Sciences
Karel Miettinen, Nattawat Leelahakorn, Aldo Almeida, Yong Zhao, Lukas Hansen, Iben Nikolajsen, Jens Andersen, Michael Givskov, Dan Staerk, Soren Bak, Sotirios Kampranis
Summary: The authors constructed yeast-based biosensors using G-protein coupled receptors to detect cannabinoids, screened agonists and antagonists, and developed a portable detection device.
NATURE COMMUNICATIONS
(2022)
Article
Microbiology
Lasse Kvich, Stephanie Crone, Mads H. Christensen, Rita Lima, Morten Alhede, Maria Alhede, Dan Staerk, Thomas Bjarnsholt
Summary: Pseudomonas aeruginosa is inhibited by Staphylococcus aureus in most in vitro settings. However, these two bacteria commonly coexist in chronically infected wounds and lungs of cystic fibrosis patients. This study identifies glucose-derived metabolites produced by S. aureus that efficiently eradicate P. aeruginosa, providing a potential explanation for their coexistence in chronic infections.
JOURNAL OF BACTERIOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Line Fentz Rasmussen, Jennifer Anton, Louise Kjaerulff, Yong Zhao, Susan J. Semple, Ndi Chi, Bevan Buirchell, Birger Lindberg Moller, Dan Staerk
Summary: This study investigated the root bark extract of the plant Eremophila longifolia and identified 12 previously unreported serrulatane diterpenoids. The structures of these compounds were determined through analysis techniques and NMR analysis. The study also found that some of these compounds exhibited weak inhibitory activity against targets important for managing type 2 diabetes.
Article
Multidisciplinary Sciences
Nikolaj Lervad Hansen, Louise Kjaerulff, Quinn Kalby Heck, Victor Forman, Dan Staerk, Birger Lindberg Moller, Johan Andersen-Ranberg
Summary: This study reports the identification and characterization of a group of cytochrome P450s in the medicinal plant Tripterygium wilfordii and their function in catalyzing the formation of triptonide. The authors demonstrate the biosynthesis pathway of triptonide and successfully produce triptonide in heterologous hosts. This finding lays the foundation for the production of diterpenoid triepoxides via fermentation.
NATURE COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Victor Forman, Dan Luo, Fernando Geu-Flores, Rene Lemcke, David R. Nelson, Sotirios C. Kampranis, Dan Staerk, Birger Lindberg Moller, Irini Pateraki
Summary: The ginkgo tree is considered a living fossil with a long history of morphological stasis. Its resilience is attributed to unique specialized metabolites. The study uncovers the early ginkgolide biosynthesis pathway.
NATURE COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Codruta Ignea, Morten H. Raadam, Aikaterini Koutsaviti, Yong Zhao, Yao-Tao Duan, Maria Harizani, Karel Miettinen, Panagiota Georgantea, Mads Rosenfeldt, Sara E. Viejo-Ledesma, Mikael A. Petersen, Wender L. P. Bredie, Dan Staerk, Vassilios Roussis, Efstathia Ioannou, Sotirios C. Kampranis
Summary: Specialized metabolites are crucial for medicine, flavors, fragrances, and biomaterials. However, their application potential is limited due to the small number of building blocks used in their biosynthesis. Engineering organisms to produce alternative building blocks can overcome this limitation and expand their applications.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Analytical
Yong Zhao, Oliver Gericke, Tuo Li, Louise Kjaerulff, Kenneth T. Kongstad, Allison Maree Heskes, Birger Lindberg Moller, Flemming Steen Jorgensen, Henrietta Venter, Sonia Coriani, Susan J. Semple, Dan Staerk
Summary: The development of sustainable and safe drugs to combat emerging health pandemics requires new analytical technologies to explore the unique chemical properties in Nature. In this study, a new analytical technology called polypharmacology-labeled molecular networking (PLMN) was introduced, which combined positive and negative ionization tandem mass spectrometry with polypharmacological high-resolution inhibition profiling data. By applying PLMN analysis to the crude extract of Eremophila rugosa, the antihyperglycemic and antibacterial constituents were identified, revealing their activity in different assays. Furthermore, 27 new non canonical nerylneryl diphosphate-derived diterpenoids were discovered, with serrulatane ferulate esters showing potential antihyperglycemic and antibacterial activities, including synergy with oxacillin in methicillin-resistant Staphylococcus aureus strains and saddle-shaped binding to the active site of protein tyrosine phosphatase 1B. PLMN holds promise for polypharmacological natural-products-based drug discovery.
ANALYTICAL CHEMISTRY
(2023)
Article
Plant Sciences
Chao Liang, Chi Ndi, Louise Kjaerulff, Susan Semple, Bevan Buirchell, Sonia Coriani, Birger Lindberg Moller, Dan Staerk
Summary: Extracts of Eremophila phyllopoda subsp. phyllopoda exhibited inhibitory activity against alpha-glucosidase and PTP1B. Through high-resolution profiling, 21 new serrulatane diterpenoids and five known furofuran lignans were identified. The structures were elucidated using HRMS and NMR spectroscopic data. The compounds showed potential as inhibitors for alpha-glucosidase and PTP1B.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Medicinal
Zahra Hasanpour, Peyman Salehi, Atousa Aliahmadi, Mahdieh Hoseinpour, Hossein Behboodi, Dan Staerk, Morteza Bararjanian
Summary: In this study, new 1,2,3-triazole-tethered analogs of N-northebaine were synthesized and their anti-bacterial properties were evaluated. Compounds 5b, 5j, and 5m showed strong activities against Staphylococcus aureus, surpassing the parent compound. These compounds and thebaine were also found to have potential as wound healing agents based on their cytotoxicity, proliferation, and anti-hemolytic activities. Compound 5j showed no inhibition of cell line growth and exhibited no hemolysis activity at different doses.
MEDICINAL CHEMISTRY RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Yong Zhao, Nikolaj L. Hansen, Yao-Tao Duan, Meera Prasad, Mohammed S. Motawia, Birger L. Moller, Irini Pateraki, Dan Staerk, Soren Bak, Karel Miettinen, Sotirios C. Kampranis
Summary: Researchers have identified a compound called celastrol in the roots of Tripterygium wilfordii, which has potential as an effective treatment for obesity. They have also developed a synthetic method for celastrol, allowing it to be produced from table sugar. This study demonstrates the successful combination of plant biochemistry, metabolic engineering, and chemistry for the scalable synthesis of complex specialized metabolites.
Article
Multidisciplinary Sciences
Davide Mancinotti, Katarzyna Czepiel, Jemma L. Taylor, Hajar Golshadi Galehshahi, Lillian A. Moller, Mikkel K. Jensen, Mohammed Saddik Motawia, Barbara Hufnagel, Alexandre Soriano, Likawent Yeheyis, Louise Kjaerulff, Benjamin Peret, Dan Staerk, Toni Wendt, Matthew N. Nelson, Magdalena Kroc, Fernando Geu-Flores
Summary: This study reveals that the sweet gene "pauper" in lupin encodes an acetyltransferase (AT) involved in the early QA pathway, leading to the accumulation of QAs and decreasing sweetness. Mutagenesis in narrow-leafed lupin reproduces the pauper chemotype, confirming the hypothesis. This research expands our understanding of QA biosynthesis and identifies the sweet gene in lupin for the first time, facilitating lupin breeding and domestication of other QA-containing legumes.
Article
Plant Sciences
Chao Liang, Chi Ndi, Louise Kjaerulff, Susan Semple, Bevan Buirchell, Sonia Coriani, Birger Lindberg Moller, Dan Staerk
Summary: Extracts of Eremophila phyllopoda subsp. phyllopoda demonstrated inhibitory activity against alpha-glucosidase and PTP1B. Through extensive analysis, 21 previously undescribed serrulatane diterpenoids, two known serrulatane diterpenoids, and five known furofuran lignans were identified. These compounds showed potential as inhibitors against alpha-glucosidase and PTP1B.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Biochemistry & Molecular Biology
Armando Moreno-Velasco, Mabel Fragoso-Serrano, Pedro de Jesus Flores-Tafoya, Sebastian Carrillo-Rojas, Elihu Bautista, Suzana Guimara Leitao, Jhon F. Castaneda-Gomez, Rogelio Pereda-Miranda
Summary: This study investigated the roots of Operculina hamiltonii, a traditional medicinal plant in Brazil. Three new acyl sugars or resin glycosides were identified and their structures elucidated. The combination of these compounds with other drugs showed enhanced cytotoxic effects on breast cancer cells.
Article
Biochemistry & Molecular Biology
Qian-Qing Liu, Lin-An Xiong, Jia-Yu Qian, Ting-Ting Gong, Lie-Feng Ma, Luo Fang, Zha-Jun Zhan
Summary: A new naturally occurring compound, Linderagatins C-F (1-4), with the structures of diaryltetrahydrofuran-type 7,9'-dinorlignans, was discovered in the roots of Lindera aggregata. The neuroprotective effects of compounds 2 and 3 on erastin-induced ferroptosis in HT-22 cells were found to be significant.
