A5028655050- Plant biochemistry and biosynthesis
- Microbial Natural Products and Biosynthesis
- Natural product bioactivities and synthesis
- Sesquiterpenes and Asteraceae Studies
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Chemical synthesis and alkaloids
- Photosynthetic Processes and Mechanisms
- Plant Gene Expression Analysis
- Microbial Metabolic Engineering and Bioproduction
- Biocrusts and Microbial Ecology
- Enzyme Structure and Function
- Corrosion Behavior and Inhibition
- Hydrogen embrittlement and corrosion behaviors in metals
- Nitrogen and Sulfur Effects on Brassica
- Plant-derived Lignans Synthesis and Bioactivity
- Biochemical and Molecular Research
- Alkaloids: synthesis and pharmacology
- Insect Resistance and Genetics
- Traditional and Medicinal Uses of Annonaceae
- Carbohydrate Chemistry and Synthesis
- Essential Oils and Antimicrobial Activity
- Plant and fungal interactions
- Advanced Electron Microscopy Techniques and Applications
- Plant Toxicity and Pharmacological Properties
University of Bonn
2020-2025
Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry
2020
Chinese Academy of Sciences
2009-2019
Kunming Institute of Botany
2017-2019
University of Chinese Academy of Sciences
2019
Kunming University
2018-2019
China State Shipbuilding (China)
2004
The cyclization of farnesyl diphosphate (FPP) into highly strained polycyclic sesquiterpenes is challenging. We here determined the crystal structures three sesquiterpene synthases (STSs, namely, BcBOT2, DbPROS, and CLM1) catalyzing biosynthesis tricyclic presilphiperfolan-8β-ol (1), Δ6-protoilludene (2), longiborneol (3). All STS contain a substrate mimic, benzyltriethylammonium cation (BTAC), in their active sites, providing ideal templates for quantum mechanics/molecular mechanics (QM/MM)...
SUMMARY Ferns, known for their adaptability and widespread presence, form a diverse group of plants. However, the mechanisms underlying terpenoid production, which are often linked to plant adaptation, not well understood in ferns. Here, we report that Dryopteris fragrans ( D. fragans ) produces terpenoids glandular trichomes (GTs) through activities microbial‐type terpene synthases. Using microscopy methods, capitate GTs were found occur on various organs throughout development . In leaves,...
Abstract Little is known about the structures and catalytic mechanisms of sesterterpene synthases (StTSs), which greatly hinders structure‐based engineering StTSs for structural diversity expansion sesterterpenes. We here report on crystal terpene cyclization (TC) domains two fungal StTSs: sesterfisherol synthase (NfSS) sesterbrasiliatriene (PbSS). Both TC contain benzyltriethylammonium chloride (BTAC), pyrophosphate (PPi), magnesium ions (Mg 2+ ), clearly defining active sites. A...
Abstract The biosynthesis of six recently reported non‐canonical C 16 sesquiterpenoids named after ancient Greek philosophers, archimedene, aristotelene, eratosthenene, pythagorene, α‐democritene and anaximandrene, was investigated through density functional theory (DFT) calculations isotopic labeling experiments. results revealed for all compounds except archimedene a unique fragmentation‐recombination mechanism as previously demonstrated sodorifen biosynthesis, in addition to remarkable...
The crystal structures of cattleyene synthase (apo-CyS), and CyS complexed with geranylgeranyl pyrophosphate (GGPP) were solved.
A gene coding for a terpene synthase homolog from Kitasatospora viridis was cloned and expressed in Escherichia coli. The purified recombinant protein possessed sesterterpene activity efficiently converted geranylfarnesyl diphosphate (GFPP) with 19 % yield into the hydrocarbon sesterviridene A. Large scale enzymatic conversions also allowed isolation of two side products that are generated very low yields ca. 0.1 %. Several derivatives were obtained by chemical transformations, securing...
The sesquiterpene synthase 7-epi-α-eudesmol is widespread in streptomycetes. Several active site residues that were identified by an alignment of their amino acid sequence to the structurally known selina-4(15),7(11)-diene targeted site-directed mutagenesis. In these experiments, cavity was widened through exchange large with small residues, resulting discovery two key for which such exchanges turned into a di- or sesterterpene synthase.
The asterisca-1,6-diene synthase from the liverwort Radula lindenbergiana was functionally and mechanistically characterised, with implications also for long discussed biosynthesis of pentalenene.
Abstract A systematic computational study addressing the entire chemical space of guaianes in conjunction with an analysis all known compounds shows that 1,3‐hydride shifts are rare events guaiane biosynthesis. As demonstrated here, towards can only be realized for two stereochemically well defined out numerous possible stereoisomeric skeletons. One example is given by mechanism guaia‐4(15)‐en‐11‐ol synthase from California poplar, enzyme yields unusual stereochemical properties. The general...
Abstract During the past three decades many terpene synthases have been characterised from all kingdoms of life. Enzymes type I, bacteria, fungi and protists, commonly exhibit several highly conserved motifs single residues, available crystal structures show a shared α-helical fold, while overall sequence identity is generally low. Several enzymes studied by site-directed mutagenesis, giving valuable insights into synthase catalysis intriguing mechanisms synthases. Some mutants are also...
Abstract Die Biosynthese von sechs kürzlich beschriebenen nicht‐kanonischen C 16 ‐Sesquiterpenoiden, die nach antiken griechischen Philosophen benannt sind, darunter Archimeden, Aristotelen, Eratosthen, Pythagoren, α‐Democriten und Anaximandren, wurde durch Dichtefunktionaltheorie‐Rechnungen (DFT) Isotopenmarkierungsexperimente untersucht. Ergebnisse zeigten für alle Verbindungen außer Archimeden einen einzigartigen Fragmentierungs‐Rekombinationsmechanismus, wie er bereits...
The enantiomers (+)- and (−)-alternarilactone A (1), the first examples of dibenzo-α-pyrones bearing a diepoxy-cage-like moiety, were isolated from endophytic fungus Alternaria sp. hh930. deficiency in 1H–1H COSY HMBC correlations caused by highly oxidized caged system 1 deceptive ambiguous signals such as "W" couplings NMR data increased risk structure misassignment 1. By performing quantum chemical calculation shifts together with DP4+ probability analysis single-crystal X-ray...
Hedycaryol is a widespread sesquiterpene alcohol and important biosynthetic intermediate toward eudesmols guaiols. A full NMR assignment for this compound has been hampered because of the unique molecular mechanics its conformers in complex mixtures. This problem was solved through enzymatic synthesis isotopically labeled materials using mutated plant bacterial enzyme access to both enantiomers hedycaryol, which also allowed us follow stereochemical course Cope rearrangement.
The bacterial geosmin synthase is a fascinating bifunctional enzyme that has been discovered almost two decades ago. Several aspects of the cyclisation mechanism from FPP to are known, but detailed picture stereochemical course this reaction unknown. This article reports on deep investigation through isotopic labelling experiments. Furthermore, effects divalent cations catalysis were investigated. addition cyclodextrin enzymatic reactions, molecule can capture terpenes, suggests biosynthetic...
Abstract The changes of corrosion potential (E corr ) metals immersed in seawater were investigated with electrochemical technology and epifluoresence microscopy. In natural seawater, E determined by the surface state metal. passive exposed to shifted noble direction for about 150 mV one day it didn't change sterile seawater. in‐situ observation showed that biofilms settled on surfaces when moved direction. bacteria number increased metal according exponential law was same way ennoblement ....
A novel lanostane triterpenoid possessing an aromatic ring D, along with two norlanostane triterpenoids, were isolated from <italic>Kadsura coccinea</italic>.
Four new rearranged 6/6/5/6-fused lanostane-type triterpenoids, kadcoccitanes A–D (1–4), were isolated from the roots of Kadsura coccinea, and their structures mainly elucidated by comprehensive analysis spectroscopic data. Additionally, structure 1 was ambiguously verified single-crystal X-ray diffraction, while 2, which features a novel 8,16-epoxy motif, validated quantum chemical calculation NMR parameters ECD spectrum. Moreover, 4 found to exhibited anticoagulant activity, 3 possess...
The product of a terpene synthase from <italic>Streptomyces lincolnensis</italic> has been identified as the new natural isoishwarane. enzyme mechanism was studied by isotopic labelling experiments and site-directed mutagenesis.
Pathogen infection often leads to the enhanced formation of specialized plant metabolites that act as defensive barriers against microbial attackers. In this study, we investigated potential defense compounds in roots Western balsam poplar (Populus trichocarpa) upon with generalist root pathogen Phytophthora cactorum (Oomycetes). P. led an induced accumulation terpenes, aromatic compounds, and fatty acids roots. Transcriptome analysis uninfected cactorum-infected revealed a terpene synthase...
Different mechanisms for the cyclisation of farnesyl pyrophosphate to patchoulol by synthase are discussed in literature. They based on isotopic labelling experiments, but results from these experiments contradictory. The present work reports a reinvestigation biosynthesis and computational chemistry. favour pathway through neutral intermediates germacrene A α-bulnesene that both reactivated protonation further steps, while previously intra- intermolecular hydrogen transfers not supported....