0000000001307862

AUTHOR

Christoph Janiak

showing 23 related works from this author

Anorganische Chemie 2002

2003

In der anorganischen Molekulchemie sind Mehrfachbindungssysteme, Kationen und „stabile” Radikale wieder starker ins Rampenlicht geruckt. Aktivierung kleiner Molekule und Sensorik mit Metallkomplexen sind zwei Forschungsschwerpunkte der Koordinationschemie. Die Suche nach biomimetischen Modellverbindungen geht weiter; Taktgeber des Fortschritts in der Bioanorganischen Chemie ist weiterhin die Proteinkristallographie.

General Chemical EngineeringGeneral ChemistryNachrichten aus der Chemie
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Indole Diterpenoids from an Endophytic Penicillium sp.

2019

A chemical investigation of the endophyte Penicillium sp. (strain ZO-R1-1), isolated from roots of the medicinal plant Zingiber officinale, yielded nine new indole diterpenoids (1-9), together with 13 known congeners (10-22). The structures of the new compounds were elucidated by 1D and 2D NMR analysis in combination with HRESIMS data. The absolute configuration of the new natural products 1, 3, and 7 was determined using the TDDFT-ECD approach and confirmed for 1 by single-crystal X-ray determination through anomalous dispersion. The isolated compounds were tested for cytotoxicity against L5178Y, A2780, J82, and HEK-293 cell lines. Compound 1 was the most active metabolite toward L5178Y ce…

IndolesMagnetic Resonance SpectroscopyStereochemistryPharmaceutical ScienceAntineoplastic Agents01 natural sciencesEndophyteAnalytical Chemistrychemistry.chemical_compoundTermészettudományokCell Line TumorDrug DiscoveryEndophytesHumansKémiai tudományokPharmacologyIndole testOvarian NeoplasmsBiological ProductsNatural productbiology010405 organic chemistryOrganic ChemistryAbsolute configurationPenicilliumNuclear magnetic resonance spectroscopybiology.organism_classificationTerpenoid0104 chemical sciences010404 medicinal & biomolecular chemistryHEK293 CellsComplementary and alternative medicinechemistryPenicilliumMolecular MedicineFemaleDiterpenesTwo-dimensional nuclear magnetic resonance spectroscopyJournal of natural products
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Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

2016

Seven new brominated tyrosine-derived alkaloids, gymnastatins T–Y (1–6) and dankastatin D (7), together with three known likewise brominated analogues gymnastatins I–K (8–10) were isolated from the soil fungus Gymnascella dankaliensis through fermentation on solid rice medium following addition of NaBr. None of these compounds were detected when the fungus was cultured on rice that either lacked NaBr or that contained NaCl instead, indicating a remarkable plasticity of the fungal secondary metabolism. All structures were elucidated on the basis of one and two dimensional NMR spectroscopic analyses and MS data. The absolute configuration of the new gymnastatin T (1) was determined by X-ray c…

biology010405 organic chemistryChemistryStereochemistryGeneral Chemical EngineeringAbsolute configurationGeneral ChemistryFungus010402 general chemistrybiology.organism_classification01 natural sciences0104 chemical sciencesCell culturePhase (matter)Organic chemistryFermentationTyrosineCytotoxicitySecondary metabolismRSC Advances
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Fusaristatins D–F and (7S,8R)-(−)-chlamydospordiol from Fusarium sp. BZCB-CA, an endophyte of Bothriospermum chinense

2021

Abstract Three new lipodepsipeptides, fusaristatins D–F (1–3) and a new α-pyrone derivative, (7S,8R)-(−)-chlamydospordiol (5), together with eight known compounds (4, 6–12) were obtained from solid rice cultures of Fusarium sp. BZCB-CA, an endophyte of the Chinese medicinal plant, Bothriospermum chinense. The planar structures of the new metabolites (1–3, 5) were established by spectroscopic techniques (1D/2D NMR and HRESIMS). Marfey’s method was applied to determine the absolute configuration of 1, while the absolute configuration of 5 was determined by single-crystal X-ray crystallography analysis in addition to Mosher’s method. Crystallographic data of inflatin C (7) are also supplied he…

Fusariumbiology010405 organic chemistryStereochemistryOrganic ChemistryAbsolute configuration010402 general chemistryBothriospermum chinensebiology.organism_classification01 natural sciencesBiochemistryEndophyte0104 chemical scienceschemistry.chemical_compoundchemistryDrug DiscoveryCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyDerivative (chemistry)BacteriaTetrahedron
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Experimental and Theoretical Investigations on the Synthesis, Structure, Reactivity, and Bonding of the Stannylene-Iron Complex Bis{{bis(2-tert-butyl…

2000

The pi-(arene)bis(stannylene) complex bis(bis(2-tert-butyl-4,5,6-trimethylphenyl)SnFe(eta6-toluene) (Sn-Fe-Sn, 15) is accessible in high yields by a metal-atom-mediated synthesis between iron atoms, toluene, and the stannylene [bis(2-tert-butyl-4,5,6-trimethylphenyl)Sn](3). Complex 15 has a half-sandwich structure with short Fe -Sn bonds (2.432(1) A) and a trigonal-planar coordination at both the Fe and Sn atoms. The distance between the two Sn centers is 3.56 A. Complex 15 is stable under ambient conditions and displays a pi-arene lability, so far rarely observed for (arene)iron complexes; this leads to an irreversible substitution of the arene and formation of fivefold-coordinated zeroval…

Zerovalent ironLabilityOrganic ChemistryInorganic chemistryChemiechemistry.chemical_elementGeneral ChemistryAcceptorTolueneCatalysisCrystallographychemistry.chemical_compoundchemistryAtomic orbitalMolecular orbitalTinPi backbonding
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Secondary metabolites of the lichen-associated fungus Apiospora montagnei

2017

Abstract The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl w…

biology010405 organic chemistryStereochemistryAlkaloidOrganic ChemistryAbsolute configurationEtherbiology.organism_classification01 natural sciencesBiochemistryTerpenoid0104 chemical sciences010404 medicinal & biomolecular chemistrychemistry.chemical_compoundchemistryDrug DiscoveryXanthoneOrganic chemistryApiosporaTwo-dimensional nuclear magnetic resonance spectroscopyDerivative (chemistry)Tetrahedron Letters
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Sesquiterpenoids from the Endophytic Fungus Rhinocladiella similis

2019

Ten new sesquiterpenoid derivatives, rhinomilisins A-J (1-10), along with six known analogues (11-16), were isolated from the mangrove-derived endophytic fungus Rhinocladiella similis. The structures of the new compounds were elucidated by their NMR and MS data, while the absolute configuration of 3 and 6 was determined by X-ray crystallographic analysis and Mosher's method, respectively. All isolated compounds (1-16) were evaluated for their cytotoxicity against the mouse lymphoma cell line L5178Y, and compounds 1, 7, and 15 showed moderate activity with IC50 values of 5.0, 8.7, and 24.4 μM, respectively.

Magnetic Resonance SpectroscopyStereochemistryPharmaceutical ScienceModerate activityCrystallography X-Ray01 natural sciencesAnalytical ChemistryMiceAscomycotaDrug DiscoveryEndophytesIc50 valuesAnimalsCytotoxicityPharmacology010405 organic chemistryChemistryMouse LymphomaOrganic ChemistryAbsolute configurationNuclear magnetic resonance spectroscopyEndophytic fungus0104 chemical sciences010404 medicinal & biomolecular chemistryComplementary and alternative medicineRhinocladiella similisMolecular MedicineSesquiterpenesJournal of Natural Products
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Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic Fungus, Pestalotiopsis microspora.

2016

Seven new 14-membered macrolides, pestalotioprolides C (2), D-H (4-8), and 7-O-methylnigrosporolide (3), together with four known analogues, pestalotioprolide B (1), seiricuprolide (9), nigrosporolide (10), and 4,7-dihydroxy-13-tetradeca-2,5,8-trienolide (11), were isolated from the mangrove-derived endophytic fungus Pestalotiopsis microspora. Their structures were elucidated by analysis of NMR and MS data and by comparison with literature data. Single-crystal X-ray diffraction analysis was used to confirm the absolute configurations of 1, 2, and 10, while Mosher's method and the TDDFT-ECD approach were applied to determine the absolute configurations of 5 and 6. Compounds 3-6 showed signif…

StereochemistryMolecular ConformationPharmaceutical ScienceAntineoplastic Agents010402 general chemistryCrystallography X-Ray01 natural sciencesAnalytical ChemistryStructure-Activity RelationshipTermészettudományokDrug DiscoveryMicrosporaCytotoxic T cellStructure–activity relationshipHumansCameroonKémiai tudományokCytotoxicityIC50PharmacologyProtein Synthesis InhibitorsbiologyMolecular StructureXylariales010405 organic chemistryOrganic ChemistryPestalotiopsis microsporaFabaceaeEndophytic fungusbiology.organism_classification0104 chemical sciencesAnti-Bacterial AgentsComplementary and alternative medicineCell cultureMolecular MedicineMacrolidesJournal of natural products
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Organoplatinum(II) Complexes Self-Assemble and Recognize AT-Rich Duplex DNA Sequences

2021

The specific recognition of AT-rich DNA sequences opens up the door to promising diagnostic and/or therapeutic strategies against gene-related diseases. Here, we demonstrate that amphiphilic PtII complexes of the type [Pt(dmba)(N∧N)]NO3 (dmba = N,N-dimethylbenzylamine-κN, κC; N∧N = dpq (3), dppz (4), and dppn (5)) recognize AT-rich oligonucleotides over other types of DNA, RNA, and model proteins. The crystal structure of 4 shows the presence of significant π-stacking interactions and a distorted coordination sphere of the d8 PtII atom. Complex 5, containing the largest π-conjugated ligand, forms supramolecular assemblies at high concentrations under aqueous environment. However, its aggreg…

Coordination sphereOrganoplatinum CompoundsStereochemistrySupramolecular chemistryDMBAElectrophoretic Mobility Shift Assay010402 general chemistryCrystallography X-RayLigands01 natural sciencesArticleInorganic Chemistrychemistry.chemical_compoundCoordination ComplexesHumansPhysical and Theoretical ChemistryDNA • light-switch • platinum • pseudo-tetrahedral • antitumor agent • DFTOrganoplatinumGel electrophoresisMolecular Structure010405 organic chemistryChemistryOligonucleotideLigandSpectrum AnalysisStereoisomerismDNAIntercalating Agents0104 chemical sciencesA549 CellsSettore CHIM/03 - Chimica Generale E InorganicaDNA
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Polyketides and nitrogenous metabolites from the endophytic fungus Phomopsis sp. D15a2a

2019

Abstract Three new polyketides, phomopones A−C (1–3), one new cyclic tetrapeptide, 18-hydroxydihydrotentoxin (4), and a new amide, 6-hydroxyenamidin (5) together with a known derivative, enamindin (6) were obtained from the endophytic fungus Phomopsis sp. D15a2a isolated from the plant Alternanthera bettzickiana. The structures of the new compounds were elucidated by 1D, 2D NMR and HRMS data. The absolute configurations of the isolated metabolites were determined either by X-ray crystallography, Marfey’s method or by converting the compounds to Mosher esters.

biologyTetrapeptide010405 organic chemistryStereochemistryOrganic ChemistryEndophytic fungus010402 general chemistrybiology.organism_classification01 natural sciencesBiochemistry0104 chemical scienceschemistry.chemical_compoundchemistryAmideDrug DiscoveryPhomopsis sp.Alternanthera bettzickianaTwo-dimensional nuclear magnetic resonance spectroscopyDerivative (chemistry)Tetrahedron Letters
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CCDC 1998467: Experimental Crystal Structure Determination

2021

Related Article: Ana Zamora, Erin Wachter, María Vera, David K. Heidary, Venancio Rodríguez, Enrique Ortega, Vanesa Fernández-Espín, Christoph Janiak, Edith C. Glazer, Giampaolo Barone, José Ruiz|2021|Inorg.Chem.|60|2178|doi:10.1021/acs.inorgchem.0c02648

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates{2-[(dimethylamino)methyl]phenyl}-(110-phenanthroline)-platinum(ii) nitrate trihydrate
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CCDC 1479852: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters58-dihydroxy-14-methyloxacyclotetradeca-369-trien-2-oneExperimental 3D Coordinates
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CCDC 1862565: Experimental Crystal Structure Determination

2019

Related Article: Ni P. Ariantari, Elena Ancheeva, Chenyin Wang, Attila Mándi, Tim-O. Knedel, Tibor Kurtán, Chaidir Chaidir, Werner E. G. Müller, Matthias U. Kassack, Christoph Janiak, Georgios Daletos, Peter Proksch|2019|J.Nat.Prod.|82|1412|doi:10.1021/acs.jnatprod.8b00723

Space GroupCrystallographyCrystal SystemCrystal Structure2214b-trimethyl-23671314b1516-octahydro-316a-epoxyoxepino[3'2':56]naphtho[12-b]carbazol-4(5bH)-oneCell ParametersExperimental 3D Coordinates
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CCDC 1479853: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters58-dihydroxy-14-methyloxacyclotetradeca-369-trien-2-oneExperimental 3D Coordinates
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CCDC 1968535: Experimental Crystal Structure Determination

2021

Related Article: Ni Putu Ariantari, Marian Frank, Ying Gao, Fabian Stuhldreier, Anna-Lene Kiffe-Delf, Rudolf Hartmann, Simon-Patrick Höfert, Christoph Janiak, Sebastian Wesselborg, Werner E.G. Müller, Rainer Kalscheuer, Zhen Liu, Peter Proksch|2021|Tetrahedron|85|132065|doi:10.1016/j.tet.2021.132065

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters5-hydroxy-4-methoxy-78-dimethyl-78-dihydro-2H5H-pyrano[43-b]pyran-2-one monohydrateExperimental 3D Coordinates
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CCDC 1479850: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

213-dihydroxy-7-methyl-615-dioxabicyclo[12.1.0]pentadeca-311-dien-5-one monohydrateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1479851: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters58-dihydroxy-14-methyloxacyclotetradec-3-en-2-oneExperimental 3D Coordinates
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CCDC 1968536: Experimental Crystal Structure Determination

2021

Related Article: Ni Putu Ariantari, Marian Frank, Ying Gao, Fabian Stuhldreier, Anna-Lene Kiffe-Delf, Rudolf Hartmann, Simon-Patrick Höfert, Christoph Janiak, Sebastian Wesselborg, Werner E.G. Müller, Rainer Kalscheuer, Zhen Liu, Peter Proksch|2021|Tetrahedron|85|132065|doi:10.1016/j.tet.2021.132065

6-(3-hydroxybutan-2-yl)-5-(hydroxymethyl)-4-methoxy-2H-pyran-2-oneSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1869183: Experimental Crystal Structure Determination

2019

Related Article: Shuai Liu, Yuping Zhao, Christian Heering, Christoph Janiak, Werner E. G. Müller, Sergi Hervé Akoné, Zhen Liu, Peter Proksch|2019|J.Nat.Prod.|82|1055 |doi:10.1021/acs.jnatprod.8b00938

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters2-(chloromethyl)-2-hydroxy-6-[2-(hydroxymethyl)-3-methoxy-3-oxoprop-1-en-1-yl]-5-(propan-2-yl)cyclohexane-1-carboxylic acid sesquihydrateExperimental 3D Coordinates
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CCDC 1946592: Experimental Crystal Structure Determination

2020

Related Article: Haiqian Yu, Simon-Patrick Höfert, Mariam Moussa, Christoph Janiak, Werner E.G. Müller, Blessing O. Umeokoli, Haofu Dai, Zhen Liu, Peter Proksch|2019|Tetrahedron Lett.|60|151325|doi:10.1016/j.tetlet.2019.151325

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinatesphomopone A
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CCDC 1481781: Experimental Crystal Structure Determination

2016

Related Article: Hao Wang, Haofu Dai, Christian Heering, Christoph Janiak, Wenhan Lin, Raha S. Orfali, Werner E. G. Müller, Zhen Liu, Peter Proksch|2016|RSC Advances|6|81685|doi:10.1039/C6RA14554J

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersN-(6-bromo-1710-trihydroxy-5-oxo-3-oxatricyclo[4.3.1.024]decan-8-yl)-46-dimethyldodeca-24-dienamide methanol solvateExperimental 3D Coordinates
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CCDC 1515373: Experimental Crystal Structure Determination

2021

Related Article: Ana Zamora, Erin Wachter, María Vera, David K. Heidary, Venancio Rodríguez, Enrique Ortega, Vanesa Fernández-Espín, Christoph Janiak, Edith C. Glazer, Giampaolo Barone, José Ruiz|2021|Inorg.Chem.|60|2178|doi:10.1021/acs.inorgchem.0c02648

Space GroupCrystallographyCrystal SystemCrystal Structure(2-((dimethylamino)methyl)phenyl)-(dipyrido[32-a:2'3'-c]phenazine)-platinum(ii) nitrate dichloromethane n-hexane solvateCell ParametersExperimental 3D Coordinates
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CCDC 1517632: Experimental Crystal Structure Determination

2017

Related Article: Hao Wang, Blessing O. Umeokoli, Peter Eze, Christian Heering, Christoph Janiak, Werner E.G. Müller, Raha S. Orfali, Rudolf Hartmann, Haofu Dai, Wenhan Lin, Zhen Liu, Peter Proksch|2017|Tetrahedron Lett.|58|1702|doi:10.1016/j.tetlet.2017.03.052

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters8-hydroxy-3a911b-trimethyl-9-vinyl-3a455a89101111b11c-decahydro-3H-benzo[c]furo[34-f]chromene-17-dioneExperimental 3D Coordinates
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