0000000000006467
AUTHOR
Christoph Janiak
Anorganische Chemie 2002
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.
Indole Diterpenoids from an Endophytic Penicillium sp.
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…
Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids
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…
Fusaristatins D–F and (7S,8R)-(−)-chlamydospordiol from Fusarium sp. BZCB-CA, an endophyte of Bothriospermum chinense
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…
Experimental and Theoretical Investigations on the Synthesis, Structure, Reactivity, and Bonding of the Stannylene-Iron Complex Bis{{bis(2-tert-butyl-4,5,6-trimethyl-phenyl)}Sn}Fe(η6-toluene)
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…
Secondary metabolites of the lichen-associated fungus Apiospora montagnei
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…
Sesquiterpenoids from the Endophytic Fungus Rhinocladiella similis
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.
Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic Fungus, Pestalotiopsis microspora.
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…
Organoplatinum(II) Complexes Self-Assemble and Recognize AT-Rich Duplex DNA Sequences
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…
Polyketides and nitrogenous metabolites from the endophytic fungus Phomopsis sp. D15a2a
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.
CCDC 1998467: Experimental Crystal Structure Determination
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CCDC 1479852: Experimental Crystal Structure Determination
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CCDC 1862565: Experimental Crystal Structure Determination
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CCDC 1479853: Experimental Crystal Structure Determination
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CCDC 1968535: Experimental Crystal Structure Determination
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CCDC 1479850: Experimental Crystal Structure Determination
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CCDC 1479851: Experimental Crystal Structure Determination
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CCDC 1968536: Experimental Crystal Structure Determination
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CCDC 1869183: Experimental Crystal Structure Determination
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CCDC 1946592: Experimental Crystal Structure Determination
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CCDC 1481781: Experimental Crystal Structure Determination
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CCDC 1515373: Experimental Crystal Structure Determination
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CCDC 1517632: Experimental Crystal Structure Determination
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