Search results for "magnetic resonance spectroscopy"

Ancistrolikokine I and further 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activit…

2018

Abstract The Congolese liana Ancistrocladus likoko (Ancistrocladaceae) produces naphthylisoquinoline alkaloids that are, chemotaxonomically remarkable, all based on the same coupling type, with the biaryl axis located between C-5 and C-8′. About 20 alkaloids, belonging to the subclass of 5,8′-linked naphthylisoquinolines, have so far been discovered in this plant species. Here, we report on the isolation and structure elucidation of six further such 5,8′-coupled monomeric alkaloids, named ancistrolikokines I (9), C3 (10), F2 (11), J (12), J2 (13), and J3 (14). They were identified in the twigs of A. likoko, along with the two new atropo-diastereomeric dimers michellamines A8 (15a) and B8 (1…

Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8'- and 7,1'-linked metabolites from …

2016

From the twigs and stems of the Chinese liana Ancistrocladus tectorius (Ancistrocladaceae), two new 5,8'-coupled naphthylisoquinolines, ancistectorine D (5) and its 6-O-demethyl derivative 6, were isolated, along with two new 7,1'-linked alkaloids, 6-O-methylancistectorine B1 (7) and ancistectorine B2 (8). Two further compounds, ancistroealaine A (4) and 6-O-demethyl-8-O-methyl-7-epi-ancistrobrevine D (10), already known from related Asian and African Ancistrocladus species, were discovered for the first time in A. tectorius. The structure elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (circular di…

Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches

2018

Abstract Two new cryptic 3,4-dihydronaphthalen-(2H)-1-one (1-tetralone) derivatives, aspvanicin A (1) and its epimer aspvanicin B (2), as well as several known cryptic metabolites (3–8), were obtained from the ethyl acetate extract of the co-culture of the endophytic fungus Aspergillus versicolor KU258497 with the bacterium Bacillus subtilis 168 trpC2 on solid rice medium. When A. versicolor was cultured axenically in liquid Wickerham medium supplemented with 3.5% DMSO, an additional three known secondary metabolites (9–11) were isolated that were lacking when the fungus was fermented on rice medium. The structures of the new compounds were elucidated using one- and two-dimensional NMR spec…

Cytotoxic secondary metabolites from the endophytic fungus Aspergillus versicolor KU258497

2018

Abstract Two new isocoumarin dimers (1 and 2) and one new dihydroquinolone derivative (3) were isolated from Aspergillus versicolor, an endophyte derived from leaves of the Egyptian water hyacinth Eichhornia crassipes (Pontederiaceae), together with ten other known metabolites. Chemical structures of the isolated metabolites were determined based on HRESIMS, extensive 1D and 2D NMR spectroscopy. The relative and absolute configurations of the new natural products were established by ROESY and electronic circular dichroism (ECD) spectroscopy, respectively. The axial chirality of the isocoumarin 7,7′-homodimers (1 and 2) was deduced by TDDFT-ECD calculations. All isolated compounds were asses…

Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferm

2015

Four new tetrahydroanthraquinone derivatives, namely, dihydroaltersolanol B (1), dihydroaltersolanol C (2), and the atropisomers acetylalterporriol D (3) and acetylalterporriol E (4), were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus growing in Egypt. The structures of the new compounds were unambiguously elucidated on the basis of one- and two-dimensional NMR spectroscopy, as well as by high-resolution mass spectrometry and electronic circular dichroism (ECD) spectroscopy. In addition, seven known anthraquinone derivatives 5–11 were isolated and identified on the basis of their spectral characteristics and by comparison with literature…

New Austalides from the Sponge-Associated Fungus Aspergillus sp.

2011

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded five new meroterpenoid metabolites, austalides M–Q (1–5), together with nine known compounds (6–13). The structures of the new compounds were unambiguously elucidated on the basis of extensive 1D and 2D NMR methods and by mass spectral analysis. Furthermore, the absolute configurations of 1 and 4 were determined by time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations, allowing the assignment of the absolute configuration of analogous compounds 2, 3, and 5. The calculations revealed that the conform…

2019

A unique series of six biaryl natural products displaying four different coupling types (5,1′, 7,1′, 7,8′, and 5,8′) were isolated from the roots of the West African liana Ancistrocladus abbreviatus (Ancistrocladaceae). Although at first sight structurally diverse, these secondary metabolites all have in common that they belong to the rare group of naphthylisoquinoline alkaloids with a fully dehydrogenated isoquinoline portion. Among the African Ancistrocladus species, A. abbreviatus is so far only the second one that was found to produce compounds with such a molecular entity. Here, we report on four new representatives, named ancistrobreveines A–D (12–14, and 6). They were identified alon…

The metabolic profile of lemon juice by proton HR-MAS NMR: the case of the PGI Interdonato Lemon of Messina

2015

We have studied by means of High Resolution Magic Angle Spinning Nuclear Magnetic Resonance (HR-MAS NMR) the metabolic profile of the famous Sicilian lemon known as 'Interdonato Lemon of Messina PGI'. The PGI Interdonato Lemon of Messina possesses high organoleptic and healthy properties and is recognised as one of the most nutrient fruits. In particular, some of its constituents are actively studied for their chemo-preventive and therapeutic properties. In this paper, we have determined by means of HR-MAS NMR spectroscopy the molar concentration of the main metabolites constituent the juice of PGI Interdonato Lemon of Messina in comparison with that of the not-PGI Interdonato Lemon of Turk…

Unveiling anion-induced folding in tripodal imidazolium receptors by ion-mobility mass spectrometry.

2021

The anion-induced folding of tripodal imidazolium receptors has been investigated by NMR spectroscopy, electrospray ionization ion mobility mass spectrometry and DFT calculations. Such folding can be switched by anion release upon collision induced dissociation.

Rotational diffusion of colloid spheres in concentrated suspensions studied by deuteron NMR

1997

We present a study of the application of deuteron-nuclear magnetic resonance spectroscopy (NMR) to the investigation of the rotational diffusion of spherical colloidal particles. We performed NMR pulse experiments on colloidal suspensions of polystyrene latex spheres in water-glycerol mixtures in a wide range of particle volume fractions \ensuremath{\varphi} from the dilute suspension up to \ensuremath{\varphi}=0.504. We have analyzed the stimulated echo NMR signal in the time domain. The full shape of the orientational correlation function deviates from an exponential behavior in the whole \ensuremath{\varphi} range examined. We evaluate the rotational diffusion coefficient and calculate i…