Structural studies of 2-(3′,4′-dihydroxyphenyl)-7-β-D-glucopyranos-1-O-yl-8-hydroxychroman-4-one in the liquid and solid states by means of 2D NMR spectroscopy and DFT calculations

Olejniczak, Sebastian; Ganicz, K.; Tomczykowa, Monika; Gudej, Jan; Potrzebowski, Marek J.

doi:10.1039/b202414b

Cited by 18 publications

(9 citation statements)

References 25 publications

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“…A decrease of δ 11 element and an increase of δ 22 can be observed, which is characteristic of the formation of hydrogen bonds, as observed for peptides [34] and flavonoids. [23] Significant differences between the experimental and theoretical values are also observed for the δ 33 element, which may reflect the π -π stacking interactions. The correlation between δ 33 and σ 33 is better for baicalin than for baicalein; suggesting stronger 'sandwich-like' interactions in baicalein, which has no sugar moiety.…”

Section: And B With 'Clockwise' Orientation Of Oh Groups (Illustrated Inmentioning

confidence: 86%

Solid‐state NMR studies and DFT calculations of flavonoids: baicalein, baicalin and wogonoside

Wolniak¹,

Oszmiański²,

Wawer³

2007

Magnetic Reson in Chemistry

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Three flavonoids of pharmaceutical importance-baicalein, baicalin, and wogonoside-were isolated from a Chinese medicinal plant Scutellaria baicalensis Georgi and studied by 13C NMR in solution and solid state. Two-dimensional (2D) NMR spectroscopy in the liquid phase and dipolar dephasing (DD) experiments in magic-angle spinning (MAS) spectra enabled the assignment of 13C resonances. The cross-polarization (CP) time constants T(CH) and relaxation times T(H) (1rho) were obtained from the variable-contact time experiments. The principal elements of the 13C chemical shift tensor were determined in the spectra recorded under slow sample spinning (2 kHz) using phase-adjusted spinning sideband (PASS)-2D NMR technique, and were verified by density functional theory gauge-independent atomic orbital (DFT GIAO) calculations of shielding constants. Analysis of the 13C delta(ii) and comparison with shielding parameters calculated for different conformers of compounds 1-3 enabled the selection of the most reliable geometry in the solid phase. In all three compounds, an intramolecular hydrogen bond C5--OH...=C4 is formed; the existence of baicalein and baicalin with 'anticlockwise' orientation of OH groups is more probable.

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Section: And B With 'Clockwise' Orientation Of Oh Groups (Illustrated Inmentioning

confidence: 86%

Solid‐state NMR studies and DFT calculations of flavonoids: baicalein, baicalin and wogonoside

Wolniak¹,

Oszmiański²,

Wawer³

2007

Magnetic Reson in Chemistry

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“…The methylene chloride extract of B. tripartita has demonstrated to have high activity in the inhibition of cancer L1210 (mouse leukemia) cells and against thrombin [7]. Extensive phytochemical studies on B. tripartita have shown the presence of flavonoids [8][9][10][11], coumarins [12], essential oil [13], polysaccharides, carotenoids, -lactones, amines and mineral elements [10,14]. In the petroleum extract of the herb of burmarigold, triterpenes, unsaturated aliphatic hydrocarbons, esters of fatty acids and sterols, with dominating stigmasterol, were identified.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and antifungal activities of the extracts and essential oils of Bidens tripartita.

Tomczykowa

Jakoniuk²,

Tryniszewska³

2008

Folia Histochem Cytobiol.

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Essential oils and plant extracts preparation. The essential oil (BTHO) was hydrodistilled (3 h) from the freshly picked flowering aerial parts of the herb (500 g) using a Deryng-type apparatus. The oil (BTFO) was obtained also from dried flower heads (210 g) using the same distillation method [13].Dried and powdered B. tripartita flowers (BF) and herb (BH) were subjected to several extraction procedures: water, FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 46, No. 3, 2008 pp. 389-393 Antimicrobial and antifungal activities of the extracts and essential oils of Bidens tripartita Abstract: The aim of this study was to determine the antibacterial and antifungal properties of the extracts, subextracts and essential oils of Bidens tripartita flowers and herbs. In the study, twelve extracts and two essential oils were investigated for activity against different Gram-positive Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, Gram-negative bacteria Escherichia coli, E. coli (β-laktamase+), Klebsiella pneumoniae (ESBL+), Pseudomonas aeruginosa and some fungal organisms Candida albicans, C. parapsilosis, Aspergillus fumigatus, A. terreus using a broth microdilution and disc diffusion methods. The results obtained indicate antimicrobial activity of the tested extracts (except butanolic extracts), which however did not inhibit the growth of fungi used in this study. Bacteriostatic effect of both essential oils is insignificant, but they have strong antifungal activity. These results support the use of B. tripartita to treat a microbial infections and it is indicated as an antimicrobial and antifungal agent, which may act as pharmaceuticals and preservatives.

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“…Detailed explanation of the PASS-2D pulse sequence, its performance, a Mathematica routine to generate a set of PASS solutions, and data processing can be found elsewhere. [28] Although to date there has been no report showing application of the sequence to study of polymorphs, this approach has great potential for examination of complex mixtures. [28] Although to date there has been no report showing application of the sequence to study of polymorphs, this approach has great potential for examination of complex mixtures.…”

Section: Polymorphism and Pseudo-polymorphism ؊ Challenges For Organimentioning

confidence: 99%

What High‐Resolution Solid‐State NMR Spectroscopy Can Offer to Organic Chemists

Potrzebowski

2003

ChemInform

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Structural studies of 2-(3′,4′-dihydroxyphenyl)-7-β-D-glucopyranos-1-O-yl-8-hydroxychroman-4-one in the liquid and solid states by means of 2D NMR spectroscopy and DFT calculations

Cited by 18 publications

References 25 publications

Solid‐state NMR studies and DFT calculations of flavonoids: baicalein, baicalin and wogonoside

Solid‐state NMR studies and DFT calculations of flavonoids: baicalein, baicalin and wogonoside

Antimicrobial and antifungal activities of the extracts and essential oils of Bidens tripartita.

What High‐Resolution Solid‐State NMR Spectroscopy Can Offer to Organic Chemists

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