On the molecular and electronic structure of matrine-type alkaloids

@article{Galasso2006OnTM,
  title={On the molecular and electronic structure of matrine-type alkaloids},
  author={Vinicio Galasso and Fioretta Asaro and Federico Berti and Barbara Pergolese and Branka Kova{\vc} and Fabio Pichierri},
  journal={Chemical Physics},
  year={2006},
  volume={330},
  pages={457-468}
}
Abstract A systematic study of the molecular and electronic structure of the eight possible members in the trans -matrine series and of two dehydro-derivatives, sophocarpine and sophoramine, has been performed. According to density functional theory (DFT) calculations these alkaloids exhibit a variety of form and junction of the four six-membered rings and all but sophocarpine have a strong preference for one conformation. Sophocarpine is predicted to have a marked conformational flexibility at… Expand
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References

SHOWING 1-10 OF 52 REFERENCES
On the structure and spectroscopic properties of sparteine and its diastereoisomers
Abstract The equilibrium structures of the lupine alkaloid sparteine, its diastereoisomers (α-sparteine and β-sparteine), and two related tricyclic diamines were investigated with the densityExpand
Structural and spectroscopic characterization of oxo-sparteines
Abstract The equilibrium structures of the 11 possible oxo-derivatives of sparteine were investigated with the density functional theory, using the B3LYP functional. The conformational preferences ofExpand
Stereochemistry of Ruthenium Bis-chelate Disulfoxide Complexes. A Molecular Mechanics Investigation.
TLDR
A topological analysis of bis-chelate disulfoxide metal complexes and the results of molecular mechanics calculations on dichloro-1,2-bis(methylsulfinyl)ethane Ru(II) complexes are presented to study the influence of the nonbonded atom interactions arising from linkage and cis-trans isomerism combined with different arrangements of the sulfur chiral centers on the strain energy of the compounds. Expand
Distortion of the amide bond in amides and lactams. Photoelectron-spectrum and electronic structure of 3,5,7-trimethyl-1-azaadamantan-2-one, the most twisted amide
We report the He(I) photoelectron spectrum of 3,5,7-trimethyl-1-azaadamantan-2-one (20). Ionization potentials have been assigned to molecular orbitals on the basis of quantum chemical calculations.Expand
Determination of quinolizidine alkaloids in Sophora tonkinensis by HPCE.
TLDR
The alkaloid constituents of authentic shan-dou-gen gave a specific HPCE electropherogram that could be used to distinguish the drug from potential substitutes and the content of oxymatrine and the total content of the seven quinolizidine alkaloids could be use as quantitative markers in order to assess the quality of S. tonkinensis. Expand
Studies on Lupin Alkaloids. VI. Isolation and Structure of (+)-Isomatrine
A new stereoisomer of matrine was isolated from "Ku-Shen, " dry roots of Sophora flavescens, and named (+)-isomatrine. Epimerization of this compound into (+)-matrine (I) demostrated its flamework.Expand
Electronic structure and conformational properties of the amide linkage: Part 2. Conformational analysis of the amide group by photoelectron spectroscopy
He—I photoelectron spectra of secondary and tertiary lactams have been measured and interpreted. The sequence of the first two ionization potentials, which are decisive for conformational analysis,Expand
Manifestation of stereoelectronic effects on the calculated carbon-hydrogen bond lengths and one bond (1)J(C-H) NMR coupling constants in cyclohexane, six-membered heterocycles, and cyclohexanone derivatives.
TLDR
Calculated r(C-H) bond lengths and (1)J(H) coupling constants for C-H bonds participating in more than one hyperconjugative interaction show additivity of the effects. Expand
1H and13C chemical shift assignments and stereochemistry of matrine and oxymatrine
Matrine and oxymatrine were extracted fromSophora flavescens, and their1H and13C nuclear magnetic resonances (NMR) were unambiguously assigned by a combination of different two-dimensional 2-D1H-13CExpand
Stereochemical analysis and complete 1H/13C NMR chemical shift assignments of matrine. Application of NOE and two‐dimensional NMR techniques
The stereochemical and structural analysis of matrine was carried out using nuclear magnetic resonance spectroscopy. Several methods, including 13C1H two‐dimensional shift correlation spectroscopy,Expand
...
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2
3
4
5
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