Identification of metabolites of rupestonic acid in rat urine by liquid chromatography combined with electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry

Rupestonic acid, a potential anti‐influenza agent, is an important and characteristic compound in Artemisia rupestris L., a well‐known traditional Uighur medicine for the treatment of colds. In the present study, high‐performance liquid chromatography combined with electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry was used to detect and identify the metabolites in rat urine after oral administration of rupestonic acid. A total of 10 metabolites were identified or partially characterized. The structure elucidations of the metabolites were performed by comparing the changes in accurate molecular masses and fragment ions with those of the parent compound. The results showed that the main metabolites of rupestonic acid in rat urine were formed by oxidation, hydrogenation and glucuronidation. A metabolism pathway was proposed for the first time based on the characterized structures. This metabolism study can provide essential information for drug discovery, design and clinical application of rupestonic acid. Copyright © 2014 John Wiley & Sons, Ltd.     

Mild and Efficient Procedure for Michael Addition of N-Heterocycles to α,β-Unsaturated Compounds Using Anhydrous K3PO4 as Catalyst

Imidazole, 1,2,4-triazole, indole, and benzotriazole undergo conjugate additions with α, β-unsaturated carbonyl compounds in the presence of anhydrous potassium phosphate at ambient temperature to afford the corresponding Michael adducts in excellent yields.     

New Guaipyridine Sesquiterpene Alkaloids from Artemisia rupestris L.

Three new guaipyridine sesquiterpene alkaloids, rupestine A, B, C ( 1 – 3 , resp.), and the new nor‐sesquiterpne alkaloid rupestine D ( 4 ) were obtained from the flowers of Artemisia rupestris L. Their structures were elucidated on the basis of sepectroscopic data and by comparison with those of the related compounds reported in the literature. In addition, the absolute configurations of 2 and 4 were determined by single‐crystal X‐ray diffraction analyses.     

Vernodalidimers A and B, novel orthoester elemanolide dimers from seeds of Vernonia anthelmintica

Two novel elemanolide dimers, vernodalidimers A (1) and B (2), possessing a rare tricyclic ortho ester moiety, were isolated from the seeds of Vernonia anthelmintica. Their structures were elucidated by 1D and 2D NMR data and CD spectra. Vernodalidimers A (1) and B (2) exhibited potent cell growth inhibitory activity against HL-60 cells (IC₅₀ 0.72 and 0.47 μM, respectively).     

Novel Designs for Centrifugal Countercurrent chromatography: V. Comparative Studies on Performance of Various Column Configurations

The conventional toroidal coil in centrifugal countercurrent chromatography has a low level of stationary phase retention, since a half of each helical turn is entirely occupied by the mobile phase. In order to cope with this problem, several new column designs including zigzag, saw-tooth and figure-8 patterns have been introduced and their performance was compared in terms of retention of the stationary phase (Sf), peak resolution (Rs), theoretical plate number (N) and column pressures. Overall results of experiments indicate that the figure-8 column yields the highest Rs when the lower phase is used as the mobile phase. Since the column pressure of all these new columns are much lower than that in the traditional toroidal coil column, the separation efficiency can be improved using a long separation column without a risk of column damage by high back pressure.     

Triterpenoids and phenolics from the fruiting bodies of Inonotus hispidus and their activations of melanogenesis and tyrosinase

Two new 24-methyl lanostane triterpenoids,hispindic acids A and B(1 and 2),and a new phenolic compound,hispinine(7),along with nine known compounds(3-6,and 8-12),were isolated from the fruiting bodies of Inonotus hispidus.Their structures were elucidated based on the extensive analysis of spectroscopic data(NMR and HRMS).Hispindic acid A(1) possesses an unusual formyl group at C-30.Compounds 1,3-4,and 8 showed stronger activate abilities of melanogenesis and tyrosinase in B16 melanoma cells than those of positive control,8-methoxypsoralen,at 50 μmol/L