A highly efficient enantioselective enamine-catalyzed asymmetric conjugate addition has been developed to directly convert unfunctionalized cyclic α-hydroxyamides into chiral cyclic α-hydroxyamides by reacting with vinyl sulfones, which could be used as versatile azacyclic synthons in the following sequences: (1) as the precursors of cyclic -acyliminium ions to prepare natural productlike chiral azapolycyclic compounds under acidic conditions and (2) to construct chiral cyclic imides bearing unilateral substituents via oxidation reaction-induced formal desymmetrization.
View Article and Find Full Text PDFA Brønsted acid-catalyzed cascade process, involving in situ formation of acyclic tertiary enamides and intramolecular Michael reaction, is developed for the synthesis of functionalized cyclic tertiary enamides. Based on the dual reactivities of the enamide moiety, several reaction sequences were realized by using rationally designed substrates, leading to biologically relevant nitrogen-containing heterocyclic compounds with diverse structural skeletons in a concise and diastereocontrolled manner.
View Article and Find Full Text PDFCycloartenyl ferulate (CF) is abundant in brown rice with multiple biologic functions. It has been reported to possess antitumor activity; however, the related mechanism of action of CF has not been clarified. Herein, we unexpectedly uncover the immunological regulation effects of CF and its molecular mechanism.
View Article and Find Full Text PDFThe roots of have a long history of use in Chinese medicine for the treatment of various medical conditions. Flavonoids from the ethyl acetate extract of have shown anti-inflammatory, anticancer, and antidiabetic properties. The objective of this study was to evaluate the toxicological profile of a flavonoid-rich extract of (SFEA).
View Article and Find Full Text PDFFour new polyprenylated acylphloroglucinol derivatives, hyperwilone A-D (), and two new xanthones, wilsonxanthone A () and wilsonxanthone B (), together with eight known compounds were isolated from the aerial parts of . Their structures were expounded by comprehensive analysis of the 1D and 2D NMR spectra and HRESIMS. The relative configurations and absolute configurations of were determined by NMR calculations and comparing their experimental and computed ECD data.
View Article and Find Full Text PDFDavidone C is a newly discovered flavonoid compound purified from the ethyl acetate-soluble fraction of (Franch.) Skeels. This study explored the anti-tumor activity of davidone C on hepatocellular carcinoma HepG2 and Bel-7402 cells and its mechanism through MTT method, morphological observation, flow cytometry and Western blotting.
View Article and Find Full Text PDFAn unprecedented novel flavanone davidone F () with a seven-membered ring side chain, and a novel flavanonol davidone G (), along with 11 known flavonoids, were isolated from the ethyl acetate fraction of (Franch.) Skeels. Their planar structures were established by UV, IR, HRESIMS, 1D and 2D NMR data.
View Article and Find Full Text PDFThree new cadinane-type sesquiterpenes, eupatorinones (-), along with seven known compounds (), were obtained from the petroleum ether fraction of 95% ethanol extract of Spreng. The structures of these new compounds were determined by NMR, MS, and ECD spectra analysis. The configuration of compound was established by quantum chemical calculations of NMR chemical shifts and ECD spectra, that matched the experimental data.
View Article and Find Full Text PDFBioorg Med Chem Lett
May 2021
Five new α-pyrone derivatives, named penpolonin A-E (1-5), together with two known compounds (6-7) were acquired from the endophytic fungus Penicillium polonicum isolated from the roots of Camptotheca acuminata Decne. Their structures were established by combination of NMR and HRESIMS data and the absolute configurations of 1-5 were determined by NMR calculations and comparison of experimental and calculated ECD data. Compounds 3 and 7 exhibited moderate cytotoxicity against Hep-2, TU212 human laryngeal cancer cells with IC values ranging from 31.
View Article and Find Full Text PDF(Franch.) Skeels is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of , a chemical investigation was thus performed.
View Article and Find Full Text PDFHeadings Ethnopharmacological Relevance: Corilagin (β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose) is a tannin isolated from the traditional ethnopharmacological plant Phmllanthi Fructus, which is widely used in not only traditional Chinese medicine but also tropical and subtropical medicine to ameliorate various diseases.
Aim Of The Study: This study was designed to isolate the potential anti-esophageal cancer (EC) component corilagin from Phmllanthi Fructus and explain its anti-EC mechanism.
Materials And Methods: Corilagin was isolated from Phmllanthi Fructus by extraction and chromatographic procedures, and its anti-esophageal cancer effect was evaluated by in vitro and in vivo experiments.
Five new flavanones, davidones A-E (1-5), one new isoflavonoid, cyclolicoisoflavones A (8), together with seven known compounds were isolated from the petroleum ether and the ethyl acetate fractions of the roots of Sophora davidii (Franch.) Skeels. The structures of new compounds were established by 1D and 2D NMR and MS data.
View Article and Find Full Text PDFHeadings Ethnopharmacological Relevance: Sophora alopecuroides L. is a traditional ethnopharmacological plant, which is widely used in traditional Chinese medicine and Mongolian and Uighur medicine to ameliorate "thirst disease".
Aim Of The Study: This study aimed to investigate the antidiabetic activities and mechanisms of a flavonoid-rich extract from Sophora alopecuroides L.
In our present study, the standard chemicals of triacetin were purified by reverse-phase and normal-phase semi-preparative high-performance liquid chromatography (HPLC), and 1H NMR and 13C NMR were employed to determine the purity and structure of triacetin. Moreover, a simple and rapid HPLC-photodiode array (PDA) method was developed to determine the contents of triacetin in 30 batches from different suppliers. The chromatographic separation was performed on a Phenomenex Gemini-NX C18 column (250 × 4.
View Article and Find Full Text PDFBackground: Type 2 diabetes mellitus is primarily caused by insulin resistance (IR) in insulin-sensitive tissues, including liver, white adipose tissues (WAT), and skeletal muscles. Discovering nutritious foods with antidiabetic effects is of great significance. Numerous published reports indicated that protein kinase B (Akt) and glucose transporter 4 (GLUT4) play crucial roles in ameliorating IR and diabetic symptoms.
View Article and Find Full Text PDFSelaginella moellendorffii Hieron. (SM), a perennial evergreen plant, has been used in the treatment of acute infectious hepatitis, thoracic and hypochondriac lumbar contusions, systemic oedema and thrombocytopaenia. However, the role of a biflavonoid-rich extract from SM (SM-BFRE) in anti-larynx cancer has rarely been reported.
View Article and Find Full Text PDFTo discover novel structural compounds which are producted by endophytic fungi, a primary chemical profiling of Decne derived endophytic fungus had been taken. Two new compounds β-lactone polonicin A () and enoic acid polonicin B () together with seven known compounds - were isolated from obtained from . The structures of the new compounds and were identified by modern spectrum technology including detailed 1D, 2D NMR and MS data analyses.
View Article and Find Full Text PDF