Corylifol A

Carbohydr Res. 2017 Jun 29;446-447:61-67.

Enzymatic synthesis of novel corylifol A glucosides via a UDP-glycosyltransferase.[Pubmed: 28528234 ]

Corylifol A, a member of the isoflavone subclass of isoflavonoids, has long been considered to have various biological activities.
METHODS AND RESULTS:
Here, we sought to synthesize Corylifol A glucosides by the in vitro glucosylation reaction using the UDP-glycosyltransferase YjiC from Bacillus licheniformis DSM 13, and obtained two novel glucosides: Corylifol A-4',7-di-O-beta-d-glucopyranoside (1) and Corylifol A-4'-O-beta-d-glucopyranoside (2). To improve the yield of the products, the reaction time, concentration of UDP-glucose, and pH of the buffer were optimized. The Michaelis constant (Km) was calculated to be 2.88 mM, and the maximal velocity (Vmax) was calculated to be 77.32 nmol/min/mg for UDP-glycosyltransferase. Meanwhile, the water-solubility of compounds 1 and 2 was approximately 27.03 and 15.13 times higher, respectively, than that of their parent compound Corylifol A. Additionally, the Corylifol A glycosylated products exhibited the highest stability at pH 9.6 and better temperature stability than Corylifol A at 40, 60, 80 and 100 °C. In addition, cytotoxicity activity assays against three human tumor cell lines, only Corylifol A showed moderate anti-proliferative activity.
CONCLUSIONS:
Overall, this work demonstrates that glycosylation can enhance the water solubility and stability of promising compounds, with potential for further development and application.

J Asian Nat Prod Res. 2013;15(6):624-30.

Cytotoxic constituents from Psoralea corylifolia.[Pubmed: 23659434 ]

Bioassay directed isolation of the EtOAc extract from a traditional Chinese medicine Psoralea corylifolia resulted in the purification of two isoflavonoids, corylifols D (1) and E (2), along with four known ones.
METHODS AND RESULTS:
The structures of 1 and 2 were determined by extensive 1D and 2D NMR and MS data analyses. When tested against HepG2 and Hep3B hepatocellular carcinoma cell lines, Corylifol A (4) displayed IC50 values of 4.6 and 13.5 μg/ml, respectively.

Planta Med. 2012 Jun;78(9):903-6.

Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation.[Pubmed: 22573369 ]

Inhibiting interleukin-6 (IL-6) has been postulated as an effective therapy in the pathogenesis of several inflammatory diseases.
METHODS AND RESULTS:
In this study, seven flavonoids were isolated from the methanol extracts of Psoralea corylifolia by bioactivity-guided fractionation. The structures of bakuchiol (1), bavachinin (2), neobavaisoflavone (3), Corylifol A (4), corylin (5), isobavachalcon (6), and bavachin (7) were determined by spectroscopic analysis (1H-, 13C- NMR and MS). We demonstrated that compounds 1-7 showed an inhibitory effect on IL-6-induced STAT3 promoter activity in Hep3B cells with IC50 values of 4.57 ± 0.45, 3.02 ± 0.53, 2.77 ± 0.02, 0.81 ± 0.15, 1.37 ± 0.45, 2.45 ± 0.13, and 4.89 ± 0.05 μΜ, respectively. These compounds also inhibited STAT3 phosphorylation induced by IL-6 in Hep3B cells.
CONCLUSIONS:
Overall, several flavonoids from P. corylifolia might be useful remedies for treating inflammatory diseases by inhibiting IL-6-induced STAT3 activation and phosphorylation.

Fitoterapia. 2015 Mar;101:99-106.

Fructus Psoraleae contains natural compounds with potent inhibitory effects towards human carboxylesterase 2.[Pubmed: 25596095 ]

Fructus Psoraleae (FP) is an edible Chinese herbal which is widely used in Asia for the treatment of various diseases including asthma, diarrhea, and osteoporosis.
METHODS AND RESULTS:
This study aimed to investigate the inhibitory effects of the crude ethanol extract from FP on human carboxylesterase 2 (hCE2), as well as to identity and characterize the naturally occurring inhibitors of hCE2 in FP. Our results demonstrated that the ethanol extract of FP displayed potent inhibitory effects towards hCE2, while five major bioactive constitutes in FP were efficiently identified by LC-DAD-ESI-MS/MS, with the aid of LC-based activity profiling. The identified bioactive compounds including neobavaisoflavone, isobavachalcone, bavachinin, Corylifol A and bakuchiol were found to be naturally occurring potent inhibitors of hCE2, with low Ki values ranging from 0.62μM to 3.89μM.
CONCLUSIONS:
This is the first report of the chemical constitutes in FP as potent inhibitors of hCE2.

J Sep Sci. 2017 Sep;40(17):3522-3534.

Efficient discovery and capture of new neuronal nitric oxide synthase-postsynaptic density protein-95 uncouplers from herbal medicines using magnetic molecularly imprinted polymers as artificial antibodies.[Pubmed: 28704580 ]

In the scope of stroke treatment, new neuronal nitric oxide synthase-postsynaptic density protein-95 uncouplers from herbal medicines were discovered and captured.
METHODS AND RESULTS:
To do so, highly selective magnetic molecularly imprinted polymers with a core-shell structure were prepared as artificial antibodies. According to the results of computational simulations, we designed and synthesized various polymers with varying amounts and types of template, functional monomer, cross-linker, and solvent. Characterization and performance tests revealed that the most appropriate artificial antibodies showed uniform spherical morphologies, large adsorption capacities, fast-binding kinetics, high selectivity, and quick separation. These artificial antibodies were then used as sorbents for dispersive magnetic solid-phase extraction coupled with high-performance liquid chromatography and mass spectrometry to capture and identify structural analogs to ZL006 from extracts of Scutellariae radix, Psoraleae fructus, and Trifolium pratense. Furthermore, according to the neuroprotective effect and coimmunoprecipitation test, Baicalein, Neobavaisoflavone, Corylifol A, and Biochanin A can be the potential uncouplers of neuronal nitric oxide synthase-postsynaptic density protein-95.
CONCLUSIONS:
Therefore, this present study contributes valuable information for the discovery of neuronal nitric oxide synthase-postsynaptic density protein-95 uncouplers from herbal medicines.