Diterpenoids from Euphorbia helioscopia and their enhancement of NK cell-mediated killing of NSCLC cells.

Fourteen previously undescribed diterpenoids, including an unusual diterpenoid (1) with a 9,10-seco-jatrophane skeleton, ten jatrophane-type diterpenoids (2-11), two lathyrane-type diterpenoids (12, 13), and an abietane-type diterpenoid (14), together with thirty-six known ones (15-50), were isolated from the whole plants of Euphorbia helioscopia L. The structures of the new isolates were characterized by spectroscopic methods, single-crystal X-ray diffraction analysis, and computational prediction of ECD and chemical shifts. Thirty-nine abundant diterpenoids were evaluated for their enhancement of NK cell-mediated killing of NSCLC cells. As a result, compounds 24, 33, and 41 were found to significantly enhance the killing activity of NK cells towards H1299-luci cells and A549-luci cells at the concentration of 2.5 µM.

Protective Effects of 28-O-Caffeoyl Betulin (B-CA) on the Cerebral Cortex of Ischemic Rats Revealed by a NMR-Based Metabolomics Analysis.

28-O-caffeoyl betulin (B-CA) has been demonstrated to reduce the cerebral infarct volume caused by transient middle cerebral artery occlusion (MCAO) injury. B-CA is a novel derivative of naturally occurring caffeoyl triterpene with little information associated with its pharmacological target(s). To date no data is available regarding the effect of B-CA on brain metabolism. In the present study, a 1H-NMR-based metabolomics approach was applied to investigate the therapeutic effects of B-CA on brain metabolism following MCAO in rats. Global metabolic profiles of the cortex in acute period (9 h after focal ischemia onset) after MCAO were compared between the groups (sham; MCAO + vehicle; MCAO + B-CA). MCAO induced several changes in the ipsilateral cortex of ischemic rats, which consequently led to the neuronal damage featured with the downregulation of NAA, including energy metabolism dysfunctions, oxidative stress, and neurotransmitter metabolism. Treatment with B-CA showed statistically significant rescue effects on the ischemic cortex of MCAO rats. Specifically, treatment with B-CA ameliorated the energy metabolism dysfunctions (back-regulating the levels of succinate, lactate, BCAAs, and carnitine), oxidative stress (upregulating the level of glutathione), and neurotransmitter metabolism disturbances (back-regulating the levels of γ-aminobutyric acid and acetylcholine) associated with the progression of ischemic stroke. With the administration of B-CA, the levels of three phospholipid related metabolites (O-phosphocholine, O-phosphoethanolamine, sn-glycero-3-phosphocholine) and NAA improved significantly. Overall, our findings suggest that treatment with B-CA may provide neuroprotection by augmenting the metabolic changes observed in the cortex following MCAO in rats.

Minor immunosuppressive spiroorthoester group-containing pregnane glycosides from the root barks of Periploca sepium.

LC-MS guided chemical investigation of the periploside-rich extract of the root barks of Periploca sepium afforded six new minor pregnane glycosides, named periplosides A1-A6 (1-6). Their structures were characterized on the basis of extensive spectroscopic analysis. Compounds 1-6 were evaluated for their inhibitory activities against the proliferation of T and B lymphocytes in vitro, among them, compound 5 exhibited significant inhibitory activities and the most favorite selective index (SI) values against the proliferation of T lymphocyte (IC50 = 0.30 µM, SI = 176) and B lymphocyte (IC50 = 0.55 µM, SI = 97).

Effects of wheat protein on hot-extrusion 3D-printing performance and the release behaviours of caffeic acid-loaded wheat starch.

In this study, the effects of wheat protein (WP) on the hot-extrusion 3D-printing (HE-3DP) performance of wheat starch (WS) gels, as well as effects of such gels on the encapsulation of caffeic acid, were investigated for the first time. The HE-3DP results show that the addition of WP can reduce print-line width and improve printing accuracy and fidelity, and the best printing results were achieved when using gels with 10 % WP. The rheological results show that WP reduced the gels' linear viscoelastic region (LVR), yield stress (τy), flow stress (τf) and consistency factor (K) but increased their structural recovery rate, which facilitated smooth extrusion during 3D printing and, thus, improved printing accuracy. The analysis of X-ray diffraction and small-angle X-ray scattering indicates that adding WP to WS could increase the mass fractal dimension and lead to denser gel network structures. The results regarding release kinetics demonstrate that the maximum release of caffeic acid from gels decreased by 28 % with the addition of WP, indicating slow-release behaviour. This study provided valuable information about processing wheat products via 3D printing.

Composite formation of whey protein isolate and OSA starch for fabricating high internal phase emulsion: A comparative study at different pH and their application in biscuits.

The composites formed by whey protein isolate (WPI) and octenyl succinate anhydride (OSA)-modified starch were characterized with a focus on the effect of pH, and their potential in fabricating high internal phase emulsions (HIPEs) as fat substitutes was evaluated. The particles obtained at pH 3.0, 6.0, 7.0, and 8.0 presented a nanosized distribution (122.04 ± 0.84 nm-163.24 ± 4.12 nm) while those prepared at pH 4.0 and 5.0 were remarkably larger. Results from the shielding agent reaction and Fourier transform infrared spectroscopy (FT-IR) showed that the interaction between WPI and OSA starch was mainly hydrophobic at pH 3.0-5.0, while there was a strong electrostatic repulsion at pH 6.0-8.0. A quartz crystal microbalance with dissipation (QCM-D) study showed that remarkably higher ΔD and lower Δf/n were observed at pH 3.0-5.0 after successive deposition of WPI and OSA starch, whereas slight changes were noted for those made at higher pH values. The WPI-OSA starch (W-O) composite-based HIPEs made at pH 3.0 and 6.0-8.0 were physically stable after long-term storage, thermal treatment, or centrifugation. Incorporation of HIPE into the biscuit formula yielded products with a desirable sensory quality.

Dihydro-ß-agarofuran-type sesquiterpenoids from the seeds of Celastrus virens with lifespan-extending effect on the nematode Caenorhabditis elegans.

Twelve dihydro-ß-agarofuran-type sesquiterpenoids, including five new ones (1-5), were purified from the seeds of Celastrus virens (Wang et Tang) C. Y. Chent et T. C. Kao. Their chemical structures were characterized via comprehensive spectroscopic analysis, single-crystal X-ray diffraction analysis, and computational prediction of ECD, as well as comparison of observed and reported NMR spectral data. Among the isolates, nine abundant dihydro-ß-agarofuran-type sesquiterpenoids were evaluated for their lifespan-extending activity using the nematode Caenorhabditis elegans model. As a result, compounds 1, 2, 5, 6, 8, and 9 (50 µM) significantly extended the mean survival time of C. elegans, respectively, compared with the blank control group (p < 0.05). Further Quantitative RT-PCR showed that the prolonging of lifespan mediated by compounds 1, 6, 8, and 9 were dependent on the transcription factors skn-1 and hsf-1.

Diterpenoids from the seeds of Euphorbia lathyris and their effects on microglial nitric oxide production.

Four new lathyrane-type diterpenoids (1-4) and a novel macrocyclic diterpenoid (5) featuring a 5/7/7/4-fused ring system, together with seventeen known ones (6-22), were isolated from the seeds of Euphorbia lathyris. Their structures were elucidated by extensive spectroscopic analyses and single crystal X-ray crystallography. These isolates were evaluated for their inhibition against nitric oxide (NO) production induced by lipopolysaccharide (LPS) in BV-2 microglial cells. As a result, the inhibitory rates of compounds 1, 3, 4, 6, 7, 9-11, 13-15, 20, and 21 on NO production were more than 40% with the cell viability more than 80% at their effective concentrations. In addition, compounds 6 and 11 markedly reduced the mRNA levels of pro-inflammatory cytokines IL-6 and IL-1ß in LPS-stimulated BV-2 cells.