[Repellent Activity of Vanillin Derivatives and Monoterpenes to Olive Weevil].

Olive weevils, Pimelocerus (Dyscerus) perforatus Roelofs, utilize olive trees as a host plant. The adult female uses an elongated snout to puncture the trunk and lay one egg a day, resulting in dozens of eggs over its lifetime. The hatched larvae grow by eating the olive trunk. When olive trees die due to feeding damage, olive productivity is seriously impaired. Since there is no effective pesticide for olive weevils so far, the authors aimed to develop a repellent for adult olive weevils from the viewpoint of integrated pest management. We prepared a measurable apparatus for the repellent action against olive weevils and screened chemical substances by using the apparatus. When the repellent activity was measured using vanillin and its derivatives, a clear repellent effect could be confirmed for two types of vanillin derivatives, such as o-vanillin, and 2-hydroxy-4-methoxybenzaldehyde. In addition, when the repellent activity against olive weevils was measured using monoterpenes, four types of acyclic monoterpenes, geraniol, ß-citronellol, citral, and linalool, and three types of monocyclic monoterpenes, (-)-limonene, (+)-limonene, and (-)-menthol, and a bicyclic monoterpene, (1R)-(+)-α-pinene, were found to have dose-dependent repellent activity with statistical significance. In the future, it is expected that the formulation for applying the repellent substances to olive trees and the study of their practicality in olive fields will progress.

IPM712, a vanillin derivative as potential antitumor agents, displays better antitumor activity in colorectal cancers cell lines.

Colorectal cancer (CRC), a major health threat in the world, ranks third in incidence and second in mortality among cancers. Chemotherapy, an important treatment for colorectal cancer, have be limited in the clinic due to the resistance and side effect. Studies have shown that PI3K-related regulatory pathways play a colossal role in colorectal cancer. Therefore, it is a good strategy to find a new drug which works by affecting the PI3K signaling pathway. In this paper, we obtained a new vanillin derivative (IPM712) by modifying the structure of IPM711 and tested its anticancer activity in vitro and toxicity in vivo. Results showed that IPM712 has a better anticancer activity than 5-Fu in HCT116 and SW480 cell lines. Furthermore, IPM712 can inhibit cell proliferation, migration and induce the apoptosis by affecting PI3K-related protein expression. Acute toxicity experiments show that IPM712 has no significant toxicity at therapeutic concentrations. Based on these results, IPM712 is a promising anticancer drug candidate for human colorectal cancer therapy.

Crystal structure of 4-(2-hy-droxy-3-meth-oxy-benzyl-amino)-benzoic acid di-methyl-formamide monosolvate monohydrate.

The title compound, C15H15NO4·C3H7NO·H2O, a secondary amine mol-ecule, is accompanied by one equivalent of water and one equivalent of di-methyl-formamide (DMF) as solvents. The mol-ecule is non-planar, with a Car-yl-CH2-NH-Car-yl torsion angle of -66.3 (3)°. In the crystal, O-H⋯O and N-H⋯O hydrogen-bonding inter-actions between the amine mol-ecules and the two types of solvent mol-ecule result in the formation of a layered structure extending parallel to (010).

A vanillin derivative suppresses the growth of HT29 cells through the Wnt/ß-catenin signaling pathway.

Colorectal cancer (CRC) is a common malignancy and the leading cause of cancer death worldwide. According to previous studies, vanillin possesses pharmacological and anticancer activities. In this work, we have modified the structure of vanillin to obtain a vanillin derivative called 4-(1H-imidazo [4,5-f][1,10]-phenanthrolin-2-yl)-2-methoxyphenol (IPM711), which has improved anticancer activity. The present study is intended to explore the anti-colorectal cancer activity of IPM711 in HT29 and HCT116 cells. The results of this study suggest that IPM711 can inhibit the growth, invasion and migration of HT29 and HCT116 cells. Western blot and molecular docking showed that IPM711 could bind to a Wnt/ß-catenin signaling receptor to inhibit cell growth, invasion and migration in HT29 cells. Based on these results, IPM711 is a promising anticancer drug candidate for human colorectal cancer therapy.

Golgi dispersal in irradiated cells and the protective effect of vanillin derivatives / 军事医学

Objective To determine the Golgi dispersal in radiation damaged cells and the protective effect of vanillin derivatives.Methods Immunofluorescence, cell cycle analysis of flow-cytometry,Western blot,and clone formation were used.Results Immunofluorescence observation showed that the Golgi dispersal caused by 2 Gy 60 Coγ-ray was significantly increased in a dose-dependent manner in the range of 4-10 Gy as was demonstrated by the fact that the Golgi area was significantly increased. When the irradiated cells were treated with the radioprotective agent VND3207, a vanillin derivative,the Golgi dispersal induced by radiation was significantly reduced.The radiation-induced Golgi dispersal was also displayed in a pattern of time-course after irradiation in the HeLa cells, and persisted at least to 36 h post-irradiation. Cell cycle test results indicated that the Golgi dispersal was not associated with the G2/M arrest triggered by radiation-induced DNA damage response.VND3207 could promote cell survival by plate colony formation assay.Conclusion The Golgi dispersal can be caused byγ-ray irradiation in a dose-and time-dependent manner, and VND3207 can provide a good protection against radiation injury associated with inhibited Golgi dispersal.

Protection of vanillin derivative VND3207 on plasmid DNA damage induced by different LET ionizing radiation / 中华放射医学与防护杂志

Objective To evaluate the radioprotective effect of vanillin derivative VND3207 on DNA damage induced by different LET ionizing radiation.Methods The plasmid DNA in liquid was irradiated by 60Co γ-rays, proton or 7Li heavy ion with or without VND3207.The conformation changes of plasmid DNA were assessed by agarose gel electrophoresis and the quantification was done using gel imaging system.Results The DNA damage induced by proton and 7Li heavy ion was much more serious as compared with that by 60Co γ-rays, and the vanillin derivative VND3207 could efficiently decrease the DNA damage induced by all three types of irradiation sources, which was expressed as a significantly reduced ratio of open circular form (OC) of plasmid DNA.The radioprotective effect of VND3207 increased with the increasing of drug concentration.The protective efficiencies of 200 μmol/L VND3207 were 85.3% (t =3.70,P =0.033), 73.3% (t = 10.58, P =0.017)and 80.4% (t =8.57,P =0.008)on DNA damage induction by 50 Gy of γ-rays, proton and 7Li heavy ion, respectively.It seemed that the radioprotection of VND3207 was more effective on DNA damage induced by high LET heavy ion than that by proton.Conclusions VND3207 has a protective effect against the genotoxicity of different LET ionizing radiation, especially for γ-rays and 7 Li heavy ion.

Radiosensitization and relative mechanisms of vanillin derivative BVAN08 on human glioma U-251 cells / 中华放射医学与防护杂志

Objective To provide more convincing evidences and experimental data for exploring vanillin derivative BVAN08,6-bromine-5-hydroxy-4-methoxy-benzaldehyde,as a new anticancer drug,and to investigate the effect on the growth,radiosensitization of human glioma cell line U-251 and the relative mechanism.Methods The effect of BVAN08 on cell proliferation of U-251 and radiosensitivity to 60Co γ-rays (irradiation dose rate 2.3 Gy/min) were analyzed with MTT and colony-forming ability assay.Change in cellular morphology was observed by using light microscope.Change in cell cycle and apoptosis was detected with flow cytometry.The autophagy was observed by using TEM (irradiation dose rate is transmission electron microscope).DNA-PKcs protein level was detected through Western blot analysis.Results BVAN08 exhibited a dose- and time-dependent inhibition on the proliferation of U-251 cells during the concentration range of 10-100 mol/L (t = 1.83-3.07,P ＜ 0.05).IC50 at 48 h and 72 h after administration with BVAN08 were 55.3 and 52.7 mol/L,respectively.Obvious G2/M arrest was induced in U-251 cells after 4 h administration with BVAN08,and reached peak at 12 h.The G2/M population reached 63.3% in U-251 cells after 12 h administration of 60 μmol/L BVAN08 and kept increasing with the time,while both apoptosis and autophagic cell death were induced.The most effective radiosensitization time for BVAN08 treatment was 12 h before irradiation.The enhancement ratio of radiosensitivity was 3.14 for 20 μmol/L of BVAN08 12 h before 2 Gy irradiation.Conclusions BVAN08 can nduce apoptosis as well as autophygic cell death of U-251 cells,and sensitize U-251 cells.The mechanism of its radiosensitizing effect might be associated with the induction of G2/M arrest and inhibition of DNA-PKcs expression.BVAN08 seemed to be a romising radiosensitizing anticancer drug.

Radiological protection effect of vanillin derivative VND3207 against radiation-induced cytogenetic damage in mouse bone marrow cells / 中华放射医学与防护杂志

Objective To study the protection of vanillin derivative VND3207 on the cytogenetic damage of mouse bone marrow cell induced by ionizing radiation.Methods BALB/c mice were randomly divided into five groups:normal control group,2 Gy dose irradiation group,and three groups of 2 Gy irradiaiton with VND3207 protection at doses of 10,50 and 100 mg/kg,respectively.VND3207 was given by intragastric administration once a day for five days.Two hours after the last drug administration,the mice were irradiated with 2 Gy γ-rays.The changes of polychromatophilic erythroblasts micronuclei (MN),chromosome aberration (CA) and mitosis index (MI) of mouse bone marrow cells were observed at 24 and 48 h after irradiation.Results Under the protection of VND3207 at the dosages 10,50,100 mg/kg,the yields of poly-chromatophilic erythroblasts MN and CA of bone marrow cells were significantly decreased(t = 2.36-4.26,P ＜ 0.05),and the marrow cells MI remained much higher level compared with the irradiated mice without drug protection (t = 2.58,2.01,P ＜ 0.05).The radiological protection effect was drug dose-dependent,and the administration of VND3207 at the dosage of 100 mg/kg resulted in reduction by 50% and 65% in the yields of MN and CA,respectively.Conclusions VND3207 had a good protection effect of on γ-ray induced cytogentic damage of mouse bone marrow cells.