Nitration of furfural to give 5-nitrofurfural diacetate (NFD). By the condensation of NFD with 2-butanone (or acethylacetone), two cetone a, b-ethylenic deriva-tives (I,II) were formed. Condensation of furfural with acetone to give (XII). Condensation of I (or II or XII) with various H2N-B compounds to give 15 derivatives (III-XI, XIII- XVIII). The structure of the obtained products were characterized by elemental analysis and IR and 1H-NMR spectroscopy.The synthesized compounds were tested for biological ethylenic activities such as antibacterial and antifungal. Among these, two cetone a, b-ethylenic derivatives of 5-nitrofurfural (I,II) showed a high antibacterial activity on 10 strains of bacteria and a high antifungal activity against Candida albicans.
Chemical synthesis ; Physiological Effects of Drugs ; Furaldehyde ; Analogs & derivatives

In order to investigate the influencing factors of 5-hydroxymethyl-2-furaldehyde (5-HMF) content in Schisandra, confirm the theory of 5-HMF deriving mainly from Schisandra processing course, and give some suggestions about the Schisandra processing method, the 5-HMF contents in decoctions of Schisandra under different heating temperature, decocting time, soaking time, processing methods and treatment with different solvents before decocting the Schisandra were measured by RP-HPLC method. The results showed that there is great difference of 5-HMF level in decoctions from differently processed Schisandra and unprocessed Schisandra; decocting time of 60 min has some effects on 5-HMF level in decoctions and there is certain quantity 5-HMF in processed Schisandra itself and very little 5-HMF in unprocessed Schisandra. Heating time, heating temperature and treating solvents all have effect on 5-HMF level in decoction of Schisandra. 5-HMF in Schisandra was mainly from processing course. Both long heating time and high heating temperature can increase 5-HMF level in Schisandra. The production of 5-HMF in Schisandra may have some relationships with some polar components, which can dissolve in water, ethanol and acetone, especially in ethanol. To control processing temperature, processing time and treatment with some solvent is very important for controlling 5-HMF level in Schisandra.
Chromatography, High Pressure Liquid ; Furaldehyde ; analogs & derivatives ; analysis ; Plant Extracts ; chemistry ; Schisandra ; chemistry ; Temperature ; Time Factors

Byproducts in lignocellulose hydrolysates, namely sodium formate (1 to 5 g/L), sodium acetic (2.5 to 8.0 g/L), furfural (0.2-2 g/L), 5-hydroxymethylfurfural (5-HMF, 1 to 1.0 g/L) or vanillin (0.5 to 2 g/L) were used to evaluate their effects on ethanol fermentation by Issatchenkia orientalis HN-1 using single factor test and the response surface central composite experiment. Results showed that most of the byproducts had no obvious inhibition on the production of ethanol, except for the addition of 2 g/L vanillin or 1 g/L of 5-HMF, which reduced the ethanol production by 20.38% and 11.2%, respectively. However, high concentration of some byproducts in lignocellulose hydrolysates, such as sodium formate (1 to 5 g/L), sodium acetic (2.5 to 8.0 g/L), furfural (0.2 to 2 g/L) and vanillin (0.5 to 2 g/L) inhibited the growth of I. orientalis HN-1 significantly. Compared with the control, the dry cell weight of I. orientalis HN-1 decreased by 25.04% to 37.02%, 28.83% to 43.82%, 20.06% to 37.60% and 26.39% to 52.64%, respectively, when the above components were added into the fermentation broth and the fermentation lasted for 36 h. No significant interaction effect of the various inhibitors (sodium formate, sodium acetic, furfural and vanillin) except for vanillin single factor on the ethanol production was observed based on the central composite experiments. The concentrations of byproducts in most lignocellulose hydrolysates were below the initial inhibition concentration on ethanol production by Issatchenkia orientalis HN-1, which indicated that Issatchenkia orientalis HN-1 can be used for ethanol production from lignocellulose hydrolysates.
Ethanol ; metabolism ; Fermentation ; Furaldehyde ; analogs & derivatives ; chemistry ; Lignin ; chemistry ; Saccharomycetales ; metabolism

In order to investigate the mechanism, the correlation between the odor change in Crataegi Fructus stir-fried process and 5-HMF were studied. Required samples were retrieved from Crataegi Fructus stir-fried process. Statistical quality control (SQC) was used to analyze the response values acquired by the electronic nose. At the same time, the content of 5-HMF was detected by high performance liquid chromatography (HPLC). Correlation analysis was used to analyze the relationship between the above two. Experimental results showed that SQC model established by response values of all samples could show the change law of odor in Crataegi Fructus stir-fried process and changes of 5-HMF content was dropped after the first increase. Correlation analysis showed that the odor change in Crataegi Fructus stir-fried process and 5-HMF were significantly correlated (P < 0.05). Sugar degradation reaction and the Maillard reaction may be one of the mechanisms of the odor change in Crataegi Fructus stir-fried process.
Chromatography, High Pressure Liquid ; Crataegus ; chemistry ; Furaldehyde ; analogs & derivatives ; analysis ; Hot Temperature ; Odorants ; analysis ; Plant Extracts ; analysis ; Technology, Pharmaceutical ; methods

To get the tolerability and consumption of Klebsiella oxytoca on major inhibitors in lignocelluloses hydrolysate, we studied the effect of acetic acid, furfural and 5-hydroxymethylfurfural on production of 2,3-butanediol by Klebsiella oxytoca. The metabolites of furfural and 5-hydroxymethylfurfural were measured. The results show that when acetic acid, furfural and 5-hydroxymethylfurfural was individually added, tolerance threshold for Klebsiella oxytoca was 30 g/L, 4 g/L and 5 g/L, respectively. Acetic acid was likely used as substrate to produce 2,3-butanediol. The yield of 2,3-butanediol increased when acetic acid concentration was lower than 30 g/L. In the fermentation, more than 70% 5-hydroxymethylfurfural was converted to 2,5-furandimethanol. All furfural and the rest of 5-hydroxymethylfurfural were metabolized by Klebsiella oxytoca. It showed that in the detoxification process of 2,3-butanediol production using lignocelluloses hydrolysate, furfural should be given priority to remove and a certain concentration of acetic acid is not need to removal.
Acetic Acid ; chemistry ; Butylene Glycols ; metabolism ; Fermentation ; Furaldehyde ; analogs & derivatives ; chemistry ; Klebsiella oxytoca ; metabolism ; Lignin ; chemistry ; metabolism

This study aims to explore the key factors influencing the processing of braised Rehmanniae Radix, optimize the processing, and determine the correlation between the components in different processed products and chroma values, which is expected to add quantitative indexes for the processing of braised Rehmanniae Radix and better control the processing. The weights of the indexes catalpol, rehmannioside D, verbascoside, isoacteoside, 5-hydroxymethylfurfural, reducing sugar, and appearance were calculated based on analytic hierarchy process(AHP) in combination with coefficient of variation, and the overall desirability(OD) was obtained. Box-Behnken design was used to explore the optimal amount of water added, time for soaking with rice wine, and steaming time in the processing of braised Rehmanniae Radix. Colorimeter was employed to determine the chroma of 17 samples and raw samples, and SPSS, Prism, and other software to investigate the correlation between the components in braised Rehmanniae Radix and the chroma values. The results showed that each factor influenced the processing, and the influence followed the order of steaming time>amount of water added>time for soaking with rice wine. The optimal processing process is as below: A total of 100 g medicinal material was added with 7 times of water, followed by soaking with rice wine for 5 h and steaming in a pot for 6 h. The correlation analysis suggested the extremely significantly positive correlation between L~* and content of catalpol, between a~* and 5-hydroxymethylfurfural content, and between b~* and catalpol content, and the extremely significantly negative correlation between L~* and the content of 5-hydroxymethylfurfural and reducing sugar, and between b~* and the content of 5-hydroxymethylfural and reducing sugar. In this experiment, response surface methodology was used to optimize the processing technology of braised Rehmanniae Radix and the optimized process was rational and feasible. The content of chemical components in braised Rehmanniae Radix was significantly correlated with the chroma. This study provided a new method for the quality evaluation of braised Rehmanniae Radix.
Drugs, Chinese Herbal/chemistry* ; Excipients ; Furaldehyde/analogs & derivatives* ; Iridoid Glucosides ; Plant Extracts ; Rehmannia/chemistry* ; Sugars ; Technology ; Water

The origin of 5-HMF (5-hydroxymethyl-2-furaldehyde) in a Shengmaiyin decoction was investigated by the RP-HPLC method below. A C(18) column (250 mm x 4.6 mm, i.d. 5 microm) with a column temperature of 25 degrees C was used. The mobile phase was a mixture of ultra-pure water-acetonitrile (95:5, V/V) and the flow rate was 1.0 ml/min. The detection wavelength was 280 nm. The injection volume was 1 microl and the running time was about 20 min. The addition of Schisandra was regulated to assess the contribution of an acid environment to the production of 5-HMF. In order to confirm the role of saccharides in the production of 5-HMF, different amount of fructose was used. The 5-HMF level in decoctions of processed and unprocessed Schisandra was investigated in order to determine the origin of 5-HMF. The results showed that 5-HMF was derived mainly from the decoction of Schisandra only and not the mixed decoction of Ophionpogon and Schisandra. The appearance of 5-HMF is not simply the result of the decomposition of saccharides under the acid environment created by Schisandra, but the processing procedure plays an important role in the production of 5-HMF.
Chromatography, High Pressure Liquid ; Drug Combinations ; Drugs, Chinese Herbal ; chemistry ; Fructose ; metabolism ; Furaldehyde ; analogs & derivatives ; chemistry ; isolation & purification ; Hydrogen-Ion Concentration ; Schisandra ; chemistry

OBJECTIVETo develop the mechanism of improving protection function of prepared Cornus officinalis for liver and kidney and the biological activity of 5-hydroxymethylfurfural (5-HMF).

METHODPharmacological and chemical studies were used to choose active part. A compound from active part was separated and appraised. To investigate his biological functions, pharmacological experiment was actualized.

RESULTA component was separated and identified. His is 5-HMF. 5-HMF can protect human vein epidermal cell against H2O2 and glucose and inprove acute liver injury in mice.

CONCLUSION5-HMF is the active component in prepared Cornus officinalis and substance basis for protecting liver and kidney.

Animals ; Cells, Cultured ; Cornus ; chemistry ; Endothelial Cells ; drug effects ; Female ; Furaldehyde ; analogs & derivatives ; chemistry ; isolation & purification ; pharmacology ; Liver ; drug effects ; Male ; Mice ; Random Allocation

To compare the chemical change of Paeoniae Radix Alba (PRA) after vinegar-baking processing, as well as the effect of vinegar types exerted on the processing, 1H NMR-based metabolomic approach combined with multivariate statistical analysis was used to investigate the different metabolites between the raw and two vinegar-baked PRA. More than thirty metabolites were identified in the 1H NMR spectrum of PRA, and the multivariate statistical analysis showed that raw and two vinegar-baked PRA could be separated obviously. After vinegar-baking, the contents of isoleucine, lactate, alanine, arginine, albiflorin, and 5-hydroxymethyl furfural (5-HMF) elevated, while those of sucrose, paeoniflorin and its analogues (calculated by benzoate) decreased. The chemical compositions of two vinegar-baked PRA were also different. Shanxi vinegar- baked PRA showed higher levels of leucine, isoleucine, valine, and albiflorin, while rice vinegar-baked PRA contained more sucrose and paeoniflorin's analogues (calculated by benzoate). And the chemical changes in Shanxi vinegar-baked PRA were greater than those of rice vinegar-baked PRA. The results revealed the chemical differences between raw and vinegar-baked PRA, as well as the influence of vinegar type on processing, in a holistic manner, the results obtained suggested that the correlations between the chemical change and the drug action after processing, as well as the vinegar type used in processing, should be further studied.
Acetic Acid ; Benzoates ; Bridged-Ring Compounds ; Cooking ; Drugs, Chinese Herbal ; Furaldehyde ; analogs & derivatives ; Glucosides ; Metabolome ; Metabolomics ; Monoterpenes ; Paeonia ; chemistry ; Plant Roots ; chemistry

OBJECTIVETo find the changing regularity of 5-Hydroxymethyl furfuraldehyde (5-HMF) content in Radix Rehmanniae steamed for different time.

METHODHPLC method was used, with C18 column (6 mm x 200 mm, 5 microm), a mixture of methanol-water (15: 85) as the mobile phase. The flow rate was 1.0 mL x min(-1). The UV detection was setat 284 nm and the column temperature was set at 24 degrees C.

RESULTThe linear range was from 0.01 to 0.08 microg, r = 0.999 9 (n = 5). The average recovery was 100.2% and RSD was 2.7% (n = 5).

CONCLUSIONThe 5-HMF content increases as the processing time prolongs in a certain time rang.

Chromatography, High Pressure Liquid ; Furaldehyde ; analogs & derivatives ; analysis ; Hot Temperature ; Plants, Medicinal ; chemistry ; Quality Control ; Rehmannia ; chemistry ; Rhizome ; chemistry ; Technology, Pharmaceutical ; methods ; Time Factors