5-hydroxymethylfurfural and ferulic-acid

For 2G ethanol production, pentose fermentation and yeast tolerance to lignocellulosic hydrolyzate components are essential to improve biorefinery yields. Generally, physicochemical pre-treatment methodologies are used to facilitate access to cellulose and hemicellulose in plant material, which consequently can generate microbial growth inhibitory compounds, such as furans, weak acids, and phenolic compounds. Because of the unsatisfactory yield of wild-type Saccharomyces cerevisiae during pentose fermentation, the search for xylose-fermenting yeasts tolerant to microbial growth inhibitors has gained attention. In this study, we investigated the ability of the yeasts Pichia guilliermondii G1.2 and Candida oleophila G10.1 to produce ethanol from xylose and tolerate the inhibitors furfural, 5-hydroxymethylfurfural (HMF), acetic acid, formic acid, ferulic acid, and vanillin. We demonstrated that both yeasts were able to grow and consume xylose in the presence of all single inhibitors, with greater growth limitation in media containing furfural, acetic acid, and vanillin. In saline medium containing a mixture of these inhibitors (2.5-3.5 mM furfural and HMF, 1 mM ferulic acid, 1-1.5 mM vanillin, 10-13 mM acetic acid, and 5-7 mM formic acid), both yeasts were able to produce ethanol from xylose, similar to that detected in the control medium (without inhibitors). In future studies, the proteins involved in the transport of pentose and tolerance to these inhibitors need to be investigated.

Topics: Biomass; Ethanol; Fermentation; Formates; Furaldehyde; Furans; Pentoses; Phenols; Pichia; Saccharomyces cerevisiae; Xylose

Oleaginous fungus Mortierella isabellina showed excellent lipid conversion on non-detoxified lignocellulosic hydrolysate. This study investigated the effects of inhibitory compounds (furfural, hydroxymethylfurfural, and ferulic and coumaric acids) in lignocellulosic hydrolysate on M. isabellina growth and lipid production. M. isabellina can tolerate furfural (∼1 g/L), hydroxymethylfurfural (∼2.5 g/L), ferulic (∼0.5 g/L) and coumaric acid (∼0.5 g/L) with normal growth rates. Synergistic effect of these inhibitors (2 g/L furfural, 0.4 g/L hydroxymethylfurfural, 0.02 g/L ferulic acid and 0.02 g/L coumaric acid) moderately reduces total fungal growth (by 28%), while the presence of these inhibitors has minor impact on cell lipid contents and lipid profiles. In the presence of inhibitory compounds, (13)C-tracing has revealed that M. isabellina can simultaneously utilize glucose and acetate, and acetate is mainly assimilated for synthesis of lipid and TCA cycle amino acids. The results also demonstrate that glucose has strong catabolite repression for xylose utilization for biomass and lipid production in the presence of inhibitors.

Topics: Amino Acids; Carbon; Carbon Isotopes; Coumaric Acids; Fatty Acids; Fermentation; Furaldehyde; Hydrolysis; Isotope Labeling; Kinetics; Lignin; Lipid Metabolism; Mortierella

Palmul-tang, a traditional herbal medicine, is composed of eight herbs (Ginseng radix, Glycyrrhizae radix, Hoelen, Atractylodis rhizoma, Angelicae gigantis radix, Cnidii rhizoma, Paeoniae radix and Rehmanniae radix) and exhibits various bioactivities, including antiallergic and antitumor effects. In this study, an effective, reliable and accurate high-performance liquid chromatography method has been developed for the simultaneous determination of 11 marker components in Palmul-tang: hydroxymethylfurfural, albiflorin, paeoniflorin, ferulic acid, nodakenin, ginsenoside Rg1, decursinol, glycyrrhizin, 6-gingerol, ginsenoside Rg3 and decursin. All calibration curves of the 11 components indicated excellent linearity (correlation coefficient > 0.9997) within the test range. The limits of detection and quantification of each component were in the ranges of 0.08-1.03 and 0.23-3.11 µg/mL, respectively. The intra-day and inter-day relative standard deviation values were within 1.65 and 2.71%, respectively. The mean recovery values were 94.49 to 101.10%. The established method was successfully applied to the simultaneous determination of 11 major components in 12 commercial samples of Palmul-tang. The developed analytical method is simple and suitable for the quality control of Palmul-tang.

Topics: Angelica; Atractylodes; Bridged-Ring Compounds; Catechols; Chromatography, High Pressure Liquid; Coumaric Acids; Coumarins; Drugs, Chinese Herbal; Fatty Alcohols; Furaldehyde; Glucosides; Glycyrrhiza; Glycyrrhizic Acid; Monoterpenes; Panax; Rehmannia; Reproducibility of Results; Tandem Mass Spectrometry

Angelica polymorpha Maxim. is a plant of the Angelica genus (Umbelliferae). The root and stem of this plant is a folk medicine known to have the actions of relieving rheumatism and cold and subsiding swelling and pains. To investigate the chemical constituents in the root of A. polymorpha Maxim., seven compounds were isolated from an 80% ethanol extract by column chromatography. Their structures were elucidated according to the spectroscopic analysis. Compound 1 is a new sesquiterpene, named as bisabolactone. Its absolute configuration was determined by 1D NOESY and CD analysis. The others were identified as 5-hydroxymethylfurfural (2), hycandinic acid ester 1 (3), ferulic acid (4), isooxypeucedanin (5), noreugenin (6) and cimifugin (7). Compound 2 and 3 were isolated from this genus for the first time and compound 4 was isolated from this plant for the first time.

Topics: Angelica; Chromones; Coumaric Acids; Coumarins; Furaldehyde; Molecular Structure; Plant Roots; Plants, Medicinal; Quinic Acid; Sesquiterpenes

A simple and accurate high-performance liquid chromatographic method was applied to the quantitative analysis of seven components of the traditional herbal prescription Jaeumganghwa-tang (JGT), including 5-hydroxymethyl-2-furaldehyde, albiflorin, paeoniflorin, liquiritin, ferulic acid, nodakenin, and glycyrrhizin. All seven compounds were separated in less than 40 min on a Gemini C18 column at 40°C by gradient elution using 1.0% (v/v) aqueous acetic acid and acetonitrile containing 1.0% (v/v) acetic acid as mobile phase. The flow rate was 1.0 mL/min and the detector was a photodiode array (PDA) set at 230 nm, 254 nm, 280 nm, and 330 nm. The calibration curves showed good linearity (r (2) > 0.9998) in different concentration ranges. The recovery of each component was in the range of 91.47-102.62%, with relative standard deviations (RSDs, %) less than 4.5%. The RSDs (%) for intra- and interday precision were 0.06-2.85% and 0.06-2.83%, respectively. The concentrations of the seven components in JGT were in the range 0.74-5.48 mg/g.

Topics: Benzoates; Bridged-Ring Compounds; Chromatography, High Pressure Liquid; Coumaric Acids; Coumarins; Drugs, Chinese Herbal; Flavanones; Furaldehyde; Glucosides; Glycyrrhizic Acid; Magnoliopsida; Monoterpenes

A high-performance liquid chromatographic (HPLC) method was developed for quantitative analysis of seven components, 5-hydroxymethyl-2-furaldehyde (1), albiflorin (2), paeoniflorin (3), liquiritin (4), ferulic acid (5), nodakenin (6), and glycyrrhizin (7) of Palmul-tang (PMT), a traditional Korean medicine. HPLC analysis was performed using a Gemini C18 column at 40°C, and photodiode array (PDA) detection at 230 nm, 254 nm, 280 nm, 320 nm, and 330 nm was used for quantification of the seven components in PMT. The mobile phase was a gradient flow composed of two solvent systems. Solvent A was 1.0% (v/v) aqueous acetic acid and solvent B was acetonitrile containing 1.0% (v/v) acetic acid. Calibration curves were acquired with r (2) values > 0.9998, and the relative standard deviations (RSDs, %) for intra- and interday precision were both less than 6.0%. The recovery of each component was in the range of 90.66-103.79%, with a RSD less than 5.0%. The contents of the seven components in PMT range form 0.61-6.21 mg/g. Additionally, we investigated the cytotoxicity of the extract against the RBL-1 and BEAS-2B cell lines, as well as splenocytes.

Topics: Animals; Benzoates; Bridged-Ring Compounds; Cell Line, Tumor; Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Coumaric Acids; Coumarins; Cytotoxins; Drug Evaluation, Preclinical; Flavanones; Furaldehyde; Glucosides; Glycyrrhizic Acid; Medicine, Korean Traditional; Mice; Mice, Inbred BALB C; Monoterpenes; Plant Preparations; Rats

Coffee shows distinct antimicrobial activity against several bacterial genera. The present study investigated molecular mechanisms and active ingredients mediating the antimicrobial effect of coffee. Depending on concentration, roasted, but not raw coffee brew inhibited the growth of Escherichia coli and Listeria innocua. Several coffee ingredients with known antibacterial properties were tested for their contribution to the observed effect. In natural concentration, caffeine, ferulic acid and a mixture of all test compounds showed very weak, but significant activity, whereas trigonelline, 5-(hydroxymethyl)furfural, chlorogenic acid, nicotinic acid, caffeic acid, and methylglyoxal were not active. Antimicrobial activity, however, was completely abolished by addition of catalase indicating that H(2)O(2) is a major antimicrobial coffee component. In accordance with this assumption, bacterial counts during 16 h of incubation were inversely related to the H(2)O(2) concentration in the incubation solution. Pure H(2)O(2) showed slightly weaker activity. The H(2)O(2) dependent antimicrobial activity of coffee could be mimicked by a reaction mixture of d-ribose and l-lysine (30 min 120 °C) indicating that H(2)O(2) is generated in the coffee brew by Maillard reaction products. Identification of H(2)O(2) as major antimicrobial coffee component is important to evaluate the application of coffee or coffee extracts as natural preservatives.

Topics: Alkaloids; Anti-Infective Agents; Caffeine; Chlorogenic Acid; Coffee; Coumaric Acids; Culture Media; Escherichia coli; Furaldehyde; Hydrogen Peroxide; Listeria; Lysine; Plant Extracts; Ribose; Temperature

Acid pretreatment of lignocellulosic biomass releases furan and phenolic compounds, which are toxic to microorganisms used for subsequent fermentation. In this study, we isolated new microorganisms for depletion of inhibitors in lignocellulosic acid hydrolysates. A sequential enrichment strategy was used to isolate microorganisms from soil. Selection was carried out in a defined mineral medium containing a mixture of ferulic acid (5 mM), 5-hydroxymethylfurfural (5-HMF, 15 mM), and furfural (20 mM) as the carbon and energy sources, followed by an additional transfer into a corn stover hydrolysate (CSH) prepared using dilute acid. Subsequently, based on stable growth on these substrates, six isolates--including five bacteria related to Methylobacterium extorquens, Pseudomonas sp, Flavobacterium indologenes, Acinetobacter sp., Arthrobacter aurescens, and one fungus, Coniochaeta ligniaria--were chosen. All six isolates depleted toxic compounds from defined medium, but only C. ligniaria C8 (NRRL 30616) was effective at eliminating furfural and 5-HMF from CSH. C. ligniaria NRRL 30616 may be useful in developing a bioprocess for inhibitor abatement in the conversion of lignocellulosic biomass to fuels and chemicals.

Topics: Acids; Bacteria; Biodegradation, Environmental; Carboxylic Acids; Cellulose; Coumaric Acids; Culture Media; DNA, Ribosomal; Fermentation; Fungi; Furaldehyde; Furans; Genes, rRNA; Growth Inhibitors; Hydrolysis; Lignin; Molecular Sequence Data; Phenols; RNA, Ribosomal, 18S; Sequence Analysis, DNA; Soil Microbiology; Sordariales