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Concept: Vanillin

172

BACKGROUND: Lignin is often overlooked in the valorization of lignocellulosic biomass, but lignin-based materials and chemicals represent potential value-added products for biorefineries that could significantly improve the economics of a biorefinery. Fluctuating crude oil prices and changing fuel specifications are some of the driving factors to develop new technologies that could be used to convert polymeric lignin into low molecular weight lignin and or monomeric aromatic feedstocks to assist in the displacement of the current products associated with the conversion of a whole barrel of oil. We present an approach to produce these chemicals based on the selective breakdown of lignin during ionic liquid pretreatment. RESULTS: The lignin breakdown products generated are found to be dependent on the starting biomass, and significant levels were generated on dissolution at 160[degree sign]C for 6 hrs. Guaiacol was produced on dissolution of biomass and technical lignins. Vanillin was produced on dissolution of kraft lignin and eucalytpus. Syringol and allyl guaiacol were the major products observed on dissolution of switchgrass and pine, respectively, whereas syringol and allyl syringol were obtained by dissolution of eucalyptus. Furthermore, it was observed that different lignin-derived products could be generated by tuning the process conditions. CONCLUSIONS: We have developed an ionic liquid based process that depolymerizes lignin and converts the low molecular weight lignin fractions into a variety of renewable chemicals from biomass. The generated chemicals (phenols, guaiacols, syringols, eugenol, catechols), their oxidized products (vanillin, vanillic acid, syringaldehyde) and their easily derivatized hydrocarbons (benzene, toluene, xylene, styrene, biphenyls and cyclohexane) already have relatively high market value as commodity and specialty chemicals, green building materials, nylons, and resins.

Concepts: Gasoline, Petroleum, Benzene, Lignin, Phenols, Vanillin, Guaiacol, Eugenol

171

The digestion of lignin and lignin-related phenolic compounds from bamboo by giant pandas has puzzled scientists because of the lack of lignin-degrading genes in the genome of the bamboo-feeding animals. We constructed a 16S rRNA gene library from the microorganisms derived from the giant panda feces to identify the possibility for the presence of potential lignin-degrading bacteria. Phylogenetic analysis showed that the phylotypes of the intestinal bacteria were affiliated with the phyla Proteobacteria (53%) and Firmicutes (47%). Two phylotypes were affiliated with the known lignin-degrading bacterium Pseudomonas putida and the mangrove forest bacteria. To test the hypothesis that microbes in the giant panda gut help degrade lignin, a metagenomic library of the intestinal bacteria was constructed and screened for clones that contained genes encoding laccase, a lignin-degrading related enzyme. A multicopper oxidase gene, designated as lac51, was identified from a metagenomic clone. Sequence analysis and copper content determination indicated that Lac51 is a laccase rather than a metallo-oxidase and may work outside its original host cell because it has a TAT-type signal peptide and a transmembrane segment at its N-terminus. Lac51 oxidizes a variety of lignin-related phenolic compounds, including syringaldazine, 2,6-dimethoxyphenol, ferulic acid, veratryl alcohol, guaiacol, and sinapinic acid at conditions that simulate the physiologic environment in giant panda intestines. Furthermore, in the presence of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), syringic acid, or ferulic acid as mediators, the oxidative ability of Lac51 on lignin was promoted. The absorbance of lignin at 445 nm decreased to 36% for ABTS, 51% for syringic acid, and 51% for ferulic acid after incubation for 10 h. Our findings demonstrate that the intestinal bacteria of giant pandas may facilitate the oxidation of lignin moieties, thereby clarifying the digestion of bamboo lignin by the animal.

Concepts: Protein, Archaea, Bacteria, Gut flora, Enzyme, 16S ribosomal RNA, Giant Panda, Vanillin

154

Cranberry consumption has shown prophylactic effects against urinary tract infections (UTI), although the mechanisms involved are not completely understood. In this paper, cranberry phenolic compounds and their potential microbial-derived metabolites (such as simple phenols and benzoic, phenylacetic and phenylpropionic acids) were tested for their capacity to inhibit the adherence of uropathogenic Escherichia coli (UPEC) ATCC®53503™ to T24 epithelial bladder cells. Catechol, benzoic acid, vanillic acid, phenylacetic acid and 3,4-dihydroxyphenylacetic acid showed anti-adhesive activity against UPEC in a concentration-dependent manner from 100-500 µM, whereas procyanidin A2, widely reported as an inhibitor of UPEC adherence on uroepithelium, was only statistically significant (p < 0.05) at 500 µM (51.3% inhibition). The results proved for the first time the anti-adhesive activity of some cranberry-derived phenolic metabolites against UPEC in vitro, suggesting that their presence in the urine could reduce bacterial colonization and progression of UTI.

Concepts: Kidney, Urinary tract infection, Urine, Escherichia coli, Urinary bladder, Urinary system, Catechin, Vanillin

29

Profound research has been done on the medicinal value of Brassica nigra (BN) seeds, and the leaves of the plant have been investigated in this study. The methanol extracts of the leaves were subjected to several in vitro studies. The antioxidant activity of methanol extract was demonstrated with a wide range of concentration, 10-500 µg mL(-1), and the antioxidant activity increased with the increase in concentration. Total phenol content was found to be 171.73 ± 5.043 gallic acid equivalents and the total flavonoid content 7.45 ± 0.0945 quercetin equivalents. Further quantification and identification of the compounds were done by HPTLC and GC-MS analyses. The predominant phenolic compounds determined by HPTLC were gallic acid, followed by quercetin, ferulic acid, caffeic acid and rutin. The free radical quenching property of BN leaf extract suggests the presence of bioactive natural compounds.

Concepts: Catechin, Quercetin, Caffeic acid, Resveratrol, Phenols, Ferulic acid, Gallic acid, Vanillin

28

This review provides an overview of biovanillin production from agro wastes as an alternative food flavour. Biovanillin is one of the widely used flavour compounds in the foods, beverages and pharmaceutical industries. An alternative production approach for biovanillin as a food flavour is hoped for due to the high and variable cost of natural vanillin as well as the limited availability of vanilla pods in the market. Natural vanillin refers to the main organic compound that is extracted from the vanilla bean, as compared to biovanillin, which is produced biologically by microorganisms from a natural precursor such as ferulic acid. Biovanillin is also reviewed as a potential bioflavour produced by microbial fermentation in an economically feasible way in the near future. In fact, we briefly discuss natural, synthetic and biovanillin and the types of agro wastes that are useful as sources for bioconversion of ferulic acid into biovanillin. The subsequent part of the review emphasizes the current application of vanillin as well as the utilization of biovanillin as an alternative food flavour. The final part summarizes biovanillin production from agro wastes that could be of benefit as a food flavour derived from potential natural precursors.© 2012 Society of Chemical Industry.

Concepts: Microbiology, Food, Organic chemistry, Chemical compound, Flavor, Fermentation, Vanillin, Vanilla

28

Plant roots react to pathogen attack by the activation of general and systemic resistance, including the lignification of cell walls and increased release of phenolic compounds in root exudate. Some fungi have the capacity to degrade lignin using ligninolytic extracellular peroxidases and laccases. Aromatic lignin breakdown products are further catabolized via the β-ketoadipate pathway. In this study, we investigated the role of 3-carboxy-cis,cis-muconate lactonizing enzyme (CMLE), an enzyme of the β-ketoadipate pathway, in the pathogenicity of Fusarium oxysporum f. sp. lycopersici towards its host, tomato. As expected, the cmle deletion mutant cannot catabolize phenolic compounds known to be degraded via the β-ketoadipate pathway. In addition, the mutant is impaired in root invasion and is nonpathogenic, even though it shows normal superficial root colonization. We hypothesize that the β-ketoadipate pathway in plant-pathogenic, soil-borne fungi is necessary to degrade phenolic compounds in root exudate and/or inside roots in order to establish disease.

Concepts: Bacteria, Enzyme, Plant, Cell wall, Lignin, Fusarium oxysporum, Root, Vanillin

28

Smoke taint in wines from bushfire smoke exposure has become a concern for wine producers. Smoke taint compounds are primarily derived from pyrolysis of the lignin component of fuels. This work examined the influence of the lignin composition of pyrolysed vegetation on the types of putative smoke taint compounds that accrue in wines. At veraison, Merlot vines were exposed to smoke generated from five vegetation types with differing lignin composition. Smoke was generated under pyrolysis conditions that simulated bushfire temperature profiles. Lignin and smoke composition of each fuel type along with putative smoke taint compounds in wines were determined. The results showed that, regardless of fuel type, the commonly reported guaiacyl lignin derived smoke taint compounds, guaiacol and 4-methylguaiacol, represented about 20% of the total phenols in wines. Quantitatively, syringyl lignin derived compounds dominated the total phenol pools in both free and bound forms. The contributions of p-hydroxyphenyls were generally similar to the guaiacyl sources. A further unexpected outcome of the study was that pine smoke affected wines had significantly elevated levels of syringols compared to the controls although pine fuel and its smoke emission lacked syringyl products.

Concepts: Lignin, Smoke, Wine, Phenols, Vanillin, Combustion, Grape, Guaiacol

28

Most research studies in the field of dietary polyphenols or phenolic compounds use a chemical approach focusing exclusively on polyphenols extracted from plant foods with organic solvents. However, an appreciable part of polyphenols are not extracted with organic solvents and thus are ignored in biological, nutritional, and epidemiological studies. Recent studies have shown that these nonextractable polyphenols (NEPP) are a major part of total dietary polyphenols and that they exhibit a significant biological activity. A physiological approach is proposed on the basis that the bioavailability and health-related properties of polyphenols depend on their solubility in intestinal fluids, which is different from their solubility in organic solvents. This paper tries to clarify the concept of NEPP, distinguishing between chemical and physiological approaches and pointing out the main qualitative and quantitative differences between them. It is stressed that the literature and databases refer to only extractable polyphenols. Greater attention to NEPP may fill the current gap in the field of dietary polyphenols.

Concepts: Epidemiology, Solubility, Solvent, Qualitative research, Catechin, Resveratrol, Phenols, Vanillin

27

Lignin valorization practices have attracted a great deal of interest in recent years due to the large excess of lignin produced by the pulp and paper industry, together with second-generation bioethanol plants. In this work, a new lignin valorization approach is proposed. It involves ultrafiltration as a fractionation process to separate different molecular weight lignin fractions followed by a hydrogen-free, mild, hydrogenolytic, heterogeneously catalyzed methodology assisted by microwave irradiation to obtain simple phenolic, monomeric products by depolymerization using a nickel-based catalyst. The main products obtained were desaspidinol, syringaldehyde, and syringol; this proves the efficiency of the depolymerization conditions applied. The concentration of these observed compounds increased when the molecular weights of the lignin fractions increased. The applied depolymerization conditions, which take advantage of the use of formic acid as a hydrogen-donating solvent, did not generate any biochar in the systems.

Concepts: Oxygen, Acetic acid, Solvent, Vanillin, Molecular mass, Methanol, Formic acid, Pulp and paper industry

27

Hydrolysates of lignocellulosic biomass, used as substrates for the sustainable production of fuels and chemicals often contain high amounts of phenolic compounds inhibiting the production microbiota. Quantification of these inhibitor compounds may help to understand possible difficulties in bioprocessing and further the development of more efficient, robust and tolerable processes. A separation method based on capillary electrophoresis with UV detection was developed for the simultaneous quantification of 10 phenolic compounds that may have inhibitor properties. Intraday relative standard deviations were less than 0.7% for migration times and between 2.6% and 6.4% for peak areas. Interday relative standard deviations were less than 3.0% for migration times and between 5.0% and 7.2% for peak areas. The method was applied to demonstrate that Saccharomyces cerevisiae was able to decrease the concentrations of vanillin, coniferyl aldehyde, syringaldehyde, acetoguaiacone and cinnamic acid during the cultivation, whereas the concentrations of phenols increased.

Concepts: Gel electrophoresis, Saccharomyces cerevisiae, Saccharomyces pastorianus, Saccharomyces, Phenols, Vanillin, Phenolic compounds in wine, Robust statistics