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PubMed1999

Comparison of fungal laccases and redox mediators in oxidation of a nonphenolic lignin model compound.

Several fungal laccases have been compared for the oxidation of a nonphenolic lignin dimer, 1-(3, 4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propan-1,3-diol (I), and a phenolic lignin model compound, phenol red, in the presence of the redox mediators 1-hydroxybenzotriazole (1-HBT) or violuric acid. The oxidation rates of dimer I by the laccases were in the following order: Trametes villosa laccase (TvL) > Pycnoporus cinnabarinus laccase (PcL) > Botrytis cinerea laccase (BcL) > Myceliophthora thermophila laccase (MtL) in the presence of either 1-HBT or violuric acid. The order is the same if the laccases are used at the same molar concentration or added to the same activity (with ABTS [2, 2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid)] as a substrate). During the oxidation of dimer I, both 1-HBT and violuric acid were to some extent consumed. Their consumption rates also follow the above order of laccases, i.e., TvL > PcL > BcL > MtL. Violuric acid allowed TvL and PcL to oxidize dimer I much faster than 1-HBT, while BcL and violuric acid oxidized dimer I more slowly than BcL and 1-HBT. The oxidation rate of dimer I is dependent upon both kcat and the stability of the laccase. Both 1-HBT and violuric acid inactivated the laccases, violuric acid to a greater extent than 1-HBT. The presence of dimer I or phenol red in the reaction mixture slowed down this inactivation. The inactivation is mainly due to the reaction of the redox mediator free radical with the laccases. We did not find any relationship between the carbohydrate content of the laccases and their inactivation. When the redox potential of the laccases is in the range of 750 to 800 mV, i.e., above that of the redox mediator, it does not affect kcat and the oxidation rate of dimer I.

Barbiturates↗
PubMed1973

Bile acids and vitamin A absorption in man: the effects of two bile acid-binding agents, cholestyramine and lignin.

In 14 healthy volunteers, the addition of 12 g cholestyramine to a vitamin A-containing test meal reduced the expected rise in serum vitamin A by 59.5% (p<0.001). By contrast, lignin had no significant effect in 12 subjects. This study confirms the importance of bile acids in vitamin A absorption and the ineffectiveness of lignin as a sequestrator of conjugated bile acids.

Adult↗
PubMed1986

Effects of the fibre components pectin, cellulose, and lignin on bile salt metabolism and biliary lipid composition in man.

Randomised crossover studies in three separate groups of 10 healthy volunteers were undertaken to determine the effects of biliary lipid composition and bile salt metabolism of daily dietary supplementation for four weeks with the purified fibre components pectin (12 g/day), cellulose (15 g/day) and lignin (12 g/day). The subjects' biles were initially unsaturated with cholesterol and no significant changes in the lithogenic indices or mean percentages of cholesterol, phospholipid, or total bile acids after any of the supplements were observed. After pectin, the mean (+/- SD) percentage of cholic acid decreased significantly from 42.8 (+/- 10.8) to 39.0 (+/- 11.2), the mean (+/- SD) percentage of deoxycholic acid increased significantly from 18.2 (+/- 13.7) to 25.4 (+/- 13.5) and C14-deoxycholate metabolites were raised significantly by 65%. After cellulose, the mean (+/- SD) percentage of chenodeoxycholic acid was increased significantly from 33.6 (+/- 6.3) to 35.4 (+/- 7.0), the mean (+/- SD) percentage of deoxycholic acid decreased significantly from 18.6 (+/- 9.6) to 14.2 (+/- 8.3) and C14-deoxycholate metabolites halved. Lignin did not exert any significant effects. Though these results show that individual fibre components are associated with quite different effects on bile acid metabolism, in the short term no significant effect on biliary cholesterol saturation was observed in bile initially unsaturated with cholesterol. The bile acid changes most likely result from the different effects on colonic metabolism induced by the individual fibre components.

Adult↗
PubMed1992

Lignified materials as medicinal resources. V. Anti-HIV (human immunodeficiency virus) activity of some synthetic lignins.

A class of synthetic lignins (dehydrogenation polymers of p-coumaric acid, ferulic acid, and caffeic acid) inhibited cytopathogenicity of HIV-1 and HIV-2 infection. The ratio of cytotoxic to anti-HIV (human immunodeficiency virus) doses depended strongly on conditions during polymer preparation. The activity increased when polymers were treated with reducing agent NaBH4, whereas it decreased when treated with oxidizing agent ceric ammonium nitrate. The polymers inhibited expression of HIV-specific antigen in the infected cells and also inhibited HIV-binding to the cells, but not completely, even at doses that almost completely inhibited the HIV-induced cytopathogenic effect. These results suggest that lignin structure, regardless of whether synthetic or natural, may inhibit HIV replication by an unidentified process, and thus prove to be a new class of anti-HIV agents possibly effective in the treatment of AIDS (acquired immunodeficiency syndrome).

Antiviral Agents↗
PubMed1997

Immunopotentiating activity of the water-soluble lignin rich fraction prepared from LEM--the extract of the solid culture medium of Lentinus edodes mycelia.

The water-soluble lignin in LEM (the extract of the solid culture medium of Lentinus edodes mycelia) has been known to have antiviral and immunopotentiating activities in vivo and in vitro. The water-soluble lignin rich fraction (JLS-18) was prepared from LEM using ultrafiltration and hydrophobic column chromatography. JLS-18 showed about 70 times higher antiviral activity than LEM in vitro. JLS-18 activated the cytotoxicity of NK cells and macrophages, and activated T cells in vitro. JLS-18 also induced interleukin 6 (IL-6) secretion from human leukocytes infected with Sendai virus in vitro. These data showed that JLS-18, the water-soluble rich fraction of LEM, had antiviral and immunopotentiating activities.

Adjuvants, Immunologic↗
PubMed1999

HIV-1 protease inhibition and anti-HIV effect of natural and synthetic water-soluble lignin-like substances.

Water-soluble lignin extracted from natural sources and dehydrogenated polymers of p-coumaric acid and ferulic acid inhibited HIV-1 protease activity. The dehydrogenated polymers, which are thought to be model compounds for lignin, were synthesized and fractionated into four ranges of molecular mass by ultra-filtration: i.e., over 30 kDa, 30-10 kDa, 10-1 kDa and 1 kDa-500 Da. All of these fractions had HIV-1 protease inhibitory activity. The anti-HIV-1 effect of the smallest mass fractions of the dehydrogenated polymers (1 kDa-500 Da) was also tested, and it was found that these fractions inhibited the replication of HIV-1 in MT-4 cells.

Cell Line↗
PubMed2001

Oxidative lime pretreatment of high-lignin biomass: poplar wood and newspaper.

Lime (Ca[OH]2) and oxygen (O2) were used to enhance the enzymatic digestibility of two kinds of high-lignin biomass: poplar wood and newspaper. The recommended pretreatment conditions for poplar wood are 150 degrees C, 6 h, 0.1 g of Ca(OH)2/g of dry biomass, 9 mL of water/g of dry biomass, 14.0 bar absolute oxygen, and a particle size of -10 mesh. Under these conditions, the 3-d reducing sugar yield of poplar wood using a cellulase loading of 5 filter paper units (FPU)/g of raw dry biomass increased from 62 to 565 mg of eq. glucose/g of raw dry biomass, and the 3-d total sugar (glucose + xylose) conversion increased from 6 to 77% of raw total sugars. At high cellulase loadings (e.g., 75 FPU/g of raw dry biomass), the 3-d total sugar conversion reached 97%. In a trial run with newspaper, using conditions of 140 degrees C, 3 h, 0.3 g of Ca(OH)2/g of dry biomass, 16 mL of water/g of dry biomass, and 7.1 bar absolute oxygen, the 3-d reducing sugar yield using a cellulase loading of 5 FPU/g of raw dry biomass increased from 240 to 565 mg of eq. glucose/g of raw dry biomass. A material balance study on poplar wood shows that oxidative lime pretreatment solubilized 38% of total biomass, including 78% of lignin and 49% of xylan; no glucan was removed. Ash increased because calcium was incorporated into biomass during the pretreatment. After oxidative lime pretreatment, about 21% of added lime could be recovered by CO2 carbonation.

Biomass↗
PubMed2003

Field activity and storage stability of Anagrapha falcifera nucleopolyhedrovirus (AfMNPV) in spray-dried lignin-based formulations.

A multiple-embedded nucleopolyhedrovirus isolated from Anagrapha falcifera (Kirby) (AfMNPV) has potential to be developed into a microbial bioinsecticide because the host range includes several economic pests. We tested spray-dried AfMNPV formulations after storage for insecticidal activity based on bioassays with neonate Trichoplusia ni (Hübner). Eight experimental lignin-based spray-dried formulations, a glycerin-based formulation, and an unformulated sample were made with virus stock from three commercial production lots. Samples of these formulations were stored at 30 degrees C in individually sealed sample containers for destructive sampling after 1, 3, and 6 mo whereas the remaining product was stored in glass jars under refrigeration for up to 30 mo. Spray drying did not significantly reduce the initial LC50s of AfMNPV in experimental formulations compared with unformulated virus that was not spray dried. Refrigerated storage for 6 mo did not significantly lower virus activity of formulated samples compared with the unformulated AfMNPV stored frozen, while samples stored for 30 mo had higher LC50 values determined by both droplet and leaf feeding assays. When stored at 30 degrees C, most formulations (22 of 24) maintained insecticidal activity for 3 mo, but most (21 of 24) lost significant activity after 6 mo of storage. The glycerin-based formulation also lost activity within 6 mo of storage at 30 degrees C when compared with frozen unformulated virus, but did not lose activity when stored refrigerated for up to 30 mo. These formulations were evaluated after 7 mo at 4 degrees C for residual insecticidal activity when applied to field grown cabbage. Insecticidal activity was determined against T. ni neonates for treated leaf samples collected at 3, 7, 27, and 51 h after application of 2.5 x 10(12) obs/ha. Field tests showed no differences in activity among samples of stored formulations and one freshly made formulation. Spray-dried formulations had significantly higher insecticidal activity (67.5% mortality) compared with the unformulated treatment (30% mortality) sampled 3 h after application. At 3, 7, and 27 h after application, the spray-dried formulations had higher residual activity (67%, 59%, and 42% mortality, respectively), compared with the commercial glycerin-based formulation (61%, 38%, and 23% mortality, respectively). These experiments demonstrated that AfMNPV in lignin-based spray-dried formulations had a shelf-life of up to 3 mo at 30 degrees C and up to 30 mo at 4 degrees C, and with longer residual insecticidal activity in the field compared with unformulated or a glycerin formulation.

Animals↗
PubMed1990

Digestibility and feeding value of pearl millet as influenced by the brown-midrib, low-lignin trait.

Our objectives were to determine the intake and digestibility of pearl millet as influenced by the brown-midrib (BMR), low-lignin trait and to determine the relative acceptability of BMR pearl millet in relation to its normal counterpart. Two field replicates of brown-midrib pearl millet and its normal counterpart were harvested as hay at the boot to heading stage twice during the growing season (2 genotypes x 2 cuttings x 2 field replicates). Twenty-four wethers had ad libitum access to a total forage diet (pearl millet forage), water and trace mineralized salt. The experimental period was 21 d (14 d for adjustment and 7 d for sample collection). Lignin was 23% lower (P less than or equal to .01) and in vitro DM digestibility (IVDMD) was 4% higher (P less than or equal to .01) in BMR vs normal genotype forages. Wethers preferred first-cutting millet to second-cutting millet, as evidenced by 62% higher (P less than or equal to .01) DMI for first-cutting forages. Dry matter intake of second-cutting forages was higher (P less than or equal to .10) for BMR pearl millet forage than for normal pearl millet (2.0 vs 1.5% of BW), but first-cutting forages were similar in DMI (2.9% of BW). In an acceptability trial of pearl millet regrowth (4 wk), grazing lambs with access to both genotypes displayed a marked preference (P less than .01) for the BMR genotype, spending an average of 2.6 min on plots containing the brown-midrib pearl millet for every minute spent on the normal genotype.(ABSTRACT TRUNCATED AT 250 WORDS)

Animal Feed↗
PubMed1995

Radical intermediates during degradation of lignin-model compounds and environmental pollutants: an electron spin resonance study.

1. I discuss the following aspects of Phanerochaete chrysosporium ligninase, the enzyme that has been shown to degrade a number of lignin-model compounds, and environmentally significant polycyclic aromatic hydrocarbons and polychlorinated phenols. 2. The primary mode of oxidation involves formation of a cation radical, which undergoes either hydrolysis or carbon-carbon bond cleavage. 3. In the presence of reducing substrate such as oxalic acid, ligninase has reductive activity that has been shown to be responsible for radical-mediated degradation of halogenated chemicals. 4. Electron spin resonance technique can be used to monitor the cation radical and other radical formation during ligninase-mediated degradation of lignin-model compounds and other chemicals.

Animals↗
PubMedDate not supplied

[Changes in macromolecular characteristics and biological activity of hydrolytic lignin hydrolysate in the course of composting].

Composting of hydrolytic lignin by a microbial association changed its molecular-weight composition, acid-based properties, and supramolecular structure. Specifically, by the end of the third month of composting, an increase was observed in its exchange capacity and the amount of negative charges, as well as in the content of phenyl, hydroxyl, and carboxyl groups. The use of this compost as a fertilizer for barley growth demonstrated that the changes increased the biological activity of hydrolytic lignin.

Biodegradation, Environmental↗
PubMed2002

[Biodegradation of lignin in wheat straw by alkaliphilic ligninolytic bacteria with compounded carbons].

The article researched enzymes production, the degradation rate of lignin and strain growth of alkaliphilic ligninolytic bacteria strain No. 6 in alkaline liquid medium (pH approximately 10.5) with compounded carbons. The results showed that the highest activities of laccase and MnP were 2915.37 U/L (4th d) and 1152.88 U/L (8th d), respectively, and the strain degraded 49.84% lignin of wheat straw during ten days cultivation. The changes of ultrastructure of wheat straw caused by strain No. 6 attack were investigated with SEM (scan electron microscopy).

Bacteria↗
PubMed2004

[The lignins from Torreya grandis cv. Merrilli].

AIM: To separate and identify the chemical constituents of the aril of Torreya grandis cv. Merrilli. METHODS: Three lignins were isolated by chromatography and their chemical structures were elucidated by IR, EI-MS, 1HNMR, 13CNMR, DEPT and 2D-NMR spectral methods. RESULTS: Three lignins were identified as pinonesinol, dihydrodehydrodiconiferylalcohol and (7,8-cis-8,8'-trans)-2',4'dihydroxyl-3, 5-dimethoxy-lariciresinol. CONCLUSION: These compounds were isolated from this plant for the first time, and compound III is a new compound.

Fruit↗
PubMed2004

Ozonolysis mechanism of lignin model compounds and microbial treatment of organic acids produced.

Treatment methods comprising ozonolysis and microbial treatment of lignin discharged from the pulp manufacture industries were investigated by using a sulfite pulp wastewater and a lignin model compound, i.e. sodium lignosulfonate. Dynamic behaviors for the formations of intermediate derivatives such as muconic acid, maleic acid, and oxalic acid produced from the ozonolysis of sulfite pulp wastewater were observed from data of UV absorption at 280 nm by a spectrophotometer and at 210 nm by high performance liquid chromatography. The microorganisms that were isolated by the enrichment culture method were used to degrade the organic acids such as oxalic acid and acetic acid. Time courses of biological degradation of these organic acids indicated diauxic growth, which was found in a culture with mixed substrates. In the treatment of sodium lignosulfonate, the ozonolysis and microbial treatment using activated sludge converted sodium lignosulfonate into carbon dioxide and water almost completely.

Adsorption↗
PubMed2005

A field experimental study of lignin sand stabilizing material (LSSM) extracted from spent-liquor of straw pulping paper mills.

A new technique was introduced for sand stabilization and re-vegetation by use of lignin sand stabilizing material (LSSM). LSSM is a reconstructed organic compound with lignin as the most dominant component from the extracts of black-liquor issued by straw pulp paper mills. Unlike the polyvinyl acetate or foamed asphalt commonly used for dune stabilization, the new material is plant-friendly and can be used with virescence actions simultaneously. The field experimental study was conducted since 2001 in China's Northwest Ningxia Hui Autonomous Region and has been proved that LSSM is effective in stabilizing the fugitive dunes, making the arenaceous plants survive and the bare dune vegetative. The advisable solution concentration is 2% and the optimal field spraying quantity is 2.5 L/m2. The soil nutrients of the stabilized and greened dune, such as organic matter, available phosphorous and total nitrogen are all increased compared with the control treatment, which is certainly helpful to the growth of arenaceous plants. The technique is worthwhile to be popularized because it is provided not only a new method for desertification control but also an outlet for cleaning contaminants issued from the straw paper mills.

Lignin↗
PubMedDate not supplied

[Degradation of phenols formed during lignin pyrolysis by microfungi of genera Trichoderma and Penicillium].

This work presents the data on the rate of utilization of phenols formed during lignin pyrolysis by micromycetes of the genera Trichoderma and Penicillium. Trichoderma strains utilized phenols at the concentration of liquid pyrolytic products of 0.5-1%, while representatives of Penicillium degraded over 50% phenols at the concentration of pyrolytic products of 2%. Micromycete cultures completely utilized phenol and the cresol-xylenol fraction. Penicillium strains demonstrated a more active growth on media containing phenol, pcresol, or guaiacolic acid as the source of carbon as compared to Trichoderma. m-Cresol and m-xylenol in micromycete growth media containing products of lignin pyrolysis seem to be utilized by co-oxidation.

Biodegradation, Environmental↗
PubMedDate not supplied

[Consumption of water-insoluble phenolic products of lignin pyrolysis by the strain Penicillium tardum H-2].

Abstract-Physiological and biochemical properties of the strain Penicillium tardum H-2, a degrader of phenolic compounds formed during lignin pyrolysis, have been characterized. The micromycete P. tardum H-2 can consume phenol, pyrocatechol, p-cresol, vanillin, and guaiacum resin. When grown in a medium containing the water-soluble fraction of lignin pyrolysis waste at concentrations from 0.5 to 2%, it consumes 62-72% of the phenolic components of the waste. According to gas-liquid chromatography, cultivation of P. tardum H-2 in a medium with liquid pyrolysis products results in a complete consumption of the phenol-cresol fraction.

Benzaldehydes↗