Sample records for 1,2,3-trihydroxybenzene

  1. Oxidation of benzene to phenol, catechol, and 1,2,3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1. (United States)

    Tao, Ying; Fishman, Ayelet; Bentley, William E; Wood, Thomas K


    Aromatic hydroxylations are important bacterial metabolic processes but are difficult to perform using traditional chemical synthesis, so to use a biological catalyst to convert the priority pollutant benzene into industrially relevant intermediates, benzene oxidation was investigated. It was discovered that toluene 4-monooxygenase (T4MO) of Pseudomonas mendocina KR1, toluene 3-monooxygenase (T3MO) of Ralstonia pickettii PKO1, and toluene ortho-monooxygenase (TOM) of Burkholderia cepacia G4 convert benzene to phenol, catechol, and 1,2,3-trihydroxybenzene by successive hydroxylations. At a concentration of 165 microM and under the control of a constitutive lac promoter, Escherichia coli TG1/pBS(Kan)T4MO expressing T4MO formed phenol from benzene at 19 +/- 1.6 nmol/min/mg of protein, catechol from phenol at 13.6 +/- 0.3 nmol/min/mg of protein, and 1,2,3-trihydroxybenzene from catechol at 2.5 +/- 0.5nmol/min/mg of protein. The catechol and 1,2,3-trihydroxybenzene products were identified by both high-pressure liquid chromatography and mass spectrometry. When analogous plasmid constructs were used, E. coli TG1/pBS(Kan)T3MO expressing T3MO formed phenol, catechol, and 1,2,3-trihydroxybenzene at rates of 3 +/- 1, 3.1 +/- 0.3, and 0.26 +/- 0.09 nmol/min/mg of protein, respectively, and E. coli TG1/pBS(Kan)TOM expressing TOM formed 1,2,3-trihydroxybenzene at a rate of 1.7 +/- 0.3 nmol/min/mg of protein (phenol and catechol formation rates were 0.89 +/- 0.07 and 1.5 +/- 0.3 nmol/min/mg of protein, respectively). Hence, the rates of synthesis of catechol by both T3MO and T4MO and the 1,2,3-trihydroxybenzene formation rate by TOM were found to be comparable to the rates of oxidation of the natural substrate toluene for these enzymes (10.0 +/- 0.8, 4.0 +/- 0.6, and 2.4 +/- 0.3 nmol/min/mg of protein for T4MO, T3MO, and TOM, respectively, at a toluene concentration of 165 microM). PMID:15240250

  2. A new shortcut synthesis route for (±)raphidecursinol

    Institute of Scientific and Technical Information of China (English)


    The new shortcut synthesis route of(±)raphidecursinol 1,a racemic 8,4′-oxyneolignan compound,can be more easily achieved by the synthesis route,starting from readily available inexpensive 3,4,5-trimethoxybenzaldehyde and 1,2,3-trihydroxybenzene.All structures were confirmed by ~1H NMR,IR and MS.

  3. Evolution of novel O-methyltransferases from the Vanilla planifolia caffeic acid O-methyltransferase. (United States)

    Li, Huaijun Michael; Rotter, David; Hartman, Thomas G; Pak, Fulya E; Havkin-Frenkel, Daphna; Belanger, Faith C


    The biosynthesis of many plant secondary compounds involves the methylation of one or more hydroxyl groups, catalyzed by O-methyltransferases (OMTs). Here, we report the characterization of two OMTs, Van OMT-2 and Van OMT-3, from the orchid Vanilla planifolia Andrews. These enzymes catalyze the methylation of a single outer hydroxyl group in substrates possessing a 1,2,3-trihydroxybenzene moiety, such as methyl gallate and myricetin. This is a substrate requirement not previously reported for any OMTs. Based on sequence analysis these enzymes are most similar to caffeic acid O-methyltransferases (COMTs), but they have negligible activity with typical COMT substrates. Seven of 12 conserved substrate-binding residues in COMTs are altered in Van OMT-2 and Van OMT-3. Phylogenetic analysis of the sequences suggests that Van OMT-2 and Van OMT-3 evolved from the V. planifolia COMT. These V. planifolia OMTs are new instances of COMT-like enzymes with novel substrate preferences.

  4. Essential Structural Requirements and Additive Effects for Flavonoids to Scavenge Methylglyoxal. (United States)

    Shao, Xi; Chen, Huadong; Zhu, Yingdong; Sedighi, Rashin; Ho, Chi-Tang; Sang, Shengmin


    Reactive dicarbonyl species, such as methylglyoxal (MGO), are considered as the major precursors of advanced glycation end products (AGEs), which are believed to be one of the physiological causes of diabetes and its complications. Scavenging of reactive dicarbonyl species using naturally occurring flavonoids has been proposed as an effective way to prevent diabetic complications. To elucidate the structural requirements of flavonoids in scavenging MGO, seven flavonoids (quercetin, luteolin, epicatechin, genistein, daidzein, apigenin, and phloretin) and five sub-components of the flavonoids (gallic acid, phloroglucinol, pyrogallol, pyrocatechol, and resorcinol) were examined in this study. Our results showed the following: (1) 1,2,3-trihydroxybenzene (pyrogallol) has higher MGO scavenging activity than 1,3,5-trihydroxybenzene and 1,2- and 1,3-dihydroxybenzene, and substitution at position 5 of pyrogallol diminished the scavenging activity, indicating that position 5 is the active site of pyrogallol; (2) the A ring is the active site of flavonoids in contributing the MGO-trapping efficacy, and the hydroxyl group at C-5 on the A ring enhances the trapping efficacy; (3) the double bond between C-2 and C-3 on the C ring could facilitate the trapping efficacy; and (4) the number of hydroxyl groups on the B ring does not significantly influence the trapping efficacy. In addition, we found there is an additive effect in MGO trapping by two common flavonoids, quercetin and phloretin, indicating that flavonoid-enriched foods and beverages hold great promise to prevent the development of diabetic complications.

  5. Detection, identification and formation of new iodinated disinfection byproducts in chlorinated saline wastewater effluents. (United States)

    Gong, Tingting; Zhang, Xiangru


    The use of seawater for toilet flushing introduces high levels of inorganic ions, including iodide ions, into a city's wastewater treatment systems, resulting in saline wastewater effluents. Chlorination is widely used in disinfecting wastewater effluents owing to its low cost and high efficiency. During chlorination of saline wastewater effluents, iodide may be oxidized to hypoiodous acid, which may further react with effluent organic matter to form iodinated disinfection byproducts (DBPs). Iodinated DBPs show significantly higher toxicity than their brominated and chlorinated analogues and thus have been drawing increasing concerns. In this study, polar iodinated DBPs were detected in chlorinated saline wastewater effluents using a novel precursor ion scan method. The major polar iodinated DBPs were identified and quantified, and their organic precursors and formation pathways were investigated. The formation of iodinated DBPs under different chlorine doses and contact times was also studied. The results indicated that a few polar iodinated DBPs were generated in the chlorinated saline primary effluent, but few were generated in the chlorinated saline secondary effluent. Several major polar iodinated DBPs in the chlorinated saline primary effluent were proposed with structures, among which a new group of polar iodinated DBPs, iodo-trihydroxybenzenesulfonic acids, were identified and quantified. The organic precursors of this new group of DBPs were found to be 4-hydroxybenzenesulfonic acid and 1,2,3-trihydroxybenzene, and the formation pathways of these new DBPs were tentatively proposed. Both chlorine dose and contact time affected the formation of iodinated DBPs in the chlorinated saline wastewater effluents.

  6. Study on effects of lead on the antioxidant activities of Aloe vera%铅污染对芦荟抗氧化活性影响的研究

    Institute of Scientific and Technical Information of China (English)

    蔡卓; 卢登峰; 梁信源; 莫创荣; 杜良伟; 莫利书; 黄富嵘


    The variation of the antioxidant enzyme system of Aloe vera under the stress of different Pb concentrations was studied using pot experiments. The scavenging abilities of the potted Aloe vera to ·OH and O2- o were determined by flow injection chemiluminescence method using methylene blue-Fenton system and 1,2,3 -trihydroxybenzene system. The effects of lead pollution on the enzymatic activity of Aloe vera were evaluated. The results showed that at a relatively low lead pollution level, the enzymatic activity of polluted Aloe vera was higher than that of the un-polluted, and increased with the increase of lead concentration in Aloe vera body; while at a relatively higher lead pollution level, the enzymatic activity of polluted Aloe vera was lower than that of the un-polluted, and the activity decreased with the increase of lead concentration in Aloe vera body. These indicated that at a low pollution level the physiological response of Aloe vera antioxidant enzyme system to heavy metal stress resulted in the rise of enzymatic activity of Aloe vera; while at a high pollution level, the self protection system of Aloe vera is damaged, which in turn led to the damage of antioxidant enzyme system, and then results in the decrease of the enzymatic activity.%采用盆栽试验,对芦荟在不同浓度Pb胁迫下抗氧化酶系统的变化进行了研究.用流动注射化学发光分析法,以亚甲基蓝-Fenton体系、鲁米诺-邻苯三酚体系分别测定盆栽芦荟体内抗氧化酶清除·OH和清除O2-·的能力,进而评价铅污染对芦荟生物活性的影响.结果表明,在相对低浓度铅污染水平下,芦荟提取酶的活性均比无污染时的对照值有所升高,并与芦荟体内铅含量成正相关;而在相对较高浓度铅污染下,提取酶的活性均比对照值有所下降,与芦荟体内铅含量成负相关.说明在低浓度铅毒害作用下,芦荟体内抗氧化酶系统对重金属胁迫的生理的响应使其活性有所上升