Simple phenolic glycosides as potential regulators of the IAA-oxidase system

The effect of phenols and simple phenolic glycosides on the activity of IAA-oxidase isolated from gherkin seedlings was studied in experimentsin vitro. Phenol stimulated the enzyme system activity, eugenol and quinol were proven as inhibitors. Simple phenolic glycosides (arbutin, gein and phenol glucoside) influenced IAA-oxidase activity only if β-glycosidase was present: rree phenols released from their bound form increased or decreased the IAA level. The potential fegulatory effect of simple phenolic glycosides on the IAA level in plants has been discussed; this effect is thought to be mediated by free phenols and by influence on the IAA-oxidase system.     

植物次生代谢物含量的季节性变化及其对高原鼠兔食物选择的影响

2008 年6 ～9 月在中国科学院海北高寒草甸生态系统定位站通过自助餐式食物选择实验测定了高原鼠兔对20 种植物的取食量,采用紫外可见分光光度计法测定了不同季节20 种植物中黄酮、缩合单宁、简单酚和总酚4种植物次生代谢物的含量,分析了植物次生代谢物含量与高原鼠兔食物选择之间的相互关系。结果表明,在选定的20 种植物中高原鼠兔喜食的植物有7 种,可食的植物有7 种,厌食的植物有6 种。植物次生代谢物的含量在不同的植物间表现出一定的差异,且有生长季节早期含量低,随后逐渐增高的季节性变化趋势。高原鼠兔对植物的选择性与植物中黄酮含量有显著的负相关性,喜食植物的黄酮含量显著低于厌食植物,喜食植物的单宁含量显著小于可食植物,可食植物的单宁含量显著大于厌食植物。在喜食植物中,高原鼠兔取食量与简单酚和总酚含量呈显著负相关性。以上结果部分验证了植物次生代谢物作为植物的防御对策明显影响高原鼠兔对食物选择的假说。黄酮类次生代谢物明显抑制高原鼠兔的取食,缩合单宁对高原鼠兔食物选择也有一定的抑制作用,高原鼠兔有少量取食但避免大量取食简单酚和总酚含量高的植物的选择策略。     

Adsorption of phenol, p-chlorophenol and p-nitrophenol onto functional chitosan

Functional chitosan, chemically modified by salicylaldehyde (CS-SA), beta-cyclodextrin (CS-CD), and a cross-linked beta-cyclodextrin polymer (EPI-CD) were prepared as adsorbents to remove phenol, p-nitrophenol and p-chlorophenol from aqueous solution. Langmuir and Freundlich models were applied to describe the adsorption isotherm of phenols, and adsorption parameters were evaluated. Functional chitosan displayed outstanding adsorption ability for phenols. To our surprise, CS-CD exhibited specific adsorption ability for p-chlorophenol. The possible adsorption interaction was discussed. Effects of pH and KCl on the adsorption suggested that the adsorption of phenols was predominated by hydrogen bonding, hydrophobic interaction and pi-pi interaction not electrostatic interaction. Effect of temperature indicated that the low temperature was favorable for the adsorption of phenols. Separation of phenols and adsorbent regeneration were carried out by simple washing with ethanol and filtrating.     

Identification of Antibacterial Phenolics in Selected Plant Species from Mexican Cloud Forest by Mass Spectrometry Dereplication

Fifteen plant species from a protected cloud forest (CF) in Veracruz, Mexico, were screened for their in vitro capacity to inhibit the growth of the phytopathogenic bacteria Chryseobacterium sp., Pseudomonas cichorii, Pectobacterium carotovorum and Pantoea stewartii, causal agents of damage to crops like ‘chayote’, lettuce, potato and corn. As a result, the bioactivity of Turpinia insignis and Leandra cornoides is reported for the first time against Chryseobacterium sp. and P. cichorii. In addition, 24 and 18 compounds not described for these species were dereplicated by an UPLC/MS‐MS method, respectively. The identified compounds included simple phenols, hydroxycinnamic acids, flavonoids and coumarins. The antibacterial assay of 12 of them demonstrated the bacteriostatic effect of vanillin, trans‐cinnamic acid, scopoletin and umbelliferone against Chryseobacterium sp. These findings confirm for the first time the value of the CF plants from Veracruz as sources of bioactive natural products with antimicrobial properties against phytopathogenic bacteria.     

A chemotaxonomic survey of flavonoids and simple phenols in the leaves of Gaultheria L. and related genera (Ericaceae)

MIDDLETON, D. J., 1992. A chemotaxonomic survey of flavonoids and simple phenols in the leaves of Gaultheria L. and related genera (Ericaceae). Species of Gaultheria and Leucothoe have been screened for a number of flavonoids and simple phenols. Many of these, particularly the American species, are surveyed for the first time. Extensive sampling has also been carried out within some of the species of Gaultheria. Together with previously published data the results are discussed in relation to the position of Gaultheria in the Ericaceae and the infrageneric classification of Gaultheria. The infraspecific variation is commented on.     

Highly efficient and selective methoxymethylation of alcohols and phenols catalyzed by high-valent tin(IV) porphyrin

An efficient and selective method for methoxymethylation of alcohols and phenols with formaldehyde dimethyl acetal (FDMA) catalyzed by electron deficient tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate, [Sn^IV(TPP)(OTf)₂], is reported. A variety of primary, secondary and tertiary alcohols as well as phenols were converted to their corresponding methoxymethyl ethers with FDMA in the presence of a high-valent tin(IV) porphyrin. This catalyst can be used for selective methoxymethylation of primary, secondary and tertiary alcohols in the presence of phenols or tertiary alcohols. The present method offers several advantages such as short reaction times, high yields, simple procedure, selectivity and applicability for both alcohols and phenols.     

Relationship between cytostatic activity of oxazolopyridocarbazoles and accessibility of DNA intercalation sites in living bacteria

The ability of oxazolopyridocarbazole (OPC) derivatives to interact with DNA in living bacteria through reversible intercalation has been determined by using as probes their selective mutagenic effect on Salmonella typhimurium TA 1977 and TA 1537 as detected by frame-shift-1 reversion, the absence of intervention of the error-prone repair system on the mutagenic efficiency, the absence of induction of the SOS functions, and the absence of effect of recA and uvrB mutations on their bacteriostatic properties. Involvement of simple reversible intercalation as the event responsible for the bacteriostatic effect of the drugs has been further investigated by the establishment of a significant correlation between the maximum number of accessible intercalating sites in living bacteria and the bacteriostatic effect expressed in terms of the ED50. This correlation has been established by using bacteria spontaneously exhibiting different sensitivities toward the drugs as well as a resistant strain obtained by adaptation in the presence of increasing amounts of isopropyl-OPC. The number of intercalating sites in living bacteria was determined by using the change in the fluorescence properties of the drugs upon binding to intercalating sites. The results obtained clearly demonstrate that the number of intercalating sites is the parameter that controls the bacteriostatic effect of the drugs, indicating that DNA is the target for these drugs and that reversible intercalation is responsible for the cytostatic effect.     

Demonstration of phenolic compounds in plant tissues by an osmium-iodide postfixation procedure

A simple procedure to stain phenols in plant tissues is described. Postfixation with an aqueous solution prepared by mixing 2 cc of 2% osmium tetroxide and 8 cc of 3% potassium iodide yields brilliant visualization of phenol-containing vacuoles in different tissues of plants (e.g., coffee, oak, tobacco and spruce) bearing high concentration of phenolic compounds. Areas bearing phenols become dark gray to black. Chemical experiments demonstrate that osmium-potassium iodide (Os-KI) mixture reacts rapidly with several naturally occurring plant phenols, developing black solutions from which black solids precipitate. Phenols containing omicron-dihydroxy groups react with Os-KI solution more rapidly than other structurally different phenols. Therefore, omicron-dihydroxy units in an aromatic ring seem to function as primary sites of reactivity with the osmium-iodide complexes.     

Aryl sulfotransferase IV from rat liver

A group of aryl sulfotransferases has been identified that catalyzes sulfate ester formation with simple phenols at an acidic pH and with several physiological metabolites at a more alkaline pH. One enzyme, aryl sulfotransferase IV, has been purified to homogeneity and found to be a protein of 61,000 daltons composed of two subunits of apparent equal size. Homogeneous preparations are active with simple phenols, organic hydroxylamines, and catecholamines as well as serotonin and its metabolites. The enzyme is also active with tyrosine methyl ester and with those peptide hormones e.g., cholecystokinin heptapeptide and some of the enkephalins, which have N-terminal tyrosine residues.     

Demonstration of Phenolic Compounds in Plant Tissues by An Osmium-Iodide Postfixation Procedure

A simple procedure to stain phenols in plant tissues is described, Postfixation with an aqueous solution prepared by mixing 2 cc of 2% osmium tetroxide and 8 cc of 3% potassium iodide yields brilliant visualization of phenol-containing vacuoles in different tissues of plants (e.g. coffee, oak, tobacco and spruce) bearing high concentration of phenolic compounds. Areas bearing phenols become dark gray to black. Chemical experiments demonstrate that osmium-potassium iodide (Os-KI) mixture reacts rapidly with several naturally occurring plant phenols, developing black solutions from which black solids precipitate. Phenols containing o-dihydroxy groups react with Os-KI solution more rapidly than other structurally different phenols. Therefore, o-dihydroxy units in an aromatic ring seem to function as primary sites of reactivity with the osmium-iodide complexes.     

Antibacterial activity of sphagnum acid and other phenolic compounds found in Sphagnum papillosum against food-borne bacteria

Aims:  To identify the phenolic compounds in the leaves of Sphagnum papillosum and examine their antibacterial activity at pH appropriate for the undissociated forms.
Methods and Results:  Bacterial counts of overnight cultures showed that whilst growth of Staphylococcus aureus 50084 was impaired in the presence of milled leaves, the phenol-free fraction of holocellulose of S. papillosum had no bacteriostatic effect. Liquid chromatography–mass spectrometry analysis of an acetone–methanol extract of the leaves detected eight phenolic compounds. Antibacterial activity of the four dominating phenols specific to Sphagnum leaves, when assessed in vitro as minimal inhibitory concentrations (MICs), were generally >2·5 mg ml⁻¹. MIC values of the Sphagnum- specific compound 'sphagnum acid' [ p -hydroxy-β-(carboxymethyl)-cinnamic acid] were >5 mg ml⁻¹. No synergistic or antagonistic effects of the four dominating phenols were detected in plate assays.
Conclusions:  Sphagnum -derived phenolics exhibit antibacterial activity in vitro only at concentrations far in excess of those found in the leaves.
Significance and Impact of the Study:  We have both identified the phenolic compounds in S. papillosum and assessed their antibacterial activity. Our data indicate that phenolic compounds in isolation are not potent antibacterial agents and we question their potency against food-borne pathogens.     

Separation of the eleven priority pollutant phenols by capillary zone electrophoresis

Capillary zone electrophoresis (CZE) provides highly efficient separation of the eleven US EPA priority pollutant phenols. All of these phenols are completely resolved in fewer than 15 min in a 100 cm × 75 μm I.D. uncoated fused-silica capillary at 22.5 kV using a pH 9.8 phosphate-borate buffer. Buffer pH is the most critical parameter controlling resolution and separation time. A simple theoretical treatment greatly simplifies the pH optimization procedure. The effects on the separation of buffer concentration, applied voltage, and sample quantity injected were studied. Good calibration data were obtained for phenol concentrations up to 50 mb/l. Limits of detection for all phenols were less than 1 ppm.     

Enzymatic total synthesis of enterocin polyketides

Polyketides are clinically important natural products that often require elaborate organic syntheses owing to their complex chemical structures. Here we report the multienzyme total synthesis of the Streptomyces maritimus enterocin and wailupemycin bacteriostatic agents in a single reaction vessel from simple benzoate and malonate substrates. To our knowledge, our results represent the first in vitro assembly of a complete type II polyketide synthase enzymatic pathway to natural products.     

Halide and Alkyl Phenols Block Volume-Sensitive Chloride Channels in Human Glial Cells (U-138MG)

Swelling of cells in hypotonic media activates a volume-sensitive Cl channel with well-known characteristics, but its structure and its regulation are still largely undetermined. It also has many inhibitors and most of them are also blocking other types of Cl channels. The numerous inhibitors of Cl channels have apparently no structural relationship among them. The purpose of this study was to try to determine the most simple molecules that could block these channels and identify some common properties among inhibitors. From the 37 new molecules that were studied, it was found that simple halide phenols like trichloro and triiodophenols could block these channels in the micromolar range. Also alkyl phenols, like butylphenols, are very sensitive blockers, comparable to other well-known blockers. But acidic halide phenols or nitrophenols are poor blockers. Also neutral polyphenols are more sensitive than acidic polyphenols. All these results indicate that the common basis for blocking these Cl channels is a phenol with hydrophobic groups, like short alkyl chains or an additional phenyl ring, attached to some of its sites, preferably sites 3-4-5. These results identify a new family of Cl channel blockers and hopefully improve our understanding of the blocking mechanism. Received: 28 August 1997/Revised: 12 December 1997     

效应面法优化石榴皮抑菌物的提取工艺

采用单因素和效应面法对石榴皮抑菌物提取条件进行优化,并对结果进行验证。结果发现:最佳提取温度为59℃、时间为73 min、液料比为40∶1(mL/g)。实验证明石榴皮提取物对枯草杆菌具有很强的抑制作用,且所用工艺简单易行,说明效应面优化法建立的数学模型预测结果可靠。     

Determination of phenolic compounds by a polyphenol oxidase amperometric biosensor and artificial neural network analysis

The determination of phenolic compounds is significant given its toxicity, even at very low concentration levels. Amperometric determination of phenols is a simple technique available. Direct oxidation of phenols can be used, but another possibility is the use of polyphenol oxidase (tyrosinase) enzyme biosensors that oxidises the phenolic compounds into their corresponding quinones. Reduction of the resulting quinones accomplishes the amplification of the amperometric signal, as long as the result of the reduction process is the corresponding cathecol, this being able to be oxidised again by the polyphenol oxidase immobilized on the surface of the biosensor. In this communication, simultaneous determination of different phenols was carried out combining biosensor measurements with chemometric tools, in what is known as electronic tongue. The departure information used was the overlapped reduction voltammogram generated with the amperometric biosensor based on polyphenol oxidase. Artificial Neural Networks (ANN) were used for extraction and quantification of each compound. Phenol, cathecol and m-cresol formed the three-analyte study case resolved in this work. Good prediction ability was attained, and so, the separate quantification of these three phenols was accomplished.     

有抑菌能力乳杆菌的筛选及其抑菌物质的初步探究

目的 筛选具有抑菌能力的乳杆菌菌株并对其抑菌物质进行初步探究。方法 采用琼脂扩散法进行抑菌试验,筛选出具有抑菌能力的乳杆菌菌株;通过热稳定性试验检测抑菌物质耐高温的能力;通过有机酸排除与过氧化氢排除试验检测这两种物质对抑菌作用是否有影响;用胃蛋白酶、胰蛋白酶和蛋白酶K消化处理各株乳杆菌无细胞发酵液后进行抑菌试验,判断抑菌物质是否为蛋白多肽类物质。结果 2株副干酪乳杆菌与1株保加利亚乳杆菌对大肠埃希菌、铜绿假单胞菌、伤寒沙门菌和痢疾志贺菌有抑菌效果。这3株乳杆菌无细胞发酵液中的抑菌物质经过高温处理后仍具有抑菌能力,但抑菌能力与处理前相比显著降低（P＜0.05）;有机酸对照组未产生明显的抑菌圈;过氧化氢排除后的无细胞发酵液的抑菌能力未受影响;经过蛋白酶作用3株乳杆菌无细胞发酵液的抑菌能力显著降低（P＜0.05）或消失。生物被膜态副干酪乳杆菌2的抑菌能力与浮游态相近,其无细胞发酵液中的抑菌物质可以完全耐受100℃处理与胃蛋白酶的消化作用,可部分耐受胰蛋白酶的消化作用。结论 副干酪乳杆菌1、副干酪乳杆菌2和保加利亚乳杆菌具有良好的抑菌能力,它们产生的主要抑菌物质为蛋白多肽类,此物质具有较好的耐高温能力与耐蛋白酶能力;被膜态副干酪乳杆菌产生的抑菌物质表现出了更强的抗胁迫能力与稳定性。     

Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids

Ten esters each of caffeic acid and dihydrocaffeic acid have recently been synthesized. Cytotoxicity evaluations of these esters versus L1210 leukemia and MCF-7 breast cancer cells in culture have led to the delineation of substantially different QSAR for each series. The L1210 QSAR for dihydrocaffeic acid esters resembles the QSAR obtained for simple phenols and estrogenic phenols. However, the QSAR pertaining to the caffeic acid esters differs considerably from its sister QSAR. This difference may be attributed to the presence of the olefinic linkage in the side chain. The octyl ester of caffeic acid is nearly ten times as toxic to the leukemia cells than the widely studied phenethyl ester, CAPE.     

20种药用蕨类植物提取液抑菌试验研究

以20种药用蕨类植物提取液对金黄色葡萄球菌、大肠杆菌、八叠球菌、变形杆菌、枯草杆菌、酵母菌进行抑菌活性研究,结果表明,20种蕨类提取液至少对一种供试微生物具有抑菌活性。样品蕨类醇提液比水提液具更强的抑菌活性,供试菌有阳性结果的水提液,平均抑菌圈直径10.12mm,而醇提液则为11.92mm。试验结果还表明,药用蕨类对枯草杆菌抗菌活性效果最明显,对酵母菌效果最差。不同蕨类植物其地上部分和地下部分抑菌效果不尽相同。     

Relation of the antimutagenic activity of simple phenols to the number of hydroxyl groups

The influence of mono-phenol, di-resorcinol and tri-pyrogallol hydroxyl groups of simple unsubstituted phenols on the mutagenic potentials of benzo(a)pyrene was studied in vivo (micronuclear test on bone marrow polychromatic erythrocytes) and in vitro (test of direct point mutations at V79/HGPRT system induced by metabolic activation by mouse liver microsomal enzymes). The phenols decreased the mutagenic activity of benzo(a)pyrene in in vivo tests, with pyrogallol being the most active, it followed by resorcinol and phenol. The mixtures of benzo(a) pyrene + pyrogallol and benzo(a)pyrene + resorcinol were significantly less mutagenic in in vitro tests than benzo(a)pyrene and benzo(a)pyrene + phenol.