The Determination and Excretion of Polyhydroxy (Catecholic) Phenolic Acids in Urine

Sl, Tompsett

doi:10.1111/j.2042-7158.1958.tb10286.x

Cited by 22 publications

(3 citation statements)

References 6 publications

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“…Decarboxylation of 2,4-D in plant tissue has been reported by Fellig (1959, 1961), Cunny and Markus (i 960 ), Weintraub et al (1952), and many others. Tompsett (1958) indicated that gallic acid was decarboxylated to pyrogallol in human urine. Pyrogallol was also detected in the urine of rats by Booth et al (1959) when they injected gallic acid intraperitoneally.…”

Section: Benzoic Acid Metabolismmentioning

confidence: 99%

Chemical control of nutsedge (Cyperus rotundus L.) and the metabolism of 3,6-dichloro-O-anisei acid (dicamba) /

Ray¹

1967

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REVIEW OF LITERATURE Nutsedge and Its Control Nutsedge is one of the most persistent weeds in croplands and is very often a serious pest in vegetable crops and in nursery stocks. This weed not only causes reduction in yield through competition for water and minerals in the soil, but also increases the cost of cultivation and lowers crop quality. It is also a problem in lawns, where it spoils the appearance of the turf. Bell et al. (1962) pointed out that nutsedge rhizomes grew through potato tubers, thus increasing the proportion of culls. Nutsedge tubers were also found to pass through bean-shelling equipment, necessitating hand sorting. Although nutsedge is a native of Asia, it is distributed widely in all warm regions and is found in Africa, Australia, and in the warmer parts of Europe. The plant is adaptable to a wide variety of soils and environmental conditions in tropical or subtropical regions (Muenscher, 1955)* In the United States, it is found from Virginia to Florida, Kansas, and Texas. Yellow nutsedge (Cyperus esculentus L.

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Section: Benzoic Acid Metabolismmentioning

confidence: 99%

Chemical control of nutsedge (Cyperus rotundus L.) and the metabolism of 3,6-dichloro-O-anisei acid (dicamba) /

Ray¹

1967

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“…The ileum was chosen for further study because it had consistently high pyrogallol production, making it a more suitable choice for further experimentation. Additionally, gastrointestinal metabolism and absorption of gallotannins and pyrogallol has been demonstrated as a pathway for tannin-induced toxicosis in monogastric animals, 5,12,24 which supports the decision to choose the ileum for further study rather than the liver.…”

mentioning

confidence: 99%

“…7 More work is needed to determine the complete pathophysiology, absorption, and sites of metabolism of gallotannins in monogastric organisms. 5,12,24 The recent isolation of the tannase enzyme (the enzyme catalyzing the first step in the proposed pathway) from E. cloacae and K. pneumoniae 22,23 could be important in the development of effective treatment options for red maple toxicosis, possibly including antimicrobials and drugs that inhibit intestinal absorption of pyrogallol. …”

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confidence: 99%

Identification of protoxins and a microbial basis for red maple (Acer rubrum) toxicosis in equines

et al. 2012

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Abstract. The leaves of Acer rubrum (red maple), especially when wilted in the fall, cause severe oxidative damage to equine erythrocytes, leading to potentially fatal methemoglobinemia and hemolytic anemia. Gallic acid and tannins from A. rubrum leaves have been implicated as the toxic compounds responsible for red maple toxicosis, but the mechanism of action and toxic principle(s) have not been elucidated to date. In order to investigate further how red maple toxicosis occurs, aqueous solutions of gallic acid, tannic acid, and ground dried A. rubrum leaves were incubated with contents of equine ileum, jejunum, cecum, colon, and liver, and then analyzed for the metabolite pyrogallol, as pyrogallol is a more potent oxidizing agent. Gallic acid was observed to be metabolized to pyrogallol maximally in equine ileum contents in the first 24 hr. Incubation of tannic acid and A. rubrum leaves, individually with ileum contents, produced gallic acid and, subsequently, pyrogallol. Ileum suspensions, when passed through a filter to exclude microbes but not enzymes, formed no pyrogallol, suggesting a microbial basis to the pathway. Bacteria isolated from ileum capable of pyrogallol formation were identified as Klebsiella pneumoniae and Enterobacter cloacae. Therefore, gallotannins and free gallic acid are present in A. rubrum leaves and can be metabolized by K. pneumoniae and E. cloacae found in the equine ileum to form pyrogallol either directly or through a gallic acid intermediate (gallotannins). Identification of these compounds and their physiological effects is necessary for the development of effective treatments for red maple toxicosis in equines.

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Phenol and Phenolics

Cavender,

O'Donoghue

2023

Patty's Toxicology

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The phenolics used for industrial and commercial purposes are a large and diverse group of chemicals as the six‐member ring of phenolics can be methylated, halogenated or include other moieties that add properties or toxicological potential that is not observed with simple phenolics. For simple dihydroxy phenolics, the largest exposure potential can be through their presence naturally in foods. Low concentrations of chlorophenols are commonly found in drinking water due to water chlorination processes. Simple methyl phenols are commonly used as disinfectants. More complex phenolics such as creosote and pentachlorophenol are used as wood preservatives. The acute toxicity of phenolics at relatively high doses is manifested as excitation of the nervous system causing muscle tremors, salivation, and in severe cases, convulsions. The excitatory phase of phenolic intoxication gives way to depression of the nervous system and can result in mortality. Acute and repetitive exposure to phenolics can result in liver and kidney toxicity. A number of phenolics can be absorbed through skin and are readily absorbed after ingestion. Major metabolites of phenols are sulfates and glucuronide conjugates that are excreted through the kidneys. First pass metabolism present on ingestion is not a factor for phenols absorbed through the skin. Therefore, the toxicity of phenolics may differ depending on route of exposure.

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The Determination and Excretion of Polyhydroxy (Catecholic) Phenolic Acids in Urine

Cited by 22 publications

References 6 publications

Chemical control of nutsedge (Cyperus rotundus L.) and the metabolism of 3,6-dichloro-O-anisei acid (dicamba) /

Chemical control of nutsedge (Cyperus rotundus L.) and the metabolism of 3,6-dichloro-O-anisei acid (dicamba) /

Identification of protoxins and a microbial basis for red maple (Acer rubrum) toxicosis in equines

Phenol and Phenolics

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