Microbial Metabolism of Quinoline and Related Compounds. XIX. Degradation of 4-Methylquinoline and Quinoline by<i>Pseudomonas putida</i>K1

Rüger, Anja; Schwarz, Gerhild; Lingens, Franz

doi:10.1515/bchm3.1993.374.7-12.479

Cited by 24 publications

(16 citation statements)

References 13 publications

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“…A recent study reports that the coumarin-based oral anti-coagulants such as phenprocouman (Marcumar), caused the hepatotoxicity leading to acute liver failure [60]. [63]. Another pathway involving the initial cleavage of the lactam ring was also found in Pseudomonas stutzeri [64].…”

Section: Metabolismmentioning

confidence: 99%

Recent Advances in Coumarins and 1-Azacoumarins as Versatile Biodynamic Agents

Kulkarni¹,

Kulkarni²,

Chao³

et al. 2006

CMC

222

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Coumarins, also referred as benzopyran-2-ones, and their corresponding nitrogen counterpart, 1-azacoumarins also referred to as carbostyrils, are a family of nature-occurring lactones and lactams respectively. The plant extracts containing coumarin-related heterocycles, which were employed as herbal remedies in early days, have now been extensively studied for their biological activities. These investigations have revealed their potentials as versatile biodynamic agents. For example, coumarins with phenolic hydroxyl groups have the ability to scavenge reactive oxygen species and thus prevent the formation of 5-HETE and HHT in the arachidonic pathway of inflammation suppression. Recent in vivo studies have revealed the role of coumarins in hepatotoxicity and also in depletion of cytochrome P450. Similarly 1-azacoumarins which is part of quinoline alkaloids, are known for their diverse biological activity and recently, a 6-functionalized 1-aza coumarins are undergoing human clinical trials as an orally active anti-tumor drug in view of its farnesyl protein-inhibiting activity in the nanomolar range. Furthermore, several synthetic coumarins with a variety of pharmacophoric groups at C-3, C-4 and C-7 positions have been intensively screened for anti-microbial, anti-HIV, anti-cancer, lipid-lowering, anti-oxidant, and anti-coagulation activities. Specifically, coumarin-3-sulfonamides and carboxamides were reported to exhibit selective cytotoxicity against mammalian cancer cell lines. The C4-substituted aryloxymethyl, arylaminomethyl, and dichloroacetamidomethyl coumarins, along with the corresponding 1-azacoumarins, have been demonstrated to be potential anti-microbial and anti-inflammatory agents. To expand the structural diversity of synthetic courmarins for biological functions, attempts have also been made to attach a chloramphenicol side chain at C-3 position of courmarin. In addition, the bi- and tri-heterocyclic coumarins and 1-azacoumarins with benzofuran, furan and thiazole ring systems along with biocompatible fragments like vanillin have shown remarkable potency as anti-inflammatory agents in animal models. Photobiological studies on pyridine-fused polycyclic coumarins have highlighted their potential as thymine dimer photosensitisers and the structurally related compounds of both coumarin and carbostyrils have also been found to act via the DNA gyrase pathway in their anti-bacterial activity. Apart from the above works, the present review also addresses the potential roles of coumarins and carbostyrils as protease inhibitors, or fluorescent probes in mechanistic investigation of biochemical pathways, and their application for QSAR in theoretical studies. Though 1-Azacoumarins have received less attention as compared to coumarins in the literature, an attempt has been made to compare both the systems at various stages, so that it can spark new thoughts on synthetic methodologies, reactivity pattern and biological activities.

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Section: Metabolismmentioning

confidence: 99%

Recent Advances in Coumarins and 1-Azacoumarins as Versatile Biodynamic Agents

Kulkarni¹,

Kulkarni²,

Chao³

et al. 2006

CMC

222

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“…[24] 5,6-Dihydroxy-1H-2-oxoquinoline (18) presumably also is an intermediate in the degradation of quinoline (10) by Comamonas testosteroni 63, [25] Pseudomonas putida K1, [26] Rhodococcus sp. B1, [21] a Moraxella sp., [27] and perhaps a Nocardia sp.…”

Section: 6-dihydroxy-1h-2-oxoquinoline Pathwaymentioning

confidence: 99%

“…[24] c) 7,8-Dihydroxy-1H-2-oxoquinoline pathway: degradation of 4-methylquinoline by Pseudomonas putida K1. [26] d) 8-Hydroxycoumarin pathway: degradation of quinoline (10) by Pseudomonas putida 86, [21] Pseudomonas fluorescens 3, [21] Pseudomonas stutzeri, and Pseudomonas pseudoalcaligenes. [32] Scheme 2.…”

Section: Reviewsmentioning

confidence: 99%

Bacterial Degradation of Quinoline and Derivatives—Pathways and Their Biocatalysts

Fetzner

Tshisuaka

Lingens

et al. 1998

Angewandte Chemie International Edition

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A series of interesting enzymes were discovered during investigations on the degradation of quinoline by microorganisms. These include the molybdenum-containing hydroxylases that catalyze the transformation 1→2 and the unusual 2,4-dioxygenases that catalyze the reaction 3→4. The application of the hydroxylases may even be interesting in industry, because several quinoline derivatives are used as pharmaceuticals or agrochemicals.

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“…Wir nehmen an, daû bei dieser Verbindung der Benzolring gespalten wird, denn es gelang, das N-heterocyclische Zwischenprodukt 3-Methyl-2,5,6-trihydroxypyridin 21 zu isolieren. [24] Vermutlich ist auch 5,6-Dihydroxy-1H-2oxochinolin 18 ein Metabolit von Chinolin 10 bei Comamonas testosteroni 63, [25] Pseudomonas putida K 1, [26] Rhodococcus sp. B 1, [21] Moraxella sp.…”

Section: Der 56-dihydroxy-1h-2-oxochinolin-abbauwegunclassified

“…Der 7,8-Dihydroxy-1H-2-oxochinolin-Abbauweg ¾hnlich dem in Abschnitt 2.3 beschriebenen Abbauweg verläuft auch der 7,8-Dihydroxy-1H-2-oxochinolin-Weg über ein ortho-Dihydroxybenzol-Derivat, bei dem wahrscheinlich der Benzolring gespalten wird. 7,8-Dihydroxy-1H-2-oxochinoline sind Schlüsselverbindungen, die beim Abbau von 4-Methylchinolin 22 durch Pseudomonas putida K 1 [26] (Schema 1 c), von 4-Hydroxychinolin durch ein Bodenbakterium der Gruppe Pseudomonas [29] und beim Abbau von Kynurensäure [30,31] entstehen. Das 8-Monohydroxyderivat 24 von 1H-4-Methyl-2-oxochinolin 23 wurde zwar als Metabolit in sauren Extrakten der Kulturbrühe von Pseudomonas putida K 1 entdeckt, [26] …”

Section: Der 56-dihydroxy-1h-2-oxochinolin-abbauwegunclassified