Quinoline, quinazoline and acridonealkaloids

Michael, Joseph P.

doi:10.1039/b612168n

Cited by 1,125 publications

(297 citation statements)

References 107 publications

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“…However, only a few single reports deal with quinazolines as secondary metabolites of microorganisms. 13,14 In this study, cultivation, isolation, structural elucidation, crystal structure and biological activity of 1 are presented. Feeding experiments allow for insights into the unusual biosynthetic pathway of microbial quinazoline 1.…”

Section: Introductionmentioning

confidence: 99%

A comprehensive view on 4-methyl-2-quinazolinamine, a new microbial alkaloid from Streptomyces of TCM plant origin

et al. 2009

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In the course of our chemical and biological screening program for yet unidentified microbial metabolites, we selected plants of Traditional Chinese Medicine (TCM) as habitats for talented Streptomycetes producer strains for the first time. Liquid pure cultures of strain Streptomyces sp. GS DV232 were found to contain 4-methyl-2-quinazolinamine (1), a potent alkaloid yet unknown from nature. In this study, we investigated the chemical and crystal structure of 1, as well as its antiproliferative bioactivity, and addressed the unusual biosynthesis using feeding experiments.

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Section: Introductionmentioning

confidence: 99%

A comprehensive view on 4-methyl-2-quinazolinamine, a new microbial alkaloid from Streptomyces of TCM plant origin

et al. 2009

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“…Mp: 207-209 °C. 1 7H-pyrrolo[1,2-b][1,2,4]benzothiadiazine-5,5-dioxide (8b). 1.00 g (4.162 mmol) of 7b was dissolved in 20 ml of phosphoryl chloride (POCl 3 ) and a catalytic amount (2 drops) of dimethylformamide (DMF) was added to the solution.…”

Section: 13-dihydro-7h-indolo[2'3':34]pyrido[12-b]benzothiadiazimentioning

confidence: 99%

“…1 Traditional Chinese medicine has a unique position among traditional medicines as it provides new and safer bioactive lead structures with antitumour activity. 2 Rutaecarpine-type alkaloids form an important class of indolopyridoquinazolinone heterocycles and belong to the subgroup of quinazoline-type alkaloids isolated from the heartwood and the fruit of numerous plants and trees of the Rutaceae family.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of bioisosteric 5-sulfa-rutaecarpine derivatives

Bubenyák¹,

Takacs²,

Blazics³

et al. 2010

Arkivoc

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Rutaecarpine (Evodia rutaecarpa) derivatives were synthesized by bioisosteric replacements of the quinazolone moiety of the pentacyclic system with benzothiadiazine 1,1-dioxide. Syntheses were performed efficiently by formation of phenylhydrazones via active methylene group transformations of pyrrolo-and pyrido[1,2-b]1,2,4-benzothiadiazine 5,5-dioxides, and subsequent Fischer-indolization. Preliminary testing of compound 3 showed cytotoxic activity against HeLa cells and apoptosis inducing effect.

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“…are produced by a variety of higher organisms, especially by plants of the family Rutaceae (2,29,30). Therefore, it is well conceivable that soil microorganisms have evolved enzymes and pathways to detoxify and/or to degrade quinolones.…”

mentioning

confidence: 99%

Conversion of the Pseudomonas aeruginosa Quinolone Signal and Related Alkylhydroxyquinolines by Rhodococcus sp. Strain BG43

Müller

Birmes

Niewerth

et al. 2014

Appl Environ Microbiol

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A bacterial strain, which based on the sequences of its 16S rRNA, gyrB, catA, and qsdA genes, was identified as a Rhodococcus sp. closely related to Rhodococcus erythropolis, was isolated from soil by enrichment on the Pseudomonas quinolone signal [PQS; 2-heptyl-3-hydroxy-4(1H)-quinolone], a quorum sensing signal employed by the opportunistic pathogen Pseudomonas aeruginosa. The isolate, termed Rhodococcus sp. strain BG43, cometabolically degraded PQS and its biosynthetic precursor 2-heptyl-4(1H)-quinolone (HHQ) to anthranilic acid. HHQ degradation was accompanied by transient formation of PQS, and HHQ hydroxylation by cell extracts required NADH, indicating that strain BG43 has a HHQ monooxygenase isofunctional to the biosynthetic enzyme PqsH of P. aeruginosa. The enzymes catalyzing HHQ hydroxylation and PQS degradation were inducible by PQS, suggesting a specific pathway. Remarkably, Rhodococcus sp. BG43 is also capable of transforming 2-heptyl-4-hydroxyquinoline-N-oxide to PQS. It thus converts an antibacterial secondary metabolite of P. aeruginosa to a quorum sensing signal molecule.

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Quinoline, quinazoline and acridonealkaloids

Abstract: This review covers the isolation, structure determination, synthesis and biological activity of quinoline, quinazoline and acridone alkaloids from plant, microbial and animal sources; 115 references are cited.

Cited by 1,125 publications

References 107 publications

A comprehensive view on 4-methyl-2-quinazolinamine, a new microbial alkaloid from Streptomyces of TCM plant origin

A comprehensive view on 4-methyl-2-quinazolinamine, a new microbial alkaloid from Streptomyces of TCM plant origin

Synthesis of bioisosteric 5-sulfa-rutaecarpine derivatives

Conversion of the Pseudomonas aeruginosa Quinolone Signal and Related Alkylhydroxyquinolines by Rhodococcus sp. Strain BG43

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