Alkaloids Derived from Anthranilic Acid: Quinoline, Acridone, and Quinazoline

Silva, Maria Fátima das Graças Fernandes da; Fernandes, João B.; Forim, Moacir Rossi; Vieira, Paulo C.; Sá, Israel Cívico Gil de

doi:10.1007/978-3-642-22144-6_25

Cited by 5 publications

(4 citation statements)

References 144 publications

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“…En una placa de 96 pozos se adicionan por pozo 50 μl de solución de ensayo y 50 μl de enzima a la concentración de trabajo 0,02 M (AChE), a continuación, se hace la incubación Por otra parte, el compuesto C4 se identificó como ácido antranilico (ácido 2aminobenzoico), en este caso su estructura si pudo ser confirmada por comparación con los datos espectroscópicos reportados en Yang et al 2012; la literatura relacionada con este metabolito, en su mayoría, muestran que se aísla con más frecuencia de hongos y bacterias, pero su presencia en Z. caribaeum no es de extrañar ya que este metabolito es el precursor de alcaloides tipo quinolina, además de otros metabolitos importantes en las plantas como el Triptófano (Dreyer & Brenner, 1980) (da Silva, Fernandes, Forim, Vieira, & de Sá, 2013.…”

Section: Ensayo De Inhibición De Acetilcolinesterasa Y Butilcolineste...unclassified

Chemical Composition, Antimicrobial, Repellent and Antioxidant Activity of Essential Oil ofZanthoxylum caribaeumLam

Souza

Toledo

Walerius

et al. 2019

Journal of Essential Oil Bearing Plants

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Thus, the bioguided purification led to the isolation and characterization of the following compounds: 6,8-dimethoxy-2-H-1-quinolin-2-one, 3-((1-methylciclopentil) amino) quinolin-2(1H)-one, 104-ozaxol [3,2-a] quinoline and Anthranilic acid and the evaluation of its possible neuroprotective activity, based on the results of antioxidant and anticholinergic activity, showed that the compounds individually present medium to low antioxidant activities and that the anticholinergic activity is lost as the putification progresses, the fractions being more active than the pure compounds.

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Section: Ensayo De Inhibición De Acetilcolinesterasa Y Butilcolineste...unclassified

Chemical Composition, Antimicrobial, Repellent and Antioxidant Activity of Essential Oil ofZanthoxylum caribaeumLam

Souza

Toledo

Walerius

et al. 2019

Journal of Essential Oil Bearing Plants

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“…The major types of rutaceous secondary metabolites were also isolated and they show that H. oreadica , H.brasiliana and H. superba are related to other species of Hortia . However, the alkaloids N -methylatanine, robustine [26,27], 7,8-dehydrorutaecarpine [28], edulitine [29], integriquinolone [30], the coumarins psoralen, bergapten, xanthotoxin, 5-methoxyseselin, braylin, isopimpinellin, prangol, heraclenol, seselin, 5-methoxyseselin [31], the flavonoids isosakuranetin [32], acacetin [29], neoponcirin [33], and the limonoid limonin [34] are reported for the first time from the Hortia .…”

Section: Resultsmentioning

confidence: 99%

New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

et al. 2014

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Abstract:Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica, H. brasiliana and H. superba searching for other secondary metabolites present in substantial amounts for taxonomic analysis. In a continuation of the investigation of the H. oreadica, three new limonoids have now been isolated 9α-hydroxyhortiolide A, 11β-hydroxyhortiolide C and 1(S*)-acetoxy-7(R*)-hydroxy-7-deoxoinchangin. All the isolated compounds from the Hortia species reinforce its position in the Rutaceae. With regard to limonoids the genus produces highly specialized compounds, whose structural variations do not occur in any other member of the Rutaceae, thus, it is evident from limonoid data that Hortia takes an isolated position within the family. In addition, H. superba afforded the unexpected coumarin 5-chloro-8-methoxy-psoralen, which may not be a genuine natural product. Solid-state cross-polarisation/magic-anglespinning 13 C nuclear magnetic resonance, X-Ray fluorescence and Field-emission gun scanning electron microscopy experiments show that the Sephadex LH-20 was modified after treatment with NaOCl, suggesting that when xanthotoxin (8-methoxy-psoralen) was extracted from cleaning of the gel column, chlorination of the aromatic system occurred.

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“…Rutaceae has been a source of interest for its novel anthranillic acid derived alkaloids with biologically active antibacterial and antifungal properties (da Silva et al 2013). Ruta angustifolia (Garuda or Aruda in Malay) of the Rutaceae is one of the rich sources of anthranilic acid derived alkaloids including acridone, quinoline, quinolone and furoquinoline alkaloids (El Sayed et al 2003).…”

Section: Introductionmentioning

confidence: 99%

Graveoline from Ruta angustifolia (L.) Pers. and Its Antimicrobial Synergistic Potential in Erythromycin or Vancomycin Combinations

Kamal¹,

Hassan²,

Taib³

et al. 2018

JSM

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Ruta angustifolia (L.) Pers. is a Rutaceous species which contains various anthranilic acid derived alkaloids including the bioactive quinolones. This study is aimed at identifying the antimicrobial active alkaloids of R. angustifolia and evaluating their potential as synergistic enhancers in alkaloid-antibiotic combinations. Antimicrobial bioautographyguided isolation of alkaloidal fractions of R. angustifolia leaves has led to the identification of 2,3-dimethoxy-1-hydroxy-10-methylacridone [arborinine]; and 4,7,8-trimethoxyfuro[2,3-b]quinoline [skimmianine]; together with the major active alkaloid, 1-methyl-2-[3',4'-methylenedioxyphenyl]-4-quinolone [graveoline]. Graveoline showed Minimum Inhibitory Concentration (MIC) values ranging from 500 to 1000 µg/mL against Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212 and Escherichia coli ATCC 25922. Checkerboard assay for antimicrobial combination effects between graveoline with either erythromycin or vancomycin showed enhancement of the antimicrobial activity of both antibiotics with Fractional Inhibitory Concentration Indices (FICI) ranged from 0.37 to 1.50. Synergistic effect with FICI of 0.37 was observed for graveoline-erythromycin combination against S. aureus compared to FICI of 1.00 for ciprofloxacin-erythromycin additive effect. Graveoline was a potential candidate for antimicrobial combination agent especially against S. aureus. The result supports the idea of using plant metabolites as antimicrobial synergistic agents.

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Alkaloids Derived from Anthranilic Acid: Quinoline, Acridone, and Quinazoline

Cited by 5 publications

References 144 publications

Chemical Composition, Antimicrobial, Repellent and Antioxidant Activity of Essential Oil ofZanthoxylum caribaeumLam

Chemical Composition, Antimicrobial, Repellent and Antioxidant Activity of Essential Oil ofZanthoxylum caribaeumLam

New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

Graveoline from Ruta angustifolia (L.) Pers. and Its Antimicrobial Synergistic Potential in Erythromycin or Vancomycin Combinations

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