Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco)

Fomani, Marie; Happi, Emmanuel Ngeufa; Bisoue, Achille Nouga; Ndom, Jean Claude; Waffo, Alain François Kamdem; Sewald, Norbert; Wansi, Jean Duplex

doi:10.1016/j.bmcl.2015.12.028

Cited by 22 publications

(11 citation statements)

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“…Xanthyletin (2): (Tillekeratne, De Silva, Mahindaratne, et al, 1989). Lupeol (3): (Fomani et al, 2016). β-amyrin (4): (Longue, Nouga, Fomani, et al, 2015).…”

Section: Methodsmentioning

confidence: 99%

“…β-amyrin (4): (Longue, Nouga, Fomani, et al, 2015). Stigmasterol (5): (Fomani et al, 2016). β-sitosterol (6): (Fomani et al, 2016).…”

Section: Methodsunclassified

“…Conversely, however, very little is known about the pharmacological potential of secondary metabolites produced by seeds, leaves, roots and the bark of the Citrus species. In our ongoing investigation of the medical potential of plants of the Rutaceae family, several compounds isolated from the roots of C. reticulata have been reported to display strong oxidative burst inhibition and suppression of the phagocytosis response upon activation with serum opsonized zymosan in the range of 0.2-10.5 μM (Fomani, Ngeufa, Nouga, et al, 2016). In continuation of our research on C. reticulata, this paper deals with the isolation, structure elucidation and pharmacological evaluation of secondary metabolites produced by its stem bark.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Properties of the Stem Bark ofCitrus reticulataBlanco (Rutaceae)

et al. 2017

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The bioassay-guided fractionation of the n-hexane extract of Citrus reticulata Blanco (Rutaceae) stem bark yielded scoparone (1), xanthyletin (2), lupeol (3), β-amyrin (4), stigmasterol (5), β-sitosterol (6) and palmitic acid. The structures of these compounds were determined by comprehensive spectroscopic analyses, i.e., 1D and 2D NMR and EI-MS, and by comparison with the reported data. Extracts, fractions and isolated compounds 1-6 were assessed for cytotoxicity by the 3-(4,5-dimethylthiazol-2-yl)-2,5-dphenyltetrazolium bromide (MTT) assay against three human cancer cell lines, i.e., human lung adenocarcinoma cell line A549, human breast adenocarcinoma cell line MCF7 and human Caucasian prostate adenocarcinoma cell line PC3. Significant activity of the n-hexane and the dichloromethane extracts was observed against the breast cancer cell line MCF7 with IC s of 45.6 and 54.7 μg/mL, respectively. Moreover, the 70% ethyl acetate in n-hexane chromatographic fraction showed significant activity displaying IC values of 53.0, 52.4 and 49.1 μg/mL against the cancer cell lines A549, MCF7 and PC3, respectively. Encouragingly, an IC of 510.0 μg/mL against the human normal prostate cell line PNT2 indicated very low toxicity and hence favourable selectivity indices for the 70% ethyl acetate in n-hexane fraction in the range of 9.6-10.4 towards cell lines A549, MCF7 and PC3. Because compounds isolated from the above fraction only delivered IC values in the range of 18.2-96.3, 9.2-34.1 and 7.5-97.2 μg/mL against A549, MCF7 and PC3 cell lines, respectively, synergistic action between compounds is suggested. Bioassay results valorize the anticancer effectivity of the stem bark of this plant in Cameroonian pharmacopoeia. Copyright © 2017 John Wiley & Sons, Ltd.

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“…Xanthyletin (2): (Tillekeratne, De Silva, Mahindaratne, et al, 1989). Lupeol (3): (Fomani et al, 2016). β-amyrin (4): (Longue, Nouga, Fomani, et al, 2015).…”

Section: Methodsmentioning

confidence: 99%

“…β-amyrin (4): (Longue, Nouga, Fomani, et al, 2015). Stigmasterol (5): (Fomani et al, 2016). β-sitosterol (6): (Fomani et al, 2016).…”

Section: Methodsunclassified

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Properties of the Stem Bark ofCitrus reticulataBlanco (Rutaceae)

et al. 2017

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“…Approximately 270 alkaloids of the acridone family have been described (Michael, 2017), and due to their multiple uses, a large number of acridone derivatives have also been synthesized. Among their most noteworthy properties are the effects of acridones and synthetic analogs as antineoplastic agents (Kuete et al, 2015; Fomani et al, 2016; Schelz et al, 2016). Antibacterial and antiviral activities have also been described (Wansi et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

Coupled Excited-State Dynamics in N-Substituted 2-Methoxy-9-Acridones

et al. 2019

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Fluorophores of the acridone family have been widely employed in many applications, such as DNA sequencing, the detection of biomolecules, and the monitoring of enzymatic systems, as well as being the bases of intracellular sensors and even antitumoral agents. They have been widely used in fluorescence imaging due to their excellent photophysical properties, in terms of quantum yield and stability. However, frequently, the fluorescence emission data from acridones are not easily interpretable due to complex excited-state dynamics. The formation of π-stacking aggregates and excimers and excited-state proton transfer (ESPT) reactions usually result in emission features that are dependent on the experimental conditions. Therefore, an in-depth understanding of the dynamics involved in the excited-state transients of these dyes is mandatory for their appropriate application. Herein, we synthesized and fully characterized different 2-methoxy-9-acridone dyes. Their transient fluorescence emission spectra exhibited a complex dynamic behavior that can be linked to several excited-state reactions. We performed a thorough study of the excited-state dynamics of these dyes by means of time-resolved fluorimetry supported by computational calculations. All this allowed us to establish a multistate kinetic scheme, involving an ESPT reaction coupled to an excimer formation process. We have unraveled the rich dynamics behind this complex behavior, which provides a better understanding of the excited states of these dyes.

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“…1). By comparison with the reported data, the known compounds were identified as citracridone I (2), citracridone III 3, 5hydroxynoracronycine (4), 5-methoxynoracronycine (5), 2-hydroxyruteacarpine (7), 2methoxyruteacarpine (8), 5,8,13,14-tetrahydro-2-methoxy-14-méthyl-5-oxo- 7Hindolo[2',3':3,4]pyrido[2,1-b]quinazolin-6-ium chloride (9), lupeol and β-sitosterol (Ezugwu et al, 2003;Wansi et al, 2008, Happi et al, 2011Fomani et al, 2016), whilst the new compounds were identified by comprehensive spectroscopic analyses.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic acridone and indoloquinazoline alkaloids from Zanthoxylum poggei

Wansi

Tcho

Toze

et al. 2016

Phytochemistry Letters

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Two new alkaloids, poggeicridone (1) and 2-methoxy-7,8-dehydroruteacarpine (6), together with nine known compounds, were isolated from the dichloromethane (DCM) extract of the bark of Zanthoxylum poggei (Engl.) P. G. Waterman. The structures of all compounds were determined by comprehensive spectroscopic analyses (1D and 2D NMR and EI-and ESI-MS)). Compounds 5-9 exhibited strong suppressive effects on the phagocytosis response upon activation with serum opsonized zymosan in the in vitro oxidative burst studies using whole blood. The IC50 values were in the range of 12.0-25.9 μM. These compounds displayed a moderate level of cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC50 values of 15.8 and 22.1 µM (the IC50 value of the positive control standard doxorubicin was IC50 0.9 µM). All isolated compounds were also tested against plant pathogenic bacteria, fungi and oomycetes using the paper disk agar diffusion assay, resulting in no significant activities (MICs > 1 mg/mL).

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Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco)

Cited by 22 publications

References 14 publications

Cytotoxic Properties of the Stem Bark ofCitrus reticulataBlanco (Rutaceae)

Cytotoxic Properties of the Stem Bark ofCitrus reticulataBlanco (Rutaceae)

Coupled Excited-State Dynamics in N-Substituted 2-Methoxy-9-Acridones

Cytotoxic acridone and indoloquinazoline alkaloids from Zanthoxylum poggei

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