The alkaloid, soyauxinium chloride, displays remarkable cytotoxic effects towards a panel of cancer cells, inducing apoptosis, ferroptosis and necroptosis

Mbaveng, Armelle T.; Noulala, Cédric Guy Tchatchouang; Samba, Anne R.M.; Tankeo, Simplice B.; Abdelfatah, Sara; Fotso, Ghislain Wabo; Happi, Emmanuel Ngeufa; Ngadjui, Bonaventure T.; Beng, Véronique Penlap; Kuete, Victor; Efferth, Thomas

doi:10.1016/j.cbi.2020.109334

Cited by 33 publications

(30 citation statements)

References 48 publications

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“…Herein we report the isolation and structural characterization of ten natural compounds from the total alkaloid extract of A. soyauxii, including a new indolopyridoquinazoline and the structural revision of soyauxinium chloride [ 1 , 2 ]. Furthermore, six semi-synthetic alkaloid derivatives were prepared.…”

Section: Resultsmentioning

confidence: 99%

“…We recently published a contribution to the taxonomy and chemistry of A. soyauxii . We reported the isolation of a new mesomeric form of quaternary indoloquinazoline alkaloid named soyauxinium chloride [ 1 , 2 ]. At that time, neither the NMR nor the MS data ( Supplementary Materials ) were enough to finalize the structure.…”

Section: Resultsmentioning

confidence: 99%

“…However, compound 5 turned out to be soyauxinium nitrate as it crystallizes in the space group P2 1 /c ( Figure 3 ). Therefore, the previously published soyauxinium chloride structure ( Figures S28–S35 ) [ 1 , 2 ] should be revised to soyauxinium nitrate ( 5 ). The presence of nitrate as counter-ion is not surprising as nitrate ions (NO 3 − ) are assimilated by plants from the soil for nutritional, environmental, or physiological purposes [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

“…Mziray] (Rutaceae) is a rich source of new bioactive substances. Our previous reports provided valuable insights on the biology and chemistry of the studied plant, which contains different types of alkaloids, including quinazoline, furoquinoline, indolopyridoquinazoline, and oxazole [ 1 , 2 , 3 ] examples, as almost every other species of the genus Araliopsis does. Furoquinoline-like alkaloids form the most representative class of compounds, with more than twenty derivatives already isolated in the genus and five encountered in the studied species.…”

Section: Introductionmentioning

confidence: 99%

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Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

et al. 2022

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The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

et al. 2022

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“…DCFH-DA was attached to the cell pellet and incubated at 370 °C for 45 min. After centrifuging the samples, fluorescence intensity was measured using a flow cytometer [10,23].…”

Section: Evaluation Of Free Radicals (Ros)mentioning

confidence: 99%

The effects of methanolic extract of the aerial parts of Galium verum on HT29 and AGO cell lines

Pashapour

Heshmati

Mousavi

et al. 2021

Nucleus

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The study reports the effects of methanol extract of Gallium verum on the cell proliferation of HT-29 (colon cancer) and AGO (fibroblast) cell lines. The cell lines were exposed to the G. verum extracts at the concentrations 12.5-400 μg/mL for a period of 72 h. Cell viability was evaluated by MTT assay. Apoptosis and cycle distribution were evaluated using flow cytometry, and RT-PCR was utilized for evaluating gene expression of the apoptotic cells. The results showed that the highest concentration (400 μg/mL) induced a significant decrease of cell viability in both HT29 and AGO cell lines. The percentage of apoptotic cells in the experimental group increased significantly when compared to the control group. The cell cycle was affected by an increased distribution of cells at G0/G1 phase and decreased occurrence of cells at S phase. The generation of reactive oxygen species (ROS) and the BAX/BCL2 ratio was found to be higher in the experimental group than that of the control group, respectively. Gallium verum at 400 μg/mL was found to decrease cell viability, induce apoptosis, increase BAX/BCL2 ratio and ROS production, and arresting cells at the G0/G1 phase.

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Ferroptosis‐modulating small molecules for targeting drug‐resistant cancer: Challenges and opportunities in manipulating redox signaling

Koeberle

Kipp

Stuppner

et al. 2023

Medicinal Research Reviews

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Ferroptosis is an iron-dependent cell death program that is characterized by excessive lipid peroxidation. Triggering ferroptosis has been proposed as a promising strategy to fight cancer and overcome drug resistance in antitumor therapy. Understanding the molecular interactions and structural features of ferroptosis-inducing compounds might therefore open the door to efficient pharmacological strategies against aggressive, metastatic, and therapyresistant cancer. We here summarize the molecular mechanisms and structural requirements of ferroptosisinducing small molecules that target central players in ferroptosis. Focus is placed on (i) glutathione peroxidase (GPX) 4, the only GPX isoenzyme that detoxifies complex membrane-bound lipid hydroperoxides, (ii) the cystine/ glutamate antiporter system X c − that is central for glutathione regeneration, (iii) the redox-protective transcription factor nuclear factor erythroid 2-related factor (NRF2), and (iv) GPX4 repression in combination with induced heme degradation via heme oxygenase-1. We deduce common features for efficient ferroptotic activity and highlight challenges in drug development. Moreover, we critically discuss the potential of natural products as

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The alkaloid, soyauxinium chloride, displays remarkable cytotoxic effects towards a panel of cancer cells, inducing apoptosis, ferroptosis and necroptosis

Cited by 33 publications

References 48 publications

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

The effects of methanolic extract of the aerial parts of Galium verum on HT29 and AGO cell lines

Ferroptosis‐modulating small molecules for targeting drug‐resistant cancer: Challenges and opportunities in manipulating redox signaling

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