Biological activity and stability analyses of knipholone anthrone, a phenyl anthraquinone derivative isolated from Kniphofia foliosa Hochst.

Feilcke, Ruth; Arnouk, Georgette; Raphane, Boingotlo; Richard, Khumoekae; Tietjen, Ian; Andrae‐Marobela, Kerstin; Erdmann, Frank; Schipper, Susanne; Becker, Katja; Arnold, Norbert; Frolov, Andrej; Reiling, Norbert; Imming, Peter; Fobofou, Serge Alain Tanemossu

doi:10.1016/j.jpba.2019.05.065

Cited by 24 publications

(17 citation statements)

References 27 publications

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“…Several studies have reported antiparasitic effects of natural and isolated/synthetic anthraquinones on diverse pathogenic unicellular eukaryotes (Leishmania donovani, L. major, Plasmodium falciparum, Trypanosoma brucei), but the mechanism of action remains speculative [31,32,33,34,35,36]. When interacting with the cellular chemistry of the pathogen, these compounds seem to generate free oxygen metabolites (which are toxic), alter DNA replication/repair enzymes, or cause direct damage on the DNA [31,32,33,34,35,36].…”

Section: Discussionmentioning

confidence: 99%

Anti-amebic effects of Chinese rhubarb (Rheum palmatum) leaves' extract, the anthraquinone rhein and related compounds

Espinosa

Paz-y-Miño-C

Santos

et al. 2020

Heliyon

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Entamoeba histolytica infects 50 million people worldwide and causes 55 thousand fatalities every year. Current anti-amebic drugs (e.g. paromomycin) work either at the level of the intestinal lumen (where trophozoites proliferate via cell divisions) or on the invasive trophozoites that have penetrated the gut or colonized internal organs (e.g. metronidazole). Some of these drugs are highly toxic to patients, have generated trophozoite resistance, or caused mutations and cancer in laboratory animals. Thus, alternative anti-amebic compounds need to be identified to minimize the side effects (on patients) or resistance (by amebas) to current treatments. The literature suggests that anthraquinones (chemicals found in medicinal plants) have antibacterial, antiparasitic, antiinflammatory and antioxidant properties. Here we provide experimental evidence that Chinese rhubarb (Rheum palmatum) leaves' extract (rich in the anthraquinone rhein) inhibits E. histolytica trophozoite growth in vitro. In addition, from a set of ten isolated/synthetic anthraquinones (which we suspected to have anti-amebic properties), four analogs (rhein; AHHDAC ¼ 1-amino-4-hydroxy-9, 10-dioxo-9, 10-dihydro-anthracene-2-carboxylic acid; unisol blue AS; and sennoside B) efficiently inhibited amebic growth at EIC 50 concentrations comparable to metronidazole. The mechanism of action of these compounds still needs to be determined, although anthraquinones might enhance the production of toxic oxygen metabolites as it has been suggested for various protists (e.g. Leishmania, Plasmodium, Trypanosoma). Our research is the first to explore anti-amebic effects of Chinese rhubarb leaves' extract and isolated/synthetic anthraquinones on pathogenic Entamoeba.

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Section: Discussionmentioning

confidence: 99%

Anti-amebic effects of Chinese rhubarb (Rheum palmatum) leaves' extract, the anthraquinone rhein and related compounds

Espinosa

Paz-y-Miño-C

Santos

et al. 2020

Heliyon

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“…phenylanthraquinone in Bulbine species [3], as well as analogues, displays a broad range of activities including in vitro cytotoxicity, anthelmintic, antibacterial and anti-HIV-1 [12], anti-plasmodial [12][13][14], antiproliferative [15], and antioxidant activities [16,17].…”

Section: Development and Validation Of A Uhplc-pda-ms Methods For The mentioning

confidence: 99%

Development and Validation of a UHPLC-PDA-MS Method for the Quantitative Analysis of Anthraquinones in Bulbine natalensis Extracts and Dietary Supplements

et al. 2019

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A UHPLC-photodiode array-MS method was developed and validated for the quantification of one chromone and six anthraquinone type of compounds from Bulbine natalensis plant samples and dietary supplements. Metabolites 1 – 7 were identified based on their retention times and electrospray ionization-MS spectra compared with a mix of previously isolated compounds. The quantification of 1 – 7 was based on photodiode array detection. The optimized separation was achieved using a CORTECS C18 column with a gradient of water/acetonitrile as the mobile phase. Seven compounds were separated within 15 minutes with detection limits of 50 pg on the column. The analytical method was validated for linearity, repeatability, accuracy, limits of detection, and limits of quantification. The relative standard deviations for intra- and inter-day experiments were less than 5% and the recovery efficiency was 98 – 101%. Nine dietary supplements labeled as containing B. natalensis were examined. Anthraquinone-type compounds were detected in only five out of nine dietary supplements, with the total amount ranging from 11.3 to 90.4 mg per daily dose. The analytical method is simple, economic, rapid, and can be applied for quality assessment of B. natalensis and dietary supplements. Electrospray ionization-MS was used for the identification of these compounds in plant samples and dietary products.

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“…The mode of action of natural 4-arylanthraquinones has not been established. These compounds triggered both apoptosis and necrosis and also induced DNA damage in cancer cells [7]. We further studied the action of the synthesized arylanthraquinones on the beta isoform of human topoisomerase II in silico.…”

Section: Cytotoxicity Studiesmentioning

confidence: 99%

“…From these compounds the natural 4-arylanthraquinones-knipholones -are of interest. Knipholone and isoknipholone have recently been reported to exhibit good antitumoral activities against several cancer cells, some of them comparable to that of etoposide [4,7]. Knipholone and its related derivatives have been reported to exhibit significant activities against the malaria parasite, Plasmodium falciparum [6].…”

Section: Introductionmentioning

confidence: 99%

“…The Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of the mentioned compounds with aryl boronic acids was the main route of synthesis. Taking into account the interest to substituted 4-arylanthraquinones as anticancer agents [4,6,7], we evaluated the cytotoxicity of the synthesized compounds toward a panel of cancer cell lines in vitro and also obtained some data about the potential mechanism of action of the new compounds.…”

Section: Introductionmentioning

confidence: 99%

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1-Hydroxyanthraquinones Containing Aryl Substituents as Potent and Selective Anticancer Agents

et al. 2020

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A series of 1,2-, 1,4-disubstituted or 1,2,4-trisubstituted anthraquinone-based compounds was designed, synthesized, characterized and biologically evaluated for anticancer efficacy. 2- or 4-arylated 1-hydroxy-9,10-antraquinones (anthracene-9,10-diones) were prepared by Suzuki–Miyaura cross-coupling reaction of 1-hydroxy-2-bromoanthraquinone, 1-hydroxy-4-iodoanthraquinone or 1-hydroxy-2,4-dibromoanthraquinone with arylboronic acids. The cross-coupling reaction of 2,4-dibromo-9,10-anthraquinone with arylboronic acids provide a convenient approach to 2,4-bis arylated 1-hydroxyanthraquinones with a variety of aryl substituent in the 2 and 4 position. The cytotoxicity of new anthraquinone derivatives was evaluated using the conventional MTT assays. The data revealed that six of the aryl substituted compounds among the entire series 3, 15, 16, 25, 27, 28 were comparable potent with the commercially available reference drug doxorubicin on the human glioblastoma cells SNB-19, prostate cancer DU-145 or breast cancer cells MDA-MB-231 and were relatively safe towards human telomerase (h-TERT)immortalized lung fibroblasts cells. The results suggested that the in vitro antitumor activity of synthesized 2-aryl, 4-aryl- and 2,4-diaryl substituted 1-hydroxyanthraquinones depends on the nature of the substituent within the cyclic backbone. Docking interaction of 2-, 4-substituted and 2,4-disubstituted 1-hydroxyanthraquinones indicates intercalative mode of binding of compounds with DNA topoisomerase. The interaction with the DNA of 4-aryl-13, 15, 16 and 4-(furan-3-yl)-23 1-hydroxyanthraquinones was experimentally confirmed through a change in electroforetic mobility. Further experiments with 1-hydroxy-4-phenyl-anthraquinone 13 demonstrated that the compound induced cell cycle arrest at sub-G1 phase in DU-145 cells in the concentration 1.1 μM, which is probably achieved by inducing apoptosis. 4-Arylsubstituted 1-hydroxyanthraquinones 13 and 16 induced the enhancement of DNA synthesis on SNB19 cell lines.

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Biological activity and stability analyses of knipholone anthrone, a phenyl anthraquinone derivative isolated from Kniphofia foliosa Hochst.

Cited by 24 publications

References 27 publications

Anti-amebic effects of Chinese rhubarb (Rheum palmatum) leaves' extract, the anthraquinone rhein and related compounds

Anti-amebic effects of Chinese rhubarb (Rheum palmatum) leaves' extract, the anthraquinone rhein and related compounds

Development and Validation of a UHPLC-PDA-MS Method for the Quantitative Analysis of Anthraquinones in Bulbine natalensis Extracts and Dietary Supplements

1-Hydroxyanthraquinones Containing Aryl Substituents as Potent and Selective Anticancer Agents

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