Erybraedin C and bitucarpin A, two structurally related pterocarpans purified from Bituminaria bituminosa, induced apoptosis in human colon adenocarcinoma cell lines MMR- and p53-proficient and -deficient in a dose-, time-, and structure-dependent fashion

Maurich, Tiziana; Iorio, Mariacarla; Chimenti, Daniele; Turchi, G.

doi:10.1016/j.cbi.2005.10.103

Cited by 35 publications

(32 citation statements)

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“…In the last decade several examples of pterocarpans with antitumoral activity have been reported, like 3,4-dihydroxy-8,9-methylenedioxypterocarpan (4-hydroximaackiain) (Chaudhuri et al 1995), erybraedin C and bitucarpin A, isolated from Bituminaria bituminosa, may act as potent growth inhibitory compounds, comparable to other clinically important antineoplastic natural drugs, including etoposide, on human colon adenocarcinoma cells (Maurich et al 2006).…”

Section: Other Biological Propertiesmentioning

confidence: 99%

Pterocarpans: interesting natural products with antifungal activity and other biological properties

et al. 2007

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Section: Other Biological Propertiesmentioning

confidence: 99%

Pterocarpans: interesting natural products with antifungal activity and other biological properties

et al. 2007

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“…Good antioxidant and antibacterial activities have also been described for B. bituminosa extracts (Azzouzi et al, 2014;Martínez et al, 2010;Maurich et al, 2006;Walker et al, 2012). However, these previous studies were not focused on its phenolic profile.…”

Section: Introductionmentioning

confidence: 99%

HPLC-ESI-MSn characterization of phenolic compounds, terpenoid saponins, and other minor compounds in Bituminaria bituminosa

Llorent‐Martínez

Spínola

Gouveia

et al. 2015

Industrial Crops and Products

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Tandem mass spectrometry a b s t r a c t Bituminaria bituminosa is a wild legume that can endure drastic conditions, including contaminated and degraded soils. It has been traditionally used as feeding for livestock, and different uses in folk medicine are known. The chemical composition of leaves and flowers from B. bituminosa is presented for the first time. The screening of phytochemical compounds was carried out using high-performance liquid chromatography with electrospray ionization mass spectrometric detection (HPLC-ESI-MS n ). More than 40 compounds were identified or tentatively characterized. A high percentage of the detected compounds corresponded to glycosylated flavonoids, especially from apigenin, although phenolic acids, lignans, and saponins were also identified.

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“…While topoisomerase I is able to cleave one DNA strand, topoisomerase II cleaves both DNA strands. However, their function is essential for almost all DNA metabolism processes, and tyrosine (Tyr 723 ) is the binding site where topoisomerases start their nucleophilic attack and form DNA cleavable complex [49,66]. Erybraedin C, a prenylatedpterocarpan (compound 11 ; Figure 9) which was isolated from Bituminaria bituminosa flower (Leguminosae) showed antitumor activity against two human adenocarcinoma cell lines (HT29 and LoVo) proficient and deficient in MMR (mismatch repair), p53 and Bcl-2 [66].…”

Section: Pterocarpans As Anti-oxidant/cancer Agentsmentioning

confidence: 99%

“…However, their function is essential for almost all DNA metabolism processes, and tyrosine (Tyr 723 ) is the binding site where topoisomerases start their nucleophilic attack and form DNA cleavable complex [49,66]. Erybraedin C, a prenylatedpterocarpan (compound 11 ; Figure 9) which was isolated from Bituminaria bituminosa flower (Leguminosae) showed antitumor activity against two human adenocarcinoma cell lines (HT29 and LoVo) proficient and deficient in MMR (mismatch repair), p53 and Bcl-2 [66]. In a recent study, the molecular mechanism exploring the antitumor activity of compound 11 revealed that it demonstrates its effect through inhibition of topoisomerase I function but in a manner different from the other common topoisomerase I inhibitors.…”

Section: Pterocarpans As Anti-oxidant/cancer Agentsmentioning

confidence: 99%

“…These are involved in the catalytic reaction of the enzyme on the DNA strand, inhibiting their function so that it blocks the DNA cleavage step. Another interesting finding from the modeling study is the binding of compound 11 to the enzyme which gave enough space fitting for the DNA substrate into the enzyme cavity, so that compound 11 is considered the first example of a natural compound able to inhibit topoisomerase I reaction in both the cleavage and relegation steps without inhibition of the enzyme binding [66]. …”

Section: Pterocarpans As Anti-oxidant/cancer Agentsmentioning

confidence: 99%

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The Role of the MAPK Signaling, Topoisomerase and Dietary Bioactives in Controlling Cancer Incidence

et al. 2017

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Reactive oxygen species (ROS) are common products of mitochondrial oxidative phosphorylation, xenobiotics metabolism and are generated in response to several environmental stress conditions. Some of them play important biochemical roles in cellular signal transduction and gene transcription. On the other hand, ROS are known to be involved in a wide range of human diseases, including cancer. The excessive production of such ROS together with disruption of homeostasis detoxifying mechanisms can mediate a series of cellular oxidative stresses. The oxidative stress of redundant free radicals production can lead to oxidative denaturation of cellular macromolecules including proteins, lipids and DNA. Moreover, oxidative damage is one of the major causes of DNA mutations, replication errors and genomic abnormalities which result in either inhibition or induction of transcription, and end with the disturbance of signal transduction pathways. Among affected signaling pathways are redox-sensitive kinases. The stimulation of these kinases induces several transcription factors through the phosphorylation of their module proteins. The activation of such pathways induces proliferation and cellular transformation. A diet rich in antioxidant compounds has potential health benefits, and there is a growing interest in the role of natural antioxidants in nutrition for prevention and cure of cancer diseases. A controversy has risen regarding the relation between antioxidants and the significant decrease in the risk of cancer incidence. In this review, we will focus on redox-sensitive kinases signaling pathways, highlighting the effects of dietary antioxidant on the prevention, incidence, prognosis or even treatment of human cancers. In addition, we will place emphasis on the chemical classes of pterocarpans as natural anti-oxidants/cancers as well as their underlying mechanisms of action, including their effects on MAPKs and topoisomerase activities.

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Erybraedin C and bitucarpin A, two structurally related pterocarpans purified from Bituminaria bituminosa, induced apoptosis in human colon adenocarcinoma cell lines MMR- and p53-proficient and -deficient in a dose-, time-, and structure-dependent fashion

Cited by 35 publications

References 39 publications

Pterocarpans: interesting natural products with antifungal activity and other biological properties

Pterocarpans: interesting natural products with antifungal activity and other biological properties

HPLC-ESI-MSn characterization of phenolic compounds, terpenoid saponins, and other minor compounds in Bituminaria bituminosa

The Role of the MAPK Signaling, Topoisomerase and Dietary Bioactives in Controlling Cancer Incidence

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