Cytotoxic Evaluation of Alkaloids and Isoflavonoids from the Australian Tree<i>Erythrina vespertilio</i>

Iranshahi, Mehrdad; Vu, Hoan; Pham, Ngoc Minh Quynh; Zencak, Dusan; Forster, Paul I.; Quinn, Ronald J.

doi:10.1055/s-0031-1298310

Cited by 23 publications

(11 citation statements)

References 21 publications

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“…Effects of alpinumisoflavone on proliferation after 24, 48, and 72 h incubation of human leukemia U937 cell line showed IC 50 values of 35, 32, and 28 μM, respectively (Matsuda et al 2007). Alpinumisoflavone exhibited weak cytotoxic activity against the prostate cancer (PC3) cell line (Iranshahi et al 2012). Wighteone and alpinumisoflavone isolated from E. indica (Leguminosae) showed cytotoxic activity against KB nasopharyngeal cancer cells, effective doses of 0.78 and 4.13 μg/ml, respectively (Orang-ojong et al 2013).…”

Section: Cytotoxic Activity Of Alpinumisoflavonementioning

confidence: 99%

Cytotoxic Activity of Alpinumisoflavone from Erythrina poeppigiana (Leguminosae) Against Colon Cancer (WiDr), Cervical Cancer (Hela), and Hepatoma Cancer (HepG2) Cells

et al. 2019

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Cancer is the second cause of death after cardiovascular diseases in the world. Anticancer prevention used can cause undesirable things. Flavonoids are secondary metabolites derived from natural products that are useful for anticancer treatment. This study was performed to observe the cytotoxic activity of alpinumisoﬂavone from Erythrina poeppigiana, toward cervical cancer (Hela), colon cancer (WiDr), and hepatoma cancer (HepG2) cells. The cytotoxic activity of alpinumisoﬂavone was tested using (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyltetrazolium bromide) assay. The percentage of cell mortality was calculated and the IC50 was calculated using probit analysis. The result shown that alpinumisoﬂavone has antiproliferative eﬀect to colon cancer (WiDr), cervical cancer (Hela), and hepatoma cancer (HepG2) cells with the value of IC50 are 5.63, 7.18, and 18.08 µg/ml, respectively. Based on the value of IC50 alpinumisoﬂavone is very cytotoxic to colon cancer WiDr cell.

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Section: Cytotoxic Activity Of Alpinumisoflavonementioning

confidence: 99%

Cytotoxic Activity of Alpinumisoflavone from Erythrina poeppigiana (Leguminosae) Against Colon Cancer (WiDr), Cervical Cancer (Hela), and Hepatoma Cancer (HepG2) Cells

et al. 2019

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“…However, in vitro bioassays have gone beyond implications from traditional uses. Pharmacological activities including anti-diabetic activity [10], cholesterol gall-stone prevention [8] and anticancer activities [11,12] have also been demonstrated from the crude extracts of E. lysistemon.…”

Section: Introductionmentioning

confidence: 99%

“…The (iso)flavonoid derivatives are commonly prenylated pterocarpans or prenylated isoflavones, prenylated flavones and flavans. Studies specifically of E. lysistemon have demonstrated an abundance of both classes of compound, but prenylated pterocarpans have received the greater focus with regards to the biological activities ascribed in medicinal practice [8][9][10] and erythrinan alkaloids have been previously linked to anticancer activities [12].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

et al. 2020

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Prenylated (iso)flavonoids, -flavans and pterocarpans from taxa in Erythrina are repeatedly flagged as potent antimicrobial compounds. In the current study, bark from E. lysistemon was extracted and seven isoflavone derivatives were purified: erybraedin A (1), phaseollidin (2), abyssinone V-4′ methyl ether (3), eryzerin C (4), alpumisoflavone (5), cristacarpin (6) and lysisteisoflavone (7). Minimum inhibition concentration (MIC) values were determined against a range of species of bacteria (skin pathogens), then values for another 67 derivatives from Erythrina, only against Staphylococcus aureus, were mined from the literature. Of the seven isolates, MIC values widely ranged from 1–600 μg/mL, with no obvious pattern of selectivity for Gram-types. Nevertheless, using the mined and experimentally determined values against S. aureus, Klekota-Roth fragments (Structure Activity Relationship: SAR) were determined then used as molecular descriptors to make a ‘decision tree’ based on structural characters inspired by the classes of antimicrobial potency (classes A-D). Furthermore, to make quantitative predictions of MIC values (Quantitative SAR: QSAR) ‘pace regression’ was utilized and validated (R² = 0.778, Q² = 0.727 and P² = 0.555). Evidently, the position and degree of prenylation is important; however, the presence of hydroxyl groups at positions 5 and 7 in ring A and 4′ in ring B is associated with lower MIC values. While antimicrobial results continue to validate the traditional use of E. lysistemon extracts (or Erythrina generally) in therapeutic applications consistent with anti-infection, it is surprising that this class of compound is not being utilized more often in general industry applications, such as food or cosmetic preservation, or in topical antimicrobial creams. Prenylated (iso)flavonoids are derived from several other Genera, such as Dorstenia (Moraceae), Ficus (Moraceae), Glycyrrhiza (Fabaceae), Paulownia (Lamiales) or Pomifera (Moraceae).

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“…Phaseollin, the third pterocarpan investigated to date, was first described to exert promising in vitro cytotoxic properties, according to an IC 50 in the low micromolar range and its ability to induce caspase 3- and 7-dependent apoptosis [ 25 ]. However, Iranshahi et al [ 26 ] found in 2012 a less potent activity against the prostate cancer cells PC3 (with an IC 50 higher than 10 µM). This compound structure harbors the same skeleton to that of erybraedin A but the prenylation differs: the prenylation on ring A is cyclized with the hydroxyl group, whereas the prenylation on the phenolic ring 4 is absent.…”

Section: In Vitro Anticancerous Activities Of Compounds From E Senegalensis : Mechanisms Of Actionmentioning

confidence: 99%

Systematic Review of Potential Anticancerous Activities of Erythrina senegalensis DC (Fabaceae)

Fofana

Ouédraogo

Esposito

et al. 2021

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The objective of this study was to carry out a systematic review of the substances isolated from the African medicinal plant Erythrina senegalensis, focusing on compounds harboring activities against cancer models detailed in depth herein at both in vitro and in vivo preclinical levels. The review was conducted through Pubmed and Google Scholar. Nineteen out of the forty-two secondary metabolites isolated to date from E. senegalensis displayed interesting in vitro and/or in vivo antitumor activities. They belonged to alkaloid (Erysodine), triterpenes (Erythrodiol, maniladiol, oleanolic acid), prenylated isoflavonoids (senegalensin, erysenegalensein E, erysenegalensein M, alpinumisoflavone, derrone, warangalone), flavonoids (erythrisenegalone, senegalensein, lupinifolin, carpachromene) and pterocarpans (erybraedine A, erybraedine C, phaseollin). Among the isoflavonoids called “erysenegalensein”, only erysenealenseins E and M have been tested for their anticancerous properties and turned out to be cytotoxic. Although the stem bark is the most frequently used part of the plant, all pterocarpans were isolated from roots and all alkaloids from seeds. The mechanisms of action of its metabolites include apoptosis, pyroptosis, autophagy and mitophagy via the modulation of cytoplasmic proteins, miRNA and enzymes involved in critical pathways deregulated in cancer. Alpinumisoflavone and oleanolic acid were studied in a broad spectrum of cancer models both in vitro and in preclinical models in vivo with promising results. Other metabolites, including carpachromen, phaseollin, erybraedin A, erysenegalensein M and maniladiol need to be further investigated, as they display potent in vitro effects.

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Cytotoxic Evaluation of Alkaloids and Isoflavonoids from the Australian TreeErythrina vespertilio

Cited by 23 publications

References 21 publications

Cytotoxic Activity of Alpinumisoflavone from Erythrina poeppigiana (Leguminosae) Against Colon Cancer (WiDr), Cervical Cancer (Hela), and Hepatoma Cancer (HepG2) Cells

Cytotoxic Activity of Alpinumisoflavone from Erythrina poeppigiana (Leguminosae) Against Colon Cancer (WiDr), Cervical Cancer (Hela), and Hepatoma Cancer (HepG2) Cells

Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

Systematic Review of Potential Anticancerous Activities of Erythrina senegalensis DC (Fabaceae)

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