Stryphnodendron adstringens (“Barbatimão”) Leaf Fraction: Chemical Characterization, Antioxidant Activity, and Cytotoxicity Towards Human Breast Cancer Cell Lines

Sabino, A P L; Eustáquio, Lívia Mara Santos; Miranda, A C F; Biojone, Caroline; Mariosa, T N; Gouvêa, Cibele Marli Cação Paiva

doi:10.1007/s12010-017-2632-z

Cited by 22 publications

(12 citation statements)

References 41 publications

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“…It was found that the fraction isolated from aqueous extract of Stryphnodendron adstringens (barbatimão) leaf showed morphological alterations like cell shrinkage, rounding-up, nuclear condensation and reduction of cell diameter and length in the treated two human breast cancer cell lines, MDA-MB-435 and MCF-7. The fraction was reported to be rich in gallic acid, (-)-epicatechin-3-O-gallate, and procyanidin dimer B1 [35].…”

Section: Discussionmentioning

confidence: 99%

Antioxidant, Antiproliferative and Apoptosis-Inducing Efficacy of Fractions from Cassia fistula L. Leaves

et al. 2020

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Cassia fistula L. is a highly admirable traditional medicinal plant used for the treatment of various diseases and disorders. The present study was performed to divulge the antioxidant, antiproliferative, and apoptosis-inducing efficacy of fractions from C. fistula leaves. The hexane (CaLH fraction), chloroform (CaLC fraction), ethyl acetate (CaLE fraction), n-butanol (CaLB fraction), and aqueous (CaLA fraction) were sequentially fractionated from 80% methanolic (CaLM extract) of C. fistula leaves. The CaLE fraction was fractionated using column chromatography to yield a pure compound, which was characterized as Epiafzelechin (CFL1) based on 1H, 13C, and DEPT135 NMR. Among these fractions, CaLE and isolated CFL1 fractions exhibited an effective antioxidant potential in Ferric ion reducing power, (2,2’-azino-bis (3-ethylbenzothiazoline -6-sulfonic acid)) cation radical scavenging, and nitric oxide radical scavenging assays. Epiafzelechin was investigated for its antiproliferative effects against MG-63 (osteosarcoma), IMR-32 (neuroblastoma), and PC-3 (prostate adenocarcinoma), and was found to inhibit cell proliferation with a GI50 value of 8.73, 9.15, and 11.8 μM respectively. MG-63 cells underwent apoptotic cell death on treatment with Epiafzelechin as the cells showed the formation of apoptotic bodies, enhanced reactive oxygen species (ROS) generation, mitochondrial membrane depolarization along with an increase in early apoptotic cell population analyzed using Annexin V-FITC/PI double staining assay. Cells showed cell cycle arrest at the G0/G1 phase accompanied by a downregulation in the expression levels of p-Akt (Protein kinase B), p-GSK-3β (Glycogen synthase kinase-3 beta), and Bcl-xl (B-cell lymphoma-extra large) proteins. RT-PCR (Real time-polymerase chain reaction) analysis revealed downregulation in the gene expression level of β-catenin and CDK2 (cyclin-dependent kinases-2) while it upregulated the expression level of caspase-8 and p53 genes in MG-63 cells.

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Section: Discussionmentioning

confidence: 99%

Antioxidant, Antiproliferative and Apoptosis-Inducing Efficacy of Fractions from Cassia fistula L. Leaves

et al. 2020

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“…The stem bark of “barbatimão” is the main utilized part of the plant and, therefore, its chemical composition was extensively studied focusing on its secondary metabolites, which led to the identification of high phenolic or tannic contents and elucidation of the main low- or high-weight tannins present in aqueous, hydroalcoholic, and acetone:water extracts [ 59 , 60 , 61 , 62 ]. Some extracts of “barbatimão” were also prepared using propylene glycol and water as solvent for use in pharmaceutical formulations.…”

Section: Chemical Compositionmentioning

confidence: 99%

“…Previously, prodelphinidins, gallic acid, and flavonols were also described in the leaves of S. adstringens and S. polyphyllum [ 62 ], as well as saponins and cumarins [ 71 ]. The tannins in the leaves were identified as gallic acid, epicatechin-(4β→8)-catechin, and epicatechin 3- O -gallate [ 59 ]. Moreover, galactomannans were extracted from the seeds of S. adstringens [ 72 ].…”

Section: Chemical Compositionmentioning

confidence: 99%

“…Furthermore, an ethyl acetate fraction obtained from the acetone:water extract of the leaves of S. adstringens was evaluated for antioxidant and anticancer potential. It showed good antioxidant activity by reducing iron, inhibiting protein oxidation and scavenging DPPH at same 50% radical inhibition concentration as vitamin C. The fraction did not show cytotoxicity for non-cancerous rat primary bone marrow but was cytotoxic to MCF-7 and MDA-MB-435 human breast cancer cell lines, and altered their morphology in addition to inducing DNA cleavage, apoptosis, and autophagy [ 59 ]. A tannin, epigallocatechin 3- O -gallate, present in the leaf fraction has already been designated as an anticarcinogenic compound [ 104 ].…”

Section: Correlated Biological Activitiesmentioning

confidence: 99%

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Stryphnodendron Species Known as “Barbatimão”: A Comprehensive Report

2018

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Stryphnodendron spp., popularly known as “barbatimão”, is the native Brazilian tree most often employed to treat wounds and infections. The aim of the present study was to highlight the importance of S. adstringens, as well as other Stryphnodendron species recognized as “barbatimão”, to human health, depicting the relevance of ethnopharmacological knowledge to scientific evidence for uses, related chemical compounds, development of pharmaceutical formulations, and the establishment of toxicity parameters. For this purpose, the literature databases PubMed, Scielo, Lilacs, CAPES Thesis and Google Scholar were searched until 2017. It was observed that stem bark was the primary part of the plant used, mainly as a decoction, for wound healing and treatment of infectious and inflammatory disorders. Confirmed biological activities, including wound healing, anti-inflammatory, antioxidant, and antimicrobial activities, were related to the presence of compounds from tannin class, mostly proanthocyanidins. Toxicity parameters for stem bark were inconclusive, but toxicity was observed to a significant extent when seeds were ingested by cattle or other animals. Due to these important and confirmed biological activities, government policy encourages the phytotherapic use of S. adstringens, and some formulations with stem bark extracts were developed and patented. Furthermore, antiprotozoal, hypoglycemic and antiviral activities were identified as promising.

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“…The genotoxic and acute and chronic toxicity of this plant have been assessed in rodents ( Costa et al, 2010 , 2013 ). This plant has been shown to be cytotoxic for human breast cancer cells ( Sabino et al, 2017 ). The proanthocyanidin polymer-rich fraction of S. adstringens stem bark is rich in condensed tannins, or proanthocyanidins, including several flavan-3-ols, such as prodelphinidins and prorobinetinidins ( de Mello et al, 1996a , b , 1999 ; Ishida et al, 2006 ).…”

Section: Introductionmentioning

confidence: 99%

Proanthocyanidin Polymer-Rich Fraction of Stryphnodendron adstringens Promotes in Vitro and in Vivo Cancer Cell Death via Oxidative Stress

et al. 2018

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Cervical cancer is the fourth most common cancer that affects women, mainly through human papilloma virus (HPV) infection with high-risk HPV16 and HPV18. The present study investigated the in vitro anticancer activity and mechanism of action of a proanthocyanidin polymer-rich fraction of Stryphnodendron adstringens (F2) in cervical cancer cell lines, including HeLa (HPV18-positive), SiHa (HPV16-positive), and C33A (HPV-negative) cells, and also evaluated in vivo anticancer activity. In vitro, cell viability was determined by the MTT assay. Cell migration was determined by the wound healing assay. The mechanism of action was investigated by performing ultrastructural analysis and evaluating reactive oxygen species (ROS) production, mitochondrial metabolism, lipoperoxidation, BCL-2 family expression, caspase expression, and DNA and cell membrane integrity. In vivo activity was evaluated using the murine Ehrlich solid tumor model. F2 time- and dose-dependently reduced cell viability and significantly inhibited the migration of cervical cancer cells. HeLa and SiHa cells treated with F2 (IC50) exhibited intense oxidative stress (i.e., increase in ROS and decrease in antioxidant species) and mitochondrial damage (i.e., mitochondrial membrane potential depolarization and a reduction of intracellular levels of adenosine triphosphate). Increases in the Bax/BCL-2 ratio and caspase 9 and caspase 3 expression, were observed, with DNA damage that was sufficient to trigger mitochondria-dependent apoptosis. Cell membrane disruption was observed in C33A cells (IC50 and IC90) and HeLa and SiHa cells (IC90), indicating progress to late apoptosis/necrosis. The inhibition of ROS production by N-acetylcysteine significantly suppressed oxidative stress in all three cell lines. In vivo, F2 significantly reduced tumor volume and weight of the Ehrlich solid tumor, and significantly increased lipoperoxidation, indicating that F2 also induces oxidative stress in the in vivo model. These findings indicate that the proanthocyanidin polymer-rich fraction of S. adstringens may be a potential chemotherapeutic candidate for cancer treatment.

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Stryphnodendron adstringens (“Barbatimão”) Leaf Fraction: Chemical Characterization, Antioxidant Activity, and Cytotoxicity Towards Human Breast Cancer Cell Lines

Cited by 22 publications

References 41 publications

Antioxidant, Antiproliferative and Apoptosis-Inducing Efficacy of Fractions from Cassia fistula L. Leaves

Antioxidant, Antiproliferative and Apoptosis-Inducing Efficacy of Fractions from Cassia fistula L. Leaves

Stryphnodendron Species Known as “Barbatimão”: A Comprehensive Report

Proanthocyanidin Polymer-Rich Fraction of Stryphnodendron adstringens Promotes in Vitro and in Vivo Cancer Cell Death via Oxidative Stress

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