1,2,3,4,6-Penta-O-galloyl-β-d-glucose suppresses colon cancer through induction of tumor suppressor

Kawk, Sang Hee; Kang, Yun Ju; Kim, Yoon Hee

doi:10.1016/j.bmcl.2018.05.028

Cited by 19 publications

(20 citation statements)

References 35 publications

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“…7b). These compounds have been reported to possess cytotoxic activity in cancer cells [13, 44, 47] and may be related to the medicinal properties of RHTR observed in this study (Additional file 3: Table S1). However, complementary studies are required to demonstrate whether there is a major compound in FF or a responsible synergistic mechanism.…”

Section: Resultsmentioning

confidence: 59%

“…The analysis revealed a high content of polyphenols and flavonoids with antioxidant activity in AE-RHTR, which included methyl gallate, epigallocatechin 3-cinnamate, quercetin 3-(2″‘-galloylglucosyl)-(1 → 2)-alpha-L-arabinofuranoside, β -PGG, 4- O -digalloyl-1, 2, 3, 6-tetra- O - β -D-galloylglucose, myricetin 3-(4″-galloylrhamnoside), and fisetin. The concentrations of these compounds were increased in the FF fraction, and other research groups have reported that some of these compounds are important active principles against cancer by activating different molecular mechanisms involved in the state of quiescence and cell death [13, 44, 47]. Thus, we considered that the antineoplastic activity observed in RHTR might be related to the combination of these compounds in the AE.…”

Section: Discussionmentioning

confidence: 97%

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Biological and toxicological evaluation of Rhus trilobata Nutt. (Anacardiaceae) used traditionally in mexico against cancer

Varela-Rodríguez

Sánchez‐Ramírez

Rodríguez-Reyna

et al. 2019

BMC Complement Altern Med

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Background Rhus trilobata Nutt. ( Anacardiaceae ) (RHTR) is a plant of Mexico that is traditionally used as an alternative treatment for several types of cancer. However, the phytochemical composition and potential toxicity of this plant have not been evaluated to support its therapeutic use. Therefore, this study aimed to evaluate the biological activity of RHTR against colorectal adenocarcinoma cells, determine its possible acute toxicity, and analyze its phytochemical composition. Methods The traditional preparation was performed by decoction of stems in distilled water (aqueous extract, AE), and flavonoids were concentrated with C 18 -cartridges and ethyl acetate (flavonoid fraction, FF). The biological activity was evaluated by MTT viability curves and the TUNEL assay in colorectal adenocarcinoma (CACO-2), ovarian epithelium (CHO-K1) and lung/bronchus epithelium (BEAS-2B) cells. The toxicological effect was determined in female BALB/c mice after 24 h and 14 days of intraperitoneal administration of 200 mg/kg AE and FF, respectively. Later, the animals were sacrificed for histopathological observation of organs and sera obtained by retro-orbital bleeding for biochemical marker analysis. Finally, the phytochemical characterization of AE and FF was conducted by UPLC-MS E . Results In the MTT assays, AE and FF at 5 and 18 μg/mL decreased the viability of CACO-2 cells compared with cells treated with vehicle or normal cells ( p ≤ 0.05, ANOVA), with changes in cell morphology and the induction of apoptosis. Anatomical and histological analysis of organs did not reveal important pathological lesions at the time of assessment. Additionally, biochemical markers remained normal and showed no differences from those of the control group after 24 h and 14 days of treatment ( p ≤ 0.05, ANOVA). Finally, UPLC-MS E analysis revealed 173 compounds in AE-RHTR, primarily flavonoids, fatty acids and phenolic acids. The most abundant compounds in AE and FF were quercetin and myricetin derivates (glycosides), methyl gallate, epigallocatechin-3-cinnamate, β -PGG, fisetin and margaric acid, which might be related to the anticancer properties of RHTR. Conclusion RHTR exhibits biological activity against cancer cells and does not present adverse toxicological effects during its in vivo administration, supporting its traditional use. Electronic supplementary material The online version of this article (10.1186/s12906-019-2566-9) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 59%

Section: Discussionmentioning

confidence: 97%

Biological and toxicological evaluation of Rhus trilobata Nutt. (Anacardiaceae) used traditionally in mexico against cancer

Varela-Rodríguez

Sánchez‐Ramírez

Rodríguez-Reyna

et al. 2019

BMC Complement Altern Med

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“…Studies of gallotannins from red maple species in colon and breast cancer cells showed an association between the higher number of galloyl groups in the gallotannins and better anticancer activity [22]. Particularly, the penta galloyl glucoside from fruits, such as maple, gallnuts, and oak, and medicinal herbs ( Galla rhois, Rhus chineensis, Paeonia suffruticosa ) has been widely associated to anticancer effects in prostate, breast, glioma, hepatocellular, and colorectal carcinoma [72,73,74]. The suggested mechanisms associated to the cytotoxicity involve induction of apoptosis through an increase of Bax/Bcl-2 protein levels, cell cycle arrest in S-phase, and the inhibition of NF-κB activation, with the consequent downregulation of inflammatory cytokines [73].…”

Section: Resultsmentioning

confidence: 99%

Polyphenolic Characterization, Antioxidant, and Cytotoxic Activities of Mangifera indica Cultivars from Costa Rica

Navarro

Arnáez

Moreira

et al. 2019

Foods

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The phenolic profile of skin and flesh from Manifera indica main commercial cultivars (Keitt and Tommy Atkins) in Costa Rica was studied using ultra performance liquid chromatography coupled with high resolution mass spectrometry (UPLC-ESI-MS) on enriched phenolic extracts. A total of 71 different compounds were identified, including 32 gallates and gallotannins (of different polymerization degree, from galloyl hexose monomer up to decagalloyl hexoses and undecagalloyl hexoses); seven hydroxybenzophenone (maclurin and iriflophenone) derivatives, six xanthonoids (including isomangiferin and mangiferin derivatives); 11 phenolic acids (hydroxybenzoic and hydroxycinnamic acid derivatives); and eight flavonoids (rhamnetin and quercetin derivatives). The findings for T. Atkins skin constitute the first report of such a high number and diversity of compounds. Also, it is the first time that the presence of gallotannin decamers and undecamers are reported in the skin and flesh of Keitt cultivar and in T. Atkins skins. In addition, total phenolic content (TPC) was measured with high values especially for fruits’ skins, with a TPC of 698.65 and 644.17 mg gallic acid equivalents/g extract, respectively, for Keitt and T. Atkins cultivars. Antioxidant potential using 2,2-diphenyl-1-picrylhidrazyl (DPPH) and oxygen radical absorbance capacity (ORAC) methods were evaluated, with T. Atkins skin showing the best values for both DPPH (IC50 = 9.97 µg/mL) and ORAC (11.02 mmol TE/g extract). A significant negative correlation was found for samples between TPC and DPPH antioxidant values (r = −0.960, p < 0.05), as well as a significant positive correlation between TPC and ORAC (r = 0.910, p < 0.05) and between DPPH and ORAC antioxidant methods (r = 0.989, p < 0.05). Also, cytotoxicity was evaluated in gastric adenocarcinoma (AGS), hepatocarcinoma (HepG2), and colon adenocarcinoma (SW620), with T. Atkins skin showing the best results (IC50 = 138–175 µg/mL). Finally, for AGS and SW 620 cell lines particularly, a high significant negative correlation was found between cytotoxic activity and gallotannins (r = −0.977 and r = −0.940, respectively) while for the HepG2 cell line, the highest significant negative correlation was found with xanthonoids compounds (r = −0.921).

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“…We have recently shown that EGCG inhibits FapC fibrillation even in the presence of bacterial amphiphiles such as rhamnolipids and LPS which otherwise promote fibrillation [29]. PGG is reported to have applications against cancer, diabetes, inflammation, neurodegeneration, viruses, and bacteria [30,31,32,33,34,35,36], but also inhibits aggregation. For example, it binds to the N-terminus and central hydrophobic core of Aβ 1–42 and Aβ 1–40 , decreasing formation of both oligomers and fibrils [37].…”

Section: Introductionmentioning

confidence: 99%

Plant Polyphenols Inhibit Functional Amyloid and Biofilm Formation in Pseudomonas Strains by Directing Monomers to Off-Pathway Oligomers

et al. 2019

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Self-assembly of proteins to β-sheet rich amyloid fibrils is commonly observed in various neurodegenerative diseases. However, amyloid also occurs in the extracellular matrix of bacterial biofilm, which protects bacteria from environmental stress and antibiotics. Many Pseudomonas strains produce functional amyloid where the main component is the highly fibrillation-prone protein FapC. FapC fibrillation may be inhibited by small molecules such as plant polyphenols, which are already known to inhibit formation of pathogenic amyloid, but the mechanism and biological impact of inhibition is unclear. Here, we elucidate how polyphenols modify the self-assembly of functional amyloid, with particular focus on epigallocatechin gallate (EGCG), penta-O-galloyl-β-d-glucose (PGG), baicalein, oleuropein, and procyanidin B2. We find EGCG and PGG to be the best inhibitors. These compounds inhibit amyloid formation by redirecting the aggregation of FapC monomers into oligomeric species, which according to small-angle X-ray scattering (SAXS) measurements organize into core-shell complexes of short axis diameters 25–26 nm consisting of ~7 monomers. Using peptide arrays, we identify EGCG-binding sites in FapC’s linker regions, C and N-terminal parts, and high amyloidogenic sequences located in the R2 and R3 repeats. We correlate our biophysical observations to biological impact by demonstrating that the extent of amyloid inhibition by the different inhibitors correlated with their ability to reduce biofilm, highlighting the potential of anti-amyloid polyphenols as therapeutic agents against biofilm infections.

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1,2,3,4,6-Penta-O-galloyl-β-d-glucose suppresses colon cancer through induction of tumor suppressor

Cited by 19 publications

References 35 publications

Biological and toxicological evaluation of Rhus trilobata Nutt. (Anacardiaceae) used traditionally in mexico against cancer

Biological and toxicological evaluation of Rhus trilobata Nutt. (Anacardiaceae) used traditionally in mexico against cancer

Polyphenolic Characterization, Antioxidant, and Cytotoxic Activities of Mangifera indica Cultivars from Costa Rica

Plant Polyphenols Inhibit Functional Amyloid and Biofilm Formation in Pseudomonas Strains by Directing Monomers to Off-Pathway Oligomers

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