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1,3,6-Trigalloylglucose: A Novel Potent Anti-Helicobacter pylori Adhesion Agent Derived from Aqueous Extracts of Terminalia chebula Retz.

ABSTRACT: 1,3,6-Trigalloylglucose is a natural compound that can be extracted from the aqueous extracts of ripe fruit of Terminalia chebula Retz, commonly known as "Haritaki". The potential anti-Helicobacter pylori (HP) activity of this compound has not been extensively studied or confirmed in scientific research. This compound was isolated using a semi-preparative liquid chromatography (LC) system and identified through Ultra-high-performance liquid chromatography-MS/MS (UPLC-MS/MS) and Nuclear Magnetic Resonance (NMR). Its role was evaluated using Minimum inhibitory concentration (MIC) assay and minimum bactericidal concentration (MBC) assay, scanning electron microscope (SEM), inhibiting kinetics curves, urea fast test, Cell Counting Kit-8 (CCK-8) assay, Western blot, and Griess Reagent System. Results showed that this compound effectively inhibits the growth of HP strain ATCC 700392, damages the HP structure, and suppresses the Cytotoxin-associated gene A (Cag A) protein, a crucial factor in HP infection. Importantly, it exhibits selective antimicrobial activity without impacting normal epithelial cells GES-1. In vitro studies have revealed that 1,3,6-Trigalloylglucose acts as an anti-adhesive agent, disrupting the adhesion of HP to host cells, a critical step in HP infection. These findings underscore the potential of 1,3,6-Trigalloylglucose as a targeted therapeutic agent against HP infections.

SUBMITTER: Ou L

PROVIDER: S-EPMC10935070 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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1,3,6-Trigalloylglucose: A Novel Potent Anti-Helicobacter pylori Adhesion Agent Derived from Aqueous Extracts of Terminalia chebula Retz.

Ou Ling L Zhu Zhixiang Z Hao Yajie Y Li Qingwei Q Liu Hengrui H Chen Qingchang Q Peng Chang C Zhang Chuqiu C Zou Yuanjing Y Jia Junwei J Li Hui H Wang Yanhua Y Su Bingmei B Lai Yuqian Y Chen Meiyun M Chen Haobo H Feng Zhong Z Zhang Guimin G Yao Meicun M

Molecules (Basel, Switzerland) 20240305 5

1,3,6-Trigalloylglucose is a natural compound that can be extracted from the aqueous extracts of ripe fruit of Terminalia chebula Retz, commonly known as "Haritaki". The potential anti-Helicobacter pylori (HP) activity of this compound has not been extensively studied or confirmed in scientific research. This compound was isolated using a semi-preparative liquid chromatography (LC) system and identified through Ultra-high-performance liquid chromatography-MS/MS (UPLC-MS/MS) ...[more]

PMID: 38474673

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Project description:Antimicrobial resistance (AMR) has arisen due to antibiotic overuse and misuse. Antibiotic resistance renders standard treatments less effective, making it difficult to control some infections, thereby increasing morbidity and mortality. Medicinal plants are attracting increased interest as antibiotics lose efficacy. This study evaluates the antibacterial activity of solvent extracts prepared using Terminalia bellirica and Terminalia chebula fruit against six bacterial pathogens using disc diffusion and broth microdilution assays. The aqueous and methanol extracts of T. bellirica and T. chebula showed substantial zones of inhibition (ZOIs) against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA). The activity against those bacteria was strong, with minimum inhibitory concentrations (MIC) ranging from 94 µg/mL to 392 µg/mL. Additionally, the T. bellirica methanolic extract showed noteworthy antibacterial activity against Escherichia coli and an extended spectrum β-lactamase (ESBL) E. coli strain (MIC values of 755 µg/mL for both). The aqueous T. bellirica and T. chebula extracts also inhibited Klebsiella pneumoniae growth (MIC values of 784 µg/mL and 556 µg/mL, respectively). The corresponding methanolic extracts also inhibited ESBL K. pneumoniae growth (MIC values of 755 µg/mL and 1509 µg/mL, respectively). Eighteen additive interactions were observed when extracts were combined with reference antibiotics. Strong antagonism occurred when any of the extracts were mixed with polymyxin B. Liquid chromatography-mass spectroscopy (LC-MS) analysis of the extracts revealed several interesting flavonoids and tannins, including 6-galloylglucose, 1,2,6-trigalloyl-β-D-glucopyranose, 6-O-[(2E)-3-phenyl-2-propenoyl]-1-O-(3,4,5-trihydroxybenzoyl)-β-D-glucopyranose, propyl gallate, methyl gallate, sanguiin H4, hamamelitannin, pyrogallol, gallic acid, ellagic acid, chebulic acid, and chebuloside II. All extracts were nontoxic in brine shrimp assays. This lack of toxicity, combined with their antibacterial activities, suggests that these plant species may be promising sources of antibacterial compound(s) that warrant further study.

Project description:BackgroundBurgeoning antibiotic resistance in Pseudomonas aeruginosa has necessitated the development of anti pathogenic agents that can quench acylhomoserine lactone (AHL) mediated QS with least risk of resistance. This study explores the anti quorum sensing potential of T. chebula Retz. and identification of probable compounds(s) showing anti QS activity and the mechanism of attenuation of P. aeruginosa PAO1 virulence factors.Methods and resultsMethanol extract of T. chebula Retz. fruit showed anti QS activity using Agrobacterium tumefaciens A136. Bioactive fraction (F7), obtained by fractionation of methanol extract using Sephadex LH20, showed significant reduction (p<0.001) in QS regulated production of extracellular virulence factors in P. aeruginosa PAO1. Biofilm formation and alginate were significantly (p<0.05) reduced with enhanced (20%) susceptibility to tobramycin. Real Time PCR of F7 treated P. aeruginosa showed down regulation of autoinducer synthase (lasI and rhlI) and their cognate receptor (lasR and rhlR) genes by 89, 90, 90 and 93%, respectively. Electrospray Ionization Mass Spectrometry also showed 90 and 64% reduction in the production of 3-oxo-C(12)HSL and C(4)HSL after treatment. Decrease in AHLs as one of the mechanisms of quorum quenching by F7 was supported by the reversal of inhibited swarming motility in F7-treated P. aeruginosa PAO1 on addition of C(4)HSL. F7 also showed antagonistic activity against 3-oxo-C(12)HSL-dependent QS in E. coli bioreporter. C. elegans fed on F7-treated P. aeruginosa showed enhanced survival with LT50 increasing from 24 to 72 h. LC-ESI-MS of F7 revealed the presence of ellagic acid derivatives responsible for anti QS activity in T. chebula extract.ConclusionsThis is the first report on anti QS activity of T. chebula fruit linked to EADs which down regulate the expression of lasIR and rhlIR genes with concomitant decrease in AHLs in P. aeruginosa PAO1 causing attenuation of its virulence factors and enhanced sensitivity of its biofilm towards tobramycin.

Project description:BackgroundA study carried out by World Health Organization revealed that around 80% of individuals globally depends on herbal forms of medication with 40% of pharmaceutical products being sourced from medicinal plants. The study objective was to evaluate the phytochemicals composition, in vitro antimicrobial and antioxidant properties of the leaves of Terminalia catappa L. aqueous and methanolic extracts.MethodsAntimicrobial activity was analyzed by disk diffusion, the minimum inhibitory concentration in-vitro assays with ciprofloxacin as the standard for antibacterial assay while nystatin for antifungal assay. Ferric reducing antioxidant power and 2,2-diphenyl-1-picryl-hydrazyl-hydrate assays were used for the evaluation of antioxidant properties of the crude extracts while the groups responsible for this activity identified using Fourier transform infrared spectrophotometer.ResultsThe study found that the leaves of Terminalia catappa contained alkaloids, tannins, steroids, cardiac glycosides, flavonoids, phenols, saponins, and coumarins, but terpenoids were absent. Presence of functional groups associated with this class of compounds such as OH vibrational frequencies were observed in IR spectrum of the crude extracts. Methanolic extract from Terminalia catappa exhibited greater antibacterial properties against Pseudomonas aeruginosa, Escherichia coli and Staphylococcus aureus, whereas aqueous extract displayed greater antibacterial activity against Bacillus subtilis for all concentrations tested. The amount of the sample that scavenged 50 percent of DPPH (IC50) was found to be 8.723, 13.42 and 13.04 µg/mL for L-ascorbic acid, Terminalia catappa L. methanolic and aqueous extracts respectively. The antimicrobial and antioxidant activities varied with the extract concentration and solvent used in extractions.ConclusionTerminalia catappa L. leaves are prospective for use as a source of therapeutic agents that could lead to the advancement of new antimicrobial and antioxidant products.

Dataset Information

1,3,6-Trigalloylglucose: A Novel Potent Anti-Helicobacter pylori Adhesion Agent Derived from Aqueous Extracts of Terminalia chebula Retz.

Publications

1,3,6-Trigalloylglucose: A Novel Potent Anti-<i>Helicobacter pylori</i> Adhesion Agent Derived from Aqueous Extracts of <i>Terminalia chebula</i> Retz.

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