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Isolation and Cytotoxic Activity of Phyllocladanes from the Roots of Acacia schaffneri (Leguminosae).

ABSTRACT: In research on natural molecules with cytotoxic activity that can be used for the development of new anticancer agents, the cytotoxic activity of hexane, chloroform, and methanol extracts from the roots of Acacia schaffneri against colon, lung, and skin cancer cell lines was explored. The hexane extract showed the best activity with an average IC50 of 10.6 µg mL-1. From this extract, three diterpenoids, phyllocladan-16?,19-diol (1), phyllocladan-16?-ol (2), and phylloclad-16-en-3-ol (3), were isolated and characterized by their physical and spectroscopic properties. Diterpenoids 1 and 2 were tested against the same cancer cell lines, as well as their healthy counterparts, CCD841 CoN, MRC5, and VH10, respectively. Compound 1 showed moderate activity (IC50 values between 24 and 70 ?g mL-1), although it showed a selective effect against cancer cell lines. Compound 2 was practically inactive. The cytotoxicity mechanism of 1 was analyzed by cell cycle, indicating that the compound induces G0/G1 cell cycle arrest. This effect might be generated by DNA alkylation damage. In addition, compound 1 decreased migration of HT29 cells.

SUBMITTER: Manriquez-Torres JJ

PROVIDER: S-EPMC7504352 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Isolation and Cytotoxic Activity of Phyllocladanes from the Roots of Acacia schaffneri (Leguminosae).

Manríquez-Torres José de Jesús JJ Hernández-Lepe Marco Antonio MA Chávez-Méndez José Román JR González-Reyes Susana S Serafín-Higuera Idanya Rubí IR Rodríguez-Uribe Genaro G Torres-Valencia Jesús Martín JM

Molecules (Basel, Switzerland) 20200828 17

In research on natural molecules with cytotoxic activity that can be used for the development of new anticancer agents, the cytotoxic activity of hexane, chloroform, and methanol extracts from the roots of Acacia schaffneri against colon, lung, and skin cancer cell lines was explored. The hexane extract showed the best activity with an average IC50 of 10.6 µg mL-1. From this extract, three diterpenoids, phyllocladan-16α,19-diol (1), phyllocladan-16α-ol (2</ ...[more]

PMID: 32872363

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Project description:Helicobacter pylori (H. pylori) is linked to the development of the majority of peptic ulcers and some types of gastric cancers, and its antibiotic resistance is currently found worldwide.This study is aimed at evaluating the anti-H. pylori activity of Korean acacia honey and isolating the related active components using organic solvents.The crude acacia honey was extracted with n-hexane, dichloromethane, ethyl acetate (EtOAc), and n-butanol. The EtOAc extract was subjected to octadecyl-silica chromatography. The extracts and fractions were then examined for anti-H. pylori activity using the agar well diffusion method. The antimicrobial activity of abscisic acid against H. pylori was investigated by determining the minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs), and by performing a time-kill assay.Abscisic acid related to the botanical origins of acacia honey from Korea has been analyzed using ultra-performance liquid chromatography. The MICs and MBCs of abscisic acid were 2.7 ± 1.3 and 6.9 ± 1.9 μg/mL, respectively. The bactericidal activity of abscisic acid (at 10.8 μg/mL corresponding to 4 × MIC) killed the organism within 36-72 h. These results suggest that abscisic acid isolated from Korean acacia honey has antibacterial activity against H. pylori.Abscisic acid isolated from Korean acacia honey can be therapeutic and may be further exploited as a potential lead candidate for the development of treatments for H. pylori-induced infections.The crude acacia honey was extracted with n-hexane, dichloromethane, EtOAc, and n-butanolThe EtOAc extract yielded eight fractions and four subfractions were subsequently obtained chromatographicallyAbscisic acid was isolated from one subfractionAll the solvent extracts and fractions showed antibacterial activity against H. pyloriAbscisic acid exhibited antibacterial activity against H. pylori. Abbreviations used: MeOH: Methanol; EtOAc: Ethyl acetate; TSB: Trypticase soy broth; MIC: Minimum inhibitory concentration; MBC: Minimum bactericidal concentration; CFU: Colony-forming units; UPLC: Ultra-performance liquid chromatography; DAD: Diode array detector; UV: Ultraviolet; ODS: Octadecyl-silica; MS: Mass spectrometry; SE: Standard error.

Project description:Acacia hydaspica possesses varied pharmacological attributes. We aimed to examine the antimicrobial potential and isolate the active antimicrobial metabolites. The plant extract was fractionated and the antimicrobial activity of the crude extract, fractions and compounds was tested by agar well diffusion and agar tube dilution and broth dilution methods. Bacterial strains selected for bioactivity testing were Staphylococcus aureus, Enterococcus faecalis, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Acinetobacter baumannii while selected strains from kingdom fungi were Candida albicans, Cryptococcus neoformans, Fusarium solani and Aspergillus. The active compounds were isolated from Acacia hydaspica by bioassay-guided fractionation and identified by nuclear magnetic resonance and spectroscopic techniques. S. aureus cell surface proteins, Autolysins (Atl), Clumping factor A (ClfA), and Fibronectin Binding Proteins (FnBP), were molecularly docked with Catechin 3-O-gallate (CG) and Methyl gallate (MG) and binding energy and molecular interactions between the proteins and compounds were analyzed. Ethyl acetate (AHE) and Butanol (AHB) fractions of A. hydaspica were the most active fractions against tested microbial strains. Therefore, both were subjected to bioassay-directed fractionation which led to the isolation of one pure active antimicrobial AHE and one active pure compound from AHB fraction besides active enriched isolates. Methyl-gallate (MG) and catechin-3-gallate (CG) are active compounds extracted from AHE and AHB fractions respectively. In antibacterial testing MG significantly inhibited the growth of E. coli (MIC50 = 21.5 µg/ml), B. subtilus (MIC50 = 23 µg/ml) and S. aureus (MIC50 = 39.1 µg/ml) while moderate to low activity was noticed against other tested bacterial strains. Antifungal testing reveals that MG showed potent antifungal activity against F. solani (MIC50 = 33.9 µg/ml) and A. niger (MIC50 = 41.5 µg/ml) while lower antifungal activity was seen in other tested strains. AHB fractions and pure compound (CG) showed specific antibacterial activity against S. aureus only (MIC50 = 10.1 µg/ml) while compound and enriched fractions showed moderate to no activity against other bacterial and fungal strains respectively. Molecular docking analysis revealed that CG interacted more strongly with the cell surface proteins than MG. Among these proteins, CG made a stronger complex with ClfA (binding affinity - 9.7) with nine hydrophobic interactions and five hydrogen bonds. Methyl gallate (MG) and catechin 3-O-gallate (CG) are the major antimicrobial compound from A. hydaspica that inhibit the growth of specific microbes. The occurrence of MG and CG endorse the traditional antimicrobial applicability of A. hydaspica, and it can be a legitimate alternative to control specific microbial infections.

Dataset Information

Isolation and Cytotoxic Activity of Phyllocladanes from the Roots of Acacia schaffneri (Leguminosae).

Publications

Isolation and Cytotoxic Activity of Phyllocladanes from the Roots of <i>Acacia schaffneri</i> (Leguminosae).

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