Ammi majus L.; Family Apiaceae; is a plant indigenous to Egypt. Its fruits contain bioactive compounds such as furanocoumarins and flavonoids of important biological activities. An endophytic fungus was isolated from the fruits and identified as Aspergillus amstelodami (MK215708) by morphology, microscopical characterization, and molecular identification. To our knowledge this is the first time an endophytic fungus has been isolated from the fruits. The antimicrobial activity of the Ammi majus ethanol fruits extract (AME) and fungal ethyl acetate extract (FEA) were investigated, where the FEA showed higher antimicrobial activity, against all the tested standard strains. Phytochemical investigation of the FEA extract yielded five prenylated benzaldehyde derivative compounds isolated for the first time from this species: Dihydroauroglaucin (1), tetrahydroauroglaucin (2), 2-(3,6-dihydroxyhepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl)benzaldehyde (3), isotetrahydroauroglaucin )4), and flavoglaucin (5). Structure elucidation was carried out using (1H- and 13C-NMR). Fractions and the major isolated compound 1 were evaluated for their antimicrobial and antibiofilm activity. Compound 1 showed high antimicrobial activity against Escherichia coli with minimum inhibitory concentration (MIC) = 1.95 µg/mL, Streptococcus mutans (MIC = 1.95 µg/mL), and Staphylococcus aureus (MIC = 3.9 µg/mL). It exhibited high antibiofilm activity with minimum biofilm inhibitory concentration (MBIC) = 7.81 µg/mL against Staphylococcus aureus and Escherichia coli biofilms and MBIC = 15.63 µg/mL against Streptococcus mutans and Candida albicans and moderate activity (MBIC = 31.25 µg/mL) against Pseudomonas aeruginosa biofilm. This reveals that dihydroauroglaucin, a prenylated benzaldehyde derivative, has a broad spectrum antimicrobial activity. In conclusion, it was observed that the MICs of the FEA are much lower than that of the AME against all susceptible strains, confirming that the antimicrobial activity of Ammi majus may be due to the ability of its endophytic fungi to produce effective secondary metabolites.
Eradication of Helicobacter pylori is a challenge due to rising antibiotic resistance and GIT-related disorders. Cuminum cyminum, Pimpinella anisum, and Carum carvi are fruits belonging to the Apiaceae family. Their essential oils were extracted, analyzed using GC-MS, tested for anti-H. pylori activity by a micro-well dilution technique, identified for potential anti-H. pylori inhibitors by an in-silico study, and investigated for anti-inflammatory activity using a COX-2 inhibition assay. Results showed that the main components of C. cyminum, P. anisum, and C. carvi were cumaldehyde (41.26%), anethole (92.41%), and carvone (51.38%), respectively. Essential oil of C. cyminum exhibited the greatest anti-H. pylori activity (3.9 µg/mL) followed by P. anisum (15.63 µg/mL), while C. carvi showed the lowest activity (62.5 µg/mL). The in-silico study showed that cumaldehyde in C. cyminum has the best fitting energy to inhibit H. pylori.C. cyminum essential oil showed the maximum ability to reduce the production of Cox-2 expression approaching celecoxib with IC50 = 1.8 ± 0.41 µg/mL, followed by the C. carvi oil IC50 = 7.3 ± 0.35 µg/mL and then oil of P. anisum IC50 = 10.7±0.63 µg/mL. The investigated phytochemicals in this study can be used as potential adjunct therapies with conventional antibiotics against H. pylori.
Ammi majus L., an indigenous plant in Egypt, is widely used in traditional medicine due to its various pharmacological properties. We aimed to evaluate the anticancer properties of Ammi majus fruit methanol extract (AME) against liver cancer and to elucidate the active compound(s) and their mechanisms of action. Three fractions from AME (Hexane, CH2Cl2, and EtOAc) were tested for their anticancer activities against HepG2 cell line in vitro (cytotoxicity assay, cell cycle analysis, annexin V-FITC apoptosis assay, and autophagy efflux assay) and in silico (molecular docking). Among the AME fractions, CH2Cl2 fraction revealed the most potent cytotoxic activity. The structures of compounds isolated from the CH2Cl2 fraction were elucidated using 1H- and 13C-NMR and found that Compound 1 (xanthotoxin) has the strongest cytotoxic activity against HepG2 cells (IC50 6.9 ± 1.07 µg/mL). Treating HepG2 cells with 6.9 µg/mL of xanthotoxin induced significant changes in the DNA-cell cycle (increases in apoptotic pre-G1 and G2/M phases and a decrease in the S-phase). Xanthotoxin induced significant increase in Annexin-V-positive HepG2 cells both at the early and late stages of apoptosis, as well as a significant decrease in autophagic flux in cancer compared with control cells. In silico analysis of xanthotoxin against the DNA-relaxing enzyme topoisomease II (PDB code: 3QX3) revealed strong interaction with the key amino acid Asp479 in a similar fashion to that of the co-crystallized inhibitor (etoposide), implying that xanthotoxin has a potential of a broad-spectrum anticancer activity. Our results indicate that xanthotoxin exhibits anticancer effects with good biocompatibility toward normal human cells. Further studies are needed to optimize its antitumor efficacy, toxicity, solubility, and pharmacokinetics.
Endophytic Aspergillus species represent an inexhaustible source for many medicinally important secondary metabolites. The current study isolated the endophytic Aspergillus niger (OL519514) fungus from Opuntia ficus-indica fruit peels. The antibacterial activities were reported for both Aspergillus species and Opuntia ficus-indica fruit peel extract. Extraction of the endophytic fungal metabolites using ethyl acetate and fractionation was performed, yielding dihydroauroglaucin (C1), isotetrahydroauroglaucin (C2), and cristatumin B (C3). Resistant bacterial strains were used to investigate the efficiency of the total fungal ethyl acetate extract (FEA) and the isolated compounds. FEA showed promising wide spectrum activity. (C3) showed excellent activity against selected Gram-negative resistant bacteria; However, (C2) exhibited tremendous activity against the tested Gram-positive resistant strains; conversely, (C1) possessed the lowest antibacterial activity compared to the two other compounds. An in silico virtual molecular docking demonstrated that cristatumin B was the most active antimicrobial compound against the selected protein targets. In conclusion, the active metabolites newly isolated from the endophytic fungus Aspergillus niger (OL519514) and present in plants’ waste can be a promising antimicrobial agent against multidrug-resistant bacteria.
Due to its rising antibiotic resistance and associated inflammations, Helicobacter pylori poses a challenge in modern medicine. Salvia officinalis, a member of the Lamiaceae family, is a promising medicinal herb. In this regard, a phytochemical screening followed by GC-MS and LC-MS was done to evaluate the chemical profile of the total ethanolic extract (TES) and the essential oil, respectively. The anti-H. pylori and the anti-inflammatory activities were evaluated by a micro-well dilution technique and COX-2 inhibition assay. Potential anti-H. pylori inhibitors were determined by an in silico study. The results revealed that the main metabolites were flavonoids, sterols, volatile oil, saponins, and carbohydrates. The LC-MS negative ionization mode demonstrated 12 compounds, while GC-MS showed 21 compounds. Carnosic acid (37.66%), epirosmanol (20.65%), carnosol1 (3.3%), and 12-O-methyl carnosol (6.15%) were predominated, while eucalyptol (50.04%) and camphor (17.75%) were dominant in LC-MS and GC-MS, respectively. TES exhibited the strongest anti-H. pylori activity (3.9 µg/mL) asymptotic to clarithromycin (0.43 µg/mL), followed by the oil (15.63 µg/mL). Carnosic acid has the best-fitting energy to inhibit H. pylori (−46.6769 Kcal/mol). TES showed the highest reduction in Cox-2 expression approaching celecoxib with IC50 = 1.7 ± 0.27 µg/mL, followed by the oil with IC50 = 5.3 ± 0.62 µg/mL. Our findings suggest that S. officinalis metabolites with anti-inflammatory capabilities could be useful in H. pylori management. Further in vivo studies are required to evaluate and assess its promising activity.
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