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.

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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.

Olea europeae (L.) has been reported to have antibacterial, antifungal and antiviral activities. The aim of the present study is to evaluate antiviral activity of olive leaves extract (OLE) against herpes simplex viruses (HSV) type-1 virus. Screening of antiviral activity was assessed by measuring inhibition of viralinduced cytopathic effect of in vero cells of different OLE fractions that have been successively extracted using solvents of increasing polarities, against HSV type-1 virus. Negligible antiviral activity has been shown of different fractions, except for ethyl acetate and n-butanol fractions, showing strong and moderate anti-HSV type -1 activity, respectively. High performance liquid chromatography (HPLC) chromatographic analysis of both fractions revealed high oleuropein content in ethyl acetate fraction in addition to other phenolic and flavonoid contents, whereas n-butanol fraction showed only high content of other phenolic and flavonoid compounds. Cytotoxicity of ethyl acetate fraction was assessed in vero cell line, the mean cytotoxic concentration CC50, was reported to be 610 µg/ml. On the other hand, the 50% inhibitory concentration (IC50), against HSV-1, was of value as low as 40 µg/ml (SI = 15.2). This concentration could be more reduced to 33 µg/ml (SI = 16.9); that is, 17% reduction in dose, by formulating a microemulsion dosage form, with particle size of 13 to 19 nm, being assessed by Malvern Zetasizer Ver. 6.2 and electron microscopy. Acyclovir, a recommended anti-HSV agent, was used as a positive control. Oleuropein pure standard and the main phenolic component of OLE, was also assessed for its anti-HSV type-1 virus. As conclusion, microemulsion formulation enhanced antiviral activity of crude OLE.