Bio-Guided Fractionation of Prenylated Benzaldehyde Derivatives as Potent Antimicrobial and Antibiofilm from Ammi majus L. Fruits-Associated Aspergillus amstelodami.

Noha Fathallah,Marwa M Raafat,Mokhtar Bishr,Osama Salama,Marwa Y Issa,Mostafa A Abdelkawy,Marwa M Abdel-Aziz

doi:10.3390/molecules24224118

Abstract

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.

Highlights

Ammi majus (A. majus) L. of the family Umbellifereae/Apiaceae is an annual herbaceous plant which spreads in Egypt in the Nile and delta region [1], especially in Fayoum and Behira [2]
The isolated fungus belonged to Aspergillus genus depending on the morphological and microscopical characteristics described in Table 1 and Figure 1
Various approaches to discover new microorganisms are a serious problem nowadays resulting in high www.mdpi.com/journal/molecules compounds either with antimicrobial activity or enhancing the activity of the present antimicrobial mortality rate with accompanied community and nosocomial infections

Summary

Introduction

Ammi majus (A. majus) L. of the family Umbellifereae/Apiaceae is an annual herbaceous plant which spreads in Egypt in the Nile and delta region [1], especially in Fayoum and Behira [2]. It is distributed in the Mediterranean region of Europe, western Asia, and cultivated in India. It is known to contain biologically active compounds such as coumarins and flavonoids [3] It is usually utilized for the treatment of skin conditions such as psoriasis and vitiligo (acquired leukoderma) [4]. Essential oils specially are receiving growing interest as antimicrobial agents that retain high biocompatibility [6,7]

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