Thesis (Ph.D.) - Cairo University - Faculty of Pharmacy - Department of Pharmacognosy

Ammi majus L., family Apiaceae growing in Egypt is famous for comprising active constituents as coumarins, flavonoids, and steroids. Its main used part is the fruits that contain furanocoumarins widely used in skin conditions like vitiligo and psoriasis. Firstly: This study is meant to investigate the bioactive metabolites present in the aerial parts (waste) in comparison with that of the fruits and optimize the cultivation conditions to enhance the constituents present in the fruits. Optimization was via exposure to drought stress and applying an exogenous phytohormone (ethephon) then comparing the results with that of the control fruit group. The physical parameters besides the differences in the total phenolics, total flavonoid contents, and the antioxidant activity of the extracts were evaluated. Remarkably, the aerial parts revealed higher total phenolics and flavonoids with much stronger antioxidant activity than the fruit extract. The positive and negative metabolic profiling using UPLC/MS-MS of the aerial parts extract revealed different compounds when compared to the compounds present in the fruits. Secondly: The Ammi majus, fruits were investigated for their phytochemical compounds responsible for their pharmacological activities.The dried powdered plant was extracted with methanol, fractionated using gradient elution then the CH₂Cl₂ fraction was purified using puri-flash.The compounds isolated were identified using 1HNMR and 13CNMR as Ý-sitosterol, Isoarnottinin, Xanthotoxin, Marmesin, Imperatorin, and Ammirin. Thirdly: An endophytic fungus was isolated from the fruits and identified as Aspergillus amstelodami (MK215708). After mass production of the fungus on rice media, the active metabolites were extracted using EtOAc then fractionated and purified using preparative HPLC to give Dihydroauroglaucin, tetrahydroauroglaucin, 2-(3,6-dihydroxyhepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl) benzaldehyde, isotetrahydroauroglaucin), flavoglaucin and, 2-(2, 3-epoxy-1,3,5-heptatrienyl)-6-hydroxy-5-(3-methyl-2-butenyl) benzaldehyde. Structure elucidation was carried out using (¹ H-and ¹³ C-NMR, HMBC, HSQC, and COSY)

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