Synthesis of natural benzoin/benzil analogs, biological activity studies, isolation and characterization of secondary metabolites produced by Fusarium sp. YP9B

In the first part of the thesis, benzoin (1-29), benzil (30-50) and stilbene (51-62) derivatives were synthesized. Antioxidant, enzyme inhibition, antimicrobial activities (against 18 different microorganism) for the all synthesized compounds (1-62) and anticancer screening tests for compounds 4, 15, 25, and 35 against HeLa and RPE-1, as well as compounds 4, 15, 22, 23a+b, 24a+b, 25, 26, 27, 28, 29a+b, 35, 45, 46, 47, 48, 49 and 50 were performed against MCF7, HT29, C6 and Hep3B. Compounds 29a+b, 50, and 43 were found to be the most effective antioxidant against FRAP, CUPRAC, and DPPH method, respectively. Antimicrobial activities of 1-62 showed that compounds 6a+b, 26 and 33 were found to be most effective against Staphylococcus aureus, Streptococcus mutans, Bacillus cereus and Mycobacterium smegmatis within the range of 9-12 µg/mL MIC. Compounds 7, 26, 46, 22, and 26 showed as much activity as the standards against α-amylase, α-glucosidase, acetylcholinesterase, butyrylcholinesterase and tyrosinase enzymes, respectively. Four most bioactive compounds (4, 15, 25, and 35) were tested against the HeLa and RPE-1. Compounds 4 and 25 were found to be more effective than cis-platinum against HeLa and RPE-1. Compounds 47, 28, 46 were the most effective against C6, Hep3B/HT29, and MCF7, respectively. In the second part of the thesis, 10 new secondary metabolites produced by Fusarium oxysporum YP9B strain, were isolated and characterized by spectroscopic methods. The antimicrobial MIC and MBC doses of the isolated compounds against 13 different microorganisms were determined. Compounds FO-1, FO-4a-c and FO-5 showed 0.94 µg/mL, 2.1 µg/mL, and 0.8 µg/mL MIC values against B. cereus, respectively. Among the isolated compounds FO-1, FO-4a-c and FO-5 showed anticancer activities against MCF-7, PC-3, and A549. Compound FO-1 was found to be most effective against MCF-7 with an IC50 value of 15.01±4.55 µM, and compounds FO-4a-c were found to be most effective against A549 with an IC50 value of 7.51±1.38 µM. All synthesized and isolated compounds were characterized by spectroscopic methods and by the help of ACD NMR program.