Summary:
In the present dissertation, various methods for the production of extracts of industrial hemp C. sativa L. with high phenolic extra virgin olive oil (HPEVOO) were studied and evaluated. After applying some of the most common extraction procedures found in literature, the secoiridoid phenolic compounds of the extracts were quantified, and the content of cannabidiol and cannabidiolic acid was measured, using a one-dimension quantitative nuclear magnetic resonance spectroscopy (1D qNMR) method. The best extraction method was indicated, where phenols and cannabinoids were both maintained at optimal levels. During the extraction processes, the formation of a pyridine alkaloid, methyl 5-vinylnicotinate, was observed. The compound was isolated from the extracts using low-pressure adsorption chromatography and preparative thin layer chromatography and identified using NMR and GC-MS. After various tests, a possible mechanism of formation of methyl 5-vinylnicotinate was proposed, through the reaction of a phenolic compound of olive oil with a source of nitrogen of cannabis, under heating. Furthermore, it was found that methyl 5-vinylnicotinate was formed, during thermal processing (cooking) of some plant and animal foods with olive oil, after testing food-olive oil extracts with NMR. The plant food sources that were examined were onion, garlic, pepper, mushroom and carrot and the animal food sources were cheese, bacon and egg. In addition, different food-olive oil ratios were evaluated. At a next step, we performed the semi-synthesis of methyl 5-vinylnicotinate by two methods. In the first method, dry phenolic extract of extra virgin olive oil, dissolved in DMSO, reacted with ammonium hydroxide, under heating. In the second method, pure oleomissional, isolated from olive tree leaves, dissolved in DMSO, reacted with ammonium hydroxide, under heating. This was followed by acid-alkaline liquid-liquid extractions with HCl and NH4OH, for purification of the reaction’s product, and isolation of pure methyl 5-vinylnicotinate by column adsorption chromatography. In addition to methyl 5-vinylnicotinate, pure hydroxytyrosol acetate was isolated by column chromatography and tyrosol acetate by column chromatography, followed by HPLC-UV. The substances were identified using 1D 1H-NMR spectroscopy and GC-MS.
Keywords:
C. sativa L., O. europaea L., EVOO, HPEVOO, CBD, CBDA, methyl 5-vinylnicotinate, oleomissional, hydroxytyrosol acetate
