Primerjava različnih eteričnih olj navadnega komarčka (Foeniculum vulgare) s plinsko kromatografijo, sinteza derivatov anisaldehida in vrednotenje z vonjalnim testom

Janežič, Nina (author), Obreza, Aleš (mentor)

Navadni komarček (Foeniculum vulgare) je aromatično zelišče, ki se od nekdaj uporablja v različne namene. Poznamo dve glavni varieteti, in sicer sladki in grenki komarček. Brezbarvno do bledo rumeno eterično olje komarčka je predvsem v plodovih rastline in je sestavljeno iz številnih monoterpenov in fenilpropidov. Glavne spojine v eteričnem olju komarčka so anetol, estragol in fenkon. V eksperimentalnem delu naloge smo s kolonsko adsorpcijsko kromatografijo skušali izolirati anetol iz komercialno dostopnega eteričnega olja navadnega komarčka. Analiza izolirane frakcije z anetolom s plinsko kromatografijo, sklopljeno z masno spektrometrijo je pokazala, da izolacija ni uspela, saj je bila sestava tega vzorca precej podobna sestavi izvornega eteričnega olja. Nato smo z destilacijo z vodno paro iz droge doma pridelanega sladkega komarčka in iz droge grenkega komarčka, ki ustreza Evropski farmakopeji, izolirali eterični olji. S plinsko kromatografijo, sklopljeno z masno spektrometrijo smo primerjali sestave obeh pridobljenih eteričnih olj in komercialno dostopnega eteričnega olja. Obe izolirani eterični olji sta ustrezali pogojem Evropske farmakopeje, medtem ko je komercialno dostopno eterično olje rahlo odstopalo od zahtevanih pogojev. Vsa tri eterična olja so si bila po kvalitativni sestavi precej podobna, kvantitativno pa so se razlikovala. V nadaljevanju smo s klasičnimi metodami organske kemije sintetizirali nekaj hlapnih derivatov anisaldehida, ki je ena izmed spojin v eteričnem olju komarčka. Identiteto produktov smo potrdili s spektroskopskimi metodami. Nato smo z vonjalnim testom vrednotili prijetnost in jakost vonja sintetiziranih spojin in vseh treh eteričnih olj. Izkazalo se je, da so imela eterična olja močnejši vonj kot sintezne spojine. Vonjalna analiza je pokazala tudi, da se je vonj komercialno dostopnega eteričnega olja in eteričnega olja, izoliranega iz doma pridelanega komarčka, večini preiskovancem zdel prijeten. Od sintetiziranih hlapnih derivatov anisaldehida pa jih je večina označila za prijetnega le enega. Na koncu smo izdelali hidrogel z eteričnim oljem navadnega komarčka, ki pa je že nekaj tednov kasneje začel kazati znake razrasta mikroorganizmov, kar pomeni, da eterično olje v dodani količini ni zagotavljalo zadostne protimikrobne zaščite.

• Language: Slovenian
• Keywords: eterično olje, navadni komarček, anetol, anisaldehid, vonjalni test
• Work type: Bachelor thesis/paper
• Organization: FFA - Faculty of Pharmacy
• Year: 2019
• PID: 20.500.12556/RUL-109646
• Publication date in RUL: 06.09.2019

Secondary language

• Language: English
• Title: Comparsion of different essential oils of fennel (Foeniculum vulgare) with gas chromatography, synthesis of anisaldehyde derivatives and evaluation with smell test

Abstract

Fennel (Foeniculum vulgare) is an aromatic herb which has been used for multiple purposes for centuries. Two main varieties are sweet and bitter fennel. Colourless to pale yellow fennel essential oil is usually in the fruit of the plant and consists of many monoterpenes and phenylpropenes. The main components of fennel essential oil are anethole, estragole and fenchone. In the experimental part of the thesis we tried to isolate anethole from commercially available fennel essential oil with column adsorption chromatography. Gas chromatography coupled with mass spectrometry analysis showed that isolation was not successful due to similarity of isolated anethole to original essential oil. Essential oils from home grown sweet fennel and Ph. Eur. bitter fennel were isolated by hydrodistillation. The isolated essential oils and commercially available essential oil were compared based on gas chromatography coupled with mass spectrometry analysis. Both isolated essential oils correspond to regulations of the European Pharmacopoeia whereas commercial essential oil does not. All three essential oils have quite similar qualitative composition however they differ quantitively. We synthesized volatile derivatives of anisaldehyde, which is one of the components in fennel essential oil. Products' identities were confirmed by spectroscopic methods. Smell test was used to evaluate pleasantness and intensity of synthesized compounds and all three essential oils. It turned out that the smell of essential oils is more intense than of the synthesized compounds. Most people found smell of commercially available essential oil and essential oil isolated from home grown fennel pleasant. Smell of only one volatile anisaldehyde derivative was found pleasant. The hydrogel with fennel essential oil was made and it started showing signs of microorganisms’ growth few weeks after making. That means fennel essential oil in added amount does not provide sufficient antimicrobial protection.

• Keywords: essential oil, fennel, anethole, anisaldehyde, smell test