Phytochemical and bioactivity studies of prangos aricakensis (Apiaceae) plant

Prangos aricakensis is an endemic plant species belonging to the Apiaceae family. In this study, crude extracts of leaf (PAY), fruit (PAM), root (PAK) and stem (PAS) were obtained with extraction of P. aricakensis (PA) plant. Leaf oil (PAYUY), fruit oil (PAMUY), root oil (PAKUY) and stem oil (PASUY) were also collected with Clevenger type apparatus. A bioguided approach was carried out by separating each crude extract into fractions and then sub-fractions by chromatographic methods. The structures of 6 different isolates (trans-cinnamic acid, rutin, oxypeucedanin, osthol, sucrose and daucosterol) were clarified by NMR analyzes and also molecular mass values determined by MS analysis. In addition, FT-IR and X-ray crystallography analyzes carried out for osthol molecule, which obtained in crystal form. The isolated compounds trans-cinnamic acid and daucosterol were isolated for the first time in Prangos species (from P. aricakensis plant). The analyzes of phenolics and essential oils of the extracts were performed by LC-MS/MS and GC-MS/MS. Bioactivities of crude extracts, essential oils, fractions, sub-fractions and isolates were determined by antioxidant (total antioxidant, DPPH∙ scavenging and ABTS∙+ scavenging), enzyme inhibition (acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase and urease), antimicrobial (minimum inhibition concentration (MIC) method), DNA protection activities. Principal component analysis were carried out between the fractions and experiments. Statistical analyzes were made and results were compared with standard drug molecules. In addition to these, isolate-enzyme interactions invastigated with "Molecular Docking" technique and enzyme kinetics studies were carried out. As a result of phytochemical analysis, it was seen that the most effective extract was PAY extract, the total phenolic content value was calculated as 26.37±2.10 mg gallic acid equivalent/g and the total flavonoid content was calculated as 15.64±0.07 mg quercetin equivalent/g. Among the samples, the most effective total antioxidant activity was daucosterol (34.69±0.22 µg/mL). The most effective DPPH∙ scavenging activity was PAYUY (2.12±0.84 µg/mL), oxypeucedanin (2.19±0.38 µg/mL) and daucosterol (2.92±0.29 µg/mL). According to the enzyme inhibition results, the best extract was PAY, for Alzheimer's disease (PAY9, 3.05±1.78 µg/mL for AChE and PAY10, 0.98±0.01 µg/mL for BChE), for skin protective effect (PAY63, 2.30±1.25 µg/mL for tyrosinase). MIC results showed that all crude extracts were more effective than antibiotics against K. pneumonia. Within the framework of these results, it was observed that P. aricakensis plant showed good antioxidant activity, enzyme inhibition properties, DNA protection activity and its isolates also showed strong interactions with enzymes.