Eczacılık Fakültesi / Faculty of Pharmacy

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search.filters.applied.f.rights: search.filters.rights.info:eu-repo/semantics/closedAccessSubject: search.filters.subject.Prunus mahaleb L.

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    Anti-Tyrosinase and Antimelanogenic Effect of Cinnamic Acid Derivatives from Prunus Mahaleb L.: Phenolic Composition, Isolation, Identification And Inhibitory Activity
    (2023) Guven, Zuhal Bayrakceken; Saracoglu, Iclal; Nagatsu, Akito; Yilmaz, Mustafa Abdullah; Basaran, A. Ahmet; 36924865; AAI-6606-2021
    Ethnopharmacological relevance: The traditional use of Prunus species against skin diseases and especially for skin lightning cosmeceutical purposes is widespread in many cultures. Prunus mahaleb L. is a well known food plant and used in the baking industry for flavoring. The fruit kernels (endocarp) are used in India for hyperpigmentation. Aim of the study: To investigate the chemical composition with the antimelanogenesis effect of P. mahaleb seed and kernel extracts and isolated compounds. Materials and methods: Isolation studies performed from the methanol extracts obtained from kernels and structures were determined using NMR and MS analysis. Antimelanogenesis effect was determined by mushroom tyrosinase assay, cellular tyrosinase assay and melanin content assay using B16F10 murine melanoma cells. Results: Five cinnamic acid derivatives were isolated and their structures (2-O-& beta;-glucopyranosyloxy-4-methoxyhydrocinnamic acid (1), cis-melilotoside (2), dihydromelilotoside (3), trans-melilotoside (4), 2-O-& beta;-glucosyloxy4-methoxy trans-cinnamic acid (5)) were elucidated using advanced spectroscopic methods. Mushroom tyrosinase enzyme inhibition of extracts, fractions and pure compounds obtained from P. mahaleb kernels were investigated and structure-activity relationship revealed. According to a detailed, comprehensive and validated LC-MS/MS technique analysis, vanilic acid (41.407 mg/g), protocatechuic acid (8.992 mg/g) and ferulic acid (4.962 mg/g) in the kernel ethylacetate fraction; quinic acid (14.183 mg/g), fumaric acid (8.349 mg/g) and aconitic acid (5.574 mg/g) were found as major phenolic compounds in the water fraction. The correlation of trace element copper content in extracts and fractions with mushroom enzyme activity was determined. By examining the enzyme kinetics of the compounds with effective cinnamic acid derivatives, inhibition types and enzyme binding constants Ki were calculated. Compounds 1,3 and 5 exhibited high noncompetitive tyrosinase inhibitory activity against L-tyrosine substrates, with IC50 values of 0.22, 0.31 and 0.37 mM respectively. In addition compounds 1, 3 and 5 showed dose-dependent inhibitory effects on intracellular tyrosinase and melanin levels in & alpha;-melanocyte-stimulating hormone (& alpha;-MSH)-induced B16F10 melanoma cells. Conclusions: Potent tyrosinase inhibitory compounds and extracts of P. mahaleb kernels suggest that it could be a new, non-toxic and inexpensive resource for the cosmeceutical industry and in skin diseases associated with hyperpigmentation.
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    Food plant with antioxidant, tyrosinase inhibitory and antimelanoma activity: Prunus mahaleb L
    (2022) Guven, Zuhal Bayrakceken; Dogan, Zeynep; Saracoglu, Iclal; Picot, Laurent; Nagatsu, Akito; Basaran, A. Ahmet
    Prunus mahaleb L. seeds are used as spice and folk remedies in many countries. The aim of this study was bioactivity guided isolation and characterization phytoconstituents of P. mahaleb which have been studied very limited so far. The antioxidant capacities of seed and kernel (endocarp) extracts were studied by DPPH, nitric oxide (NO), superoxide (SO), TEAC, CUPRAC methods. The antiproliferative activity were investigated for the first time against B16F10, A2058, HeLa and L929 cell lines using MTT assay. Gallic acid and ursolic acid which have strong antioxidant and cell growth inhibitory effect, were isolated from the most active fractions. From the inactive fractions, quercetin-3-O(2-O,6-O-alpha-dirhamnopyranosyl beta-glucopyranoside), kaempferol-3-O(2-O,6-O alpha-dirhamnopyranosyl beta-glucopyranoside) and beta-sitosterol-3-O-beta-glucopyranoside were isolated. Our study is the first record for the isolation of ursolic acid from all parts of P. mahaleb, gallic acid from P. mahaleb kernels, two flavonol triglycosides from the Prunus species and their analysis by advanced NMR spectroscopic methods. Ursolic acid (IC50 : 170.2 mu M) and gallic acid (IC50 : 10.5 mu M) showed strong tyrosinase inhibition, gallic acid being 5.4 times more effective than standard compound. Kernel extracts have strong antioxidant activity, showed high growth inhibitory activity with dose-dependent manner on melanoma cells but no growth inhibitory on healthy L929 and HeLa cancer cells. The high antioxidant capacity of kernel, its selective growth inhibition of B16F10 and A2058 melanoma cells and its strong tyrosinase inhibitory compounds suggest that it could be a new, non-toxic and inexpensive resource for melanoma treatment and cosmetic industry.