Anti-tyrosinase and antimelanogenic effect of cinnamic acid derivatives from Prunus mahaleb L.: Phenolic composition, isolation, identification and inhibitory activity
Yükleniyor...
Tarih
2023
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Elsevier Ireland Ltd.
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
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-β-glucopyranosyloxy-4-methoxyhydrocinnamic acid (1), cis-melilotoside (2), dihydromelilotoside (3), trans–melilotoside (4), 2-O-β-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 α-melanocyte-stimulating hormone (α-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.
Açıklama
Anahtar Kelimeler
Prunus mahaleb L., Cinnamic acid, Antityrosinase, Antimelanogenic, Enzyme kinetics, B16F10 melanoma
Kaynak
Journal of Ethnopharmacology
WoS Q Değeri
N/A
Scopus Q Değeri
Q1
Cilt
Sayı
310
Künye
Güven, Z. B., Saraçoğlu, İ., Nagatsu, A., Yılmaz, M. A. ve Başaran, A. A. (2023). Anti-tyrosinase and antimelanogenic effect of cinnamic acid derivatives from Prunus mahaleb L.: Phenolic composition, isolation, identification and inhibitory activity. Journal of Ethnopharmacology, (310), 1-11.
