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Anti-Melanogenic Properties of Greek Plants. A Novel Depigmenting Agent from Morus alba Wood.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2017 Mar 23; Vol. 22 (4). Date of Electronic Publication: 2017 Mar 23. - Publication Year :
- 2017
-
Abstract
- In therapeutic interventions associated with melanin hyperpigmentation, tyrosinase is regarded as a target enzyme as it catalyzes the rate-limiting steps in mammalian melanogenesis. Since many known agents have been proven to be toxic, there has been increasing impetus to identify alternative tyrosinase inhibitors, especially from natural sources. In this study, we investigated 900 extracts from Greek plants for potential tyrosinase inhibitive properties. Among the five most potent extracts, the methanol extract of Morus alba wood (MAM) demonstrated a significant reduction in intracellular tyrosinase and melanin content in B16F10 melanoma cells. Bioassay-guided isolation led to the acquisition of twelve compounds: oxyresveratrol (1), kuwanon C (2), mulberroside A (3), resorcinol (4), dihydrooxyresveratol (5), trans-dihydromorin (6), 2,4,3'-trihydroxydihydrostilbene (7), kuwanon H (8), 2,4-dihydroxybenzaldehyde (9), morusin (10), moracin M (11) and kuwanon G (12). Among these, 2,4,3'-trihydroxydihydrostilbene (7) is isolated for the first time from Morus alba and constitutes a novel potent tyrosinase inhibitor (IC50 0.8 ± 0.15). We report here for the first time dihydrooxyresveratrol (5) as a potent natural tyrosinase inhibitor (IC50 0.3 ± 0.05). Computational docking analysis indicated the binding modes of six tyrosinase inhibitors with the aminoacids of the active centre of tyrosinase. Finally, we found both MAM extract and compounds 1, 6 and 7 to significantly suppress in vivo melanogenesis during zebrafish embryogenesis.
- Subjects :
- Animals
Cell Line, Tumor
Enzyme Inhibitors pharmacology
Hyperpigmentation drug therapy
Melanins biosynthesis
Melanoma drug therapy
Melanoma enzymology
Methanol chemistry
Methanol pharmacology
Mice
Molecular Docking Simulation
Plant Extracts chemistry
Plant Extracts isolation & purification
Plant Extracts pharmacology
Enzyme Inhibitors isolation & purification
Hyperpigmentation enzymology
Methanol isolation & purification
Monophenol Monooxygenase antagonists & inhibitors
Morus chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 22
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 28333105
- Full Text :
- https://doi.org/10.3390/molecules22040514