title: Tyrosinase inhibitory constituents from a polyphenol enriched fraction of rose oil distillation wastewater.
abstract: During the water steam distillation process of rose flowers, the non-volatile phenolic compounds remain in the waste. We recently developed a strategy to separate rose oil distillation water (RODW) into a polyphenol depleted water fraction and a polyphenol enriched fraction (RF20-SP207). Bioassay-guided investigation of RF20-SP207 led to the isolation of quercetin, kaempferol and ellagic acid. Their structures were elucidated by spectroscopic analysis as well as by comparison with literature data. Tyrosinase inhibition studies were performed with RF20-SP207, fractions I-IV, and the isolated compounds of the most active fraction. RF20-SP207 strongly inhibited the enzyme with an IC50 of 0.41 μg/mL. From the tested fractions only fraction IV (IC50=5.81 μg/mL) exhibited strong anti-tyrosinase activities. Quercetin, kaempferol and ellagic acid were identified in fraction IV and inhibited mushroom tyrosinase with IC50 values of 4.2 μM, 5.5 μM and 5.2 μM, respectively, which is approximately 10 times more potent than that of the positive control kojic acid (56.1μM). The inhibition kinetics, analyzed by Lineweaver-Burk plots, indicated that RF20-SP207 and fraction IV are uncompetitive inhibitors of tyrosinase when l-tyrosine is used as a substrate. A mixed inhibition was determined for ellagic acid, and a competitive inhibition for quercetin and kaempferol. In conclusion, the recovered polyphenol fraction RF20-SP207 from RODW was found to be a potent tyrosinase inhibitor. This value-added product could be used as an active ingredient in cosmetic products related to hyperpigmentation.
authors.affiliation: Institute for Pharma Technology, School of Life Sciences, University of Applied Sciences Northwestern Switzerland, Gründenstrasse 40, CH-4132 Muttenz, Switzerland.
authors.forename: Jessica
authors.initials: J
authors.lastname: Solimine
authors.affiliation: Institute of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056, Basel, Switzerland.
authors.forename: Eliane
authors.initials: E
authors.lastname: Garo
authors.affiliation: Institute for Pharma Technology, School of Life Sciences, University of Applied Sciences Northwestern Switzerland, Gründenstrasse 40, CH-4132 Muttenz, Switzerland.
authors.forename: Jonas
authors.initials: J
authors.lastname: Wedler
authors.affiliation: AgroBioInstitute, Agriculture Academy, Dragan Tzankov 8, Sofia 1164, Bulgaria.
authors.forename: Krasimir
authors.initials: K
authors.lastname: Rusanov
authors.affiliation: Institute of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056, Basel, Switzerland.
authors.forename: Orlando
authors.initials: O
authors.lastname: Fertig
authors.affiliation: Institute of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056, Basel, Switzerland.
authors.forename: Matthias
authors.initials: M
authors.lastname: Hamburger
authors.affiliation: AgroBioInstitute, Agriculture Academy, Dragan Tzankov 8, Sofia 1164, Bulgaria.
authors.forename: Ivan
authors.initials: I
authors.lastname: Atanassov
authors.affiliation: Institute for Pharma Technology, School of Life Sciences, University of Applied Sciences Northwestern Switzerland, Gründenstrasse 40, CH-4132 Muttenz, Switzerland. Electronic address: veronika.butterweck@fhnw.ch.
authors.forename: Veronika
authors.initials: V
authors.lastname: Butterweck
mesh_terms: D000363:Agaricales / Q000201:enzymology; D057168:Distillation; D004610:Ellagic Acid / Q000737:chemistry; D035264:Flowers / Q000737:chemistry; D044949:Kaempferols / Q000737:chemistry; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D059808:Polyphenols / Q000737:chemistry*; D011794:Quercetin / Q000737:chemistry; D027826:Rosa / Q000737:chemistry*; D062065:Wastewater / Q000737:chemistry*
chemical_list: D004610:Ellagic Acid; D044949:Kaempferols; D014442:Monophenol Monooxygenase; D059808:Polyphenols; D011794:Quercetin; D062065:Wastewater; C006552:kaempferol
keywords: Ellagic acid; Hyperpigmentation; Rosa damascena; Rosaceae; Rose oil distillation; Tyrosinase inhibition