Hypolaetin-7-O-β-D-xyloside from Juniperus communis Fruits Inhibits Melanogenesis on Zebrafish Pigmentation

Abstract

Hypolaetin-7-O--D-xyloside (1) is a naturally occurring flavonoid from Juniperus communis fruits. This study aimed to investigate anti-melanogenic effect of hypolaetin-7-O--D-xyloside on zebrafish pigmentation. The phenotype-based image analysis suggested that 1 suppressed the zebrafish pigmentation in a concentration-dependent manner (1-400 M) as a reversible competitive inhibitor against the enzyme tyrosinase. According to the molecular docking simulation, the compound 1 interacted with residues His-263 of tyrosinase via hydrogen bonding. The present study provided direct experimental evidence for skin-lightening effect of 1 in an in vivo zebrafish model. Therapeutic attempts with the 1 might be useful in the management of skin pigmentation-related diseases.

Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides

“…Terpene xylosides (Figure 1A-D) are commonly found in various herbs used in folk medicine, which, in addition to such properties for use as an anti-inflammatory or their ability to treat hot flashes during menopause, are also credited with the ability to treat Alzheimer's disease. [11], (B) Actaea asiatica [12], (C) Homonoia riparia [13] and (D) Actaea racemose [14]; Another type of naturally occurring D-xylopyranosides are derivatives containing polycyclic aromatic compounds such as aglycone [15][16][17]. Quercetin, a natural flavonol, is among the most common aglycones of this type (Figure 1E).…”

“…The obtained results of biological tests showed that two of the tested compounds, including the β-D-xylofuranose derivative, turned out to be very interesting and were to be submitted for further research. Another type of naturally occurring D-xylopyranosides are derivatives containing polycyclic aromatic compounds such as aglycone [15][16][17]. Quercetin, a natural flavonol, is among the most common aglycones of this type (Figure 1E).…”

Ionomic Parameters of Populations of Common Juniper (Juniperus communis L.) Depending on the Habitat Type

“…Juniperus communis is a very ornamental species providing special value to the landscape [ 3 ], and its stands are a beloved subject for recreation in Baltic countries, especially in Lithuania [ 16 , 17 ]. Compounds extracted from J. communis have been assessed using model species or tissue cultures for potential use in veterinary care and medicine, e.g., effects on Freund’s adjuvant-induced arthritis in rats [ 20 ], melanogenesis on zebrafish pigmentation [ 21 ], in human SH-SY5Y neuroblastoma cells in relation to diabetes [ 22 ], and showing in vitro antioxidant, genotoxic and cytotoxic activities [ 23 ]. Juniperus communis needles, seeds (usually titled as berries), and bark are used in veterinary and folk medicine for the treatment of respiratory diseases [ 24 , 25 , 26 ], diabetes [ 22 ], and inflammatory diseases [ 27 ], and also as antibacterial and antifungal agents [ 28 , 29 ].…”