scholarly journals Novel Chemically Modified Curcumin (CMC) Derivatives Inhibit Tyrosinase Activity and Melanin Synthesis in B16F10 Mouse Melanoma Cells

Biomolecules ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 674
Author(s):  
Shilpi Goenka ◽  
Francis Johnson ◽  
Sanford R. Simon
Keyword(s):  
Enzyme Activity ◽  
Parent Compound ◽  
Radical Scavenging ◽  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Partial Recovery ◽  
Tyrosinase Inhibitor ◽  
Pyrocatechol Violet ◽  
Mouse Melanoma ◽  
Chemically Modified

Skin hyperpigmentation disorders arise due to excessive production of the macromolecular pigment melanin catalyzed by the enzyme tyrosinase. Recently, the therapeutic use of curcumin for inhibiting tyrosinase activity and production of melanin have been recognized, but poor stability and solubility have limited its use, which has inspired synthesis of curcumin analogs. Here, we investigated four novel chemically modified curcumin (CMC) derivatives (CMC2.14, CMC2.5, CMC2.23 and CMC2.24) and compared them to the parent compound curcumin (PC) for inhibition of in vitro tyrosinase activity using two substrates for monophenolase and diphenolase activities of the enzyme and for diminution of cellular melanogenesis. Enzyme kinetics were analyzed using Lineweaver-Burk and Dixon plots and nonlinear curve-fitting to determine the mechanism for tyrosinase inhibition. Copper chelating activity, using pyrocatechol violet dye indicator assay, and antioxidant activity, using a DPPH radical scavenging assay, were also conducted. Next, the capacity of these derivatives to inhibit tyrosinase-catalyzed melanogenesis was studied in B16F10 mouse melanoma cells and the mechanisms of inhibition were elucidated. Inhibition mechanisms were studied by measuring intracellular tyrosinase activity, cell-free and intracellular α-glucosidase enzyme activity, and effects on MITF protein level and cAMP maturation factor. Our results showed that CMC2.24 showed the greatest efficacy as a tyrosinase inhibitor of all the CMCs and was better than PC as well as a popular tyrosinase inhibitor-kojic acid. Both CMC2.24 and CMC2.23 inhibited tyrosinase enzyme activity by a mixed mode of inhibition with a predominant competitive mode. In addition, CMC2.24 as well as CMC2.23 showed a comparable robust efficacy in inhibiting melanogenesis in cultured melanocytes. Furthermore, after removal of CMC2.24 or CMC2.23 from the medium, we could demonstrate a partial recovery of the suppressed intracellular tyrosinase activity in the melanocytes. Our results provide a proof-of-principle for the novel use of the CMCs that shows them to be far superior to the parent compound, curcumin, for skin depigmentation.

scholarly journals Plumbagin Suppresses α-MSH-Induced Melanogenesis in B16F10 Mouse Melanoma Cells by Inhibiting Tyrosinase Activity

2017 ◽  
Vol 18 (2) ◽  
pp. 320 ◽  
Author(s):  
Taek-In Oh ◽  
Jeong-Mi Yun ◽  
Eun-Ji Park ◽  
Young-Seon Kim ◽  
Yoon-Mi Lee ◽  
...  
Keyword(s):  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Mouse Melanoma

scholarly journals SUPPRESSION OF PIGMENTATION IN MOUSE MELANOMA CELLS BY 5-BROMODEOXYURIDINE

1973 ◽  
Vol 57 (2) ◽  
pp. 406-423 ◽  
Author(s):  
Jean R. Wrathall ◽  
Constance Oliver ◽  
Selma Silagi ◽  
Edward Essner
Keyword(s):  
Gel Electrophoresis ◽  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Early Effect ◽  
Mouse Melanoma ◽  
Ultrastructural Evidence ◽  
Low Concentrations ◽  
Minor Part ◽  
B16 Mouse Melanoma

Low concentrations (1–3 µg/ml) of 5-bromodeoxyuridine (BrdU) reversibly suppress pigmentation in a highly pigmented clone (B559) of cultured B16 mouse melanoma cells. We have found that unpigmented cells (clone C3471), derived by long-term culture of B559 cells in 1 µg of BrdU/ml, were completely amelanotic with no biochemically or cytochemically detectable tyrosinase activity or ultrastructural evidence of premelanosomes. The process by which pigmentation is suppressed was studied in B559 cells during a 7-day period of growth with BrdU (3 µg/ml). Assays of tyrosinase activity showed that activity was reduced after 1 day and decreased progressively, approaching zero by 7 days. A quantitatively minor part of this reduction was directly attributable to the appearance of a dialyzable inhibitor of tyrosinase activity. Acrylamide gel electrophoresis revealed two bands of activity corresponding in Rx values to the T1 and T2 forms of soluble tyrosinase. Both were progressively reduced during growth with BrdU but one form (T1) was consistently affected earlier than the other (T2). Ultrastructural-cytochemical studies also showed an early effect on the localization of tyrosinase reaction product. At day 3, reaction product was no longer present in Golgi saccules and Golgi-associated smooth surfaced tubules, but was still seen within premelanosomes, compound melanosomes, and occasional Golgi-associated vesicles. By 7 days tyrosinase reaction product was usually not demonstrable. The number of premelanosomes was progressively decreased during growth with BrdU. Premelanosomes became concentrated in the juxtanuclear region and at day 3 many were contained within abnormally large and numerous compound melanosomes. Premelanosomes and compound melanosomes were rarely seen at 7 days, by which time the cultures were nearly amelanotic. The coordinated suppression of melanogenesis by BrdU may provide a useful model in which to study the normal regulation of this process.

scholarly journals Morin Induces Melanogenesis via Activation of MAPK Signaling Pathways in B16F10 Mouse Melanoma Cells

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2150
Author(s):  
SeoYeon Shin ◽  
JaeYeon Ko ◽  
MinJeong Kim ◽  
Nuri Song ◽  
KyungMok Park
Keyword(s):  
Protein Expression ◽  
Signaling Pathways ◽  
Molecular Mechanisms ◽  
Melanoma Cells ◽  
Mapk Signaling ◽  
Tyrosinase Activity ◽  
Melanin Biosynthesis ◽  
Mouse Melanoma ◽  
Melanin Contents ◽  
Mapk Signaling Pathways

Morin is a well-known flavonoid, and has been reported to have various properties, such as anti-cell death, antioxidant, and anti-inflammatory properties. Although studies on the biochemical and biological actions of morin have been reported, the melanin biosynthesis effects and molecular mechanisms are unknown. In this study, we first found that morin has the effect of enhancing melanin biosynthesis in B16F10 mouse melanoma cells, and analyzed the molecular mechanism. In this study, we examined the effects of morin on the melanin contents and tyrosinase activity, as well as the protein expression levels of the melanogenic enzymes TRP-1, TRP-2, and microphtalmia-associated transcription factor (MITF) in B16F10 mouse melanoma cells. Morin showed no cytotoxicity in the concentration range of 5–100 μM, and significantly increased the intracellular tyrosinase activity and melanin contents. In mechanism analysis, morin increased the protein expression of TRP-1, TRP-2, and MITF associated with melanogenesis. Furthermore, morin increased phosphorylated ERK and p38 at the early time, and decreased phosphorylated ERK after 12 h. The results suggest that morin enhances melanin synthesis through the MAPK signaling pathways in B16F10 mouse melanoma cells.

scholarly journals Skin Anti-aging Assays of Proanthocyanidin Rich Red Rice Extract, Oryzanol and Other Phenolic Compounds

2018 ◽  
Vol 13 (8) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Supachai Yodkeeree ◽  
Pilaiporn Thippraphan ◽  
Wanisa Punfa ◽  
Jatupol Srisomboon ◽  
Pornngarm Limtrakul(Dejkriengkraikul)
Keyword(s):  
Hyaluronic Acid ◽  
Bioactive Compounds ◽  
Vanillic Acid ◽  
Melanoma Cells ◽  
Skin Aging ◽  
Tyrosinase Activity ◽  
Hydroxybenzoic Acid ◽  
Red Rice ◽  
Mouse Melanoma ◽  
Aging Properties

Red rice is a variety of rice that has more nutritious than white or brown rice. It is also a good source of many potent anti-aging phytochemicals. However, the compounds in red rice extract that exhibit skin anti-aging properties have not been investigated. In this study, the main bioactive compounds in red rice extract (RRE) including proanthocyanidin, catechin, hydroxybenzoic acid, vanillic acid and oryzanol were studied in order to determine their anti-skin aging properties. The effects on skin degradation were assessed by inhibitory enzymatic activity against collagenase and matrixmetalloproteinase-2 (MMP-2). The production levels of collagen and hyaluronic acid obtained from human skin fibroblasts were determined by ELISA. Anti-melanogenesis activity of the bioactive compounds were investigated in B16-F10 mouse melanoma cells. The activity of collagenase and MMP-2 was strongly inhibited by proanthocyanidin and catechin, while hydroxybenzoic acid, vanillic acid and oryzanol had no effect. Moreover, proanthocyanindin and catechin significantly induced collagen and hyaluronic acid synthesis in human fibroblast cells. Proanthocyanidin and oryzanol reduced the melanin content in B16-F10 mouse melanoma cells. Proanthocyanidin, but not oryzanol, significantly decreased cellular tyrosinase activity. However, the bioactive compounds obtained from red rice extract had no effect on mushroom tyrosinase activity. In addition, proanthocynidin and catechin, exhibited strong DPPH radical scavenging activity, whereas oryzanol slightly inhibited this action. Taken together, these results suggest that proanthocyanidin, catechin, and oryzanol are the bioactive compounds in red rice that exhibit the greatest levels of anti-skin aging properties.

Proanthocyanidins purified from fruit pericarp of Clausena lansium (Lour.) Skeels as efficient tyrosinase inhibitors: structure evaluation, inhibitory activity and molecular mechanism

2017 ◽  
Vol 8 (3) ◽  
pp. 1043-1051 ◽  
Author(s):  
Wei-Ming Chai ◽  
Mei-Zhen Lin ◽  
Hui-Ling Feng ◽  
Zheng-Rong Zou ◽  
Ying-Xia Wang
Keyword(s):  
Molecular Mechanism ◽  
Inhibitory Activity ◽  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Mouse Melanoma ◽  
Fruit Pericarp ◽  
Tyrosinase Inhibitors ◽  
Structure Evaluation

The characterization, anti-tyrosinase activity and cytotoxicity against B16 mouse melanoma cells of proanthocyanidins purified from the fruit pericarp of C. lansium are reported.

Anti-melanogenesis properties of condensed tannins from Vigna angularis seeds with potent antioxidant and DNA damage protection activities

2019 ◽  
Vol 10 (1) ◽  
pp. 99-111 ◽  
Author(s):  
Wei-Ming Chai ◽  
Qi-Ming Wei ◽  
Wei-Liang Deng ◽  
Yun-Ling Zheng ◽  
Xiao-Ying Chen ◽  
...  
Keyword(s):  
Dna Damage ◽  
Condensed Tannins ◽  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Vigna Angularis ◽  
Mouse Melanoma ◽  
Dna Damage Protection ◽  
Damage Protection

The characterization, anti-tyrosinase activity, cytotoxicity against B16 mouse melanoma cells, antioxidant, and DNA damage protection activities of condensed tannins purified from Vigna angularis seeds were reported.

scholarly journals Inhibitory Effect of Elaeagnus umbellata Fractions on Melanogenesis in α-MSH-Stimulated B16-F10 Melanoma Cells

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1308
Author(s):  
Ji-Hyun Lee ◽  
Bori Lee ◽  
Yong-Deok Jeon ◽  
Hyun-Woo Song ◽  
Young-Mi Lee ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Radical Scavenging Activity ◽  
Skin Pigmentation ◽  
Radical Scavenging ◽  
Inhibitory Effect ◽  
Melanoma Cells ◽  
Tyrosinase Activity ◽  
Elaeagnus Umbellata ◽  
Melanocyte Stimulating Hormone ◽  
Related Proteins

When skin is exposed to UV radiation, melanocytes produce melanin. Excessive melanin production leads to skin pigmentation, which causes various cosmetic and health problems. Therefore, the development of safe, natural therapeutics that inhibit the production of melanin is necessary. Elaeagnus umbellata (EU) has long been widely used as a folk medicinal plant because of pharmacological properties that include anti-ulcer, antioxidant, and anti-inflammatory properties. In this study, we investigated the antioxidant activity and melanogenesis inhibitory effects of EU fractions in B16-F10 melanoma cells. EU fractions showed a dose-dependent increase in antioxidant activity in radical scavenging activity. In addition, we evaluated the effect of EU fractions on tyrosinase activity and melanogenesis in α-melanocyte-stimulating hormone-induced B16-F10 melanoma cells. EU was noncytotoxic at 12.5–50 μg/mL. EU fractions effectively inhibited tyrosinase activity and melanogenesis, suppressed the phosphorylation of CREB and ERK involved in the melanogenesis pathway, and down-regulated expression of melanogenesis-related proteins. Interestingly, the anti-melanogenesis effect was most effective at a concentration of 50 μg/mL EU, and the effects of the fractions were superior to those of the extract. Therefore, our study suggests that EU has potential as a safe treatment for excessive pigmentation or as a natural ingredient in cosmetics.

Sign in / Sign up

Export Citation Format

Share Document