Thiosemicarbazones as inhibitors of tyrosinase enzyme

Soares, Mariana Alves; Almeida, Mariana Ramos; Marins-Goulart, Carla; Chaves, Otávio Augusto; Echevarrı́a, Aurea; Oliveira, Márcia C.C. de

doi:10.1016/j.bmcl.2017.05.057

Cited by 44 publications

(18 citation statements)

References 21 publications

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“…Over the past years, a number of tyrosinase inhibitors have been known, and some of them are currently in use to reduce skin hyperpigmentation. However, there is still an increasing demand for more effective and safer tyrosinase inhibitors, predominantly originating from plants (Qin et al, 2015; Soares et al, 2017). All the studied extracts had showed remarkable inhibitory capacity against tyrosinase.…”

Section: Resultsmentioning

confidence: 99%

Novel insights into the fruit and seed extracts ofMorinda morindoides(Baker) Milne‐Redh: HPLC‐ESI‐Q‐TOF‐MS profiling, antioxidant, and enzyme inhibitory propensities

et al. 2020

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In this study, we attempted for the first time to determine the phytochemical compositions and biopharmaceutical properties of the methanolic and aqueous extracts of Morinda morindoides fruits and seeds. Antioxidant propensities of the extracts were determined via free radical‐scavenging, phosphomolybdenum, metal chelating, and reducing power assays. Inhibitory activities against cholinesterases (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)), tyrosinase, α‐amylase, and α‐glucosidase were assessed. Moreover, the total phenolic and flavonoid contents were determined. High Performance Liquid Chromatography coupled to Electrospray Ionization Quadrupole Time‐of‐Flight Mass Spectrometry (HPLC‐ESI‐Q‐TOF‐MS) analysis was performed to establish the chemical profile of the investigated extracts. The tested extracts showed remarkable antioxidant abilities with aqueous fruit extract being most potent in all assays, except for ferrous ion chelating assay. Overall, the methanolic extracts were potent inhibitors of the tested enzymes. In conclusion, M. morindoides may be endorsed as promising sources of bioactive compounds and used for designing functional foods. Practical applications In recent years, new compounds from plant sources have attracted great interest to design functional foods. Thus, we aimed to detect biological and chemical properties of Morinda morindoides fruits and seeds, a widely used as food with medicinal properties in Africa. Based on our findings, fruits extracts exhibited stronger activity when compared to seed extracts. Also, chemical identification was performed for each extracts. The presented findings could provide valuable information into the pool of scientific knowledge and may be basis for the design of novel functional applications from M. morindoides.

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Section: Resultsmentioning

confidence: 99%

Novel insights into the fruit and seed extracts ofMorinda morindoides(Baker) Milne‐Redh: HPLC‐ESI‐Q‐TOF‐MS profiling, antioxidant, and enzyme inhibitory propensities

et al. 2020

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“…Several kinds of thiosemicarbazone derivatives 38 , 34 , 364–376 has been investigated as possible tyrosinase inhibitors (Figure 11). Furthermore, some benzaldehyde derivatives of thiosemicarbazone such as chlorobenzaldehyde thiosemicarbazones 363 , p -hydroxy and p -methoxy benzaldehyde thiosemicarbazone 362 along with p -methoxybenzaldehyde thiosemicarbazone and 4-dimethylaminobenzaldehyde-thiosemicarbazone and 4-dimethylaminobenzaldehyde-N-phenyl-thiosemicarbazone 377 were evaluated for their inhibitory activities on mushroom tyrosinase.…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

745

471

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Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

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“…Consequently, tyrosinase plays a pivotal role in melanin formation, which is an important component responsible for skin pigmentation in humans. Although melanin produced in skin melanocytes provides protection from UV radiation, excessive accumulation of melanin may cause cosmetic flaws such as age spots, freckles, senile lentigines, solar lentigo, and melasma in humans (Germanò et al, 2012;Hridya et al, 2016;Soares et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Inhibition of Tyrosinase by Mercury Chloride: Spectroscopic and Docking Studies

Chen

Ran

et al. 2020

Front. Pharmacol.

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Inorganic mercury compounds have been used in skin-lightening products since ancient times. Although a previous study demonstrated that mercury impeded the transfer of Cu 2+ to the apotyrosinase, the effect of mercury on tyrosinase is still unclear. In the present study, the mechanism of mercury chloride (HgCl 2) induced inactivation of tyrosinase was investigated for the first time. The IC 50 values were 29.97 and 77.93 mmol/L for monophenolase and diphenolase, respectively. A kinetic analysis revealed that HgCl 2 inhibited tyrosinase activity in an irreversible non-competitive manner. The strong intrinsic fluorescence quenching suggested that the formation of the HgCl 2-tyrosinase complex induced conformational changes of the enzyme, and HgCl 2 had only one single binding site or a single class of binding site on tyrosinase. The molecular docking and further experiments demonstrated that HgCl 2 bound to the amino residuals (His) in the catalytic center of tyrosinase. To our knowledge, these findings presented in this paper were the first evidence of the direct interactions between HgCl 2 and tyrosinase, which provided a deep understanding of the inhibition mechanism of mercury on tyrosinase.

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Thiosemicarbazones as inhibitors of tyrosinase enzyme

Cited by 44 publications

References 21 publications

Novel insights into the fruit and seed extracts ofMorinda morindoides(Baker) Milne‐Redh: HPLC‐ESI‐Q‐TOF‐MS profiling, antioxidant, and enzyme inhibitory propensities

Novel insights into the fruit and seed extracts ofMorinda morindoides(Baker) Milne‐Redh: HPLC‐ESI‐Q‐TOF‐MS profiling, antioxidant, and enzyme inhibitory propensities

A comprehensive review on tyrosinase inhibitors

Inhibition of Tyrosinase by Mercury Chloride: Spectroscopic and Docking Studies

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