Structure–activity relationships of various amino-hydroxy-benzenesulfonic acids and sulfonamides as tyrosinase substrates

Rescigno, Antonio; Bruyneel, Frédéric; Padiglia, Alessandra; Sollai, Francesca; Salis, Andrea; Marchand‐Brynaert, Jacqueline; Sanjust, Enrico

doi:10.1016/j.bbagen.2011.05.002

Cited by 19 publications

(10 citation statements)

References 38 publications

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“…Tyrosinase inhibition: As being the largest groups in tyrosinase inhibitors and flavanoids, polyphenols are widely distributed in the leaves, seeds, bark and flowers of plants 21 . Among these plants, walnut has been reported to be rich in flavonoids and phenolic acid and therefore, it is an excellent example to be developed as a tyrosinase inhibitor 22,23 .…”

Section: Resultsmentioning

confidence: 99%

Total Phenols, Antioxidant Potential and Tyrosinase Inhibitory Activity of Walnut (Juglans regia L.) Leaf, Husk and Seed

Akin¹,

Arabaci²,

Şaki³

2013

Asian J. Chem.

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There has been growing interest over the discovery and utilization of antioxidants from natural sources such as fruits and vegetables, because several studies have documented the potential toxicity associated with the synthetic antioxidants. Most antioxidants are phenolic substances, in fact, it has been shown that there is a direct relationship between the total phenolic content and antioxidant activity in fruits and vegetables. Also, the remarkable tyrosinase inhibitory activities of polyphenols have been reported by several studies 1,2. Recent epidemiological studies have suggested that increased consumption of plant-derived, antioxidant-rich foods, decrease the risk of degenerative diseases by reduction of oxidative stress and inhibition of macromolecular oxidation 3,4. In addition, they have also been used in food and cosmetic industry by the inhibition of tyrosinase enzyme and there is a serious effort to search for natural tyrosinase inhibitors like plants because they are free of harmful side effects and can be obtained at a low cost 5-7. Among the dietary plants, walnut (Juglans regia L.) is a well-known member of Juglandaceae family. It has a remarkable nutritional composition with rich phenolic compounds. Different studies have proved that isolated polyphenols obtained from walnuts have strong antioxidant effects and they are commonly consumed in Turkey 8-10 .

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Section: Resultsmentioning

confidence: 99%

Total Phenols, Antioxidant Potential and Tyrosinase Inhibitory Activity of Walnut (Juglans regia L.) Leaf, Husk and Seed

Akin¹,

Arabaci²,

Şaki³

2013

Asian J. Chem.

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“…Based on the broad substrate spectrum, in principle, any simple monophenol or corresponding catechol appears to be its substrate [38]. Besides, TYR also oxidizes various aromatic amines, o-aminophenols, and aromatic o-diamines (Figure 5), despite the reaction rates being orders of magnitude smaller than the corresponding phenols or catechol [39,40]. In terms of phenols, mammalian TYR tends to be relatively specific for its physiological substrate (L-tyrosine and L-DOPA) and has a higher affinity for the L-isomers [41].…”

Section: Substrate Specificity Of Tyrmentioning

confidence: 99%

Spectrophotometric Assays for Sensing Tyrosinase Activity and Their Applications

et al. 2021

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Tyrosinase (TYR, E.C. 1.14.18.1), a critical enzyme participating in melanogenesis, catalyzes the first two steps in melanin biosynthesis including the ortho-hydroxylation of L-tyrosine and the oxidation of L-DOPA. Previous pharmacological investigations have revealed that an abnormal level of TYR is tightly associated with various dermatoses, including albinism, age spots, and malignant melanoma. TYR inhibitors can partially block the formation of pigment, which are always used for improving skin tone and treating dermatoses. The practical and reliable assays for monitoring TYR activity levels are very useful for both disease diagnosis and drug discovery. This review comprehensively summarizes structural and enzymatic characteristics, catalytic mechanism and substrate preference of TYR, as well as the recent advances in biochemical assays for sensing TYR activity and their biomedical applications. The design strategies of various TYR substrates, alongside with several lists of all reported biochemical assays for sensing TYR including analytical conditions and kinetic parameters, are presented for the first time. Additionally, the biomedical applications and future perspectives of these optical assays are also highlighted. The information and knowledge presented in this review offer a group of practical and reliable assays and imaging tools for sensing TYR activities in complex biological systems, which strongly facilitates high-throughput screening TYR inhibitors and further investigations on the relevance of TYR to human diseases.

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“…Eight vic ‐substituted o ‐aminophenols belonging to 2 isomeric series were investigated for their tyrosinase inhibitory activity by Rescigno and others (2011). Four o ‐aminophenolic compounds derived from the 3‐hydroxyorthanilic acid scaffold and their 4 counterparts derived from the isomeric 2‐hydroxymethanilic acid were investigated as mushroom tyrosinase inhibitors.…”

Section: Synthetic Compoundsmentioning

confidence: 99%

Natural and Synthetic Tyrosinase Inhibitors as Antibrowning Agents: An Update

Loizzo

Tundis

Menichini

2012

Comp Rev Food Sci Food Safe

276

170

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Tyrosinase (EC 1.14.18.1), a copper-containing enzyme, can cause enzymatic browning in raw fruits, vegetables, and beverages. Browning is an undesirable reaction that is responsible for less attractive appearance and loss in nutritional quality. These phenomena have encouraged researchers to seek new potent tyrosinase inhibitors for use in the food industry. This article reviews recent studies on tyrosinase inhibitors of natural and synthetic origins. The information offered here should help food industry in developing and using potential tyrosinase inhibitors desirable efficacy and safety, and for improving food quality.

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Structure–activity relationships of various amino-hydroxy-benzenesulfonic acids and sulfonamides as tyrosinase substrates

Cited by 19 publications

References 38 publications

Total Phenols, Antioxidant Potential and Tyrosinase Inhibitory Activity of Walnut (Juglans regia L.) Leaf, Husk and Seed

Total Phenols, Antioxidant Potential and Tyrosinase Inhibitory Activity of Walnut (Juglans regia L.) Leaf, Husk and Seed

Spectrophotometric Assays for Sensing Tyrosinase Activity and Their Applications

Natural and Synthetic Tyrosinase Inhibitors as Antibrowning Agents: An Update

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