Catalysis and inhibition of tyrosinase in the presence of cinnamic acid and some of its derivatives

García-Jiménez, Antonio; García‐Molina, Francisco; Teruel, José A.; Saura‐Sanmartin, Adrian; Garcı́a-Ruiz, Pedro Antonio; Ortiz-Lopez, Antonio; Rodrı́guez-López, José Neptuno; Garcı́a-Cánovas, Francisco; Muñoz‐Muñoz, José Luis

doi:10.1016/j.ijbiomac.2018.07.173

Cited by 41 publications

(19 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Caffeic acid was also significantly correlated with the inhibition of pentosidine-like AGEs formation (PCC = 0.825, p = 0.022). These results are in good agreement with literature data [5,7,20,78,79,87,96].…”

Section: Correlations Analysissupporting

confidence: 93%

“…Various studies are available in the literature documenting the anti-aging potential of elicited callus cultures of several plant species [35,86]. Caffeic acid and its derivatives have been reported as potent tyrosinase inhibitors [87], whereas esculetin and scopoletin showed significant potential toward the inhibition of collagenase [88,89].…”

Section: In Vitro Cell Free Anti-aging Assaysmentioning

confidence: 99%

See 1 more Smart Citation

Interactive Effects of Wide-Spectrum Monochromatic Lights on Phytochemical Production, Antioxidant and Biological Activities of Solanum xanthocarpum Callus Cultures

et al. 2020

View full text Add to dashboard Cite

Solanum xanthocarpum is considered an important traditional medicinal herb because of its unique antioxidant, and anti-diabetic, anti-aging, and anti-inflammatory potential. Because of the over exploitation linked to its medicinal properties as well as destruction of its natural habitat, S. xanthocarpum is now becoming endangered and its supply is limited. Plant in vitro culture and elicitation are attractive alternative strategies to produce biomass and stimulate biosynthesis of medicinally important phytochemicals. Here, we investigated the potential influence of seven different monochromatic light treatments on biomass and secondary metabolites accumulation in callus culture of S. xanthocarpum as well as associated biological activities of the corresponding extracts. Among different light treatments, highest biomass accumulation was observed in white light-treated callus culture. Optimum accumulation of total flavonoid contents (TFC) and total phenolic contents (TPC) were observed in callus culture kept under continuous white and blue light respectively than control. Quantification of phytochemicals through HPLC revealed that optimum production of caffeic acid (0.57 ± 0.06 mg/g DW), methyl-caffeate (17.19 mg/g ± 1.79 DW), scopoletin (2.28 ± 0.13 mg/g DW), and esculetin (0.68 ± 0.07 mg/g DW) was observed under blue light callus cultures. Compared to the classic photoperiod condition, caffeic acid, methyl-caffeate, scopoletin, and esculetin were accumulated 1.7, 2.5, 1.1, and 1.09-folds higher, respectively. Moreover, high in vitro cell free antioxidant, anti-diabetic, anti-aging, and anti-inflammatory activities were closely associated with the production of these secondary metabolites. These results clearly showed the interest to apply multispectral light as elicitor of in vitro callus cultures S. xanthocarpum to promote the production of important phytochemicals, and allow us to propose this system as an alternative for the collection of this endangered species from the wild.

show abstract

Section: Correlations Analysissupporting

confidence: 93%

Section: In Vitro Cell Free Anti-aging Assaysmentioning

confidence: 99%

Interactive Effects of Wide-Spectrum Monochromatic Lights on Phytochemical Production, Antioxidant and Biological Activities of Solanum xanthocarpum Callus Cultures

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Results of the compounds in the presence of 4-tert-butylcatechol (TBC) showed that compounds 1, 91, 93, 94 and 95 are competitive inhibitors whereas compounds 46, 47 and 88 are substrates of tyrosinase. The inhibition constants were affected by the ability of the substituent group to increase the charge on the benzene ring [81]. The methoxy group, OCH3 is an electron donor and it increased the charge on the benzene ring making the inhibition constant to be in the order 95 ˃ 93 ˃ 91 ˃ 1.…”

Section: Cinnamic Acid Derivatives With Antioxidant and Anti-inflammamentioning

confidence: 99%

Section: Cinnamic Acid Derivatives With Antioxidant and Anti-inflamentioning

confidence: 99%

“…The methoxy group, OCH 3 is an electron donor and it increased the charge on the benzene ring making the inhibition constant to be in the order 95 ˃ 93 ˃ 91 ˃ 1 . Tyrosinase could not hydroxylate compound 94 but was able to hydroxylate compound 88 because compound 94 has a great distance for ligand hydroxylation while compound 88 has a distance feasible for hydroxylation [ 81 ].…”

Section: Cinnamic Acid Derivatives With Antioxidant and Anti-inflamentioning

confidence: 99%

See 1 more Smart Citation

Cinnamic Acid Derivatives and Their Biological Efficacy

Ruwizhi

Aderibigbe

2020

IJMS

201

View full text Add to dashboard Cite

The role played by cinnamic acid derivatives in treating cancer, bacterial infections, diabetes and neurological disorders, among many, has been reported. Cinnamic acid is obtained from cinnamon bark. Its structure is composed of a benzene ring, an alkene double bond and an acrylic acid functional group making it possible to modify the aforementioned functionalities with a variety of compounds resulting in bioactive agents with enhanced efficacy. The nature of the substituents incorporated into cinnamic acid has been found to play a huge role in either enhancing or decreasing the biological efficacy of the synthesized cinnamic acid derivatives. Some of the derivatives have been reported to be more effective when compared to the standard drugs used to treat chronic or infectious diseases in vitro, thus making them very promising therapeutic agents. Compound 20 displayed potent anti-TB activity, compound 27 exhibited significant antibacterial activity on S. aureus strain of bacteria and compounds with potent antimalarial activity are 35a, 35g, 35i, 36i, and 36b. Furthermore, compounds 43d, 44o, 55g–55p, 59e, 59g displayed potent anticancer activity and compounds 86f–h were active against both hAChE and hBuChE. This review will expound on the recent advances on cinnamic acid derivatives and their biological efficacy.

show abstract

Comparing the effect of benzoic acid and cinnamic acid hydroxyl derivatives on polyphenol oxidase: activity, action mechanism, and molecular docking

et al. 2022

View full text Add to dashboard Cite

BACKGROUND: Polyphenol oxidase (PPO) is considered to have a key role in the food industry because it initiates enzymatic browning in the processing and storage of fruit and vegetables. Increasing numbers of benzoic and cinnamic acid derivatives have been found to be efficient inhibitors of polyphenol oxidase, but a comparison study on activity and action mechanism is lacking. In this study, 18 benzoic acid and cinnamic acid hydroxy derivatives were selected and investigated. RESULTS: Three substrates, four activators and 11 inhibitors were identified from benzoic and cinnamic acid derivatives. 2,4-Dihydroxy-cinnamic acid and benzoic acid showed the strongest inhibitory effect on PPO, with IC 50 of 0.092 and1.425 mmol L −1 , respectively. Benzoic acid reversibly inhibited PPO in a competitive manner, while 2,4-dihydroxycinnamic acid showed a mixed-type inhibition. Both of them showed that static-type fluorescence quenching and electrostatic interaction were the main driving force in the bonding process. Compared with benzoic acid, 2,4-dihydroxycinnamic acid more easily formed hydrogen bonds in the active site of PPO, making the interaction more stable. CONCLUSION: Comparative analysis showed that the inhibition effect of cinnamic acid hydroxyl derivatives on PPO was stronger than that of benzoic acid derivatives. Benzoic acid and 2,4-dihydroxycinnamic acid were the strongest inhibitors. PPO inhibitors identified from benzoic and cinnamic acid derivatives are expected to be promising inhibitors for controlling fruit and vegetable browning.

show abstract

Catalysis and inhibition of tyrosinase in the presence of cinnamic acid and some of its derivatives

Cited by 41 publications

References 38 publications

Interactive Effects of Wide-Spectrum Monochromatic Lights on Phytochemical Production, Antioxidant and Biological Activities of Solanum xanthocarpum Callus Cultures

Interactive Effects of Wide-Spectrum Monochromatic Lights on Phytochemical Production, Antioxidant and Biological Activities of Solanum xanthocarpum Callus Cultures

Cinnamic Acid Derivatives and Their Biological Efficacy

Comparing the effect of benzoic acid and cinnamic acid hydroxyl derivatives on polyphenol oxidase: activity, action mechanism, and molecular docking

Contact Info

Product

Resources

About