Inhibitory effect of brazilein on tyrosinase and melanin synthesis: Kinetics and  in silico  approach

Hemachandran, Hridya; Anantharaman, Amrita; Mohan, Sankari; Doss, C. George Priya; Gopalakrishnan, Mahesh; Gopalakrishnan, Chandrasekhar; Siva, Ramamoorthy

doi:10.1016/j.ijbiomac.2015.07.064

Cited by 57 publications

(37 citation statements)

References 34 publications

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“…Chelation of copper ions by adjacent hydroxyl groups on the B ring has also been suggested as a feasible inhibition mechanism for proanthocyanidins [101,102,106]. Copper chelation as well as hydrophobic and hydrogen bonding within the active site resulting in secondary structural changes have been validated for brazilein, too [190]. Generally, the number and location of phenolic hydroxyl groups significantly affect the tyrosinase inhibitory activity in the case of flavonoids [62].…”

Section: Structural Requirements For the Design Of Tyrosinase Inhibitorsmentioning

confidence: 99%

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed.

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Section: Structural Requirements For the Design Of Tyrosinase Inhibitorsmentioning

confidence: 99%

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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“…Although the decrease in the number of OH group should have caused an increase in the intensity of C=O 3 band at 1,365 cm −1 , the results showed that the intensities of C=O as well as C=C 21,44 bands at 1595 cm −1 and C-H band in the aromatic ring 3 within the wavenumber range of 860-650 cm −1 in the spectra of the powder prepared from the solutions at pH 7 and 9 heated at 100 °C for 60 min decreased. Change in the pattern of www.nature.com/scientificreports/ aliphatic C-H band 43 at around 2,980-2,845 cm −1 was also observed. These might be due to the degradation of the deprotonated brazilein (form 2 and/or form 3) after heating at a higher temperature for an extended period of time.…”

Section: Resultsmentioning

confidence: 86%

Color and molecular structure alterations of brazilein extracted from Caesalpinia sappan L. under different pH and heating conditions

Ngamwonglumlert

Devahastin

Chiewchan

et al. 2020

Sci Rep

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Brazilein extract from sappan wood (Caesalpinia sappan L.) has potential for use as natural food colorant since it has no unique flavor and taste. Although brazilein has long been applied in several traditional foods and beverages, information on its stability, which is of importance for practical application, is still limited. In this work, brazilein was isolated from sappan wood; its purity was confirmed by nuclear magnetic resonance spectroscopy. Relations between molecular structures and color as well as thermal stabilities of brazilein in aqueous solutions at pH 3, 7 and 9 were for the first time investigated. At the lowest pH, zero net-charge structure of brazilein, which exhibited yellow color, was predominantly found. The deprotonated and fully deprotonated structures of brazilein, which exhibited orange and red colors, respectively, were found when pH of the aqueous solutions increased. The forms of brazilein existing at the higher pH suffered extensive degradation upon heating, while the form existing at the lowest pH possessed higher stability. Heat-induced deprotonation and degradation were confirmed by UV-visible and Fourier-transform infrared spectra as well as losses of brazilein content. Sappan (Caesalpinia sappan L.), which has several such local names as Buckham wood in English, Bois de sappan in French, Pau de sappan in Polish, Sappanholz in German, Su mu in Chinese, Suo in Japanese and Fang in Thai, is a wood in the family Leguminosae. This wood is naturally available throughout Asia, including China, Japan and Thailand. Due to its several valuable functions, this wood plant is also nowadays cultivated in various other regions of the world, including Africa, Europe as well as North and South Americas. Dried heartwood of sappan has long been used as herbal medicines as it contains many phytochemicals and bioactive compounds 1-5. The biological abilities of the wood extract in terms of antiacne 6 , anti-bacterial 7,8 , anticancer 9 , antidiabetic 10 , antidiarrhea 11 , antiinflammatory 12-14 , antioxidant 15 and anti-photoaging 16 activities have been demonstrated by a number of researchers. The major active ingredient of sappan is brazilin, which is a colorless phenolic compound consisting of two aromatic rings, one pyrone and one five-membered ring. Based on its molecular structure, brazilin is identified as a neoflavonoid. However, hydroxyl group in the brazilin structure is easily oxidized and can change into carbonyl group, resulting in the structural transformation and formation of brazilein, which is a colored compound 17-19. Brazilein has indeed widely been used as a natural colorant; sappan extract containing brazilein has traditionally been used in the painting of books as well as in the dyeing of silk and wool. Since an aqueous extract of sappan possesses many beneficial properties over other red-color pigments, e.g.

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“…Thus, the major change of PPO conformation is that the α‐helix is translated into a random coil. The change in the helical structure of PPO may cause unfolding of the polypeptide chain and also exposure of the hydrophobic region …”

Section: Resultsmentioning

confidence: 99%

Acidic electrolysed water delays browning by destroying conformation of polyphenoloxidase

et al. 2017

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Inhibitory effect of brazilein on tyrosinase and melanin synthesis: Kinetics and in silico approach

Cited by 57 publications

References 34 publications

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Color and molecular structure alterations of brazilein extracted from Caesalpinia sappan L. under different pH and heating conditions

Acidic electrolysed water delays browning by destroying conformation of polyphenoloxidase

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