3‐<i>O</i>‐Glyceryl‐2‐<i>O</i>‐hexyl ascorbate suppresses melanogenesis by interfering with intracellular melanosome transport and suppressing tyrosinase protein synthesis

Taira, Norihisa; Katsuyama, Yushi; Yoshioka, Masato; Okano, Yasuaki; Hashimoto, Masaki

doi:10.1111/jocd.12451

Cited by 10 publications

(7 citation statements)

References 38 publications

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“…As shown in Table 2 , none of the AsA derivatives showed inhibitory activity when using either l -tyrosine or l -DOPA as substrates. In addition, in mammalian tyrosinase testing, compound 6 did not show activity when using l -DOPA as substrates [ 49 ], and this result was similar to that observed in the mushroom tyrosinase test ( Figure 6 ). This suggests that tyrosinase inhibition is not involved in the mechanisms of action of these melanogenesis inhibitors.…”

Section: Resultssupporting

confidence: 61%

Structural Requirements of Alkylglyceryl-l-Ascorbic Acid Derivatives for Melanogenesis Inhibitory Activity

Taira

Katsuyama²,

Yoshioka³

et al. 2018

IJMS

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l-Ascorbic acid has multifunctional benefits on skin aesthetics, including inhibition of melanin production, and is widely used in cosmetics. It, however, has low stability and poor skin penetration. We hypothesize that alkylglyceryl-l-ascorbic acid derivatives, highly stable vitamin C–alkylglycerol conjugates, would have similar anti-melanogenic activity with better stability and penetration. We test 28 alkylglyceryl-l-ascorbic acid derivatives (1–28) on theophylline-stimulated B16 melanoma 4A5 cells to determine if they inhibit melanogenesis and establish any structure–function relationships. Although not the most potent inhibitors, 3-O-(2,3-dihydroxypropyl)-2-O-hexyl-l-ascorbic acid (6, IC50 = 81.4 µM) and 2-O-(2,3-dihydroxypropyl)-3-O-hexyl-l-ascorbic acid (20, IC50 = 117 µM) are deemed the best candidate derivatives based on their inhibitory activities and low toxicities. These derivatives are also found to be more stable than l-ascorbic acid and to have favorable characteristics for skin penetration. The following structural requirements for inhibitory activity of alkylglyceryl-l-ascorbic acid derivatives are also determined: (i) alkylation of glyceryl-l-ascorbic acid is essential for inhibitory activity; (ii) the 3-O-alkyl-derivatives (2–14) exhibit stronger inhibitory activity than the corresponding 2-O-alkyl-derivatives (16–28); and (iii) derivatives with longer alkyl chains have stronger inhibitory activities. Mechanistically, our studies suggest that l-ascorbic acid derivatives exert their effects by suppressing the mRNA expression of tyrosinase and tyrosine-related protein-1.

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Section: Resultssupporting

confidence: 61%

Structural Requirements of Alkylglyceryl-l-Ascorbic Acid Derivatives for Melanogenesis Inhibitory Activity

Taira

Katsuyama²,

Yoshioka³

et al. 2018

IJMS

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“… 28 − 31 In practical applications, VC and its derivatives still have a variety of factual problems. 32 − 34 For example, the efficient dosage of VC in cancer treatment is very controversial, and related research shows that a low concentration of VC has a certain degree of pro-oxidation, while a high concentration will inhibit the free radical chain reaction. Therefore, a more in-depth exploration of VC and the improvement of its chemical structure to obtain more active and stable derivatives is also an increasingly important direction of study.…”

Section: Introductionmentioning

confidence: 99%

“…Density functional theory (DFT) calculations are often used to analyze the chemical properties of biomolecules (including antioxidant capacity, intermolecular force, and enzyme catalytic ability). Based on the development of DFT computational chemistry in recent years, the current theoretical research results are often used to predict the oxidation resistance of substances, and the calculations related to the oxidation resistance of VC have also gradually deepened. − In practical applications, VC and its derivatives still have a variety of factual problems. − For example, the efficient dosage of VC in cancer treatment is very controversial, and related research shows that a low concentration of VC has a certain degree of pro-oxidation, while a high concentration will inhibit the free radical chain reaction. Therefore, a more in-depth exploration of VC and the improvement of its chemical structure to obtain more active and stable derivatives is also an increasingly important direction of study.…”

Section: Introductionmentioning

confidence: 99%

Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory

Liu

2020

ACS Omega

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Vitamin C (VC) is an essential antioxidant, but its application is limited because of its unstable chemical properties. Hence, a variety of VC derivatives have emerged in practical antioxidant applications. To explore the relationship between the antioxidant properties and the chemical structures of vitamin C and its derivatives, density functional theory (DFT) was used in this work to calculate the reaction enthalpies of the mechanisms related to radical scavenging activity. The structures were optimized at the B3LYP-D3(BJ)/6-31G* level of theory. Single point calculations (SPE) were performed at the PWPB95-D3 (BJ)/def2-QZVPP level. To estimate the solvent effect on antioxidant properties, the SMD (solvation model based on density) method was used. The results showed that in the process of optimizing the chemical structure of vitamin C, the antioxidant capacity of its derivatives decreased slightly in aqueous solvents. In the calculation process, it is also found that in the choice of antioxidant mechanism, these compounds are more inclined to the hydrogen atom transfer (HAT) mechanism, and from the chemical structure point of view, the double bond of the lactone ring is essential for its free radical scavenging activity. In general, it is necessary to continue to optimize the structure of VC to obtain derivatives with better oxidation resistance and more practical value.

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“…At the same time, strong reductants can reduce the production of melanin by reducing or combining with the intermediates in the process of melanin production. Like vitamin C and VC-HG, which can inhibit the tyrosinase activity and comprehensively reduce the deposition of melanin on the skin surface through its own reduction, so as to achieve whitening effect (Taira et al, 2018).…”

Section: Inhibiting the Synthesis Of Melaninmentioning

confidence: 99%

Review on oral plant extracts in Skin Whitening

WANG¹,

An²,

Qu³

et al. 2022

Food Sci. Technol

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Skin whitening has become one of the aesthetic problems among humans around the world, especially on women which is highly attention to skin beauty and whitening. Many of the plant extracts in oral energy drinks have whitening effects and good taste, which can support the health of the skin. We use the National Center for Biotechnology Information (NCBI) as a search engine to find literatures about skin whitening, oral plant extracts. This review mainly introduces the mechanism of skin whitening and the application of oral plant extracts in skin whitening. Skin whitening at melanin synthesis, melanosome transport, metabolism, oxidative stress, UV stimulation, other environmental stimulation inseparable. Many oral plant extracts are natural tyrosine inhibitors. The review concludes the melanin synthesis and transporting, pathway of melanin synthesis, whitening mechanism and the function of whitening on Green tea polyphenols, Rose Petal Extract (Rosa gallica), Pears, Peony, Rosa roxburghii Tratt, Olive (Olea europaea L.), Pomegranates, Phyllanthus emblica L., Mulberry extract, Açaí berry, saussurea involucrate flavonoids extract, etc. These will provide a strong foundation for the application of oral plant extracts in skin whitening. Furthermore, the mixture with function of skin whitening/ skin anti-aging / anti-inflammatory antioxidant oral plant extract can be a good candidate for further development on skin care product.

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3‐O‐Glyceryl‐2‐O‐hexyl ascorbate suppresses melanogenesis by interfering with intracellular melanosome transport and suppressing tyrosinase protein synthesis

Abstract: We conclude that VC-HG has an impact on skin lightening/whitening by inhibiting tyrosinase protein synthesis and interfering with intracellular melanosome transport.

Cited by 10 publications

References 38 publications

Structural Requirements of Alkylglyceryl-l-Ascorbic Acid Derivatives for Melanogenesis Inhibitory Activity

Structural Requirements of Alkylglyceryl-l-Ascorbic Acid Derivatives for Melanogenesis Inhibitory Activity

Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory

Review on oral plant extracts in Skin Whitening

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