Inhibitory Effects of Magnesium Ascorbyl Phosphate on Melanogenesis.

Tagawa, Manabu; Murata, Tomoji; Onuma, Toshio; Kameyama, Keiichi; Sakai, Chie; Kondô, Shigeo; Yonemoto, Kohzoh; Quigley, John M.; Dorsky, Albert; Bucks, Daniel A. W.; Blanock, Kurt

doi:10.5107/sccj.27.409

Cited by 2 publications

(3 citation statements)

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“…A more stable APM was developed by phosphorylation of the hydroxyl group at position 2 of ascorbic acid to form magnesium salt; this compound was approved for use in Japanese quasi-drugs in the 1980s. APM has been used for the treatment of hyperpigmentation (melasma and Riehl melanosis) since 1969 [ 2 ], and its effectiveness in the treatment of sunburn-induced hyperpigmentation has been demonstrated in well-controlled studies since 1983 [ 3 , 4 ]. To make APM more stable under weakly acidic conditions, glucose has been attached to the hydroxyl group at position 2 to form 2-O-α-D-glucopyranosyl-L-ascorbic acid (ascorbyl glucoside; AA-2G), a compound that is stable around pH 6 that was approved as an active ingredient in quasi-drugs in the 1990s [ 5 , 6 ].…”

Section: Development Of Skin-lightening Active Ingredientsmentioning

confidence: 99%

“…Other topically applied products with good results for melasma include 1% or 2.5% kojic acid [ 23 ], 3% arbutin [ 31 ], 1% tranexamic acid [ 66 ], 0.1% linoleic acid S [ 52 ], 0.3% Rucinol [ 37 ], and 0.5% ellagic acid [ 36 ]. Examples of topically applied products with good results for senile pigmentation include 3% APM [ 2 ], 10% APM [ 3 , 4 ], 1% or 2.5% kojic acid [ 23 , 24 , 25 ], 0.5% ellagic acid [ 36 ], 7% arbutin [ 87 ], and 0.5% chamomile extract [ 51 ]. Topical application of 1% or 2.5% kojic acid [ 23 ], 0.5% ellagic acid [ 36 ], 1% tranexamic acid [ 66 ], and 7% arbutin [ 87 ] has been used with good results in the treatment of freckles.…”

Section: Effectiveness Indices Of Lightening Ingredients Developed In...mentioning

confidence: 99%

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Timeline of the Development of Skin-Lightening Active Ingredients in Japan

Maeda

2022

Molecules

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Japanese pharmaceutical cosmetics, often referred to as quasi-drugs, contain skin-lightening active ingredients formulated to prevent sun-induced pigment spots and freckles. Their mechanisms of action include suppressing melanin production in melanocytes and promoting epidermal growth to eliminate melanin more rapidly. For example, arbutin and rucinol are representative skin-lightening active ingredients that inhibit melanin production, and disodium adenosine monophosphate and dexpanthenol are skin-lightening active ingredients that inhibit melanin accumulation in the epidermis. In contrast, oral administration of vitamin C and tranexamic acid in pharmaceutical products can lighten freckles and melasma, and these products are more effective than quasi-drugs. On the basis of their clinical effectiveness, skin-lightening active ingredients can be divided into four categories according to their effectiveness and adverse effects. This review discusses academic research and development regarding skin-lightening ingredients in Japan.

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Section: Development Of Skin-lightening Active Ingredientsmentioning

confidence: 99%

Section: Effectiveness Indices Of Lightening Ingredients Developed In...mentioning

confidence: 99%

Timeline of the Development of Skin-Lightening Active Ingredients in Japan

Maeda

2022

Molecules

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“…AsA has multifunctional benefits on parameters affecting skin aesthetics, such as the reduction in oxidative stress and increase in collagen production. Among them, the prevention and improvement in skin pigmentation by AsA and its derivatives are, collectively, one of the most important benefits for people [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. However, it is well known that AsA is unstable in formulations, and has a low ability to penetrate the skin due to its hydrophilicity.…”

Section: Introductionmentioning

confidence: 99%

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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Inhibitory Effects of Magnesium Ascorbyl Phosphate on Melanogenesis.

Cited by 2 publications

References 3 publications

Timeline of the Development of Skin-Lightening Active Ingredients in Japan

Timeline of the Development of Skin-Lightening Active Ingredients in Japan

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

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