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FIGURE 33-2 The chemical structure of aloesin
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FIGURE 33-4 The chemical structure of resveratrol
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GENTISIC ACID Gentisic acid (Fig 33-5) is derived from genetian roots It has been tested in vitro and in cell cultures proving its inhibitory effect on tyrosinase However, methyl gentisate seems to be more effective than the free acid In vitro studies have shown HQ to be less effective and more cytotoxic to melanocytes than methyl gentisate23
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FIGURE 33-6 The chemical structure of kojic acid kojic acid combined with glycolic acid was shown to be more effective when compared with 10% glycolic acid and 4% HQ for the treatment of hyperpigmentation31,32 A study by Lim compared the effect of a gel containing 10% glycolic acid and 2% HQ with and without 2% kojic acid33 The result was that the addition of kojic acid to the gel further improved melasma Products that contain kojic acid are usually used twice daily for 1 to 2 months or until the patient achieves the desired effect Unfortunately, kojic acid has been associated with contact allergy and is considered to have a high sensitizing potential34 Because preparations using 25% concentrations of kojic acid have resulted in facial dermatitis,35 a concentration of 1% is usually used However, there have been reports of sensitization to 1% creams as well34 Since it has been extensively used in foods, there have been many reports on its oral safety Toxicity resulting from an oral dose has been reported in a recent Japanese study recording the occurrence of hepatocellular tumors in p53-deficient mice36 Furthermore, convulsions may occur if kojic acid is injected30 Lee et al recently reported on derivatives of kojic acid displaying increased efficiency through increased penetration into the skin37
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FIGURE 33-7 The chemical structure of glabridin Topical applications of 05% glabridin have also been demonstrated to inhibit UVB-induced pigmentation and erythema in the skin of guinea pigs Furthermore, it has been shown that the inhibition of superoxide anion production and cyclooxygenase activity demonstrated the anti-inflammatory effects of glabridin in vitro42 Notably, Gl glabra has shown efficacy in the treatment of melasma43 One study suggested that glabridin exhibits a superior depigmenting effect compared to HQ44 In Europe, licorice extract is widely used as an antiin ammatory agent45 However, there are no controlled clinical trials in the literature examining the efficacy of this agent to treat inflammation Forms of licorice extract have been incorporated into skin care products to prevent inflammation One such ingredient is licochalcone A an oxygenated retrochalcone that is found in Eucerin Redness Relief products Licochalone has exhibited antiparasitic, antibacterial, and antitumorigenic activity as well as shown efficacy in treating rosacea17,46 50
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Coumarins are lactones of phenylpropanoid acid with an H-benzopyranone nucleus They directly interact with tyrosinase A Japanese group studied the antimelanogenic activity of six hydrocoumarins and alpha-tocopherol in normal human melanocytes In particular, 7-allyl-6-hydroxy-4,4,5,8tetramethylhydrocoumarin (hydrocoumarin 4) strongly inhibited melanogenesis and intracellular glutathione (GSH) synthesis in normal human melanocytes The investigators suggested that hydrocoumarin 4 may be effective in preventing hyperpigmentation and proposed a combined treatment of hydrocoumarins and alphatocopherols to enhance the hypopigmenting effect by a free radical-scavenging mechanism24
CHAPTER 33 DEPIGMENTING AGENTS
Kojic Acid
Kojic acid (5-hydroxy-2-hydroxymethyl-pyrone or C6H6O4) (Fig 33-6) is a fungal metabolite commonly produced by various species of Aspergillus, Acetobacter, and Penicillium25 It is widely used as a food additive for preventing enzymatic browning and to promote reddening of unripe strawberries26 Kojic acid suppresses tyrosinase activity, mainly by chelating copper This leads to a whitening effect on the skin27 Consequently, manufacturers, particularly in Japan, have used it extensively in cosmetic agents28 When used in cosmetic products, kojic acid enhances the product s shelf life through its preservative and antibiotic actions29 This stability is one of the advantages of kojic acid when compared to HQ and other depigmenting agents30 In two separate studies,
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