DEPIGMENTING AGENTS in .NET

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CHAPTER 33 DEPIGMENTING AGENTS
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Many companies are performing research on newer, less controversial skin lighteners If a ban on HQ is implemented, there is one product that would remain unaffected: Tri-Luma When the FDA solicited safety data on HQ several years ago, only the manufacturers of TriLuma complied and it has now been approved for the short-term and intermittent long-term treatment of moderate to severe melasma Tri-Luma contains 4% HQ, 005% tretinoin, and 001% fluocinolone acetonide
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HO O HO HO OH O OH
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TABLE 33-1 Flavonoids and Flavonoid-like Compoundsa 177 FAMILY Hydroxystilbene derivatives Resveratrol Oxyresveratrol Piceatannol (PICE) Gnetol (4-Methoxy-benzyliden)(3-methoxy-phenyl)amine 4,4-Dihydroxybiphenyl Rosmarinic acid, rooperol Hydroxy avanols conjugated to gallic acid EGCG [( )-epigalloc atechin- 3-O-gallate] GCG [( )-gallocatechin3-O-gallate] Proanthocyanidins Grape seed extract Pycnogenol Elaters Ellagic acid Flavonols Genistein 6,7,4Trihydroxyiso avone Apigenin Quercetin (in onions) Flavanones (Chalcones) Isoliquiritigeninchalcone Butein Aloesin
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FIGURE 33-3 The chemical structure of arbutin melanocytes treated with arbutin, an increase of pigmentation occurred15 These results have not yet been duplicated and there are currently no published clinical studies evaluating the effects of arbutin on pigmentation disorders Arbutin serves as an ingredient in various cosmetic products Deoxyarbutin, a synthetic derivative of arbutin, has shown promising in vitro and in vivo results with a greater inhibition of tyrosinase than the plant-derived compound16
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INHIBITION OF MELANIN FORMATION
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Aloesin
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COSMETIC DERMATOLOGY: PRINCIPLES AND PRACTICE 280
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Aloesin (Fig 33-2) is a C-glycosylated chromone naturally derived from aloe vera It competitively inhibits tyrosinase, by suppressing both the hydroxylation of tyrosine to DOPA and oxidation of DOPA to DOPAchinone, and it inhibits melanin production in cultured normal melanocytes11 Aloesin and a few chemically related chromones have been demonstrated to exhibit an even stronger inhibitory effect on tyrosinase than arbutin and kojic acid12 Another study on the inhibitory effect of aloesin and/or arbutin (administered 4 times a day for 15 days) on pigmentation in human skin after UV radiation showed suppressed pigmentation by 34% for aloesin, by 435% for arbutin, and by 633% for the cotreatment with aloesin and arbutin compared with the control group13
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Flavonoids
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More than 4000 flavonoids have been identified in leaves, barks, and flowers All have phenolic and pyrane rings, and are therefore considered benzopyrane derivatives17 Many flavonoids display depigmenting effects (Table 33-1) They are classified into six major groups: flavanols, flavones, flavonols, flavanones, isoflavones, and anthocyanidins These classes differ in the conjugation of rings and the position of hydroxyl, methoxy, and glycosidic groups18 Flavonoids exhibit antioxidant properties but they can also directly inhibit tyrosinase and act on the distal part of the melanogenesis oxidative pathway Resveratrol (Fig 33-4) falls into the hydroxystilbene derivative group of flavonoids as do oxyresveratrol and gnetol, which are more efficient tyrosinase inhibitors than resveratrol19 Resveratrol induces depigmentation also by reducing microphthalmia-associated transcription factor (MITF) and tyrosinase promoter activity a pathway that will be described in more detail below20 In a recent study aimed at developing a skin whitening agent, investigators assessed the inhibitory effects on tyrosinase of 285 different herbal extracts, and found that Ramulus mori extracts performed optimally This extract contains 2-oxyresveratrol and showed strong inhibition of tyrosinase activity, as well as melanin synthesis in B-16 melanoma cells, and caused no toxicity or irritation in various animal tests21 Ellagic acid is isolated from strawberries, green tea, eucalyptus, and geraniums It is a tyrosinase inhibitor and has been shown to prevent UV-induced pig-
Arbutin
Arbutin (C 12 H 16 O 7 ) is a naturallyoccurring -D-glucopyranoside that consists of a molecule of HQ bound to glucose (Fig 33-3) Traditionally used in Japan, arbutin is present in the leaves of pear trees and certain herbs, such as wheat and bearberry Its depigmenting mechanism involves a reversible inhibition of melanosomal tyrosinase activity rather than suppression of the expression and synthesis of tyrosinase14 However, the utility of arbutin as a depigmenting agent is unclear Nakajima et al recently reported that although tyrosinase activity was reduced in normal human
Flavonoids and avonoid-like substances show varying degrees of tyrosinase inhibition Some of these ingredients also inhibit melanin production through pathways other than tyrosinase inhibition , mild inhibition; , moderate inhibition; , strong inhibition; , not enough studies performed to rank
mentation Ellagic acid seems to be more effective than kojic acid or arbutin and it is safer than HQ as it affects melanogenesis without cytotoxic reaction22
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