Antimelanogenic Activity of 3,4-Dihydroxyacetophenone: Inhibition of Tyrosinase and MITF

Kim, You Jung; No, Jae Kyung; Lee, Jun Sik; Kim, Myoung Soo; Chung, Hae Young

doi:10.1271/bbb.70.532

Cited by 37 publications

(24 citation statements)

References 10 publications

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“…This type of hypopigmenting agents does so by their cyto- toxic action on melanocytes rather than by tyrosinase inhibition. This is the case of 4-(p-hydroxyphenyl)-2-butanone (Fukuda et al, 1998) and 4-n-butylresorcinol (Kim et al, 2005a(Kim et al, , 2006c. The effect is in fact double as they inhibit tyrosinase but also act as cytotoxic agent as they are oxidized to their quinonic forms.…”

Section: Tyrosinase Inhibitorsmentioning

confidence: 99%

Hypopigmenting agents: an updated review on biological, chemical and clinical aspects

Solano¹,

Briganti²,

Picardo³

et al. 2006

Pigment Cell Research

611

521

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SummaryAn overview of agents causing hypopigmentation in human skin is presented. The review is organized to put forward groups of biological and chemical agents. Their mechanisms of action cover (i) tyrosinase inhibition, maturation and enhancement of its degradation; (ii) Mitf inhibition; (iii) downregulation of MC1R activity; (iv) interference with melanosome maturation and transfer; (v) melanocyte loss, desquamation and chemical peeling. Tyrosinase inhibition is the most common approach to achieve skin hypopigmentation as this enzyme catalyses the rate-limiting step of pigmentation. Despite the large number of tyrosinase inhibitors in vitro, only a few are able to induce effects in clinical trials. The gap between in-vitro and in-vivo studies suggests that innovative strategies are needed for validating their efficacy and safety. Successful treatments need the combination of two or more agents acting on different mechanisms to achieve a synergistic effect. In addition to tyrosinase inhibition, other parameters related to cytotoxicity, solubility, cutaneous absorption, penetration and stability of the agents should be considered. The screening test system is also very important as keratinocytes play an active role in modulating melanogenesis within melanocytes. Mammalian skin or at least keratinocytes/melanocytes co-cultures should be preferred rather than pure melanocyte cultures or soluble tyrosinase.

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Section: Tyrosinase Inhibitorsmentioning

confidence: 99%

Hypopigmenting agents: an updated review on biological, chemical and clinical aspects

Solano¹,

Briganti²,

Picardo³

et al. 2006

Pigment Cell Research

611

521

View full text Add to dashboard Cite

show abstract

“…6) We have reported on the significance of maintaining cellular redox through the down-regulation of RS and the boosting of antioxidant defenses in the inhibition of melanogenesis. 5,7,8) Various phenolic compounds from natural sources have been reported as melanogenic inhibitors. 5,[7][8][9][10][11] Hyperin and quercetin are two phenolic flavonoids reported to have antioxidative 12) and anti-viral 13) properties.…”

mentioning

confidence: 99%

“…5,7,8) Various phenolic compounds from natural sources have been reported as melanogenic inhibitors. 5,[7][8][9][10][11] Hyperin and quercetin are two phenolic flavonoids reported to have antioxidative 12) and anti-viral 13) properties. However, the effects of hyperin and quercetin on oxidative stress-induced melanogenesis have not been fully explored to date.…”

mentioning

confidence: 99%

Hyperin and Quercetin Modulate Oxidative Stress-Induced Melanogenesis

Kim

2012

Biological & Pharmaceutical Bulletin

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Hyperin and quercetin are phenolic compounds present in fruits and vegetables that have been reported to possess strong anti-oxidative properties. Although increasing evidence strongly suggests that antioxidants suppress the melanin synthesis that is causally associated with oxidative stress, the protective actions of hyperin and quercetin against oxidative stress-induced melanogenesis have not been fully explored. To elucidate the suppressive effects of hyperin and quercetin on oxidative stress and melanin synthesis, peroxynitrite (ONOO ) scavenging activity was measured in vitro as were quantifications of melanin content, intracellular total RS, ONOO , superoxide (• O 2 ), nitric oxide (NO • ), catalase activity and the reduced glutathione (GSH)/ oxidized glutathione (GSSG) ratio. Results showed that in vitro, hyperin and quercetin reduced ONOO . Additionally, hyperin and quercetin suppressed total RS, ONOO ,• O 2 , and NO• , catalase activity, and melanin synthesis, while they boosted the GSH/GSSG ratio in B16F10 melanoma cells (B16 cells). Therefore, I propose that hyperin and quercetin have a powerful capacity to modulate oxidative stress-induced melanogenesis.Key words hyperin; quercetin; antioxidant; oxidative stress; melanogenesis Melanogenesis is the process by which pigment forms and melanin is synthesized in special organelles called melanosomes.1) Melanin plays a key role in the protection of the skin against deleterious sunlight under normal conditions, but also can increase the generation and excessive accumulation of melanin that lead to clinical and cosmetic concerns such as freckles, age spots, sites of actinic damage, and melasma. Chronic inflammation, UV ray radiation, and the release of abnormal α-melanocyte stimulating hormone (α-MSH) also are well-known triggering factors for abnormal melanogenesis and inflammatory pigmentation. 1,2)Oxidative stress caused by excessive reactive species (RS), including reactive oxygen species (ROS) and reactive nitrogen species (RNS), is known to be associated with skin aging and hyperpigmentation. Also, a deficient anti-oxidative defense system, such as a disturbed redox balance and weak anti-oxidant enzyme activity, exacerbate skin aging and hyperpigmentaion.3-5) Therefore, searching for natural antioxidants that inhibit melanogenesis has been an important strategy in the development of skin medications and cosmetics. 6) We have reported on the significance of maintaining cellular redox through the down-regulation of RS and the boosting of antioxidant defenses in the inhibition of melanogenesis. 5,7,8) Various phenolic compounds from natural sources have been reported as melanogenic inhibitors. 5,7-11) Hyperin and quercetin are two phenolic flavonoids reported to have antioxidative 12) and anti-viral 13) properties. However, the effects of hyperin and quercetin on oxidative stress-induced melanogenesis have not been fully explored to date.To estimate the effects of hyperin and quercetin on oxidative insult in vitro, peroxynitrite (ONOO − ) scavenging act...

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“…Furthermore, our data correlate well with previous reports that induction of melanogenesis in B16 melanoma cells is characterized by stimulation of MITF and tyrosinase activity and gene expression. 31,32) Our study effected the separation and identified the biological activity of quercitrin from L. obtusiloba Blume leaves. To our knowledge, this is the first report on the presence of quercitrin in L. obtusiloba leaves and of the inhibitory effect of melanogenesis.…”

Section: Resultsmentioning

confidence: 96%

Separation of the Antioxidant Compound Quercitrin fromLindera obtusilobaBlume and Its Antimelanogenic Effect on B16F10 Melanoma Cells

Hong

Lee

Rhee

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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Antimelanogenic Activity of 3,4-Dihydroxyacetophenone: Inhibition of Tyrosinase and MITF

Cited by 37 publications

References 10 publications

Hypopigmenting agents: an updated review on biological, chemical and clinical aspects

Hypopigmenting agents: an updated review on biological, chemical and clinical aspects

Hyperin and Quercetin Modulate Oxidative Stress-Induced Melanogenesis

Separation of the Antioxidant Compound Quercitrin fromLindera obtusilobaBlume and Its Antimelanogenic Effect on B16F10 Melanoma Cells

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