Daedalin A, a Metabolite of<i>Daedalea dickinsii</i>, Inhibits Melanin Synthesis in an<i>in Vitro</i>Human Skin Model

Morimura, Keiji; Hiramatsu, Kenji; Yamazaki, C.; Hattori, Yasunao; Makabe, Hidefumi; Hirota, Mitsuru

doi:10.1271/bbb.80695

Cited by 8 publications

(4 citation statements)

References 19 publications

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“…27). 236 Deadalin A has been shown to have anti-tyrosinase activity (IC 50 of 194 mM) and thus to inhibit melanin synthesis in a three-dimensional human skin model. Tanaka et al isolated a 3-hydroxy-chromane (203) from Acremonium murorum, 237 a hyaline phialide.…”

Section: Fungimentioning

confidence: 99%

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Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Birringer

Siems²,

Maxones

et al. 2018

RSC Adv.

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Section: Fungimentioning

confidence: 99%

“…27 ). 236 Deadalin A has been shown to have anti-tyrosinase activity (IC 50 of 194 μM) and thus to inhibit melanin synthesis in a three-dimensional human skin model.…”

Section: Hemiterpenesmentioning

confidence: 99%

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Birringer

Siems²,

Maxones

et al. 2018

RSC Adv.

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“…Enzyme kinetics were determined using various l ‐tyrosine concentrations . l ‐tyrosine samples with concentrations ranging from 0.2 to 2.4 mmol/L were mixed with 105 μL CM extracts, paeonol, or arbutin at 25°C for 10 minutes.…”

Section: Methodsmentioning

confidence: 99%

Safety and efficacy of tyrosinase inhibition of Paeonia suffruticosa Andrews extracts on human melanoma cells

Lin

Wang

Song

et al. 2019

J of Cosmetic Dermatology

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Introduction The development of tyrosinase inhibitors is a hot research topic. Recently, the Chinese herb Paeonia suffruticosa Andrews, commonly named as Cortex Moutan (CM), was reported as being capable of reducing melanogenesis. We developed an A2058 human melanoma cell model to test the safety and efficacy of tyrosinase inhibition. The aim was to further clarify the bioactivities of CM extracts and paeonol for the purpose of skin whitening. Methods The 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) scavenging activity, total polyphenol and flavonoid contents, and in vitro tyrosinase inhibitory effects of water and ethanol CM extracts were determined. Cellular inhibitions of tyrosinase and melanin production were also evaluated. Results Water and ethanol CM extracts were both shown to have strong DPPH scavenging abilities in a dose‐dependent manner. The polyphenol content was higher in the ethanol CM extract compared to the water extract, while the flavanone content was comparable. Kinetic analyses revealed that the ethanol CM extract and paeonol are noncompetitive tyrosinase inhibitors. The cellular melanin content and l‐DOPA oxidation assays demonstrated that the ethanol CM extract was an appropriate alternative whitening agent to paeonol and arbutin in ultraviolet‐induced A2058 human melanoma cells. Conclusion The results of this study suggest that a human cell model is more suitable for determining tyrosinase activity than mouse cell models for determining cellular tyrosinase activity and melanin production. The ethanol CM extract was also confirmed as a promising ingredient in sun protection and skin whitening cosmetics. Future work should focus on melanogenesis‐related gene expressions.

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“…This result suggested that the mechanism of action of quercinol (2), which has an opposite stereochemistry at C-2 position, might be different from that of daedalin (1) in the tyrosinase inhibitory activity (Table 1). 3 …”

Section: (78%) (G) Lialh 4 Diethyl Ether (88%) (H) Dmp P-tsoh (mentioning

confidence: 99%

Asymmetric syntheses of daedalin A and quercinol and their tyrosinase inhibitory activity

Sekimoto¹,

Hattori²,

Morimura³

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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Stereoselective syntheses of daedalin A and quercinol, an enantiomer of daedalin A, is described. The tyrosinase inhibitory activities of daedalin A and quercinol were examined. The activity of quercinol was weaker than that of daedalin A at high concentration.Dermal hyper-pigmentation, caused by the accumulation of melanin, is initiated by oxidation of tyrosine by tyrosinase, a key enzyme of melanin biosynthesis.1 Tyrosinase inhibitors such as arbutin, kojic acid, ellagic acid, and rucinol have been used as pharmaceutical constituents of cosmetics in order to prevent hyper-pigmentation. In an effort to find new types of tyrosinase inhibitors, we have screened culture broths from mushroom mycelia for tyrosinase inhibitory activity, and found that the mycelial culture of Daedalia dickinsii showed significant activity.Based on the spectroscopic data, the bioactive compound was elucidated as (2R)-6-hydroxymethyl-2-methyl-2H-chromene, named daedalin A (1). 2,3 We have synthesized racemic 1 and it showed weaker activity than 1.3 Quercinol (2), an enantiomer of daedalin A (1), was also isolated from the fungus of Daedalea quercina by Hertweck and co-workers. 4 They reported that compound 2 showed anti-inflammatory activity. 4 It is very difficult to obtain enough amount of daedalin A (1) and quercinol (2) for the biological study because the mycelia cultures of Daedalia dickinsii and/or Daedalea quercina are limited. Thus, syntheses of 1, 2, and their analogues are important for the biological study. Especially, synthesis of 2 is required because the tyrosinase inhibitory activity of 2 has not been reported yet. Herein, we wish to describe an asymmetric synthesis of 1 and 2 and their tyrosinase inhibitory activity (Figure 1).

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Daedalin A, a Metabolite ofDaedalea dickinsii, Inhibits Melanin Synthesis in anin VitroHuman Skin Model

Cited by 8 publications

References 19 publications

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Safety and efficacy of tyrosinase inhibition of Paeonia suffruticosa Andrews extracts on human melanoma cells

Asymmetric syntheses of daedalin A and quercinol and their tyrosinase inhibitory activity

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