Identification of 3′-hydroxygenistein as a potent melanogenesis inhibitor from biotransformation of genistein by recombinant Pichia pastoris

Ding, Hsiou-Yu; Chiang, Chien-Min; Tzeng, Wei-Ming; Chang, Te‐Sheng

doi:10.1016/j.procbio.2015.06.007

Cited by 20 publications

(17 citation statements)

References 23 publications

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“…At present, though a wide range of tyrosinase inhibitors from natural and synthetic sources have been reported, only a few of them, in addition to being effective, are known as safe compounds. No significant advances concerning toxicity issues of tyrosinase inhibitors seem to emerge from the literature survey carried out for this review, the relevant papers just reporting the results of in vitro cytotoxicity experiments [49,52,75,81,95,126,129,[131][132][133]136,137,147,163,[176][177][178]184,185,192,198,202,203,207,210,212,214,215,239,240,242,245] and only a few of in vivo experiments on zebrafish [130,206,209]. Therefore, it is essential to examine the efficacy and safety of inhibitors by checking e.g., whether or not the candidate inhibitor is substrate of tyrosinase being modified on exposure to the enzyme.…”

Section: Discussionmentioning

confidence: 99%

“…Low IC50 values against both monophenolase and diphenolase activty of mushroom tyrosinase have been very recently reported for p-coumaric and caffeic acid [66], belonging to the cinammic acid family ( Figure 7). The IC50 values together with structural formulas for other phenolic compounds widely distributed in nature that have been the subject of studies that appeared in the last five years [53,62,63,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82] Low IC 50 values against both monophenolase and diphenolase activty of mushroom tyrosinase have been very recently reported for p-coumaric and caffeic acid [66], belonging to the cinammic acid family ( Figure 7). Moving to simple phenols, significant inhibition activity has been described for 4-hydroxybenzyl alcohol (IC50 = 6 μM) [61] and isoeugenol (IC50 = 33.3 μM) [62], which would appear more efficient than resorcinol [55] or rhododendrol [63] themselves.…”

Section: Natural Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

“…Low IC50 values against both monophenolase and diphenolase activty of mushroom tyrosinase have been very recently reported for p-coumaric and caffeic acid [66], belonging to the cinammic acid family (Figure 7). The IC50 values together with structural formulas for other phenolic compounds widely distributed in nature that have been the subject of studies that appeared in the last five years [53,62,63,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82] The IC 50 values together with structural formulas for other phenolic compounds widely distributed in nature that have been the subject of studies that appeared in the last five years [53,62,63,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82] are also reported in Figures 4-8.…”

Section: Natural Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

“…In the last five years, several natural and synthetic phenolic compounds have been described also as inhibitors of tyrosinase from animal and human sources. Most of these studies used B16 murine melanoma cell lines as a model [52,55,75,85,95,96,99,114,122,123,[127][128][129][132][133][134][135]138,139,151,153,155,163,, although some papers using zebrafish as an in vivo whole animal model have also been published [55,116,206]. As to the human sources, data on inhibition of human recombinant or purified tyrosinase [9,207], human melanoma cells [130,136], normal human melanocytes [208][209][210][211], or human skin models consisting of reconstructed three-dimensional human epidermis [212][213][214][215] have been published (Figure 21).…”

Section: Human and Animal Tyrosinase Phenolic Inhibitorsmentioning

confidence: 99%

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Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed.

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Section: Discussionmentioning

confidence: 99%

Section: Natural Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

“…Low IC50 values against both monophenolase and diphenolase activty of mushroom tyrosinase have been very recently reported for p-coumaric and caffeic acid [66], belonging to the cinammic acid family (Figure 7). The IC50 values together with structural formulas for other phenolic compounds widely distributed in nature that have been the subject of studies that appeared in the last five years [53,62,63,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82] The IC 50 values together with structural formulas for other phenolic compounds widely distributed in nature that have been the subject of studies that appeared in the last five years [53,62,63,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82] are also reported in Figures 4-8.…”

Section: Natural Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

Section: Human and Animal Tyrosinase Phenolic Inhibitorsmentioning

confidence: 99%

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Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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“…Cancerous cell gene expression studies reveal that genistein inhibits angiogenesis and protein kinases and also blocks cell cycle progression at G2-M check point. It also increases the melanin production and tyrosinase activity in some specific cancer tissues and is capable of inhibiting the activation of NF-κB-mediated signaling cascade, which bring stability between cell death and survival [78]. This phenomenon made genistein a perfect anticancer compound in prostate cancer as it reverses epigenetic causes related to the cancer.…”

Section: Genisteinmentioning

confidence: 99%

Regulation of Oxidative Stress by Different Naturally Occurring Polyphenolic Compounds: An Emerging Anticancer Therapeutic Approach

Dutta

Sadhukhan

Saha

et al. 2017

ROS

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Oxidative stress is a critical factor for the development of cancer via inducing DNA mutations, damage, and genome instability. Different signaling pathways associated with the progression of cancer can modulate the intracellular level of reactive oxygen species (ROS). The level of intracellular ROS is usually high in cancer cells compared to different normal cell types due to abnormal functionality of different genes and perturbed metabolic activity facilitating extensive cellular proliferation. Among a few therapeutic options practiced recently, chemotherapy is the most effective so far. Despite its antitumor efficacy, treatment procedures of chemotherapy have several major side effects and this provokes the scientists for developing novel therapeutic option with minimum toxicity. Different naturally occurring polyphenolic compounds exhibit potential anti-oxidative, anti-inflammatory, and pro-apoptotic effect in several anticancer studies. The use of different polyphenolic compounds to target the redox status of the cell is a very promising strategy. These pleotropic polyphenolic compounds have been widely documented to modulate different signaling pathways in cancer cells either directly or indirectly. In this comprehensive review, we have summarized the anti-proliferative and pro-apoptotic properties of different polyphenolic compounds in various in vitro and in vivo cancer models.

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Functional expression of eukaryotic cytochrome P450s in yeast

Jiang

Huang

Cai

et al. 2020

Biotech & Bioengineering

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Cytochrome P450 enzymes (P450s) are a superfamily of heme‐thiolate proteins widely existing in various organisms. Due to their key roles in secondary metabolism, degradation of xenobiotics, and carcinogenesis, there is a great demand to heterologously express and obtain a sufficient amount of active eukaryotic P450s. However, most eukaryotic P450s are endoplasmic reticulum‐localized membrane proteins, which is the biggest challenge for functional expression to high levels. Furthermore, the functions of P450s require the cooperation of cytochrome P450 reductases for electron transfer. Great efforts have been devoted to the heterologous expression of eukaryotic P450s, and yeasts, particularly Saccharomyces cerevisiae are frequently considered as the first expression systems to be tested for this challenging purpose. This review discusses the strategies for improving the expression and activity of eukaryotic P450s in yeasts, followed by examples of P450s involved in biosynthetic pathway engineering.

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Identification of 3′-hydroxygenistein as a potent melanogenesis inhibitor from biotransformation of genistein by recombinant Pichia pastoris

Cited by 20 publications

References 23 publications

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Regulation of Oxidative Stress by Different Naturally Occurring Polyphenolic Compounds: An Emerging Anticancer Therapeutic Approach

Functional expression of eukaryotic cytochrome P450s in yeast

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