Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides

Matsumoto, Takashi; Nakajima, Takehiko; Iwadate, Takehiro; Nihei, Keiji

doi:10.1016/j.carres.2018.06.004

Cited by 19 publications

(8 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The same has been reported for the alkyl spacer in the case of resorcinol alkyl glucosides [166]. The presence of resorcinol and glucose moieties has also reported to be important [162]. Hydrogen bonds and aromatic (hydrophobic) interactions with tyrosinase have been predicted by docking simulation for the potent inhibitor MHY2081 [129].…”

Section: Structural Requirements For the Design Of Tyrosinase Inhibitorssupporting

confidence: 60%

“…Coumarin dimers and derivatives containing a tetracyclic skeleton exhibited IC50 values in the range 1.7-2.9 μM [172] (Figure 20), whereas even higher activity has been reported for synthetic 3-heteroarylcoumarins [173] and umbelliferone-thiazolidinedione hybrids [174] (Figure 20). Of course, the most potent inhibitory activity is still attributed to resorcinol derivatives [162][163][164][165][166][167][168][169][170], although these compounds often suffer from toxicity concerns (the case of rhododendrol is emblematic [6][7][8]) (see below). Low IC 50 values (0.39-3.62 µM) have been reported for resorcinol alkyl glucosides [166] (Figure 19), whereas thiamidol, which is currently one of the most potent skin depigmenting agent on the market, is not so active against mushroom tyrosinase (IC 50 = 108 µM) [9].…”

Section: Synthetic Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

See 1 more Smart Citation

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

2019

View full text Add to dashboard Cite

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.

show abstract

Section: Structural Requirements For the Design Of Tyrosinase Inhibitorssupporting

confidence: 60%

Section: Synthetic Phenolic Inhibitors Of Mushroom Tyrosinasementioning

confidence: 99%

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

2019

View full text Add to dashboard Cite

show abstract

“…But, glucoside, xyloside, cellobioside and maltoside derivatives, missing methyl and benzoyl groups, acted as tyrosinase inhibitors with IC 50 s of 417, 852, 623 and 657 µM, respectively. Among these novel inhibitors, glucoside derivative (IC 50 = 417 µM) was the most potent, indicating that the structural combination of resorcinol and glucose was significant for inducing the inhibitory effect 193 .…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

740

471

View full text Add to dashboard Cite

Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

show abstract

“…Melanin is one of the natural pigments responsible for skin pigmentation and hair color in mammals [23]. The excessive production of melanin results in hyperpigmentation dysfunctions, along with aging [24].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Guo

Zhang

et al. 2019

Molecules

View full text Add to dashboard Cite

Bee pollen contains all the essential amino acids needed by humans. China is the largest producer of bee pollen in the world. In the present study, we identified 11 fatty acids in F. esculentum bee pollen oil by GC-MS analysis, and 16 compounds were isolated from F. esculentum bee pollen by column chromatography and identified. A high-performance liquid chromatography-diode array detector (HPLC-DAD) method was established for the quality control of F. esculentum bee pollen. A validated HPLC-DAD method was successfully applied to the simultaneous characterization and quantification of nine main constituents in seven samples collected from seven different areas in China. The results showed that all standard calibration curves exhibited good linearity (R2 > 0.999) in HPLC-DAD analysis with excellent precision, repeatability and stability. The total amount in the samples from the seven regions ranged from 23.50 to 46.05 mg/g. In addition, seven compounds were studied for their bioactivity using enzymic methods, whereby kaempferol (3) showed high α-glucosidase inhibitory activity (IC50: 80.35 μg/mL), ergosterol peroxide (8) showed high tyrosinase inhibitory activity (IC50: 202.37 μg/mL), and luteolin (1) had strong acetylcholinesterase inhibitory activity (IC50: 476.25 μg/mL). All results indicated that F. esculentum bee pollen could be a nutritious health food.

show abstract

Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides

Cited by 19 publications

References 33 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

A comprehensive review on tyrosinase inhibitors

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Contact Info

Product

Resources

About