Phlorotannins Derived From the Brown Alga Colpomenia bullosa as Tyrosinase Inhibitors

2021 ◽  
Vol 16 (7) ◽  
pp. 1934578X2110213
Author(s):  
Hideyuki Kurihara ◽  
Kazuki Kujira
Keyword(s):  
Inhibitory Activity ◽  
Brown Alga ◽  
Molecular Structures ◽  
Free Form ◽  
Biosynthesis Pathway ◽  
Tyrosinase Inhibitor ◽  
Melanin Biosynthesis ◽  
Tyrosinase Inhibitory Activity ◽  
Tyrosinase Inhibitors ◽  
Potential Use

Tyrosinase catalyzes hydroxylation of L-tyrosine and dehydrogenation of L-DOPA in the melanin biosynthesis pathway. Tyrosinase inhibitors have potential use as cosmetic whitening agents and for preventing seafood deterioration. In this report, tyrosinase inhibitors extracted from brown alga Colpomenia bullosa (Scytosiphonaceae, Scytosiphonales) were investigated. Inhibitory principles were isolated from the extract and identified as phlorotannins, phloroglucinol (1), diphlorethol (2), triphlorethol C (3), which have not been isolated in a free form previously, and fucophlorethol C (4). Compounds 3 and 4 have not been reported previously as tyrosinase inhibitors. Triphlorethol C (3) was the most potent tyrosinase inhibitor among the phlorotannins isolated, whereas isomeric fucophlorethol C (4) displayed the weakest inhibitory activity. The results suggest that molecular structures of phlorotannins strongly affect their tyrosinase inhibitory activity.

scholarly journals Palladium(II)-Catalyzed Efficient Synthesis of Wedelolactone and Evaluation as Potential Tyrosinase Inhibitor

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4130
Author(s):  
Huidan Huang ◽  
Jianqiu Chen ◽  
Jie Ren ◽  
Chaofeng Zhang ◽  
Fei Ji
Keyword(s):  
Natural Product ◽  
Raw Material ◽  
Coupling Reactions ◽  
Biosynthesis Pathway ◽  
Tyrosinase Inhibitor ◽  
Efficient Synthesis ◽  
Melanin Biosynthesis ◽  
Methodological Research ◽  
Palladium Catalyzed ◽  
Tyrosinase Inhibitors

Tyrosinase is an enzyme widely distributed in nature, which has multiple functions, especially in the melanin biosynthesis pathway. Despite the few clinically available tyrosinase inhibitors for whitening, a great demand remains for novel compounds with low side effects in terms of potential carcinogenicity and improved clinical efficacy. A natural product, wedelolactone (WEL), with a polyhydroxyl moiety, attracted our attention as a potential tyrosinase inhibitor. Before we studied the biological activity of the natural product, a synthetic methodological research was firstly carried to obtain enough raw material. WEL could be obtained efficiently through palladium-catalyzed boronation/coupling reactions and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)-involved oxidative deprotection/annulation reactions. Immediately after, the natural product was proven to be an efficient tyrosinase inhibitor. In conclusion, we developed a mild and efficient approach for the preparation of WEL, and the natural product was disclosed to have anti-tyrosinase activity, which could be widely used in multiple fields.

scholarly journals Azastilbene Analogs as Tyrosinase Inhibitors: New Molecules with Depigmenting Potential

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Larissa Lavorato Lima ◽  
Rebeca Mól Lima ◽  
Annelisa Farah da Silva ◽  
Antônio Márcio Resende do Carmo ◽  
Adilson David da Silva ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Tyrosinase Inhibitor ◽  
Tyrosinase Inhibition ◽  
Tyrosinase Inhibitory Activity ◽  
Qualitative And Quantitative ◽  
Phenolic Ring ◽  
Tyrosinase Inhibitors ◽  
Resveratrol Analogs ◽  
Better Than

This research has been an effort to develop synthetic resveratrol analogs in order to improve the depigmenting potential of natural resveratrol. Six resveratrol analogs were synthesized and tested for tyrosinase inhibitory activityin vitro, by qualitative and quantitative steps. The results showed the analogCas being the most powerful tyrosinase inhibitor (IA50= 65.67 ± 0.60 μg/mL), followed by the analogsB,E,F,A, andD, respectively. The analogCpresented a tyrosinase inhibition potential better than natural resveratrol (P<0.001). The best depigmenting activity was provided by the presence of hydroxyl in the orthoposition on the second phenolic ring.

scholarly journals AKTIVITAS INHIBITOR TIROSINASE PADA EKSTRAK ALGA COKELAT SARGASSUM SP. AGARDH ASAL PESISIR LHOK BUBON, KABUPATEN ACEH BARAT

2018 ◽  
Vol 1 (1) ◽  
Author(s):  
Muhammad Gazali
Keyword(s):  
Inhibitory Activity ◽  
Brown Algae ◽  
Methanol Extract ◽  
Kojic Acid ◽  
Bioactive Compound ◽  
Positive Control ◽  
Marine Macroalgae ◽  
Tyrosinase Inhibitor ◽  
Tyrosinase Inhibitory Activity ◽  
New Finding

Seaweeds are marine macro algae that can be found attach to the bottom shallow coastal waters with subsrate as attached media. There are three major groups of seaweeds namely brown algae (Phaeophyta), red (Rhodophyta) and green (Chlorophyta). Sargassum sp is one of brown algae which mostly found in the Lhok Bubon Coastal West of Aceh. Recently, exploration of marine macroalgae as bioactive sources was investigated. Seaweed contains bioactive compound which can serve as a defense from ultraviolet radiation that caused hyperpigmentation effect. The aiming of this study is to analyse the tyrosinase inhibitory activity of Sargassum sp extract from Lhok Bubon Coastal Area, West of Aceh. The results shown that the methanol extract of Sargassum sp possess phytochemical properties such as fenol, alkaloid and triterpenoid. Tyrosinase inhibitory activity of Sargassum sp methanol extract  is the best extract which can be inhibit  monophenolase with  IC50 : 1111.49 µg/ml and IC50 = 1582.31 µg/ml in diphenolase pathway with kojic acid as positive control. Moreover, etyl asetate and n-hexane extract have no activity of tyrosinase inhibitor. Therefore, new finding of tyrosinase inhibitor agent from marine macroalgae Sargassum sp give the fruitfull information for cosmeceutical industry.Keywords : Lhok Bubon, Brown Algae, Sargassum sp, Tyrosinase Inhibitor

scholarly journals POTENSI MAKROALGA PADINA AUSTRALIS (HAUCK 1887) DI BARAT SELATAN ACEH SEBAGAI AGEN INHIBITOR TIROSINASE

2018 ◽  
Vol 5 (1) ◽  
pp. 71
Author(s):  
Mohamad Gazali ◽  
Eri Safutra ◽  
Zulfadhli Zulfadhli
Keyword(s):  
Inhibitory Activity ◽  
Brown Algae ◽  
Methanol Extract ◽  
Bioactive Compound ◽  
Positive Control ◽  
Raw Material ◽  
Marine Macroalgae ◽  
Tyrosinase Inhibitor ◽  
Tyrosinase Inhibitory Activity ◽  
New Finding

Seaweeds are marine macro algae that can be found attach to the bottom shallow coastal waters. There are three major groups of seaweeds namely brown algae (Phaeophyta), red (Rhodophyta) and green (Chlorophyta). Padina australis is one of brown algae which mostly found in the West-South of Aceh coastal Area.  Seaweed contains bioactive compound which can serve as a defense from ultraviolet radiation that caused hyperpigmentation effect The purpose of this study is to analyse the tyrosinase inhibitory activity of P. australis extract from West-South Aceh. The results shown that the methanol extract of P. australis possess phytochemical properties such as flavonoids, tannin and saponin. tyrosinase inhibitory activity of P. australis  methanol extract  is the best extract which can be inhibit monophenolase with  IC50 : 293.520 µg/ml and IC50 = 13.571.067 µg/ml in diphenolase pathway with kojic acid as positive control. Moreover, chloroform and n-hexane extract have no activity of tyrosinase inhibitor. Therefore, new finding of tyrosinase inhibitor agent from marine macroalgae P. australis give the fruitfull information for cosmeceutical industry. P. australis parts could be complementary each other in providing the raw material of cosmetic product.

scholarly journals Identification by shape-based virtual screening and evaluation of new tyrosinase inhibitors

PeerJ ◽  
2018 ◽  
Vol 6 ◽  
pp. e4206 ◽  
Author(s):  
Qi Li ◽  
Hongyu Yang ◽  
Jun Mo ◽  
Yao Chen ◽  
Yue Wu ◽  
...  
Keyword(s):  
Virtual Screening ◽  
Inhibitory Activity ◽  
Skin Pigmentation ◽  
Competitive Inhibitor ◽  
Tyrosinase Inhibitor ◽  
Starting Point ◽  
Good Starting Point ◽  
Tyrosinase Inhibitors ◽  
Dopa Formation ◽  
Potent Inhibitory Activity

Targeting tyrosinase is considered to be an effective way to control the production of melanin. Tyrosinase inhibitor is anticipated to provide new therapy to prevent skin pigmentation, melanoma and neurodegenerative diseases. Herein, we report our results in identifying new tyrosinase inhibitors. The shape-based virtual screening was performed to discover new tyrosinase inhibitors. Thirteen potential hits derived from virtual screening were tested by biological determinations. Compound 5186-0429 exhibited the most potent inhibitory activity. It dose-dependently inhibited the activity of tyrosinase, with the IC50 values 6.2 ± 2.0 µM and 10.3 ± 5.4 µM on tyrosine and L-Dopa formation, respectively. The kinetic study of 5186-0429 demonstrated that this compound acted as a competitive inhibitor. We believe the discoveries here could serve as a good starting point for further design of potent tyrosinase inhibitor.

Design and discovery of tyrosinase inhibitors based on a coumarin scaffold

RSC Advances ◽  
2015 ◽  
Vol 5 (114) ◽  
pp. 94227-94235 ◽  
Author(s):  
M. J. Matos ◽  
C. Varela ◽  
S. Vilar ◽  
G. Hripcsak ◽  
F. Borges ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Tyrosinase Inhibitory Activity ◽  
Tyrosinase Inhibitors

A novel series of 3-aryl and 3-heteroarylcoumarins displaying tyrosinase inhibitory activity.

scholarly journals Tyrosinase Inhibitory Activity, 3D QSAR, and Molecular Docking Study of 2,5-Disubstituted-1,3,4-Oxadiazoles

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Ramesh L. Sawant ◽  
Prashant D. Lanke ◽  
Jyoti B. Wadekar
Keyword(s):  
Enzyme Inhibition ◽  
Inhibitory Activity ◽  
3D Qsar ◽  
Docking Study ◽  
Docking Studies ◽  
Maximum Activity ◽  
Tyrosinase Inhibitor ◽  
Molecular Docking Study ◽  
Tyrosinase Inhibitory Activity ◽  
Vlife Mds

In continuation with our research program, in search of potent enzyme tyrosinase inhibitor, a series of synthesized 2,5-disubstituted 1,3,4-oxadiazoles have been evaluated for enzyme tyrosinase inhibitory activity. Subsequently, 3D QSAR and docking studies were performed to find optimum structural requirements for potent enzyme tyrosinase inhibitor from this series. The synthesized 20 compounds of 2,5-disubstituted-1,3,4-oxadiazole series were screened for mushroom tyrosinase inhibitory activity at various concentrations by enzyme inhibition assay. The percentage enzyme inhibition was calculated by recording absorbance at 492 nm with microplate reader. 3D QSAR and docking studies were performed using VLife MDS 3.5 software. In the series 2,5-disubstituted-1,3,4-oxadiazoles enzyme tyrosinase inhibitory activity was found to be dose dependent with maximum activity for compounds4c,4h,4m, and4r. 3D QSAR and docking studies revealed that more electropositive and less bulky substituents if placed on 1,3,4-oxadiazole nucleus may result in better tyrosinase inhibitory activity in the series.

The effect of chlorophorin and its derivative on melanin biosynthesis

Holzforschung ◽  
2005 ◽  
Vol 59 (5) ◽  
pp. 514-518 ◽  
Author(s):  
Enos Tangke Arung ◽  
Keisuke Yoshikawa ◽  
Kuniyoshi Shimizu ◽  
Ryuichiro Kondo
Keyword(s):  
Inhibitory Activity ◽  
Melanoma Cells ◽  
B16 Melanoma ◽  
Mushroom Tyrosinase ◽  
Tyrosinase Inhibitor ◽  
Melanin Biosynthesis ◽  
B16 Melanoma Cells ◽  
Bioassay Guided Fractionation ◽  
Unstable Compound ◽  
Potent Inhibitory Activity

Abstract By means of bioassay-guided fractionation using mushroom tyrosinase, a geranylated stilbene, chlorophorin, was characterized as the principal tyrosinase inhibitor in the heartwood of Chlorophora excelsa (Moraceae). It inhibited the oxidation of L-tyrosine and DL-3,4-dihydroxyphenylalanine (DL-DOPA) due to mushroom tyrosinase and melanin biosynthesis on B16 melanoma cells. Chlorophorin, which is a slight yellowish compound, has previously been reported as an unstable compound in light. On the basis of this finding, a chlorophorin derivative [4-(3″,7″-dimethyloctyl)-2′,3,4′,5-tetrahydroxydihydrostilbene; hexahydrochlorophorin] which is colorless, obtained by the hydrogenation of chlorophorin with Pd/C, was also tested to develop a superior material for practical use. Hexahydrochlorophorin showed more potent inhibitory activity on tyrosinase and melanin biosynthesis, and lower cytotoxicity towards B16 melanoma cells than chlorophorin.

scholarly journals Diarylalkanoids as Potent Tyrosinase Inhibitors from the Stems of Semecarpus caudata

2021 ◽  
Vol 2021 ◽  
pp. 1-8
Author(s):  
Phu H. Dang ◽  
Tho H. Le ◽  
Truong N. V. Do ◽  
Hai X. Nguyen ◽  
Mai T. T. Nguyen ◽  
...  
Keyword(s):  
Amino Acid ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Data Interpretation ◽  
Docking Studies ◽  
Amino Acid Residues ◽  
Soluble Extract ◽  
Tyrosinase Inhibitory Activity ◽  
Ic50 Values ◽  
Tyrosinase Inhibitors

From a CHCl3-soluble extract of the stems of Semecarpus caudata (Anacardiaceae), two new diarylalkanoids, semedienone (1) and semetrienone (2), were isolated. Their structures were elucidated based on NMR spectroscopic data interpretation. These compounds possess strong tyrosinase inhibitory activity with the IC50 values of 0.033 and 0.11 μM, respectively. Docking studies of 1 and 2 with oxy-tyrosinase were carried out to analyze their interactions. Accordingly, semedienone (1) showed good interactions with the peroxide group and amino acid residues. The biosynthesis of the isolated diarylalkanoids was proposed.

scholarly journals Mushroom tyrosinase inhibitory activity and major fatty acid constituents of Amazonian native flora oils

2012 ◽  
Vol 48 (3) ◽  
pp. 399-404 ◽  
Author(s):  
Raquel da Silva Teixeira ◽  
Paula Rafaela Rocha ◽  
Hudson Caetano Polonini ◽  
Marcos Antônio Fernandes Brandão ◽  
Maria das Graças Afonso Miranda Chaves ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Inhibitory Activity ◽  
Major Fatty Acid ◽  
Mushroom Tyrosinase ◽  
Melanin Biosynthesis ◽  
Tyrosinase Inhibitory Activity ◽  
Native Flora ◽  
Global Trend ◽  
Main Components

In order to treat hyperpigmentation-related problems, there has been a global trend in developing cosmetics claiming to have skin-whitening properties, which act by inhibiting melanin biosynthesis. The objective of this work was to evaluate the in vitro mushroom tyrosinase inhibitory activity of five Amazonian native flora oils, and so to verify the possibility of their incorporation into cosmetic products. In addition, the fatty acid composition of the essential oils was determined by gas chromatography-flame ionisation detection in order to determine the main components of these oils. The tyrosinase inhibitory activity of the tested oils was found to be in the following order: açaí (IA50 = 66.08 µg mL-1) > tucumã > patauá > pracaxi > castanha do Brasil. This study suggests that açaí oil has great potential in the treatment of hyperpigmentation and other related disorders, due to its considerable tyrosinase inhibitory activity.

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