4.6 Review

Tyrosinase Inhibitors Naturally Present in Plants and Synthetic Modifications of These Natural Products as Anti-Melanogenic Agents: A Review

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Review Biochemistry & Molecular Biology

Structure and inhibition mechanism of some synthetic compounds and phenolic derivatives as tyrosinase inhibitors: review and new insight

Morteza Vaezi

Summary: Safe and potent tyrosinase inhibitors are crucial for enhancing nutritional quality, promoting health, and preventing further damages. This review focuses on recent and efficient inhibitors discovered from synthetic sources and synthesized phenolic compounds. The inhibitory activity, mechanism, and potential applications of these inhibitors in various industries were discussed, emphasizing the importance of structural modification in finding novel and effective tyrosinase inhibitors.

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS (2023)

Review Chemistry, Applied

Plant flavonoids: Classification, distribution, biosynthesis, and antioxidant activity

Nan Shen et al.

Summary: Flavonoids are natural polyphenol substances abundant in various plant-based foods. They have significant biological activities in both plants and humans, such as antioxidant, antimicrobial, and anti-inflammatory effects. However, research on their distribution, biosynthesis, and health benefits remains limited. Future opportunities in flavonoid research include biotechnology, therapeutic phytoproducts, and exploring dietary flavonoid bioavailability.

FOOD CHEMISTRY (2022)

Article Biochemistry & Molecular Biology

Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach

Katarzyna Jakimiuk et al.

Summary: Flavonoids act as tyrosinase inhibitors, with quercetin being a competitive inhibitor that interferes with tyrosinase activity significantly. The study highlights the importance of hydroxylation and methylation at specific positions in the flavonoid molecules for their activity.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2022)

Article Agriculture, Multidisciplinary

Antioxidant and anti-tyrosinase activity of a novel stilbene analogue as an anti-browning agent

Wei Xia et al.

Summary: The novel stilbene analogue (SA) designed in this study showed potent inhibitory effect against mushroom tyrosinase, improved anti-tyrosinase effect compared to kojic acid, and possessed stronger antioxidant activities and non-toxicity.

JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE (2022)

Article Chemistry, Medicinal

Tyrosinase Inhibition by Novel Benzimidazole-thione Schiff Base Derivatives

Wei Zhou et al.

Summary: This study synthesized and investigated benzimidazolethione Schiff base derivatives as tyrosinase inhibitors. The compound S-4 showed the best inhibitory activity and low cytotoxicity, making it a promising candidate for treating hypermelanosis.

LETTERS IN DRUG DESIGN & DISCOVERY (2022)

Article Pharmacology & Pharmacy

Potency of moringa (Moringa oleifera L.) leaves extract containing quercetin as a depigmentation agent inhibiting the tyrosinase enzyme using in-silico and in-vitro assay

Ni Putu Linda Laksmiani et al.

Summary: This study investigated the affinity and molecular mechanism of quercetin, a potential skin-lightening agent, on the tyrosinase enzyme. Docking experiments revealed a strong affinity between quercetin and the enzyme. Furthermore, the study found that quercetin could be extracted from Moringa oleifera L. leaves using different methods, with the highest concentration obtained through maceration. In-vitro tests showed that the maceration extract had the potential to be a skin-lightening agent.

PHARMACIA (2022)

Article Pharmacology & Pharmacy

Topical nanocrystals of bioflavonoids: A new technology platform for skin ailments

Nivedita Pant et al.

Summary: Bioflavonoids are naturally derived compounds with various pharmacological actions. However, their low solubility and poor skin penetration limit their therapeutic applications for skin ailments. Nanocrystals of bioflavonoids have been developed to overcome these limitations. This review focuses on the preparation methods, in vitro evaluation, and animal studies of topical nanocrystals of bioflavonoids for different skin ailments.

INTERNATIONAL JOURNAL OF PHARMACEUTICS (2022)

Article Biochemistry & Molecular Biology

Biological and Cheminformatics Studies of Newly Designed Triazole Based Derivatives as Potent Inhibitors against Mushroom Tyrosinase

Mubashir Hassan et al.

Summary: A series of novel 1,2,4-triazole compounds were synthesized and their structures were characterized through spectral methods. The synthesized derivatives showed good inhibitory activity against mushroom tyrosinase, with N-(4-fluorophenyl)-2-(5-(2-fluorophenyl)-4-(4-fluorophenyl)-4H-1,2,4-triazol-3-ylthio) acetamide exhibiting the most prominent activity. Molecular docking studies revealed the interaction profile of these compounds at the active site of tyrosinase.

MOLECULES (2022)

Review Oncology

Melanoma, Melanin, and Melanogenesis: The Yin and Yang Relationship

Radomir M. Slominski et al.

Summary: Melanin plays a vital role in protecting the skin from harmful UV radiation, but its presence may also contribute to the malignant transformation of melanocytes. The biosynthesis of melanin is regulated by sun exposure and hormonal factors, influencing melanoma development, progression, and treatment in diverse ways.

FRONTIERS IN ONCOLOGY (2022)

Article Chemistry, Applied

Design and synthesis of novel stilbene-hydroxypyridinone hybrids as tyrosinase inhibitors and their application in the anti-browning of freshly-cut apples

Yu-Zhu Zhu et al.

Summary: A series of compounds were synthesized, among which compound 1h showed potent tyrosinase inhibitory activity. Various experiments indicated that the inhibitory mechanism of 1h is likely to be related to copper coordination and reduction.

FOOD CHEMISTRY (2022)

Article Biotechnology & Applied Microbiology

Cephalosporin as Potent Urease and Tyrosinase Inhibitor: Exploration through Enzyme Inhibition, Kinetic Mechanism, and Molecular Docking Studies

Yahya S. Alqahtani et al.

Summary: In this study, 11 cephalosporin drugs were evaluated for their activity against urease and tyrosinase enzymes. The drugs showed significant activity, with ceftriaxone sodium and cefotaxime sodium being the most active. These drugs bind irreversibly to the enzymes and have the potential to be used as potent candidates for the treatment of enzyme-related diseases.

BIOMED RESEARCH INTERNATIONAL (2022)

Article Biochemistry & Molecular Biology

Acetophenone-Based 3,4-Dihydropyrimidine-2(1H)-Thione as Potential Inhibitor of Tyrosinase and Ribonucleotide Reductase: Facile Synthesis, Crystal Structure, In-Vitro and In-Silico Investigations

Aamer Saeed et al.

Summary: The study synthesized a 3,4-dihydropyrimidine-2(1H)-thione compound and confirmed its structure through various analyses. The compound showed strong inhibitory activity against tyrosinase and excellent binding affinity to DNA.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2022)

Article Biochemistry & Molecular Biology

Synthesis, computational studies and enzyme inhibitory kinetics of benzothiazole-linked thioureas as mushroom tyrosinase inhibitors

Rabail Ujan et al.

Summary: A series of benzothiazole-thiourea hybrids were synthesized, with one compound showing promising inhibition of tyrosinase, potentially useful for developing new inhibitors of melanogenesis.

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS (2021)

Article Biochemistry & Molecular Biology

Novel 1,3,4-oxadiazole compounds inhibit the tyrosinase and melanin level: Synthesis, in-vitro, and in-silico studies

Balasaheb D. Vanjare et al.

Summary: The study involved the synthesis and evaluation of 1,3,4-Oxadiazoles for their tyrosinase inhibitory potential. The most potent compound showed significant inhibition activity compared to the standard drug kojic acid, and exhibited favorable cytotoxicity results against B16F10 melanoma cells. Western blot analysis confirmed the compound's ability to decrease tyrosinase expression levels, while molecular docking studies revealed its interactions within the enzyme's active site. Additionally, a molecular dynamic simulation experiment was presented to assess protein structure stability.

BIOORGANIC & MEDICINAL CHEMISTRY (2021)

Article Biochemistry & Molecular Biology

Inhibitory Effect of Avenanthramides (Avn) on Tyrosinase Activity and Melanogenesis in α-MSH-Activated SK-MEL-2 Cells: In Vitro and In Silico Analysis

Jun-Young Park et al.

Summary: Melanin-related pigmentation disorders can be prevented by anti-melanogenic agents like Avenanthramide (Avn)-A-B-C, which demonstrated dose-dependent tyrosinase inhibitory activity, with Avn-A-B-C showing the strongest competitive inhibition against intracellular tyrosinase and melanin synthesis. AvnC was found to have a higher binding affinity for tyrosinase than AvnA and AvnB, and was predicted to interact with tyrosinase through two hydrogen bonds at specific amino acid residues. Additionally, AvnB and AvnC were predicted to be non-sensitizers in mammals.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

Review Chemistry, Multidisciplinary

Natural and synthetic flavonoid derivatives as new potential tyrosinase inhibitors: a systematic review

Rami J. Obaid et al.

Summary: Tyrosinase is a crucial oxidase in both plants and animals, playing a key role in melanin production and potentially causing skin issues if melanin is overproduced. Various skin-whitening products are available to reduce melanin formation, while synthetic tyrosinase inhibitors are needed for their protective effects against skin pigmentation.

RSC ADVANCES (2021)

Article Biochemistry & Molecular Biology

Potent Tyrosinase Inhibitory Activity of Curcuminoid Analogues and Inhibition Kinetics Studies

Anan Athipornchai et al.

Summary: The study compared the tyrosinase inhibitory activity of various curcuminoid analogues, finding several to be more active than the traditional kojic acid. Among them, the isoxazole analogue 12 exhibited the strongest inhibitory activity, being 20.9 times more effective than kojic acid on the L-tyrosine substrate.

COSMETICS (2021)

Review Plant Sciences

Melanin Pigment in Plants: Current Knowledge and Future Perspectives

Anastasiia Y. Glagoleva et al.

FRONTIERS IN PLANT SCIENCE (2020)

Article Chemistry, Medicinal

Advances in the Design of Genuine Human Tyrosinase Inhibitors for Targeting Melanogenesis and Related Pigmentations

Brayan Roulier et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

Article Chemistry, Medicinal

Resorcinol alkyl glucosides as potent tyrosinase inhibitors

Wakana Ishioka et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2019)

Review Biochemistry & Molecular Biology

A comprehensive review on tyrosinase inhibitors

Samaneh Zolghadri et al.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2019)

Article Mathematical & Computational Biology

Exploration of Novel Human Tyrosinase Inhibitors by Molecular Modeling, Docking and Simulation Studies

Mubashir Hassan et al.

INTERDISCIPLINARY SCIENCES-COMPUTATIONAL LIFE SCIENCES (2018)

Review Biochemistry & Molecular Biology

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

Takashi Matsumoto et al.

CARBOHYDRATE RESEARCH (2018)

Review Dermatology

Melatonin: A Cutaneous Perspective on its Production, Metabolism, and Functions

Andrzej T. Slominski et al.

JOURNAL OF INVESTIGATIVE DERMATOLOGY (2018)

Review Chemistry, Applied

Intrinsic and extrinsic regulation of human skin melanogenesis and pigmentation

C. Serre et al.

INTERNATIONAL JOURNAL OF COSMETIC SCIENCE (2018)

Letter Dermatology

The impact of skin hyperpigmentation and hyperchromia on quality of life: A cross-sectional study

Mayra B. C. Maymone et al.

JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY (2017)

Article Chemistry, Medicinal

Development of highly potent melanogenesis inhibitor by in vitro, in vivo and computational studies

Qamar Abbas et al.

DRUG DESIGN DEVELOPMENT AND THERAPY (2017)

Article Biochemistry & Molecular Biology

Acetazolamide Inhibits the Level of Tyrosinase and Melanin: An Enzyme Kinetic, In Vitro, In Vivo, and In Silico Studies

Qamar Abbas et al.

CHEMISTRY & BIODIVERSITY (2017)

Article Chemistry, Medicinal

Design, Synthesis and Biological Evaluation of Oxindole-Based Chalcones as Small-Molecule Inhibitors of Melanogenic Tyrosinase

Sharad Kumar Suthar et al.

CHEMICAL & PHARMACEUTICAL BULLETIN (2017)

Article Biochemistry & Molecular Biology

Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3(4-hydroxymethyl-phenyl)-propenone

Byung-Hak Kim et al.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2016)

Article Biochemistry & Molecular Biology

2-(4-Fluorophenyl)-quinazolin-4(3H)-one as a novel tyrosinase inhibitor: Synthesis, inhibitory activity, and mechanism

Rui Wang et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2016)

Review Biochemistry & Molecular Biology

Melanogenesis Inhibitors: Strategies for Searching for and Evaluation of Active Compounds

Agnieszka Gunia-Krzyzak et al.

CURRENT MEDICINAL CHEMISTRY (2016)

Article Spectroscopy

Inhibitory mechanisms of glabridin on tyrosinase

Jianmin Chen et al.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2016)

Article Multidisciplinary Sciences

The unravelling of the complex pattern of tyrosinase inhibition

Batel Deri et al.

SCIENTIFIC REPORTS (2016)

Article Chemistry, Applied

Anthocyanin contents in the seed coat of black soya bean and their anti-human tyrosinase activity and antioxidative activity

J. -K. Jhan et al.

INTERNATIONAL JOURNAL OF COSMETIC SCIENCE (2016)

Article Biochemistry & Molecular Biology

Kinetic Characterization of Oxyresveratrol as a Tyrosinase Substrate

Carmen Vanessa Ortiz-Ruiz et al.

IUBMB LIFE (2015)

Article Biochemistry & Molecular Biology

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

Zaman Ashraf et al.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2015)

Article Biotechnology & Applied Microbiology

Evaluation of the repeated-dose liver, bone marrow and peripheral blood micronucleus and comet assays using kojic acid

Yosuke Ogiwara et al.

MUTATION RESEARCH-GENETIC TOXICOLOGY AND ENVIRONMENTAL MUTAGENESIS (2015)

Review Dermatology

Melasma: a clinical and epidemiological review

Ana Carolina Handel et al.

ANAIS BRASILEIROS DE DERMATOLOGIA (2014)

Review Chemistry, Medicinal

Flavonoid Derivatives As Potent Tyrosinase Inhibitors - A Survey of Recent Findings Between 2008-2013

Ilkay Erdogan Orhan et al.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2014)

Article Medicine, Research & Experimental

Melanocytes and Their Diseases

Yuji Yamaguchi et al.

COLD SPRING HARBOR PERSPECTIVES IN MEDICINE (2014)

Article Agriculture, Multidisciplinary

Design and Synthesis of Hydroxypyridinone-L-phenylalanine Conjugates as Potential Tyrosinase Inhibitors

Dong-Fang Li et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2013)

Article Biochemistry & Molecular Biology

Synthesis and Biological Evaluation of Unsymmetrical Curcumin Analogues as Tyrosinase Inhibitors

Yongfu Jiang et al.

MOLECULES (2013)

Article Critical Care Medicine

Medicinal importance, pharmacological activities, and analytical aspects of aloin: A concise report

Kanika Patell et al.

JOURNAL OF ACUTE DISEASE (2013)

Article Biochemistry & Molecular Biology

Novel Tyrosinase Inhibitors From Natural Resources - Their Computational Studies

M.T.H. Khan

CURRENT MEDICINAL CHEMISTRY (2012)

Article Biochemistry & Molecular Biology

Effect of hesperetin on tyrosinase: Inhibition kinetics integrated computational simulation study

Yue-Xiu Si et al.

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES (2012)

Review Oncology

L-tyrosine and L-dihydroxyphenylalanine as hormone-like regulators of melanocyte functions

Andrzej Slominski et al.

PIGMENT CELL & MELANOMA RESEARCH (2012)

Review Dermatology

Melatonin and human skin aging

Konrad Kleszczynski et al.

DERMATO-ENDOCRINOLOGY (2012)

Article Biochemistry & Molecular Biology

Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors

Kai Bao et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2010)

Review Oncology

Natural Phenolic Compounds From Medicinal Herbs and Dietary Plants: Potential Use for Cancer Prevention

Wu-Yang Huang et al.

NUTRITION AND CANCER-AN INTERNATIONAL JOURNAL (2010)

Article Dermatology

Hormone influence on melanogenesis and spots formation

T. Tadokoro et al.

INTERNATIONAL JOURNAL OF COSMETIC SCIENCE (2010)

Article Agriculture, Multidisciplinary

Identification of an Alkylhydroquinone from Rhus succedanea as an Inhibitor of Tyrosinase and Melanogenesis

Yun-Ru Chen et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2009)

Article Biochemistry & Molecular Biology

Dual effects of aliphatic carboxylic acids on cresolase and catecholase reactions of mushroom tyrosinase

N. Gheibi et al.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2009)

Article Biochemistry & Molecular Biology

Tyrosinase Inhibitor Activity of Coumarin-Resveratrol Hybrids

Antonella Fais et al.

MOLECULES (2009)

Article Dermatology

Mechanism of tyrosinase inhibition by deoxyArbutin and its second-generation derivatives

S. Chawla et al.

BRITISH JOURNAL OF DERMATOLOGY (2008)

Review Chemistry, Medicinal

Flavonoids: Prospective Drug Candidates

Luisa Helena Cazarolli et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2008)

Review Cell Biology

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

Francisco Solano et al.

PIGMENT CELL RESEARCH (2006)

Review Dermatology

The treatment of melasma: A review of clinical trials

Aditya K. Gupta et al.

JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY (2006)

Article Dermatology

Addison's disease

Lynnette K. Nieman et al.

CLINICS IN DERMATOLOGY (2006)

Review Biochemistry & Molecular Biology

Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future

YJ Kim et al.

CELLULAR AND MOLECULAR LIFE SCIENCES (2005)

Article Biochemistry & Molecular Biology

Genotoxicity of the benzene metabolites para-benzoquinone and hydroquinone

M Gaskell et al.

CHEMICO-BIOLOGICAL INTERACTIONS (2005)

Article Biochemistry & Molecular Biology

Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica

T Masuda et al.

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY (2005)

Article Biochemistry & Molecular Biology

Successful resonance Raman study of cresolase activity of mushroom tyrosinase

SS Borojerdi et al.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2004)

Review Physiology

Melanin pigmentation in mammalian skin and its hormonal regulation

A Slominski et al.

PHYSIOLOGICAL REVIEWS (2004)

Article Biochemistry & Molecular Biology

Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers

O Nerya et al.

PHYTOCHEMISTRY (2004)

Article Agriculture, Multidisciplinary

Inhibitory effects of (S)- and (R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acids on tyrosinase activity

LL Yu

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2003)

Article Agriculture, Multidisciplinary

Kinetics of mushroom tyrosinase inhibition by quercetin

QX Chen et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2002)