Pubfacts - Scientific Publication Data
  • Categories
  • |
  • Journals
  • |
  • Authors
  • Login
  • Categories
  • Journals

Search Our Scientific Publications & Authors

Publications
  • Publications
  • Authors
find publications by category +
Translate page:

Effect of Active Groups and Oxidative Dimerization on the Antimelanogenic Activity of Catechins and Their Dimeric Oxidation Products.

Authors:
Wei Wang Lin Chen Weiwei Wang Jianyong Zhang Ulrich H Engelhardt Heyuan Jiang

J Agric Food Chem 2022 Feb 20;70(4):1304-1315. Epub 2022 Jan 20.

Key Laboratory of Tea Biology and Resources Utilization, Ministry of Agriculture, Tea Research Institute, Chinese Academy of Agricultural Sciences, 9 Meiling South Road, Xihu District, Hangzhou, Zhejiang 310008, People's Republic of China.

Some catechins and their dimeric oxidation products are well known to possess antimelanogenic activity, which could be influenced by their structures and oxidative dimerization. This study compared the antimelanogenic activity of different catechins and dimeric oxidation products and clarified the mechanism using an α-MSH-stimulated B16F10 cell model. It was found that 100 μg/mL (-)-gallocatechin gallate, (-)-epigallocatechin gallate, theasinensin A, and theaflavine-3,3'-digallate could significantly inhibit melanin synthesis without cytotoxicity. The tyrosinase (TYR) activities were 26.24 ± 4.97, 31.57 ± 5.37, 66.10 ± 9.62, and 78.19 ± 5.14%, respectively, and the melanin contents were 38.29 ± 3.50, 41.21 ± 7.62, 62.13 ± 9.80, and 68.82 ± 11.62%, respectively. These compounds inhibit melanin production by attenuating the mRNA levels of TYR, TRP1, and TRP2 gene. The structure-activity relationship showed that geometrical isomerism was not the key factor affecting catechins' antimelanogenic activity. Compared with the catechol, catechins with B-ring pyrogallol inhibited melanin synthesis more effectively. The number of galloyl groups was positively correlated with antimelanogenic activity. Compared with 3-galloyl, 3'-galloyl was a stronger active group in antimelanogenesis. Interestingly, the contribution of B-ring pyrogallol to the antimelanogenic activity was significantly stronger than that of 3-galloyl in catechins. Additionally, the antimelanogenic activity of the dimeric oxidation product at 100 μM was more than or equal to that of individual substrate-catechin, while being significantly less than that of the substrate-catechin mixture. Results indicated that pyrogallol and galloyl were the active groups inhibiting melanin synthesis. The oxidative dimerization weakened the antimelanogenic activity of the substrate-catechin mixture.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.jafc.1c07028DOI Listing
February 2022

Publication Analysis

Top Keywords

antimelanogenic activity
32
dimeric oxidation
16
melanin synthesis
12
oxidation products
12
oxidative dimerization
12
catechins dimeric
12
activity compared
8
activity catechins
8
substrate-catechin mixture
8
active groups
8
activity
8
inhibit melanin
8
antimelanogenic
8
b-ring pyrogallol
8
melanin
5
catechins
5
geometrical isomerism
4
relationship geometrical
4
isomerism key
4
key factor
4

Keyword Occurance

Similar Publications

Cyano-Phycocyanin: Mechanisms of Action on Human Skin and Future Perspectives in Medicine.

Authors:
Daiva Dranseikienė Gabrielė Balčiūnaitė-Murzienė Jūratė Karosienė Dmitrij Morudov Nomeda Juodžiukynienė Nataliia Hudz Rima Jūratė Gerbutavičienė Nijolė Savickienė

Plants (Basel) 2022 May 5;11(9). Epub 2022 May 5.

Department of Pharmacognosy, Faculty of Pharmacy, Academy of Medicine, Lithuanian University of Health Sciences, Sukileliu av. 13, 50162 Kaunas, Lithuania.

Cyano-phycocyanin is one of the active pigments of the blue-green algae and is usually isolated from the filamentous cyanobacteria Gomont (Spirulina). Due to its multiple physiological functions and non-toxicity, cyano-phycocyanin may be a potential substance for the topical treatment of various skin diseases. Considering that the conventional medicine faces drug resistance, insufficient efficacy and side effects, the plant origin compounds can act as an alternative option. Read More

View Article and Full-Text PDF
May 2022
Similar Publications

Metabolic Basis and Clinical Evidence for Skin Lightening Effects of Thiol Compounds.

Authors:
Yong Chool Boo

Antioxidants (Basel) 2022 Mar 4;11(3). Epub 2022 Mar 4.

Department of Molecular Medicine, School of Medicine, Kyungpook National University, 680 Gukchaebosang-ro, Jung-gu, Daegu 41944, Korea.

Melanin pigment is a major factor in determining the color of the skin, and its abnormal increase or decrease can cause serious pigmentation disorders. The melanin pigment of the skin is divided into light pheomelanin and dark eumelanin, and a big difference between them is whether they contain sulfur. Melanin synthesis starts from a common reaction in which tyrosine or dihydroxyphenylalanine (DOPA) is oxidized by tyrosinase (TYR) to produce dopaquinone (DQ). Read More

View Article and Full-Text PDF
March 2022
Similar Publications

Inhibitory effects and underlying mechanisms of essential oil on melanogenesis in the B16F10 cell line.

Authors:
Min Jae Kim Elsayed A Mohamed Da Som Kim Mi-Jin Park Byoung-Jun Ahn Eui-Bae Jeung Beum-Soo An

Mol Med Rep 2022 Apr 9;25(4). Epub 2022 Feb 9.

Department of Biomaterials Science (BK21 FOUR Program), College of Natural Resources and Life Science/Life and Industry Convergence Research Institute, Pusan National University, Miryang, Gyeongsangnam‑do 50463, Republic of Korea.

The present study investigated the anti‑melanogenic activity of 10 essential oils using the B16F10 cell model. Initially, a wide range of concentrations of these essential oils were screened in order to determine their toxicity levels. The assigned non‑toxic concentrations of the tested essential oils were then used to evaluate their effects on melanogenesis. Read More

View Article and Full-Text PDF
April 2022
Similar Publications

Molecular Docking, Synthesis, and Tyrosinase Inhibition Activity of Acetophenone Amide: Potential Inhibitor of Melanogenesis.

Authors:
Yasir Nazir Hummera Rafique Sadia Roshan Shazia Shamas Zaman Ashraf Muhammad Rafiq Tehreem Tahir Zia-Ur-Rahman Qureshi Alvina Aslam Muhammad Hassham Hassan Bin Asad

Biomed Res Int 2022 11;2022:1040693. Epub 2022 Jan 11.

Department of Pharmacy, COMSATS University Islamabad, Abbottabad Campus, 22060, Pakistan.

Tyrosinase and its related proteins are responsible for pigmentation disorders, and inhibiting tyrosinase is an established strategy to treat hyperpigmentation. The carbonyl scaffolds can be effective inhibitors of tyrosinase activity, and the fact that both benzoic and cinnamic acids are safe natural substances with such a scaffolded structure, it was speculated that hydroxyl-substituted benzoic and cinnamic acid derivatives may exhibit potent tyrosinase inhibitory activity. These moieties were incorporated into new chemotypes that displayed in vitro inhibitory effect against mushroom tyrosinase with a view to explore antimelanogenic ingredients. Read More

View Article and Full-Text PDF
January 2022
Similar Publications

Effect of Active Groups and Oxidative Dimerization on the Antimelanogenic Activity of Catechins and Their Dimeric Oxidation Products.

Authors:
Wei Wang Lin Chen Weiwei Wang Jianyong Zhang Ulrich H Engelhardt Heyuan Jiang

J Agric Food Chem 2022 Feb 20;70(4):1304-1315. Epub 2022 Jan 20.

Key Laboratory of Tea Biology and Resources Utilization, Ministry of Agriculture, Tea Research Institute, Chinese Academy of Agricultural Sciences, 9 Meiling South Road, Xihu District, Hangzhou, Zhejiang 310008, People's Republic of China.

Some catechins and their dimeric oxidation products are well known to possess antimelanogenic activity, which could be influenced by their structures and oxidative dimerization. This study compared the antimelanogenic activity of different catechins and dimeric oxidation products and clarified the mechanism using an α-MSH-stimulated B16F10 cell model. It was found that 100 μg/mL (-)-gallocatechin gallate, (-)-epigallocatechin gallate, theasinensin A, and theaflavine-3,3'-digallate could significantly inhibit melanin synthesis without cytotoxicity. Read More

View Article and Full-Text PDF
February 2022
Similar Publications
}
© 2022 PubFacts.
  • About PubFacts
  • Privacy Policy
  • Sitemap