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Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions

BACKGROUND: A bisresorcinol was isolated as the main constituent of Heliciopsis terminalis’s trunk (Proteaceae). Recently, resorcinol is applied as an active whitening agent in various cosmetic products. Because of the structural mimic to resorcinol, benefits of the bisresorcinol as an aging-enzyme...

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Autores principales: Saechan, Charinrat, Nguyen, Uyen Hoang, Wang, Zhichao, Sugimoto, Sachiko, Yamano, Yoshi, Matsunami, Katsuyoshi, Otsuka, Hideaki, Phan, Giang Minh, Pham, Viet Hung, Tipmanee, Varomyalin, Kaewsrichan, Jasadee
Formato: Online Artículo Texto
Lenguaje:English
Publicado: PeerJ Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8231342/
https://www.ncbi.nlm.nih.gov/pubmed/34221723
http://dx.doi.org/10.7717/peerj.11618
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author Saechan, Charinrat
Nguyen, Uyen Hoang
Wang, Zhichao
Sugimoto, Sachiko
Yamano, Yoshi
Matsunami, Katsuyoshi
Otsuka, Hideaki
Phan, Giang Minh
Pham, Viet Hung
Tipmanee, Varomyalin
Kaewsrichan, Jasadee
author_facet Saechan, Charinrat
Nguyen, Uyen Hoang
Wang, Zhichao
Sugimoto, Sachiko
Yamano, Yoshi
Matsunami, Katsuyoshi
Otsuka, Hideaki
Phan, Giang Minh
Pham, Viet Hung
Tipmanee, Varomyalin
Kaewsrichan, Jasadee
author_sort Saechan, Charinrat
collection PubMed
description BACKGROUND: A bisresorcinol was isolated as the main constituent of Heliciopsis terminalis’s trunk (Proteaceae). Recently, resorcinol is applied as an active whitening agent in various cosmetic products. Because of the structural mimic to resorcinol, benefits of the bisresorcinol as an aging-enzyme antagonist were demonstrated in this study. METHODS: The bisresorcinol was purified from the crude ethanolic extract of H. terminalis’s trunk by solvent extraction and preparative chromatography, respectively. Inhibitory activity on collagenase, elastase, and tyrosinase of the compound was investigated by using a different spectroscopic technique. Molecular docking was carried out to predict possible interactions of the substance around the enzyme active sites. RESULTS: The IC(50) values on collagenase of the bisresorcinol and caffeic acid were 156.7 ± 0.7 and 308.9 ± 1.6 µmole L(−1), respectively. For elastase activity, the IC(50) of 33.2 ± 0.5 and 34.3 ± 0.3 µmole L(−1) was respectively determined for the bisresorcinol and ursolic acid. The bisresorcinol was inhibitory to tyrosinase by exhibiting the IC(50) of 22.8 µmole L(−1), and that of 78.4 µmole L(−1) was present for β-arbutin. The bisresorcinol bound to collagenase, elastase, and tyrosinase with the respective binding energies of −5.89, −5.69, and −6.57 kcal mol(−1). These binding energies were in the same ranges of tested inhibitors. The aromatic phenol groups in the structure were responsible for principle as well as supporting binding interactions with enzymes. Hydrogen binding due to hydroxyl groups and π-related attractive forces from an aromatic ring(s) provided binding versatility to bisresorcinol. CONCLUSION: The bisresorcinol purified from H. terminalis might be useful for inclusion in cosmetic products as an aging-enzyme antagonist.
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spelling pubmed-82313422021-07-01 Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions Saechan, Charinrat Nguyen, Uyen Hoang Wang, Zhichao Sugimoto, Sachiko Yamano, Yoshi Matsunami, Katsuyoshi Otsuka, Hideaki Phan, Giang Minh Pham, Viet Hung Tipmanee, Varomyalin Kaewsrichan, Jasadee PeerJ Biochemistry BACKGROUND: A bisresorcinol was isolated as the main constituent of Heliciopsis terminalis’s trunk (Proteaceae). Recently, resorcinol is applied as an active whitening agent in various cosmetic products. Because of the structural mimic to resorcinol, benefits of the bisresorcinol as an aging-enzyme antagonist were demonstrated in this study. METHODS: The bisresorcinol was purified from the crude ethanolic extract of H. terminalis’s trunk by solvent extraction and preparative chromatography, respectively. Inhibitory activity on collagenase, elastase, and tyrosinase of the compound was investigated by using a different spectroscopic technique. Molecular docking was carried out to predict possible interactions of the substance around the enzyme active sites. RESULTS: The IC(50) values on collagenase of the bisresorcinol and caffeic acid were 156.7 ± 0.7 and 308.9 ± 1.6 µmole L(−1), respectively. For elastase activity, the IC(50) of 33.2 ± 0.5 and 34.3 ± 0.3 µmole L(−1) was respectively determined for the bisresorcinol and ursolic acid. The bisresorcinol was inhibitory to tyrosinase by exhibiting the IC(50) of 22.8 µmole L(−1), and that of 78.4 µmole L(−1) was present for β-arbutin. The bisresorcinol bound to collagenase, elastase, and tyrosinase with the respective binding energies of −5.89, −5.69, and −6.57 kcal mol(−1). These binding energies were in the same ranges of tested inhibitors. The aromatic phenol groups in the structure were responsible for principle as well as supporting binding interactions with enzymes. Hydrogen binding due to hydroxyl groups and π-related attractive forces from an aromatic ring(s) provided binding versatility to bisresorcinol. CONCLUSION: The bisresorcinol purified from H. terminalis might be useful for inclusion in cosmetic products as an aging-enzyme antagonist. PeerJ Inc. 2021-06-22 /pmc/articles/PMC8231342/ /pubmed/34221723 http://dx.doi.org/10.7717/peerj.11618 Text en © 2021 Saechan et al. https://creativecommons.org/licenses/by/4.0/This is an open access article distributed under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, reproduction and adaptation in any medium and for any purpose provided that it is properly attributed. For attribution, the original author(s), title, publication source (PeerJ) and either DOI or URL of the article must be cited.
spellingShingle Biochemistry
Saechan, Charinrat
Nguyen, Uyen Hoang
Wang, Zhichao
Sugimoto, Sachiko
Yamano, Yoshi
Matsunami, Katsuyoshi
Otsuka, Hideaki
Phan, Giang Minh
Pham, Viet Hung
Tipmanee, Varomyalin
Kaewsrichan, Jasadee
Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
title Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
title_full Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
title_fullStr Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
title_full_unstemmed Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
title_short Potency of bisresorcinol from Heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
title_sort potency of bisresorcinol from heliciopsis terminalis on skin aging: in vitro bioactivities and molecular interactions
topic Biochemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8231342/
https://www.ncbi.nlm.nih.gov/pubmed/34221723
http://dx.doi.org/10.7717/peerj.11618
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