Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides
Publication type: Journal Article
Publication date: 2018-07-01
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
PubMed ID:
29920401
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
Isotachioside (1) and its related natural product 2 are isolated from Isotachis japonica and Protea neriifolia, respectively, and are categorized as analogs of arbutin (3), a tyrosinase inhibitor for practical use. Both of the natural products and several derivatives such as glucoside 4, xyloside 5, cellobioside 6, and maltoside 7 were synthesized via Schmidt glycosylation as a key step, and their tyrosinase inhibitory activity was evaluated. The half maximal inhibitory concentration (IC50) of 1-3 could not be determined even when the concentration was increased to 1000 μM. Contrastingly, glycosides 4-7, missing methyl and benzoyl groups, acted as tyrosinase inhibitors with IC50s of 417 μM, 852 μM, 623 μM, and 657 μM, respectively. Among these novel inhibitors, derivative 4 was the most potent, indicating that the structural combination of resorcinol and glucose was significant for inducing the inhibitory effect.
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17
Total citations:
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Citations from 2024:
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(17.64%)
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GOST
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MATSUMOTO T. et al. Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides // Carbohydrate Research. 2018. Vol. 465. pp. 22-28.
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MATSUMOTO T., Nakajima T., Iwadate T., Nihei K. Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides // Carbohydrate Research. 2018. Vol. 465. pp. 22-28.
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TY - JOUR
DO - 10.1016/j.carres.2018.06.004
UR - https://doi.org/10.1016/j.carres.2018.06.004
TI - Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides
T2 - Carbohydrate Research
AU - MATSUMOTO, TAKASHI
AU - Nakajima, Takuya
AU - Iwadate, Takehiro
AU - Nihei, Ken
PY - 2018
DA - 2018/07/01
PB - Elsevier
SP - 22-28
VL - 465
PMID - 29920401
SN - 0008-6215
SN - 1873-426X
ER -
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BibTex (up to 50 authors)
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@article{2018_MATSUMOTO,
author = {TAKASHI MATSUMOTO and Takuya Nakajima and Takehiro Iwadate and Ken Nihei},
title = {Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides},
journal = {Carbohydrate Research},
year = {2018},
volume = {465},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016/j.carres.2018.06.004},
pages = {22--28},
doi = {10.1016/j.carres.2018.06.004}
}