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Six Natural Phenylethanoid Glycosides: Total Synthesis, Antioxidant and Tyrosinase Inhibitory Activities
Author(s) -
Shu Penghua,
Zhang Lingxiang,
Liu Anqi,
Li Junping,
Liu Qing,
Sun Na,
Zhang Yanling,
Wei Xialan,
Cui Mengyao,
Ju Zhiyu,
Xu Zhihong
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002608
Subject(s) - chemistry , tyrosinase , antioxidant , phenylethanoid , dpph , glycoside , glycosylation , total synthesis , stereochemistry , organic chemistry , biochemistry , enzyme
Total synthesis of six natural phenylethanoid glycosides (PhEGs) has been accomplished. Key steps in the divergent synthesis strategy involved glycosylation based on trichloroacetimidate donors, and one‐pot removal of benzyl and 4,6‐ O ‐benzylidene acetal groups by hydrogenation over Pd/C. Among them, four natural PhEGs, scroside D ( 2 ), rebouoside B ( 3 ), ginkgoside C ( 4 ), and ginkgoside D ( 5 ) were synthesized for the first time. In the subsequent antioxidant and tyrosinase inhibitory activities evaluation, all compounds showed strong DPPH radical scavenging activities, and compounds 1 – 2 , 5 – 6 exhibited obvious inhibitory activities against mushroom tyrosinase.