New Phenylethanoid Glycosides from Cistanche phelypaea and Their Activity as Inhibitors of Monoacylglycerol Lipase (MAGL)
Khadidja Aya BeladjilaDjemaa BerrehalNunziatina De TommasiCarlotta GranchiGiulia BononiAlessandra BracaMarinella De Leo
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Four new phenylethanoid glycosides (1: -4: ), 1-β-p-hydroxyphenyl-ethyl-2-O-acetyl-3,6-di-α-l-rhamnopyranosyl-β-d-glucopyranoside (1: ), 1-β-p-hydroxyphenyl-ethyl-3,6-O-di-α-l-rhamnopyranosyl-β-d-glucopyranoside (2: ), 1-β-p-hydroxyphenyl-ethyl-2-O-acetyl-3,6-di-α-l-rhamnopyranosyl-4-p-coumaroyl-β-d-glucopyranoside (3: ), and 1-β-p-hydroxyphenyl-ethyl-3,6-di-α-l-rhamnopyranosyl-4-p-coumaroyl-β-d-glucopyranoside (4: ), together with three known compounds, were isolated from the n-butanol extract of Cistanche phelypaea aerial parts. The structural characterization of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The isolated compounds were assayed for their inhibitory activity on two enzymes involved in the peculiar glycolytic or lipidic metabolism of cancer cells, human lactate dehydrogenase (LDH), and monoacylglycerol lipase (MAGL), respectively. All the compounds showed negligible activity on LDH, whereas some of them displayed a certain inhibition activity on MAGL. In particular, compound 1: was the most active on MAGL, showing an IC50 value of 88.0 µM, and modeling studies rationalized the supposed binding mode of 1: in the MAGL active site.Keywords:
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Phenylethanoid
Isolation and Characterization of Glycosidic Tyrosinase Inhibitors from Typhonium giganteum Rhizomes
A new hydrocinnamoyl glucoside, 1-O-(4-hydroxyhydrocinnamoyl)-β-D-glucopyranose (1), together with fifteen known glycosides, including two phenylethanoid glycosides (2–3), two cinnamoyl glycosides (4–5), six phenolic glycosides (6–11), one lignan glycoside (12) and four megastigmane glycosides (13–16) were isolated from a 95% EtOH extract of the Typhonium giganteum rhizomes. The sixteen glycosides were structurally characterized by NMR, HRESIMS, enzymatic hydrolysis and comparison with literature. Upon evaluating inhibitory activities of compounds 1–16 against mushroom tyrosinase at 25 μM, compounds 10 and 11 exhibited obvious inhibitory activities, with %inhibition values of 20.94±0.59%, 23.28±1.09%, respectively, with arbutin used as the positive control (26.21±0.58%).
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OBJECTIVE To study the inhibitory effects of phenylethanoid glycosides of Cistanche on the activity of tyrosinase. METHODS The inbibition of phenylethanoid glycosides on tyrosinase was estimated with L-Tryosine substrate and its inhibitory pattern was determined according to the Lineweaver-Burk curve. RESULTS The phenylethanoid glycosides has showed a strong inhibition on the activity of tyosinase. The inhibition of tyrosinase by phenylethanoid glycosides was a reversible reaction with remaining enzyme activity and its inhibitory mechanism belonged to be competitive. CONCLUSION This study has provided the evidence for further exploiting skin-whitening agent from the plants of Cistanche Hoffing. et Link.
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Four new megastigmane glycosides, named gusanlungionosides A–D (1–4), together with 10 known compounds (5–14), were isolated from the stems of Arcangelisia gusanlung. The structures and absolute configurations of 1–4 were elucidated by comprehensive analysis of their NMR and CD data. Compounds 1–4 exhibited strong inhibitory effects not only on the mushroom tyrosinase activity in vitro but also on melanogenesis in cells.
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Abstract 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.
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Activity guided isolation of a MeOH extract of the aerial plant parts of Wulfenia carinthiaca Jacq. (Plantaginaceae), using a mushroom tyrosinase assay, resulted in the isolation of five phenylethanoid glucosides and four iridoid glycosides. Two of them, 2'-O-acetylisoplantamajoside and 2',6″-O-diacetylisoplantamajoside, represent new natural products. Evaluation of the inhibitory activity of all isolated compounds revealed that the observed activity is not related to the isolated phenylethanoid glycosides but mainly due to the presence of the iridoid glycoside globularin (IC50 41.94 μm; CI95% ± 16.61/11.89 μm). Interestingly, structurally close related compounds (globularicisin, baldaccioside, and isoscrophularioside) showed no or only a weak tyrosinase inhibitory activity.
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