Isolation and Structural Elucidation of Unreported Prenylhydroquinone Glycoside from Sedum kamtschaticum Leaves and Its Effect on Hyperphosphorylated Tau Production in Aβ1–42-Treated SH-SY5Y Cells

Sedum kamtschaticum Fischer, of the Crassulaceae family, is a perennial and medicinal plant used in Asian folk medicine to alleviate inflammatory disease and improve blood circulation. As part of our ongoing exploration into natural products, seeking to identifying bioactive compounds, we characteri...

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Published inSeparations Vol. 10; no. 8; p. 428
Main Authors Lee, Seung-Eun, Jeong, Se Yun, Jang, Yoon Seo, Cho, Kwang-Jin, Lee, Jeonghoon, Lee, Yunji, Kim, Ki Hyun
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.08.2023
Subjects
Accumulation
Alzheimer's disease
Biological activity
Blood circulation
Cell growth
Crassulaceae
Glycosides
Herbal medicine
Ions
Natural products
NMR
Nuclear magnetic resonance
Planar structures
prenylhydroquinone glycoside
Sedum kamtschaticum
SH-SY5Y cells
Spectrum analysis
structural elucidation
tau
United States > US
Japan
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Summary:Sedum kamtschaticum Fischer, of the Crassulaceae family, is a perennial and medicinal plant used in Asian folk medicine to alleviate inflammatory disease and improve blood circulation. As part of our ongoing exploration into natural products, seeking to identifying bioactive compounds, we characterized, identified, and isolated an unreported bioactive compound, prenylhydroquinone glycoside (1), which we named kirinchoside from S. kamtschaticum leaves. Using high-resolution (HR)-ESIMS, NMR spectroscopic data, and enzymatic hydrolysis, followed by LC–MS analysis, we determined the structure of this isolated compound. Despite a previous report on the planar structure of compound 1 (kirinchoside), the absolute configuration of 1 had not been verified. We investigated the effects of kirinchoside on hyperphosphorylated tau (p-tau) accumulation, a hallmark of Alzheimer’s disease (AD) progression. We observed that treatment with 5 μM kirinchoside suppressed p-tau levels by 16.9% in amyloid β (Aβ)1–42-treated SH-SY5Y cells, compared to the negative control. These findings indicate that kirinchoside, an unreported prenylhydroquinone glycoside found in S. kamtschaticum leaves, could be a candidate preventive agent against AD via inhibition of p-tau accumulation.
ISSN:2297-8739
2297-8739
DOI:10.3390/separations10080428