2018Chemistry & BiodiversityRequires access

Two New Chromone Glycosides from the Roots of Saposhnikovia divaricata

Si‐Yuan Ma, Linggao Shi, Zheng‐Bing Gu, Yulan Wu, Liu‐Bin Wei, Qiqiu Wei, Xing‐Ling Gao, Na Liao

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Abstract

Five chromone glycosides were isolated from the water‐soluble portions of 70% Et OH extract of the roots of Saposhnikovia divaricata , including two new chromone glycosides 1 and 2 . The structures of the chromone glycosides were identified as (3′ S )‐3′‐ O‐β ‐ d ‐apiofuranosyl‐(1 → 6)‐ β ‐ d ‐glucopyranosylhamaudol ( 1 ), (2′ S )‐4′‐ O ‐ β ‐ d ‐apiofuranosyl‐(1 → 6)‐ β ‐ d ‐glucopyranosylvisamminol ( 2 ), 3′‐ O ‐glucopyranosylhamaudol ( 3 ), 4′‐ O‐β ‐ d ‐glucopyranosylvisamminol ( 4 ), and 4′‐ O‐β ‐ d ‐glucopyranosyl‐5‐ O ‐methylvisamminol ( 5 ) on the basis of extensive spectroscopic methods, and the absolute configurations of the new compounds were elucidated by the electronic circular dichroism ( ECD ) calculation and acid hydrolysis. The cytotoxic activities of the glycosides 1 – 5 against three human cancer cell lines ( PC ‐3, SK ‐ OV ‐3, and H460) were evaluated. The result showed that compounds 1 – 5 had weak cytotoxic activities against the human cancer cell lines with IC 50 values in the range of 48.54 ± 0.80 – 94.25 ± 1.45 μ m .

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What this paper is about

Five chromone glycosides were isolated from the water‐soluble portions of 70% Et OH extract of the roots of Saposhnikovia divaricata , including two new chromone glycosides 1 and 2 . The structures of the chromone glycosides were identified as (3′ S )‐3′‐ O‐β ‐ d ‐apiofuranosyl‐(1 → 6)‐ β ‐ d ‐glucopyranosylhamaudol ( 1 ), (2′ S )‐4′‐ O ‐ β ‐ d ‐apiofuranosyl‐(1 → 6)‐ β ‐ d ‐glucopyranosylvisamminol ( 2 ), 3′‐ O ‐glucopyranosylhamaudol ( 3 ), 4′‐ O‐β ‐ d ‐glucopyranosylvisamminol ( 4 ), and 4′‐ O‐β ‐ d ‐glucopyranosyl‐5‐ O ‐methylvisamminol ( 5 ) on the basis of extensive spectroscopic methods, and the absolute configurations of the new compounds were elucidated by the electronic circular dichroism ( ECD ) calculation and acid hydrolysis. The cytotoxic activities of the glycosides 1 – 5 against three human cancer cell lines ( PC ‐3, SK ‐ OV ‐3, and H460) were evaluated. The result showed that compounds 1 – 5 had weak cytotoxic activities against the human cancer cell lines with IC 50 values in the range of 48.54 ± 0.80 – 94.25 ± 1.45 μ m .

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Available abstract

Five chromone glycosides were isolated from the water‐soluble portions of 70% Et OH extract of the roots of Saposhnikovia divaricata , including two new chromone glycosides 1 and 2 . The structures of the chromone glycosides were identified as (3′ S )‐3′‐ O‐β ‐ d ‐apiofuranosyl‐(1 → 6)‐ β ‐ d ‐glucopyranosylhamaudol ( 1 ), (2′ S )‐4′‐ O ‐ β ‐ d ‐apiofuranosyl‐(1 → 6)‐ β ‐ d ‐glucopyranosylvisamminol ( 2 ), 3′‐ O ‐glucopyranosylhamaudol ( 3 ), 4′‐ O‐β ‐ d ‐glucopyranosylvisamminol ( 4 ), and 4′‐ O‐β ‐ d ‐glucopyranosyl‐5‐ O ‐methylvisamminol ( 5 ) on the basis of extensive spectroscopic methods, and the absolute configurations of the new compounds were elucidated by the electronic circular dichroism ( ECD ) calculation and acid hydrolysis. The cytotoxic activities of the glycosides 1 – 5 against three human cancer cell lines ( PC ‐3, SK ‐ OV ‐3, and H460) were evaluated. The result showed that compounds 1 – 5 had weak cytotoxic activities against the human cancer cell lines with IC 50 values in the range of 48.54 ± 0.80 – 94.25 ± 1.45 μ m .

Key concepts: Chromone, Chemistry, Glycoside, Stereochemistry, Circular dichroism, Hydrolysis, Cancer cell lines, Cytotoxicity

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