A new flavonol glycoside from Hylomecon vernalis

• Published in: Archives of pharmacal research Vol. 35; no. 3; pp. 415 - 421
• Main Authors: Lee, Seung Young, Kim, Ki Hyun, Lee, Il Kyun, Lee, Kyu Ha, Choi, Sang Un, Lee, Kang Ro
• Format: Journal Article
• Language: English
• Published: Heidelberg Pharmaceutical Society of Korea 01.03.2012; 대한약학회
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Cell Line, Tumor; Cell Survival - drug effects; Chromatography; Dose-Response Relationship, Drug; Flavonols - chemistry; Flavonols - isolation & purification; Flavonols - pharmacology; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Humans; Inhibitory Concentration 50; Magnetic Resonance Spectroscopy; Medicine; Methanol - chemistry; Molecular Structure; Papaveraceae - chemistry; Pharmacology/Toxicology; Pharmacy; Plant Components, Aerial; Solvents - chemistry; 약학; Acetylated flavonol glycoside; Papaveraceae
• ISSN: 0253-6269; 1976-3786
• DOI: 10.1007/s12272-012-0303-8

Purification of a MeOH extract from the aerial parts of Hylomecon vernalis Maxim. (Papaveraceae) using column chromatography furnished a new acetylated flavonol glycoside ( 1 ), together with twenty known phenolic compounds ( 2–21 ). Structural elucidation of 1 was based on 1D- and 2D-NMR spectroscopy data analysis to be quercetin 3- O -[4‴- O -acetyl-α-L-arabinopyranosyl]-(1‴→6″)-β-D-galactopyranoside ( 1 ). The structures of compounds 2–21 were elucidated by spectroscopy and confirmed by comparison with reported data; quercetin 3- O -[2‴- O -acetyl-α-L-arabinopyranosyl]-(1‴→6″)-β -D-galactopyranoside ( 2 ), quercetin 3- O -α-L-arabinopyranosyl-(1‴→6″)-β-D-galactopyranoside ( 3 ), quercetin 3- O -β -D-galactopyranoside ( 4 ), kaempferol 3,7- O -α-L-dirhamnopyranoside ( 5 ), diosmetin 7- O -β -D-glucopyranoside ( 6 ), diosmetin 7- O -β -D-xylopyranosyl-(1‴→6″)-β-D-glucopyranoside ( 7 ), p -hydroxybenzoic acid ( 8 ), protocatechuic acid ( 9 ), caffeic acid ( 10 ), 6-hydroxy-3,4-dihydro-1-oxo-β -carboline ( 11 ), ( Z )-3-hexenyl-β -D-glucopyranoside ( 12 ), ( E )-2-hexenyl-β -D-glucopyranoside ( 13 ), ( Z )-3-hexenyl-α-Larabinopyranosyl-(1″→6′)-β-D-glucopyranoside ( 14 ), oct-1-en-3-yl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside ( 15 ), benzyl-β-D-apiofuranosyl-(1″→6′)-β-D-glucopyranoside ( 16 ), benzyl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside ( 17 ), benzyl-β-D-xylopyranosyl-(1″→6′)-β-Dglucopyranoside ( 18 ), 2-phenylethyl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside ( 19 ), 2-phenylethyl-β-D-apiofuranosyl-(1″→6′)-β-D-glucopyranoside ( 20 ), and aryl-β-D-glucopyranoside ( 21 ). Compounds 2 - 21 were isolated for the first time from this plant. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.