Diarylheptanoids and flavonoids from Viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells

Nguyen X. Nhiem, Phan V. Kiem, Chau V. Minh, Nanyoung Kim, Seonju Park, Hwa Young Lee, Eun Sil Kim, Young Ho Kim, Sohyun Kim, Young Sang Koh, Seung Hyun Kim

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Abstract

Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4- hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4- hydroxyphenyl)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E- hepten-5-one (3), four new flavonoid glycosides, 3,7,3′-tri-O- methylquercetin-4′-O-β-d-apiofuranosyl-(1→2)-O-β-d- glucopyranoside (4), 7,3′-di-O-methylquercetin-4′-O-β-d- glucopyranosyl-3-O-[6́-(3-hydroxy-3-methylglutaroyl)]-α-d- glucopyranoside (5), 7,3′-di-O-methylquercetin-4′-O-β-d- glucopyranosyl-3-O-[(6′′′′′→5′′ ′′)-O-1′′′′′-(sinap-4-yl) -β-d-glucopyranosyl-6́-(3-hydroxy-3-methylglutaroyl)] -α-d-glucopyranoside (6), and (2S)-5-hydroxy-7,3′- dimethoxyflavanone-4′-O-β-d-apiofuranosyl-(1→5) -O-β-d-apiofuranosyl-(1→2)-O-β-d-glucopyranoside (9), and 17 known compounds were isolated from the leaves and twigs of Viscum album. Compounds 1, 4, and 19 significantly inhibited LPS-stimulated production of TNF-α, IL-6, and IL-12p40 with IC50 values ranging from 0.09 ± 0.01 to 8.96 ± 0.45 μM. (+)-Medioresinol (13) showed inhibitory effects on LPS-stimulated production of IL-12p40 with an IC 50 value of 2.00 ± 0.15 μM.

Original languageEnglish
Pages (from-to)495-502
Number of pages8
JournalJournal of Natural Products
Volume76
Issue number4
DOIs
Publication statusPublished - 2013 Apr 26

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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