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Diarylheptanoids and Flavonoids from Viscum album Inhibit LPS-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells

2013; American Chemical Society; Volume: 76; Issue: 4 Linguagem: Inglês

10.1021/np300490v

1520-6025

Nguyễn Xuân Nhiệm, Phan Văn Kiệm, Châu Văn Minh, Nanyoung Kim, SeonJu Park, Hwa Young Lee, Eun Sil Kim, Young Ho Kim, Sohyun Kim, Young Sang Koh, Seung‐Hyun Kim,

Natural product bioactivities and synthesis

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-[6‴-(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-6‴-(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 IC50 value of 2.00 ± 0.15 μM.