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

Research output: Contribution to journalArticle

17 Citations (Scopus)

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

Fingerprint

Diarylheptanoids
Viscum album
Interleukin-12 Subunit p40
Flavonoids
Dendritic Cells
Bone
Bone Marrow
Cytokines
Glycosides
Interleukin-6
Inhibitory Concentration 50
3-methylquercetin

All Science Journal Classification (ASJC) codes

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

Cite this

Nhiem, Nguyen X. ; Kiem, Phan V. ; Minh, Chau V. ; Kim, Nanyoung ; Park, Seonju ; Lee, Hwa Young ; Kim, Eun Sil ; Kim, Young Ho ; Kim, Sohyun ; Koh, Young Sang ; Kim, Seung Hyun. / Diarylheptanoids and flavonoids from Viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. In: Journal of Natural Products. 2013 ; Vol. 76, No. 4. pp. 495-502.
@article{79fa3d1c0aae41e3b5249e458b837a05,
title = "Diarylheptanoids and flavonoids from Viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells",
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.",
author = "Nhiem, {Nguyen X.} and Kiem, {Phan V.} and Minh, {Chau V.} and Nanyoung Kim and Seonju Park and Lee, {Hwa Young} and Kim, {Eun Sil} and Kim, {Young Ho} and Sohyun Kim and Koh, {Young Sang} and Kim, {Seung Hyun}",
year = "2013",
month = "4",
day = "26",
doi = "10.1021/np300490v",
language = "English",
volume = "76",
pages = "495--502",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "4",

}

Diarylheptanoids and flavonoids from Viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. / Nhiem, Nguyen X.; Kiem, Phan V.; Minh, Chau V.; Kim, Nanyoung; Park, Seonju; Lee, Hwa Young; Kim, Eun Sil; Kim, Young Ho; Kim, Sohyun; Koh, Young Sang; Kim, Seung Hyun.

In: Journal of Natural Products, Vol. 76, No. 4, 26.04.2013, p. 495-502.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Diarylheptanoids and flavonoids from Viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells

AU - Nhiem, Nguyen X.

AU - Kiem, Phan V.

AU - Minh, Chau V.

AU - Kim, Nanyoung

AU - Park, Seonju

AU - Lee, Hwa Young

AU - Kim, Eun Sil

AU - Kim, Young Ho

AU - Kim, Sohyun

AU - Koh, Young Sang

AU - Kim, Seung Hyun

PY - 2013/4/26

Y1 - 2013/4/26

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84876911664&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84876911664&partnerID=8YFLogxK

U2 - 10.1021/np300490v

DO - 10.1021/np300490v

M3 - Article

VL - 76

SP - 495

EP - 502

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 4

ER -