Anti-inflammatory and PPAR transactivational effects of components from the stem bark of ginkgo biloba

Nguyen Thi Thanh Ngan, Tran Hong Quang, Bui Huu Tai, Seok Bean Song, Dongho Lee, Young Ho Kim

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Ginkgo biloba, which is considered a "living fossil", has been used for medicinal purposes for thousands of years. Currently, extracts of G. biloba are some of the most widely used herbal products and/or dietary supplements in the world. In this study, three new compounds, (2E,4E,1′R,3′S,5′R,8′S)-dihydrophaseic acid 3′-O-β-d-glucopyranoside (1), 7,8-dihydro-(R)-7-methoxyconiferyl alcohol (2), and (8S)-3-methoxy-8,4′-oxyneolignan-4,9,9′-triol 3′-O-β-d-glucopyranoside (3), and 13 known compounds (4-16) were isolated from the stem bark of G. biloba. Their structures were determined by extensive spectroscopic methods, including 1D and 2D NMR, MS, and circular dichroism spectra. Four of the compounds (1, 2, 7, and 10) inhibited TNFα-induced NF-κB transcriptional activity significantly in HepG2 cells in a dose-dependent manner, with IC 50 values ranging from 6.9 to 9.1 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed based on decreases in COX-2 and iNOS gene expression in HepG2 cells. Compounds 1-5, 7, 9, 10, and 12-14 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC 50 values ranging from 0.7 to 12.8 μM. Compounds 2, 3, and 12 exhibited dose-dependent PPARα transactivational activity, with EC 50 values of 7.0, 3.3, and 10.1 μM, respectively. Compounds 1-3 activated PPARγ transcriptional activity, with EC 50 values of 11.9, 11.0, and 15.3 μM, whereas compounds 1 and 3 promoted the transactivational activity of PPARβ(δ) with EC 50 values of 10.7 and 11.2 μM, respectively. These results provide a scientific support for the use of G. biloba stem bark for the prevention and treatment of inflammatory and metabolic diseases. Moreover, these data provide the rationale for further studies of the potential of G. biloba stem bark in functional foods.

Original languageEnglish
Pages (from-to)2815-2824
Number of pages10
JournalJournal of Agricultural and Food Chemistry
Volume60
Issue number11
DOIs
Publication statusPublished - 2012 Mar 21

Fingerprint

Ginkgo biloba
Peroxisome Proliferator-Activated Receptors
bark
Anti-Inflammatory Agents
stems
Hep G2 Cells
Dietary supplements
dosage
circular dichroism spectroscopy
Dichroism
Functional Food
Gene expression
Metabolic Diseases
metabolic diseases
prostaglandin synthase
Dietary Supplements
Circular Dichroism
functional foods
Alcohols
Nuclear magnetic resonance

Keywords

  • GAL-4-PPAR chimera assay
  • Ginkgo biloba
  • NF-κB-luciferase assay
  • PPRE-luciferase assay
  • RT-PCR

ASJC Scopus subject areas

  • Agricultural and Biological Sciences(all)
  • Chemistry(all)

Cite this

Anti-inflammatory and PPAR transactivational effects of components from the stem bark of ginkgo biloba. / Ngan, Nguyen Thi Thanh; Quang, Tran Hong; Tai, Bui Huu; Song, Seok Bean; Lee, Dongho; Kim, Young Ho.

In: Journal of Agricultural and Food Chemistry, Vol. 60, No. 11, 21.03.2012, p. 2815-2824.

Research output: Contribution to journalArticle

Ngan, Nguyen Thi Thanh ; Quang, Tran Hong ; Tai, Bui Huu ; Song, Seok Bean ; Lee, Dongho ; Kim, Young Ho. / Anti-inflammatory and PPAR transactivational effects of components from the stem bark of ginkgo biloba. In: Journal of Agricultural and Food Chemistry. 2012 ; Vol. 60, No. 11. pp. 2815-2824.
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N2 - Ginkgo biloba, which is considered a "living fossil", has been used for medicinal purposes for thousands of years. Currently, extracts of G. biloba are some of the most widely used herbal products and/or dietary supplements in the world. In this study, three new compounds, (2E,4E,1′R,3′S,5′R,8′S)-dihydrophaseic acid 3′-O-β-d-glucopyranoside (1), 7,8-dihydro-(R)-7-methoxyconiferyl alcohol (2), and (8S)-3-methoxy-8,4′-oxyneolignan-4,9,9′-triol 3′-O-β-d-glucopyranoside (3), and 13 known compounds (4-16) were isolated from the stem bark of G. biloba. Their structures were determined by extensive spectroscopic methods, including 1D and 2D NMR, MS, and circular dichroism spectra. Four of the compounds (1, 2, 7, and 10) inhibited TNFα-induced NF-κB transcriptional activity significantly in HepG2 cells in a dose-dependent manner, with IC 50 values ranging from 6.9 to 9.1 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed based on decreases in COX-2 and iNOS gene expression in HepG2 cells. Compounds 1-5, 7, 9, 10, and 12-14 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC 50 values ranging from 0.7 to 12.8 μM. Compounds 2, 3, and 12 exhibited dose-dependent PPARα transactivational activity, with EC 50 values of 7.0, 3.3, and 10.1 μM, respectively. Compounds 1-3 activated PPARγ transcriptional activity, with EC 50 values of 11.9, 11.0, and 15.3 μM, whereas compounds 1 and 3 promoted the transactivational activity of PPARβ(δ) with EC 50 values of 10.7 and 11.2 μM, respectively. These results provide a scientific support for the use of G. biloba stem bark for the prevention and treatment of inflammatory and metabolic diseases. Moreover, these data provide the rationale for further studies of the potential of G. biloba stem bark in functional foods.

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