Antioxidant lignans and chromone glycosides from Eurya japonica

Li Ming Yang Kuo, Li Jie Zhang, Hung Tse Huang, Zhi Hu Lin, Chia Ching Liaw, Hui Ling Cheng, Kuo Hsiung Lee, Susan L. Morris-Natschke, Yao Haur Kuo, Hsiu O. Ho

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19 Citations (Scopus)

Abstract

Four new 8,8′,7,2′-lignans, (+)-ovafolinin B-9′-O-β- d-glucopyranoside (1), (-)-ovafolinin B-9′-O-β-d-glucopyranoside (2), (+)-ovafolinin E-9′-O-β-d-glucopyranoside (3), and (-)-ovafolinin E-9′-O-β-d-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neolignan-9, 9′-diol-4-O-β-d-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-glucopyranoside (7) and 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 μM for 1) demonstrated potent antioxidant activity compared to the positive control α-tocopherol (ED50 27.21 μM). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin.

Original languageEnglish
Pages (from-to)580-587
Number of pages8
JournalJournal of Natural Products
Volume76
Issue number4
DOIs
Publication statusPublished - Apr 26 2013

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Chromones
Lignans
Glycosides
Antioxidants
Tocopherols
Quercetin
Circular Dichroism
Nuclear magnetic resonance

ASJC Scopus subject areas

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

Cite this

Yang Kuo, L. M., Zhang, L. J., Huang, H. T., Lin, Z. H., Liaw, C. C., Cheng, H. L., ... Ho, H. O. (2013). Antioxidant lignans and chromone glycosides from Eurya japonica. Journal of Natural Products, 76(4), 580-587. https://doi.org/10.1021/np3007638

Antioxidant lignans and chromone glycosides from Eurya japonica. / Yang Kuo, Li Ming; Zhang, Li Jie; Huang, Hung Tse; Lin, Zhi Hu; Liaw, Chia Ching; Cheng, Hui Ling; Lee, Kuo Hsiung; Morris-Natschke, Susan L.; Kuo, Yao Haur; Ho, Hsiu O.

In: Journal of Natural Products, Vol. 76, No. 4, 26.04.2013, p. 580-587.

Research output: Contribution to journalArticle

Yang Kuo, LM, Zhang, LJ, Huang, HT, Lin, ZH, Liaw, CC, Cheng, HL, Lee, KH, Morris-Natschke, SL, Kuo, YH & Ho, HO 2013, 'Antioxidant lignans and chromone glycosides from Eurya japonica', Journal of Natural Products, vol. 76, no. 4, pp. 580-587. https://doi.org/10.1021/np3007638
Yang Kuo LM, Zhang LJ, Huang HT, Lin ZH, Liaw CC, Cheng HL et al. Antioxidant lignans and chromone glycosides from Eurya japonica. Journal of Natural Products. 2013 Apr 26;76(4):580-587. https://doi.org/10.1021/np3007638
Yang Kuo, Li Ming ; Zhang, Li Jie ; Huang, Hung Tse ; Lin, Zhi Hu ; Liaw, Chia Ching ; Cheng, Hui Ling ; Lee, Kuo Hsiung ; Morris-Natschke, Susan L. ; Kuo, Yao Haur ; Ho, Hsiu O. / Antioxidant lignans and chromone glycosides from Eurya japonica. In: Journal of Natural Products. 2013 ; Vol. 76, No. 4. pp. 580-587.
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abstract = "Four new 8,8′,7,2′-lignans, (+)-ovafolinin B-9′-O-β- d-glucopyranoside (1), (-)-ovafolinin B-9′-O-β-d-glucopyranoside (2), (+)-ovafolinin E-9′-O-β-d-glucopyranoside (3), and (-)-ovafolinin E-9′-O-β-d-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neolignan-9, 9′-diol-4-O-β-d-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-glucopyranoside (7) and 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 μM for 1) demonstrated potent antioxidant activity compared to the positive control α-tocopherol (ED50 27.21 μM). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin.",
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AU - Cheng, Hui Ling

AU - Lee, Kuo Hsiung

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AU - Kuo, Yao Haur

AU - Ho, Hsiu O.

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AB - Four new 8,8′,7,2′-lignans, (+)-ovafolinin B-9′-O-β- d-glucopyranoside (1), (-)-ovafolinin B-9′-O-β-d-glucopyranoside (2), (+)-ovafolinin E-9′-O-β-d-glucopyranoside (3), and (-)-ovafolinin E-9′-O-β-d-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neolignan-9, 9′-diol-4-O-β-d-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-glucopyranoside (7) and 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 μM for 1) demonstrated potent antioxidant activity compared to the positive control α-tocopherol (ED50 27.21 μM). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin.

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