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

研究成果: 雜誌貢獻文章

19 引文 (Scopus)

摘要

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.

原文英語
頁(從 - 到)580-587
頁數8
期刊Journal of Natural Products
76
發行號4
DOIs
出版狀態已發佈 - 四月 26 2013

指紋

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

引用此文

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.

於: Journal of Natural Products, 卷 76, 編號 4, 26.04.2013, p. 580-587.

研究成果: 雜誌貢獻文章

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, 卷 76, 編號 4, 頁 580-587. https://doi.org/10.1021/np3007638
Yang Kuo LM, Zhang LJ, Huang HT, Lin ZH, Liaw CC, Cheng HL 等. Antioxidant lignans and chromone glycosides from Eurya japonica. Journal of Natural Products. 2013 4月 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. 於: Journal of Natural Products. 2013 ; 卷 76, 編號 4. 頁 580-587.
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title = "Antioxidant lignans and chromone glycosides from Eurya japonica",
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 - Yang Kuo, Li Ming

AU - Zhang, Li Jie

AU - Huang, Hung Tse

AU - Lin, Zhi Hu

AU - Liaw, Chia Ching

AU - Cheng, Hui Ling

AU - Lee, Kuo Hsiung

AU - Morris-Natschke, Susan L.

AU - Kuo, Yao Haur

AU - Ho, Hsiu O.

PY - 2013/4/26

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N2 - 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.

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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