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Journal of Natural Medicines

, Volume 72, Issue 3, pp 808–815 | Cite as

Chemical constituents from Canarium album Raeusch and their anti-influenza A virus activities

  • Luo-Ping Yang
  • Xiao-Long Gu
  • Jin-Xiang Chen
  • Jie Yang
  • Sui-Yi Tan
  • Wen-Jun Duan
Note

Abstract

Two new dyhydrophaseic acid glucoside isomers, (1′S, 3′R, 5′S, 8′R, 2Z, 4E)-dihydrophaseic acid-3′-O-β-d-glucopyranoside (2) and (1′R, 3′S, 5′R, 8′R, 2Z, 4E)-dihydrophaseic acid-3′-O-β-d-glucopyranoside (4), together with 10 known compounds [myo-inositol (1), 3,4-dihydroxybenzoic acid (3), 3-O-galloyl quinic acid (5), ellagic acid (6), gallic acid (7), ethyl gallate (8), scopoletin (9), ellagic acid-4-O-β-d-glucopyranoside (10), ellagic acid-4-O-α-l-rhamnopyranoside (11), and isocorilagin (12)] were isolated from the chloroform extract of Canarium album Raeusch fruits by repeated chromatography on macroporous adsorption resin, silica gel, Sephadex LH-20, Toyopearl HW-40F, and reverse-phase C18 columns, etc. Their structures and absolute configurations were determined by comprehensive analysis of 1D- and 2D-nuclear magnetic resonance (NMR), high-resolution electron spray ionization mass spectrometry (HR-ESI–MS), ESI–MS, optical rotation, circular dichroism spectra, and comparison of NMR data with data of known compounds. Bioassay of their anti-influenza virus A activities showed that compounds 9 and 12 displayed a significant inhibitory effect with IC50 values of 22.9 ± 3.7 and 5.42 ± 0.97 μg/ml, respectively.

Keywords

Canarium album Raeusch fruit Chloroform extract Dihydrophaseic acid glucopyranoside isomer Anti-influenza virus A activities 

Notes

Acknowledgements

We thank the fund of Science and Technology Program of Guangzhou, China (No. 2014J4100159), and Undergraduate Training Program for Innovation and Entrepreneurship of Guangdong province, China (No. 201512121079). We also express our thanks to the State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology for their technical assistance for performing HR-ESI-MS.

Compliance with ethical standards

Conflict of interest

The authors declare no competing interests.

Supplementary material

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Supplementary material 1 (PDF 120 kb)
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Supplementary material 9 (PDF 182 kb)
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Supplementary material 10 (PDF 148 kb)
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Supplementary material 11 (PDF 194 kb)
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Supplementary material 12 (PDF 298 kb)

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK, part of Springer Nature 2018

Authors and Affiliations

  • Luo-Ping Yang
    • 1
  • Xiao-Long Gu
    • 1
  • Jin-Xiang Chen
    • 1
  • Jie Yang
    • 1
  • Sui-Yi Tan
    • 1
  • Wen-Jun Duan
    • 1
  1. 1.School of Pharmaceutical SciencesSouthern Medical UniversityGuangzhouChina

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