Journal of Food Science and Technology

, Volume 55, Issue 5, pp 1850–1858 | Cite as

Effects of alginate oligosaccharides with different molecular weights and guluronic to mannuronic acid ratios on glyceollin induction and accumulation in soybeans

  • Qing Peng
  • Mimin Zhang
  • Long Gao
  • Ojokoh Eromosele
  • Yu Qiao
  • Bo Shi
Original Article


Alginate oligosaccharides (AOs) are linear oligosaccharides with alternating sequences of mannuronic acid (M) and guluronic acid (G) residues. AOs can be used as a safe elicitor to induce glyceollins, which have many human health benefits, in soybean seeds. In this research, four AO fractions with different chemical structures and molecular weights were separated, purified, and then characterized by NMR spectroscopy and ESI–MS. With a 4,5-unsaturated hexuronic acid residue (△) at the non-reducing terminus, the structures of these four AO fractions were △G, △MG, △GMG and △MGGG, which exhibited glyceollin-inducing activities of 1.2339, 0.3472, 0.6494 and 1.0611 (mg/g dry weight) in soybean seeds, respectively. The results demonstrated that a larger molecular weight or a higher G/M ratio might correlate with a higher glyceollin-inducing activity. Moreover, the alginate disaccharide △G could be introduced as relatively safe and efficient elicitor of high glyceollin content in soybeans.


Alginate oligosaccharides Glyceollin Soybean Molecular weight Ratio of guluronic to mannuronic acid (G/M) 



Alginate oligosaccharide


Guluronic acid


Mannuronic acid


High-performance liquid chromatography


Nuclear magnetic resonance


Electrospray ionization–mass spectrometry


Solid phase extraction


Trifluoroacetic acid

O-(4-deoxy-α-l-erythro-hex-4-enopyranosyluronic acid)-(1→


→4)-O-(α-l-gulopyranosyluronic acid)-(1→


→4)-O-β-l-gulopyranuronic acid


→4)-O-(β-d-mannopyranuronic acid)-(1→



We gratefully acknowledge the moral and financial support received from the National Natural Science Foundation of China (No. 31171628).

Compliance with ethical standards

Conflict of interest

There are no conflicts of interest. The author and co-authors alone are responsible for the content and writing of this paper.

Supplementary material

13197_2018_3101_MOESM1_ESM.eps (804 kb)
Supplemental Fig. 1 1H NMR (500 MHz) spectra of (a) F1, (b) F3, (c) F5 and (d) F7. The experimental temperature was 25 °C. The water peak was 4.70 (EPS 804 kb)
13197_2018_3101_MOESM2_ESM.eps (704 kb)
Supplemental Fig. 2 13C NMR (125 MHz) spectra of (a) F1, (b) F3, (c) F5 and (d) F7. The experimental temperature was 25 °C (EPS 704 kb)
13197_2018_3101_MOESM3_ESM.eps (2.8 mb)
Supplemental Fig. 3 2D NMR spectra of F1 (△G) obtained at 500 MHz at 25 °C. (a) COSY, (b) HSQC, and (c) HMBC (EPS 2867 kb)
13197_2018_3101_MOESM4_ESM.eps (1.6 mb)
Supplemental Fig. 4 2D NMR spectra of F3 (△MG) obtained at 500 MHz at 25 °C. (a) COSY, (b) HSQC, and (c) HMBC (EPS 1645 kb)
13197_2018_3101_MOESM5_ESM.eps (2 mb)
Supplemental Fig. 5 2D NMR spectra of F5 (△GMG) obtained at 500 MHz at 25 °C. (a) COSY, (b) HSQC, and (c) HMBC (EPS 2008 kb)
13197_2018_3101_MOESM6_ESM.eps (3.5 mb)
Supplemental Fig. 6 2D NMR spectra of F7 (△MGGG) obtained at 500 MHz at 25 °C. (a) COSY, (b) HSQC, and (c) HMBC (EPS 3585 kb)


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Copyright information

© Association of Food Scientists & Technologists (India) 2018

Authors and Affiliations

  • Qing Peng
    • 1
  • Mimin Zhang
    • 2
  • Long Gao
    • 1
  • Ojokoh Eromosele
    • 1
  • Yu Qiao
    • 1
  • Bo Shi
    • 1
  1. 1.Key Laboratory for Feed Biotechnology of the Ministry of Agriculture, Feed Research InstituteChinese Academy of Agricultural SciencesBeijingPeople’s Republic of China
  2. 2.Department of Applied Biological Chemistry, Graduate School of Agricultural and Life SciencesThe University of TokyoTokyoJapan

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