Isolation and structural elucidation by 2D NMR of planteose, a major oligosaccharide in the mucilage of chia (Salvia hispanica L.) seeds

Xiaohui Xing; Yves S Y Hsieh; Kuok Yap; Main E Ang; Jelle Lahnstein; Matthew R Tucker; Rachel A Burton; Vincent Bulone

doi:10.1016/j.carbpol.2017.07.059

Isolation and structural elucidation by 2D NMR of planteose, a major oligosaccharide in the mucilage of chia (Salvia hispanica L.) seeds

Carbohydr Polym. 2017 Nov 1:175:231-240. doi: 10.1016/j.carbpol.2017.07.059. Epub 2017 Jul 23.

Authors

Xiaohui Xing¹, Yves S Y Hsieh², Kuok Yap³, Main E Ang³, Jelle Lahnstein⁴, Matthew R Tucker³, Rachel A Burton³, Vincent Bulone⁵

Affiliations

¹ Australian Research Council Centre of Excellence in Plant Cell Walls, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia; Adelaide Glycomics, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia; Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Centre, Stockholm, SE 10691, Sweden.
² Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Centre, Stockholm, SE 10691, Sweden; Wallenberg Wood Science Center, Royal Institute of Technology (KTH), Stockholm, SE 10044, Sweden.
³ Australian Research Council Centre of Excellence in Plant Cell Walls, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia.
⁴ Australian Research Council Centre of Excellence in Plant Cell Walls, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia; Adelaide Glycomics, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia.
⁵ Australian Research Council Centre of Excellence in Plant Cell Walls, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia; Adelaide Glycomics, School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA 5064, Australia; Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Centre, Stockholm, SE 10691, Sweden; Wallenberg Wood Science Center, Royal Institute of Technology (KTH), Stockholm, SE 10044, Sweden. Electronic address: [email protected].

PMID: 28917861
DOI: 10.1016/j.carbpol.2017.07.059

Abstract

An oligosaccharide was isolated in high purity and excellent yield from the water-extractable mucilage of chia (Salvia hispanica L.) seeds using an optimized solid-phase extraction method. LC-MS analysis showed that the compound presents a molecular mass of 504Da and trifluoroacetic acid hydrolysis revealed that it consists of galactose, glucose and fructose. Glycosidic linkage analysis showed that the oligosaccharide contains two non-reducing ends corresponding to terminal glucopyranose and terminal galactopyranose, respectively. The oligosaccharide was identified as planteose by the complete assignment of a series of 2D NMR spectra (COSY, TOCSY, ROESY, HSQC, and HMBC). The significance of the presence of planteose in chia seeds is discussed in the context of nutrition and food applications.

Keywords: Chia; NMR; Planteose; Salvia hispanica L; Seed mucilage; Solid-phase extraction.

MeSH terms

Oligosaccharides / chemistry*
Plant Mucilage / chemistry*
Salvia / chemistry*
Seeds / chemistry*
Water

Substances

Oligosaccharides
Plant Mucilage
Water