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Purification and sequence characterization of chondroitin sulfate and dermatan sulfate from fishes

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Abstract

Chondroitin sulfate (CS) and dermatan sulfate (DS) were extracted and purified from skins or bones of salmon (Salmo salar), snakehead (Channa argus), monkfish (Lophius litulon) and skipjack tuna (Katsuwonus pelamis). Size, structural sequences and sulfate groups of oligosaccharides in the purified CS and DS could be characterized and identified using high performance liquid chromatography (HPLC) combined with Orbitrap mass spectrometry. CS and DS chain structure varies depending on origin, but motif structure appears consistent. Structures of CS and DS oligosaccharides with different size and sulfate groups were compared between fishes and other animals, and results showed that some minor differences of special structures could be identified by hydrophilic interaction chromatography-liquid chromatography-fourier transform-mass/mass spectrometry (HILIC-LC-FT-MS/MS). For example, data showed that salmon and skipjack CS had a higher percentage content of high-level sulfated oligosaccharides than that porcine CS. In addition, structural information of different origins of CS and DS was analyzed by principal component analysis (PCA) and results showed that CS and DS samples could be differentiated according to their molecular conformation and oligosaccharide fragments information. Understanding CS and DS structure derived from different origins may lead to the production of CS or DS with unique disaccharides or oligosaccharides sequence composition and biological functions.

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Abbreviations

CS:

chondroitin sulfate

DS:

dermatan sulfate

GAG:

glycosaminoglycan

PGs:

proteoglycans

LMWH:

low molecular weight heparin

MW:

molecular weight

AMAC:

2-Aminoacridone

PAGE:

polyacrylamide gel electrophoresis

DAD:

diode array detector

RP-HPLC:

reversed phase-high performance liquid chromatography

HILIC-LC-FT-MS/MS:

hydrophilic interaction chromatography-liquid chromatography-fourier transform-mass/mass spectrometry

PCA:

principal component analysis

RI:

refractive index

dp:

degree of polymerization

RE:

reducing end

HexA:

hexuronic acid

GalNAc:

2-acetamido-2-deoxy-β-D-galactose

GalNAcS:

GalNAc-SO3

GlcA:

D-glucuronic acid

HexAS:

HexA-SO3

dHexA:

unsaturated hexuronic acid

TIC:

total ion current

EICs:

Extracted ion chromatograms

SO3 :

sulfate ester

ΔDi-0S:

2-amido-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-D-galactose

ΔDi-4S:

2-acetamido-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose

ΔDi-6S:

2-acetamido-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-6-O-sulfo-D-galactose

ΔDi-2,4diS:

2-acetamido-2-deoxy-3-O-(2-O-sulfo-β-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose

ΔDi-2,6diS:

2-acetamido-2-deoxy-3-O-(2-O-sulfo-β-D-gluco-4-enepyranosyluronic acid)-6-O-sulfo-D-galactose

ΔDi-4,6diS:

2-acetamido-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-4,6-O-disulfo-D-galactose

Gal:

galactose

Xyl:

xylose

EIC:

extracted ion chromatogram.

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Acknowledgements

This work has been supported by Y17C200016 project of Zhejiang natural science foundation. We thank Dr. Xu for providing us with the help of Statistical analysis.

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  1. School of Food Science and Biological Engineering, Zhejiang Gongshang University, Hangzhou, Zhejiang Province, 310035, People’s Republic of China

    Na Lin, Xiaoli Mo, Yang Yang & Hong Zhang

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  1. Na Lin
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  2. Xiaoli Mo
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  3. Yang Yang
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Correspondence to Hong Zhang.

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Lin, N., Mo, X., Yang, Y. et al. Purification and sequence characterization of chondroitin sulfate and dermatan sulfate from fishes. Glycoconj J 34, 241–253 (2017). https://doi.org/10.1007/s10719-016-9759-y

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