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Mar Drugs
2021 Mar 18;193:. doi: 10.3390/md19030162.
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Structural Characterization and Heparanase Inhibitory Activity of Fucosylated Glycosaminoglycan from Holothuria floridana.
Shi X
,
Guan R
,
Zhou L
,
Zuo Z
,
Tao X
,
Wang P
,
Zhou Y
,
Yin R
,
Zhao L
,
Gao N
,
Zhao J
.
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Unique fucosylated glycosaminoglycans (FG) have attracted increasing attention for various bioactivities. However, the precise structures of FGs usually vary in a species-specific manner. In this study, HfFG was isolated from Holothuria floridana and purified by anion exchange chromatography with the yield of ~0.9%. HfFG was composed of GlcA, GalNAc and Fuc, its molecular weight was 47.3 kDa, and the -OSO3-/-COO- molar ratio was 3.756. HfFG was depolymerized by a partial deacetylation-deaminative cleavage method to obtain the low-molecular-weight HfFG (dHfFG). Three oligosaccharide fragments (Fr-1, Fr-2, Fr-3) with different molecular weights were isolated from the dHfFG, and their structures were revealed by 1D and 2D NMR spectroscopy. HfFG should be composed of repeating trisaccharide units -{(L-FucS-α1,3-)d-GlcA-β1,3-d-GalNAc4S6S-β1,4-}-, in which sulfated fucose (FucS) includes Fuc2S4S, Fuc3S4S and Fuc4S residues linked to O-3 of GlcA in a ratio of 45:35:20. Furthermore, the heparanase inhibitory activities of native HfFG and oligosaccharide fragments (Fr-1, Fr-2, Fr-3) were evaluated. The native HfFG and its oligosaccharides exhibited heparanase inhibitory activities, and the activities increased with the increase of molecular weight. Additionally, structural characteristics such as sulfation patterns, the terminal structure of oligosaccharides and the presence of fucosyl branches may be important factors affecting heparanase inhibiting activity.
81703374 National Natural Science Foundation of China, 81773737 National Natural Science Foundation of China, 31600649 National Natural Science Foundation of China, 82073725 National Natural Science Foundation of China
Figure 1. Physicochemical properties of fucosylated glycosaminoglycans isolated from Holothuria floridana (HfFG), low-molecular-weight HfFG (dHfFG) and the purified fragments. HPLC profiles of HfFG and dHfFG (a) and the oligosaccharide fragments with various degrees of polymerization (dp) (d); chromatograms of 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of mixed monosaccharide standards and HfFG (b); and conductimetric titration curve of HfFG (c).
Figure 2. 1H NMR spectra of HfFG (a) and dHfFG (b).
Figure 3. 1H NMR spectra of Fr-1 (a), Fr-2 (b), Fr-3 (c) and 13C NMR spectrum of Fr-2 (d).
Figure 4. 1H-1H COSY (a), overlapped spectra (b) of 1H-1H COSY (gray), ROESY (green) and TOCSY (red), 1H-13C HSQC (c) and partial 1H-13C HMBC (d) spectra of Fr-2 and the chemical structure of native HfFG and its oligosaccharides (e). Fuc2S4S, Fuc3S4S and Fuc4S were signed as I, II, III, respectively, and U, A, T represent the GlcA, GalNAc and anTal residues, respectively.
Figure 5. Inhibition effects of HfFG and its oligosaccharides on heparanase (mean ± SD, n = 4).
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