Zheng W et al. (2019), Physicochemical Characteristics and Anticoagula...

ECB-ART-47081

Mar Drugs 2019 Mar 29;174:. doi: 10.3390/md17040198.

Show Gene links Show Anatomy links

Physicochemical Characteristics and Anticoagulant Activities of the Polysaccharides from Sea Cucumber Pattalus mollis.

Zheng W , Zhou L , Lin L , Cai Y , Sun H , Zhao L , Gao N , Yin R , Zhao J .

Abstract
Sulfated polysaccharides from sea cucumbers possess distinct chemical structure and various biological activities. Herein, three types of polysaccharides were isolated and purified from Pattalus mollis, and their structures and bioactivities were analyzed. The fucosylated glycosaminoglycan (PmFG) had a CS-like backbone composed of the repeating units of {-4-d-GlcA-β-1,3-d-GalNAc4S6S-β-1-}, and branches of a sulfated α-l-Fuc (including Fuc2S4S, Fuc3S4S and Fuc4S with a molar ratio of 2:2.5:1) linked to O-3 of each d-GlcA. The fucan sulfate (PmFS) had a backbone consisting of a repetitively linked unit {-4-l-Fuc2S-α-1-}, and interestingly, every trisaccharide unit in its backbone was branched with a sulfated α-l-Fuc (Fuc4S or Fuc3S with a molar ratio of 4:1). Apart from the sulfated polysaccharides, two neutral glycans (PmNG-1 & -2) differing in molecular weight were also obtained and their structures were similar to animal glycogen. Anticoagulant assays indicated that PmFG and PmFS possessed strong APTT prolonging and intrinsic factor Xase inhibition activities, and the sulfated α-l-Fuc branches might contribute to the anticoagulant and anti-FXase activities of both PmFG and PmFS.

PubMed ID: 30934819
PMC ID: PMC6521006
Article link: Mar Drugs
Grant support: [+]

Genes referenced: LOC100887844 LOC592256

Article Images: [+] show captions

References [+] :

Berteau, Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide. 2003, Pubmed

Berteau, Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide. 2003, Pubmed
Bordbar, High-value components and bioactives from sea cucumbers for functional foods--a review. 2011, Pubmed , Echinobase
Borsig, Selectin blocking activity of a fucosylated chondroitin sulfate glycosaminoglycan from sea cucumber. Effect on tumor metastasis and neutrophil recruitment. 2007, Pubmed , Echinobase
Cai, An anticoagulant fucan sulfate with hexasaccharide repeating units from the sea cucumber Holothuria albiventer. 2018, Pubmed , Echinobase
Chevolot, A disaccharide repeat unit is the major structure in fucoidans from two species of brown algae. 2001, Pubmed
Holtkamp, Fucoidans and fucoidanases--focus on techniques for molecular structure elucidation and modification of marine polysaccharides. 2009, Pubmed
Huang, The depolymerized fucosylated chondroitin sulfate from sea cucumber potently inhibits HIV replication via interfering with virus entry. 2013, Pubmed , Echinobase
Kariya, Occurrence of chondroitin sulfate E in glycosaminoglycan isolated from the body wall of sea cucumber Stichopus japonicus. 1990, Pubmed , Echinobase
Kariya, Structure of fucose branches in the glycosaminoglycan from the body wall of the sea cucumber Stichopus japonicus. 1997, Pubmed , Echinobase
Kariya, Isolation and partial characterization of fucan sulfates from the body wall of sea cucumber Stichopus japonicus and their ability to inhibit osteoclastogenesis. 2004, Pubmed , Echinobase
Katzman, Acid polysaccharides from invertebrate connective tissue: phylogenetic aspects. 1969, Pubmed
Li, Structural Elucidation and Biological Activity of a Highly Regular Fucosylated Glycosaminoglycan from the Edible Sea Cucumber Stichopus herrmanni. 2017, Pubmed , Echinobase
Liu, Structural analysis and biological activity of a highly regular glycosaminoglycan from Achatina fulica. 2018, Pubmed
Luo, Comparison of physicochemical characteristics and anticoagulant activities of polysaccharides from three sea cucumbers. 2013, Pubmed , Echinobase
Mourão, Highly acidic glycans from sea cucumbers. Isolation and fractionation of fucose-rich sulfated polysaccharides from the body wall of Ludwigothurea grisea. 1987, Pubmed , Echinobase
Pereira, Structure and anticoagulant activity of sulfated fucans. Comparison between the regular, repetitive, and linear fucans from echinoderms with the more heterogeneous and branched polymers from brown algae. 1999, Pubmed , Echinobase
Pomin, Structure, biology, evolution, and medical importance of sulfated fucans and galactans. 2008, Pubmed , Echinobase
Pomin, Review: an overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures. 2009, Pubmed , Echinobase
Pomin, Holothurian fucosylated chondroitin sulfate. 2014, Pubmed , Echinobase
Pomin, Sulfated glycans in inflammation. 2015, Pubmed
Shang, Precise structures of fucosylated glycosaminoglycan and its oligosaccharides as novel intrinsic factor Xase inhibitors. 2018, Pubmed
Shang, Structural analysis and anticoagulant activities of three highly regular fucan sulfates as novel intrinsic factor Xase inhibitors. 2018, Pubmed , Echinobase
Vieira, Extensive heterogeneity of proteoglycans bearing fucose-branched chondroitin sulfate extracted from the connective tissue of sea cucumber. 1993, Pubmed , Echinobase
Vieira, Structure of a fucose-branched chondroitin sulfate from sea cucumber. Evidence for the presence of 3-O-sulfo-beta-D-glucuronosyl residues. 1991, Pubmed , Echinobase
Wu, Anticoagulant and antithrombotic evaluation of native fucosylated chondroitin sulfates and their derivatives as selective inhibitors of intrinsic factor Xase. 2015, Pubmed
Wu, Structural analysis and anticoagulant activities of the novel sulfated fucan possessing a regular well-defined repeating unit from sea cucumber. 2015, Pubmed , Echinobase
Wu, Structure and effect of sulfated fucose branches on anticoagulant activity of the fucosylated chondroitin sulfate from sea cucumber Thelenata ananas. 2012, Pubmed , Echinobase
Yang, Structural analysis and anticoagulant activities of two sulfated polysaccharides from the sea cucumber Holothuria coluber. 2018, Pubmed , Echinobase
Yang, Novel branch patterns and anticoagulant activity of glycosaminoglycan from sea cucumber Apostichopus japonicus. 2015, Pubmed , Echinobase
Yin, Oligosaccharides from depolymerized fucosylated glycosaminoglycan: Structures and minimum size for intrinsic factor Xase complex inhibition. 2018, Pubmed , Echinobase
Yu, Structural study of fucoidan from sea cucumber Acaudina molpadioides: a fucoidan containing novel tetrafucose repeating unit. 2014, Pubmed , Echinobase
Zhao, Discovery of an intrinsic tenase complex inhibitor: Pure nonasaccharide from fucosylated glycosaminoglycan. 2015, Pubmed

	Figure 1. HPGPC profiles of Fraction-1, PmNG-1, PmNG-2 and PmFG (A); Fraction-2 and PmFS (B). The samples were analyzed on an Agilent Technologies 1200 series equipped with a Shodex OH-pak SB-804 HQ column and eluted with 0.1 M NaCl solution at a flow rate of 0.5 mL/min.
	Figure 2. HPLC profiles of monosaccharide-PMP derivates of PmFG (a), PmFS (b), PmNG-2 (c), PmNG-1 (d) and standard monosaccharides (e).
	Figure 3. Conductimetric titration curves of PmFG (A) and PmFS (B).
	Figure 4. FT-IR spectra of PmNG-1 (a), PmNG-2 (b), PmFS (c) and PmFG (d).
	Figure 5. 1H (A,B) and 13C (C) NMR spectra of PmFG (A) and dPmFG-II (B,C) and signal assignments. I, Fuc2S4S; II, Fuc3S4S; III, Fuc4S; U, GlcA; A, GalNAc.
	Figure 6. 1H-1H COSY (A), 1H-13C HSQC (B)/HMBC (C), and superimposed 1H-1H TOCSY (red)/ROESY (green) (D) and signal assignments (purple: the correlation signals of glycosidic bonds). I, Fuc2S4S; II, Fuc3S4S; III, Fuc4S; U, GlcA; A, GalNAc.
	Figure 7. 1H (A) and 13C (B) NMR spectra of PmFS and signal assignments.
	Figure 8. Superimposed 1H-1H COSY (gray) -TOCSY (red) -ROESY (green) (A), 1H-13C HSQC (B) and 1H-13C HMBC (C) spectra of PmFS.
	Figure 9. Proposed chemical structures of PmFG (A) and PmFS (B).