title: Structure and biological activity of a fucosylated chondroitin sulfate from the sea cucumber Cucumaria japonica.
abstract: A fucosylated chondroitin sulfate (FCS) was isolated from the body wall of Pacific sea cucumber Cucumaria japonicaby extraction in the presence of papain followed by Cetavlon precipitation and anion-exchange chromatography. FCS was shown to contain D-GalNAc, D-GlcA, L-Fuc and sulfate in molar proportions of about 1:1:1:4.5. Structure of FCS was elucidated using NMR spectroscopy and methylation analysis of the native polysaccharide and products of its desulfation and carboxyl reduction. The polysaccharide was shown to contain a typical chondroitin core → 3)-β-D-GalNAc-(1 → 4)-β-D-GlcA-(1 →. Sulfate groups in this core occupy O-4 and the majority of O-6 of GalNAc. Fucosyl branches are represented by 3,4- and 2,4-disulfated units in a ratio of 4:1 and are linked to O-3 of GlcA. In addition, ∼ 33% of GlcA are 3-O-sulfated, and hence, the presence of short fucooligosaccharide chains side by side with monofucosyl branches cannot be excluded. FCS was shown to inhibit platelets aggregation in vitro mediated by collagen and ristocetin, but not adenosine diphosphate, and demonstrated significant anticoagulant activity, which is connected with its ability to enhance inhibition of thrombin and factor Xa by antithrombin III, as well as to influence von Willebrand factor activity. The latest property significantly distinguished FCS from low-molecular-weight heparin.
authors.affiliation: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia usov@ioc.ac.ru ustnad@gmail.com.
authors.forename: Nadezhda E
authors.initials: NE
authors.lastname: Ustyuzhanina
authors.affiliation: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia.
authors.forename: Maria I
authors.initials: MI
authors.lastname: Bilan
authors.affiliation: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia.
authors.forename: Andrey S
authors.initials: AS
authors.lastname: Dmitrenok
authors.affiliation: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Shashkov
authors.affiliation: Far Eastern Branch of the Russian Academy of Sciences, G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Prospect 100 let Vladivostoku 159, Vladivostok 690022, Russia.
authors.forename: Mikhail I
authors.initials: MI
authors.lastname: Kusaykin
authors.affiliation: Far Eastern Branch of the Russian Academy of Sciences, G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Prospect 100 let Vladivostoku 159, Vladivostok 690022, Russia.
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
authors.affiliation: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia.
authors.forename: Nikolay E
authors.initials: NE
authors.lastname: Nifantiev
authors.affiliation: Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russia usov@ioc.ac.ru ustnad@gmail.com.
authors.forename: Anatolii I
authors.initials: AI
authors.lastname: Usov
mesh_terms: D000818:Animals; D001792:Blood Platelets / Q000378:metabolism*; D002236:Carbohydrate Conformation; D002809:Chondroitin Sulfates / Q000737:chemistry / Q000494:pharmacology; D048016:Cucumaria / Q000737:chemistry*; D005643:Fucose / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D010974:Platelet Aggregation / Q000187:drug effects*
chemical_list: D005643:Fucose; D002809:Chondroitin Sulfates
keywords: Cucumaria japonica; anticoagulant activity; antithrombotic activity; fucosylated chondroitin sulfate; sea cucumber