Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity
Fucosylated chondroitin sulfates (FCSs) <b>PC</b> and <b>HH</b> were isolated from the sea cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>, respectively. The purification of the polysaccharides was carried out by anion-exchange chrom...
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MDPI AG
2020-10-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/11/540 |
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| author | Nadezhda E. Ustyuzhanina Maria I. Bilan Andrey S. Dmitrenok Alexandra S. Silchenko Boris B. Grebnev Valentin A. Stonik Nikolay E. Nifantiev Anatolii I. Usov |
| author_facet | Nadezhda E. Ustyuzhanina Maria I. Bilan Andrey S. Dmitrenok Alexandra S. Silchenko Boris B. Grebnev Valentin A. Stonik Nikolay E. Nifantiev Anatolii I. Usov |
| author_sort | Nadezhda E. Ustyuzhanina |
| collection | DOAJ |
| description | Fucosylated chondroitin sulfates (FCSs) <b>PC</b> and <b>HH</b> were isolated from the sea cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>, respectively. The purification of the polysaccharides was carried out by anion-exchange chromatography on a DEAE-Sephacel column. The structural characterization of the polysaccharides was performed in terms of monosaccharide and sulfate content, as well as using a series of nondestructive NMR spectroscopic methods. Both polysaccharides were shown to contain a chondroitin core [→3)-β-<span style="font-variant: small-caps;">d</span>-GalNAc (N-acethyl galactosamine)-(1→4)-β-<span style="font-variant: small-caps;">d</span>-GlcA (glucuronic acid)-(1→]<sub>n</sub>, bearing sulfated fucosyl branches at O-3 of every GlcA residue in the chain. These fucosyl residues were different in their pattern of sulfation: <b>PC</b> contained Fuc2<i>S</i>4<i>S</i> and Fuc4<i>S</i> in a ratio of 2:1, whereas <b>HH</b> included Fuc2<i>S</i>4<i>S</i>, Fuc3<i>S</i>4<i>S</i>, and Fuc4<i>S</i> in a ratio of 1.5:1:1. Moreover, some GalNAc residues in <b>HH</b> were found to contain an unusual disaccharide branch Fuc4<i>S</i>-(1→2)-Fuc3<i>S</i>4<i>S</i>-(1→ at O-6. Sulfated GalNAc4<i>S</i>6<i>S</i> and GalNAc4<i>S</i> units were found in a ratio of 3:2 in <b>PC</b> and 2:1 in <b>HH</b>. Both polysaccharides demonstrated significant anticoagulant activity in a clotting time assay, which is connected with the ability of these FCSs to potentiate the inhibition of thrombin and factor Xa in the presence of anti-thrombin III (ATIII) and with the direct inhibition of thrombin in the absence of any cofactors. |
| first_indexed | 2024-03-10T15:15:41Z |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T15:15:41Z |
| publishDate | 2020-10-01 |
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| spelling | doaj.art-42bf2ec7bde6429d8da4421e83de2c6b2023-11-20T18:55:42ZengMDPI AGMarine Drugs1660-33972020-10-01181154010.3390/md18110540Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant ActivityNadezhda E. Ustyuzhanina0Maria I. Bilan1Andrey S. Dmitrenok2Alexandra S. Silchenko3Boris B. Grebnev4Valentin A. Stonik5Nikolay E. Nifantiev6Anatolii I. Usov7N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaFucosylated chondroitin sulfates (FCSs) <b>PC</b> and <b>HH</b> were isolated from the sea cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>, respectively. The purification of the polysaccharides was carried out by anion-exchange chromatography on a DEAE-Sephacel column. The structural characterization of the polysaccharides was performed in terms of monosaccharide and sulfate content, as well as using a series of nondestructive NMR spectroscopic methods. Both polysaccharides were shown to contain a chondroitin core [→3)-β-<span style="font-variant: small-caps;">d</span>-GalNAc (N-acethyl galactosamine)-(1→4)-β-<span style="font-variant: small-caps;">d</span>-GlcA (glucuronic acid)-(1→]<sub>n</sub>, bearing sulfated fucosyl branches at O-3 of every GlcA residue in the chain. These fucosyl residues were different in their pattern of sulfation: <b>PC</b> contained Fuc2<i>S</i>4<i>S</i> and Fuc4<i>S</i> in a ratio of 2:1, whereas <b>HH</b> included Fuc2<i>S</i>4<i>S</i>, Fuc3<i>S</i>4<i>S</i>, and Fuc4<i>S</i> in a ratio of 1.5:1:1. Moreover, some GalNAc residues in <b>HH</b> were found to contain an unusual disaccharide branch Fuc4<i>S</i>-(1→2)-Fuc3<i>S</i>4<i>S</i>-(1→ at O-6. Sulfated GalNAc4<i>S</i>6<i>S</i> and GalNAc4<i>S</i> units were found in a ratio of 3:2 in <b>PC</b> and 2:1 in <b>HH</b>. Both polysaccharides demonstrated significant anticoagulant activity in a clotting time assay, which is connected with the ability of these FCSs to potentiate the inhibition of thrombin and factor Xa in the presence of anti-thrombin III (ATIII) and with the direct inhibition of thrombin in the absence of any cofactors.https://www.mdpi.com/1660-3397/18/11/540sea cucumber<i>Holothuria hilla</i><i>Paracaudina chilensis</i>fucosylated chondroitin sulfateanticoagulant activity |
| spellingShingle | Nadezhda E. Ustyuzhanina Maria I. Bilan Andrey S. Dmitrenok Alexandra S. Silchenko Boris B. Grebnev Valentin A. Stonik Nikolay E. Nifantiev Anatolii I. Usov Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity Marine Drugs sea cucumber <i>Holothuria hilla</i> <i>Paracaudina chilensis</i> fucosylated chondroitin sulfate anticoagulant activity |
| title | Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity |
| title_full | Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity |
| title_fullStr | Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity |
| title_full_unstemmed | Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity |
| title_short | Fucosylated Chondroitin Sulfates from the Sea Cucumbers <i>Paracaudina chilensis</i> and <i>Holothuria hilla</i>: Structures and Anticoagulant Activity |
| title_sort | fucosylated chondroitin sulfates from the sea cucumbers i paracaudina chilensis i and i holothuria hilla i structures and anticoagulant activity |
| topic | sea cucumber <i>Holothuria hilla</i> <i>Paracaudina chilensis</i> fucosylated chondroitin sulfate anticoagulant activity |
| url | https://www.mdpi.com/1660-3397/18/11/540 |
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