Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments
<i>Apostichopus japonicus</i> is one of the most economically important species in sea cucumber aquaculture in China. Fucosylated glycosaminoglycan from <i>A. japonicus</i> (AjFG) has shown multiple pharmacological activities. However, results from studies on the structure of...
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MDPI AG
2019-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/17/4/195 |
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| author | Ruowei Guan Yuan Peng Lutan Zhou Wenqi Zheng Xixi Liu Pin Wang Qingxia Yuan Na Gao Longyan Zhao Jinhua Zhao |
| author_facet | Ruowei Guan Yuan Peng Lutan Zhou Wenqi Zheng Xixi Liu Pin Wang Qingxia Yuan Na Gao Longyan Zhao Jinhua Zhao |
| author_sort | Ruowei Guan |
| collection | DOAJ |
| description | <i>Apostichopus japonicus</i> is one of the most economically important species in sea cucumber aquaculture in China. Fucosylated glycosaminoglycan from <i>A. japonicus</i> (AjFG) has shown multiple pharmacological activities. However, results from studies on the structure of AjFG are still controversial. In this study, the deaminative depolymerization method that is glycosidic bond-selective was used to prepare the depolymerized products from AjFG (dAjFG), and then a series of purified oligosaccharide fragments such as tri-, hexa-, nona-, and dodecasaccharides were obtained from dAjFG by gel permeation chromatography. The 1D/2D NMR and ESI-MS spectrometry analyses showed that these oligosaccharides had the structural formula of <span style="font-variant: small-caps;">l</span>-FucS-α1,3-<span style="font-variant: small-caps;">d</span>-GlcA-β1,3-{<span style="font-variant: small-caps;">d</span>-GalNAc<sub>4S6S</sub>-β1,4-[<span style="font-variant: small-caps;">l</span>-FucS-α1,3-]<span style="font-variant: small-caps;">d</span>-GlcA-β1,3-}<i><sub>n</sub></i>-<span style="font-variant: small-caps;">d</span>-anTal-diol<sub>4S6S</sub> (<i>n</i> = 0, 1, 2, 3; FucS represents Fuc<sub>2S4S</sub>, Fuc<sub>3S4S</sub>, or Fuc<sub>4S</sub>). Thus, the unambiguous structure of native AjFG can be rationally deduced: it had the backbone of {-4-<span style="font-variant: small-caps;">d</span>-GlcA-β1,3-<span style="font-variant: small-caps;">d</span>-GalNAc<sub>4S6S</sub>-β1-}<i><sub>n</sub></i>, which is similar to chondroitin sulfate E, and each <span style="font-variant: small-caps;">d</span>-GlcA residue in the backbone was branched with a <span style="font-variant: small-caps;">l</span>-FucS monosaccharide at <i>O</i>-3. Bioactivity assays confirmed that dAjFG and nonasaccharides and dodecasaccharides from AjFG had potent anticoagulant activity by intrinsic FXase inhibition while avoiding side effects such as FXII activation and platelet aggregation. |
| first_indexed | 2024-04-11T13:47:16Z |
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| language | English |
| last_indexed | 2024-04-11T13:47:16Z |
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| series | Marine Drugs |
| spelling | doaj.art-60cde440728b4ab0a331619126fe35452022-12-22T04:21:00ZengMDPI AGMarine Drugs1660-33972019-03-0117419510.3390/md17040195md17040195Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized FragmentsRuowei Guan0Yuan Peng1Lutan Zhou2Wenqi Zheng3Xixi Liu4Pin Wang5Qingxia Yuan6Na Gao7Longyan Zhao8Jinhua Zhao9School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China<i>Apostichopus japonicus</i> is one of the most economically important species in sea cucumber aquaculture in China. Fucosylated glycosaminoglycan from <i>A. japonicus</i> (AjFG) has shown multiple pharmacological activities. However, results from studies on the structure of AjFG are still controversial. In this study, the deaminative depolymerization method that is glycosidic bond-selective was used to prepare the depolymerized products from AjFG (dAjFG), and then a series of purified oligosaccharide fragments such as tri-, hexa-, nona-, and dodecasaccharides were obtained from dAjFG by gel permeation chromatography. The 1D/2D NMR and ESI-MS spectrometry analyses showed that these oligosaccharides had the structural formula of <span style="font-variant: small-caps;">l</span>-FucS-α1,3-<span style="font-variant: small-caps;">d</span>-GlcA-β1,3-{<span style="font-variant: small-caps;">d</span>-GalNAc<sub>4S6S</sub>-β1,4-[<span style="font-variant: small-caps;">l</span>-FucS-α1,3-]<span style="font-variant: small-caps;">d</span>-GlcA-β1,3-}<i><sub>n</sub></i>-<span style="font-variant: small-caps;">d</span>-anTal-diol<sub>4S6S</sub> (<i>n</i> = 0, 1, 2, 3; FucS represents Fuc<sub>2S4S</sub>, Fuc<sub>3S4S</sub>, or Fuc<sub>4S</sub>). Thus, the unambiguous structure of native AjFG can be rationally deduced: it had the backbone of {-4-<span style="font-variant: small-caps;">d</span>-GlcA-β1,3-<span style="font-variant: small-caps;">d</span>-GalNAc<sub>4S6S</sub>-β1-}<i><sub>n</sub></i>, which is similar to chondroitin sulfate E, and each <span style="font-variant: small-caps;">d</span>-GlcA residue in the backbone was branched with a <span style="font-variant: small-caps;">l</span>-FucS monosaccharide at <i>O</i>-3. Bioactivity assays confirmed that dAjFG and nonasaccharides and dodecasaccharides from AjFG had potent anticoagulant activity by intrinsic FXase inhibition while avoiding side effects such as FXII activation and platelet aggregation.https://www.mdpi.com/1660-3397/17/4/195<i>Apostichopus japonicus</i>fucosylated glycosaminoglycanoligosaccharideunambiguous structureanti-Fxase |
| spellingShingle | Ruowei Guan Yuan Peng Lutan Zhou Wenqi Zheng Xixi Liu Pin Wang Qingxia Yuan Na Gao Longyan Zhao Jinhua Zhao Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments Marine Drugs <i>Apostichopus japonicus</i> fucosylated glycosaminoglycan oligosaccharide unambiguous structure anti-Fxase |
| title | Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments |
| title_full | Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments |
| title_fullStr | Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments |
| title_full_unstemmed | Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments |
| title_short | Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from <i>Apostichopus japonicus</i>: Analysis of Its Depolymerized Fragments |
| title_sort | precise structure and anticoagulant activity of fucosylated glycosaminoglycan from i apostichopus japonicus i analysis of its depolymerized fragments |
| topic | <i>Apostichopus japonicus</i> fucosylated glycosaminoglycan oligosaccharide unambiguous structure anti-Fxase |
| url | https://www.mdpi.com/1660-3397/17/4/195 |
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