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Structural characteristics and anticancer activity of fucoidan from the brown alga Sargassum mcclurei.

ABSTRACT: Three different fucoidan fractions were isolated and purified from the brown alga, Sargassum mcclurei. The SmF1 and SmF2 fucoidans are sulfated heteropolysaccharides that contain fucose, galactose, mannose, xylose and glucose. The SmF3 fucoidan is highly sulfated (35%) galactofucan, and the main chain of the polysaccharide contains a ?3)-?-L-Fucp(2,4SO??)-(1?3)-?-L-Fucp(2,4SO??)-(1? motif with 1,4-linked 3-sulfated ?-L-Fucp inserts and 6-linked galactose on reducing end. Possible branching points include the 1,2,6- or 1,3,6-linked galactose and/or 1,3,4-linked fucose residues that could be glycosylated with terminal ?-D-Galp residues or chains of alternating sulfated 1,3-linked ?-L-Fucp and 1,4-linked ?-D-Galp residues, which have been identified in galactofucans for the first time. Both ?-L-Fucp and ?-D-Galp residues are sulfated at C-2 and/or C-4 (and some C-6 of ?-D-Galp) and potentially the C-3 of terminal ?-D-Galp, 1,4-linked ?-D-Galp and 1,4-linked ?-L-Fucp residues. All fucoidans fractions were less cytotoxic and displayed colony formation inhibition in colon cancer DLD-1 cells. Therefore, these fucoidan fractions are potential antitumor agents.

SUBMITTER: Thinh PD

PROVIDER: S-EPMC3707154 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Structural characteristics and anticancer activity of fucoidan from the brown alga Sargassum mcclurei.

Thinh Pham Duc PD Menshova Roza V RV Ermakova Svetlana P SP Anastyuk Stanislav D SD Ly Bui Minh BM Zvyagintseva Tatiana N TN

Marine drugs 20130506 5

Three different fucoidan fractions were isolated and purified from the brown alga, Sargassum mcclurei. The SmF1 and SmF2 fucoidans are sulfated heteropolysaccharides that contain fucose, galactose, mannose, xylose and glucose. The SmF3 fucoidan is highly sulfated (35%) galactofucan, and the main chain of the polysaccharide contains a →3)-α-L-Fucp(2,4SO₃⁻)-(1→3)-α-L-Fucp(2,4SO₃⁻)-(1→ motif with 1,4-linked 3-sulfated α-L-Fucp inserts and 6-linked galactose on reducing end. Possible branching point ...[more]

PMID: 23648551

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Project description:Sargassum serratifolium C. Agardh (Phaeophyceae, Fucales) is a marine brown alga that belongs to the family Sargassaceae. It is widely distributed throughout coastal areas of Korea and Japan. S. serratifolium has been found to contain high concentrations of plastoquinones, which have strong anti-cancer, anti-inflammatory, antioxidant, and neuroprotective activity. This study aims to investigate the anti-diabetic activity of S. serratifolium and its major constituents through inhibition of protein tyrosine phosphatase 1B (PTP1B), ?-glucosidase, and ONOO--mediated albumin nitration. S. serratifolium ethanolic extract and fractions exhibited broad PTP1B and ?-glucosidase inhibitory activity (IC50, 1.83~7.04 and 3.16~24.16 µg/mL for PTP1B and ?-glucosidase, respectively). In an attempt to identify bioactive compounds, three plastoquinones (sargahydroquinoic acid, sargachromenol and sargaquinoic acid) were isolated from the active n-hexane fraction of S. serratifolium. All three plastoquinones exhibited dose-dependent inhibitory activity against PTP1B in the IC50 range of 5.14-14.15 µM, while sargachromenol and sargaquinoic acid showed dose-dependent inhibitory activity against ?-glucosidase (IC50 42.41 ± 3.09 and 96.17 ± 3.48 µM, respectively). In the kinetic study of PTP1B enzyme inhibition, sargahydroquinoic acid and sargaquinoic acid led to mixed-type inhibition, whereas sargachromenol displayed noncompetitive-type inhibition. Moreover, plastoquinones dose-dependently inhibited ONOO--mediated albumin nitration. Docking simulations of these plastoquinones demonstrated negative binding energies and close proximity to residues in the binding pocket of PTP1B and ?-glucosidase, indicating that these plastoquinones have high affinity and tight binding capacity towards the active site of the enzymes. These results demonstrate that S. serratifolium and its major plastoquinones may have the potential as functional food ingredients for the prevention and treatment of type 2 diabetes.

Dataset Information

Structural characteristics and anticancer activity of fucoidan from the brown alga Sargassum mcclurei.

Publications

Structural characteristics and anticancer activity of fucoidan from the brown alga Sargassum mcclurei.

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