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Mar Drugs
2023 Feb 24;213:. doi: 10.3390/md21030148.
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Structural Elucidation of a Glucan from Trichaster palmiferus by Its Degraded Products and Preparation of Its Sulfated Derivative as an Anticoagulant.
Ma H
,
Yuan Q
,
Tang H
,
Tan H
,
Li T
,
Wei S
,
Huang J
,
Yao Y
,
Hu Y
,
Zhong S
,
Liu Y
,
Gao C
,
Zhao L
.
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Echinoderms have been attracting increasing attention for their polysaccharides, with unique chemical structure and enormous potential for preparing drugs to treat diseases. In this study, a glucan (TPG) was obtained from the brittle star Trichaster palmiferus. Its structure was elucidated by physicochemical analysis and by analyzing its low-molecular-weight products as degraded by mild acid hydrolysis. The TPG sulfate (TPGS) was prepared, and its anticoagulant activity was investigated for potential development of anticoagulants. Results showed that TPG consisted of a consecutive α1,4-linked D-glucopyranose (D-Glcp) backbone together with a α1,4-linked D-Glcp disaccharide side chain linked through C-1 to C-6 of the main chain. The TPGS was successfully prepared with a degree of sulfation of 1.57. Anticoagulant activity results showed that TPGS significantly prolonged activated partial thromboplastin time, thrombin time, and prothrombin time. Furthermore, TPGS obviously inhibited intrinsic tenase, with an EC50 value of 77.15 ng/mL, which was comparable with that of low-molecular-weight heparin (LMWH) (69.82 ng/mL). TPGS showed no AT-dependent anti-FIIa and anti-FXa activities. These results suggest that the sulfate group and sulfated disaccharide side chains play a crucial role in the anticoagulant activity of TPGS. These findings may provide some information for the development and utilization of brittle star resources.
2020GXNSFFA297005 Natural Science Foundation of Guangxi Zhuang Autonomous Region, AD21159002 Specific Research Project of Guangxi for Research Bases and Talents, 32160220 and 82160738 National Natural Science Foundation of China, 2021004 Development Program of High-level Talent Team under the Qihuang Project of Guangxi Univer-sity of Chinese Medicine, 05019055 Special Fund for Bagui Scholars of Guangxi, 2022A007 Guangxi University of Chinese Medicine "GuiPai Traditional Chinese Medicine inheritance and innovation team" Project
Figure 1. Physicochemical properties of TPG, TPGS, and fractions F1–F3. HPGPC profiles of TPG, TPGS (A), and fractions F1–F3 (D), chromatograms of PMP derivatives of mixed monosaccharide standards and TPG (B), and FT-IR spectra of TPG and TPGS (C).
Figure 2. 1H (A) and 13C (B) NMR spectra of TPG and fractions F1–F3.
Figure 3. 2D NMR spectra of F2 and F3 (A–D), and a proposed structure of F2 and F3 (E). (A,B) are TOCSY and HSQC spectra of F2, (C) is HSQC spectrum of F3, and (D) is the partial ROESY and HMBC spectra of F3. The signals labeled in red ellipses in (D) indicate the connection positions.
Figure 4. Superimposed 1H–13C HSQC spectra of TPG (black) and TPGS (red).
Figure 5. Effects of TPGS on APTT (A), PT (B), TT (C), intrinsic FXase (D), FXa (E), and FIIa (F) (n = 3).
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