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Mar Drugs
2022 Jun 03;206:. doi: 10.3390/md20060377.
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A Fucan Sulfate with Pentasaccharide Repeating Units from the Sea Cucumber Holothuriafloridana and Its Anticoagulant Activity.
Ning Z
,
Wang P
,
Zuo Z
,
Tao X
,
Gao L
,
Xu C
,
Wang Z
,
Wu B
,
Gao N
,
Zhao J
.
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A fucan sulfate (HfFS) was isolated from the sea cucumber Holothuriafloridana after proteolysis-alkaline treatment and purified with anion-exchange chromatography. The molecular weight (Mw) of HfFS was determined to be 443.4 kDa, and the sulfate content of HfFS was 30.4%. The structural analysis of the peroxidative depolymerized product (dHfFS-1) showed that the primary structure of HfFS was mainly composed of a distinct pentasaccharide repeating unit -[l-Fuc2S4S-α(1,3)-l-Fuc-α(1,3)-Fuc-α(1,3)-l-Fuc2S-α(1,3)-l-Fuc2S-α(1,3)-]n-. Then, the "bottom-up" strategy was employed to confirm the structure of HfFS, and a series of fucooligosaccharides (disaccharides, trisaccharides, and tetrasaccharides) were purified from the mild acid-hydrolyzed HfFS. The structures identified through 1D/2D NMR spectra showed that these fucooligosaccharides could be derivates from the pentasaccharide units, while the irregular sulfate substituent also exists in the units. Anticoagulant activity assays of native HfFS and its depolymerized products (dHf-1~dHf-6) in vitro suggested that HfFS exhibits potent APTT-prolonging activity and the potencies decreased with the reduction in molecular weights, and HfFS fragments (dHf-4~dHf-6) with Mw less than 11.5 kDa showed no significant anticoagulant effect. Overall, our study enriched the knowledge about the structural diversity of FSs in different sea cucumber species and their biological activities.
Scheme 1. Typical repeating units of FSs found in sea cucumbers (A) and the structures of fucooligosaccharides in this study (B).
Figure 1. HPGPC of crude polysaccharide, native HfFS, and dHfFS-1 (A), HPLC profiles of PMP derivatives of mixed monosaccharide standards and HfFS (B), sulfate elution profiles of HfFS obtained using ion chromatography (C), and IR spectrum of HfFS (D).
Figure 2. 1H NMR spectra (A) of HfFS and its low-molecular-weight product (dHfFS-1), overlapped spectra (B) of 1H-1H COSY (gray), TOCSY (red) and ROESY (green), 13C NMR spectrum (C) of dHfFS-1 and 1H-13C HSQC spectrum (D).
Figure 3. Kinetics of the mild acid hydrolysis of HfFS.
Figure 4. HPGPC profiles of dHfFS-2 (A) and five size-homogeneous fractions (F1, F2, F3, F4, F5) (B).
Figure 5. 1D/2D NMR spectra of F2. (A), 1H NMR of F2. (B), 13C NMR of F2. (C), overlapped spectra of 1H-13C HSQC (gray) and HMBC (red) of F2.
Figure 6. 1D/2D NMR spectra of F3-a and F3-b. (A), 1H NMR spectrum of F3-a. (B), 13C NMR spectrum of F3-a. (C), part of the overlapped spectra of 1H-1H COSY (gray), TOCSY (red), and ROESY (green) of F3-a. (D), 1H NMR spectrum of F3-b. (E), 13C NMR spectrum of F3-b. (F), overlapped spectra of 1H-13C HSQC (gray) and HMBC (red) of F3-b.
Figure 7. 1D/2D NMR spectra of F4 and F5. (A), 1H NMR spectrum of F4. (B), 1H NMR spectrum of F5. (C), 13C NMR spectrum of F4. (D), 13C NMR spectrum of F5. (E), overlapped spectra of 1H-13C HSQC (gray) and HMBC (red) of F4.
Figure 8. 1H NMR spectra (A) and HPGPC (B) of dHf-1~dHf-6 and the effects of HfFS and its low-molecular-weight derivatives (dHf-1~dHf-3) on APTT (C).
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