Table 1.
Sulfated modification of natural plant polysaccharides (2012–2022).
| Source | Extraction Methods | B-Mw (kda) |
A-Mw (kda) |
Modification Method | Main Modifying Conditions | DS | B-CHO (%) | A-CHO (%) | Biological Activity | Refer |
|---|---|---|---|---|---|---|---|---|---|---|
| Alfalfa (AP) |
Hot-water extraction | 22 | 25 | Chloro-sulfonic acid pyridine method | AP (200 mg) N, N-dimethylformamide (20 mL) Ratio of chlorosulfonic acid to pyridine (1.5:1) Reaction at 55 °C for 2.25 h |
0.724 | 90.2 | 70.3 | Antioxidant, Antibacterial Antiobesity |
[21] |
| Opuntia ficus indica cladodes (PC) |
Ultrasonic-assisted extraction | 7.89 | 2.1–3.87 | Sulfur trioxide pyridine method | PC (400 mg) Formamide (16 mL) Ratio of chlorosulfonic acid to N, N-dimethylformamide (1:6) Reaction at 50 °C for 3 h |
0.12–0.46 | 54.2 | 21.44–52.72 | Anticoagulant | [22] |
| Amana edulis (AEPS) |
Acidic extraction Hot-water extraction |
N | N | Sulfuric acid method | AEPS (500 mg) Ratio of concentrated sulfuric acid to n-butanol (3:1) (NH4)2SO4 (125 mg) Reaction at 0 °C for 30 min |
1.256–2.134 | 56.53–65.61 | 56.48–63.41 | Antioxidant | [23] |
| Persimmon fruits (PFP) | Hot-water extraction | 130 | 48–53 | Chlorosulfonic acid pyridine method | PAS (500 mg) Formamide (20 mL) Ratio of chlorosulfonic acid to pyridine (1:8, 1:4, 1:2) Reaction at 50 °C for 2 h |
0.8–2.5 | N | N | Immunomodulatory | [25] |
| Longan (LP) | Hot-water extraction | 118 | 105 | Sulfuric acid method | LP (500 mg) Ratio of sulfuric acid to butanol complex (3:1) Ammonium sulfate (125 mg) Reaction at 10 °C for 3 h |
2.011 | N | N | Immunomodulatory Antitumor |
[26] |
| Dendrobium huoshanense (DHPD) | Hot-water extraction | 8.09 × 103 | 1.01–1.10 × 104 | Chlorosulfonic acid pyridine method | DHPD (500 mg) Formamide (5 mL) Ratio of chlorosulfonic acid to pyridine (1:2) Reaction at 60 °C for 30 min, 60 min |
0.475–0.94 | 92.89 | 37.7–56.35 | Antiglycation | [27] |
| Astragalus (APS) |
N | N | N | Chlorosulfonic acid pyridine method | APS (400 mg) Ratio of chlorosulfonic acid to pyridine (1:6) Reaction at 95 °C for 1 h |
1.4 | 97 | N | Immunomodulatory | [28] |
| Cyclina sinensis (CSPS-1) | Hot-water extraction | N | N | Chlorosulfonic acid pyridine method | ASP (100 mg) N, N-dimethylformamide (20 mL) Ratio of chlorosulfonic acid to pyridine (1:4) Reaction at 65 °C for 2 h |
0.3–1.02 | N | N | Antitumor | [29] |
| Lyciumbarbarum (LBPS) | N | 11.87–13.12 | 18.58–29.06 | Chlorosulfonic acid pyridine method | LBPS (400 mg) Ratio of chlorosulfonic acid to pyridine (1:8) Reaction at 80 °C for 2 h |
N | N | 35.37–63.21 | Immunomodulatory | [30] |
| Artemisia sphaerocephala (ASP) |
Microwave-assisted extraction | 73.48 | 18.06–32.72 | Chlorosulfonic acid pyridine method | ASP (500 mg) Formamide (20 mL) Ratio of chlorosulfonic acid to pyridine (2:1) Reaction at 60 °C for 3 h |
0.44–0.63 | 90.2 | N | Antitumor | [31,32] |
| Cyclocarya paliurus (CP) | Hot-water extraction | 1.16 × 103 | 0.97–1.07 × 103 | Chlorosulfonic acid pyridine method | CP (600 mg) Formamide (60 mL) Ratio of chlorosulfonic acid to pyridine (1:4, 1:8) Reaction at 60 °C for 4 h |
0.12–0.42 | N | 42.41–63.77 | Antioxidant Immunomodulatory |
[33] |
| Sphallerocarpus gracilis (SGP) | Hot-water extraction | 218 | 59 | Chlorosulfonic acid pyridine method | SGP (200 mg) Formamide (15 mL) Ratio of chlorosulfonic acid to pyridine (1.3:1) Reaction at 65 °C for 3.4 h |
0.99 | N | N | Antioxidant | [34] |
| Borojoa sorbilis cuter (BP) | Ultrahigh pressure extraction |
35.8 | N | Sulfur trioxide pyridine method | BP (100 mg) DMSO (5 mL) SO3⋅Pyr (400 mg) Reaction at 60 °C for 7 h |
1.18 | N | N | Antitumor | [35] |
| Cyclocarya paliurus (CP) | Hot-water extraction | 1.16 × 103 | 0.97–1.12 × 103 | Chlorosulfonic acid pyridine method | CP (600 mg) CSA to Pyr at Ratios of 1:1, 1:4, 1:6, and 1:8 N, N-dimethylformamide (60 mL) Reaction at 60 °C for 4 h |
0.12–0.55 | 60.62 | 35.87–49.71 | Antioxidant | [36] |
| Cyclocarya paliurus (CP) |
Hot-water extraction (pretreatment degreasing) | 139 | 212 | Chlorosulfonic acid pyridine method | CP (600 mg) Formamide (20 mL) Ratio of chlorosulfonic acid to pyridine (1:4) Reaction at 60 °C for 4 h |
0.42 | 63.77 | 42.41 | Anti-inflammatory Antioxidant |
[37] |
| Blackcurrant (BCP) |
Ultrasonic-assisted extraction | 17.6 × 103 | 17.6–18.5 × 103 | Aminosul-fonic acid method | BCP (100 mg) N, N-dimethylformamide (40 mL) 4-dimethylamino-pyridine (162.2 mg) Ratio of amino sulfonic acid to BCP (8:1 to 30:1) reaction at different temperatures (60–100 °C) for various periods (1–5 h) |
0.53–1.28 | 84.89 | N | Antioxidant Hypoglycemic activity |
[38] |
| Artemisia sphaerocephala (PAS) |
Microwave-assisted extraction | 139.8 | 103–760 | Chloro-sulfonic acid pyridine method | PAS (500 mg) Formamide (30 mL) Ratio of chlorosulfonic acid to pyridine (2:1) Reaction at 60 °C for 15 to 300 min |
0.63–0.86 | N | N | Antitumor | [39] |
| Pumpkin (N) | Hot-water extraction | 10.18 | 3.84–7.7 | Chlorosulfonic acid pyridine method | Polysaccharide (250 mg) Formamide (10 mL) Reaction at 60 °C for 3 h |
0.26–0.45 | 95.17 | 7.53–12.29 | Anticoagulant | [40] |
| Abelmoschus manihot (Linn.) Medicus (LAMP) | Hot-water extraction | N | 264.2–1044.2 | Aminosul-fonic acid method | Polysaccharide (40 mg) N, N-dimethylformamide (15 mL) Aminosul-fonic acid (40, 80, 120 mg) Reaction at 80 °C for 3 h |
0.25 | 99.76 | 52.1 | Immunomodulatory | [41] |
| Bupleurum chinense (BCP) | Hot-water extraction | 29 | 37.6–51.7 | Chlorosulfonic acid pyridine method | BP (200 mg) Ratio of chlorosulfonic acid to pyridine (1:4, 1:8) Reaction at 80 °C for 2 h |
0.38–0.61 | 97.5 | N | Antioxidant Antisenescence |
[42] |
| Polygonatum sibiricum (N) | Hot-water extraction | 132.6 | 82.1–117.0 | Sulfur trioxide pyridine method | Reaction at 80 °C for 1 h, 3 h, 6 h | 0.5–1.9 | 94 | 78.5–88 | Immunomodulatory | [43] |
| Lycium barbarum L. (LBP) |
Enzyme extraction | 80.00 | 131.78 | Chlorosulfonic acid pyridine method | LBP (100 mg) Formamide (5 mL) Ratio of chlorosulfonic acid to pyridine (3:1) Reaction at 60 °C for 3 h |
1.43 | N | N | Antiangiogenic | [44] |
| Cucumber (N) | Hot-water extraction | N | N | Chloro-sulfonic acid pyridine method | Polysaccharide (500 mg) N, N-dimethyl formamide (10 mL) Reaction at 80 °C for 3 h |
0.65 | 20.6 | 31.2 | Antioxidant | [45] |
| Pumpkin (N) | Hot-water extraction | N | N | Chloro-sulfonic acid pyridine method | polysaccharide (500 mg) N, N-dimethylformamide (30 mL) Ratio of chlorosulfonic acid to pyridine (2:5) Reaction at 100 °C for 1 h |
0.35 | 81 | 61.8 | Antioxidant | [46] |
| Chinese yam (CYP) | Enzyme-assisted hot-water extraction | 19.5 | 29.6 | Chloro-sulfonic acid pyridine method | Ratio of chlorosulfonic acid to pyridine (1:5) Reaction at 70 °C |
0.44 | 35.77 | 33.27 | Immunomodulatory | [47] |
| Jerusalem artichoke (JAP) | N | 2.6 | N | Sulfur trioxide pyridine method | JAP (200 mg) Pyridine (5 mL) SO3⋅Pyr (600 mg) Reaction at 95 °C for 4 h |
0.56 | N | N | Antitumor | [48] |
| Chinese yam (CYP) | Enzymatic-assisted extraction | 33.33 | 37.04 | Chloro-sulfonic acid pyridine method | CYP (400 mg) Formamide (100 mL) Ratio of chlorosulfonic acid to pyridine (1:3) Reaction at 70 °C for 3 h |
0.51 | 47.45 | 36.77 | Immunomodulatory | [49] |
| Cyclocarya paliurus (CPP, CPP0.05) | Hot-water extraction (pretreatment degreasing) | 35.8 30.1 |
12.64–52.62 | Chloro-sulfonic acid pyridine method | CPP, CPP0.05 (20 mg) Formamide (20 mL) Ratio of chlorosulfonic acid to pyridine (1:6) Reaction at 60 °C for 2 h |
0.18–0.32 | 62.75 | 50.14–54.42 | Immunomodulatory | [50] |
| Tamarind seed (TSP) | Hot-water extraction | 1370 | 1340 | Sulfur trioxide pyridine method | TSP (1 g) Reaction at 50 °C for 4 h |
0.31 | N | N | Osteogenic activities | [51] |
| Jujube (JP) | Hot-water extraction | 275 | 317 | Chloro-sulfonic acid pyridine method | JP (500 mg) Formamide (100 mL) Ratio of chlorosulfonic acid to pyridine (1:1) Reaction at 75 °C for 1 h |
0.664 | 75.4 | 63.40 | Antioxidant Antibacterial | [52] |
| Orchis chusua D. Don (SP) |
Hot-water extraction | 369 | 318 | Sulfur trioxide pyridine method | SP (200 mg) N, N-dimethylformamide (20 mL) SO3⋅Pyr (100 mg) Reaction at 80 °C for 3 h |
0.12 | 47.93 | 71.55 | Antioxidant Probiotic ability | [53] |
| Cyclocarya paliurus (CP) | Hot-water extraction | 139.6 | 161.5 | Chloro-sulfonic acid pyridine method | CP sample (400 mg) formamide (40 mL) Ratio of chlorosulfonic acid to pyridine (1:7) Reaction at 60 °C for 4 h |
0.17 | N | N | Antioxidant Antitumor |
[54] |
| Cardamine hupingshanensis (CHP) |
Hot-water extraction | N | 22.2 | Sulfur trioxide pyridine method | CHP (600 mg) DMSO (180 mL) SO3⋅Pyr (15 g) Reaction at 55 °C for 2 h |
N | N | N | Antioxidant | [55] |
N: not referred; B-Mw: Mw before modification; A-Mw: Mw after modification; B-CHO: carbohydrate content before modification; A-CHO: carbohydrate content after modification.