Download PDF
Planta Med 2023; 89(15): 1457-1467
DOI: 10.1055/a-2148-7163
Biological and Pharmacological Activity
Original Papers

Structural Characterization and Anticomplement Activity of an Acidic Heteropolysaccharide from Lysimachia christinae Hance

Zhou Hong
1   State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, China
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
,
Li-Shuang Zhou
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
,
Zhi-Zhi Zhao 
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
,
Guo-Qi Yuan
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
,
Xiao-Jiang Wang
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
,
Yan Lu
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
,
Dao-Feng Chen
1   State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, China
2   School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, China
› Author AffiliationsThis work was supported by grants from the National Natural Science Foundation of China (No 81872977), National Key R&D Program of China (No 2019YFC1711000), and Development Project of Shanghai Peak Disciplines-Integrative Medicine (No 20180101).
› Further Information
Also available at
    Permissions and Reprints

Abstract

A novel acidic heteropolysaccharide (LCP-90-1) was isolated and purified from a traditional “heat-clearing” Chinese medicine, Lysimachia christinae Hance. LCP-90-1 (Mw, 20.65 kDa) was composed of Man, Rha, GlcA, Glc, Gal, and Ara, with relative molar ratios of 1.00: 3.00: 11.62: 1.31: 1.64: 5.24. The backbone consisted of 1,4-α-D-GlcpA, 1,4-α-D-Glcp, 1,4-β-L-Rhap, and 1,3,5-α-L-Araf, with three branches of β-D-Galp-(1 → 4)-β-L-Rhap-(1→, α-L-Araf-(1→ and α-D-Manp-(1→ attached to the C-5 position of 1,3,5-α-L-Araf. LCP-90-1 exhibited potent anticomplement activity (CH50: 135.01 ± 0.68 µg/mL) in vitro, which was significantly enhanced with increased glucuronic acid (GlcA) content in its degradation production (LCP-90-1-A, CH50: 28.26 ± 0.39 µg/mL). However, both LCP-90-1 and LCP90-1-A were inactivated after reduction or complete acid hydrolysis. These observations indicated the important role of GlcA in LCP-90-1 and associated derivatives with respect to anticomplement activity. Similarly, compared with LCP-90-1, the antioxidant activity of LCP-90-1-A was also enhanced. Thus, polysaccharides with a high content of GlcA might be important and effective substances of L. christinae.

Key words

Primulaceae - Lysimachia christinae - Polysaccharide - structural characterization - anticomplement

Supporting Information

    Detailed procedures, other main reagents used for the experiment, HPLC chromatograms of absolute configurations, FT-IR spectrum of methylated products of LCP-90-1, mass spectra of PMAAs, and the HPGPC-ELSD chromatogram of LCP-90-1-A are available as Supporting Information.

  • Supporting Information


Publication History

Received: 27 April 2023

Accepted after revision: 04 August 2023

Accepted Manuscript online:
04 August 2023

Article published online:
23 August 2023

© 2023. Thieme. All rights reserved.

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Braunstein JS, Kirschfink M. Complement deficiencies and dysregulation: Pathophysiological consequences, modern analysis, and clinical management. Mol Immunol 2019; 114: 99-311
    PubMedGoogle Scholar
  • 2 Garred P, Tenner AJ, Mollnes TE. Therapeutic targeting of the complement system: From rare diseases to pandemics. Pharmacol Rev 2021; 73: 792-827
    CrossrefPubMedGoogle Scholar
  • 3 Chen M, Daha MR, Kallenberg C. The complement system in systemic autoimmune disease. J Autoimmun 2009; 34: 276-286
    CrossrefPubMedGoogle Scholar
  • 4 Harboe M, Thorgersen EB, Mollnes TE. Advances in assay of complement function and activation. Adv Drug Deliv Rev 2011; 63: 976-987
    CrossrefPubMedGoogle Scholar
  • 5 Zoltán P, Michael K, Ashley FA. Complement analysis in the era of targeted therapeutics. Mol Immunol 2018; 102: 84-88
    CrossrefPubMedGoogle Scholar
  • 6 Stephen T, Thurman JM. Tissue-targeted complement therapeutics. Mol Immunol 2018; 102: 120-128
    CrossrefPubMedGoogle Scholar
  • 7 Deng Z, Tu W, Deng Z, Hu QN. PhID: An open-access integrated pharmacology interactions database for drugs, targets, diseases, genes, side-effects and pathways. J Chem Inf Model 2017; 57: 2395-2400
    CrossrefPubMedGoogle Scholar
  • 8 Xia L, De J, Zhu MX, Chen DF, Lu Y. Juniperus pingii var. wilsonii acidic polysaccharide: Extraction, characterization and anticomplement activity. Carbohydr Polym 2020; 231: 115728
    CrossrefPubMedGoogle Scholar
  • 9 Zhang J, Huo J, Zhao Z, Lu Y, Hong Z, Li H, Chen D. An anticomplement homogeneous polysaccharide from Hedyotis diffusa attenuates lipopolysaccharide-induced acute lung injury and inhibits neutrophil extracellular trap formation. Phytomedicine 2022; 107: 154453
    CrossrefPubMedGoogle Scholar
  • 10 China Pharmacopoeia Committee. Pharmacopoeia of the Peopleʼs Republic China, 1st Division of 2010 Edition. Beijing: China Medical Science Press; 2010: 204-205
    Google Scholar
  • 11 Zhang FX, Liu XF, Ke ZQ, Wu NH, Chen HG, Liu C. The effects of Lysimachia christinae Hance extract fractions on endothelium-dependent vasodilatation. Pharmacology 2019; 104: 36-42
    CrossrefPubMedGoogle Scholar
  • 12 Kim AR, Jung MC, Jeong HI, Song DG, Seo YB, Jeon YH, Park SH, Shin HS, Lee SL, Park SN. Antioxidative and cellular protective effects of Lysimachia christinae Hance extract and fractions. BMC Complement Altern Med 2018; 1: 128
    PubMedGoogle Scholar
  • 13 Wang J, Chen J, Huang J, Lv B, Tao T. Protective effects of total flavonoids from Lysimachia Christinae on calcium oxalate-induced oxidative stress in a renal cell line and renal tissue. Evid Based Complement Alternat Med 2021; 2021: 6667902
    PubMedGoogle Scholar
  • 14 Wang JM, Zhang YY, Zhang YS, Cui Y, Liu J, Zhang BF. Protective effect of Lysimachia christinae against acute alcohol-induced liver injury in mice. Biosci Trends 2012; 6: 89-97
    PubMedGoogle Scholar
  • 15 Wang JM, Liu J, Cui Y, Zhang HW, Feng ZY. Hepatoprotective effects of Lysimachia christinae Hance extracts on acute liver injury induced by tripterygium glycosides in mice. Can J Physiol Pharmacol 2013; 93: 427-433
    PubMedGoogle Scholar
  • 16 Tian YT, Zhao YT, Zeng HL, Zhang YL, Zheng BD. Structural characterization of a novel neutral polysaccharide from Lentinus giganteus and its antitumor activity through inducing apoptosis. Carbohydr Polym 2016; 154: 231-240
    CrossrefPubMedGoogle Scholar
  • 17 Song Y, Zhu M, Hao H, Deng J, Li M, Sun Y, Yang R, Wang H, Huang R. Structure characterization of a novel polysaccharide from Chinese wild fruits (Passiflora foetida) and its immune-enhancing activity. Int J Biol Macromol 2019; 136: 324-331
    CrossrefPubMedGoogle Scholar
  • 18 Wang J, Han J, Lu Z, Lu F. Preliminary structure, antioxidant and immunostimulatory activities of a polysaccharide fraction from Artemisia selengensis Turcz. Int J Biol Macromol 2020; 143: 842-849
    CrossrefPubMedGoogle Scholar
  • 19 Zhou LS, Jiao YK, Tang JY, Zhao ZZ, Zhu HY, Lu Y, Chen DF. Ultrafiltration isolation, structure and effects on H1N1-induced acute lung injury of a heteropolysaccharide from Houttuynia cordata . Int J Biol Macromol 2022; 222: 2414-2425
    CrossrefPubMedGoogle Scholar
  • 20 Sims I, Carnachan S, Bell T, Hinkley S. Methylation analysis of polysaccharides: Technical advice. Carbohydr Polym 2018; 188: 1-7
    CrossrefPubMedGoogle Scholar
  • 21 Shen Y, Liang J, Guo YL, Li Y, Kuang HX, Xia YG. Ultrafiltration isolation, structures and anti-tumor potentials of two arabinose- and galactose-rich pectins from leaves of Aralia elata . Carbohydr Polym 2021; 255: 117326
    CrossrefPubMedGoogle Scholar
  • 22 Qin L, He MJ, Yang YJ, Fu ZT, Mao WJ. Anticoagulant-active sulfated arabinogalactan from Chaetomorpha linum: Structural characterization and action on coagulation factors. Carbohydr Polym 2020; 242: 116394
    CrossrefPubMedGoogle Scholar
  • 23 Zhang JJ, Song ZT, Li Y, Zhang SJ, Guo YQ. Structural analysis and biological effects of a neutral polysaccharide from the fruits of Rosa laevigata . Carbohydr Polym 2021; 265: 118080
    CrossrefPubMedGoogle Scholar
  • 24 Bhanja SK, Maity P, Rout D, Sen IK, Patra S. A xylan from the fresh leaves of Piper betle: Structural characterization and studies of bioactive properties. Carbohydr Polym 2022; 291: 119570
    CrossrefPubMedGoogle Scholar
  • 25 Ganaie F, Maruhn K, Li CX, Porambo RJ, Elverdal PL, Abeygunwardana C, Linden M, Duus J, Sheppard CL, Nahm MH. Structural, Genetic, and Serological Elucidation of Streptococcus pneumoniae Serogroup 24 Serotypes: Discovery of a New Serotype, 24C, with a Variable Capsule Structure. J Clin Microbiol 2021; 59: e0054021
    CrossrefPubMedGoogle Scholar
  • 26 Zhou Y, Ma W, Wang L, Sun W, Li M, Zhang W, Liu Y, Song X, Fan Y. Characterization and antioxidant activity of the oligo-maltose fraction from Polygonum Cillinerve . Carbohydr Polym 2019; 226: 115307
    CrossrefPubMedGoogle Scholar
  • 27 Xiong Q, Luo G, Zheng F, Wu K, Yang H, Chen L, Tian W. Structural characterization and evaluation the elicitors activity of polysaccharides from Chrysanthemum indicum . Carbohydr Polym 2021; 263: 117994
    CrossrefPubMedGoogle Scholar
  • 28 Shi C, Zhu H, Li H, Zeng D, Shi X, Zhang Y, Lu Y, Ling L, Wang C, Chen D. Regulating the balance of Th17/Treg cells in gut-lung axis contributed to the therapeutic effect of Houttuynia cordata polysaccharides on H1N1-induced acute lung injury. Int J Biol Macromol 2020; 158: 52-66
    CrossrefPubMedGoogle Scholar
  • 29 Zhong Q, Wei B, Wang S, Ke S, Chen J, Zhang H, Wang H. The antioxidant activity of polysaccharides derived from marine organisms: An overview. Mar Drugs 2019; 17: 674
    CrossrefPubMedGoogle Scholar
  • 30 Li Y, Nguyen T, Jin J, Lim J, Lee J, Piao M, Mok I, Kim D. Brewing of glucuronic acid-enriched apple cider with enhanced antioxidant activities through the co-fermentation of yeast (Saccharomyces cerevisiae and Pichia kudriavzevii) and bacteria (Lactobacillus plantarum). Food Sci Biotechnol 2021; 30: 555-564
    CrossrefPubMedGoogle Scholar
  • 31 Yue H, Liu Y, Qu H, Ding K. Structure analysis of a novel heteroxylan from the stem of Dendrobium officinale and anti-angiogenesis activities of its sulfated derivative. Int J Biol Macromol 2017; 103: 533-542
    CrossrefPubMedGoogle Scholar
  • 32 Lin Z, Li T, Yu Q, Chen H, Yan C. Structural characterization and in vitro osteogenic activity of ABPB-4, a heteropolysaccharide from the rhizome of Achyranthes bidentate . Carbohydr Polym 2021; 259: 117553
    CrossrefPubMedGoogle Scholar
  • 33 Huo JY, Lu Y, Xia L, Chen DF. Structural characterization and anticomplement activities of three acidic homogeneous polysaccharides from Artemisia annua . J Ethnopharmacol 2020; 247: 112281
    CrossrefPubMedGoogle Scholar
  • 34 Zhou LS, Liao WF, Zeng H, Yao YL, Chen X, Ding K. A pectin from fruits of Lycium barbarum L. decreases β-amyloid peptide production through modulating APP processing. Carbohydr Polym 2018; 201: 65-74
    CrossrefPubMedGoogle Scholar
  • 35 Chen X, Li T, Qing D, Chen J, Zhang Q, Yan C. Structural characterization and osteogenic bioactivities of a novel Humulus lupulus polysaccharide. Food Funct 2020; 11: 1165-1175
    CrossrefPubMedGoogle Scholar
  • 36 Zhang H, Zhong J, Zhang Q, Qing DG, Yan CY. Structural elucidation and bioactivities of a novel arabinogalactan from Coreopsis tinctoria . Carbohydr Polym 2019; 219: 219-228
    CrossrefPubMedGoogle Scholar
  • 37 Li SJ, Li MX, Yue H, Zhou LS, Huang LL, Du ZY, Ding K. Structural elucidation of a pectic polysaccharide from Fructus Mori and its bioactivity on intestinal bacteria strains. Carbohydr Polym 2018; 186: 168-175
    CrossrefPubMedGoogle Scholar
  • 38 Zhang SJ, Li ZG, Wang XL, An LJ, Bao JH, Guo YQ. Isolation, structural elucidation, and immunoregulation properties of an arabinofuranan from the rinds of Garcinia mangostana . Carbohydr Polym 2020; 246: 116567
    CrossrefPubMedGoogle Scholar
  • 39 Shi ZY, An LJ, Zhang SJ, Li ZG, Guo YQ. A heteropolysaccharide purified from leaves of Ilex latifolia displaying immunomodulatory activity in vitro and in vivo . Carbohydr Polym 2020; 245: 116469
    CrossrefPubMedGoogle Scholar
  • 40 Ye ZQ, Li TY, Qing DG, Sun Y, Yan CY. Structural elucidation and osteogenic activity of a novel heteropolysaccharide from Alhagi pseudalhagi . Int J Biol Macromol 2021; 171: 185-197
    CrossrefPubMedGoogle Scholar
  • 41 Jiang P, Meng W, Shi FX, Chen C, Sun Y, Jiao LL. Structural characteristics, antioxidant properties and antiaging activities of galactan produced by Mentha haplocalyx Briq. Carbohydr Polym 2020; 234: 115936
    CrossrefPubMedGoogle Scholar
  • 42 Schartz ND, Tenner AJ. The good, the bad, and the opportunities of the complement system in neurodegenerative disease. J Neuroinflammation 2020; 17: 354
    CrossrefPubMedGoogle Scholar