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Review
Peer-Review Record

Are Structurally Modified Galactomannan Derivatives Biologically Active?

Polysaccharides 2021, 2(1), 1-15; https://doi.org/10.3390/polysaccharides2010001
by Maurycyo Silva Geronço 1, Igor Frederico da Silveira Ramos 1, Edson Cavalcanti da Silva Filho 1, Márcia dos Santos Rizzo 1, Alessandra Braga Ribeiro 2,* and Marcilia Pinheiro da Costa 1
Reviewer 1: Anonymous
Reviewer 2: Anonymous
Reviewer 3: Anonymous
Polysaccharides 2021, 2(1), 1-15; https://doi.org/10.3390/polysaccharides2010001
Submission received: 29 November 2020 / Revised: 25 December 2020 / Accepted: 5 January 2021 / Published: 8 January 2021
(This article belongs to the Collection Bioactive Polysaccharides)

Round 1

Reviewer 1 Report

Described problem is intersting for chemical and biomedical point of view. Informations in review are rather fresh and sound good. But in reviewer opinion Authors should be introduce more information about structure of modified galactomannan (like in title of manuscript). Galactomannans generate in solutions entanglement structure. Authors didn't discussed this problem in aspect of modified galactomannans. It will be intersting to show some aspects of this problem in this review.

 

Author Response

Dear reviewer,

Thank for the considerations. We believe that observations were to improve the work.

The information we included in the manuscript:

Page 3, line 119: Among these polysaccharides, galactomannans have been extensively studied for molecular modifications. Galactomannans can be modified mainly by chemical or enzymatic methods. A large number of hydroxyl groups of galactomannans can be altered by etherification, esterification, or oxidation. The changes that add hydrophilic groups to molecules of galactomannans can reduce hydrogen bonds between the molecules and improve solubility and swelling characteristics. Other characteristics that are also improved by the increase in hydrophilicity are the clarity of the gum and the compatibility with electrolytes [24].

Page 4, line 154: Most studies about sulfation of galactomannans used dimethylformamide as the solvent and SO3– pyridine complex as a sulfating reagent [6,8,9,23,26-29]. Several studies report preferred sulfation for the 6-CH2 groups due to their higher reactivity with esterifying agents and a degree of sulfating (DS) ranging from 0.4 to 1.85. These sulfated galactomannans are composed of negatively charged sulfate groups that are related to their biological activities [4,5,6,8,9,23,26-29].

Page 4, line 165: Protein-free guar gum was oxidized by the method of the TEMPO (2,2,6,6-tetramethylpiperidine-1-oxide radical)/NaBr/NaClO system [25]. This oxidized derivative presents a degree of substitution of 0.36, and the oxidation happened preferentially in the carbon 6 of the mannose residue. FT-IR and 13C NMR spectrum showed the presence of the COOH group in the oxidized molecule.

Page 5, line 179: Wang et al. [20] phosphorylated the galactomannan chains of Cyamopsis tetragonolobo (guar gum) using POCl3/pyridine and obtained phosphorylated derivatives with the degree of substitution (DS) of 0.35–0.52. They observed an expanded conformation of phosphorylated derivatives with intramolecular hydrogen bonds due to the electrostatic potential of SO3H groups. Experiments with the phosphorylated derivatives with different DS were conducted to evaluate the influence of this parameter on the antioxidant activity.

Page 5, line 185: Hydrolysis is an important strategy for polysaccharide modification. In the enzymatic method, the galactose side chains, or the main mannose chain can be cleaved, and the α-galactosidase and β-mannanase can be used. Compared with the chemical modification method, the enzymatic method is simple to control, and the reaction conditions are milder [24]. The biological activity of the locust bean gum galactomannan hydrolyzed by thermostable β-D-mannanase was evaluated by Chen et al. [31]. In this study, after 24 h of the enzymatic reaction, the weight average molecular weight of galactomannan derivative reduced from 5,580,010 to 3,188, and the hydrolysate containing the following manno-oligosaccharides: mannobiose, mannotriose, and mannotetrose.

Page 5, line 197: Polysaccharides are suitable binders for complexation reactions with the cationic form of vanadium due to the affinity of this metal for hydroxyl groups free of these polyhydroxyl compounds. Complexation of vanadium (IV,V) with monosaccharides is facilitated by the presence of ligands containing vicinal cis-OH groups [19,32].

References

  1. Wang, X.; Wang, J.; Zhang, J.; Zhao, B., Yao, J.; Wang, Y. Structure-antioxidant relationships of sulfated galactomannan from guar gum. International Journal of Biological Macromolecules 2010, 46(1), 59–66.
  2. Muschin, T.; Budragchaa, D.; Kanamoto, T.; Nakashima, H.; Ichiyama, K.; Yamamoto, N.; Shuqin, H.; Yoshida, T. Chemically sulfated natural galactomannans with specific antiviral and anticoagulant activities. International Journal of Biological Macromolecules 2016, 89, 415–420.
  3. Cunha de Padua, M. M.; Cadena, S. M. S. C.; Petkowicz, C. L. O.; Martinez, G. R.; Noleto, G. R. Galactomannan from Schizolobium amazonicum seed and its sulfated derivatives impair metabolism in HepG2 cells. International Journal of Biological Macromolecules 2017, 101, 464–473.
  4. Chrestani, F.; Sierakowski, M. R.; Uchoa, D. E. A.; Nozawa, C.; Sassaki, G. L.; Gorin, P. A. J.; Ono, L. In vitro antiherpetic and antirotaviral activities of a sulfate prepared from Mimosa scabrella galactomannan. International Journal of Biological Macromolecules 2009, 45(5), 453–457.
  5. Mestechkina, N. M.; Shcherbukhin, V. D.; Bannikova, G. E.; Varlamov, V. P.; Drozd, N. N.; Tolstenkov, A. S.; Makarov, V. A.; Tikhonov, V. E. Anticoagulant activity of low-molecular-weight sulfated derivatives of galactomannan from Cyamopsis tetragonoloba (L.) seeds. Applied Biochemistry and Microbiology 2008, 44(1), 111–116.
  6. Noleto, G. R.; Petkowicz, C. L. O.; Mercê, A. L. R.; Noseda, M. D.; Méndez-Sánchez, S. C.; Reicher, F.; Oliveira, M. B. M. Two galactomannan preparations from seeds from Mimosa scabrella (bracatinga): Complexation with oxovanadium (IV/V) and cytotoxicity on HeLa cells. Journal of Inorganic Biochemistry 2009, 103(5), 749–757.
  7. Wang, J.; Yang, T. Synthesis and characterization of phosphorylated galactomannan: The effect of DS on solution conformation and antioxidant activities. Carbohydrate Polymers 2014, 113, 325–335.

 

  1. Godoi, A. M.; Faccin-Galhardi, L. C.; Lopes, N.; Nozawa, C.; Almeida, R. R.; Ricardo, N. M. P. S.; Linhares, R. E. C. Characterization and antiherpetic activity of native and chemically sulfated polysaccharide from Adenanthera pavonina. Current Pharmaceutical Biotechnology 2015, 16(11), 1024-1031.
  2. Ba, J.; Gao, Y.; Xu, Q.; Qin, M. Research Development of Modification of Galactomannan Gums from Plant Resources. Advanced Materials Research 2012, 482-484, 1628-1631.
  3. Ono, L.; Wollinger, W.; Rocco, I. M.; Coimbra, T. L. M.; Gorin, P. A. J.; Sierakowski, M. R. In vitro and in vivo antiviral properties of sulfated galactomannans against yellow fever virus (BeH111 strain) and dengue 1 virus (Hawaii strain). Antiviral Research 2003, 60(3), 201–208.
  4. Castro, R. R.; Silva, C. M. M.; Nunes, R. M.; Cunha, P. L. R.; Paula, R. C. M.; Feitosa, J. P. A.; Girão, V. C. C.; Pompeu, M. M. L.; Leite, J. A. D.; Rocha, F. A. C. Structural characteristics are crucial to the benefits of guar gum in experimental osteoarthritis. Carbohydrate Polymers 2016, 150, 392–399.
  5. Ono, L.; Wollinger, W.; Rocco, I. M.; Coimbra, T. L. M.; Gorin, P. A. J.; Sierakowski, M. R. In vitro and in vivo antiviral properties of sulfated galactomannans against yellow fever virus (BeH111 strain) and dengue 1 virus (Hawaii strain). Antiviral Research 2003, 60(3), 201–208.
  6. Gemin, E.; Ferreira, C. E. O.; Sierakowski, M. R.; Jorge, T. R.; Joineau, M. E. G.; Ono, L. In vitro anti-HSV-1 activity of a chemically sulfated galactomannan from Leucaena leucocephala seeds. Journal of Basic and Applied Pharmaceutical Sciences 2010, 31(2), 165–170.
  7. Lopes, N.; Faccin-Galhardi, L. C.; Espada, S. F.; Pacheco, A. C.; Ricardo, N. M. P. S.; Linhares, R. E. C.; Nozawa, C. Sulfated polysaccharide of Caesalpinia ferrea inhibits herpes simplex virus and poliovirus. International Journal of Biological Macromolecules 2013, 60, 93–99.
  8. Marques, M. M. M.; Morais, S. M.; Silva, A. R. A.; Barroso, N. D.; Pontes Filho, T. R.; Araujo, F. M. D. C.; Vieira, I. G. P.; Lima, D. M.; Guedes, M. I. F. Antiviral and Antioxidant Activities of Sulfated Galactomannans from Plants of Caatinga Biome. Evidence-Based Complementary and Alternative Medicine 2015, 2015, 1-8.
  9. Chen, W. L.; Chen, H. L.; Guo, G. W.; Huang, Y. C., Chen, C. Y., Tsai, Y.; Huang, K. F.; Chao-Hsun Yang, C. H. Locust bean gum galactomannan hydrolyzed by thermostable β-D-mannanase may reduce the secretion of pro-inflammatory factors and the release of granule constituents. International Journal of Biological Macromolecules 2018, 114, 181–186.
  10. Noleto, G. R.; Mercê, A. L. R.; Iacomini, M.; Gorin, P.A.J.; Soccol, V. T.; Oliveira, M. B. Effects of a lichen galactomannan and its vanadyl (IV) complex on peritoneal macrophages and leishmanicidal activity. Molecular and Cellular Biochemistry 2002, 233, 73–83.

Author Response File: Author Response.pdf

Reviewer 2 Report

This manuscript provides an overview of recent studies that apply galactomannan modification or derivatization strategies to improve their properties for applications in the biomedical area. In particular it focuses on the study of pharmacological activities of structurally modified galactomannan derivatives, including the following nine issues, antiviral activity, antimicrobial activity, anticoagulant and fibrinolytic activities, chemopreventive activity, anticancer activity, antioxidant activity, analgesia and chondroprotection activities, immunomodulatory activity, antileishmania activity. Through this review, the authors conclude that there have some success of modified galactomannans for pharmacological purposes, meanwhile, there are also the loss of bioactivity of the original polysaccharide after chemical changes in its original structures. This point may be meaningful for the related researchers who tempt to apply galactomannan modification or derivatization in the biomedical area. 

Author Response

Dear reviewer,

Thank you for the considerations.

Reviewer 3 Report

Review report on the manuscript titled:

“Are structurally modified galactomannan derivatives biologically active?

 

The paper presents a narrative review on the biological properties of galactomannans/ polysaccharide sand related derivatives obtained by sulfation, complexation, and phosphorylation. Their pharmacological activities such as antiviral, antimicrobial, anticoagulant, fibrinolytic, chemopreventive, anticancer, antioxidant, chondroprotective, analgesic and immunomodulatory effects are discussed. The authors concluded that in some studies, the loss of bioactivity of the original polysaccharide was noticed.

Comments and observations:

  1. The paper is well written, pointing out the main strategies for obtaining galactomannan derivatives and the pharmacological activities of galactomannan derivatives. However, a systematic review or meta-analyses should be considered (according the available instructions displayed on the journal website), as polysaccharides are a large class of molecules and inclusion criteria are required in order to prepare a review paper.
  2. Although the main biological activities are presented, the authors should also have to take into account some novel approach such as nanotechnology- derived biomedical applications. The new trend in nanoparticles fabrication is related to the “green chemistry “techniques, especially using different saccharides as reducing agent for their fabrication, while avoiding the toxic chemicals. A good example of nanoparticles for biomedical and pharmacological applications could be find in the following papers:

“Surface modifications of the titanium mesh for cranioplasty using selenium nanoparticles coating”, JOURNAL OF ADHESION SCIENCE AND TECHNOLOGY, 2018, Volume: 32 Issue: 22 Pages: 2509-2522;

Or “Eco-friendly, Facile and Rapid Way for Synthesis of Selenium Nanoparticles- Production, structural and morphological characterization”, REVISTA DE CHIMIE 2017, Volume: 68 Issue: 12 Pages: 2963-2966. In this studies, you can find a novel eco-friendly method for nano-Se production using lactose, glucose, galactose and starch as reducing agent.

 

  1. The main goal of the study should be better highlighted in the introduction section.

Taking into account the above observations, I recommend the publication of the manuscript after major revision.

 

Comments for author File: Comments.docx

Author Response

Dear reviewer,

Thank you for the considerations. We believe that observations were to improve the work.

Reply:

  1. The information about the research methodology was added to the manuscript:

Page 3, line 99: This review focuses on the study of the intrinsic pharmacological activities of structurally modified galactomannan derivatives. A search for articles referring to the modified galactomannans was conducted. The keywords ‘modified galactomannans and biological activity’ or ‘galactomannan derivatives and biological activity’ were used to procure scientific articles in electronic databases, including PubMed, Scopus, and Web of Science. The selection of the articles was based on the following inclusion criteria: full-text articles published containing the keywords above that led to chemical modifications and evaluated the intrinsic pharmacological properties of the modified biopolymer, without restricting the year of publication. Modified galactomannans that had not been evaluated for biological characterization were excluded from the study. Modified galactomannans that were formulated with the addition of active substances were also not considered.

 

  1. The information on innovative approaches has been included in the manuscript:

Page 15, line 885: The inputs of natural origin have become an important source of renewable resources, based on green chemistry principles for application in the industrial sector. Among these, polysaccharides stand out because of their great versatility of [45,46]. In addition to the proposal to use native or derived polysaccharides as biologically active substances, several studies report the use of these in nanoformulations for biomedical applications. These alternative materials are currently used in several innovations in the nanotechnological area [47,48]. Mainly, plant-derived galactomannans have been frequently used to develop several types of drug delivery systems, including polymeric nanoparticles [49,50,51], liposomes [52], microparticles [14,53], beads [54], hydrogels [55], aerogels [1,13], and mucoadhesive systems [2].

 

References

  1. Rossi, B.; Campia, P.; Merlini, L.; Brasca, M.; Pastori, N.; Farris, S.; Melone, L.; Punta, C.; Galante, Y. M. An aerogel obtained from chemo-enzymatically oxidized fenugreek galactomannans as a versatile delivery system. Carbohydrate Polymers 2016, 144, 353–361.
  2. Bassi, P.; Kaur, G. Fenugreek gum derivatives with improved bioadhesion and controlled drug release: In vitro and in vivo characterization. Journal of Drug Delivery Science and Technology 2015a, 29, 42–54.
  3. Ponzini, E.; Natalello, A.; Usai, F.; Bechmann, M.; Peri, F.; Müller, N.; Grandori, R. Structural characterization of aerogels derived from enzymatically oxidized galactomannans of fenugreek, sesbania and guar gums. Carbohydrate Polymers 2019, 207, 510–520.
  4. Benny, I.S.; Gunasekar, V.; Ponnusami, V. Review on Application of Xanthan Gum in Drug Delivery. International Journal of PharmTech Research 2014, 6(4), 1322-1326.
  5. Pleissner, D.; Kümmerer, K. Green Chemistry and Its Contribution to Industrial Biotechnology. Advances in Biochemical Engineering/Biotechnology 2020,173, 281-298.

 

  1. Cavalu, S.; Kamel, E.; Laslo, V.; Fritea, L.; Costea, T.; Antoniac, I.V.; Vasile, E.; Antoniac, A.; Semenescu, A.; Mohan, A.; Saceleanu, V.; Vicas, S. Eco-friendly, Facile and Rapid Way for Synthesis of Selenium Nanoparticles. Production, structural and morphological characterisation. Revista de Chimie 2017, 68(12), 2963-2966.
  2. Cavalu, S.; Antoniac, I.V.; Fritea, L.; Mates, L.M.; Milea, C.; Laslo, V.; Vicas, S.; Mohan, A. Surface modifications of the titanium mesh for cranioplasty using selenium nanoparticles coating. Journal of Adhesion Science and Technology 2018, 32(22), 2509–2522.
  3. Islan, G.A.; Mukherjee, A.; Castro, G.R. Development of biopolymer nanocomposite for silver nanoparticles and Ciprofloxacin controlled release. International Journal of Biological Macromolecules 2015, 72, 740–750.
  4. Teixeira, G.F.D.; Vieira-Neto, A.E.; da Costa, F.N., Silva, A.R.A.; Campos, A.R. Antinociceptive effect of (-)-α-bisabolol in nanocapsules. Biomedicine and Pharmacotherapy 2017, 91, 946–950.
  5. Srivastav, A.K.; Dhiman, N.; Tiwari, R.; Arjaria, N.; Prakash, J.; Jagdale, P.; Ayanur, A.; Singh, D.; Satyakam Patnaik, S.; Kumar, M. Sub-acute oral exposure of zinc oxide nanoparticles causes alteration in iron homeostasis through acute phase response: A protective effect by surface modification. Journal of Trace Elements in Medicine and Biology 2018, 270–287.
  6. Pu, C.; Tang, W.; Li, X.; Li, M.; Sun, Q. Stability enhancement efficiency of surface decoration on curcumin-loaded liposomes: Comparison of guar gum and its cationic counterpart. Food Hydrocolloids 2019, 87, 29–37.
  7. Bosio, V.E.; Basu, S.; Abdullha, F.; Villalba, M.E.C; Güida, J.A.; Mukherjee, A.; Castro, G.R. Encapsulation of Congo Red in carboxymethyl guar gum-alginate gel microspheres. Reactive and Functional Polymers 2014, 82, 103–110.
  8. Verma, S.; Ahuja, M. Carboxymethyl sesbania gum: Synthesis, characterization and evaluation for drug delivery. International Journal of Biological Macromolecules 2017 98, 75–83.
  9. Seeli, D.S.; Prabaharan, M. Guar gum oleate-graft-poly(methacrylic acid) hydrogel as a colon-specific controlled drug delivery carrier. Carbohydrate Polymers 2017, 158, 51–57.

 

  1. The information below was added in the introduction of the manuscript:

Page 2, line 74: The galactomannans are suitable for used in chemical modification methods, as they have a simple structure. Their derivatives can be easily characterized chemically. Sulfation is an effective, versatile, and simple modification method applied to galactomannans to improve their biological activity. However, other methods can also be used to change the structure of galactomannans [16,17,18].

Page 3, line 97: In view of the aforementioned, this work aimed to provide an overview of the studies that applied methods for structural modification of galactomannans to evaluate or improve their properties for applications in the biomedical area. This review focuses on the study of the intrinsic pharmacological activities of structurally modified galactomannan derivatives. A search for articles referring to the modified galactomannans was conducted. The keywords ‘modified galactomannans and biological activity’ or ‘galactomannan derivatives and biological activity’ were used to procure scientific articles in electronic databases, including PubMed, Scopus, SciELO, and Web of Science. The selection of the articles was based on the following inclusion criteria: full-text articles published containing the keywords above that led to chemical modifications and evaluated the intrinsic pharmacological properties of the modified biopolymer, without restricting the year of publication. Modified galactomannans that had not been evaluated for biological characterization were excluded from the study. Modified galactomannans that were formulated with the addition of active substances were also not considered.

References

  1. Xie, J.-H.; Wang, Z.-J.; Shen, M.-Y.; Nie, S.-P.; Gong, B.; Li, H.-S.; Zhao, Q.; Li, W.-J.; Xie, M.-Y. Sulfated modification, characterization and antioxidant activities of polysaccharide from Cyclocarya paliurus. Food hydrocolloids 2016, 53, 7-15.
  2. Zhang, Z.; Wang, H.; Chen, T.; Zhang, H.; Liang, J.; Kong, W.; Yao, J.; Zhang, J.; Wang, J. Synthesis and structure characterization of sulfated galactomannan from fenugreek gum. International Journal of Biological Macromolecules 2019, 125, 1184-1191.
  3. Barddal, H.P.O.; Faria, F.A.M.; Nogueira, A.V.; Iacomini, M.; Cipriani, T.R. Anticoagulant and antithrombotic effects of chemically sulfated guar gum. International Journal of Biological Macromolecules 2020, 45, 604-610.

 

Author Response File: Author Response.pdf

Round 2

Reviewer 1 Report

In reviewer opinion manuscript sounds good and id ready to publication.

Reviewer 3 Report

The revised manuscript is now suitable for publication. The authors made substantial improvements to thier work

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