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Marine Polysaccharides 2022

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 23594

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Special Issue Editors

Dr. Kecheng Li

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Guest Editor

CAS Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China
Interests: chemical biology; bioanalytical chemistry; natural polysaccharides and oligosaccharides; structure-activity relationship; seafood waste high-value utilization

Prof. Dr. Zhanyong Guo

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Guest Editor

Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China
Interests: marine medicine chemistry; polysaccharide; starch polysaccharide; chitosan; antifungal property;algae polysaccharide

Dr. Xiaolin Chen

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Guest Editor

CAS Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China
Interests: polysaccharides; oligosaccharides; algal polysaccharides; antiviral activity; growth-promoting activity; marine drugs

Dr. Jing Wang

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Guest Editor

Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China
Interests: marine medicine; algae polysaccharide; marine acid polysaccharide/oligosaccharides; anti-Parkinson's disease activity; high value utilization of seaweed resources

Special Issue Information

Dear Colleagues,

The ocean has become an important and sustainable source of polysaccharides in recent years. Marine polysaccharides attract increasing interest due to their diverse use in the pharmaceutical, agricultural and food fields. For example, chitin and chitosan from crab and shrimp shells have been used as drug carriers, antimicrobial agents and plant growth stimulators. Glycosaminoglycans from marine sources such as shark cartilage, shellfish and sea cucumber, are shown to have anticoagulant activity and play vital roles in inflammatory diseases. Algal polysaccharides have large structural diversity that makes them useful in the discovery of new drugs. Exopolysaccharides (EPS) isolated from marine microbes in extreme environments are also reported to possess new structures and potential interest in the pharmaceutical field. This Special Issue of Molecules is intended to cover the recent study and utilization of the structural analysis, chemical or enzymatic modification and functional properties of marine polysaccharides as well as their short-chain oligomers. For all studies, essential structural information of poly- and oligosaccharides is highly desirable. Review articles in the field will also be welcome.

Dr. Kecheng Li
Prof. Dr. Zhanyong Guo
Dr. Xiaolin Chen
Dr. Jing Wang
Guest Editors

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Keywords

glycosaminoglycans
marine chitin and chitosan
seaweed polysaccharides
exopolysaccharides
structure analysis
chemical modification
enzymatic degradation
bioactivity and functional properties
structure–function relationship
marine oligosaccharides

Published Papers (10 papers)

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Research

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21 pages, 3008 KiB

Open AccessArticle

Physicochemical Properties and Functional Characteristics of Ecologically Extracted Shrimp Chitosans with Different Organic Acids during Demineralization Step

by Abir El-araby, Lahsen El Ghadraoui and Faouzi Errachidi

Molecules 2022, 27(23), 8285; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27238285 - 28 Nov 2022

Cited by 12 | Viewed by 1652

Abstract

The current study aims to develop eco-friendly and economical chitosans with a wide range of applications using organic acids for shrimp shells demineralization. Chitosan samples were extracted from shrimp (Parapenaeus longirostris) shells and the demineralization step was performed with three organic acids (citric, acetic, and lactic) and two mineral acids (hydrochloric and sulfuric). The chitosans were characterized by Fourier transform infrared (FTIR) spectroscopy, X-ray diffraction (XRD), and scanning electron microscopy (SEM). The chitosans’ physicochemical properties were also determined. The characteristic bands and functional groups of the chitosans were identified by FTIR spectra. The chitosans’ crystallinity order was as follows: Ch_HCl > Ch_Citric > Ch_H2SO4 > Ch_Lactic > Ch_Acetic. The chitosans’ morphological characteristics revealed a smooth surface and fibrous structures with pores. Chitosans extracted by organic acids showed the highest extraction yields. Ch_HCl and Ch_Citric had higher degrees of deacetylation values; 83.67% and 81.47%, respectively. The solubility was proportional to the degree of deacetylation. Furthermore, Ch_H2SO4 and Ch_Citric had lower molecular weight values; 149 kDa and 183 kDa, respectively. Organic acids are as effective as mineral acids for shrimp shells demineralization. The developed process opens up possibilities to produce chitin and chitosan in a more eco-friendly way and at a lower cost in many industrial sectors. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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13 pages, 4729 KiB

Open AccessArticle

Fabrication of Sulfated Heterosaccharide/Poly (Vinyl Alcohol) Hydrogel Nanocomposite for Application as Wound Healing Dressing

by Yang Liu, Ning Wu, Lihua Geng, Yang Yue, Quanbin Zhang and Jing Wang

Molecules 2022, 27(6), 1801; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27061801 - 10 Mar 2022

Cited by 5 | Viewed by 2290

Abstract

Nowadays, natural polysaccharides-based hydrogels have achieved promising results as dressings to promote skin healing. In the present study, we prepared a novel hydrogel nanocomposite with poly(vinyl alcohol) (PVA) and sulfated heterosaccharide (UF), named UPH. The SEM results showed that the UPH had dense porous structures with a high porosity and a specific surface area. The UPH had a good swelling property, which can effectively adsorb exudate and keep the wound moist. The in vitro experiments results showed that the UPH was non-cytotoxic and could regulate the inflammatory response and promote the migration of fibroblasts significantly. The phenotypic, histochemistry, and Western blot analyses showed UPH treatment accelerated the wound healing and recovery of skin tissue at wound sites in a C57BL/6 mouse model. Furthermore, the UPH could promote the inflammation process to onset earlier and last shorter than that in a normal process. Given its migration-promoting ability and physicochemical properties, the UPH may provide an effective application for the treatment and management of skin wounds. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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19 pages, 9053 KiB

Open AccessArticle

Chemical Characterization, Antitumor, and Immune-Enhancing Activities of Polysaccharide from Sargassum pallidum

by Yi Gao, Yizhen Li, Yunze Niu, Hao Ju, Ran Chen, Bin Li, Xiyun Song and Lin Song

Molecules 2021, 26(24), 7559; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247559 - 13 Dec 2021

Cited by 10 | Viewed by 2749

Abstract

Searching for natural products with antitumor and immune-enhancing activities is an important aspect of cancer research. Sargassum pallidum is an edible brown alga that has been used in Chinese traditional medicine for the treatment of tumors. However, the purification and application of its active components are still insufficient. In the present study, the polysaccharides from S. pallidum (SPPs) with antitumor and immune-enhancing activities were isolated and purified, and five polysaccharide fractions (SPP-0.3, SPP-0.5, SPP-0.7, SPP-1, and SPP-2) were obtained. The ratio of total saccharides, monosaccharide composition, and sulfated contents was determined, and their structures were analyzed by Fourier transform infrared spectroscopy. Moreover, bioactivity analysis showed that all five fractions had significant antitumor activity against three types of cancer cells (A549, HepG2, and B16), and can induce cancer cell apoptosis. In addition, the results indicated that SPPs can enhance the proliferation of immune cells and improve the expression levels of serum cytokines (IL-6, IL-1β, iNOS, and TNF-α). SPP-0.7 was identified as the most active fraction and selected for further purification, and its physicochemical properties and antitumor mechanism were further analyzed. Transcriptome sequencing result showed that SPP-0.7 can significantly induce the cell apoptosis, cytokine secretion, and cellular stress response process, and inhibit the normal physiological processes of cancer cells. Overall, SPPs and SPP-0.7 may be suitable for use as potential candidate agents for cancer therapy. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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20 pages, 3861 KiB

Open AccessArticle

Effects of Ulva sp. Extracts on the Growth, Biofilm Production, and Virulence of Skin Bacteria Microbiota: Staphylococcus aureus, Staphylococcus epidermidis, and Cutibacterium acnes Strains

by Mathilde Fournière, Gilles Bedoux, Djouhar Souak, Nathalie Bourgougnon, Marc G. J. Feuilloley and Thomas Latire

Molecules 2021, 26(16), 4763; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164763 - 06 Aug 2021

Cited by 1 | Viewed by 2660

Abstract

Ulva sp. is known to be a source of bioactive compounds such as ulvans, but to date, their biological activity on skin commensal and/or opportunistic pathogen bacteria has not been reported. In this study, the effects of poly- and oligosaccharide fractions produced by enzyme-assisted extraction and depolymerization were investigated, for the first time in vitro, on cutaneous bacteria: Staphylococcus aureus, Staphylococcus epidermidis, and Cutibacterium acnes. At 1000 μg/mL, poly- and oligosaccharide fractions did not affect the growth of the bacteria regarding their generation time. Polysaccharide Ulva sp. fractions at 1000 μg/mL did not alter the bacterial biofilm formation, while oligosaccharide fractions modified S. epidermidis and C. acnes biofilm structures. None of the fractions at 1000 μg/mL significantly modified the cytotoxic potential of S. epidermidis and S. aureus towards keratinocytes. However, poly- and oligosaccharide fractions at 1000 μg/mL induced a decrease in the inflammatory potential of both acneic and non-acneic C. acnes strains on keratinocytes of up to 39.8%; the strongest and most significant effect occurred when the bacteria were grown in the presence of polysaccharide fractions. Our research shows that poly- and oligosaccharide Ulva sp. fractions present notable biological activities on cutaneous bacteria, especially towards C. acnes acneic and non-acneic strains, which supports their potential use for dermo-cosmetic applications. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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14 pages, 16416 KiB

Open AccessArticle

Novel 2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives: Synthesis, Characterization, Moisture Absorption and Retention Properties

by Yingqi Mi, Qin Miao, Jingmin Cui, Wenqiang Tan and Zhanyong Guo

Molecules 2021, 26(14), 4238; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26144238 - 12 Jul 2021

Cited by 7 | Viewed by 1837

Abstract

Recent years have seen a steady increase in interest and demand for the use of humectants based on biodegradable natural polymers in many fields. The aim of this paper is to investigate the moisture absorption and retention properties of 2-hydroxypropyltrimethyl ammonium chitosan derivatives which were modified by anionic compounds via ion exchange. FTIR, ¹H NMR, and ¹³C NMR spectroscopy were used to demonstrate the specific structures of chitosan derivatives. The degrees of substitution for objective products were calculated by the integral ratio of hydrogen atoms according to ¹H NMR spectroscopy. Meanwhile, moisture absorption of specimens was assayed in a desiccator at different relative humidity (RH: 43% and 81%), and all target products exhibited enhanced moisture absorption. Furthermore, moisture retention measurement at different relative humidity (RH: 43%, 81%, and drier silica gel) was estimated, and all target products possessed obviously improved moisture retention property. Specifically, after 48 h later, the moisture retention property of HACBA at 81% RH was 372.34%, which was much higher than HA (180.04%). The present study provided a novel method to synthesize chitosan derivatives with significantly improved moisture absorption and retention properties that would serve as potential humectants in biomedical, food, medicine, and cosmetics fields. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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13 pages, 2179 KiB

Open AccessArticle

An Exploration of Seaweed Polysaccharides Stimulating Denitrifying Bacteria for Safer Nitrate Removal

by Hui Zhang, Lin Song, Xiaolin Chen and Pengcheng Li

Molecules 2021, 26(11), 3390; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113390 - 03 Jun 2021

Cited by 6 | Viewed by 1986

Abstract

Excessive use of nitrogen fertilizer in intensively managed agriculture has resulted in abundant accumulation of nitrate in soil, which limits agriculture sustainability. How to reduce nitrate content is the key to alleviate secondary soil salinization. However, the microorganisms used in soil remediation cause some problems such as weak efficiency and short survival time. In this study, seaweed polysaccharides were used as stimulant to promote the rapid growth and safer nitrate removal of denitrifying bacteria. Firstly, the growth rate and NO₃⁻-N removal capacity of three kinds of denitrifying bacteria, Bacillus subtilis (BS), Pseudomonas stutzeri (PS) and Pseudomonas putida (PP), were compared. The results showed that Bacillus subtilis (BS) had a faster growth rate and stronger nitrate removal ability. We then studied the effects of Enteromorpha linza polysaccharides (EP), carrageenan (CA), and sodium alginate (AL) on growth and denitrification performance of Bacillus subtilis (BS). The results showed that seaweed polysaccharides obviously promoted the growth of Bacillus subtilis (BS), and accelerated the reduction of NO₃⁻-N. More importantly, the increased NH₄⁺-N content could avoid excessive loss of nitrogen, and less NO₂⁻-N accumulation could avoid toxic effects on plants. This new strategy of using denitrifying bacteria for safely remediating secondary soil salinization has a great significance. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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15 pages, 3095 KiB

Open AccessArticle

Preparation of New Sargassum fusiforme Polysaccharide Long-Chain Alkyl Group Nanomicelles and Their Antiviral Properties against ALV-J

by Yuhao Sun, Xiaolin Chen, Hong Liu, Song Liu, Huahua Yu, Xueqin Wang, Yukun Qin and Pengcheng Li

Molecules 2021, 26(11), 3265; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113265 - 28 May 2021

Cited by 6 | Viewed by 2349

Abstract

Avian leukosis virus subgroup J (ALV-J) is an immunosuppressive virus which has caused heavy losses to the poultry breeding industry. Currently, there is no effective medicine to treat this virus. In our previous experiments, the low-molecular-weight Sargassum fusiforme polysaccharide (SFP) was proven to possess antiviral activity against ALV-J, but its function was limited to the virus adsorption stage. In order to improve the antiviral activity of the SFP, in this study, three new SFP long-chain alkyl group nanomicelles (SFP-C12M, SFP-C14M and SFP-C16M) were prepared. The nanomicelles were characterized according to their physical and chemical properties. The nanomicelles were characterized by particle size, zeta potential, polydispersity index, critical micelle concentration and morphology. The results showed the particle sizes of the three nanomicelles were all approximately 200 nm and SFP-C14M and SFP-C16M were more stable than SFP-C12M. The newly prepared nanomicelles exhibited a better anti-ALV-J activity than the SFP, with SFP-C16M exhibiting the best antiviral effects in both the virus adsorption stage and the replication stage. The results of the giant unilamellar vesicle exposure experiment demonstrated that the new virucidal effect of the nanomicelles might be caused by damage to the phospholipid membrane of ALV-J. This study provides a potential idea for ALV-J prevention and development of other antiviral drugs. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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17 pages, 6182 KiB

Open AccessArticle

Characterization of Different Salt Forms of Chitooligosaccharides and Their Effects on Nitric Oxide Secretion by Macrophages

by Ronge Xing, Chaojie Xu, Kun Gao, Haoyue Yang, Yongliang Liu, Zhaoqian Fan, Song Liu, Yukun Qin, Huahua Yu and Pengcheng Li

Molecules 2021, 26(9), 2563; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092563 - 28 Apr 2021

Cited by 4 | Viewed by 1625

Abstract

In this paper, chitooligosaccharides in different salt forms, such as chitooligosaccharide lactate, citrate, adipate, etc., were prepared by the microwave method. They were characterized by SEM, FTIR, NMR, etc., and the nitric oxide (NO) expression was determined in RAW 264.7 cells. The results showed that pure chitooligosaccharide was an irregular spherical shape with rough surface, and its different salt type products are amorphous solid with different honeycomb sizes. In addition to the characteristic absorption peaks of chitooligosaccharides, in FTIR, the characteristic absorption of carboxyl group, methylene group, and aromatic group in corresponding acid appeared. The characteristic absorption peaks of carbon in carboxyl group, hydrogen and carbon in methyl, methylene group, and aromatic group in corresponding acid also appeared in NMR. Therefore, the sugar ring structure and linking mode of chitooligosaccharides did not change after salt formation of chitooligosaccharides. Different salt chitooligosaccharides are completely different in promoting NO secretion by macrophages, and pure chitooligosaccharides are the best. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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Review

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22 pages, 7974 KiB

Open AccessReview

Formation of Amphiphilic Molecules from the Most Common Marine Polysaccharides, toward a Sustainable Alternative?

by Tiphaine Wong, Lorette Brault, Eric Gasparotto, Romuald Vallée, Pierre-Yves Morvan, Vincent Ferrières and Caroline Nugier-Chauvin

Molecules 2021, 26(15), 4445; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154445 - 23 Jul 2021

Cited by 8 | Viewed by 2914

Abstract

Marine polysaccharides are part of the huge seaweeds resources and present many applications for several industries. In order to widen their potential as additives or bioactive compounds, some structural modifications have been studied. Among them, simple hydrophobization reactions have been developed in order to yield to grafted polysaccharides bearing acyl-, aryl-, alkyl-, and alkenyl-groups or fatty acid chains. The resulting polymers are able to present modified physicochemical and/or biological properties of interest in the current pharmaceutical, cosmetics, or food fields. This review covers the chemical structures of the main marine polysaccharides, and then focuses on their structural modifications, and especially on hydrophobization reactions mainly esterification, acylation, alkylation, amidation, or even cross-linking reaction on native hydroxyl-, amine, or carboxylic acid functions. Finally, the question of the necessary requirement for more sustainable processes around these structural modulations of marine polysaccharides is addressed, considering the development of greener technologies applied to traditional polysaccharides. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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15 pages, 1133 KiB

Open AccessReview

Design of Chitosan Sterilization Agents by a Structure Combination Strategy and Their Potential Application in Crop Protection

by Weixiang Liu, Yukun Qin and Pengcheng Li

Molecules 2021, 26(11), 3250; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113250 - 28 May 2021

Cited by 5 | Viewed by 2327

Abstract

Chitosan is the only cationic polysaccharide in nature. It is a type of renewable resource and is abundant. It has good biocompatibility, biodegradability and biological activity. The amino and hydroxyl groups in its molecules can be modified, which enables chitosan to contain a variety of functional groups, giving it a variety of properties. In recent years, researchers have used different strategies to synthesize a variety of chitosan derivatives with novel structure and unique activity. Structure combination is one of the main strategies. Therefore, we will evaluate the synthesis and agricultural antimicrobial applications of the active chitosan derivatives structure combinations, which have not been well-summarized. In addition, the advantages, challenges and developmental prospects of agricultural antimicrobial chitosan derivatives will be discussed. Full article

(This article belongs to the Special Issue Marine Polysaccharides 2022)

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