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Review
. 2021 Jun 21;19(6):350.
doi: 10.3390/md19060350.

Microbial Oligosaccharides with Biomedical Applications

Jian-Lin Xu  1   2   3 , Zhi-Feng Liu  1   2 , Xiao-Wei Zhang  1 , Hai-Li Liu  1 , Yong Wang  1
Affiliations
Review

Microbial Oligosaccharides with Biomedical Applications

Jian-Lin Xu et al. Mar Drugs. .

Abstract

Microbial oligosaccharides have been regarded as one of the most appealing natural products attributable to their potent and selective bioactivities, such as antimicrobial activity, inhibition of α-glucosidases and lipase, interference of cellular recognition and signal transduction, and disruption of cell wall biosynthesis. Accordingly, a handful of bioactive oligosaccharides have been developed for the treatment of bacterial infections and type II diabetes mellitus. Given that naturally occurring oligosaccharides have increasingly gained recognition in recent years, a comprehensive review is needed. The current review highlights the chemical structures, biological activities and divergent biosynthetic origins of three subgroups of oligomers including the acarviosine-containing oligosaccharides, saccharomicins, and orthosomycins.

Keywords: aminooligosaccharide; biomedical applications; biosynthesis; chemical structure; microbial oligosaccharide; orthosomycin; saccharomicin.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The chemical structures of compounds 1–12.
Figure 2
Figure 2
The chemical structures of compounds 13–24.
Figure 3
Figure 3
The chemical structures of compounds 25–39.
Figure 4
Figure 4
The gene cluster and biosynthesis of acarbose and acarviostatins. (A) Comparison between acarbose biosynthetic gene cluster (acb-cluster) of Actinoplanes sp. SE50/110 and acarviostatin biosynthetic gene cluster (sct-cluster) of Streptomyces coelicoflavus ZG0656. The functions of eight genes in the acb-cluster (AcbA, AcbB, AcbV, AcbC, AcbM, AcbO, AcbL, and AcbN) are experimentally defined by proteomic studies, while the functions of the remaining genes in acb-cluster and all genes in the sct-cluster are proposed by bioinformatic analyses. (B) The proposed intracellular biosynthetic pathway of acarbose in Actinoplanes sp. SE50/110 and acarviostatin in Streptomyces coelicoflavus ZG0656. (C) The proposed extracellular biosynthesis of acarviostatins and the carbophor in Streptomyces coelicoflavus ZG0656.
Figure 4
Figure 4
The gene cluster and biosynthesis of acarbose and acarviostatins. (A) Comparison between acarbose biosynthetic gene cluster (acb-cluster) of Actinoplanes sp. SE50/110 and acarviostatin biosynthetic gene cluster (sct-cluster) of Streptomyces coelicoflavus ZG0656. The functions of eight genes in the acb-cluster (AcbA, AcbB, AcbV, AcbC, AcbM, AcbO, AcbL, and AcbN) are experimentally defined by proteomic studies, while the functions of the remaining genes in acb-cluster and all genes in the sct-cluster are proposed by bioinformatic analyses. (B) The proposed intracellular biosynthetic pathway of acarbose in Actinoplanes sp. SE50/110 and acarviostatin in Streptomyces coelicoflavus ZG0656. (C) The proposed extracellular biosynthesis of acarviostatins and the carbophor in Streptomyces coelicoflavus ZG0656.
Figure 5
Figure 5
The chemical structures of saccharomicins A and B (40 and 41). Agl: aglycone; sFuc: sulfated fucose; Sac: saccharosamine; Fuc: fucose; Rha: rhamnose; Eva: 4-epi-vancosamine; Dig: digitoxose.
Figure 6
Figure 6
The gene cluster and biosynthesis of saccharomicin A. (A) The biosynthetic gene cluster of saccharomicin A. The functions of twelve genes in the saccharomicin A biosynthetic gene cluster (Sam5, Sam8, and Sam11-20) are experimentally defined by proteomic studies, while the functions of the remaining genes are proposed by bioinformatic analyses. (B) Biosynthetic pathway of the saccharomicin aglycone. (C) The proposed glycosylation pathway in saccharomicin A biosynthesis.
Figure 7
Figure 7
The chemical structure of hygromycin B (42).
Figure 8
Figure 8
The chemical structures of compounds 43–62. Two orthoester linkages were marked with a red line, while the methylenedioxy bridge was marked with a blue line.
Figure 9
Figure 9
The chemical structures of compounds 63–99. Two orthoester linkages were marked with a red line, while the methylenedioxy bridge was marked with a blue line.
Figure 10
Figure 10
The proposed Avi A biosynthetic pathway (the blue branch is for dichloroisoeverninic acid (moiety A), the orange one is for d-olivose (residues B and C) and 2-deoxy-d-evalose (residue D), the pink branch is for d-fucose (residue E) and methyleurekanate (residue H), while the green one is for d-mannose (residue F) and l-lyxose (residue G); the content in the square bracket represents the published year of genes. The genes in the Avi A biosynthetic gene cluster mentioned above are experimentally defined by proteomic studies.
See this image and copyright information in PMC

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