Plants arabinogalactans: From structures to physico-chemical and biological properties

Saeidy, Sima; Petera, Benjamin; Pierre, Guillaume; Fenoradosoa, Taratra Andrée; Djomdi, Djomdi; Michaud, Philippe; Delattre, Cédric

doi:10.1016/j.biotechadv.2021.107771

“…All NMR spectra were recorded on a Bruker Avance III HD Ascend 600 MHz instrument using DMSO-d6 as the solvent. 1 H NMR and 13 C NMR spectra were referenced to residual solvent peaks. 1 19 F NMR spectra were referenced to internal standards, as noted.…”

Section: General Experimental Methodsmentioning

confidence: 99%

“…1 H NMR (600 MHz, DMSO-d6) δ 9.20 (s, 1H, Ar-N-H), 7.74 -7.68 (m, 2H, tosyl Ar-H), 7.38 -7.35 (m, 2H, tosyl Ar-H), 7.34 (d, J = 8.6 Hz, 2H, Ar-H ortho to Boc), 6.90 -6.84 (m, 2H, Ar-H ortho to sugar), 5.36 (d, J = 5.2 Hz, 1H, C2-OH), 5.30 (d, J = 5.5 Hz, 1H, C3-OH), 5.18 (d, J = 5.1 Hz, 1H, C4-OH), 4.76 (d, J = 7.7 Hz, 1H, H1), 4.24 (dd, J 10.7, 2.0 Hz, 1H, H6a), 4.05 (dd, J = 10.7, 6.5 Hz, 1H, H6b), 3.58 (ddd, J = 9.9, 6.5, 2.0 Hz, 1H, H5), 3.23 (td, J = 8.9, 5.1 Hz, 1H, H3), 3.19 -3.14 (m, 1H, H2), 3.09 (ddd, J = 9.9, 8.7, 5.4 Hz, 1H, H4), 2.38 (s, 3H, tosyl CH3), 1.47 (s, 9H, t Bu-H). 13…”

Section: N-boc-p-aminophenyl-6-o-tosyl-β-d-glucopyranoside (5)mentioning

confidence: 99%

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

Rueda

¹

,

McCubbin

²

,

Shieh

³

et al. 2023

Preprint

0

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Small molecule fluorescent probes that bind selectively to plant cell wall polysaccharides have been instrumental in elucidating the localization and function of these glycans. Arabinogalactan proteins (AGPs) are cell wall proteoglycans implicated in essential functions such as cell signaling, plant growth, and programmed cell death. There is currently no small molecule probe capable of fluorescently labeling AGPs. The Yariv reagents are the only small molecules that bind AGP, and have been used to study AGP function and isolate AGPs via precipitation of an AGP-Yariv complex. However, the Yariv reagents are not fluorescent, rendering them ineffective for localization studies using fluorescence microscopy. A fluorescent version of a Yariv reagent that is capable of both binding as well as imaging AGPs would provide a powerful tool for studying AGPs in planta. Herein, we describe the synthesis of an azido analog of the Yariv reagent that can be further functionalized with a fluorophore to provide a glycoconjugate that binds AGP and is fluorescent. We show that the modified reagent binds gum arabic in in vitro binding assays when used in conjunction with the βGlcYariv reagent. Fluorescent imaging of AGP in fixed maize leaf tissue enables localization of AGP to cell walls in the leaf. Significantly, imaging can also be carried out using fresh tissue. This represents the first small molecule probe that can be used to visualize AGP using fluorescence microscopy.

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“…1 1 Hz, 2H, H6a), 3.48 (dd, J = 12.0, 5.6 Hz, 2H, H6b), 3.34 (ddd, J = 9.9, 4.8, 2.7 Hz, 1H, H5), 3.31 (t, J = 8.9 Hz, 2H, H3), 3.24 (dd, J = 9.0, 7.7 Hz, 2H, H2), 3.18 (t, J = 9.2 Hz, 2H, H4). 13…”

Section: Redissolution and Reprecipitationmentioning

confidence: 99%

“…1 H NMR (600 MHz, CD3OD) δ 7.32 (d, J = 8.5 Hz, 2H, Ar-H ortho to Boc), 7.08 -7.01 (m, 2H, Ar-H ortho to sugar), 4.85 -4.83 (m, 1H, H1), 3.60 (dd, J = 13.1, 2.3 Hz, 1H, H6a), 3.56 (ddd, J = 9.3, 6.6, 2.3 Hz, 1H, H5), 3.50 -3.41 (m, 3H, H2, H6b, H3), 3.36 (td, J = 6.2, 3.1 Hz, 1H, H4), 1.53 (s, 9H, t Bu-H). 13…”

Section: N-boc-p-aminophenyl-6-deoxy-6-azido-β-d-glucopyranoside (6)mentioning

confidence: 99%

“…[10][11][12] AGPs contain protein domains rich in hydroxyproline residues that are glycosylated with long β(1→3) linked galactan chains that make up the bulk of AGP mass. 13,14 Shorter branching β(1→6) galactan side chains are linked from the galactan main chains and are commonly decorated with arabinofuranose residues and other monosaccharides, with variations in the specific composition of the branches depending on the species and plant tissue.…”

Section: Introductionmentioning

confidence: 99%

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A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

Rueda

¹

,

McCubbin

²

,

Shieh

³

et al. 2023

Preprint

0

View full text Add to dashboard Cite

Small molecule fluorescent probes that bind selectively to plant cell wall polysaccharides have been instrumental in elucidating the localization and function of these glycans. Arabinogalactan proteins (AGPs) are cell wall proteoglycans implicated in essential functions such as cell signaling, plant growth, and programmed cell death. There is currently no small molecule probe capable of fluorescently labeling AGPs. The Yariv reagents are the only small molecules that bind AGP, and have been used to study AGP function and isolate AGPs via precipitation of an AGP-Yariv complex. However, the Yariv reagents are not fluorescent, rendering them ineffective for localization studies using fluorescence microscopy. A fluorescent version of a Yariv reagent that is capable of both binding as well as imaging AGPs would provide a powerful tool for studying AGPs in planta. Herein, we describe the synthesis of an azido analog of the Yariv reagent that can be further functionalized with a fluorophore to provide a glycoconjugate that binds AGP and is fluorescent. We show that the modified reagent binds gum arabic in in vitro binding assays when used in conjunction with the βGlcYariv reagent. Fluorescent imaging of AGP in fixed maize leaf tissue enables localization of AGP to cell walls in the leaf. Significantly, imaging can also be carried out using fresh tissue. This represents the first small molecule probe that can be used to visualize AGP using fluorescence microscopy.

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A novel arabinogalactan extracted from Epiphyllum oxypetalum (DC.) Haw improves the immunity and gut microbiota in cyclophosphamide‐induced immunosuppressed mice

Dai,

Zhou,

Chen

et al. 2024

eFood

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A novel type I arabinogalactan (AG‐I) polysaccharide (EPS) from Epiphyllum oxypetalum (DC.) Haw's flowers is hypothesized to possess immunomodulatory activity. This study investigated EPS's effects on immune functions and its potential mechanism for enhancing intestinal health in immunosuppressed mice. The results showed that supplementing EPS significantly alleviated immune organ damage, increased the thymus index (p < 0.01), and regulated the key immune factors, including the tumor necrosis factor‐alpha (TNF‐α), immunoglobulin A (IgA), and complement 3 (C3) in the liver (p < 0.05). EPS promoted the expression of intestinal immune barrier and chemical barrier proteins such as interferon‐γ (IFN‐γ) and mucin 2 (MUC2) (p < 0.05), effectively repairing intestinal damage. EPS improved the diversity and structure of intestinal microbiota in immunosuppressed mice (p < 0.05) and significantly altered the abundance of intestinal immune‐related microbial taxa, including Lactobacillaceae and Lactobacillus (p < 0.01). Furthermore, EPS supplementation altered intestinal lactic acid metabolism, significantly increasing lactic acid levels by up to 3.4‐fold (p < 0.01), and enhanced the expression of Gpr81, Wnt3a, and β‐catenin proteins at the bottom of the colonic crypts, which may repair the intestinal physical barrier. Overall, EPS represents a novel AG‐I immunomodulatory dietary polysaccharide that enhances immunity and improves gut health.

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Plants arabinogalactans: From structures to physico-chemical and biological properties

Cited by 35 publications

References 219 publications

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

A novel arabinogalactan extracted from Epiphyllum oxypetalum (DC.) Haw improves the immunity and gut microbiota in cyclophosphamide‐induced immunosuppressed mice

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