Structural characterisation of novel lichen heteroglycans by NMR spectroscopy and methylation analysis

Sesseja Omarsdottir; Bent O. Petersen; Berit Smestad Paulsen; Adiaratou Togola; Jens Øllgaard Duus; Elin S. Olafsdottir

doi:10.1016/j.carres.2006.06.026

Structural characterisation of novel lichen heteroglycans by NMR spectroscopy and methylation analysis

Sesseja Omarsdottir
, Bent O. Petersen
, Berit Smestad Paulsen
, Adiaratou Togola
, Jens Øllgaard Duus
, Elin S. Olafsdottir

Department of Chemistry

Carlsberg Research Center
University of Iceland
University of Oslo

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Two galactofuranomannans, Ths-4 and Ths-5, were isolated from the lichen, Thamnolia vermicularis var. subuliformis, using ethanol fractionation and anion-exchange and size-exclusion chromatography. The average molecular weights of Ths-4 and Ths-5 were estimated to be 19 and 200 kDa, respectively. Structural characterisation of Ths-4, Ths-5 and their partially hydrolysed derivatives was performed by methanolysis and methylation analysis. The intact and partially hydrolysed Ths-4 was further analysed using NMR spectroscopy (1D, COSY, NOESY, TOCSY, HSQC and HMBC). According to the data obtained, the heteroglycans Ths-4 and Ths-5 have similar structures, but have large differences in molecular weight. The structure is composed of 3-O-linked and 5-O-linked galactofuranosyl chains linked to a mannan core. The mannan core consists of a main chain of alpha-(1 -> 6)-linked mannopyranosyl residues, substituted at O-2 with either a single alpha-mannopyranosyl unit or an alpha-Manp-(1 -> 2)-alpha-Manp-(1 -> 2)-alpha-Manp group in the ratio of approximately 1:3, respectively. The polysaccharides have idealised repeating blocks as is shown. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Journal	Carbohydrate Research
Volume	341
Issue number	14
Pages (from-to)	2449-2455
Number of pages	7
ISSN	0008-6215
DOIs	https://doi.org/10.1016/j.carres.2006.06.026
Publication status	Published - 2006

Keywords

Chromatography, Ion Exchange
Glucans
Lichens
Magnetic Resonance Spectroscopy
Methylation
Plant Preparations
Polysaccharides
Ethanol
Fractionation
Ion exchange
Molecular weight
Nuclear magnetic resonance spectroscopy
Size exclusion chromatography
alcohol
glycan derivative
anion exchange
article
chemical reaction
chemical structure
gel permeation chromatography
high performance liquid chromatography
hydrolysis
methanolysis
methylation
molecular weight
nuclear magnetic resonance spectroscopy
nuclear Overhauser effect
phase separation
plant
priority journal
reaction analysis
structure analysis
substitution reaction
thamnolia vermicularis
Thamnolia
Thamnolia vermicularis
Galactofuranomannan
Methylation analysis
NMR spectroscopy
X
BIOCHEMISTRY
CHEMISTRY,
NUCLEAR MAGNETIC-RESONANCE
CELL-WALL POLYSACCHARIDES
SUBULIFORMIS
SEPARATION
lichens
galactofuranomannan
methylation analysis
Plantae (Nonvascular Plants, Plants) - Lichenes [19000] Thamnolia vermicularis var. subuliformis variety
alpha(-1-6)-linked mannopyranosyl residue
galactofuranosyl chain
lichen heteroglycan
Ths-4
Ths-5
10060, Biochemistry studies - General
10062, Biochemistry studies - Nucleic acids, purines and pyrimidines
51522, Plant physiology - Chemical constituents
anion-exchange chromatography laboratory techniques, chromatographic techniques
ethanol fractionation laboratory techniques
methylation analysis laboratory techniques, genetic techniques
NMR laboratory techniques, spectrum analysis techniques
NMR spectroscopy laboratory techniques, spectrum analysis techniques
size-exclusion chromatography laboratory techniques, chromatographic techniques
Biochemistry and Molecular Biophysics
Methods and Techniques

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@article{34434d218a46497c824e49aed2ab1ead,

title = "Structural characterisation of novel lichen heteroglycans by NMR spectroscopy and methylation analysis",

abstract = "Two galactofuranomannans, Ths-4 and Ths-5, were isolated from the lichen, Thamnolia vermicularis var. subuliformis, using ethanol fractionation and anion-exchange and size-exclusion chromatography. The average molecular weights of Ths-4 and Ths-5 were estimated to be 19 and 200 kDa, respectively. Structural characterisation of Ths-4, Ths-5 and their partially hydrolysed derivatives was performed by methanolysis and methylation analysis. The intact and partially hydrolysed Ths-4 was further analysed using NMR spectroscopy (1D, COSY, NOESY, TOCSY, HSQC and HMBC). According to the data obtained, the heteroglycans Ths-4 and Ths-5 have similar structures, but have large differences in molecular weight. The structure is composed of 3-O-linked and 5-O-linked galactofuranosyl chains linked to a mannan core. The mannan core consists of a main chain of alpha-(1 -> 6)-linked mannopyranosyl residues, substituted at O-2 with either a single alpha-mannopyranosyl unit or an alpha-Manp-(1 -> 2)-alpha-Manp-(1 -> 2)-alpha-Manp group in the ratio of approximately 1:3, respectively. The polysaccharides have idealised repeating blocks as is shown. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "Chromatography, Ion Exchange, Glucans, Lichens, Magnetic Resonance Spectroscopy, Methylation, Plant Preparations, Polysaccharides, Ethanol, Fractionation, Ion exchange, Molecular weight, Nuclear magnetic resonance spectroscopy, Size exclusion chromatography, alcohol, glycan derivative, anion exchange, article, chemical reaction, chemical structure, gel permeation chromatography, high performance liquid chromatography, hydrolysis, methanolysis, methylation, molecular weight, nuclear magnetic resonance spectroscopy, nuclear Overhauser effect, phase separation, plant, priority journal, reaction analysis, structure analysis, substitution reaction, thamnolia vermicularis, Thamnolia, Thamnolia vermicularis, Galactofuranomannan, Methylation analysis, NMR spectroscopy, X, BIOCHEMISTRY, CHEMISTRY,, NUCLEAR MAGNETIC-RESONANCE, CELL-WALL POLYSACCHARIDES, SUBULIFORMIS, SEPARATION, lichens, galactofuranomannan, methylation analysis, Plantae (Nonvascular Plants, Plants) - Lichenes [19000] Thamnolia vermicularis var. subuliformis variety, alpha(-1-6)-linked mannopyranosyl residue, galactofuranosyl chain, lichen heteroglycan, Ths-4, Ths-5, 10060, Biochemistry studies - General, 10062, Biochemistry studies - Nucleic acids, purines and pyrimidines, 51522, Plant physiology - Chemical constituents, anion-exchange chromatography laboratory techniques, chromatographic techniques, ethanol fractionation laboratory techniques, methylation analysis laboratory techniques, genetic techniques, NMR laboratory techniques, spectrum analysis techniques, NMR spectroscopy laboratory techniques, spectrum analysis techniques, size-exclusion chromatography laboratory techniques, chromatographic techniques, Biochemistry and Molecular Biophysics, Methods and Techniques",

author = "Sesseja Omarsdottir and Petersen, \{Bent O.\} and Paulsen, \{Berit Smestad\} and Adiaratou Togola and Duus, \{Jens {\O}llgaard\} and Olafsdottir, \{Elin S.\}",

year = "2006",

doi = "10.1016/j.carres.2006.06.026",

language = "English",

volume = "341",

pages = "2449--2455",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "14",

}

TY - JOUR

T1 - Structural characterisation of novel lichen heteroglycans by NMR spectroscopy and methylation analysis

AU - Omarsdottir, Sesseja

AU - Petersen, Bent O.

AU - Paulsen, Berit Smestad

AU - Togola, Adiaratou

AU - Duus, Jens Øllgaard

AU - Olafsdottir, Elin S.

PY - 2006

Y1 - 2006

N2 - Two galactofuranomannans, Ths-4 and Ths-5, were isolated from the lichen, Thamnolia vermicularis var. subuliformis, using ethanol fractionation and anion-exchange and size-exclusion chromatography. The average molecular weights of Ths-4 and Ths-5 were estimated to be 19 and 200 kDa, respectively. Structural characterisation of Ths-4, Ths-5 and their partially hydrolysed derivatives was performed by methanolysis and methylation analysis. The intact and partially hydrolysed Ths-4 was further analysed using NMR spectroscopy (1D, COSY, NOESY, TOCSY, HSQC and HMBC). According to the data obtained, the heteroglycans Ths-4 and Ths-5 have similar structures, but have large differences in molecular weight. The structure is composed of 3-O-linked and 5-O-linked galactofuranosyl chains linked to a mannan core. The mannan core consists of a main chain of alpha-(1 -> 6)-linked mannopyranosyl residues, substituted at O-2 with either a single alpha-mannopyranosyl unit or an alpha-Manp-(1 -> 2)-alpha-Manp-(1 -> 2)-alpha-Manp group in the ratio of approximately 1:3, respectively. The polysaccharides have idealised repeating blocks as is shown. (c) 2006 Elsevier Ltd. All rights reserved.

AB - Two galactofuranomannans, Ths-4 and Ths-5, were isolated from the lichen, Thamnolia vermicularis var. subuliformis, using ethanol fractionation and anion-exchange and size-exclusion chromatography. The average molecular weights of Ths-4 and Ths-5 were estimated to be 19 and 200 kDa, respectively. Structural characterisation of Ths-4, Ths-5 and their partially hydrolysed derivatives was performed by methanolysis and methylation analysis. The intact and partially hydrolysed Ths-4 was further analysed using NMR spectroscopy (1D, COSY, NOESY, TOCSY, HSQC and HMBC). According to the data obtained, the heteroglycans Ths-4 and Ths-5 have similar structures, but have large differences in molecular weight. The structure is composed of 3-O-linked and 5-O-linked galactofuranosyl chains linked to a mannan core. The mannan core consists of a main chain of alpha-(1 -> 6)-linked mannopyranosyl residues, substituted at O-2 with either a single alpha-mannopyranosyl unit or an alpha-Manp-(1 -> 2)-alpha-Manp-(1 -> 2)-alpha-Manp group in the ratio of approximately 1:3, respectively. The polysaccharides have idealised repeating blocks as is shown. (c) 2006 Elsevier Ltd. All rights reserved.

KW - Chromatography, Ion Exchange

KW - Glucans

KW - Lichens

KW - Magnetic Resonance Spectroscopy

KW - Methylation

KW - Plant Preparations

KW - Polysaccharides

KW - Ethanol

KW - Fractionation

KW - Ion exchange

KW - Molecular weight

KW - Nuclear magnetic resonance spectroscopy

KW - Size exclusion chromatography

KW - alcohol

KW - glycan derivative

KW - anion exchange

KW - article

KW - chemical reaction

KW - chemical structure

KW - gel permeation chromatography

KW - high performance liquid chromatography

KW - hydrolysis

KW - methanolysis

KW - methylation

KW - molecular weight

KW - nuclear magnetic resonance spectroscopy

KW - nuclear Overhauser effect

KW - phase separation

KW - plant

KW - priority journal

KW - reaction analysis

KW - structure analysis

KW - substitution reaction

KW - thamnolia vermicularis

KW - Thamnolia

KW - Thamnolia vermicularis

KW - Galactofuranomannan

KW - Methylation analysis

KW - NMR spectroscopy

KW - X

KW - BIOCHEMISTRY

KW - CHEMISTRY,

KW - NUCLEAR MAGNETIC-RESONANCE

KW - CELL-WALL POLYSACCHARIDES

KW - SUBULIFORMIS

KW - SEPARATION

KW - lichens

KW - galactofuranomannan

KW - methylation analysis

KW - Plantae (Nonvascular Plants, Plants) - Lichenes [19000] Thamnolia vermicularis var. subuliformis variety

KW - alpha(-1-6)-linked mannopyranosyl residue

KW - galactofuranosyl chain

KW - lichen heteroglycan

KW - Ths-4

KW - Ths-5

KW - 10060, Biochemistry studies - General

KW - 10062, Biochemistry studies - Nucleic acids, purines and pyrimidines

KW - 51522, Plant physiology - Chemical constituents

KW - anion-exchange chromatography laboratory techniques, chromatographic techniques

KW - ethanol fractionation laboratory techniques

KW - methylation analysis laboratory techniques, genetic techniques

KW - NMR laboratory techniques, spectrum analysis techniques

KW - NMR spectroscopy laboratory techniques, spectrum analysis techniques

KW - size-exclusion chromatography laboratory techniques, chromatographic techniques

KW - Biochemistry and Molecular Biophysics

KW - Methods and Techniques

U2 - 10.1016/j.carres.2006.06.026

DO - 10.1016/j.carres.2006.06.026

M3 - Journal article

C2 - 16884705

SN - 0008-6215

VL - 341

SP - 2449

EP - 2455

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 14

ER -

Structural characterisation of novel lichen heteroglycans by NMR spectroscopy and methylation analysis

Abstract

Keywords

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