全 文 ：Mycosystema
菌 物 学 报 15 November 2010, 29(6): 911-917

jwxt@im.ac.cn
ISSN1672-6472 CN11-5180Q
©2010 Institute of Microbiology, CAS, all rights reserved.






Supported by Leading Academic Discipline Project of Shanghai Municipal Education Commission (No. J50704)
*Corresponding author. E-mail: zhangjs888@yahoo.com.cn
Received: 26-08-2010, accepted: 11-11-2010

Isolation and structural characterization of a water-soluble
polysaccharide from Hericium erinaceus
ZHANG An-Qiang1 FU Li1 SUN Pei-Long1 ZHANG Jing-Song2* PAN Ying-Jie3
1College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China
2Institute of Edible Fungi, Shanghai Academy of Agricultural Sciences, Shanghai 201106, China
3College of Food Science, Shanghai Fisheries University, Shanghai 200090, China



Abstract: A novel water-soluble heteropolysaccharide termed HEPF2 was isolated from the fruiting bodies of Hericium erinaceus.
HEPF2 has a molecular weight of 1.66×104Da and is composed of fucose, galactose and glucose at a ratio of 1.00:3.69:5.42. HEPF2
also contains a small amount of 3-O-methylrhamnose. Its structural characteristics were further investigated by using combined
technologies including FT-IR, sugar and methylation analysis, partial acid hydrolysis and NMR spectroscopy. The results showed
that HEPF2 was a heteropolysaccharide chemically featured by (1→4)-linked glucosyl, (1→6)-linked glucosyl and (1→6)-linked
galactosyl residue, attached to the O-2 of main chain with terminal fucosyl residue or a minor of terminal glucosyl and galactosyl
residues. NMR spectra showed that (1→4)-linked glucosyl was β configuration, while (1→6)-linked galactosyl, (1→2,6)-linked
galactosyl together with the terminal fucosyl residue were all α configuration.
Key words: fungi, Chinese traditional herb, heteropolysaccharide, purification, structure elucidation

猴头菌水溶性多糖的分离纯化与结构表征
张安强 1 傅立 1 孙培龙 1 张劲松 2* 潘迎捷 3
1浙江工业大学生物与环境工程学院 杭州 310014
2上海农业科学院 食用菌研究所 上海 201106
3上海水产大学食品学院 上海 200090
摘 要：从猴头菌子实体中分离得到一种新型的水溶性杂多糖 HEPF2，分子量大小为 1.66×104Da，该多糖由岩藻糖、半乳
糖和葡萄糖以 1.00:3.69:5.42 比例构成，同时也含有微量的 3-O-甲基鼠李糖。进一步利用傅立叶变换红外光谱法、糖组成分
析、甲基化分析、部分酸水解法和核磁共振法等方法进行结构鉴定，检测结果表明，该杂多糖中包含 1→4、1→6 结合的葡
萄糖和 1→6 结合的半乳糖残基，连接于主链的侧链残基，包括岩藻糖残基、少数的端基葡萄糖和半乳糖残基。核磁共振法
检测结果还表明，1→4 结合葡萄糖为 β 构型，(1→6)结合半乳糖、(1→2,6)结合半乳糖和端基葡萄糖均为 α 构型。
关键词：大型真菌，传统中草药，杂多糖，纯化，结构分析
DOI:10.13346/j.mycosystema.2010.06.023
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INTRODUCTION
Hericium erinaceus is a traditional Chinese
medicinal fungus, distributed throughout China and has
been used to treat gastric ulcers, chronic gastritis and
other digestive tract-related diseases. Both the fruiting
bodies and mycelia of the fungus have been reported to
contain bioactive polysaccharides (Zhou et al. 2000). It
has been shown that the polysaccharides from H.
erinaceus exhibited various pharmacological activities,
including enhancement of immune system, antitumor,
hypoglycemic and anti-aging properties (Zhou et al.
2000; Nie & Zhu 2003). The main aim of this work is to
find an efficient route to extraction, isolation and
structure characterization of the polysaccharides from H.
erinaceus, as a contribution to better identify correlations
between structure and functionality. In this paper, we
report the isolation and structural investigation of HEPF2
(Polysaccharide from the fruiting bodies of Hericium
erinaceus) from the fruiting bodies of H. erinaceus.
1 MATERIALS AND METHODS
1.1 Materials
Fruiting bodies were purchased from Pan’an in
Zhejiang Province, China and identified by Professor Li
Tai-Hui, Guangdong Institute of Microbiology,
Guangzhou. DEAE-Sepharose Fast Flow and Sephacryl
S-100, S-200, S-300 High Resolution were purchased
from Amersham Pharmacia Biotech. Dextrans and the
monosaccharides (D-Gal, D-Ara, L-Fuc, L-Rha, D-man,
D-Xyl and D-Glc) were from Sigma. All other reagents
were of A.R. grade and were made in China. HPLC was
carried out on a Waters 2,695 HPLC system (2,695
HPLC Pump, 2,414 Refractive Index Detector). GC-MS
was carried out using a Thermo Finnigan Voyager
GC/MS with Trace 2,000 GC, and NMR spectra were
determined with a Varian INOVA 500.
1.2 Isolation and purification
The total fruiting bodies of H. erinaceus were first
exhaustively extracted with ethanol under reflux for 12h
to remove lipids. After filtration, the residue was air
dried and extracted 3 times with boiling water (2h for
each). The combined aqueous filtrate was concentrated
into one-tenth of the original volume, and 95% ethanol
was added to the aqueous filtrate until the final alcohol
concentration reached 30% to remove large molecular
compounds. Precipitated material was removed by
centrifugation (10,000r/min, 10min, 4℃), and 95%
ethanol was again added slowly to a final concentration
of 60%. The precipitate was separated and lyophilized,
which afforded HEPF60. A portion of HEPF60 was
dissolved in water and the insoluble residue was
removed by centrifugation. The supernatant was applied
to a DEAE-Sepharose Fast Flow column (XK 26 ×
100cm), and eluted with distilled water followed by 0－
2mol/L gradient of NaCl. The fractions were collected by
an auto-collector and the collected compounds were
detected by means of the phenol-sulfuric acid assay
(Zhang 1999). HEPF60-B was obtained from the 0－
2mol/L gradient NaCl fraction elute, which was further
purified by gel permeation chromatography on a column
of Sephacryl S-300 High Resolution (XK 26 × 100cm).
Eluting with water, the main fraction was collected,
dialyzed and lyophilized to get a white purified
polysaccharide (HEPF2), whose molecular weight range
was detected on a linked column SN of TSK PWXL
4000 and 3000 gel filtration columns firstly.
1.3 Determination of purity and molecular weight
Determination of the homogeneity and molecular
weight of samples was conducted by HPLC on a
combined column of TSK PWXL 4000 and 3000 gel
filtration columns, with mobile phase of 0.1mol/L
phosphate buffer solution (PBS) and 0.3mol/L NaNO3 at
pH7.0 at a flow rate of 0.6mL/min. The column was kept
at 30.0 ± 0.1℃. The linear regression was calibrated by
Dextrans (T-700, 580, 300, 110, 80, 70, 40, 9.3, 4). All
samples were prepared as 0.2% (w/v) solutions, and
10µL of solution was analyzed in each run.
1.4 Monosaccharide composition analysis
HEPF2 (2mg) was hydrolyzed with 2mol/L
trifluoroacetic acid (TFA) at 110℃ for 2h, and the
monosaccharide composition was determined by
high-performance anion-exchange chromatography
(HPAEC) using a Dionex LC30 equipped with a
CarboPacTM PA20 column (3mm × 150mm). The
column was eluted with 2mmol/L NaOH (0.45mL/min)
and the monosaccharides were monitored using a pulsed
amperometric detector (Dionex) (Yang 2005).
1.5 Methylation analysis
Vacuum dried polysaccharide (2mg) was methylated
by the Kalyan & Paul (1992) method. Complete
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methylation was confirmed by the disappearance of the
hydroxyl peak (3,200－3,700/cm) in the IR spectrum.
The permethylated product was hydrolyzed using
HCO2H (88%, 0.5mL), H2O (0.1mL) and CF3CO2H acid
(0.05mL) at 100℃ for 16h. The partially methylated
sugars in the hydrolysate were mixed with NaBH4 and
acetylated with acetic anhydride, and the resulting
mixture of alditol acetates was analyzed by GC-MS.
1.6 Partial acid hydrolysis
Oligosaccharides were produced by partial acid
hydrolysis of the polysaccharide. HEPF2 (100mg) was
hydrolyzed by 0.05mol/L CF3COOH (50mL) for 1h at
100℃. The acid was removed by co-distillation with
CH3OH. The hydrolyzate was dissolved in distilled water
(0.5mL), and dialyzed against distilled water for 24h.
The dialysate was purified by gel permeation
chromatography on a column of Sephacryl S-100 High
Resolution (XK 26 × 100cm) and lyophilized
(HEPF2dw1). The nondialysate was purified by gel
permeation chromatography on a column of Sephacryl
S-300 High Resolution (XK 26 × 100cm) and was
lyophilized to give a degraded polymer (HEPF2dn1). A
portion of HEPF2dn1 was methylated and its glycosyl
linkage composition was determined as described above.
HEPF2dn1 (30mg) was further hydrolyzed by 0.1mol/L
CF3COOH (15mL) for 1h at 100℃. After partial acid
hydrolysis of HEPF2dn1, the hydrolysate was dialyzed.
A depolymerized product (HEPF2dn2) was obtained and
separated by Sephacryl S-200 High Resolution (XK 26 ×
100cm) chromatography. The dialysate was concentrated
and lyophilized, designated HEPF2dw2. A portion of
HEPF2dn2 was methylated and its glycosyl linkage
composition was determined as described above. The
glycosyl residue compositions of HEPF2dw1,
HEPF2dn1, HEPF2dw2 and HEPF2dn2 were determined
by GC as alditol acetates (Albersheim et al. 1967) and
analyzed by GC-MS using a DB-5 column (30m ×
0.25mm × 0.25µm) at a temperature program as follows:
80℃ to 200℃ at a rate of 5℃/min, increasing to 215℃
at a rate of 2℃/min, and finally to 280℃ at a rate of
20℃/min. The injector and detector heater temperatures
were both 250℃.
1.7 NMR analysis
HEPF2 (30mg) was lyophilized and then dissolved
in D2O (0.5mL) three times to get rid of H2O. The 1H
NMR (60℃) and 13C NMR (25℃) spectra were
determined in 5mm tubes using a Varian INOVA 500
NMR spectrometer. 1H chemical shifts were referenced
to residual HDO at δ 4.34 (60℃) as internal standard.
13C chemical shifts were determined in relation to DSS
(δ 0.00) calibrated externally.
2 RESULTS
2.1 Isolation, purification and molecular weight
determination of HEPF2
HEPF2 was purified by anion-exchange (Fig. 1) and
gel filtration chromatography from the fruiting bodies of
H. erinaceus. The single symmetrical peak presented by
HPLC indicated that it was a homogeneous
polysaccharide (Fig. 2). Based on the calibration curve of
dextran standards, the molecular weight of HEPF2 was
calculated to be 1.66×104Da. The absence of absorption
at 280nm by UV scanning indicated that HEPF2
contained no protein.

Fig. 1 The elution of HEPF60 isolated from the fruiting bodies of
Hericium erinaceus by DEAE-Sepharose F.F. column chromatography.

Fig. 2 High Performance Liquid Chromatography (HPLC) elution of
HEPF2 isolated from the fruiting bodies of Hericium erinaceus.

2.2 FTIR spectroscopic characterization
The infrared spectrum of the polysaccharide was
shown in Fig. 3. The broadly stretched intense peak at
3,400/cm was due to the hydroxyl stretching vibration of
the polysaccharide. The band at 2,925.5/cm was due to
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C-H stretching of CH2 groups. The band at 1,646.9/cm
showed that the occurrence of bound water. The bands
approximately in the region of 3,400, 2,930 and
1,650/cm are characteristic of a carbohydrate ring (Li et
al. 2008). Three absorption peaks between 1,010 and
1,160/cm attributed to the stretching vibrations of
pyranose ring. Two stretching peaks at 1,161 and
1,041/cm in the IR spectrum suggested the presence of
C-O bonds (Zhao et al. 2007). No absorption peaks at
1,740/cm indicated that there were no uronic acids.
2.3 Sugar and methylation analysis
Sugar analysis and GC-MS revealed the presence of
fucose, galactose and glucose in the molar ratio of
1.00:3.69:5.42. Analysis also evidenced the presence of a
small amount of 3-O-methylrhamnose. The alditol
acetates of the methylated material from the
polysaccharide were analyzed by GC-MS using a DB-5
MS fused silica capillary column. The results showed the
presence of 1,4,5-tri-O-acetyl-2,3,6-tri-O-methyl-D-
glucitol, 1,5,6-tri-O-acetyl-2,3,4-tri-O-methyl-D-glucitol,
1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl-D-glucitol, 1,5,6-tri-
O-acetyl-2,3,4-tri-O-methyl-D-galactitol, 1,2,5,6-tetra-O-
acetyl-3,4-di-O-methyl-D-galactitol, 1,5-di-O-acetyl-2,3,
4,6-tetra-O-methyl-D-galactitol, 1,5-di-O-acetyl-2,3,4-tri-
O-methyl-L-fucitol, 1,5-di-O-acetyl-2,3,4-tri-O-methylrh
amnose in a molar ratio of 3.31:2.13:0.25:2.03:1.11:
0.21:1.00:0.19 (Table1). These results indicated that
(1→4)-linked Glcp, (1→6)-linked Glcp, (1→6)-linked
Galp, (1,2→6)-linked Galp, nonreducing-end Glcp,
nonreducing-end Galp, nonreducing-end Fucp were
present in the polysaccharide. Besides, it also contained a
minor terminal 3-O-methyl rhamnose residue.

Fig. 3 FT-IR spectrum of the polysaccharide HEPF2 isolated from the fruiting bodies of Hericium erinaceus.

Table 1 The methylation analysis of HEPF2
Methylated sugar Type of linkage Molar ratio Major mass fragment (m/z)
2,3,4-Me3-Rhap 1-linked 3-O-Me-Rhap 0.19 43,71,89,101,117,131,145,161
2,3,4-Me3-Fucp 1-linked Fucp 1.00 43,72,89,101,115,117,131,161,175
2,3,4,6-Me4-Glc 1-linked Glcp 0.25 43,71,87,101,117,129,145,161,205
2,3,6-Me4-Glcp 1,4-linked Glcp 3.31 45,71,87,101,117,129,143,161,203,233
2,3,4-Me3-Glcp 1,6-linked Glcp 2.13 43,71,87,101,117,129,161,173,189,233
2,3,4,6-Me4-Galp 1-linked Galp 0.21 43,71,87,101,117,129,145,161,205
2,3,4-Me4-Galp 1,6-linked Galp 2.03 43,87,99,101,117,129,161,173,189,233
3,4-Me2-Galp 1,2,6-linked Galp 1.11 43,71,87,99,129,159,173,189,233

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2.4 Partial acid hydrolysis
Due to the complexity of the HEPF2 structure,
partial acid hydrolysis experiment was carried out with
the polysaccharide. After partial acid hydrolysis of
HEPF2, the hydrolysate was dialyzed against the dialysis
membrane of 1×104Da and purified by gel permeation
chromatography on a column of Sephacryl S-100 High
Resolution and lyophilized to give HEPF2dw1. The
nondialysate was subjected to gel permeation
chromatography on a column of Sephacryl S-300 High
Resolution, and the elute was lyophilized to give a
degraded polymer (HEPF2dn1). HEPF2dn1 was further
hydrolyzed by 0.1mol/L CF3COOH for 1h at 100℃. The
nondialysate was subjected to gel permeation
chromatography on a column of Sephacryl S-200 High
Resolution and was lyophilized to give a degraded
polymer (HEPF2dn2). The dialysate was concentrated
and lyophilized, which resulted in the fraction termed
HEPF2dw2. HPAEC spectrum of HEPF2dw1 and
HEPF2dw2 revealed the presence of fucose, 3-O-methyl
rhamnose and a few galactose, glucose. This result
indicates that the nonreducing-end of
D-galactopyranosyl, glucopyranosyl, and fucopyranosyl
moieties were destroyed during partial acid hydrolysis.
Compositional analysis of the degraded polysaccharide
HEPF2dn1 suggested that it was composed of fucose,
galactose and glucose in a molar ratio of 0.04:1:2.34
(Table 2). The contents of fucose and 3-O-methyl
rhamnose in HEPF2dn1 decreased remarkably as compared
to those of native polysaccharide. This was in agreement
with the results of methylation analysis of HEPF2 in that
the fucosyl residues and 3-O-methyl rhamnose residues
were all the terminal residues. Compositional analysis of
the degraded polysaccharide HEPF2dn2 suggested that it
was composed of fucose, galactose and glucose in a
molar ratio of 0.07:1:4.27 (Table 2). In comparison with
the composition of the native polysaccharide, the
proportion of glucose significantly increased, while the
content of fucose and galactose decreased remarkably.
The methylation analysis of HEPF2dn2 showed the
presence of 1,4,5-tri-O-acetyl-2,3,6-tri-O-methyl-D-glucitol,
1,5,6-tri-O-acetyl-2,3,4-tri-O-methyl-D-glucitol, 1,5,6-tri-
O-acetyl-2,3,4-tri-O-methyl-D-galactitol, 1,2,5,6-tetra-O-
acetyl-3,4-di-O-methyl-D-galactitol, 1,5-di-O-acetyl-2,3,
4-tri-O-methyl-L-fucitol, in a molar ratio of 3.8:1.5:1.00:
0.25:0.13 (Table 3). In comparison with the methylation
analysis of the native polysaccharide, the proportion of
(1→6)-linked galactose and (1→2,6)-linked galactose
residues decreased, while the proportion of (1→4)-linked
and (1→6)-linked glucosyl residues significantly
increased. These results evidenced that the backbone
chain of the HEPF2 was composed of 1,4 and 1,6 linked
glucosyl residue and 1,6 and 1,2,6 linked galactosyl
residues, with terminal fucosyl residue or a minor of
terminal glucosyl and galactosyl residues.

Table 2 Glycosyl composition of HEPF2 and its partial acid
hydrolysates
Molar ratio
Glycosyl residues
HEPF2 HEPF2dw1 HEPF2dn1 HEPF2dw2 HEPF2dn2
3-O-methyl-
rhamnose
0.28 1.00 0.01 1.00 n.d.a
Fucose 1.00 6.17 0.04 6.26 0.07
Galactose 3.69 1.25 1.00 3.36 1.00
Glucose 5.42 0.74 2.34 0.53 4.27
Note: anon detected. HEPF2dw1 was given from partial acid hydrolysis of
HEPF2 by gel permeation chromatography S-100. HEPF2dn1 was given
from The nondialysate by gel permeation chromatography S-300.
HEPF2dn2 was from the nondialysate of further hydrolyzing of HEPF2dn1
by gel permeation chromatography S-200. Concentrated and lyophilized the
dialysate, termed HEPF2dw2.

2.5 NMR analysis
The 1H and 13C NMR experiments were carried out
at 60℃ and 25℃ respectively. 1H NMR spectrum of
HEPF2 (Fig. 4) mainly contained signals for five
anomeric protons at δ 5.10, 5.06, 5.00, 4.74 and 4.54.
One CH3-C group at δ 1.27 (J5, 6 5.6Hz) corresponded to
the chemical shift of H-6 of Fuc. Other sugar protons
were in the region of δ 3.50－4.41 along with a signal
for an O-methyl group at δ 3.50. Sugar residues were
designated A-E according to the decreasing chemical
shifts of the anomeric configuration. Methylation
analysis showed the highest proportion of residues was
(1→4)-linked Glcp, in the 1H NMR spectrum the highest
proportion was residue E, and was thereby designated as
a (1→4)-linked Glcp. The large coupling constants
JH-2, H-3 and JH-3, H-4 (~10Hz) were observed for E, further
indicating that it was a D-glucosyl moiety. The anomeric
chemical shift of moiety E appeared as a doublet at δ
4.54 indicated that the D-glucose was β-linked.
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Fig. 4 500-MHz 1H NMR spectrum of HEPF2 isolated from the fruiting
bodies of Hericium erinaceus at 60℃. A-E were donated by the
decreasing chemical shifts of the anomeric configuration.

The other signals for anomeric protons were in the
region of δ 5.00 － 5.10, indicating 1-linked Fucp,
(1→6)-linked Galp, (1→2,6)-linked Galp were α
configuration. The 13C NMR spectrum (Fig. 5) of the
polysaccharide mainly contained signals for five
anomeric carbons at δ 106.14、106.07, 105.89, 101.4 and
101.2. Sugar ring carbons linked to oxygen in the region
of δ 63.12－80.6 and one CH3-C groups (C-6 of Fuc) at
δ 18.4. In addition, a minor signal at δ 57.5 could be
assigned to an O-methyl group, which, based on GC-MS
data, was probably contributed by 3-O-methyl-rhamnose.
The presence of β-D-(1→4)-linked Glcp was proved by
the signals at δ 80.6. The O-substituted C-6 was shown
by the signals at δ 70.05 and δ 69.9, and the signal of the
unsubstituted C-6 was at δ 64.1and δ 59.1. 4.

Fig. 5 500-MHz 13C NMR spectrum of HEPF2 isolated from the
fruiting bodies of Hericium erinaceus at 25℃. Fuc C-6: This peak was
a result of one CH3-C groups (C-6 of Fuc) at δ 18.4.
3 DISCUSSION
Polysaccharides composed of β-glucans and
α-D-manmans have been reported to be the major
components of the cell wall and the intercellular matrix,
with the latter being found mainly in yeast cell walls and
medicinal mushrooms (Vingradov et al. 1998). In
contrast, polysaccharides consisting of fucogalactan,
fucoglucogalactan (Zhang et al. 2006, 2007) and
β-glucan (Dong et al. 2006) have been found in H.
erinaceus. The biological effects of these
polysaccharides have been widely studied for their
immunostimulating and anti-tumor activities (Tokunaka
et al. 2000). However, structure of a
heteropolysaccharide composed of β-glucose, α-fucose
and α-galactose, containing diverse terminal residues has
not been previously found in the H. erinaceus. This
structure may contribute to the bioactivity presented in
the treatment of digestive tract-related diseases. But
further investigation is needed to confirm such
relationships between this structure and corresponding
functionality. The extraction, isolation and structure
characterization of HEPF2 investigated in this report
provide a theoretic background and material basis for the
further research of polysaccharides from H. erinaceus,
including the relationship between structure and
functionality.

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