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研 究 報 文伝統的手すき紙製造で用いられる粘質物質の分析
韓江前
森林総合研究所 石井東京大学 大学院農学生命科学研究科

允魍，柳澤
敏晴，磯貝
忠

正弘
明

Analyses of Mucilaginous Compounds Used in Making
Traditional Handmade Paper
Yoon―Hee Han, Masahiro Yanagisawa,
Toshiharu Enomae and Akira Isogai
Graduate School of Agricultural andLife Science, The University of Tokyo

Tadashi Ishii
Forestry and Forest Products
Research Institute

韓 允魍

柳澤正弘

磯貝 明

石井 忠

江前敏晴

In the case of making Japanese and Korean traditional handmade paper, mucilaginous com，Hydrangae paniculata（Noriutsugi）
pounds extracted from roots of Abelmoschus manihot（Tororo―aoi）
and others with water are added to bast fiber suspensions to improve dispersity of the fibers. Although many studies in terms of chemical structures of mucilaginous compounds and their properties
in aqueous solutions have been reported, there are still many unclear research subjects.
In this study, three mucilaginous compounds extracted from roots of Japanese and Korean Abelmoschus manihot（JAM and KAM, respectively）and Japanese Hydrangae paniculata（JHP）are subjected to several chemical analyses to distinguish these compounds. Neutral sugar and uronic acidcomposition analysis clearly gave different results among the three mucilage samples. The major
metal elements were sodium and calcium for the JAM and JHP samples, while that was potassium for
the KAM sample. The three mucilage samples were distinguishable by their pyrolysis―GC patterns
obtained by the on―line methylation method. Size exclusion chromatographic analysis attached with a
２
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允魍，柳澤正弘，江前敏晴，磯貝

明，石井

忠

１M NaCl remulti―angle laser light scattering detector（SEC―MALS）of the mucilage solutions in０．
vealed some differences in molecular mass values and conformations in the solutions among the polysaccharide components in the three mucilage samples. The JAM and KAM samples had similar
５
０
０，
０
０
０，
and the JAM and JHP samples
weight average molecular mass values around２，
３
０
０，
０
０
０―２，
had similar random―coil molecular conformations. However, it is unknown at this moment whether or
not the obtained differences are applicable to all Japanese and Korean mucilaginous compounds extracted from plant roots of the same species.
Keywords：mucilage, tororo―aoi, SEC―MALS, FT―IR, sugar composition, pyrolysis―GC
分類：Y５ 高分子化学，W４ サイズ剤，S０ その他
the plant roots of even the same species, and others.

１． Introduction

Generally, uronic acid units in polysaccharides have

When Japanese and Korean traditional handmade pa-

clearly high resistances to acid hydrolysis, and thus

pers are made by craftsmen, mucilaginous com-sugar compositions of polyuronic acids determined bypounds extracted from roots of Abelmoschus manihotacid hydrolysis are difficult to evaluate quantita-，Hydrangea paniculata（Noriutsugi），Ul（Tororo―aoi）

tively；some glycoside bonds of uronic acid units still

mus japonica（Nire）and others with water are added

remain without hydrolysis in the hydrolyzates, thus

to bast fiber suspensions to improve dispersity of theresulting in inaccurate sugar composition data. Thus,

fibers. Moreover, it is well known that the mucilage

until now no consistent conclusions concerning chemi-

addition leads to smooth separation of each handmade

cal structures of mucilaginous compounds have been

sheet from piles of wet sheets. The mucilage ex-established yet, and there are still many unsolved re-tracted from root of Abelmoschus manihot in Japanese

search subjects in this field. Because more than２０

and Korean traditional handmade―papermaking has

years have past since the last paper concerning

been used since the middle of１
９th century, and somechemical structures of mucilaginous compounds wasother plant mucilaginous compounds had been usedpublished, it is worthy to re―examine the chemical

before that time.

structures of the mucilaginous compounds by using

Many fundamental researches concerning the rela-

new analytical tools.

tionships between chemical structures of the muci-

In this study, mucilaginous compounds were ex-laginous compounds and their functions in the hand-

tracted from roots of Japanese and Korean Abel-made―papermaking have already reported１―１６）．The

moschus manihot（Tororo―aoi）and Hydrangea paniculata

main components in the mucilaginous compounds（Noriutsugi）by water, and these three mucilage sam-having the characteristic roles in handmade―paper-

ples were subjected to the following analyses；neu-making are polyuronic acids having specific thread―tral sugar and uronic acid compositions, metal ele-

forming properties in aqueous solutions. Neutral

ment compositions, ash contents, FT―IR spectroscopy,

sugar and uronic acid compositions of the polysaccha-

X―ray diffactometry, pyrolysis―gas chromatographyrides after purification processes have been analyzed,

with or without the on―line methylation using te-

and rhamnose, arabinose, xylose, galactose, glucose,tramethylammonium hydroxide, and size exclusion

galacturonic acid, glucuronic acid and others seem tochromatography attached with a multi―angle laser

be present in the polysaccharides, although theirlight scattering detector（SEC―MALS）of mucilage so-weight ratios and the sugar compositions themselves

lutions. SEC―MALS analysis of polysaccharide compo-

were remarkably different among the reports１―７）．

nents in the mucilage samples can provide informa-

These differences might be caused by different purifi-tion about their molecular mass values and molecular

cation processes of the polysaccharide components inconformations. It was expected that these analyses

the mucilaginous compounds, different analyticalgave some information concerning the different poly-methods, different locations or seasons in samplingsaccharide structures among the three mucilage sam-

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伝統的手すき紙製造で用いられる粘質物質の分析

ples used.

／methatetramethylammonium hydroxide（TMAH）
nol were directly analyzed by the gas chromatograph

２． Experimental

２５mm×３０m, GL
having a capillary TC―１column（０．

２．
１ Materials

Sciences, Japan），whose initial temperature, final tem-Root samples of Abelmoschus manihot（Tororo―aoi）har-perature and program rate were set at１
５
０℃，
３
０
０℃

vested in October in Ibaraki, Japan and in Gangwondo,

and５℃／min, respectively. Py―GC patterns obtained

Korea, and that of Hydrangea paniculata（Noriutsugi）

were compared with those of birch wood meal, birch

harvested in October in Hokkaido, Japan were stored

holocellulose, cellouronic acid and apple pectin.

at４℃ before use. These roots were beaten with a

About１g of a sample was pressed to pellet form

hummer, and soaked in de―ionized water at room

using an apparatus for preparing KBr pellets in IR

temperature for one day to extract mucilaginous com-measurements, and relative weight ratios of elements

pounds. The viscous solution was filtered through aheavier than sodium in the sample were measured byfilter paper, and the filtrate thus obtained was concen-means of an X―ray fluorescence analyzer using an at-

trated by evaporation under reduced pressure below

tached determination program（MESA５０
０，
Horiba４
０℃ followed by freeze―drying. These dried mucilage

５kV and５００Co., Japan），where X―ray generated at１

samples were subjected to the following analyses. Cel-μA was irradiated on the sample for１
００s in vac-

４―linked polyglucuronic acid solouronic acid（β―１，

uum２０）．

dium salt）prepared from commercial rayon by the
１
７）

TEMPO―mediated oxidation

were used as a refer-ence.

Neutral sugar compositions of the samples were determined by the conventional alditol acetate／capillaryGC

method

after

acid

hydrolysis

with ２ M

trifluoroacetic acid at１
２
１℃ for１h２１―２３）．Neutral sugar

２．
２ SEC―MALS analysis
SEC elution patterns and the corresponding molecu-

and uronic acid compositions of the samples were de-lar mass plots of the samples were determined by thetermined by the trimethylsililation／capillary GC

１M NaCl solution was used
SEC―MALS method. A０．

method after methanolysis with１M HCl／methanol atas the eluent. Details of the SEC―MALS system used

８０℃ for１
５h２１―２３）．

were described in the previous paper１８）．The SEC col-Ash content of the samples was determined by theumn consisted of polyhydroxymethacrylate―based gel

combustion method according to ISO２
１
４
４（１
９
９
７）
．

０
６M；Shodex, Japan）．Data acquisition（OHpak SB―８

About１g of a sample was set in a crucible, and incin-

and processing were carried out using the ASTRA

erated at９００℃ for１h in the presence of air, using ansoftware（Wyatt Technologies）．SEC conditions were

electric muffle furnace（EYELA TMF２
０
０
０）
．

，
as follows：the sample concentration of０．
１％（w／V）

FT―IR spectra of the samples were recorded on a

injection volume of１００μL, flow rate of０．
５mL／minNicolet Magna８
６０by the KBr disk technique. X―rayand the column temperature of４０℃. The detector

diffraction patterns of the sample pellets（ca．
０．
１g）

cells of MALS and RI were kept at ambient tempera-

were obtained by the reflection mode using a Rigaku

ture. The mucilaginous samples were first dissolved

０
RINT２
０
０
０with monochromatic CuKα radiation at４in de―ionized water, and then the solutions were ad-kV and４
０mA.

justed to０．
１M NaCl by adding designed amounts of
１
４
９ml ／g
NaCl to the solutions. The dn／dc value of０．
obtained for carboxymethyl cellulose was applied to

３． Results and discussion
３．
１ Sugar and metal element composition analyses

the mucilaginous compounds for convenience.
２．
３ Other analyses

Hereafter, the mucilage samples obtained from roots

Pyrolysis―gas chromatograms（Py―GC）of the samplesof Japanese and Korean Abelmoschus manihot and

４B attached with
were recorded on a Shimadzu GC―１

Japanese Hydrangae paniculata are abbreviated to１
９）a vertical microfurnace―type pyrolzer ．The gas

JAM, KAM and JHP samples, respectively. Fig．
１

components formed from an approximately０．
５mg

shows relative neutral sugar and uronic acid composi-

sample pyrolyzed at４
５０℃ with or without１μL２
５％

tions of polysaccharides in the three mucilage samples.

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Relative sugar composition（%）

１
０
７
０

韓

允魍，柳澤正弘，江前敏晴，磯貝50

忠the KAM sample is regarded to be due to the starch

Abelmoschus manihot in Japan
Abelumoschus manihot in Korea
Hydrangea paniculata in Japan

40

明，石井

granules, polysaccharides other than starch in the
KAM sample consist of rhamnose, arabinose, galactose, xylose and galacturonic acid, and their relative

30

contents decrease in this order. On the other hand,polysaccharides in the JHP sample consisted of glu-

20

cose, galactose, rhamnose, galacturonic acid, and oth10

ers. Thus, each mucilage sample has characteristic
neutral sugar and uronic acid compositions, although

0
Rha

Ara

Xyl

Man

Gal

Glc Gal-A Glc-A

Fig．
１ Relative weight ratio of neutral sugar anduronic acid compositions of polysaccharidresin the mucilage samples.

it is not clear at this point whether these differences
are applicable to all Japanese and Korean mucilaginous compounds extracted from roots of the same
species or just applicable to the particular samples
used in this study.
The neutral sugar and uronic acid compositions of
the polysaccharides in the mucilage samples in Figure
１are partly or significantly different from those reported in the previous papers１―７） in terms of relative
weight ratios as well as sugar compositions themselves. These differences are primarily caused by different isolation and purification procedures of mucilage samples. In this experiment, all mucilaginous
compounds dissolved in water and filtered were subjected to the sugar composition analysis without purification, because all these extracted compounds must
more or less contribute to their characteristic func-

Photo．
１ Optical microphotograph of the mucilage／water solution obtained from root of Abelmoschus manihot in Korea.

tions in the traditional handmade―papermaking.
Fig．
２shows relative weight ratios of metal elements in the three mucilage samples. The major
metal components present in the two JAM and JHP

The JAM sample consisted of rhamnose, galacturonic

samples were sodium and calcium, while those of theacid and glucuronic acid with approximate weight ra100

samples had about４
０％ glucose. However, in the caseof the KAM sample, starch granules were clearly observed in its aqueous solution by optical microscopy
with cross polarizers（Photo.１），and thus most of glucose component present in this KAM sample（Fig．
１）
might be due to starch. These starch granules present
in the aqueous KAM solution extracted must have

Relative weight ratio（%）

tio of３：２：１．On the other hand, the KAM and JHP

passed through the filter paper during the isolationin the polysaccharides. When the glucose content in

60
40
20

Na

served in aqueous solutions of the JAM or JHP samtively large quantity as one of the sugar compositions

80

0

process. In contrast, no such starch granules were obple；the JHP sample must contain glucose in rela-Abelmoschus manihot in Japan
Abelmoschus manihot in Korea
Hydrangea paniculata in Japan

K

Ca

Mg

Fe

Zn

Mn

Metal element

Fig．
２ Relative weight ratio of metal elements in the
mucilage samples. Determined by the X―rayfluorescence analysis.

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伝統的手すき紙製造で用いられる粘質物質の分析

１
０
７
１

KAM sample were potassium, calcium and magne-

band is overlapped with that of HOH bending vibra-

sium. Especially, the high potassium content of thetion of water molecules adsorbed on the samples,

KAM sample is quite characteristic. Most of thesequantitative evaluation is difficult as long as complete

metal elements must be present in the samples as

drying of the original and KBr disk samples for FT―IR

counter ions of uronic acid residues of the mucilagi-

analysis cannot be achieved. The shoulder absorption

nous polysaccharides. Ash contents of the JAM, KAM

bands detected around１，
７
３０cm―１ in the KAM andand JHP samples were３
６．
７％，
９．
６％ and２
３．
２％，re-JHP samples indicate the presence of ester bonds, i.e.

spectively, and these values roughly corresponded tomethyl esters of uronic acid units and／or acetyl esters

those of relative uronic acid contents in Fig．
１，i.

attached to hydroxyl groups of the polysaccharides in

e．
４
５．
５％，
４．
６％ and９．
３％，respectively. It is possible

the mucilage samples.

that divalent calcium ions form intermolecular ionic

X―ray diffraction patterns of the three mucilagecross―linkages through uronic acid units of the poly-samples are depicted in Fig．
４．All polysaccharidesaccharides in aqueous solutions. Thus, the relatively

components in these mucilage samples can be re-low calcium content of the KAM sample may be re-garded to have non―crystalline structures. This is con-lated to lower viscosities of KAM solutions, which is

４―linked polyglucuronic
sistent with the result ofβ―１，

empirically well known in traditional handmade―pa-acid sodium, calcium and aluminum salts, which werepermaking.

prepared from regenerated cellulose by the TEMPO―
mediated oxidation１７）．Some sharp diffraction peaks

３．
２ FT―IR and X―ray analyses
FT―IR spectra of the three mucilage samples aredetected in Fig．
４are not due to polysaccharide com-shown in Fig．
３，and they had characteristic band

ponents but probably due to inorganic compounds ex-

５００cm―１．
patterns in the fingerprint region at４０
０―１，

tracted from the plant roots with water and present―１６
３０cm is due to C
The absorption band at１，
６
０
０―１，

in the samples together with the polysaccharide com-

＝O stretching vibration of carboxylate groups of, forponents. Thus, some metal ions detected in Fig．
２may

instance, uronic acid units. However, because thishave originated from the inorganic compounds present in the samples.
３．
３ Pyrolysis―GC analysis
Pyrolysis―gas chromatographic（Py―GC）analysis wasapplied to the three mucilage samples. Generally, Py―

Fig．
３ FT―IR spectra of the mucilage samples obtained from roots of Abelmoschus manihol inJapan（A）．Abelmoschus manihot in Korea（B），
and Hydrangea paniculata in Japan（C）
.
２
０
０
５年７月

Fig．
４ X―ray diffraction patterns of the mucilage
samples obtained from roots of Abelmoschus
manihot in Japan（A），Abelmoschus manihot in
Koerea（B），and Hydrangea paniculata in Japan（C）.

― 125 ―

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韓

允魍，柳澤正弘，江前敏晴，磯貝

明，石井

忠

Abelmoschus manihot. Although the origin of this peakis unknown at this point without GC／mass spectroscopic analysis, this characteristic peak may be used
for identification of mucilaginous compounds obtained
from roots of Abelmoschus manihot.
It is well known that the on―line methylation
methodusing

tetramethylammoniumhydroxide（TMAH）in Py―GC analysis increases thermal stabilities and volatilities of carboxylic compounds formedby pyrolysis１９）．Because peak intensities and numberof peaks in the Py―GC patterns are generally improved, consequently, more information can be obtained by the Py―GC analysis combined with the on―line methylation method of, especially, complicatedpolymeric compounds like wood and paper. Figure６
depicts the results of Py―GC analysis combined withthe on―line methylation using TMAH. The three mucilage samples were distinguishable by the clearlyFig．
５ Pyrolysis―gas chromatograms of the mucilage samples, birch wood meal and birch holocellulose . Measured without the on ― line
methylation.

GC analysis provides significant information to distinguish or identify organic compounds from peak positions and peak intensities in the obtained Py―GC patterns, just like fingerprint. As shown in Fig．
１，
thepolysaccharides in the mucilage samples used in the
traditional handmade―papermaking contain relatively
large amounts of rhamnose as one neutral sugar composition, differing from cellulose and hemicellulose inbast fibers. Thus, differences in Py―GC patterns
among the mucilage samples, birch wood meal andbirch holocellulose were also studied.
The Py―GC patterns obtained without the on―line
methylation are shown in Fig．
５．
The large peaks at
retention times of about１
２and２
７min are due toghost ones, and appeared in all Py―GC patterns. The

Fig．
６ Pyrolysis―gas chromatograms of the muci-

peak at about１
４min（pointed by arrows in Fig．
５）waslage samples, birch wood meal and birch holocellulose. Measured with the on―line methylation using TMAH.

found to be characteristic for the mucilage samples
obtained from roots of both Japanese and Korean― 126 ―

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伝統的手すき紙製造で用いられる粘質物質の分析

１
０
７
３

separated peaks pointed with arrows in Fig．
６，and

１M NaCl, clear
freeze―dried mucilage samples in０．

no such peaks were observed in the Py―GC pattern ofcoagulations or agglomerations were observed, andbirch wood meal or birch holocellulose. These peaks

the polysaccharide molecules in the mucilage samples

may be due to some carboxylic compounds present as

could not be separated properly according to their oc-

minor components in these mucilage samples. Thus,

cupied volumes by the SEC column. Thus, the freeze―

the Py―GC method combined with the on―line methyl-dried mucilage samples were first dissolved in water

ation allows to distinguish or identify these mucilagi-followed by adjustment to０．
１M NaCl for the SEC

nous compounds on the basis of their chromatograms.

analysis through the addition of NaCl to the solutions.

On the other hand, however, the rhamnose compo-

The obtained SEC elution patterns and their mo-

nent present in the mucilage samples could not give７．
All SEC elulecular―mass plots are depicted in Fig．

any characteristic peaks in the Py―GC patterns ob-tion patterns had peaks around the elution volume oftained under the adopted conditions.

５ml , which are close to the exclusion limit（i.e.
６．
３―６．

３．
４ SEC―MALS analysis

the void volume）．However, the molecular―mass plots

SEC―MALS analysis was applied to the mucilageof every sample decreased with increasing the elution

samples to evaluate molecular mass values of thevolume, indicating that the polysaccharide molecules

polysaccharide components and their conformationsin the mucilage samples are properly separated ac-

in aqueous solutions. The０．
１M NaCl was used as thecording to their occupied volumes by the SEC column.

eluent for the SEC analysis to eliminate the effect ofAgain it must be pointed out from the results in Fig．
１

carboxylate groups in the polysaccharides on theirand Photo．
１that some starch molecules other thanconformations. When sample solutions for the SEC

the original mucilaginous polysaccharides are present

analysis were prepared by direct dissolution of thein the KAM sample, and the following discussions con-Fig．
７ SEC elution patterns and the correponding molecular mass plots of polysaccharides in the mucilage samples dissolved in０．
１M NaCl.
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允魍，柳澤正弘，江前敏晴，磯貝

明，石井

忠

Table １ Weight and number average molecular mass values（Mw and
Mn, respectively）of polysaccharides in the mucilage samples＊

Abelmoschus manihot in Japan
Abelmoschus manihot in Korea
Hydrangea paniculata in Japan

Mw

Mn

Mw／Mn

２，
３
７
０，
０
０
０
２，
５
１
０，
０
０
０
４，
７
６
０，
０
０
０

１，
９
７
０，
０
０
０
２，
５
１
０，
０
０
０
３，
９
３
０，
０
０
０

１．
２
１．
０
１．
２

＊

Calculated by the SEC―MALS method using dn／dc of０．
１
４
９ml ／gcerning the KAM sample must be influenced more or

was found from the results in Table１that the poly-

less by the starch component.

saccharides in the mucilage samples have quite high

Weight and number average molecular mass values

molecular mass values. Some of the molecules in this（Mw and Mn, respectively）of the polysaccharide

fraction may form some super molecular structures

components calculated by the SEC―MALS method us-

owing to, for instance, intermolecular ionic cross―link-

１
４
９for convenience areing the same dn／dc value of０．

ages in aqueous solutions. Furthermore, it is charac-

listed in Table１．
Because the polysaccharides in theteristic that the average molecular mass values of thethree mucilage samples consist of different neutral

polysaccharides in the JHP sample are about twice assugar and uronic acid compositions, the absolute mo-much as those of the JAM and KAM samples（Table

lecular mass values do not make any sense. However,１）．In any cases, such quite high molecular mass val-

approximate sizes of polysaccharide molecules in theues of the polysaccharide components in the mucilage

mucilage samples dissolved in０．
１M NaCl can be

samples may consequently bring about their charac-evaluated and compared among the three samples. It

teristic functions in the traditional handmade―paper-Fig．
８ Radius―of―gyration or conformation plots of polysaccharides in the mucilage samples dissolved in０．
１M NaCl .
― 128 ―

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伝統的手すき紙製造で用いられる粘質物質の分析

making process.

the three mucilage samples. The orders of the

The molecular mass values of the JHP sample aremajor sugar components in the JAM, KAM andclearly higher than those of the other two samples at

JHP samples are rhamnose＞galacturonic acid＞

the same elution volume in the whole elution volume

glucuronic acid, glucose＞rhamnose＞arabinose

range, indicating that the polysaccharides in the JHP

and glucose＞ galactose＞rhamnose, respectively.

sample have more dense structures than those in the

The high glucose component of the KAM sample

JAM and KAM samples. Details about the conforma-is, however, mostly due to starch granules pre-tion of the polysaccharides in the mucilage samples
are further studied on the basis of their radius―of―gy-" The order of the major metal elements in theration or conformation plots in Fig．
８．Because theJAM and JHP samples is sodium＞calcium, while

polysaccharide component in the JHP sample had athat for the KAM sample is potassium≫calcium

clearly higher molecular mass value at the same radius―of―gyration than those of the other two, the for-# Clear differences in FT―IR spectra were ob-

mer polysaccharides may have some branched struc-served among the three mucilage samples,tures or intermolecular cross―linkages formed be-

whereas polysaccharides in all mucilage samples

tween uronic acid units through divalent ions. The
５
９for theslope values of the plots in Fig．
８are０．
５
６―０．

$ The three mucilage samples are distinguish-

JAM and JHP samples, indicating that the polysaccha-

able by their pyrolysis―GC patterns obtained byrides in these samples have random coil conformations in０．
１M NaCl. On the other hand, the slope% SEC―MALS analysis of the mucilage solutions

value for the KAM sample is０．
７
６，
and thus the poly-in０．
１M NaCl revealed some differences in mo-saccharides in this sample have more extended ran-

lecular mass values and conformations in the so-

dom coil conformations.

lutions among the three mucilage samples. The

sent in the sample.

＝magnesium.

had non―crystalline structures.

the on―line methylation method.

Several analytical experiments carried out in thisJAM and KAM samples have similar molecularstudy revealed clear structural differences among themass values, while the JAM and JHP samples

three mucilage samples. However, because the exam-

have similar molecular conformations in the solu-

ined sample number is limited, it is unknown at thistion.

moment whether these differences are applicable to

Acknowledgement

all Japanese and Korean mucilaginous compounds ex-

The authors wish to thank Mr. Satoshi Hasegawa, Mr.

tracted from roots of the same species or only applica-

Woo―Seong Jang and Mr. Hiroyuki Fukunishi forble to the particular samples used in this study. Fur-kindly providing the plant root samples for mucilagi-

ther studies are, therefore, required for obtaining

nous compounds.
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