Professional Documents
Culture Documents
Abstract
Wasabi, Japanese Horseradish (Wasabia japonica (Miq.) Matsum) is a perennial plant native to Japan.
It has been cultivated in Japan for more than a thousand years and is now being grown in many coun-
tries as interest in Japanese cuisine expands. Wasabi can be grown in two main ways, either in flooded
fields or in soil based mediums. The unique flavour of wasabi comes from isothiocyanates (ITCs)
which are evolved from precursor glucosinolates by the enzyme myrosinase when the tissue is disrupt-
ed. ITCs found in wasabi are volatile, possess strong pungent smells and are toxic at high intakes. The
overall flavour of wasabi depends on individual ITC content. Allyl ITC is found in the highest concen-
tration in all tissues, ranging from 86-92% of the total ITC content. Apart from flavouring sauces and
foods wasabi isothiocyanates have interesting anticancer effects. ITCs can also counter inflammatory
conditions like asthma and anaphylaxis. ITCs have also been shown to inhibit platelet aggregation in
the blood. Wasabi is a valuable crop that can be processed into a tasty condiment. Its production and
consumption will increase as it becomes more appreciated in Western cuisine.
Introduction
History
Wasabi cultivars
as it may contain insufficient oxygen, but expansion in soil grown wasabi is mainly to
some silt in the water is considered benefi- reduce the high cost of flooded field estab-
cial as a source of nutrients. In Japan, wasabi lishment and associated high labour costs.
grows on the wet banks of cool mountain
streams and springs. Overall, construction Uses of wasabi
and establish-ment of a flooded field is
Wasabi adds a unique flavour, heat and
expensive and labour intensive. Water grown
greenish colour to foods and, thus, it is a
wasabi is produced in 42 prefectures, and
highly valued plant in Japanese cuisine.
soil grown wasabi in 21, out of 47 prefec-
Wasabi is described as having 'a sharp hot
tures in Japan, which indicates that flooded
taste with pungent smell' but the heat com-
cultivation is popular and is considered to
ponent in wasabi is different from chillies,
produce a high quality product.
and the hotness quickly dissipates in the
The unique environmental requirement and mouth leaving an extremely pleasant mild
shortage of cultivatable lands limit wasabi vegetable taste, with no burning sensation at
production areas to 880 hectares in Japan all. Wasabi adds aesthetic and culinary
(Adachi, 1987) and 400 hectares in Taiwan, appeal to many foods and is considered a sta-
but demand for wasabi condiments is ple condiment in the Japanese diet. Recently,
spreading from Japanese cuisine to modern it has found widespread appeal in western
western food. The increasing interest in cuisine due to its ability to change an ordi-
wasabi and the inability to expand produc- nary dish to an extra special one by improv-
tion in Japan has seen prices rise steadily ing the taste (with addition of a spicy
since 1970 (Chadwick et al, 1993). High flavour) and eye appeal i.e. by decorative
prices have stimulated research into soil pro- contrast of the light green colour. As a
duction methods and the investigation of result, it is becoming a new flavour for the
production areas outside Japan. Since 1982, rest of the world.
the cultivation of wasabi has been trialled in
All the plant parts of wasabi possess some
New Zealand (Douglas and Follett, 1992)
flavour but vary in the sharpness they deliv-
because of New Zealand's climate (appropri-
er (Sultana et al, 2000; Sultana et al, 2003c)
ate air temperature range, high quality water,
and are, therefore, used for different purpos-
long sunlight hours), which meets the ideal
es. Basically, wasabi can be served in three
requirements for growing quality wasabi
ways. These are as a condiment on the side
outside Japan. However, the area of soil
of a dish, as a spice or herb in a dish and as
grown wasabi is increasing not only in New
wasabi flavour in processed foods.
Zealand but also in Taiwan, Colombia,
Rhizomes are the most popular tissues used
Canada, Korea, Thailand and USA. The
to prepare fresh paste to be placed in a
438 Wasabi - Japanese Horseradish 43(4) 2008
GSLs are a group of glucosides, stored with- occur in nature in the anionic form (Larsen,
in the cell vacuoles of all Crucifereae plants 1981) and usually as the potassium or sodi-
(Delaquis and Mazza, 1995). GSLs are um salt (Warton et al, 2001). Due to the pres-
biosynthesised from amino acids by three ence of the glucose moiety they are
major steps (Sultana et al, 2000). The GSLs hydrophilic, non volatile compounds
consist of a ß-D thioglucose moiety, a sul- (Larsen, 1981).
phate attached through a C=N bond and a
side group (R) that distinguishes one GSL When plant tissues are mechanically disrupt-
from another (Fig. 2). Based on the structure ed or injured (eg. by chewing, crushing or
of different amino acid precursors a wide grating in the preparation of food), the
variety of side groups (R) produce different myrosinase is released from the cell wall and
GSLs (aliphatic, aromatic, indolyl types) in the presence of adequate moisture myrosi-
and, therefore, different ITCs. Due to the nase rapidly hydrolyses the GSLs (Fig. 3) to
low pKa value (Prestera et al, 1996) of the yield glucose and an aglucone. Some of the
sulphonic acid group GSLs invariably intermediate steps have not been fully
C O2
[O]
1. R CH COOH R CH COOH R CH
N H2 NHOH NOH
O H
Cysteine UDP-glucose UDP
OH
S
OH H
2. Aldoxime R C SH R C
Through
intermediate NOH NOH
steps
Thiohydroxamicacid Desulfoglucosinolate
C H2O H
PAPS O H
PAP
OH
S
3. Desulfoglucosinilate R C OH H
N O S O3-
Glucosinolate
described (Fahey et al, 2001; McGregor, vents. Most of the sulphur containing end
1993). The organic aglucone is unstable and products formed by the enzymatic and non-
undergoes Lossen Rearrangement (Fenwick enzymatic reactions of GSLs are volatile
et al,1983) to produce sulphate and a variety (Delaquis and Mazza, 1995).
of other products.
Several ITCs have been reported from previ-
The nature of the products is dependent on ous investigations into wasabi and each ITC
the number of factors, including the structure has a specific flavour profile (Sultana et al,
of the GSL side chain, the reaction condi- 2000; Masuda et al, 1996) with the complete
tions (eg. pH), the presence of cofactors (eg. taste of wasabi being derived from the com-
metal ions, specific proteins), temperature bined tastes and odours of all the ITCs pres-
and duration as well as the age and condition ent. A summary of different ITCs reported
of the plant tissues. Isothiocyanates (ITCs) from previous investigations into the ITC
are formed from GSLs under neutral and content of wasabi tissue is listed in Table I.
alkaline conditions. However, GSLs that
contain a ß-hydroxyl group (I. in Fig. 3) in Allyl ITC has the main effect on the overall
their side chain, give rise to ITCs that spon- taste of wasabi because it is the ITC found in
taneously cyclize to form oxazo- highest concentration in the rhizomes and
lidinethiones. Some aromatic and hetero- other plant tissues (Sultana et al, 2002).
cyclic GSLs (II in Fig. 3) produce ITCs Allyl ITC is also found in the highest con-
which are unstable at pH 7 or higher and centration in horseradish (Sultana et al,
break down to release the corresponding 2003c). While allyl ITC is the main flavour
alcohol and inorganic thiocyanate ions. component of wasabi due to its pungency
other ITCs e.g. 6-methylthiohexyl ITC and
However, once formed, ITCs are more sta- 7-methylthioheptyl ITC, by giving their
ble under acidic conditions. In weakly acidic characteristic fresh greenish flavour, may
pH or in the presence of Fe+2 and/or endoge- contribute significantly to the total taste pro-
nous nitrile factor, nitriles are produced from file of wasabi (Masuda et al, 1996; Ina et al,
aglucone by autolysis instead of ITC, with 1981).
the liberation of elemental sulphur
Medicinal properties of isothiocyanates
(McGregor,1993). The relative pro-portion
of ITC to nitriles can vary widely depending The medicinal value of chemicals extracted
upon the conditions of autolysis from wasabi were first docu-mented in the
(McGregor,1993). Thiocyanate formation is Japanese medicinal encyclo-paedia during
believed to involve a cofactor, which may the 10th century (Ina et al, 1981). Recently,
also be a protein, since it has been shown to research interest in ITCs has become more
be labile to both heat and polar organic sol-
Sultana and Savage 441
C H2O H
o H IfsidegroupR(inglucosinolate)becomesI,IIthenproducts
OH C H2 NH
S
OHH CH
C H2 CHCHCH
2 C H2 CH C S
R C
OH O
N O S O3-
I) 2-Hydroxy-2-butenyl
5-vinyloxazolidine-2-thione
Glucosinolate
H2O
HO C H2 HO C H2O H + S C N-
Enzyme
Myrosinase
II)4-hydroxybenzyl 4-Hydroxybenzylalcohol
C H2O H
H O H
OH
OH H
S D-Glucose
R C
N O S O3-
UnstableAglucone
pH 7 R N C S + SO 4 -
Isothiocyanate (ITC)
Autolysis
pH 3-6
Fe++ or
Nitrile
factor R C N + S + S O4--
Non
enzymic Nitrile
reaction
H2C C H C H2 C N + S O4--
S
Epithionitrile
R S C N + S O4--
Thiocyanate
Fig. 3: Conversion of glucosinolates to different products by enzymic and nonenzymic reac-
tions (Sultana et al, 2000)
intense because of their potential to have a applications are at an early stage of investi-
wide variety of medicinal, pharmacological gation, most likely because of wasabi's high
or industrial applications. These exciting present commercial value and scarcity.
442 Wasabi - Japanese Horseradish 43(4) 2008
Table I. Isothiocyanates in wasabi (mg/kg fresh weight) and a description of the odour of each
individual ITC (Sultana et al, 2000)
by arachidonic acid (Kumagai et al, 1994), ing activation) are known to cause bronchial
and for deaggregation. ITCs showed a ten obstruction and generally play a role in the
times higher response than is reported for pathogenesis of bronchial asthma. The isoth-
aspirin. In the case of heart attacks, where iocyanates prevented bronchial obstruction
aspirin is commonly prescribed, ITCs have caused by subsequent inhalation of ovalbu-
been shown to have a more rapid action at min but did not prevent obstruction caused
low levels than the thirty minutes for aspirin.
by inhalation of histamine acetylcholine.
In this regard, the most potent ITCs reported
This indicates that the anti-asthmatic effect
are ω-methylthioalkyl ITCs, especially 6-
of ITCs are not due to an anti-histamine
methylthiohexyl followed by 7-methyl-thio-
effect but act by inhibiting the inflammatory
heptyl and 5-methylthiopentyl ITCs. The
anticoagulant property of ITCs could be process at an earlier stage, possibly the pro-
used in the treatment of elderly people and duction or action of other inflammatory mol-
during surgery where preventing platelet ecules such as thromboxanes or
aggregation is vital for the well being of the prostaglandins. Thus, ITCs could potentially
patient. The mechanism by which the ITCs be used to counter inflammatory conditions
inhibit platelet aggregation from occurring such as asthma or even anaphylaxis.
has not been precisely determined but may Traditionally, horseradish and mustard have
be through a specific inhibition of the arachi- been used as a remedy for clogged sinuses,
donic acid cascade (Depree et al, 1999). relief of congestion, muscular pain and
Whereas, Morimitshu et al, (2000) reported inflamed joints (Depree et al, 1999).
that the antiplatelet role of ITC moiety is
because of its high reactivity with sulphydryl Antibiotic effect
groups in biomolecule. This therefore raises
the possibility of using ITCs to limit inflam- Masuda (2000) has suggested that wasabi
mation in tissues. could contribute to a healthy smile by
inhibiting the growth of the bacteria on teeth
Anti-asthmatic and anti-inflammatory prop- and gums in the mouth. Streptococcus
erties mutans is known to cause dental caries and
the consumption of wasabi can reduce bacte-
Benzyl and allyl ITCs from onion extracts
rial activity. This was explained by wasabi's
showed anti-asthmatic effects when studied
ability to interfere with the sucrose-depend-
by Dorsch et al. 1985. Throm-boxanes (gen-
ent adherence of cells to the surface of teeth
erated by lung tissue and by aggregating
and gums. Shin et al, (2004) reported that
platelets during lung anaphy-laxis) and
allyl ITC in roots, stems and leaves of
prostaglandins (generated by mast cells dur-
Sultana and Savage 445
wasabi showed bactericidal activities against defensin gene (Kanzaki et al, 2002). It seems
Helicobacter pylori. The bactericidal activity that there is a potential to develop a natural
of leaves found highest than that of roots fungicide using wasabi extracts. Wasabi also
though the contents of allyl ITC in leaves showed peroxidase activity (Kinae et al,
found lower than roots. Therefore, they sug- 2000) and exhibited antioxidative and super-
gested that certain bioactive compounds oxide scavenging potency. Thus wasabi
besides allyl ITC in wasabi are also effective extract may be used as natural antioxidant.
in killing H. pylori which causes stomach
Conclusions
ulcer.
Brown, P.D. Morra, MJ. (1997). Adv Agron 61: Fuke, Y. Ohishi, Y. Iwashita, K. Ono H.
167-231. Shinohara, K. 1994. J Japanese Soc Food
Sci Technol 41: 709-711 (In Japanese with
Chadwick, C.I. Lumpkin, T.A. Elberson, L.R. English summary).
(1993). Econ Bot 47: 113-135.
Hasegawa, N. Matsumoto, Y. Hoshino, A.
Chung, F.L. (2002). Chapter 7 in Phytochemicals Iwashita, K. (1999). Internat J Food
in Nutrition and Health edited by Meskin Microbiol 49: 27-34.
MS, Bidlack WR, Davies AJ and Omaye
ST, CRC Press USA. Hodge WH. (1974). Econ Bot 28: 118-129.
Delaquis, P.J. Mazza, G. (1995). Food Technol Ina K, Sano A, Nobukuni M, Kishima I. (1981).
73-84. Nippon Shokuhin Kogyo Gakkaishi 28:
365-370.
Depree, J.A. Howard, T.M. Savage, GP. (1999).
Food Res Inter 31: 329-337. Kanzaki, H. Nirasawa, S. Saitoh, H. Ito, M.
Nishihara, M. Terauchi, R. nakamura I.
Dorsch, W. Adam, O. Weber, J. Ziegeltrum, T. (2002). Theo and App Genet. 105 (6/7):
(1985). Euro J Pharmacol 107: 17-25. 809-881.
Douglas, J.A. Follett, J.M. (1992). Proc Agron Kinae, N. Masuda, H. Shin, IS. Furugori, M.
Soc 22: 57-60. Shimoi. K. (2000). Biofactors 13 (1-4):
265-269.
Etoh, H. Nishimura, A. Takasawa, R. Yagi, A.
Satio, K. Sakata, K. Kishima, I. Ina, K. Kojima M. (1981). Nogyo Oyobi Engei, 56(5):
(1990). Agric Biol Chem 54: 1578-1589. 113-118.
Fahey, J.W. Zalcmann, A.T. Talalay, P. (2001). Kumagai, H. Kashima, N. Seki, T. Sakurai, H.
Phytochem 56: 5-51. Ishii, K. Ariga T. (1994). Biosci Biotech
Biochem 58 (12): 2131-2135.
Fenwick, R. Heaney, R.K. Mullin, W.J. (1983).
CRC Crit Rev Food Sci Nutr 18: 123-201. Kumagai H, Kishima N, Seki T, Sakurai, H., Ishii
K, Ariga T. (1994). Biosci Biotechnol
Forde, B. (1982). Department of scientific and Biochem 58: 2131-2135.
Industrial research discussion paper no. 7.
Wellington, NZ, 25p. Larsen PO. 1981. Glucosinolates in the biochem-
istry of Plants. A comprehensive Teatise,
Fuke, Y. Haga, Y. Ono, H. Nomura, T. Ryoyama, Stumpf PK and Conn, EE Eds, Vol 5, pp
K. (1997). Cytotech 25: 197-203. 502-525, Academic press, N Y.
Sultana and Savage 447
Lin HJ, Probst-Hensch NM, Louie AD, Kau IH, Nakayama, H. Suzuki, T. Suzuki, Y. (1998).
Witte JS, Ingles SA, Frankl HD, Lee ER, Nippon Nogeikagaku Kaishi 72: 499-507.
Haile RW. (1998). Cancer Epid Biomark
Prev 7: 647-652. Ono, H. Tesaki, S. Tanabe, S. Watanabe, M.
(1998). Biosci Biotech Biochem 62(2):
Martin RJ, Deo B. (2000). N Z J Crop hort Sci 363-365.
28: 45-51.
Palmer, J. (1990). N Z J Crop Hort Sci 18: 161-164.
Masuda, H. Harada, Y. Tanaka, K. Nakajima, M.
Tebeta, H. Takeoka, GR. Teranishi, R. Prestera, T. Fahey, J.W. Holtzclaw, W.D.
Williams, PJ. Kobayash, IA. (1996). Abeygunawardana, C. Kalchinski, J.L.
Biotech improved foods flavours. ACS Talalay, P. (1996). Anal Biochem 239: 168-
Symposium Series No. 637 25: 67-78. 179.
Matsuda H. 2000. Sci News (159): 29. Seow, A. Shi C-Y, Jiao, D. Hankin, J.H. Lee, H-
P. Coetzee, G.A. Yu, M. (1998). Cancer
McGregor DI, Mullin WJ and Fenwick GR Epid Biomark Prev 7:775-781.
(1983). J Ass off Anal Chem 66 : 825-849.
Shin, I.S. Lee, J.M. (1998). Bull Korean Fish
McGregor DI (1993). In: Encyclopaedia of Food Soc 31: 835-841.
Science Food Technology, Nutrition,
Macrae R, Robinson RK and Sadler MJ. Shin, I.S. Masuda, H. Naohide, K. (2004). Int J
Eds, Vol 4, Academic press, Harcourt Food Microbiol 94 (3): 255-261
Brace Jovanovich publishers.
Soledade, M. Pedras, C. Sorensen, J.L. (1998).
Morimitsu, Y. Hayashi, K. Nakagawa, Y. Fujii, H. Phytochem 49: 1959-1965.
Horio, F. Uchida, K. Osawa, T. (2000).
Steinmetz, K.A. Potte, J.D. (1991). Vegetables,
Mech Ageing Dev 116 (2-3): 125-134.
fruit, and cancer. II: Mechanisms. Cancer
Morse, M.A. Amin, S.G. Hecht, S.S. Chung, F.L. Causes Control 2: 427-442.
Sultana, T. Porter, N.G. Savage, G.P. McNeil, Wattenberg, L.W. (1977). J Nat Cancer Inst 58:
D.L. (2003a). J Agrc Food Chem 51: 3586- 359-398.
3591.
Wattenburg, L.W. (1981). Cancer Res 41: 2991-
Sultana, T. McNeil, D.L. Porter, N.G. Savage, 2994.
G.P. (2003b). J Food Composition &
Analysis 16: 637-646. Weil, M.J. Zhang, Y. Nair, M.G. (2005). J Agric
Food Chem. 53: 1440-1444.
Sultana, T. Savage, G.P. McNeil, D.L. Porter, N.
Clark, B. (2003c). J Food Agric & Yang, Y.M. Conaway, C.C. Wang, C.X. Dai, W,
Environment 1(2): 117-121. Chiao, J.W. Albino, A.P. Chung, F.L.
(2002). Cancer Res, In press.
Tanida, N. Kawaura, A. Takahashi, A. Sawada,
K. Shimoyama, T. (1991). Nutr Cancer Zhang, Y. Talalay, P. (1994). Cancer Res 9
16: 53-58. (suppl.), 54: 1976-1981.