Review

TheScientificWorldJOURNAL (2004) 4, 811–837

ISSN 1537-744X; DOI 10.1100/tsw.2004.131

Raphanus sativus (Radish): Their Chemistry

and Biology

Rosa Martha Pérez Gutiérrez* and Rosalinda Lule Perez

Laboratorio de Investigación de Productos Naturales, Escuela Superior de Ingeniería
Química e Industrias extractivas IPN, México D.F.

E-mail: [email protected]

Received January 22, 2004; Revised August 14, 2004; Accepted August 18, 2004; Published September 13, 2004

Leaves and roots of Raphanus sativus have been used in various parts of the world to
treat cancer and as antimicrobial and antiviral agents. The phytochemistry and
pharmacology of this radish is reviewed. The structures of the compounds isolated and
identified are listed and aspects of their chemistry and pharmacology are discussed. The
compounds are grouped according to structural classes.

KEYWORDS: Raphanus sativus, Cruciferae, alkaloids, proteins, polysaccharides, phenolic and

sulfur compounds

DOMAINS: pharmaceutical sciences, therapeutic drug modeling

INTRODUCTION

The plant family of Cruciferae contains many important vegetables of economic importance. Raphanus
sativus L. is originally from Europe and Asia. It grows in temperate climates at altitudes between 190 and
1240 m. It is 30–90 cm high and its roots are thick and of various sizes, forms, and colors (see Fig. 1).
They are edible with a pungent taste. Salted radish roots (Takuan), which are consumed in the amount of
about 500,000 tons/year in Japan, are essentially one of the traditional Japanese foods. The salted radish
roots have a characteristic yellow color, which generates during storage.
This specie is used popularly to treat liver and respiratory illnesses[1]. The antibiotic activity of its
extracts and its time persistence validates its effectiveness in microbial sickness as reported in traditional
medicine. The root’s juice showed antimicrobial activity against Bacillus subtilis, Pseudomonas
aeruginosa, and Salmonella thyphosa. The ethanolic and aqueous extracts showed activity against
Streptococcus mutans and Candida albicans. Aqueous extract of the whole plant presents activity against
Sarcinia lutea and Staphylococcus epidermidis[2]. Aqueous extract of the leaves showed antiviral effect
against influenza virus. Aqueous extract of the roots showed antimutagenic activity against Salmonella
typhimurium TA98 and TA100. In this review, the metabolites produced by R. sativus are presented
according to structural classes. (See also Tables 1 through 10 at the end of this paper.)

*Corresponding author. Punto Fijo No. 16, Col. Torres de 811

Lindavista, C.P. 07708 Mexico, D.F. Mexico
©2004 with author.
Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

FIGURE 1

CHEMICAL CONSTITUENTS

Alkaloids and Nitrogen Compounds

Alkaloid and nitrogen compounds present in the roots were pyrrolidine, phenethylamine, N-
methylphenethylamine, 1,2´-pyrrolidin-tion-3-il-3-acid-carboxilic-1,2,3,4-tetrahydro-β-carboline, and
sinapine[3,4,5]. Cytokinin (6-benzylamino-9-glucosylpurine) is a major metabolite of 6-
benzylaminopurine (6-BAP) in the root radish. A minor metabolite of 6-BAP from radish has been
identified as 6-benzylamino-3-β-D-glucopyranosylpurine[6]. Total amino acids were 0.5% of dry wt;
with proline (0.5%) as the major constituent, methionine and cystine were present in traces (0.02%).
Diamines as diaminotoluene (2,4-D), 4,4´-methylenedianiline (4,4-D), and 1,6-hexanediamine (1,6-D)
were isolated in the period of germination of young radish seeds. Production of thiamine is higher during
germination radishes[7].
Total protein was 6.5%[8]. Two chitinases, designated RRC-A and RRC-B, were isolated from radish
roots. Both compounds had a molecular weight of 25 kDa[9]. N-Bromosuccinimide and di-Et-
pyrocarbonate inhibited the activities of both chitinases.
Arabinogalactan proteins (AGPs) were isolated from primary and mature roots of the radish. These
were composed mainly of L-arabinose and D-galactose. Structures of the carbohydrate moieties of the root
were essentially similar to those isolated from seeds and mature leaves in that they consisted of
consecutive (1→3)-linked β-D-galactosyl backbone chains having side chains (1→6)-linked β-D-
galactosyl residues, to which α-L-arabinofuranosyl residues were attached in the outer regions. One
prominent feature of the primary root AGPs was that they contained appreciable amounts of L-fucose[10].

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Two L-arabino-D-galactan–contained glycoproteins were isolated from the saline extract of mature
radish leaves; both contained L-arabinose, D-galactose, L-fucose-4-O-methyl-D-glucuronic acid, and D-
glucuronic acid residues. Degradation of the glycoconjugates showed that a large proportion of the
polysaccharide chains is conjugated with the polypeptide backbone through a 3-O-D-galactosylserine
linkage[11].
Arabino-3,6-galactan associated with a hydroxyproline-rich protein portion and carried a unique
sugar residue, α-L-fucopyranosyl-(1-2)-α-L-arabinofuranosyl[12].
Stigma glycoproteins heritable with S-alleles (S-glycoproteins) were detected in R. sativus. Two main
glycoproteins appeared on the SDS-gel electrophoretic pattern. Their molecular weights were established
to be 15,000 and 100,000 Da. The carbohydrate fraction of the glycoprotein consisted of arabinose 17.3%,
galactose 19.1%, xylose 8.1%, mannose 5.4%, glucose 23.7%, and rhamnose or fucose 26.4%. In the
stigma surface diffusate of R. sativus, the content of protein was established to be 16% and that of
carbohydrate was 11%[13].
The R. sativus acanthiformis showed two ferredoxin isoproteins indicating that plants have multiple
genes for ferredoxin. The relative abundance of the isoproteins varied with leaf stage[14]. In the
isoprotein isolated from roots of the radish, the amino acid composition and N-terminal sequence were
different from those of radish leaf ferredoxin.
Polypeptides RCA1, RCA2, and RCA3 were purified from seeds of R. sativus. Deduced amino acid
sequences of RCA1, RCA2, and RCA3 have agreement with average molecular masses from electrospray
mass spectrometry of 4537, 4543, and 4532 kDa, respectively. The only sites for serine phosphorylation
are near or at the C terminal and hence adjacent to the sites of proteolytic precursor cleavage[15].
Cysteine-rich peptides (Rs-AFP1 and Rs-AFP2) isolated from R. sativus showed peptides 6, 7, 8, and
9 comprising the region from cysteine 27 to cysteine 47[16]. Protein AFP1 isolated from radish showed
peptide fragments (6-mer, 9-mer, 12-mer, and 15-mer)[17].
Proteins RAP-1 and RAP-2 were isolated from Korean radish seeds. The molecular mass of the two
purified was established to be 6.1 kDa (RAP-1) and 6.2 kDa (RAP-2) by SDS-PAGE and 5.8 kDa (RAP-
1) and 6.2kDa (RP-2) by gel filtration chromatography[17].

Coumarins

Hydroxycoumarins aesculetin and scopoletin were also identified[18].

Enzymes

A number of enzymes are present in both the cytoplasm and the cell wall, and in some cases it has been
shown that the cell wall isozymes differ from those of the cytoplasmic[19]. When radish seedlings are
grown in the dark, β-fructosidase (βF) first accumulates in the cytoplasm, then slowly increases in the cell
wall. Charge heterogeneity of cytoplasmic enzymes resides in the polypeptides, while the formation of the
basic cell wall occurs as a result of post-translational modifications that can be inhibited by
tunicamycin[20].
Cysteine synthase (EC 4.2.99.8) was purified to near homogeneity (275-fold) in 11.5% yield from
mature roots. It was relatively stable, retaining most of its activity in standing for several days at room
temperature[21].
A basic β-galactosidase (β-Galase) has been purified from imbibed radish. This enzyme, consisting of
a single polypeptide with an apparent molecular mass of 45 kDa and pI values of 8.6 to 8.8, was
maximally active at pH 4.0 on p-nitrophenyl β-D-galactoside and β-1,3-linked galactobiose. Radish seed
and leaf arabino-3,6-galactan-proteins were resistant to the β-Galase[22]. β-Amylase[23], together with
peroxidase c or paraperoxidase[24], which is an isoenzyme, were also isolated from Japanese radish roots.

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A hydroxycinnamoyltransferase (EC 2.3.1.-), which catalyzes in vivo the formation of 1,2-di-O-

sinapoyl-β-D-glucose, was isolated from the radish. Cotyledons exhibited activities of 1-O-acyl-glucose–
dependent acyltransferases, 1-sinapoyl-glucose:L-malate sinapoyltransferase (SMT), and 1-
(hydroxycinnamoyl)-glucose:1-(hydroxycinnamoyl)glucose-hydroxyl cinnamoyl-transferase (CGT),
showing contrary developments depending on light conditions. Light-grown seedlings showed high L-
malate sinapoyltransferase and low 1-(hydroxycinnamoyl)glucose-hydroxyl cinnamoyl-transferase
activities, while dark-grown seedlings showed low L-malate sinapoyltransferase and high 1-
(hydroxycinnamoyl)glucose-hydroxyl cinnamoyl-transferase activities[25].
Catalase and glutathione reductase activities increased considerably in the root and leaves after 24-h
exposure to cadmium, indicating a direct correlation with Cd accumulation. PAGE enzyme activity
staining revealed several superoxide dismutase isoenzymes in leaves. The main response may be via
activation of ascorbate-glutathione cycle for removal of hydrogen peroxide or to ensure availability of
glutathione for synthesis of Cd-binding proteins[26].
A γ-glutamyl transpeptidase was found. It catalyzed the release of CySH-Gly from glutathione, the
release of alanine from γ-glu-Ala, and the formation of γ-glutamyl dipeptides. A dipeptide formed from S-
methylcysteine and glutathione or γ-glu-Ala was characterized as γ-glutamyl-S-methylcysteine[27].
Two cationic isoperoxidases (C1 and C3) and four anionic isoperoxidases (A1, A2, A3n, and A3)
were isolated from Korean R. sativus L. root. All the six isoperoxidases are glycoproteins composed of a
single polypeptide chain. The molecular weights of C1, C3, A1, and A2 were ca. 44,000, while anionic
isoperoxidase A3n and A3 have molecular weights of 31,000 and 50,000, respectively. N-terminal amino
acid sequences were determined for A1, A3n, and C3, while A2 was found to have a blocked terminal
residue[28]. Analysis of digested products of the two major N-glycans of C3 suggested that core-
fucosylated trimannosylchitobiose may contain a different linkage from the typical α-1,6 of native N-
linked oligosaccharide[29].
Thiamin-binding substances were found in the radish. There were two kinds of compounds; one was
heat labile and Pronase sensitive, and the other was heat stable and Pronase resistant. It would be inferred
that the former is protein and the latter is a nonprotein compound[30].
βF is an isozyme (glycoprotein) found in the cytoplasm and cell walls of the radish. The
nonglycosylated cytoplasmic and cell wall βF forms have the same relative molecular mass, but
glycosylated forms have different oligosaccharide side chains with respect to size and susceptibility to α-
mannosidase and endoglycosidase D digestion[31].
7-Glucoside de zeatin, isolated from radish cotyledons, occurs naturally as glycoside with β-glucose
as substituent. A large number of derivatives of purine are glucosylated, but adenine derivatives with
alkyl side chains at least three carbon atoms in length at position N6 are preferentially glucosylated[20].

Gibberellins

The bolting (stem elongation accompanying flowering) of R. sativus L. cv. Taibyo-sobutori requires cold
treatment (Vernalization) and subsequent long-day conditions. It has been suggested that gibberellins
(GAs) might be involved in the control of bolting. Eleven gibberellins were identified in extracts of
mature seed as 13 hydroxy-GAs [GA1, 3-epi-GA1, GA8, GA17, GA19, GA20, and a new GA, 12α-hydroxy-
GA20 (GA77)] and four non-13-hydroxy-GAs [GA9, GA24, 12β-hydroxy-GA24, GA25]. The major GAs
were GA8, GA20, and GA77[32].

Glucosinolates

Glucosinolates are very stable water-soluble precursors of isothiocyanates. The relatively nonreactive
glucosinolates are converted to isothiocyanates on wounding of the radish. The tissue damage releases

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myrosinase (EC 3.2.3.1), a glycoprotein that is physically segregated from its glucosinolate substrates.
Large variations in myrosinase-specific activity have been reported in various Cruciferous plant sources.
Myrosinase, purified to homogeneity from daikon, has a specific activity of 280 µMol/min/mg protein
with sinigrin as a substrate[33]. Glucosinolate contents of seed of radish cultivar ranged from 37–87
µmol/g seed. The 5-vinyl-2-oxazolidinethione, 3-butenyl, 4-pentenyl, and phenethyl isothiocyanate were
found in industrially extracted rapeseed oils. The compounds were hydrolysis products from
glucosinolates present in the seed[34].
Desulfoglucosinolates are formed by enzyme desulfation of endogenous glucosilates. The indole
glucosinolates, 4-methoxy-3-indolylmethyl glucosinolate and 1-methoxy-3-indolylmethoxy glucosinolate,
were absent in seed whereas 4-hydroxy-3-indolymethyl glucosinolate was found in highest concentration
in the seeds. The 3-indolymethyl glucosinolate was found in low levels in seed, but was the dominant
indole glucosinolate in the leaf[35].

Oil Seed Components

The seeds of the radish contain a high percentage of oil. Chromatographic analysis of these oils showed
clearly their complete similarities to cottonseed oil[36]. The steam volatile constituents of fresh radish of
Japanese and Kenyan origin have been studied. The overall pattern of compounds in the two materials
was similar. Major components are pentyl hexyl, 4-methylpentyl isothiocyanate, dimethyl disulfide,
methyl methanethiolsulfinate, and 1-methylthio-3-pentanone[37]. Oil radish seeds contained 1.21 µmol of
total alkenylglucosinolates (AG/g), consisting mostly of progoitrin and gluconapin[38].

Organic Acids

Four major organic acids are present in the roots of the radish: oxalic, malic, malonic, and erythorbic acid.
Lipid total was 1.23%[8]. Major fatty acids in seed lipids were erucic, oleic, linoleic, and linolenic acids.
Major fatty acids in radish family lipids were linolenic acid (52–55%), followed by erucic acid (30–33%),
and palmitic acid (20–22%)[39]. Also identified were stearic acid from petroleum ether extracted from
powdered R. sativus seeds. Glutamic acid is found in pickled daikon (20–100 mg%)[40].

Phenolic Compounds

The content of phenolic acids in the roots of the radish were much smaller than in the leaves. Radishes
and horseradish showed caffeic, p-coumaric, ferulic, hydroxycinnamic, p-hydroxybenzoic, vanillic,
salicylic, and gentisic acid[18]. Sinapic acid esters (1-sinapolyglucose, sinapoyl-L-malate, and 6,3´-
disinapoylsucrose), kaempferol glycosides, and free malic acid were isolated from cotyledons of R.
sativus seedlings[41].
Among the anthocyanins, pelargonidine and cyanidine were responsible for red and violet color in
corollas and roots in all inbred progenies. The absence of pelargonidine and cyanidine resulted in a white
color. The flavonoid, quercetine, was also found in both corolla and root[42]. Anthocyanins extracted
from epidermal tissue resulted in juices with fairly low initial ˚Brix (1.3˚), containing 400 mg
anthocyanin/100 ml. This compound provided color similar to FD&C Red#40. Radish concentrate extract
represents a promising natural alternative to the use of FD&C Red#40[43].
Other purple root pigment isolated from progeny radish was an ester of cyaniding triglucoside and three
kinds of cinnamic acids. The triglucoside was identified as the 2-diglucoside-5-monoglucoside of cyaniding
(Rubrobrassicin)[44]. Other anthocyanins obtained from red radish are two diacylated pelargonidin 3-O-[2-
O-β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-(6-O-malonyl-β-glucopyranoside)
and pelargonidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-feruloyl)-β-glucopyranoside]-5-O-(6-O-

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malonyl-β-glucopyranoside) and other monoacylated anthocyanins pelargonidin 3-O-[2-O-β-

glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-D-glucopyranoside]-5-O-(β-glucopyranoside) and pelargonidin
3-O-[2-O-β-glucopyranosidel)-6-O-(trans-p-feruloyl)-β-glucopyranoside]-5-O-(β-glucopyranoside). Pelar-
gonidin-3-diglucosido-5-monoglucoside is known as raphanusin[45].
The major anthocyanins of radishes are pelargonidin-3-sophoroside-5-glucoside acetylated with
malonic acid and either ferulic or p-coumaric acid. Cinnamic acid acylation site for radish anthocyanins
was determined to be at position 6 of glucose-1 of the sophorose substituents by one- and two-
dimensional 1HNMR-13CNMR[46]. Also 7-glucoside-pelargonidin has been identified in R. sativus[47].
This compound was stable at 60˚C and under light, may be used as a food colorant[48].
Kaempferol-7-O-rhamnoside, isorhamnetin-7-O-rhamnoside, quercetin-7-O-rhamnoside, kaempferol-
3-glucoside-7 rhamnoside, kaempferol-7-glucoside-3 rhamnoside, quercetin-7-O-arabinoside-3-glucoside,
and quercetin-7-glucoside-3 rhamnoside were isolated from R. raphanistrum[49]. Radishes have a high
content of flavonoids as quercetin, kaempferol, myricetin, apigenin, and luteolin[50]. Malvidin-3,5-
diglucoside was produced from the callus of radish via tissue cultivation. The callus contains 16.4% (dry
wt) pigments[51].

Pigments

Salted radish roots have a characteristic yellow color, which generates during storage. 4-Methylthio-3-
butenyl-glucosinolate (4-MTBG) is the substrate of the main pungent principle of radish and is one of the
essential factors for the formation of the yellow pigment. The yellow compound 1-(2´-pyrrolidinethion-
3´-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxilic acid is presumed to have been the condensation product
from the degradation of 4-methylthio-3-butenylisothiocyanate and L-tryptophan, which carboline
compound is considered to play an important role in the formation of the yellow pigment in salted radish
roots[52].

Polysaccharides

Pectic substances were extracted from the leaves with oxalate buffer of pH 4.25 as weakly acidic pectic
polysaccharide (WAP) and pectic acid. WAP was appreciably hydrolyzed by exo- and
endopolygalacturonases and the galacturonic acid content (17.3–25.8%) was much lower than the pectic
acids, though the neutral sugar components of both pectic substances were almost the same. The
arabinose-galactose side chains were very long or highly branched in pectine compared with those in
pectic acids. These compounds are probably inherent pectic components of the cell walls of the
vegetables[53]. Rhamnose, glucose, and xylose were also isolated. Lipopolysaccharides (LPS) were
isolated from radish roots[54].

Proteoglycan

An L-arabino-D-galactan–contained proteoglycan was isolated from hot phosphate-buffered saline extract

of radish seeds by ethanol fractionation. The proteoglycan consisted of 86% of a polysaccharide
component–contained L-arabinose and D-galactose as major sugar constituents, together with small
proportions of D-xylose, D-glucose, and uronic acids, and 9% of a hydroxyproline-contained protein.
Arabinogalactan from radish seed had a high content (81%) of L-arabinose and its basic structure seemed
to be similar to that of the polysaccharide component of the proteoglycan[55].

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Sulfur Compounds

Radish leaves contain only one of the sulfonium diateroisomers of S-adenosylmethionine (AdoMet),
which has a remarkable variety of biochemical functions. It is an allosteric enzyme effector and a
precursor of spermine biosynthesis, spermidine, and ethylene. It is also the methyl group donor for most
biological transmethylation reactions, wherein transfer of its methyl group converts AdoMet to the
homocysteine analog (AdoHcy). Much of the chemistry and biochemistry of AdoMet derives from the
fact that it is a sulfonium compound[56]. 1-(2´-Pyrrolidinethion-3´-yl)-1,2,3,4-tetrahydro-β-carboline-3-
carboxilic acid was found in radish root. This carboline compound is considered to play an important role
in the formation of the yellow pigment in salted radish roots.

Other Constituents

β-Carotene was isolated from radish. Vitamin C content in fresh hotbed radishes ranged from 17.95–
27.86 mg%[57]. Also identified was β-sitosterol from R. sativus seeds[40]. The contents of raphanusol A
and B in radish increased at the lighted side and decreased in the shaded side. The differential distribution
of raphanusol A and B in the hypocotyls is closed correlated with growth suppression at lighted side[58].

BIOLOGICAL ACTIVITIES

Allergic Contact

In the radish, the allyl isothiocyanate released enzymically from simigrin, a thioglycoside, was identified
as a possible sensitizing substance. In some cases, it can produce allergic contact and dermatitis[59]. The
leaves of this plant also contained glucoparin that produced allergic contact.

Antimicrobial Activity

Crude juice of the radish inhibited the growth of Escherichia coli, Pseudomonas pyocyaneus, Salmonella
typhi, and Bacillus subtilis in vitro. This common plant may be an important source of antimicrobial
substances[60]. The cysteine-rich peptides (Rs-AFP1 and Rs-AFP2) isolated from R. sativus showed
substantial antifungal activity against several fungal species with minimal inhibitory concentration (MIC)
of 30–60 µg/ml. Both Rs-AFPs are among the most potent antifungal proteins characterized. Moreover,
their antibiotic activity shows a high degree of specificity to filamentous fungi[16]. The active region of
the antifungal protein appears to involve β-strands 2 and 3 in combination with the loop connecting those
strands[61]. Rs-AFP1 and Rs-AFP2 are highly basic oligomeric proteins composed of small (5-kDa)
polypeptides that are rich in cysteine. These proteins are located in the cell wall and occur predominantly
in the outer cell layers lining different seed organs. Moreover, Rs-AFPs are preferentially released during
seed germination after disruption of the seed coat[62]. Two purified antifungal proteins RAP-1 and RAP-
2 isolated from Korean radish seeds (R. sativus) exhibited growth-inhibitory activities against Candida
albicans and Saccharomyces cerevisiae[63]. The protein AFP1 isolated from the radish showed
antifungal activity against Fusarium culmorum[17].
Caffeic acid showed antifungal properties in vitro against Helminthosporium maydis. It has
antibacterial, antifungical activities. Ferulic acid is active against Sytaphylococcus aureus, Bacillus
subtilis, Corynebacterium, diphtheria, Aspergillus niger, and Candida albicans. These acids displayed
antibacterial activity against Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus, and the
Gram-negative Escherichia coli and Kliebsiella pneumoniae. The MIC values were 1.56–3.13 µg/ml.

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These p-hydroxybenzoic acid (hydroxycinnamic, p-hydroxybenzoic) showed marked activity against

Gram-positive bacteria.
The inoculation of sliced daikon roots with the bacterium Pseudomonas cichorii induced the
formation of several antifungal compounds including brassinin, methoxybrassinin, spirobrassinin, and 3-
indolecarbaldehydes[64].
The radish released biocidal compounds, mainly isothiocyanates, produced during the enzymic
degradation of glucosinolates present in the plant cell. The highest fungicidal activity depended on
concentration of isothiocyanates[65].

Antioxidative Activity

The red radish pigment (pelargodinin-3-sophoroside-5-glucoside) had almost the same antioxidative
activity as BHT at the same concentration. The inhibition ratio could reach more than 93% by the 0.01%
pigment addition[66]. Also, the caffeic acid showed antioxidative activity.

Antitumor Activity

A neutral fraction of kaiware radish extract aqueous in vitro showed proliferation inhibition of mouse
embryo fribroblast 3T3 cells and papovavirus SV40 transformed 3T3 cells with IC50 of 17.4 and 8.7
µg/ml[67]. Diaminotoluene (2,4-D) showed highest cytotoxic activity against He-La cells, 4,4´-
methylenedianiline (4,4-D) intermediate, and 1,6-hexanediamine (1,6-D) lowest cytotoxicity. However,
the phytotoxicity decreased in order of 4,4-D >2,4-D>1,6-D[7].

Antiviral Activity

Caffeic acid and pelargonidin are virucidal for several enveloped viruses[41]. The lipopolysaccharides
showed antiherpes activity.

Calmodulin Antagonists

The polypeptides RCA1, RCA2, and RCA3 inhibit chicken gizzard calmodulin-dependent myosin light
kinase assayed with a myosin-light chain-based synthetic peptide substrate[15].

Growth Inhibitors

The hypocotyls cis- and trans-raphanusanins and 6-methoxy-2,3,4,5-tetrahydro-1,3-oxazepin-2-one

(raphanusamide) were isolated from radish. Cis- and trans-raphanusanins inhibited the hypocotyls growth
at concentrations higher than 1.5 µM and raphanusamide at concentrations higher than 20 µM[68].
Growth-inhibitor 2-thioxothiazolidine-4-carboxilic acid was isolated from acetone extract of light-
exposed seedlings of Sakurajima radish. It inhibited the growth of hypocotyl sections of etiolated
Sakurajima radish and intact hypocotyls of etiolated lettuce seedlings at concentrations greater than 3
mg/ml. Gibberellins were identified in extracts of mature seed radish and might be involved in the control
of bolting (stem elongation accompanying flowering) of R. sativus[32].

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Hypotensive

Sinapine was extracted with methanol. It is a hypotensive constituent of laifuzi (Semen raphani) and seed
of R. sativus[5].

Platelet Aggregation Inhibitor

The 6-methyl-sulfinylhexyl-isothiocyanate (MS-ITC) was isolated from wasabi horseradish (Japanese

domestic) as a potential inhibitor of human platelet aggregation in vitro. It is a potential inducer of GST
(glutathione S-transferase). In the mechanism of MS-ITC, the isothiocyanate moiety of MS-ITC plays an
important role for antiplatelet and anticancer activities because of its high reactivity with sulfhydryl (-SH)
groups in biomols (GSH, cysteine, residue in a certain protein)[69].

Immunological Properties

The AGPs isolated from the radish showed immunological properties. Radish AGPs R-I, R-II, crude
fraction R-C, and turnip AGP B-II reacted with eel anti-H serum, indicating that these AGPs shared
common antigenic determinants[70]. The root’s AGPs were composed mainly of L-arabinose and D-
galactose, but were distinguishable from each other in their contents of L-fucose as well as of protein and
hydroxyproline. Structures of AGPs from the root, seeds, and mature leaves were essentially similar[71].
Proteoglycan from radish leaves and seeds appeared to share common antigenic determinant[55].

Phytoalexins

The inoculation of sliced daikon roots with the bacterium Pseudomonas cichorii induced the formation of
several antifungal compounds including brassinin, methoxybrassinin, spirobrassinin, and 3-
indolecarbaldehydes[64].

Pungent Principle

The pungent principle extracted from the radish root is trans-4-methylthio-3-butenyl-isothiocyanate. Also
isolated was the cis-isomeride, in a trans–cis ratio of 4:1[72]. 2-Thioxo-3-pyrrolidinecarbaldehyde (TPC)
is a major product generated from the pungent principle of radish. This compound possesses antimicrobial
activity with the MIC against fungi and bacteria ranging from 50–400 µg/ml, while yeasts were more
resistant. The antifungal and antibacterial actions were due to the sporicidal and bactericidal activities. A
dose-dependent inhibition of the uptakes of both oxygen and the precursors for RNA and DNA was
observed, suggesting that TPC caused damage to the mitochondrial functions and biosynthetic
systems[73].

Serological Activity

AGPs were presumably responsible for expression of the serological activity. In their immunological
reactions with rabbit antiradish leaf AGP antibody, the root AGPs were shown to share common antigen
determinant with those of seed and leaf AGPs[10]. Arabino-3,6-galactan associated with a
hydroxyproline-rich protein portion, which might be responsible for the serological H-like activity of the

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AGPs[12]. Two L-arabino-D-galactan–contained glycoproteins having potent inhibitory activity against

eel anti-H agglutinin were isolated from the saline extract of mature radish leaves[70].

Intestine Motility Stimulation

The effect of radish aqueous extract at doses of 10 µg/ml to 2 mg/ml caused a dose-dependent increase in
contractions of the duodenum, jejunum, and ileum. Ileal contraction was remarkably inhibited by
pretreatment of atropine (10–7 M) by 10 min. Oral administration of radish extract (300–500 mg/kg body
wt) to mice improved the intestinal transit of charcoal and this was significantly attenuated by co-
administration of atropine (50 mg/kg). These results suggest that radish extract stimulates gastrointestinal
motility through activation of muscarinic pathways[74]. Scopoletin is an antispasmodic agent.

Cardiovascular Disease Prevention

Radish powder decreased the lipid levels by increasing the fecal excretion of total lipids, triglycerides, and
total cholesterol. Catalase and glutathione peroxidase (GSH-Px) activities in red blood cell (RBC) were
most remarkably increased by radish. Superoxide dismutase (SOD), catalase, and GSH-Px activities in the
liver were increased by radish powder. Xanthine oxidase (XOD) activities in the liver were decreased by
radish. Flavonoids and vitamin C in radish may inhibit lipid peroxidation, promote liver and RBC catalase,
and inhibit XOD activities in animals tissues. Radish can be recommended for the treatment and prevention
of diseases such as cardiovascular disease and cancer and for delaying aging[75].

Other Activities

Lipopolysaccharides (LPS) were isolated from radish having a macrophage activating with ED50 of 0.4–
100 ng/ml. These compounds can be used as antidiabetic agents in pharmaceutical or veterinary fields.
Also the LPS showed analgesic activity[54].

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This article should be referenced as follows:

Pérez Gutiérrez, R.M. and Perez, R.L. (2004) Raphanus sativus (radish): their chemistry and biology.
TheScientificWorldJOURNAL 4, 811–837.

Handling Editors:
Joseph Chamberlain, Principal Editor for Pharmaceutical Sciences and Therapeutic Drug Monitoring — domains of
TheScientificWorldJOURNAL.

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Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

TABLE 1
Alkaloids and Nitrogen Compounds Isolated from Radish

Structure Source Activities

Cotyledon[6] Cytokinin activity[6]

(6-Benzylamino-9-glucosylpurine)
Cotyledon[6] Cytokinin activity[6]

6-Benzylaminopurine
2,4-Diaminotoluene Germination of young radish Cytotoxic activity against
4,4´-Methylenedianiline seeds[7] He-La cells[7]
1,6-Hexanediamine
Leaves[3] Skin irritant and possible
sensitizer[5]

Phenethylamine
Radish leaves[4]

Pyrrolidine
Leaves[3]

1-(2´-Pyrrolidinethion-3´-yl)- 1,2,3,4-tetrahydro-β-
carboline-3-carboxilic
All tissue[68] Inhibited growth of
etiolated radish[68]

Raphanusamide

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TABLE 1 (CONTINUED)
Alkaloids and Nitrogen Compounds Isolated from Radish

Structure Source Activities

Seeds[5] Hypotensive[76]

Sinapine
Germination[30] Essential vitamin[30]

Thiamine

TABLE 2
Coumarins Isolated from Radish

Structure Source Activities

Root[18] Antifungical[76]

Aesculetin
Root[18] Antispasmodic[76]

Scopoletin

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TABLE 3
Enzymes Isolated from Radish

Structure Source Activities

Anionic isoperoxidases: A1, A2, A3n, and A3 Leaves[29]
β-Amylase Roots[23]
Arabinogalactan proteins Leaves, primary and mature Serological activity[10]
roots[10]
Catalase Leaves[26]
Cationic isoperoxidases: C1 and C3 Korean radish roots[28])
Anionic isoperoxidases: A1, A2, A3n, and A3
Cysteine synthase Mature roots[21] Antifungical[21]
β- Galactosidase Seeds[22]
7-Glucoside de zeatin Cotyledons[20] Cytokinin activity[20]
γ-Glutamyl transpeptidase Bulb[27]
Glutathione reductase Roots and leaves[27] Antioxidant activity;
lowering lipid levels[26]
Hydroxycinnamoyltransferase Cotyledons of radish[25]
β-Fructosidase (βF) Mature leaves[31]
Peroxidase c Japanese radish roots[24]
Superoxide dismutase Roots and leaves[75]) Antioxidant activity;
lowering lipid levels
1-(Hydroxycinnamoyl)glucose-hydroxyl cinnamoyl- Cotyledons[25] Effect on light-grown
transferase (CGT) seedling[25]
L-Malate sinapoyltransferase (SMT) Cotyledons[25] Showed effect on light-
grown seedling[25]

TABLE 4
Gibberellins Isolated from Radish

Structure Source Activities

Mature seed of radish[32] Control of bolting[32]

GA8
Mature seed of radish[32] Control of bolting[32]

GA9

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TABLE 4 (CONTINUED)
Gibberellins Isolated from Radish

Structure Source Activities

Mature seed of radish[32] Control of bolting[32]

GA17
Mature seed of radish[32] Control of bolting[32]

GA19
Mature seed of radish[32] Control of bolting[32]

GA20
Mature seed of radish[32] Control of bolting[32]

GA24
Mature seed of radish[32] Control of bolting[32]

GA25
Mature seed of radish[32] Control of bolting[32]

GA77

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TABLE 5
Organic Acid Isolated from Radish

Structure Source Activities

Leaves[18] Antioxidative, anti-HIV,
antineoplastic, choleretic,
hepatotropic, and
antifungal properties[41]

Caffeic acid
Leaves[18]

p-Coumaric acid
Leaves and roots[41]

Erucic acid
Leaves and roots[41]

Erythorbic acid
Leaves[41] Antifungical[41]

Ferulic acid
Leaves and roots[41] Aanalgesic, antiarthritic,
antirheumatic, and
cytostatic[76]

Gentisic acid
Pickled daikon[18]

Glutamic acid

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TABLE 5 (CONTINUED)
Organic Acid Isolated from Radish

Structure Source Activities

Leaves and roots[41] Antimicrobial[76]

Hydrocinnamic acid
Leaves and roots[18] Antimicrobial[18]

p-Hydroxybenzoic
Leaves and roots[41] Antifungical[76]

Salicylic acid
Leaves and roots[41] Antimicrobial[41]

Vanillic acid
Linoleic, linolenic, malic, malonic, oleic, oxalic, and Leaves and roots[39]
palmitic acid

TABLE 6
Phenolic Compounds Isolated from Radish

Structure Source Activities

Leaves and roots[42] Antiulcer[76]

Cyanidin

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TABLE 6 (CONTINUED)
Phenolic Compounds Isolated from Radish

Structure Source Activities

Roots, leaves, and green
cotyledons[43]

Isorhamnetin-7-O-rhamnoside
Roots and leaves[44] Antiinflammatory, diuretic,
and antioxidant[76]

Kaempferol
Upper epidermis of the Antiinflammatory[76]
cotyledons[49]

Kaempferol-3-glucoside-7-rhamnoside
Roots[49] Antiinflammatory[49]

Kaempferol-7-O-rhamnoside
Roots[48] Antiinflammatory[76]

Kaempferol-7-glucoside-3-rhamnoside
Roots[50] Antiinflammatory,
antitussive, antispasmodic,
antitumourigenic, and anti-
HIV activities[76]

Luteolin

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TABLE 6 (CONTINUED)
Phenolic Compounds Isolated from Radish

Structure Source Activities

Callus[51]

Malvidin-3,5-diglucoside
Roots[50] Anti-HIV activity[76]

Myricetin
Roots and fruits[47]

Pelargonidin
Roots[45] Antioxidant[76]

Pelargonidin-3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-
p-coumaryl)-β-glucopyranoside]-5-O-(6-O-malonyl-β-
glucopyranoside)

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TABLE 6 (CONTINUED)
Phenolic Compounds Isolated from Radish

Structure Source Activities

Roots[45] Antioxidant[76]

Pelargonidin-3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-
feruloyl)-β-glucopyranoside]-5-O-(6-O-malonyl-β-
glucopyranoside)
Roots[45] Antioxidant[76]

Pelargonidin 3-O-[2-O-β-glucopyranosyl)-6-O-(trans-
p-coumaroyl)-β-D-glucopyranoside]-5-O-(β-
glucopyranoside)
Roots[45] Antioxidant activity[76]

Pelargonidin 3-O-[2-O-β-glucopyranoside)-6-O-
(trans-p-feruloyl)-β-glucopyranoside]-5-O-(β-
glucopyranoside).

832
Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

TABLE 6 (CONTINUED)
Phenolic Compounds Isolated from Radish

Structure Source Activities

Roots and corollas[50] Anticarcinogenic,
antitumour promotor, and
anti-HIV activities[50]

Quercetin
Roots[49]

Quercetin-7-O-rhamnoside
Roots and corollas[49]

Quercetin-7-O-arabinoside-3-glucoside
Bud and flowers[49]

Quercetin-7-O-glucoside-3-rhamnoside
Roots[47]

Raphanusin

833
Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

TABLE 7
Polysaccharides Isolated from Radish

Structure Source Activities

Lipopolysaccharides (LPS) Roots[54] Antidiabetic, antiherpes,
analgesic, and having a
macrophage activation[76]
Pectic substances Leaves[53]
Proteoglycan Seeds[55]
Rhamnose, glucose, and xylose Leaves[53]

TABLE 8
Proteins Isolated from Radish

Structure Source Activities

Arabinogalactan-proteins (AGPs) Mature leaves[10] Reacted with eel anti-H
serum[10]
L- Arabino-D-galactan Mature leaves[11] Reacted with eel anti-H
Arabino-3,6-galactan serum[11]
Chitinase RRC-A Roots[9]
Chitinase RRC-B
Cysteine-rich peptides Rs-AFP1 and Rs-AFP2 Roots[17] Antimicrobial[17]
Ferredoxin isoproteins Leaves and roots[14]
S-Glycoproteins Mature leaves[13]
Myrosinase Daikon[8]
Polypeptides RCA1, RCA2, and RCA3 Mature leaves[15] Calmodulin antagonist[15]
Proteins AGPs Mature leaves[10] Serological H-like
activity[10]
Proteins RAP-1 and RAP-2 Seeds[63] Antimicrobial[63]
Protein AFP1 Seeds[17] Antifungical[17]

TABLE 9
Sulfur Isolated from Radish

Structure Source Activities

H2C=CHCH2NCS Leaves[59] Produce allergic contact
Allyl-isothiocyanate and dermatitis[59]
Phytoalexin in daikon[64] Antifungical[76]

Brassinin

834
Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

TABLE 9 (CONTINUED)
Sulfur Isolated from Radish

Structure Source Activities

Oil radish seeds[38]

Gluconapin
Glucosinolate Seeds[34]
Phytoalexin in daikon[64] Antifungical[76]

Methoxybrassinin
6-Methyl-sulfinylhexyl-isothiocianate Leaves and roots[69] Inhibitor of human platelet
aggregation[69]
Myrosinase Daikon[33]
Roots[72] Pungent[72]

trans-4-Methylthio-3-butenyl-isothiocyanate
Roots[56]

Phenethylisothiocyanate
Oil radish seeds[38]

Progoitrin
Root[35]

1-(2´-Pyrrolidinethion-3´-yl)-1,2,3,4-tetrahydro-β-
carboline-3-carboxilic acid

835
Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

TABLE 9 (CONTINUED)
Sulfur Isolated from Radish

Structure Source Activities

Oil radish seeds[34]

cis-Raphanusanin

trans-Raphanusanin
CH2=CHCH2CH2C(SGLc)=NOSO3H Leaves[33] Produce allergic contact
Sinigrin and dermatitis[33]
Phytoalexin in daikon[64] Antifungical[76]

Spirobrassinin
Immature leaves[56]

(S)-sulfonium form of S-adenosylmethionine

Roots[61] Antimicrobial, inhibited the
growth of hypocotyls[61]

2-thioxothiazolidine-4-carboxilic acid
Immature leaves[61]

5-Vinyl-2-oxazolidinethione
Other sulfurs: Oil radish seeds[38] Biocidal and fungicidal
Isothiocyanate activity[38]
Dimethyl disulfide
Methyl methanethiolsulfinate
1-Methylthio-3-pentanone

836
Pérez Gutiérrez and Perez: Raphanus sativus (Radish) TheScientificWorldJOURNAL (2004) 4, 811–837

TABLE 10
Other Compounds Isolated from Radish

Structure Source Activities

Carotenoids Leaves[57] Antioxidant[76]
Fatty acids Seeds[8]
Leaves[68] Growth inhibitor[68]

Raphanusol A
Leaves[68] Growth inhibitor[68]

Raphanusol B
Pentyl Oil radish seeds[37]
Hexyl
4-Methylpentyl

837
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