Health Promoting Effects of Phytochemicals from Brassicaceae A Review

Review Article Indian J. Pharm. Biol. Res Vol. 1 (3), Sep., 2013 ISSN:2320-9267

Health Promoting Effects of Phytochemicals from Brassicaceae: A Review

Savinder Kaur Mann and Namita Khanna*

Department of Botanical and Environmental Sciences, Guru Nanak Dev University, Amritsar, India.

*Department of Physiology, Guru Gobind Singh Medical College, Baba Farid University of Health Sciences,

Faridkot, Punjab, India.

Received 16-08-2013; Revised 24-08-2013; Accepted 26-08-2013

……………………………………………………………………………………………………… Abstract

Over the past several years, natural antioxidants have attracted considerable interest as potential treatment for a wide

variety of disease states, including cancer and other causes e.g. chronic inflammatory diseases and aging. Therefore,

plant derived antioxidants are now receiving a special attention as they possess good antioxidant properties and

hence a worldwide trend towards the use of natural phytochemicals present in fruits and vegetables have been

reported. Numerous epidemiological studies indicate that consumption of cruciferous vegetables is associated with

prevention of cardiovascular diseases and reduced incidence of cancers of the gastrointestinal tract and other sites.

The substances that seem to be responsible for these properties are phenolic compounds (phenolic acids, flavonoids,

polyphenols etc.) and sulphur-containing organic compound glucosinolates and their derived products. The present

review focuses on the health promoting effects of phytochemicals and their beneficial bioactivities in Brassicaceae.

Keywords: antioxidant, brassica, flavonoids, glucosinolates, phytochemicals, polyphenols,

……………………………………………………………………………………………………………………………..

1. Introduction

Reactive oxygen species (ROS) present a

paradox in their biological function: on

one hand, they prevent disease by

assisting the immune system, mediating

cell signaling and playing an essential

role in apoptosis [1]. On the other hand,

they can damage important

macromolecules in cells and may have a

role in carcinogenesis and cardiovascular

diseases. Historically, the generation of

ROS has been viewed as indiscriminate

and random, and their targets as primary

determinants of disease and aging [2]. A

lack of antioxidants, which can quench

the reactive free radicals, facilitates the

development of degenerative diseases

[3], including cardiovascular diseases,

cancers [4], neurodegenerative diseases,

Alzheimer’s disease [5] and inflammatory diseases [6]. Butylated

hydroxyanisole (BHA), butylated

hydroxytoluene (BHT), propyl gallate,

and tert-butylhydroquinone are the most

commonly used antioxidants at the

present time. However, their safety has

recently been questioned due to their

toxicity and possible carcinogenicity

[7,8]. One solution to this problem is to

supplement the diet with antioxidant

compounds that are contained in natural

plant sources [9]. These natural plant

antioxidants can therefore serve as a type

of preventive medicine.

Among these active antioxidant

phytochemicals, phenolic compounds

constitute the largest group and are the

secondary metabolites that are

derivatives of the pentose phosphate,

*Corresponding Author: Dr. Namita Khanna, Department of Physiology, Guru Gobind Singh Medical College,

BFUHS, Faridkot, Punjab, India. E-Mail Id: [email protected], [email protected] Mobile No.

+91-9417392924. 120

mailto:[email protected]

mailto:[email protected]

Khanna et al.,1(3);2013

Available online on www.ijpbr.in 121121121

shikimate and phenylpropanoid

pathways in plants [10, 11]. They have

been associated with several health

benefits such as: anti-allergic, anti-

artherogenic, anti-inflammatory, anti-

microbial, antioxidant, anti-thrombotic,

cardioprotective and vasodilatory effects

[12-15]. In this aspect, the popularity

and consumption of Brassica vegetables

is increasing because of their nutritive

value. The beneficial effects of Brassica

vegetables on health improvement have

been partly attributed to their complex

mixture of phytochemicals possessing

antioxidant activity, especially phenolic

compounds and sulphur containing

compounds, glucosinolates and their

hydrolysis products. These sulphurous

compounds are considered as indirect

antioxidants, as they are not involved in

the scavenging of free radicals directly,

but rather by modulating the activity of

xenobiotic metabolizing enzymes, phase

I and phase II enzymes that trigger the

antioxidant activity. Hence, an attempt

has been made to review briefly the

important compounds present in

Brassicaceae with an emphasis on their

biological activity as free radical

scavengers.

2. Phenolic compounds in

Brassicaceae

Plant phenolics are multifunctional,

having diverse biological activities apart

a) P-coumaric Acid b) Ferulic Acid

from acting as reducing agents. They

range from simple, low molecular

weight, single aromatic-ringed

compounds to large and complex tannins

and derived polyphenols. The most

widespread and diverse group of

phenolic compounds in Brassica species

are the phenolic acids (hydroxybenzoic

and hydroxycinnamic acids), flavonoids

(flavonols and flavones) and

polyphenols (hydrolysable and

condensed tannins). The contribution of

Brassica species to health improvement

has generally been associated with their

antioxidant capacity and, undoubtedly,

phenolic compounds are the major

antioxidants of the Brassicaceae [16].

Species of Brassicaceae family are

generally rich in polyphenols. Brassica

rapa and Brassica oleracea L. var.

botrytis contain a high amount of

phenolic compounds [17]. The

antioxidant properties of phenolic

compounds are mainly because of their

redox potential, which allows them to

act as reducing agents, hydrogen

donators, metal chelators and singlet

oxygen quenchers.

2.1 Bio-protective effects of phenolics

in Brassica crops

In Brassicaceae the most common

hydroxycinnamic acids are p-coumaric,

sinapic and ferulic acids, often found in

conjugation with sugar and other

c) Caeffic Acid d) Sinapic Acid

Figure -1: Chemical structures of some hydroxycinnamic acids



hydroxycinnamic acids [18, 19]. In the

case of broccoli, hydroxycinamic acids

such as ferulic, sinapic, caeffic and

protocatechuic acids were found to be

the most abundant and important

bioactive compounds [20] (Fig. 1). It has

been demonstrated that Canola (B.

napus) seeds, canola oil and their by-

products are rich in polyphenols,

including, ferulic, sinapic, caeffic,

cinnamic, p-coumaric, p-hydroxybenzic,

salicylic and syringic acids with high

radical-scavenging activities [21, 22].

The antioxidant potential of different

edible parts of B. rapa var. rapa L. was

investigated against DPPH radicals and

revealed that the flower buds were the

most active part (IC25 = 0.47 mg/ml),

followed by the leaves and stems (IC25 =

0.56 µg/ml). The HPLC-DAD analysis of

its aqueous extracts revealed the presence

of several hydroxycinnamic acids and

flavonoid derivatives [23]. The phenolic

acid composition and antioxidant activity

of canola (B. napus) extracts in cooked

beaf, chicken and pork has been studied

and revealed that the crude polyphenol

extracts (15 or 100 mg GAE/kg meat)

from canola meal inhibited the lipid

oxidation in pre-cooked beaf (66-92%),

pork (43-75%) and chicken (36-70%).

The extracts were also found to contain

hydroxycinnamic acids, sinapic (99.7%),

ferulic (0.28%) and p-hydroxybenzoic

acids (0.07%) [24]. The antioxidant

O

OH

O

OH

HO

HO

HO

O

OH

(a) Vanillic Acid (b) Gallic Acid

potential of tronchula cabbage (B.

oleracea L. var. costata DC) was

evaluated and it showed an IC25 = 64

µg/ml in DPPH radical scavenging assay.

It scavenged xanthine/xanthine oxidase

(X/XO) generated superoxide radical and

Fenton system generated hydroxyl

radical in a concentration dependent

manner with an IC25 = 197 µg/ml and

IC25 = 4 µg/ml respectively.

Hydroxycinnamic acids like caffeic acid,

p-coumaric acid, ferulic acid, and sinapic

acid were found to be present in potherb

mustard (Brassica juncea, Coss.) [25,26].

Hydroxybenzoic acids are commonly

present in a bound form, constitute either

complex structures like hydrolyzable

tannins or simple molecules by combining

with sugars or organic acids [27,28]. The

most common hydroxybenzoic acids

include gallic, p-hydroxybenzoic,

protocatechuic, vanillic and syringic acids

(Fig. 1). The leaves and seeds of Brassica

oleraceae L. var. acephala DC. (kale)

were studied and were identified to have

five hydroxybenzoic acid derivatives

(gallic, protocatechuic, p-hydroxybenzoic,

vanillic and salicylic acid) in the leaves

[29]. These hydroxybenzoic acid

derivatives (HBAs) were quantified at

concentration of 143, 177, 243 and 334

ng/g FW in free, ester, glycoside and

ester-bound forms, respectively. In the

seeds six HBAs (gallic, protocatechuic, p-

hydroxybenzoic, vanillic, syringic and

O

OH

O

O

HO

O

HO

OH

(d) Syringic Acid (e) p-hydroxybenzoic Acid

Figure -2: Chemical structures of some hydroxybenzoic acids



salicylic acid) were identified and

quantified at concentration of 90.9, 45.5,

208 and 831 ng/g DW in free, ester,

glycoside and ester-bound forms,

respectively. All the fractions were able to

scavenge DPPH radical and their

antioxidant activities were found to be

highly correlated with their total phenolic

contents. Various phenolic acids like

gallic acid, protocatechuic acid, p-

hydroxybenzoic acid and vanillic acid

were identified in fresh potherb mustard

(Brassica juncea, Coss.) and reported total

free phenolic acids, total phenolic acids

and total phenolic content of 84.8 ± 0.58

µg/g dry weight (DW), 539 ± 1.36 µg/g

DW, and 7.95 ± 0.28 mg/g DW

respectively [26].

Flavonoids are low molecular

weight compounds, consisting of fifteen

carbon atoms, arranged in a C6-C3-C6

configuration. Essentially the structure

consists of two aromatic rings A and B,

joined by a 3-carbon bridge, usually in the

form of a heterocyclic ring, C (Fig. 3).

The aromatic ring A is derived from the

acetate/ malonate pathway, while ring B is

derived from phenylalanine through the

shikimate pathway [30,31]. Variations in

substitution patterns to ring C result in the

different flavonoid classes. Among them,

flavonols, flavones, flavanols, flavanones,

isoflavones and anthocyanidins are

particularly important in human diet [32],

of which flavones and flavonols are the

most widely occurring and structurally

diverse [33].

Figure – 3: Generic structure of a

flavonoid molecule.

Approximately 100 flavones have been

identified in plants but they are less

common in fruits and vegetables than

flavonols. The most abundant flavones in

plants are luteolin (5,7,3’,4’-

tetrahydroxyflavone) and apigenin

(5,7,4’-trihydroxyflavone) Fig. 6. In plant

tissues, these are found conjugated to

sugars, primarily glucose, rhamnose and

rutinose. The flavonols, quercetin,

kaempferol and isorhamnetin are among

the flavonoid derivatives presnt in

Brassica species [34,35]. The presence of

flavonol glycosides, quercetin 3-O-

sophoroside, kaempferol 3-O-sophoroside

and glucosides of quercetin, kaempferol

and isoquercitrin, kaempferol 3-O-

glucoside, and kaempferol diglucoside, in

broccoli florets was reported. The

quercetin and kaempferol glycosides were

present in florets at a level of 43 and 94

μg/g DW, respectively [36]. The phenolic

fractions extracted from kale leaves (B.

oleracea), rich in quercetin and

kaempferol derivatives, effectively

inhibited the growth of Gram-positive

bacteria Staphylococcus aureus,

Enterobacter faecalis, Bacillus subtilis

and the Gram-negative bacterium

Moraxella catarrhalis, which is known to

be a major respiratory pathogen in

humans [29]. Isorhamnetin, a flavonol

aglycone, isolated from mustard leaf

showed a strong activity in reducing

serum levels of glucose in Diabetes

mellitus [37]

Anthocyanins are the most abundant

flavonoid constituent. They are known to

be potent antioxidants and consequently

show chemoprotective effects against

various cancers. Brassicaceae provide a

variety of anthocyanins. Red

pigmentation of red cabbage is due to

the presence of anthocyanins and it is

known to have more than 15 different

anthocyanins, which are acylglycosides

of cyanidin [38]. The total content of

anthocyanins in broccoli and cauliflower



was studied and it was found to be 12

and 7 µ g/g in cauliflower [39]. The seeds,

cakes and meals of B. napus L. were

investigated for condensed tannins content

and reported it to be in the range of

0.146-1.53, 1.12-1.32 and 0.59-1.19

g/100 g, respectively. It was also

shown to have good DPPH

scavenging activity [40]. In Brassicaceae

vegetables, different amounts of tannins

have been reported. Inositol

hexaphosphate (phytic acid) and

condensed tannins are reported in B.

carinata [41], both of which play an

important role in iron binding [42].

Various amounts of phytic acid, tannic

acid, and/or oxalic acid are found in

cabbage and turnip. Tannic acid was

found at 12.66 mg/g (fresh weight basis)

in cabbage. Insoluble tannins

predominated in canola/rapeseed hulls and

comprised 70% to 95.8% of total

tannins present. The amounts of

sodiumdodecyl-sulphate-extractable

tannins were comparable to those of

soluble tannins but constituted only

4.7% to 14.1% of insoluble tannins

present [43].

3. Sulphur compounds in Brassicacea

Glucosinolates (GSLs) are an important

group of phytochemicals present in

abundance in the family Brassicaceae.

Chemically, glucosinolates (Fig-4) are

glucose and sulphur-containing organic

compounds whose decomposition

products are produced when plant cells

are ruptured, and the glucosinolates

present in vacuoles are hydrolysed by

the enzyme myrosinase (β-

thioglucosidase glucohydrolase. These

hydrolysis products include substituted

isothiocyanates, nitriles, thiocyanates,

epithionitriles and oxazolidinethiones,

which vary depending on the plant

species, side- chain substitution, cell pH

and cell iron concentration [44,45].

Many glucosinolate degradation

products are of interest because of their

biological activities. Several of these

hydrolysis products have biocidal

activity against a wide variety of

organisms, such as insects, plants, fungi

and bacteria [46], while others like

isothiocyanates have cancer

chemoprotective attributes [47].

Figure-4: Basic structure of

glucosinolates GSLs and their hydrolysis products are

considered as indirect antioxidants, as

they are not involved in the

scavenging of free radicals directly, but

rather by modulating the activity of

xenobiotic metabolizing enzymes,

phase I and phase II enzymes that

trigger the antioxidant activity. The

inhibition of phase I and induction

of phase II enzymes are necessary for

the protection of cells against DNA

damage by carcinogens and reactive

oxygen species [48].

3.1 Bio-protective effects of

glucosinolates and their derivatives

The up-regulation of cytochrome P450

and phase II enzyme systems was

studied by intact glucosinolates,

glucoraphanin and glucoerucin isolated

from cruciferous vegetables. It was

reported that on incubating the

precision-cut rat lung slices with the

isolated glucosinolates (1–25µ M) with

for 24 h, the GSLs modulated the

activity of pulmonary carcinogen-

metabolising enzyme systems, and thus

contributes to the documented

chemopreventive activity of cruciferous

vegetables in the lung [49].

The effect of glucosinolates and their

isothiocyanate (ITC) derived products on



in vitro cell growth of human erythroleu-

kemic K562 cells was studied using two

different approaches of in vitro

antiproliferative assays, namely in situ

and pre mix method. Among the various

GSLs and their ITCs studied the ITCs

generated from Sinigrin (SNG) and

Glucotropaeolin (GTP) appeared to be

the most active compounds, producing a

50% cell growth inhibition at a

concentration of 100 µ M. It was

revealed that the compounds studied

possess strong antiproliferative activity

against human erythroleukemic K562

cells and thus it was concluded that these

compounds could be considered

potentially responsible for the reduction

of colorectal cancer [50]. Another

isothiocyanate, sulforaphane (4-

methylsulfinylbutyl isothiocyanate)

(SFN), has recently aroused interest as a

possible cancer-preventive agent. The

chemoprotective effects of sulforaphane

are due to its ability to behave as an

inducer of phase II detoxification

enzyme [51].

It has also been shown that SFN inhibits

CYP2EI isoenzyme of the cytochrome

P450, thus emerging as an inhibitor of

phase I enzyme [52]. The SFN content

of various crucifer vegetables was

assessed in parallel to their anticancer

and antioxidant activity. Among the

tested crucifers, cabbage demonstrated a

pronounced anticancer effect against A-

549 lung cancer cells, with an IC50 value

of 38 µ g/ml, and correlated with high

SFN levels at 540 µ g/g. Though, the

crucifer extracts displayed moderate to

weak activity in scavenging 2,2-

diphenyl-1-picrylhydrazyl (DPPH) free

radical [53]. The inhibition of

proliferation of cultured PC-3 human

prostate cancer cells by SFN has been

reported by inducing apoptosis [54].

Glucosinolates are derived from amino

acid biosynthesis and are important

secondary metabolites in Brassicaceae

family, involved in plant defence

against pests and diseases [55]. For

example, glucoiberin, glucoraphanin,

glucoalyssin, gluconapin,

glucobrassicanapin, glucobrassicin,

gluconasturtiin and neoglucobrassicin

are health-promoting compounds

found in broccoli inflorescences (B.

oleracea L., var. italica, cv. Marathon)

[56]. Glucosinolates are also

responsible for the bitter acidic flavours

of Brassica species and their hydrolysis

by-products, such as isothiocyanates,

nitriles, and thiocyanates, are

responsible for the hot and pungent taste

[57]. The breakdown products of

glucosinolates assist in the activity of

important naturally occurring, direct-

acting antioxidants such as tocopherols

and also enhance the synthesis of

glutathione, one of the most abundant

intracellular direct antioxidants [58,59].

Different antioxidant compounds

(indolacetonitrile, S-1-methoxy-1-

(3,5-dimethox--4-hydroxyphenyl)

ethane, 4- hydroxy-phenyl-acetonitrile,

and 4- hydroxyl-phenyl-acetonitrile)

were isolated from rapeseed oil

cake (Brassica campestris L. subsp.

napus), which showed a strong

antioxidant activity as evaluated by the

ferric thiocyanate method [60]. Certain

glucosinolates, particularly the

isothiocyanates and nitriles, have

been shown to modify both xenobiotic

metabolizing enzymes and induce cell

cycle arrest and apoptosis and results in

chemo-preventive characteristics of

Brassica [61,62]. Another naturally

occurring isothiocyanate, sulforaphane,

that is present in the Brassica species

has been shown to block the

formation of tumors [63] and when

present together with 7-

methylsulfinylheptyl isothiocyanates in

broccoli (B. oleracea var. italica)



extract it exhibited an inhibitory effect

on 12-O- tetradecanoylphorbol-13-

acetate-induced cancer cell invasion and

matrix metalloproteinase-9 activity in

human breast cancer cells [64] and

lowers the probability of acquiring colon

and rextal cancers [65]. The effect of

Sulforaphane on the immune system was

studied using BALB/c mice and it was

demonstrated that sulforaphane is a

potent immunomodulator as it

stimulated humoral as well as cell

mediated immune system with enhanced

stem cell proliferation and differentiation

and suppressed TNF-a, a

proinflammatory cytokine, chronic

production of which is undesir-able as it

promotes tumour progression [66].

Naturally, the wide range of

glucosinolate content among Brassicacea

would result in significant differences in

their health-promoting properties [67].

4. Conclusion

It can be concluded that members of

family Brassicacea are rich food sources

of natural antioxidants and essential

nutrients, and has strong potential to

combat oxidative stress and, thus act as a

strong anticancerous as well as

antidegenerative foods.

Conflict of interest statement: We

declare that we have no conflict of

interest.

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Cite this article as: Savinder Kaur Mann and Namita Khanna. Health Promoting Effects of

Phytochemicals from Brassicaceae: A Review. Indian J. Pharm. Biol. Res. 2013; 1(3):120-131.

All © 2013 are reserved by Indian Journal of Pharmaceutical and Biological Research.

Health Promoting Effects of Phytochemicals from Brassicaceae A Review

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