Ethnopharmacological and Phytochemical Review of Garlic) From Southern Africa

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ETHNOPHARMACOLOGICAL AND PHYTOCHEMICAL REVIEW OF

ALLIUM SPECIES (SWEET GARLIC) AND TULBAGHIA SPECIES (WILD


GARLIC) FROM SOUTHERN AFRICA
SL Lyantagaye
Department of Molecular Biology and Biotechnology, College of Natural and Applied Sciences,
University of Dar es Salaam, P.O. Box 35179, Dar es Salaam, Tanzania.
E-mail: slyantagaye@gmail.com, lyantagaye@amu.udsm.ac.tz, Phone: +255-787537030

ABSTRACT
Tulbaghia (wild Garlic) is a plant genus most closely related to the genus Allium both in the
family Alliaceae and is entirely indigenous to Southern Africa. Indigenous people use several
species of the genus as food and medicine, and few species are commonly grown as ornamentals.
Biological and pharmacological research on Tulbaghia species and their relationship with
Allium sativum (sweet Garlic) are presented and critically evaluated. Informations from studies
on the treatment of microbes-caused diseases as well as of cancer have been presented in
ethnobotanical reports. Moreover, recent scientific studies have been performed on crude extracts
for certain Tulbaghia species as reviewed in this article. This article gives a critical assessment
of the literature to date and aims to show that the pharmaceutical potential of the members of
the genus Tulbaghia is comparable to that of its close relative A. sativum but has been
underestimated and deserves closer attention.

Keywords: Allium sativum, Ethnobotany, Ethnopharmacology, Medicinal, Phytochemical,


Southern Africa, Tulbaghia

INTRODUCTION species of Tulbaghia have been reported in


Tulbaghia (wild Garlic) is a plant genus scientific literature as ethnobotanically used
belonging to the family Alliaceae and is a or phytochemically investigated. However,
small plant genus of about 30 species all significant information on chemical profile
indigenous to the Southern Africa region is available only for one species, Tulbaghia
(Williamson 1955, Vosa 1975, Tredgold violaceae, and has been found to be rich in
1986, van Wyk and Gericke 2000, Figure 1) sulfur–containing compounds; the
and is very interesting from both biological compounds in most cases account for the
and chemical perspective. Some member characteristic odours and the medicinal
species have been able to adopt foreign properties of both the Tulbaghia and Allium
environmental conditions as they are being species. This review will focus mainly on
grown in as far as Europe and America the genus T u l b a g h i a and its
(Benham 1993). Most of its member species ethnopharmacological relationship with
are closely related to Allium sativum (sweet Allium.
Garlic) and hence commonly known as wild
garlic. There are many chemical constituents The Alliaceae family
that have been identified in the Alliaceae Alliaceae is a family of herbaceous perennial
family. The strong onion or garlic smells are flowering plants, which are monocots in the
found in the Tulbaghia and Allium genera, order Asparagales. The family has been
while steroidal saponins are found in most widely but not universally recognized, in the
of the species (Dahlgren et al. 1985). The past, the plants involved were often treated
medicinal uses of the Allium plants have as belonging to the family Liliaceae. The
been widely studied and recorded (Ross Angiosperm Phylogeny Group II system
2003). Only 3 of the 30 distinguished (APG II system) of 2003 recognizes the
Tanz. J. Sci. Vol. 37 2011

family and places it in the order Asparagales in the clade monocots.

Figure 1: A map showing countries (Southern Africa) where Tulbaghia plants are indigenous.

The Alliaceae family has about 600 species Genetical relationship between the genera
in 30 genera and is a widely distributed Tulbaghia and Allium
family (APG 2003). The major places of The physical ends o f eukaryotic
distribution for the whole family are chromosomes are protected from being
Mediterranean Europe, Asia, North and recognised and processed as DNA breaks by
South America and Sub-Saharan Africa telomeres. Tandemly repeated short
(APG 1998, APG 2003). The Sub-Saharan minisatellite motif of DNA is usually found
Africa genera are Allium, Tulbaghia and in the telomeres and is called telomeric
Agapanthus (Dahlgren et a l . 1985). DNA repeats. Telomere repeats are
Probably the most popular genus is Allium, remarkably conserved among eukaryotes,
which includes several important food and sequence variation among most of the
plants, including garlic (A. sativum and A. major taxonomic groups does not exceed
s c o r d o p r a s u m ), onions (Allium cepa), one or two nucleotides (Li et al. 2000). In
chives (A. schoenoprasum), and leeks (A. plants this particular motif (5’-TTTAGGG-
p o r r u m ). A strong "oniony" odour is 3’) was first characterised in Arabidopsis
characteristic of the whole genus Allium, but thaliana (Richards and Ausubel, 1988) and
not all members are equally flavorful has since been found in the majority of plant
(Kourounakis and Rekka 1991). A. sativum species (Cox et al. 1993) and is now refered
and Allium cepa are worldwide known for to as the Arabidopsis cap.
their medicinal use (Ross 2003).
However, not all plants share the typical
plant telomere sequence and recently the

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Lyantagaye – Ethnopharmacological and phytochemical review of Allium and Tulbaghia …

presence of this or its variation has been sulfides, propionthiol and vinyl disulfide in
used to show genetic similarity. Allium, their essential oils (Dahlgren et al. 1985).
T u l b a g h i a and N o t h o s c o r d u m (family
Alliaceae) are devoid of the Arabidopsis- A. sativum and its extracts have been widely
type telomeres (Fay and Chase 1996). Aloe recognized worldwide as agents for
(Asphodelaceae) and H y a c i n t h e l l a prevention and treatment of cardiovascular
(Hyacinthaceae), both belonging to and other metabolic diseases,
Asparagales, possess human/vertebrate-type atherosclerosis, hyperlipidemia, thrombosis,
sequences (5’-TTAGGG-3’) at their hypertension, microbial infections, asthma,
chromosome termini (Puizina et al. 2003, and diabetes (Reuter 1995, Reuter et al.
Weiss and Scherthan 2002). As all these 1996). The therapeutic properties of A.
genera are petaloid monocots in the sativum have been through review in the
Asparagales, it suggests that an absence of book called Medicinal Plants of the World
A r a b i d o p s i s -type telomeres may be (Humana) by Ross (2003).
characteristic of this related group of plants
(Adams et al. 2000, Weiss-Schneeweiss et The chemistry of Allium species
al. 2004). The only other plant genera so far The active components of A. sativum
reported without such telomeres are Cestrum include antioxidants such as organosulfur
and closely related genera Vestia and Sessea compounds, free radicals scavenger
(Solanaceae) (Sykorova et al. 2003). A. cepa flavonoids such as allixin, trace elements
(Alliaceae) lacks both Arabidopsis-type and such as germanium (normalizer and
human-type telomeres; it possesses an immunostimulant), selenium (for optimal
unknown type of telomere. (Sykorova et al. function of the antioxidant enzyme
2006). However, there exist significant glutathione peroxidase), volatile oil
differences between members of Allium and containing sulfur compounds, amino acids
that of Tulbaghia. For example, A. sativum and other bio-active compounds (Ross
has 2n = 3x = 24 and T. violacea has a non- 2003). Garlic chemistry is complex, and a
bimodal karyotype (2n = 12) (Fay and number of other compounds are also
Chase 1996), which is not suprising for produced in the plant by the aging process.
different species. As simply stated, organosulfur compounds
are organic molecules that contain the
Therapeutics of Allium species element sulfur. Depending on structure, the
The genus Allium has about 1250 species, presence of sulfur in an organic molecule is
making it one of the largest plant genera in often indicated by a distinctive and
the world (Dahlgren et al. 1985). The plants oftentimes unpleasant and ‘loud’ odour.
can vary in height between 5 cm and 150 However, organosulfur compounds can also
cm. The flowers form an umbel at the top of confer pleasant odour characteristics, as is
a leafless stalk. A. sativum is indigenous to observed in garlic and onions. The aroma
Asia and probably the most widely used and flavor molecules in garlic and onions are
herb in the world (Hyams 1971), but it has derived from precursor compounds that are
been grown in most of tropical and derivatives of the amino acid cysteine.
subtropical region. A. sativum has linear
sheathing leaves, globose umbels of white A. sativum and A. cepa (onion) both contain
or reddish flowers. The bulbs are composed 1-5% dry weight of cysteine derivatives in
of “cloves”, which are wrapped in a shared which the proton at sulfur in cysteine is
whitish papery coat. The odour is weak replaced with an alkyl or alkenyl
when the plant is intact, when damaged the substituent, and the sulfur atom is itself
smell grows strong. They are perennial oxidized to the sulfoxide. The cysteine
bulbous plants containing mostly sulfoxide derivatives found in onions and
organosulfur compounds, such as allyl garlic are indicated in (Figure 2, Scheme 1).

60
Tanz. J. Sci. Vol. 37 2011

Onions contain propiin, isoalliin and Hornícková et al. 2010). Alliin exhibits
methiin, whereas garlic contains isoalliin, considerable biological activity
methiin and alliin (Ichikawam et al. 2006, (Kourounakis and Rekka 1991).

O O

S OH S OH

O NH2 O NH2

Methiin
Alliin

O O

S OH S OH

O NH2 O NH2

Isoalliin Propiin

Figure 2: Cysteine sulfoxide (organosulfur) derivatives found in onions and garlic.

O O O
O OH O OH O OH
S OH S OH S OH
O HN O HN O HN
NH2 NH2 NH2
O O O
!-L-Glutamyl-S-(2-propenyl)-L-cysteine (GSAC) !-L-Glutamyl-S-(trans-1-propenyl)-L-cysteine (GSPC) !-L-Glutamyl-S-methyl-L-cysteine (GSMC)

!-Glutamyl transpeptidase !-Glutamyl transpeptidase !-Glutamyl transpeptidase

Oxidase Oxidase Oxidase

O O O

S OH S OH S OH
O NH2 O NH2 O NH2
(+)-S-(2-propenyl)-L-cysteine sulfoxide (Alliin) (+)-S-(trans-1-propenyl)-L-cysteine sulfoxide (Isoalliin) (+)"S-Methyl-L-cysteine sulfoxide (Methiin)

Scheme 1: Biosynthetic pathway of organosulfer compounds in garlic (Ichikawam et al. 2006).

The distinct flavors of garlic and onion sulfoxide derivatives are contained in the
reflect varying amounts of cysteine cytoplasm of the plant cells. In the vacuoles
sulfoxides in each plant, most particularly of these cells is contained a class of enzymes
isoalliin (higher amount in onion) and alliin known as C-S lyases. If the plant tissue is
(higher amount in garlic) (Fritsch and disrupted by cutting/slicing, chopping,
Keusgen 2006). Isoalliin is the precursor of chewing etc, the C-S lyase is released, and it
thiopropanal S-oxide, the volatile sulfine in subsequently acts upon the cysteine
onion that causes tearing. The cysteine sulfoxide derivatives, cleaving the C-S bond

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Lyantagaye – Ethnopharmacological and phytochemical review of Allium and Tulbaghia …

between the b-carbon and sulfur (Scheme 2). antiviral and anticancer properties, among
This cleavage results in two fragments; a others (Ross 2003). Thiosulfinates also
putative sulfenic acid intermediate, and a- serve as the primary flavor and odour
aminoacrylic acid (Block 1992, Shimon et producing molecules in freshly prepared
a l . 2007). The latter compound garlic and onion macerates. The
spontaneously decomposes to ammonia and thiosulfinates participate in a variety of
pyruvic acid while the former condenses subsequent reactions which afford a
with a second sulfenic acid molecule to form considerable number of organosulfur
a class of compounds known as volatiles, such as sulfides, di- and trisulfides
thiosulfinates (Block 1992, Shimon et al., and dithiins (Figure 3). These compounds
2007). The importance of the thiosulfinates impart additional flavor, odour and
derivatives is from the fact that they have biological activity characteristics to longer
been shown to exhibit a variety of biological standing and/or heat-treated macerates.
activities, including antibacterial, antifungal,

Scheme 2.: Proposed general mechanism for the catalysis of C-S bond cleavage in Cys
sulfoxide derivatives by alliinase (Block 1992, Shimon et al. 2007). Alliin, S-
Allyl-L-Cys sulfoxide; 2-hydroxyethiin, S-2-hydroxyethyl-L-Cys sulfoxide;
isoalliin, (E)-S-(1-propenyl)-L-Cys sulfoxide; methiin, S-methyl-L-Cys sulfoxide;
petiveriin, S-benzyl-L-Cys sulfoxide; propiin, S-propyl-L-Cys sulfoxide.

Because earlier studies established that the the A l l i u m genus whose organo-leptic
aforementioned chemistry occurred in garlic properties imply the presence of
and onions, and since both are members of organosulfur compounds (Block 2010).
the allium family, this chemistry is often Indeed, in the next sections it is shown that
referred to as ‘allium chemistry’. However, similar chemistry occurs in T. violacea.
there are numerous other plants unrelated to

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Tanz. J. Sci. Vol. 37 2011

Figure 3: A, therapeutically active sulfur compounds from garlic; a representative for each of
the three substance classes (allyl sulfides, dithiines, and ajoenes) is shown. B, the
enzymatic reaction catalyzed by alliinase (Kuettner et al. 2002).

species are reported in the UK, such as T.


Tulbaghia species violacea, T. cominsii, T. acutiloba, T.
Of all the members of the family Alliaceae, natalensis, and T. montana, and also in the
Tulbaghia is the genus most closely related USA cultivated as decorative plants
to Allium and is entirely indigenous to although most are rather tender and are best
Southern Africa (Figure 1). The natural grown as warm greenhouse plants (Burbidge
distribution extends from Southern Tanzania 1978, Watson and Dallwitz 1992).
to Malawi, Botswana, Zimbabwe, Typically, the Tulbaghia species are
Mozambique, South Africa, Swaziland and modest, unassuming plants with small
Lesotho (Williamson 1955, Vosa 1975, flowers, grassy foliage, sometimes with a
Tredgold 1986, van Wyk and Gericke 2000, pungent skunky or alliaceous scent to the
Vosa and Condy 2001). Indigenous people rhizomatous rootstalks. A new species of
use several species as food and medicine, Tulbaghia (T. pretoriensis), sympatric to
and few species are commonly grown as Tulbaghia acutiloba and found in and
ornamentals (Vosa 1975, Vosa and Condy around Pretoria was the latest to be
2001). T. violacea is the most well known described in 2006. The two species differ
species as medicinal plant species in the from one another in their karyotype, flower
genus, especially in the Eastern Cape and morphology and scent, as well in their
KwaZulu-Natal regions (Burton 1990, van overall size (Vosa and Gillian 2006, Vosa
Wyk et al. 2000). The presence of this 2007). Table 1 shows members on record of
species elsewhere is due to cultivation in the small genus Tulbaghia, about 30 plants
gardens and in the commercial medicinal species.
plant farms (van Wyk et al. 2000). A few

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Lyantagaye – Ethnopharmacological and phytochemical review of Allium and Tulbaghia …

Table 1: Plant species in the genus Tulbaghia (Burbidge 1978, Vosa 1980, Vosa 2000, Vosa
and Condy 2006)
Species Common name [local names]
Tulbaghia pretoriensis Vosa & Condy. Wild Garlic
Tulbaghia acutiloba Harv. Wild Garlic, Wildeknoffel [Afrikaans], sefothafotha
[South Sotho], lisela [Swazi], ishaladi lezinyoka
[Zulu].
Tulbaghia aequinoctialis Welw. ex Baker Wild Garlic
Tulbaghia affinis Link Wild Garlic
Tulbaghia alliacea L.f. Wild Garlic
Tulbaghia bragae Engl. Wild Garlic
Tulbaghia calcarea Engl. & K.Krause Wild Garlic
Tulbaghia cameronii Baker Wild Garlic
Tulbaghia capensis L. Wild Garlic, Wildeknoffel [Afrikaans],
Tulbaghia coddii Vosa & Burb. Wild Garlic
Tulbaghia cominsii Vosa Wild Garlic
Tulbaghia dregeana Kunth Wildelook, Ajuin [Afrikaans]
Tulbaghia friesii Suess. Wild Garlic
Tulbaghia galpinii Schltr. Wild Garlic
Tulbaghia hypoxidea Sm. Wild Garlic
Tulbaghia leucantha Baker Wild Garlic, sefothafotha [South Sotho]
Tulbaghia ludwigiana Harv. Scented Wild Garlic, ingotjwa, sikwa [Swazi],
umwelela-kweliphesheya [Zulu]
Tulbaghia luebbertiana Engl. & K.Krause Wild Garlic
Tulbaghia macrocarpa Vosa Wild Garlic
Tulbaghia montana Vosa Wild Garlic
Tulbaghia natalensis Baker Sweet Wild Garlic, iswele lezinyoka [Zulu]
Tulbaghia nutans Vosa Wild Garlic
Tulbaghia pauciflora Baker Wild Garlic
Tulbaghia rhodesica R.E.Fr. Wild Garlic
Tulbaghia simmleri P.Beauv. Wild Garlic
Tulbaghia tenuior K.Krause & Dinter Wild Garlic
Tulbaghia transvaalensis Vosa Wild Garlic
Tulbaghia verdoornia Vosa & Burb. Wild Garlic
T. violacea Harv. Wild Garlic, Wildeknoffel [Afrikaans], isihaqa [Zulu]
Tulbaghia x aliceae Vosa Wild Garlic

T. violacea is a small perennial bulbous 1992). The plant gives out a strong odour of
herb with corm-like rhizomes and narrowly onion or garlic when bruised (Watt and
linear, evergreen aromatic leaves. The Breyer-Brandwijk 1962), hence its common
flowers are tubular mauve or pale purple, names wild garlic (van Wyk et al. 2000) or
occurring in groups of about ten at the tip of society garlic (Watson and Dallwitz 1992).
the slender stalk (Figure 4). The plant Inspite of its garlic-like flavor, the
prefers partial shade or partial sun to full consumption of T. violacea is not
sun; and dry to moist soils. Mature height accompanied by the development of bad
ranges from 30 cm to 120 cm depending on breath as is in the case with the
the environmental conditions. The plant can consumption of A. sativum and hence
be grown successfully in a tub and another common name “sweet garlic” (Kubec
transferred to a greenhouse or a frost-free et al. 2002). This suggests that T. violacea
place for the winter (Watson and Dallwitz and A. sativum may not contain exactly the

64
Tanz. J. Sci. Vol. 37 2011

same volatile chemical compositions. A l l i u m volatile compounds. Thus,


However, it was previously reported that T. suggesting that the garlic-like smell of the
violacea contain a carbon-sulfur lyase wild garlic is most likely due to the same or
enzyme whose action is similar to that of similar sulfur compounds (Burton 1990). It
lyases in the various A l l i u m species is, therefore, most likely that T. violacea
(Jacobsen et al. 1968). The same study may also contain the medicinal potential
suggested the presence of sulfur compounds that is similar to its close relative A.
that corresponded with those found in sativum .

a b

Figure 4: Tulbaghia violacea; a) whole plants, and b) flower,

Ethnobotany of Tulbaghia species Some of the Rastafarians eat copious


The traditional uses of Tulbaghia species are amounts of it and chili during winter
referred to in many folkloric and allegedly “to keep the blood warm” and stop
ethnobotanical studies performed in certain aches and pains. Bulbs and leaves soaked in
areas of South Africa, where like many other water for a day can be used for rheumatism,
the poor Sub-Saharan Africa communities, arthritis and to bring down fever. The bulbs
plants are still the primary source of are also used for coughs, colds and flu. Zulu
medicine. people also use the plant to repel snakes
away from their houses. It is also used for
According to van Wyk et al. (2000), T. the treatment of infant and mother in the
violacea [common names: Wild garlic case of depressed fontanelle. In the Eastern
(English), Wildeknoffel (Afrikaans), Isihaqa Cape T. violacea is used for colic, wind,
(Zulu) and Moelela (Sotho)] is used in restlessness, headache and fever, largely for
traditional medicine in the Eastern Cape and young children. Like any drug, extensive
KwaZulu Natal for problems like fever, use can give adverse symptoms such as
colds, asthma, tuberculosis, stomach-ache, abdominal pain, gastroenteritis, acute
and cancer of the oesophagus. The bulbs of inflammation and sloughing of the intestinal
T. violacea are used as a remedy for mucosa, cessation of gastro-intestina
pulmonary tuberculosis and to destroy peristalsis, contraction of the pupils and
intestinal worms. The Zulu people use the subdued reactions to stimuli. Tulbaghia
bulb to make an aphrodisiac medicine. simmeleri is often used as alternative for T.

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Lyantagaye – Ethnopharmacological and phytochemical review of Allium and Tulbaghia …

violacea, where the latter is not available literature about the rest of the plant species,
(Burton 1990, van Wyk et al. 2000). most probably they are used interchangeably
with T. violacea, T. simmleri, and T .
Tulbaghia alliacea, has been reported as an alliacea.
early Cape remedy for fever, fits,
rheumatism, and paralysis (Burton 1990). T. Chemical constituents of Tulbaghia
alliacea has the same common name as T. species
v i o l a c e a , i.e., Wild garlic (English), Like in Allium, volatile sulfur-containing
Wildeknoffel (Afrikaans), Isihaqa (Zulu) and flavor compounds are responsible for the
Moelela (Sotho). T. alliacea is an characteristic smell and taste of Tulbaghia
indigenous species in South Africa, growing species. Unlike Allium species, the closely
particularly in the Eastern Cape and southern related plant whose chemistry has been
KwaZulu-Natal. It is a bulbous plant with extensively studied, only few scientific
long, narrow, hairless leaves arising from articles about the chemical constituents of T.
several white bases. Brownish green flowers v i o l a c e a have been published so far.
occur in-groups of about 10 or more at the Jacobsen et al. (1968) reported the presence
tip of a slender stalk (Robert 2001). Both of a C–S lyase and three unidentified S-
the bulbs and leaves of T. alliacea are used substituted cysteine sulfoxide derivatives.
medicinally. In Zimbabwe and South Africa Bate-Smith (1968) reported the presence in
the leaves of Tulbaghia alliacea are cooked T. violacea of kaempferol (Figure 5). Burton
as a relish, alone or with leaves of other and Kaye (1992) isolated 2,4,5,7-
plants, such as Adenia species. The rhizome tetrathiaoctane-2,2-dioxide and 2,4,5,7-
is scraped clean and boiled with meat in tetrathiaoctane from the leaves of T.
stews or roasted as a vegetable. Young violacea. Kubec et al. (2002) isolated
leaves are chopped and used to flavour 2,4,5,7-tetrathiaoctane-4-oxide and identified
soups, stews, pickles and omelettes as a the three unknown cysteine derivatives that
substitute for shallot. In South Africa the had been suggested by Jacobsen et al. (1968)
bruised rhizome is used in baths for the as (RSRC)-S-(methylthiomethyl)cysteine-4-
relief of fever, rheumatism or paralysis. oxide (marasmin). (SSRC)-S-methyl- and
Small doses are used as a laxative (SSRC)-S-ethylcysteine sulfoxides (methiin,
(Williamson 1955, Vosa 1975, Tredgold MCSO and ethiin, ECSO, respectively).
1986, van Wyk and Gericke 2000). The Gmelin et al. (1976) were the first to
plant is used for fever and colds, asthma, propose that the enzymatic cleavage of
pulmonary tuberculosis and stomach marasmin is analogous to that of alliin (S-
problems. In the Cape Dutch tradition, T. allylcysteine sulfoxide) in A. sativum and
alliacea is used as a purgative and for fits, other alliaceous species. They suggested the
rheumatism and paralysis. Also tea can be formation of S - ( m e t h y l t h i o m e t h y l )
made from chopped bulbs and roots and (methylthio) methanethiosulfinate (2,4,5,7-
used as a purgative. Extracts of T. alliacea tetrathiaoctane-4-oxide, marasmicin, 2 in
exhibit anti-infective activity against Sheme 3) from marasmin as the primary
Candida species in vitro (Thamburan et al. breakdown product.
2006). The Khoikhoi and Basotho use the
plant to make a brew from the chopped The presence of a C–S lyase in T. violacea
bulbs and roots (Robert 2001). (Jacobsen et al. 1968), suggests the close
genetic relationship with Allium species,
The bulbs of Tulbaghia cepacea are also due to marasmicin being in close
recommended for tuberculosis and as an analogy to the alliin/allicin system, make it
anthelmintic (Watt and Breyer-Brandwijk reasonable to assume that a similar
1 9 6 2 ) . Nothing has been reported in mechanism is also operating in T. violacea.

66
Tanz. J. Sci. Vol. 37 2011

6
CH2OH
5
O
H
H H
4
1
OH H
OH OCH3
3 7
2
H OH
Figure 5: Kaempferol Figure 6. Methyl-%-D-glucopyranoside
(MDG).

O
O H NH2
S S C-S lyase S SOH - 1/2 H2O S S
COOH S S

(RSRC)-S-(methylthiomethyl)cysteine-4-oxide, 1 marasmicin, 2

Scheme 3: Formation of marasmicin, 2, from (RSRC)-S-(methylthiomethyl)cysteine-4-oxide, 1,


in T. violacea.

Marasmicin is unstable and further S-alk(en)yl cysteine sulfoxides,


decomposes giving various sulphur- thiosulfinates, polysulfides, fructose and
containing degradation products, e.g. glucose compounds have been found from
2,4,5,7-tetrathiaoctane, 2,4,5,7- the aqueous extract T. alliacea. Also, a
tetrathiaoctane-2,2-dioxide, 2,4,5,7- furanoid compound [5-(hydroxymethyl)-2-
tetrathiaoctane-4,4-dioxide, or 2,4,5,7- furfuraldehyde] was identified as an artefact
tetrathiaoctane-2,2,7,7-tetraoxide (Kubec et compound generated by the acid hydrolysis
al. 2002). Other classes of compounds step. This compound occurs as a product
reported in T. violacea are flavonols e.g. from the acid-catalyzed dehydration of
kaempferol (Figure 5), and fructose (Maoela 2005).
saponins/sapogenins, which are generally
present in Allium and Tulbaghia (Watson Krest et al. (2000) reported the presence of
and Dallwitz 1992). Burton (1990) S- methyl-L-cysteine sulfoxide (MCSO,
identified free sugars including glucose, methiin), S-propyl cysteine sulfoxide
fructose, sucrose, maltose, arabinose, (PCSO, propiin), S-allyl-L-cysteine
rhamnose, xylose and galactose, and sulfoxide (ACSO, alliin) and S- (trans-1-
glycosides from an aqueous extract of T. propenyl)-L-cysteine sulfoxide (PeCSO,
violacea. Lyantagaye and Rees (2003) and isoalliin) in considerable amounts in T.
Lyantagaye et al. (2005) have reported the acutiloba. These compounds have been well
presence of glucopyranoside “Methyl-%-D- known to occur in most Allium species.
glucopyranoside (MDG)” (Figure 6) from T. Also, the presence of lectin-like proteins
violacea aqueous extracts. have been reported more than once

67
Lyantagaye – Ethnopharmacological and phytochemical review of Allium and Tulbaghia …

(Gaidamashvili and van Staden 2002a, Kaempferol consumption in tea and broccoli
2002b, 2006). has been associated with reduced risk of
heart disease (Park et al. 2006).
Bioactivity of Tulbaghia species extracts
The compounds 2,4,5,7-tetrathiaoctane-2,2- More studies have also shown that extracts
dioxide and 2,4,5,7-tetrathiaoctane from the from Tulbaghia species control plant fungal
leaves of T. violacea, reported by Burton pathogens by inhibiting their growth
and Kaye (1992), were found to have (Lindsey and van Staden 2004, Vries et al.
antibacterial activity (Burton 1990). Crude 2005, Nteso and Pretorius 2006).
aqueous extracts from T. violacea have been Gaidamashvili and van Staden (2002a,
shown to exhibit apoptosis inducing ability, 2002b, 2006) reported the isolation of
and so the extacts contain potentially lectin-like proteins and their prostaglandin
anticancer agents (Lyantagaye and Rees, inhibitory activity and Staphylococcus
2003). Two years later, Lyantagaye et al. aureus a n d Bacillus subtilis growth
(2005) remarked on the promising anticancer inhibition. There have also been roports on
activities of T. v i o l a c e a - derived the potential anti-infective remedy for fungal
compounds containing a methyl-%-D- infections (Motsei 2003, Bull et al. 2005,
glucopyranoside (MDG) moiety in their Thamburan et al. 2006). ACE inhibitor
structure (Figure 6). The MDG structure has activity and lowering of blood pressure and
been postulated to interfere with the bio- down regulating of AT1a gene expression in
activities of hexokinase, as well to induce a hypertensive rat model have been reported
reactive oxygen species, which cause cellular (Mackraj and Ramesar 2007, Mackraj et al.
damage and hence apoptotic cell death 2007). More recently, Ebrahim and Pool
(Cohen et al. 2002, Pastorino et al. 2002, (2010) reported that T. violacea has
Lyantagaye 2005). This was the first time T. androgenic properties; treatment of cells
violacea – derived MDG was reported to kill with T. violacea increased LH-induced
cancer cells by inducing apoptosis in the testosterone production.
cells. Current research efforts focus on
understanding the exact mode of action of CONCLUSION
MDG and other related plants from the the Plants are known to be important sources of
plant extracts. therapeutic agents. This implies that
compounds or mixture of compounds that
An in vitro study by Kowalski et al. (2005) have activity in mammalian cells are
showed that the flavonoid kaempferol potential therapeutic agents and can be used
inhibits monocyte chemoattractant protein as leads towards the development of new
(MCP-1). MCP-1 plays a role in the initial drugs. Only reports for biological activity of
steps of atherosclerotic plaque formation. 4 of the 29 species of Tulbaghia exist, and
The kaempferol and quercetin seems to act significant phytochemical investigations
synergistically in reducing cell proliferation have been conducted on only 1 of them.
of cancer cells, meaning that the combined Sulfur-type compounds seem to be typical
treatments with quercetin and kaempferol are for the genus as they were found from
more effective than the additive effects of several species. Among these compounds,
each flavonoid (Ackland et al. 2005). An 8- kaempferol and other sulfur compounds are
year study found that three flavonols most remarkable and have received much
(kaempferol, quercetin, and myricetin) scientific attention because of their anti-
reduced the risk of pancreatic cancer by 23 cancer potential. Clearly, members of the
percent (Nöthlings et a l . 2008). Many genus T u l b a g h i a possess significant
glycosides of kaempferol, such as pharmacological potential and promising
kaemferitrin and astragalin, have been activities of extracts in the context of
isolated as natural products from plants. ethnomedicinal knowledge, and therefore

68
Tanz. J. Sci. Vol. 37 2011

promote a high degree of interest in further families of flowering plants: APG II.
studies. Knowledge obtained from such Bot J Linn Soc 141: 399-436.
studies could also enhance the efficacy of Bate-Smith EC 1968 The phenolic
already existing ethnomedicinal uses and, constituents of plants and their
consequently, support the cultural value of taxonomic significance. J Linn Soc Bot.
these species. The T u l b a g h i a species 60: 325–83.
described in this review do not appear Benham S 1993 Tulbaghia: a survey of the
limited in their availability and might serve species in cultivation. Plantsman 15(2):
as an important source of medicine among 89–110.
people living in the Southern Africa region. Block E 1992 The organosulfur chemistry of
There is a necessity to attempt to investigate the genus Allium: Implications for the
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antifungal agents against the fumonisin
ACKNOWLEDGEMENTS producing strain, Fusarium
It would not have been possible to produce verticillioides MRCS26. South African
the review without the financial support J Sci 101, XII.
from the National Research Foundation Burbidge RB 1978 A revision of the genus
(NRF) of South Africa, Triangle Tulbaghia (Liliaceae). Notes from the
Pharmaceuticals, USA, South African Royal Botanic Garden Edinburgh. 36:
Department of Trade and Industry, Cancer 77-103.
Association of South Africa, Carnegie-IAS - Burton SG 1990 A chemical investigation of
(RISE) USA and ACP-EU funding for POL- T. violacea. MSc thesis. Rhodes
SABINA project, and the Sida/Sarec University.
through core support component at the Burton SG, Kaye PT 1992 Isolation and
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