MEDICINAL PLANTS:

Phytochemistry, Pharmacology
and Therapeutics
– Volume 3 –

Editor-in-Chief
V.K. Gupta
Chief Scientist
CSIR-Indian Institute of Integrative Medicine
Canal Road, Jammu – 180 001, India

Editors
G.D. Singh
Senior Scientist
PK-PD-Toxicology Division

Surjeet Singh
Scientist
Department of Pharmacology

A. Kaul
Scientist,
Department of Pharmacology

CSIR-Indian Institute of Integrative Medicine

Canal Road, Jammu – 180 001, India

2014
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Medicinal plants : phytochemistry, pharmacology and therapeutics / editor-in-

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1. Medicinal plants—India—Analysis. 2. Materia medica, Vegetable—India.

3. Pharmacology—India. I. Gupta, V. K. (Vijay Kumar), 1953- II. Singh, G.
D. (Gurdarshan), 1962- III. Surjeet Singh, 1958- IV. Kaul, A. (Anpurna),
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Medicinal Plants: Phytochemistry, Pharmacology Pages 213–234
and Therapeutics Vol. 3 (2014)
Editor-in-Chief: V.K. Gupta
Published by: DAYA PUBLISHING HOUSE, NEW DELHI

8
Biological Activities, Phytochemistry and
Industrial Potentials of Khaya senegalensis
(Meliaceae) A. Juss
Mohammed Auwal Ibrahim1,2 and Md. Shahidul Islam1*

ABSTRACT
Khaya senegalensis A. Juss (African mahogany) is a large tree growing mainly in the
sub-Saharan Africa and highly reputed for numerous medicinal effects. Scientific investigations
have provided evidences that the various part of the plant contained antitrypanosomal,
antiplasmodial, antihelminthic, antioxidant, antifungal, antibacterial and anticancer agents.
Other biological activities attributed to the plant are antiinflammatory, larvicidal and
immunomodulatory properties. Phytochemical analysis using different chromatographic and
spectroscopic tools revealed that the different parts of the plant contain mainly limonoids and
more than 45 have been identified so far. However, khayanolides and seneganolides are the
most commonly found limonoids among other forms and are linked to the numerous
pharmacological effects of the plant. Furthermore, phenolics such as gallic acid, rutin,
procyanidins, catechin and quarcetin have been detected in different parts of the plant. On the
other hand, the gum polymer produced by the plant had high binding (mechanical and
disintegrational) properties in tablet formulation and could serve as a binder in the
pharmaceutical industries. This review will thoroughly discuss the possible implications of
the above-mentioned findings to the pharmaceutical industries of developing countries.
Keywords: Khaya senegalensis, African mahogany, Khayanolides, Seneganolides.

———————
1 Department of Biochemistry, School of Life Sciences, University of KwaZulu-Natal
(Westville Campus), Durban, 4000, South Africa
2 Department of Biochemistry, Ahmadu Bello University, Zaria, Nigeria
* Corresponding author: E-mail: [email protected]
214 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

Introduction
Khaya senegalensis (Desr.) A. Juss, also known as African mahogany, is a member
of the Meliaceae family, within the sub tribe Swietenioideae (Styles, 1972), which
contains many of world’s most highly valued timber species (Sexton et al., 2010). The
species occurs naturally in the tropics of 19 central African countries discontinuously
from Senegal and neighboring countries in the west (mostly between about 8°N and
15°N but extending to about 6°N in Nigeria) through to Sudan and Uganda in the
east where it extends southward to about 2°45’N. This distribution covers a wide
range of climatic, altitudinal, ecological and edaphic conditions from sea level to
1800 m, encompassing mean annual rainfalls from <700 mm (under which it is often
associated with seasonal watercourses) to about 1750 mm, with dry season lengths
of 2–8 months. Also, the species occurs on a wide variety of soil types including those
within gallery forest (where it attains heights of around 35 m with a bole diameter of

Figure 8.1: A picture of Khaya senegalensis.

Medicinal and Industrial Potentials of Khaya senegalensis | 215

1.5m and length of 10 m) and drier open savanna with lateritic soils and on rocky
places where it mostly occurs as solitary trees attaining heights of 15–20 m, often
with a sinuous bole (Nikles et al., 2008).
Throughout its natural range, K. senegalensis has been exploited for timber, which
is used for fine furniture, construction, and fuel. It was one of the first west African
forest tree species to be imported by Europeans due to its excellent timber and veneer.
Furthermore, the African mahogany is now widely used in United States furniture
sector as a substitute for American mahogany. Indigenous American companies
have been keen to replace increasingly costly and scarce American mahogany with
more competitive timbers whilst also reacting to domestic and international pressures
associated with use of American mahogany from natural stands (Arnold, 2004). Due
to such factors, the United States’ imports of African mahogany (as logs and sawn
timber) increased dramatically during the 1990s – from 4,100 m 3 in 1991 to more than
20,000 m 3 in 1998 (Traffic, 2000). Also due to the increasing cost and scarcity of
American mahogany, there has been increasing interest in African mahogany from
timber importers and furniture manufacturers in China (Arnold, 2004).
On the other hand, medicinal compounds, extracted from bark, leaf, and seed,
are used to treat a multitude of tropical diseases, and its foliage is used to sustain
livestock during the dry period of the year. The dynamics of such demands coupled
with the timber demands have already led to local extinctions (especially in the north
of its range), and the species is now classified as vulnerable under the Red List of
Threatened Species (IUCN, 2010). Luckily, the demonstrated wide adaptability,
substantial yield potential and proven timber quality of African mahogany led to
various domestication and plantation programmes in some parts of Asia and
Australia (Nikles et al., 2008) which may consequently assist in the conservation of
this highly valued species.
Apart from the wood and timber uses of this plant, more relevant to this paper, is
the medicinal applications of this species in the treatment of various tropical diseases.
Almost all parts of the plant are claimed to cure many diseases prevalent in the areas
where it grows and as such, it is considered as a primary health care facility to
millions of Africans. However, this is not surprising when considering an array of
phytochemicals isolated from the different parts of the plant. In spite of the widely
use of this plant in the traditional circles and the scientifically documented evidences
on some of its pharmacological actions, there is no document that could provide an
overall picture of scientifically validated bioactivities and industrial potentials of
this plant. This chapter will examine the documented ethnobotanical uses of this
plant and systematically discuss the biological and pharmacological activities
attributed to the different parts and extracts of the plant as well as the phytochemicals
isolated from the plant. This is with a view to provide an overall medicinal and
industrial potential of this highly respected plant for possible exploitation by relevant
sectors to solve a number of agricultural, health and economic problems.

Ethnobotanical Uses of K. senegalensis

Khaya senegalensis is well known as an important medicine within the traditional
healers of West Africa for the treatment of malaria, anemia, diabetes, gastrointestinal
216 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

diseases among others. In an ethnobotanical survey, Atawodi et al. (2002) reported

that among all other plants, K. senegalensis was the most commonly used plant for the
treatment of trypanosomiasis in Kaduna state of Nigeria where the disease is
prevalent. In fact, >60 per cent of respondents in the study prescribed recipes
containing K. senegalensis. Another study from north western Nigeria also indicated
that K. senegalensis is highly ranked in the list of medicinal plants used for the
traditional management of diabetes mellitus (Etuk et al., 2010). Similarly, in a survey
of Ghanian herbal market, K. senegalensis was among the medicinal plants that had
highest market demand. Indeed, it is the fourth most commonly purchased medicinal
plant in the Ghanian market with an average daily market stock of 788 kg where the
bark is used as blood tonic, aphrodisiac and for treating fever (van Andel et al., 2012).
Reports from northern Cote-d ‘ivoire also indicate that the stem bark of K. senegalensis
is among the highly utilized medicinal plants for the treatment of wounds, diarrhoea
and dysentery (Kone et al., 2004). Furthermore, a study on herbal remedies among the
Tem tribe of Togo also suggests that K. senegalensis was among the list of plants used
to cure several diseases but unfortunately, it also tops the list of medicinal plants
with highest adverse effects (Tchacondo et al., 2011). Some of the adverse effects
linked to this plant are diarrhoea, polyuria, hunger, abdominal pains and general
weakness (Tchacondo et al., 2011). However, the reported adverse effects may be
associated to the difference in geographical location which is known to affect the
phytochemistry and hence, the biological activities of a plant material.
These reported ethnobotanical uses of the plant has attracted the attention of
scientists from different parts of the world to evaluate the plant for a variety of
pharmacological and biological activities with a view to find alternative therapies to
a number of ailments. Below, we provide a rundown of available pharmacological
activities investigated in this plant and briefly discuss all available scientific literatures
associated with the activity under study.

Antimalarial Activity of K. senegalensis

Malaria is one of the tropical diseases traditionally treated with the parts of
K. senegalensis and unfortunately only few studies have been carried out to validate
the claim. According to a study by Ndjonka et al. (2012), ethanolic extract of
K. senegalensis stem bark inhibited in vitro proliferation of Plasmodium falciparum 3D7
with an IC50 and IC90 values of 40.1 ± 4.3 µg/ml and 214.7 ± 0.3 µg/ml respectively. It
was also found to synergistically interact with an extract of Anogeissus leiocarpus (IC50
of the combination was 12.5 ± 2.7 µg/ml) to inhibit the in vitro proliferation of the
parasites which support the combination of K. senegalensis with other plants in the
traditional treatment of malaria. In order to identify the biological activity of some
limonoids isolated from K. senegalensis, other authors reported that fassinolide was
active in vitro against chloroquine sensitive strains of P. falciparum (Khalid et al.,
1998). In another study from Burkina Faso, ethanolic extract of the bark and leaves of
K. senegalensis inhibited in vitro maturation of fresh clinical isolates of P. falciparum
with IC50 values of 82.17 µg/ml and 58.48 µg/ml respectively (Karou et al., 2003).
Although these authors did not appreciate the observed antiplasmodial activities of
K. senegalensis extracts when considering other plants used in the study but postulated
Medicinal and Industrial Potentials of Khaya senegalensis | 217

that the traditional use of K. senegalensis parts for treating malaria could be linked to
its tendency to treat malarial symptoms like fever and does not actually mediate the
killing of the parasites. Thus, the contrasting scientific reports on the actual
antimalarial activity of K. senegalensis extracts needs further verification, especially
in an in vivo animal model.

Antihelminthic Action of K. senegalensis

Some investigators have studied the efficacy of K. senegalensis extracts against
different species of gastrointestinal nematode parasites since the plant is also used in
the traditional circles for the treatment of gastrointestinal disorders. Using sheep
with naturally acquired infection of gastrointestinal nematodes, Ademola et al. (2004)
observed that administration of 500 mg/kg body weight (bw) of ethanolic extract of
K. senegalensis stem bark caused the reduction of fecal egg count (FEC) after 2 days
and that the percentage reduction of FEC of sheep parasitized with Oesophagostomum
columbianum, Stronglyloides sp. and Trichuris sp. was 100 per cent by the third day of
administration while the percentage reduction of FEC of Haemonchus contortus and
Trichostrongylus colubriformis was 68.2 and 66.1 per cent, respectively, by the twelfth
day of administration. The study further reveals the potentials of the plant extract to
mediate the killing of both intestinal and abdominal parasite species in an in vivo
system. In another study, these authors used bioassay guided fractionation of the K.
senegalensis ethanolic extract in order to identify the possible group of bioactive
antihelmenthic agents using H. contortus as a model organism (Ademola et al., 2009).
The results indicate that the antihelminthic activity of the plant extract is due to some
synergistic relationships between saponins, terpenoids, flavonoids and condensed
tannins. Using Onchocerca ochengi and Caenorhabditis elegans as model organisms,
other workers from Cameroon and Germany reported that the stem bark K. senegalensis
ethanolic extract displayed the highest antihelminthic activity among all other tested
plants in the study (Ndjonka et al., 2011). Although limited in number, but these
scientific investigations tend to lend credence to the widely use of K. senegalensis stem
bark in the traditional treatment of gastrointestinal disorders by herdsmen. Further
studies on the subject could lead to the development of novel antihelminthic agent(s).

Antitrypanosomal Activity of K. senegalensis Parts

Antitrypanosomal effects is perhaps the most widely scientifically validated
pharmacological property of this plant extracts. In an in vitro study with Trypanosoma
brucei brucei and T. congolense, methanol extract from the bark of K. senegalensis was
found to contain the most potent trypanocidal agents among twenty three plants
harvested from the savannah belt region of Nigeria (Atawodi et al., 2003). Similarly,
Wurochekke and Nok (2004) reported that aqueous and methanol extract of the plant
had the highest in vitro activity against T. brucei brucei than other thirteen medicinal
plants used for the traditional management of trypanosomiasis in northern Nigeria.
Subsequently, an excellent in vivo activity of stem bark aqueous extract of the plant
against T. brucei was demonstrated (Ibrahim et al., 2008) where 100 mg/kg bw of the
extract completely eliminated the parasites from infected animals within three days
but unfortunately could not reverse the trypanosome-associated liver damage. These
findings support, though indirectly, another investigation from Germany where
218 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

dichloromethane extract of K. senegalensis stem bark demonstrated very high

trypanocidal activity but was also toxic to mammalian cells which makes its selectivity
index very low (Aderbauer et al., 2008). Other workers from south western Nigeria
also demonstrated that K. senegalensis extracts contain the most effective trypanocidal
agents than other ten medicinal plants from the region (Antia et al., 2009). In another
study, Adeiza et al. (2010) compared the in vitro anti-T. evansi activity of K. senegalensis
parts and found that the methanol extract of the stem bark had the highest activity.
Furthermore, ethanolic extract of the stem bark was found to inhibit the multiplication
of T. evansi in an in vivo system but could not ameliorate the parasite induced anemia
(Umar et al., 2010). It seems therefore that K. senegalensis stem bark extract contain
highly trypanocidal constituents but are not effective in ameliorating some of the
disease associated pathological changes. Identification of the active trypanocidal
agents and possible toxic components from the stem bark would certainly provide a
clue on the potential application of this plant part or its bioactive agent in the treatment
of trypanosomiasis. It is hoped that an on-going study in our lab would provide the
much needed clue on the subject.

Antibacterial Activity of K. senegalensis

Although different parts of K. senegalensis are used in the traditional treatment of
several bacterial infections but there is a dearth of scientific research on the subject.
Perhaps the first study on the antibacterial action of K. senegalensis parts was reported
by Kone et al. (2004) which demonstrated that ethanolic extract of K. senegalensis stem
bark was among the ten most active plant extracts (out of fifty) against some antibiotic
resistant bacteria strains. Subsequently, a relatively more elaborate investigation was
reported by Kubmarawa et al. (2008). These authors prepared aqueous and ethanolic
extracts from the root, stem bark and leaf of the plant and tested their antibacterial
activity using both gram positive and gram negative bacteria. Their findings revealed
that the aqueous and ethanolic extracts of the stem bark as well as the ethanolic
extract of the roots contained more potent antibacterial agents because of their ability
to inhibit all the bacteria species tested in a disc diffusion assay method. Furthermore,
a most recent study indicated that aqueous and ethanolic extracts of the root of K.
senegalensis inhibited the growth of four different species of bacteria in a punch hole
method for antibacterial testing (Ide and Igeleke, 2012). Summarily, reports on the in
vitro antibacterial activity of K. senegalensis looks promising but this might not be a
reflection of its efficacy in physiological systems and therefore more work is needed
in that respect.

Anti-inflammatory Effect of K. senegalensis

So far, most of the available scientific investigations on the anti-inflammatory
activity of K. senegalensis emanate from Senegal. Freeze dried aqueous extract of K.
senegalensis have been shown to reduce carrageenan induced oedema and was linked
to the presence of methylangolensate and methyl hydroxyangolensate (Thioune et
al., 1999). Furthermore, in a subsequent study, ointments made from a hydro-alcoholic
extract was found to inhibit ear oedema in croton oil induced ear oedema method
which demonstrate the possibility to maintain the anti-inflammatory activity of K.
senegalensis in a gel form (Thioune et al., 2000; 2003). In order to explain the mechanism
Medicinal and Industrial Potentials of Khaya senegalensis | 219

Figure 8.2: Some of the isolated bioactive compounds from different parts of K. senegalensis
(Khalid etal., 1998; Abdulgaleil et al., 2001; Kayser and Abreu, 2001; Nakatani et al., 2001;
Nakatani et al., 2002; Abdulgaleil et al., 2004; El-Aswad et al., 2004; Zhang et al., 2007).

2,6-dihydroxyfissinolide: R1= R2= OH

Fissinolide: R1= R2= H

methyl 3b-acetoxy-6-hydroxy-1-
oxomeliac-14-enoate

Khayanolide D

Khayanolide E
Contd...
220 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

Figure 8.2–Contd...

Khayanolide A
Khayanoside

Khayanolide B: R= OH
Khayanolide C
1-Oacetylkhayanolide B: R= OCOCH3

Seneganolide A: R=1
Khayalactol 2-hydroxyseneganolide A: R=OH
2-acetoxyseneganolide A: R=OAc Contd...
Medicinal and Industrial Potentials of Khaya senegalensis | 221

Figure 8.2–Contd...

3-deacetyl-7-deacetoxy-7-oxokhivorin methyl 6-hydroxyangolensate

3a,7a–dideacetylkhivorin Catechin–(4a,8)-catechin
(Proanthocyanidin B3)

Fisetinidol-(4a 6)-catechin
222 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

of anti-inflammatory activity of K. senegalensis, Lompo et al. (2007a) investigated the

antipyretic, analgesic and antiphospholipase A2 activities of stem bark aqueous extract.
Results from the experiment indicated that the extract significantly inhibited yeast
induced hyperthermia and acetic acid induced writhing response in mice.
Furthermore, the extract inhibited phospholipase A2 activity as well as the release of
arachidonic and oleic acids in P388D1 cells. Thus, the anti-inflammatory activity of
the plant is probably mediated through the inhibition of an important step in the
biosynthesis of prostaglandins.

Antioxidant Activity
Available reports indicate that different parts of K. senegalensis contain significant
antioxidant agents. Preliminary investigation on the in vitro free radical scavenging
activity of K. senegalensis stem bark extracts indicated that the ethanolic extract had
the highest antioxidant activity among other extracts from the plant and also displayed
lower IC50 values than a standard antioxidant agent, rutin (Lompo et al., 2007b). In a
relatively more comprehensive study, Atawodi et al. (2009) investigated the antioxidant
activity of the stem bark, root and leaf samples of K. senegalensis and found that the
stem bark possessed the highest antioxidant activity using 2-deoxyguanosine and
hypoxanthine/xanthine assays. The observed activity was thereafter, linked to the
presence of some phenolics such as catechin, procyanidins, rutin and quercetin
rhamnoside. Even though there are no much reports on the antioxidant activity of the
plant but the preponderance of different kinds of phenolics may provide a lead for
the development of newer herbal recipes with exceptional antioxidant activity.
However, more work would be required especially in a physiological system because
of the limited bioavailability of some phenolics.

Other Biological Activities of K. senegalensis

Under this subheading, we classified all other published reports on the bioactivity
of K. senegalensis extracts that appear in a single publication with no complementary
information elsewhere. For instance, Shaalan et al. (2006) reported that the stem bark
extracts displayed excellent larvicidal actions against the fourth instars of Culex
annulirostris which was statistically similar to the activity observed with azadirachtin.
This finding could be interesting because azadirachtin is a limonoid and several
reports have demonstrated that the most abundant phytochemicals of K. senegalensis
are limonoids.
Khaya senegalensis has also been shown to possess some pesticidal activity.
Bamaiyi et al. (2006) evaluated the effect of K. senegalensis seed oil in the control of
Callosobruchus maculatus on stored cowpea. They observed that the seed oil
significantly reduced the emergence of F1 and F2 progeny of the pest and consequently
reduced the damage made to cowpea by C. maculatus. These area warrant serious
consideration considering the heavy economic loss incurred to cowpea farmers and
traders during storage as a result of this pest. Furthermore, the use of synthetic
chemicals which may be toxic to the final consumers may be limited if more promising
results are obtained over the course of further investigations.
Medicinal and Industrial Potentials of Khaya senegalensis | 223

Investigation on the anticoccidal activity of K. senegalensis stem bark aqueous

extract showed that the extract had no in vitro antisporulation effects (Nwosu et al.,
2011). However, oral treatment of pullet chicks infected with sporulated Eimeria
oocysts with the extract significantly reduced fecal oocyst output and improved packed
cell volume and live weight of the birds. This study demonstrate that the plant contain
some bioactive compounds that could potentially be exploited in the treatment of
avian coccidiosis, a disease that wreak havoc in poultry industry.
A research group from USA and Guinea investigated the effects of K. senegalensis
bark extract on colorectal cancer (Androulakis et al., 2006) by measuring cell growth
inhibition, cyclooxegenase (COX) and prostaglandin E2 suppression as well as
apoptosis by western blot analysis and ELISA. Data obtained from the work
unequivocally revealed that the bark extract possessed anti-proliferative and pro-
apoptotic effects on a range of cell lines which further suggested that the extract has
potent antitumor effects by causing both cell cycle arrest and apoptosis via COX 2-
dependent pathway. These observations support a hypothesis, we earlier made whilst
discussing the anti-inflammatory action of the plant.
Other investigators reported that the simultaneous administration of aqueous
extract of K. senegalensis stem bark with phenylhydrazine was able to protect rats
from the phenyl hydrazine induced anemia (Sanni et al., 2008). However, the same
extract did not show any significant curative effect after the induction of anemia.
Although the stem bark is used in the traditional treatment of anemic conditions and
as blood tonic, but results from the above mentioned work suggest that the extract
simply block or reduce the contact of the anemia agents with red blood cells rather
than a direct effect on the replenishment of red blood cells by the bone marrow.
In order to study the immunomodulatory activity of some Sudanese medicinal
plants, Koko et al. (2008) investigated the inhibitory effects of plants on the whole
blood oxidative burst activity using luminal/lucigenin-based chemiluminescence
assay and K. senegalansis extracts top the list. Further investigation was conducted to
monitor the effects of 14 plants on oxidative burst of isolated polymorphonuclear
and mononuclear cells by using two different phagocytosis activators and also the
plant extracts displayed the best inhibitory actions. It appears therefore that K.
senegalensis extracts contain some immunomodulatory agents but their efficacy needs
to be confirm in an in vivo study. Perhaps some of the previously discussed in vivo
pharmacological activities are simply the result of immunomodulatory action of the
K. senegalensis.
The traditional use of K. senegalensis in diarrhoeal management prompted a
research group to validate the claim. Administration of an aqueous and methanolic
extract of the leaf samples of the plant delayed the onset of diarrhoea and significantly
reduced gastrointestinal motility in rats (Nwosu et al., 2012).
Even though K. senegalensis is commonly used by traditional healers to treat
diabetes mellitus but the only available scientific investigation on the subject was
recently published. Aqueous stem bark extract of K. senegalensis was found to exhibit
a dose dependent reduction in the fasting blood glucose levels of alloxan induced
diabetes model of rats (Kolawole et al., 2012) and the result was comparable to the
224 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

effect of glibenclamide. No much information can be obtained on the actual

antidiabetic effects of this plant because of some limitations and preliminary nature
of the experiment and therefore an all encompassing work that measures most of the
diabetes related parameters especially in a type 2 diabetes model would provide a
more convincing evidence on the subject. Our lab is currently working on this important
area of research.

Toxicological Reports on K. senegalensis

Traditionally, this plant was reported to have the highest adverse effects by the
Tem tribe of Togo and some of the adverse effects reported were diarrhea, polyuria,
hunger, abdominal pains and general weakness (Tchacondo et al., 2011). This
observation clearly points the need for careful scientific assessments in order to identify
the safe dosage and the possible adverse effect of using this plant.
Various toxicological studies have been carried out in vivo on different subjects
to confirm the toxicity of K. senegalensis. Adebayo et al. (2003) are the first to report on
the toxicity aspect of K. senegalensis. Their findings revealed that daily oral
administration of 2 mg/kg bw of ethanolic extract of K. senegalensis bark for 18 days
exerted deleterious effect on the functioning of the kidney by modulating the activity
of the kidney alkaline phosphatase and increasing serum sodium ion concentration.
In another study, daily oral administration of aqueous extract of K. senegalensis bark
for 21 days increased the plasma levels of aspartate and alanine transaminases,
alkaline phosphatase, urea, creatinine, total proteins, sodium and potassium ions
(Kolawole et al., 2011). On the other hand, the extract caused a reduction in the red
blood cells, packed cell volume and heamoglobin level in rats. These observations
connote that the K. senegalensis extract adversely affect the functioning of vital organs
of the body especially liver and kidney.
On the contrary, both single intraperitoneal administration and prolonged daily
oral administration of aqueous extract of the bark of the plant to four-week old pullet
chicks did not produce clinical manifestations of toxicity and/or mortality of the
chicken indicating that the extract is relatively safe by both parenteral and oral routes
(Nwosu et al., 2011). Other investigators evaluated the toxicological effects of aqueous
leaf extract and found that sub chronic administration of the extract for 28 days
resulted in nonsignificant changes in liver and renal functions as well as
histopathology of the organs (Nwosu et al., 2012). Based on these studies, it is possible
to surmise that the stem bark extract of the plant is toxic to mammals, especially after
prolonged exposure, but not to birds. However, the leaves are relatively safer compared
to the bark. Thus, it will be expedient to fully characterize the toxic components of the
bark so that they can be excluded from the list of possible therapeutic candidates to be
exploited from this plant.

Identified Phytochemical Contents of

K. senegalensis Extracts
Using a preliminary reagent-based phytochemical analysis of extracts from the
stem bark, root and leaves of K. senegalensis, Kubramawa et al. (2008) showed that
aqueous and ethanolic extracts from all the parts contained saponins, tannins and
Medicinal and Industrial Potentials of Khaya senegalensis | 225

phenolics but did not contain flavonoids, glycosides and resin. On the contrary, the
presence of glycosides has been reported in the stem bark aqueous extract (Sanni et
al., 2005) whereas flavonoids were detected in the leaf extract (Ndjonka et al., 2011).
Thus the contrasting findings could be related to the geography and/or collection
time of the plant material. On the other hand, quantitative phytochemical analysis of
root sample of the plant showed a high quantity of tannins (7.12 mg/100g), phytate
(4.75 mg/100g) and alkaloids (3.36 mg/100g) (Idu and Igeleke, 2012). Also, the
presence of mineral elements which include calcium, potassium, sodium, magnesium,
iron, copper and zinc has been demonstrated in the stem bark and root samples
(Sanni et al., 2005; Idu and Igeleke, 2012). Even though not much information can be
derived from these preliminary informations but the overall picture of the plant’s
phytochemistry can be snapped.

Isolated Bioactive Agents from

K. senegalensis and their Biological Activity
Extensive literature search reveals that the major bioactive compounds isolated
from different parts and extracts of K. senegalensis are limonoids. The nomenclature
limonoid is derived from the compound limonin, one of the primary bitter components
in citrus fruits. The structural determination of limonin in 1960 marked the beginning
of limonoid (tetranortriterpenoid) chemistry (Arigoni et al., 1960). Today, limonoids
are regarded as group of structurally diverse and highly oxygenated tetracyclic
triterpene derivatives (tetranortriterpenoids), with fascinating structural features and
are commonly found in plants of the families Meliaceae, Rutaceae, Cneoraceae and
Simaroubaceae of the order Rutales. They are derived from a precursor with a 4,4,8-
trimethyl-17- furanylsteroid skeleton derived from euphane (H-20b) or tirucallane
(H-20a) triterpenoids, and, in general, have intensely bitter taste. Approximately
1300 limonoids, exhibiting more than 35 different carbon frameworks created through
ring fission, re-cyclization, reopening, re-closure, and skeletal rearrangements, have
been observed over the past five decades, with new structural types continuing to
appear (Zhang et al., 2009). So far, more than forty five limonoids have been isolated
from different parts of K. senegalensis but in this chapter, we will discuss only those
with established chemical structure and reported biological activity.
The first limonoid isolated from K. senegalensis in 1996 was khayanolide limonoid
which results from a cleavage between C-1, C-2 and a linkage between C-1, C-30 of
phragmalin (Olmo et al., 1996; Zhang et al., 2009). Subsequently, Khalid et al. (1998)
reported the isolation of a novel limonoid, 2,6-dihydroxyfissinolide and two known
limonoids, fissinolide and methyl 3b-acetoxy-6-hydroxy-1-oxomeliac-14-enoate from
the bark of K. senegalensis. Fissinolide was found to be active in vitro against
chloroquine sensitive strain of P. falciparum and Leishmania major whereas 2,6-
dihydroxy fissinolide was slightly active against the two protozoans but methyl 3b-
acetoxy-6-hydroxy-1-oxomeliac-14-enoate had no antiprotozoal activity.
In 2001, another research group identified the presence of two mexicanolide-
type limonoids named khayanone and 2-hydroxyseneganolide as well as one
rearranged phragmalin limonoid 1-O-acetylkhayanolide A (Nakatani et al., 2001).
All the compounds were tested for antifeedant activity against the third-instar larvae
226 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

of Spodoptera littoralis (Boisduval) as well as antiviral activity against virus-induced

cytopathicity in MT-4 cells. Results from the experiment suggest that only 1-O-
acetylkhayanolide A showed appreciable antifeedant activity whereas all the
compounds did not show antiviral activity. Furthermore, this research group isolated
three new modified limonoids from the acetone extract of K. senegalensis bark and
were named khayanolide D, khayanolide E and khayanoside (Nakatani et al., 2002).
Unfortunately, however, only khayanolide E showed good antifeedant activity against
the third-instar larvae of S. littoralis and none of three isolated compound showed
antiviral activity against HIV-1 replication. Eventhough these compounds did not
show remarkable antifeedant and antiviral activity but in our opinion, these findings
could not be used to disregard this compounds from the list of bioactive phytochemicals
from this plant because they may possess exceptional activity in other bioassays.
In other studies by the Nakatani group, the isolation, characterization,
antifeedant and growth inhibitory properties of another three new rearranged
phragmalin-type limonoids named khayanolides A, B and C as well as seneganolide,
methyl angolensate with its 6-hydroxy and 6-acetoxy derivatives, 1-O-
acetylkhayanolide B, and a mexicanolide-type limonoid, khayalactol (Abdelgaleil et
al., 2001; El Aswad et al., 2003). Although all the four compounds displayed remarkable
antifeedant and growth inhibitory activity against S. littoralis larval growth but
khayanolide B was the most potent in the two studies with an EC50 of 2.19 mg/kg and
6.96 mg/kg bw respectively. This study demonstrate the great possibility of developing
new antifeedant and/or larvicidal agent(s) from these K. senegalensis derived
phytochemicals when pursues by pharmaceutical industries.
Although El Aswad et al. (2003) described the isolation of 1-O-acetylkhayanolide
B from the acetone extract but Zhang et al. (2007) reported the isolation and
characterization of this compound from the methanol extract of the stem bark in
addition to another limonoid named 3a,7a-dideacetylkhivorin. Both the two
compounds were subjected to extensive anticancer studies and results obtained
suggested that 3a,7a-dideacetylkhivorin is a potent anticancer and antitumor agent
and the activity was linked to14,15b epoxide moiety of the compound. However, 1-O-
acetylkhayanolide B showed a poor anticancer activity. It seems therefore that 1-O-
acetylkhayanolide B, though abundant and repeatedly isolated from the stem bark,
did not possess much bioactivity based on the existing data but an array of
pharmacological assays need to be conducted on the compound before a definite
statement can be made.
The fruits of K. senegalensis, though not commonly used in traditional medicine,
were also investigated for the presence of limonoids. Three new mexicanolide
limonoids containing a rare conjugated diene lactone system named seneganolide A,
2-hydroxyseneganolide A and 2-acetoxyseneganolide A as well as two known
limonoids, 3- deacetyl-7-deacetoxy-7-oxokhivorin and methyl 6-hydroxyangolensate,
were isolated and characterized from the fruits (Abdelgaleil et al., 2004). Radial growth
technique was then used to evaluate the antifungal activity of seneganolide A,
2-acetoxyseneganolide A and methyl 6-hydroxyangolensate on the fungus
Medicinal and Industrial Potentials of Khaya senegalensis | 227

Botrytis cinerea and 2-acetoxyseneganolide A displayed the best inhibitory activity on

the mycelial growth of the fungus among other phytochemicals. These compounds
are also worth pursuing for other pharmacological properties.
Another research group from China is worth mentioning because of their
extensive studies on limonoids and elucidation of another type of limonoids from
K. senegalensis named khayalenoids (not khayanolides) but in most cases failed to
subject the isolated limonoids to a biological screening. They described the isolation
of khayalenoids A and B with unprecedented 8-oxa-tricyclo[4.3.2.02,7]undecane motif
(Yuan et al., 2009) and seven novel limonoids with different arrangements, named
khayalenoids C – I (Yuan et al., 2010). These khayalenoids need to be subjected to
extensive bioassays in order to understand the likely pharmacological effects they
exert.
Apart from limonoids, another group of phytochemicals isolated from
K. senegalensis are dimeric proanthocyanidins fisetinidol-(4a,6)-catechin
(proanthocyanidin B3) and catechin-(4a,8)-catechin (Kayser and Abreu, 2001). These
compounds were tested against the promastigotes form of L. donovani, L. major,
L. infantum but activity was not detected in the experiment. Interestingly, authors
observed significant activity when the compounds were tested against the amastigote
forms, the stage after invading the Leishmania parasite in the macrophages. These
observations were explained by a subsequent experiment which revealed that there
was an auxiliary stimulation of macrophages mediated defense mechanisms by the
compounds. Also from this study, it is possible to deduce that not only limonoids
and related terpenoid compounds are responsible for the claimed pharmacological
activities of this plant and as such the roles of other bioactive agents need to be
elucidated.
In an attempt to identify the phenolics content in the different parts of
K. senegalensis, Atawodi et al. (2009) used analytical HPLC, GC-MS and LC-MS
analyses to identify phenolics in the leaf extract which include catechin, rutin and
quercetin rhamnoside whilst catechin and procyanidins were identified in the
methanol extract of the stem bark. Procyanidins of unknown identity were detected
in the root extract.

Potential Application of Khaya senegalensis Gum in

Pharmaceutical Formulations
Another important product of K. senegalensis is the gum usually deposited at the
bark. It is a pale greenish yellow to golden yellow gum. The K. senegalensis gum is a
polysaccharide with a galactan in which the 1-3 linked b-D galactopyranosyl residues
are concentrated in the inner chain. It has also been reported to contain both
D-glucoronic and D-galactoronic acids (Olayemi et al., 2011). Furthermore, analysis
of the gum showed that approximately 5 per cent was in the free acid form and the
remainder was largely a calcium salt (Aslam et al., 2006). Also, it is slightly soluble in
water and this is a peculiar characteristic of the meliaceae gum producers. It swells to
about ten times its original weight in water and the swelling of a linear polymer
without dissolution has been said to be an indication that it is crossed linked. Thus,
228 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

the unique properties of the K. senegalensis gum have attracted scientific attention to
establish its suitability in some pharmaceutical formulations and consequently be
exploited by the pharmaceutical industries.
Table 8.1: Some scientifically validated pharmacological activities of K. senegalensis
extracts.
Pharmacological Parts Type of References
Activity Used Extract

Antimalarial Stem bark Ethanolic Ndjonka et al., 2012

Stem bark and leaf Ethanolic Karou et al., 2003
Antihelminthic Stem bark Ethanolic Ademola et al., 2004; 2009
Stem bark Ethanolic Ndjonka et al., 2011
Antitrypanosomal Stem bark Methanolic Atawodi et al., 2003
Stem bark Aqueous and Wurochekke and Nok 2004
methanolic
Stem bark Aqueous Ibrahim et al., 2008
Stem bark Dichloromethane Aderbauer et al., 2008
Stem bark Ethanolic Umar et al., 2010
Antibacterial Stem bark Ethanolic Kone et al., 2004
Stem bark and root Aqueous and Kubmarawa et al., 2008
ethanolic
Root Aqueous and Ide and Igeleke, 2012
ethanolic
Antiinflammatory Stem bark Aqueous Thioune et al., 2000; 2003
Analgesic Stem bark Aqueous Lompo et al., 2007a
Antioxidant Stem bark Ethanolic Lompo et al., 2007b
Stem bark, root Methanol Atawodi et al., 2009
and leaf
Larvicidal Stem bark Methanol, acetone, Shaalan et al., 2006
ethanol and hexane
Pesticidal Seed Oil Bamaiyi et al., 2006
Anticoccidal Stem bark Aqueous Nwosu et al., 2011
Anticancer Stem bark Methanol Androulakis et al., 2006
Antianaemic Stem bark Aqueous Sanni et al., 2008
Immunomodulatory Stem bark Ethanolic Koko et al., 2008
Antidiarrhoea Leaf Aqueous and Nwosu et al., 2012
methanolic
Antidiabetic Stem bark Aqueous Kolawole et al., 2012

Adenuga et al. (2008) evaluated the binding properties of the K. senegalensis gum
in a paracetamol tablet formulation and found that the gum produced tablets with
strong mechanical properties, less tendency to laminate as well as long disintegration
and dissolution times which suggest that it will be an appropriate commercial binding
agent especially when higher mechanical strength and slower release profiles of
Medicinal and Industrial Potentials of Khaya senegalensis | 229

tablets are desired. Other authors investigated the physicochemical properties of the
gum and reported that the gum had a swelling ability that may provide potentials for
its use as a disintegrant in tablet formulation and as a hydro gel in modified release
dosage forms (Mahmud et al., 2008). Furthermore, the rheological flow properties
may also provide potentials for its use as suspending and emulsifying agents owing
to its pseudo plastic and thixotropic flow patterns. In a follow up study, these authors
also investigated the suspending properties of the gum in paracetamol suspensions
(Mahmud et al., 2009). Results from the experiment revealed that the K. senegalensis
gum at 5 per cent w/v concentration produced a flocculated, re-dispersible and
crystal free paracetamol suspension which was stable throughout the storage period
of 8 weeks. The results further demonstrated that K. senegalensis gum has potential to
be used as suspending agent in paracetamol suspensions and may provide substitute
excipients in the liquid formulation of paracetamol and perhaps curb the problem of
paediatric mortality associated with the use of alternative organic chemicals such as
di ethylene glycol.
On the other hand, the swelling ability of the K. senegalensis gum attracted some
investigators to study the release property of the gum in a chloroquine phosphate
tablet formulation (Olayemi et al., 2011). Batches of tablets containing the gum were
observed to be softer, disintegrated faster and had greater dissolution than the batches
of tablets with microcrystalline cellulose. An increase in the concentration of the gum
led to slower disintegration of the tablets. Furthermore, an increase in the concentration
of the gum led to a retardation in the release of the drug and the effective concentration
for fast disintegration and quick drug release was found to be 5 per cent w/w.
Although more studies could be needed in this subject but results from these
experiments have provided clear and unequivocal evidence that the gum of K.
senegalensis could potentially be exploited in pharmaceutical formulations, both tablets
and syrups, so as to reduce over dependence on synthetic agents. These observations
also have far reaching economic consequences to the pharmaceutical industries
(especially in developing countries) and drug end users because huge amount of
resources are currently used in the importation of pharmaceutical excipients which
usually increase the production cost and market prices of the products.

Conclusions
Khaya senegalensis possesses multiple bioactivities that justify its wide usage for
the treatment of an array of tropical diseases in different countries of Africa. The
plant also presents numerous opportunities that could be exploited by developing
countries for health management and economic development. However, the level of
toxicity is a serious concern that warrants further experimental and clinical
investigations before the full utilization of this plant by humans. A number of
compounds present in this plant may be involved in the toxicological effects when
most other compounds may have beneficial effects on health. So the isolation of more
pure compounds from this plant and investigating the individual pharmacological
and toxicological effects can reveal the more benefits and potentials of this plant. A
number of studies on this plant are currently underway from our lab which may
answer many of these unanswered questions.
230 | Medicinal Plants: Phytochemistry, Pharmacology and Therapeutics Vol. 3

Acknowledgements
This study was supported by a competitive research grant from the Research
office, University of KwaZulu-Natal (UKZN), Durban; an incentive grant for rated
researchers and a grant support for women and young researchers from the National
Research Foundation (NRF), Pretoria, South Africa.

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