Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
Open Science
Ethnobotanical, Pharmacological and
Phytochemical Studies
Joseph J. Magadula
Zakaria H. Mbwambo
First published 2014
First Edition
passed away
publishing/printing stage
Contents
Foreword.......................................................................................................... 7
Preamble (About This Book) ........................................................................... 9
Acknowledgements ....................................................................................... 11
General Introduction ...................................................................................... 13
References .................................................................................................... 97
The search for plants that heal still represents a fascinating task. Before the
Synthetic Era, almost all medicines were obtained from plant tissues and organs:
roots, barks, stems, leaves, flowers and fruits. Self-medication was also
observed in non-human primates to control parasitic infections and provide
relief from gastrointestinal upsets. Therefore, in these terms, it seems that
medicinal plant-animal coevolution is more ancient than the medicinal
plant-human one, and that self-medicative behavior of non-human primates
represented the evolutionary force for human traditional herbal medicine. The
history of pharmacognosy is full of famous examples: the antimalarial alkaloid
quinine from Cinchona tree, cardiac glycosides from Digitalis spp., curare from
Chondrodendron tomentosum, the antipsychotic indole alkaloid reserpine from
Rauwolfia serpentina and, among anticancer drugs, taxol from Taxus brevifolia,
vincristine and vinblastine from Catharanthus roseus and camptothecin for
Camptotheca acuminata. Garcinia species enrich this plentiful scenario, by
virtue of their bio- and chemodiversity and healthy properties. In this book, the
authors provide a comprehensive and updated survey on African Garcinia
plants, with emphasis on eastern Africa species, focusing on botanical,
ethnobotanical, ethnopharmacological and phytochemical aspects. The authors
are very expert in the field of Garcinia research, as shown by their relevant
publications on these topics.
Editor-in-Chief
This book has been written as a way of documenting the research results done
by the authors and other researchers over years on the African Garcinia plants.
Generally, the book is based on the area of academic training of the authors,
which is the organic chemistry and in particular, the Chemistry of Natural
Products.
This book has been arranged in four chapters. The first chapter gives an
overview of the Garcinia plant species growing in Tanzania, a country of
domicile of the authors of this book. Furthermore, the localities in Tanzania
where the plants are collected are included together with the basic features of
some Garcinia plants growing in Tanzania.
Chapter four deals with the phytochemistry of African Garcinia plants, from
which over 100 natural product compounds have been isolated. The major
10 Preamble (About This Book)
It is our trust that, this book will provide potential and useful reference
materials for the natural products researchers. It will also offer useful academic
and technical information to ethnobotanists, ethnopharmacologists,
pharmacologists, phytochemists and foresters in Africa and all over the global.
&
[Dip Ed, BSc Ed (Hons), MSc (chem.), PhD] [MSc Pharm, PhD]
A special thanks to our families for tolerating our absence when performing
our research and academic duties and particularly during the time of producing
this book.
12 Acknowledgements
KINGDOM Plantae
DIVISION Magnoliophyta
CLASS Eudicotyledoneae
ORDER Malpighiales
FAMILY Clusiaceae
TRIBE Garcinieae
GENUS Garcinia
SPECIES (Ca 600 species worldwide)
species are reported to grow, with 20 of them been reported from Cameroon
(Agyili et al., 2007) and the rest distributed in other West African countries. In
South Africa, only two (2) Garcinia species namely G. gerrardii and G.
livingstoneii (African mangosteen) are reported to be indigenous and they are
famous in traditional medicine (Palgrave et al., 2002). The distribution of
Garcinia plant species in Africa indicated the plants to grow and being reported
phytochemicaly and pharmacologicaly from only 20 African countries mainly
in the south of Sahara region (Fig. 1).
KEY:
No any report
phytochemical reports included in this book indicate that only a small fraction
of African Garcinia plants have been studied for their chemical constituents.
This necessitates further work to be done on an uninvestigated species.
1.1 Introduction
Tanzania, like many other African countries, is endowed with tropical forests
that are rich in natural resources, particularly plants. The country is divided into
six major ecological zones, namely Lake Victoria Mosaic, Coastal Forest and
Thickets, Afromontane Forest, Acacia-Savanna and Grasslands, Acacia -
Commiphora Thornbush and Miombo forests/woodlands, while the floristic
regions are known to be eight, T1-T8. Every zone/region has its characteristic
flora/plants and some uniqueness in terms of medicinal value of plants (Stuart et
al., 1990). Our ethnobotanical survey and the literature report revealed that
Garcinia plants grows at least in almost all ecological and floristic zones except
T2, where there is no any Garcinia plant species being reported (Bampss et al.,
1978).
Tanzanian flora is within the Tropical East African Flora which comprises of
about 21,650 vascular plant species. Tanzania alone has over 10,650 higher plant
species, out of which about 2,500 species are indigenous whereas more than 1200
plant species are endemic. Currently, Tanzania has eight (8) floristic ecozones,
T1-8 (Fig. 2), each zone being characterised by unique features of plant diversity,
including the richest Eastern Arc Mountains as one of the biodiversity hot spots of
Tanzania. It spreads and covers all parts of T3 and T6 floristic regions and is
reported to contain about 2000 plant species with 25 30% being endemic to the
forests and forest edges of the mountains (Burgess et al., 2002).
Tanzanian Garcinia Species 19
Zone Regions
T1 Geita, Mwanza, Kagera, Mara, Simiyu and Shinyanga
T2 Arusha, Manyara
T3 Kilimanjaro, Tanga
T4 Kigoma, Rukwa, Tabora
T5 Dodoma, Singida
T6 Coastal, Dar es Salaam, Morogoro
T7 Iringa, Mbeya
T8 Lindi, Mtwara, Ruvuma
P Pemba
Z Zanzibar
20 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Plants from the genus Garcinia are usually evergreen trees or shrubs and
dioecious and most of them grow in lowland rainforests or along riverines (Peres
and Nagem, 1997). Most notably, they are trees or shrubs, secreting yellow latex
when cut (Fig. 3) and generally glabrous. Leaves opposite or whorled, with latex
canals; petiole bases usually strongly excavated. Inflorescences in axillary
fascicles, rarely branched, or flowers solitary, axillary or terminal. Flowers
bisexual and/or unisexual (plants usually dioecious or polygamous). Sepals 2-4(5),
mostly imbricate; petals 2-4(-6), white, yellow, or red, decussate or imbricate, the
pairs often of different sizes. Stamens free, variously fasciculate, or connate into a
central mass, numerous in staminate flowers, fewer in bisexual flowers; anthers
short. Ovary 2-12-locular, often absent from staminate flowers; ovule 1 per locule;
styles short or lacking; stigmas expanded. Fruit a berry, mostly 1-locular, smooth
to verrucose, leathery, ellipsoid to globose or ovoid, the mesocarp often juicy and
sweet. Seeds 1-4; cotyledons minute.
(http://www.mobot.org/MOBOT/research/ven-guayana/clusiaceae/page6.shtml)
a b
Fig. 3. (a) Stem bark of G. semseii showing yellow exudates and
(b) G. semseii showing some leaves.
24 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Fruits have been observed to have one to four seeds with fleshy, smooth or
verrucose glabrous or puberulous berry (Bamps et al, 1978). Fruits of many
Garcinia species are edible, particularly those of an African mangosteen (Figure
4) and are highly eaten by wild animals as well as by humans.
This plant is mostly found among dry coastal forest species reported to grow
in Mozambique and Tanzania and it is threatened by habitat loss. (Lovett and
Clarke, 1998). In Mozambique, it grows between Muaguide and the
Quissanga-Macomia crossroads, 23 km from Muaguide. In Tanzania, it is
reported to grow in Pugu Forest Reserve, Coastal region at Kazimzumbwi area
as well as at Litipo forest in Lindi region.
It is a small evergreen tree with leaves being oblong or elliptic. The leaves
and bark exude yellow sticky latex when cut. Lateral veins are evidently fixed
on both surfaces. Flowers are greenish-yellow and observed in solitary or in
small clusters. The fruits are edible as they are fleshy, spherical and yellow
when ripe.
This is a small tree, 5-6 m tall, with a straight and dark brown trunk,
producing yellow latex when cut. Leaves are opposite, stiff, 7-12 cm long and
3-5 cm wide. Flowers are whitish and small, produced in axillary groups of 1-15
at branch nodes (Fig. 8). Fruits are round, about 3 cm in diameter, with a thin
orange to reddish peel with an aromatic sweet sour taste. Seeds are in 1 or 2. It
is commonly known as the lemon drop mangosteen. The plant is propagated
by seeds that germinate easily with flowering and fruiting takes about 3 years.
Fig. 8. Aerial parts and flowers of G. edulis at Amani Nature Reserve, Muheza,
Tanzania.
Fig. 9. Aerial parts and fruits of G. ferrea at Amani Nature Reserve, Muheza,
Tanzania.
The reported common names for this plant are Granite garcinia (English),
Granite mangosteen (English) and Mutunduru (Shona) (Drummond, 1981). It is
a small evergreen tree growing up to 4-5 m high. The leaves are oblong or
elliptic, thick and leathery, exuding yellow sticky latex when broken. The veins
are lateral and conspicuously etched on both surfaces. Flowers are solitary or in
small clusters, axillary, greenish-yellow and short-lived with the flowering time
Tanzanian Garcinia Species 29
being September to November. Fruits are always fleshy, spherical, yellow when
ripe and are edible.
The habitat of this plant is on granite kopjes, rocky outcrops and in riverine
fringes with an altitude of about 900-1800 m. Its distribution ranges from Sudan
southwards through eastern Africa to Angola, Mozambique and Zimbabwe
(Smith & Allen, 2004). In Tanzania, G. huillensis is reported to grow from
Lugoda (Iringa), Geita (24 km South of Geita Gold Mines) and Gombe Forest
Reserve along Kakombe valley in Kigoma region.
The habitat of G. indica is always forest lands, riversides and wastelands. The
plant prefers evergreen forests, but sometimes they also thrive in areas with
relatively low rainfall. In Tanzania, it is repoted to grow in Zanzibar at
Migombani and Mtoni areas.
This plant is always found in the understorey of evergreen forest and forested
ravines at an altitude range of 1350-2100 m. It is a small to medium-sized tree
with main branches, it appears horizontal while the lateral branches are grooved
and angular. When cut it gives yellow sap. Leaves are opposite, narrowly
elliptic to oblong and they are dull bluish to grey-green. Flowers are in clusters
on short spur-branchlets along the stems. Fruits are spherical and yellow to
orange and they are edible. The flowering time is between September and
October.
Tanzanian Garcinia Species 31
It grows in a wide range of tropical Africa from from Cte d'Ivoire east to
Somalia, and south to South Africa being commonly known as African
mangosteen to its esteemed fruits. The distribution of the plant in Tanzania is
high as it is reported to grow in Chalinze area, Pugu Forest Reserve and
kisarawe at Kazimzumbwi village and it is called Mutumbi or Mpekechu (in
Swahili).
It is a small tree of 7-8 m high with dense heavy branched crown. The leaves
are leathery. The petioles are short and thick. The flowers are 5 centimeters in
diameter, 4-parted, bisexual, and borne singly or in pairs at the ends of the
branchlets. The seeds are large, flattened- and embedded in snowy-white or
pinkish delicious pulp. The mangosteen fruit is the size of a small apple, purple
colored, with a hard rind. Inside there are typically five to seven seeds
surrounded by a sweet, juicy cover (or aril). Dried fruits are well known for
their medicinal uses.
Tanzanian Garcinia Species 33
Fig. 14. Aerial parts and fruits of G. mangostana at Amani Nature Reserve, Tanzania.
This appears as a shrub or small tree of about 5 metres high having thick
branches with a grayish or corky bark. The bark secrets yellow and sticky latex
when cut. Leaves are observed to be in whorls of three. Flowers are observed to
be unisexual and clustered in axils or above the leaf-scars on mostly leafleded
branches.
woodland rather than riverine forest. In Tanzania, this plant is reported to grow
in Sumbawanga (Rukwa) at Kasanga area-Ngolotwa.
This is a tree that grows to the height of about 15 mters, having slightly
wrinkled branchlets and rough nodes. The leaves are opposite and they become
reddish brown when dry. The plant always contains two flowers at the leafless
nodes. Fruits are roughly warted and highly eated by monkeys.
Fig. 15. Leaves and Fruits of G. semseii taken at Kimboza Forest Reserve, Morogoro
district.
It is a small tree that grows to about 20 m high and haaving a bole of over 1
m in girth. It has a dark orangeish scaly bark exuding some yellow latex when
cut. Leaves are simple and opposite while petioles are short or normal and entire
margin. Flowers are dioecious and in fascicles of 530 in the axils of leaves.
Fruits are purplish-green turning to yellow with 1-25 cm in diameter.
The plant always grows in riverines and uplands to about 1500 m elevation.
The distribution ranges from Angola, Congo, Gabon, Cameroon, Central
African Republic and DR Congo. In Tanzania, it is reported from 48 km South
of Kibondo at Mukugwe River, Rungwe at Mwalesi River, Njombe (upper
Ruhudje river and Lupembe area-north of the river).
This is a highly branched plant growing to about 20 m high. Its bark is grey
or brown and gives white/yellow exudates when cut. Leaves are simple,
opposite or whorled while petioles are angled and/or narrowly winged. Flowers
36 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Fig. 17. Aerial parts of G. volkensii at Shagayu Forest Reserve, Lushoto, Tanzania.
and has a pleasant acid taste. It usally contains two seeds, sometimes is called
yellow mangosteen or camboge. Flowering occurs between March and May.
Fig. 18. Aerial parts and fruits of G. xanthochymus at Amani Nature Reserve, Tanzania.
The tree is well adapted to shade and humid conditions. In Tanzania, the
plant was cultivated at Amani Nature Reserve, near Sigi river, Muheza district,
Tanga region.
Ethnobotany of African
Garcinia Plants
40 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
2.1 Introduction
Medicinal plants play an important role in the healthcare systems all over the
world.
Around 80% of general population in the world uses plants to treat several
illnesses (UICN, OMS, WWF, 1993). Ethnobotanical studies are very important
to reveal the past and present culture about plants. Human societies throughout
the world have accumulated a vast body of indigenous knowledge over
centuries on medicinal uses of plants, and for other related uses including
poison for fish and hunting, purifying water, and for controlling pests and
diseases of crops and livestock.
In this respect, people are able to use and conceptualize plants in their local
environments. For instance, medicinemen or herbalists have a good knowledge
on botanical description including correct identification of plants for intended
purposes. Hence, ethnobotany details the knowledge of plants by the local
people and their usefulness as understood by the people of a particular ethnic
group (Tor-Anyiin et al., 2003), particularly this study involves the scientific
study of the traditional knowledge and customs of a people concerning plants
and their medical, religious, and other uses.
cancer, liver cirrhosis and cough (Table 3). Many literatures indicated Garcinia
kola, a plant reported to grow in many Western African countries, to be the
most studied Garcinia species in all aspects, including ethnomedical use,
pharmacology and its phytochemistry. Sometimes, it is referred to as a wonder
plant because every part of it has been found to be of medicinal importance
(Dalziel, 1937). Ethnomedically, many Garcinia plants are used as a decoction,
an infusion or as a juice. Most extracts are prepared with cold or hot water and
are applied for the treatment of toothache, inflammations, for wound-healing,
jaundice, ulcers, dysentery, as aphrodisiac, for fever, sleeping sickness, venereal
diseases, liver cirrhosis, arthritis and respiratory track diseases. Other Garcinia
plants are used as chewing sticks, fertilization stimulant, aid childbirth while
some fresh or dried fruits are used as food. For instance, G. livingstoneii is
commonly known as an African mangosteen as it produces very tasty and
delicious fruits while the powdered root is used as an aphrodisiac (Anorld &
Gulumian, 1984). Hence, many Garcinia plants are known for different
traditional uses (Table 3) while others are not reported for any ethnomedical
use.
42 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Scientific Where
S/N Part used Traditional uses Reference
name collected
Used as a
masticatory, antidote
Dried seed Iwu et al. (1990)
and inflammatory
disorders
Treat cough,
abdominal colic, Akintonwa and Essien
aphrodisiac and (1990)
catarrh
Treat diarrhoea,
hepatitis,
dysmenorrheal, Braide (1989)
gastroenteritis and
asthma
Treat bronchitis, Adesina et al. (1995);
diarrhoea, and throat Orie and Ekon (1993),
infections Iwu 1993.
6 G. livingstoneii Tanzania Fruit Used as food Johns et al. (1984)
Used for toothache,
Anorld and Gulumian
Venda (RSA) Leaf impotency and
(1984)
aphrodisiac
Used to aid
Kenya Root Yu et al. (1982)
Childbirth
Samuelsson et al.
Somalia Root Treat abdomen pains
(1992)
Used as an
South Africa Root Palgrave et al. (2002)
aphrodisiac
To treat gastric
infections, antidote
G. lucida Taanzania Stem against poison, Fotie at al. (2007)
aphrodisiac
properties
Treat stomach ulcers
7 G. mangostana. Madagascar Leaf Novy (1997)
and liver diseases
Used for dressing
8 G. polyantha Cameroon Sap (latex) Bouquet (1969)
wounds
Akendengue and
9 G. punctata Gabon Stem bark Treat headache
Louis (1994)
G. Antidote, chew-stick
10 Cameroon Stem bark Bouquet, 1969
smeathmannii and laxative
Ophtalmia (eye
Sap (latex) Bouquet, 1969
treatments)
Bark latex Skin, mucosae Bouquet, 1969
Pharmacological Activities
of African Garcinia
Plants
46 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
3.1 Introduction
Plants remain rich and potential source of therapeutic compounds for the
development of new drugs. Secondary metabolites obtained from plants have
been a great source of many drugs for managing various diseases. Even if recent
advances in biochemical engineering and other biotechnologies represent
alternative sources of drugs, more than 70 % of the current therapeutic drugs
derive their structures from plants used in traditional medicine
(Chantarasriwong, 2010). Although many and new drugs including antibiotics
have been developed in the last three decades, resistance to them by infectious
microorganisms has increased. As a result, the search for new bioactive
compounds from plants for pharmaceutical purposes has gradually increased
worldwide (Kaikabo et al., 2009). Many recent biological studies on medicinal
plants used as folklore remedies in the treatment of different ailments have
attracted the attention of a number of researchers as possible alternatives to the
existing incurable diseases and the problem of drug resistances. Globally, the
problems of multiple resistance as well as emergence of new and resurrection of
previously eradicated diseases have necessitated the continued effort to search
for novel and effective drugs from medicinal plants to complement the existing
synthetic drugs.
Recent studies have indicated that Garcinia species possess a wide range of
biological activities and led to a greater understanding of the pharmacology of
various species, particularly in relation to the antimicrobial, anticancer, antiviral,
antioxidant, antimalarial and other biological activities. These pharmacological
studies supports to the traditional uses of Garcinia plants in treating different
ailments by many African societies. Hence, reported pharmacological activities
on crude extracts and compounds from African Garcinia plants indicated
Chapter 3 Pharmacological Activities of African Garcinia Plants 47
The treatment of infectious diseases has existed for many years and, as a
result, many reports of antimicrobial extracts and compounds from Garcinia
species have been documented from various parts of Africa. Over 20 different
crude extracts from more than 10 Garcinia plant species found in African flora
have been investigated for antimicrobial properties (Table 4).
One of the reports is on the ethanol extract of the dried stem bark of G. afzelii
collected in Togo. This extract showed significant antibacterial and antifungal
activities against Staphylococcus aureus and Asperigillus fumigatus (Kpakote et
al., 1998). In another study from a Congolese plant, G. huillensis, the in vitro
testing of the water extract of the stem bark indicated marked activity against
Cytospora species (Laine et al., 1985), while the antibacterial activity was noted
in the petroleum ether extract of this plant against Staphylococcus aureus with
the minimum inhibition (MIC) of 62.5 g/ml (Bakana et al., 1987).
OH
OH
HO O
HO O
OH
OR OH O
OH O
HO O
HO O R
1 H OH
OH O
OH O 2 CH3 3
OH OH
OH O OH O OH OH
O O O
OH OH
OH O OH O OH O
4 5 6
OH OH
OH
OH
O
O O
O OH
O OH
O OH
O OH
7 8 9
OH O OH
OH O OH
O OH
OH O O
OH
10 11 12
Fig. 20. Structures of bioactive compounds isolated from some African Garcinia plants.
52 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Malaria is one of the most serious protozoal diseases in man and ranks
number one in terms of morbidity in the tropical countries. It is estimated that at
least 40% of the world's population live in endemic areas, among which 90%
are distributed in Africa south of Sahara desert (Bruce-Chwatt et al., 1981). The
use of plant secondary metabolites as a cure and/or leads for the development of
Chapter 3 Pharmacological Activities of African Garcinia Plants 61
Garcinia kola, a tropical plant which grows in moist forest, has found to have
many applications in traditional medicine, especially in the West and Central
African sub-region. This plant is the highly investigated among all Garcinia
species growing in Africa. Farombi and co-workers investigated the antioxidant
and scavenging properties of a flavonoid extract of G. kola seeds. The in vitro
assay involved the free radicals and reactive oxygen species from which the
flavonoid extract, commonly known as kolaviron, exhibited noticeably reducing
power and antioxidant activity by inhibiting the peroxidation of linoleic acid. It
further exhibited 57% scavenging effect on superoxide at a concentration of 1
mg/ml and 85% scavenging activity on hydrogen peroxide at a concentration of
1.5 g/ml. Similarly, flavonoid extract, at a concentration of 2 mg/ml, showed a
89% scavenging effect on a,a-diphenylb-picrylhydrazyl radical (DPPH),
Chapter 3 Pharmacological Activities of African Garcinia Plants 65
indicating that the extract has effective activities as a hydrogen donor and as a
primary antioxidant to react with lipid radicals (Farombi et al., 2002). The
protective effects of kolaviron, a Garcinia biflavonoid extract from the seeds of
G. kola widely consumed in some West African countries, was tested against
oxidative damage to molecular targets ex-vivo and in vitro. Treatment with
hydrogen peroxide (H2O2) at a concentration of 100 g/ml increased the levels
of DNA strand breaks and oxidized purine and pyrimidine bases in both human
lymphocytes and rat liver cells using alkaline single cell gel electrophoresis
(COMET assay). Kolaviron was protective at concentrations between 30-90
g/ml and decreased H2O2-induced DNA strand breaks and oxidized bases
(Farombi et al., 2004). Furthermore, kolaviron exhibited protective effects
against oxidative damage to molecular targets via scavenging of free radicals
and iron binding (Farombi et al., 2004).
OH
HO O
OH
HO O O
OH
OH O
HO O
O O
OH O
13
14
OH OH
R
O
OH O OH
OH OH
O O
O
OH O
R O OH
15 beta-H O OH
O OH
16 alpha-H 17 18
O O OCH3 OH O OCH3
i-Pr CHO
O
HO 15
OH HO O
O OH
O 21
20
19
O OCH3 CH3
H3CO HO
O H3C O
OH
OH CH3
23
22
CH3
OH O R
HO O
HO
R
OH 25 CHO
OH O CH3
26 COOH
HO O O
OH
OH HO
OH O
27
24
Fig. 20. Structures of bioactive compounds isolated from some African Garcinia plants
(Cont).
68 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Consequently, this has raised the interest of screening crude plant extracts for
anti-HIV activity, while little research has been done on pure compounds.
Two Garcinia plants growing in Tanzania has been evaluated for their in
vitro anti-HIV activity against HIV-1 viral replication in MT4 cells. The ethanol
extracts of the fruits of G. livingstonei and G. semseii revealed significant
anti-HIV-1 activity with EC50 values of 2.25 0.51 and 0.93 0.67 g/mL
respectively (Magadula & Suleiman, 2010). Furthermore, another study from
ethanol extracts of some Garcinia species collected in Tanzania were
investigated for their HIV-1 protease (HIV-1 PR) inhibitory activities using
high performance liquid chromatography (HPLC). Among the tested extracts,
the fruit hulls of G. semseii showed the most potent inhibitory activity against
HIV-1 PR with an IC50 value of 5.7 g/ml, followed by the stem bark extracts of
G. edulis and G. kingaensis with IC50 values of 9.2 and 15.2 g/ml, respectively
(Magadula & Tewtrakul, 2010). In another study, the chloroform-methanol (1:1)
extract of the dried leaf of G. ovalifolia, collected from Central African
Republic, showed significant anti-HIV activity when tested in vitro (Gustafson
et al., 1992).
OH O OH
OH O OH O OH
O O
O O
OH
OH OH
28 29 30
OH
OH OH
HO O HO O
O OCH3 R1
H3CO OH
R2 OH
OH
OH O OH O
O OH R1 R2
HO O
33 OH glucose
31 34 H glucose
R
OH O
R
32 OH
35 H
O OH
OH
HO HO O
HO O OCH3
OH
O O
36 37
Fig. 20. Structures of bioactive compounds isolated from some African Garcinia plants
(Cont).
IC50 value of 93.0, 2.54 and 74.4 g/ml, respectively, while compound 39
showed significant inhibition against both AChE (IC50 = 46.3 g/ml) and BChE
(IC50 = 25.5 g/ml) compared to the standard, galantamine (IC50 = 0.5 and 8.5
g/ml, respectively). Compound 38 indicated 41.8% and 7.0% inhibition
against AChE and BChE, respectively, at the concentration of 0.2 mg/ml (Louh
et al., 2008).
flavonoids, steroids, alkaloids, tannins and phenols. The results revealed that the
anti-motility effects of the aqueous extract of G. buchananii are significantlly
mediated by compounds that affect 5-HT(3) and 5-HT(4) receptors. However,
no single compound was characterized or identified from the active components
(Boakye et al., 2012). Furthermore, the G. buchananii extract and its
anti-motility fractions were studied to be effective remedies against
lactose-induced diarrhea. Results indicated that the active extract contained
compounds that are responsible for reducing the body weight and supporting the
upward intake of food and water (Boakye et al., 2012).
The crude extract of the stem bark of the G. lucida indicated a significant
trypanocidal and antileishmanial activities. The bioassay guided isolation of the
constituents of the stem bark led to the isolation of three
benzo[c]phenanthridine alkaloids, dihydrochelerythrine (48), 6-
acetonyldihydrochelerythrine (49) and lucidamine A (50). The isolated
compounds as well as the crude extract displayed poweful antiprotozoal activity
against Trypanosoma brucei brucei and Leishmania donovani, with little
toxicity to Vero cells and the host cells (Fotie et al., 2007). The crude extract of
G. lucida displayed significant activity against T. b. brucei (IC50 4.9 g/mL)
with no toxicity on the Vero cell. The isolated compounds, the
dihydrochelerythrine derivatives (48-50) exhibited interesting activity, with IC50
Chapter 3 Pharmacological Activities of African Garcinia Plants 73
values in the range 0.814.1 M. Dihydrochelerythrine (48) was the most potent
compound (IC50 0.8 M), with more than 44-fold selectivity for T. b. brucei
parasites over Vero cells (Fotie et al., 2007). When tested on promastigote L.
donovani, the crude extract (100 g/mL) and compounds 48-50 (100 M) were
able to clear the parasites (100% inhibition), whereas at 10 M, these
compounds achieved about 89, 87, and 76% inhibition, respectively.
Phytochemistry of
African Garcinia
Plants
76 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
4.1 Introduction
Many African countries are endowed with tropical forests that are rich in the
diversity of plants. These plants constitute a rich, but largely untapped pool of
natural products as chemicals with potential socio-economic benefits. Given
that the occurrence of many secondary metabolites is genus or species specific,
probability is high that many plants contains potentially useful biological
properties that will remain undiscovered, unidentified and unused; this is a true
case for tropical African rain forests. Presently, many medicinal plants,
including Garcinia plants, are threatened with extinction or severe genetic loss,
while their detailed scientific information is still lacking. Hence, a continued
and sustainable biological and chemical investigation of these useful plants is
needed.
From the Garcina plants growing in Africa, more than 130 secondary
metabolites have been isolated, with benzophenones, flavonoids, triterpenoids
and xanthones being the major constituents (Table 5). Furthermore, about 18
other compounds have been reported from African Garcinia species. From all
the African Garcinia plants, the most well-known and phytochemically studied
is G. kola which is reported to grow in almost all West and Central African
countries (Iwu et al., 1990, Madubunyi, 1995, Okunji & Iwu, 1991, Kapadia et
al., 1994). However, these phytochemical reports still indicate that only a small
fraction of African Garcinia plants have been studied for their chemical
constituents. This necessitates further work to be done for an uninvestigated
species.
Chapter 4 Phytochemistry of African Garcinia Plants 77
Bakana et al.
Garcinol (51) G. huillensis Stem bark Cameroon
(1987)
Waterman and
Xanthochymol (52) G. staudtii Stem bark Nigeria
Hussain (1982)
Stem, leaves Hussain and
G. mannii Cameroon
& seeds Waterman (1982)
Ampofo et al.
G. polyantha Stem bark Cameroon
(1986)
Magadula et al.
Semsinone A (53) G. semseii Stem bark Tanzania
(2008)
Magadula et al.
Semsinone B (54) G. semseii Stem bark Tanzania
(2008)
Magadula et al.
Semsinone C (55) G. semseii Stem bark Tanzania
(2008)
Benzophen Guttiferone K (56) G. semseii Fruit hulls Tanzania Magadula (2012)
ones Guttiferone A (36) G. semseii Fruit hulls Tanzania Magadula (2012)
G. Gustafson et al.
Fruit Tanzania
livingstoneii (1992)
Gustafson et al.
Guttiferone E (57) G. ovalifolia Leaf CAR
(1992)
Gustafson et al.
Isoxanthochymol (13) G. ovalifolia Leaf CAR
(1992)
Ampofo et al.
G. polyantha Stem bark Cameroon
(1986)
Lannang et al.
G. polyantha Root bark Cameroon
(2008)
Hussain et al.
Kolanone (58) G. kola Fruit pulp Nigeria
(1982)
G. kola Dried root Nigeria Iwu et al. (1990)
Madubunyi
G. kola Dried seed Nigeria
(1995)
Jackson et al.
Biflavanone GB-1 (3) G. buchananii Heartwood Uganda
(1971)
Leaf, Seed,
Hussain and
G. mannii Stem bark, Cameroon
Waterman (1982)
heartwood
Flavonoids
G. kola Dried seed Nigeria Iwu (1985)
DR Kabangu et al.
G. kola Stem bark,
Congo (1987)
G. kola Root bark Nigeria Han et al. (2005)
Jackson et al.
Biflavanone GB-2 (24) G. buchananii Heartwood Uganda
(1971)
78 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Where
Class Name Plant species Part Reference
collected
Leaf, Seed,
Hussain and
G. mannii Stem bark, Cameroon
Waterman (1982)
heartwood
G. kola Dried seed Nigeria Iwu (1985)
DR Kabangu et al.
G. kola Stem bark,
Congo (1987)
Terashima et al.
G. kola Dried stem Nigeria
(1999a)
Biflavanone GB-1A Jackson et al.
G. buchananii Heartwood Uganda
(59) (1971)
Leaf, Seed,
Hussain and
G. mannii Stem bark, Cameroon
Waterman (1982)
heartwood
Herbin et al.
G. volkensii Heartwood Kenya
(1970)
Terashima et al.
G. kola Dried stem Nigeria
(1999a)
Biflavanone GB-1B Terashima et al.
G. kola Dried stem Nigeria
(60) (1999a)
Biflavanone GB-2A Jackson et al.
G. buchananii Heartwood Uganda
(61) (1971)
Leaf, Seed,
Hussain and
G. mannii Stem bark, Cameroon
Waterman (1982)
heartwood
Herbin et al.
G. volkensii Heartwood Kenya
(1970)
Terashima et al.
G. kola Dried stem Nigeria
(1999a)
G. Gartlan et al.
Cyanidin (62) Stem & seed Cameroon
chromocarpa (1980)
Stem, seed & Hussain and
Eriodictyol (63) G. conrauana Cameroon
leaf Waterman (1982)
Hussain and
Fukugetin (64) G. conrauana Heartwood Cameroon
Waterman (1982)
O-Methylfukugetin Stem, Hussain and
G. conrauana Cameroon
(65) heartwood Waterman (1982)
Waterman and
G. quadrifaria Stem bark Cameroon
Hussain (1982)
Waterman and
G. densivenia Stem bark Cameroon
Crichton (1980)
Seed, Leaf,
Hussain and
Manniflavanone (32) G. mannii Stem bark, Cameroon
Waterman (1982)
heartwood
G. kola Dried root Nigeria Iwu et al. (1990)
Hussain and
G. conrauana Leaves Cameroon
Waterman (1982)
Morelloflavone G. mannii Heartwood Cameroon Hussain and
Chapter 4 Phytochemistry of African Garcinia Plants 79
Where
Class Name Plant species Part Reference
collected
glycoside (66) Waterman (1982)
Taxifolin-6-C--D-gluc Mbafor et al.
G. epunctata Stem bark Cameroon
opyranoside (33) (1989)
G. buchananii Stem bark Tanzania Stark et al. (2012)
Aromadendrin-6-C--D
G. buchananii Stem bark Tanzania Stark et al. (2012)
-glucopyranoside (34)
Buchananiflavanone
G. buchananii Stem bark Tanzania Stark et al. (2012)
(35)
G. Mbwambo et al.
Volkensiflavone (67) Root bark Tanzania
livingstoneii (2006)
Mbwambo et al.
G. volkensii Stem bark Tanzania
(2011)
G. Mbwambo et al.
Morelloflavone (68) Root bark Tanzania
livingstoneii (2006)
Waterman and
G. quadrifaria Stem bark Cameroon
Hussain (1982)
Waterman and
G. densivenia Stem bark Cameroon
Crichton (1980)
Herbin et al.
G. volkensii Heartwood Kenya
(1970)
Mbwambo et al.
G. volkensii Stem bark Tanzania
(2011)
ent-Naringeninyl-(I-3,
Waterman and
II-8)-4'-O-methylnaring G. quadrifaria Stem bark Cameroon
Hussain (1982)
enin (14)
G. Mbwambo et al.
Root bark Tanzania
livingstoneii (2006)
Kolaflavanone (43) G. kola Root bark Nigeria Iwu et al. (1990)
G. kola Dried Seed Nigeria Iwu (1985)
Kapadia et al.
G. kola Dried Seed Nigeria
(1994)
Garcinia biflavanone Okunji & Iwu
G. kola Dried seed Nigeria
GB-1 (3) (1991)
Iwu and Igboko
G. kola Dried seed Nigeria
(1982)
G. kola Dried seed Nigeria Iwu et al. (1987)
Madubunyi
G. kola Dried seed Nigeria
(1995)
Garcinia biflavanone Okunji and Iwu
G. kola Dried seed Nigeria
GB-2 (24) (1991)
G. kola Dried seed Nigeria Iwu et al. (1987)
Madubunyi
G. kola Dried seed Nigeria
(1995)
Terashima et al.
Amentoflavone (1) G. kola Dried stem Nigeria
(1999a)
G. Leaf South Kaikabo et al.
80 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Where
Class Name Plant species Part Reference
collected
livingstoneii Africa (2009)
4''-Methoxyamentoflav G. South Kaikabo et al.
Leaf
one (2) livingstoneii Africa (2009)
Iwu and Igboko
Acacetin (69) G. kola Seed Nigeria
(1982)
Terashima et al.
Garcinianin (70) G. kola Dried stem Nigeria
(1995)
Terashima et al.
G. kola Dried seed Nigeria
(1997)
Kolabiflavonoid GB-1 Kapadia et al.
G. kola Dried seed Nigeria
(3) (1994)
Kolabiflavonoid GB-2 Kapadia et al.
G. kola Dried seed Nigeria
(24) (1994)
Parveen et al.
Apigenin (71) G. nervosa Dried leaf Nigeria
(2004)
Parveen et al.
3,8''-Biapigenin (72) G. nervosa Dried leaf Nigeria
(2004)
Nervosin (73) G. nervosa Dried leaf Nigeria Ilyas et al. (1994)
Irigenin (74) G. nervosa Dried leaf Nigeria Ilyas et al. (1994)
7-Methyltectorigenin
G. nervosa Dried leaf Nigeria Ilyas et al. (1994)
(75)
I-5, II-5
I-7,II-7,I-3,I-4,
II-4-Heptahydroxy-[I-
G. nervosa Dried leaf Nigeria Babu et al. (1988)
3,
II-8]-flavanonylflavone
flavanoylflavone (76)
I-3, II-3, I-5, II-5, I-7,
II-7,
Parveen et al.
I-4',II-4'-Octahydroxy G. nervosa Dried leaf Nigeria
(2004)
[I-2', II-2'] biflavone
(77)
Parveen et al.
Quercetin (78) G. nervosa Dried leaf Nigeria
(2004)
Taxifolin (79) G. buchananii Stem bark Tanzania Stark et al. (2012)
Waterman et al.
Friedelin (80) G. ovalifolia Stem bark Cameroon
(1980)
Lannang et al.
G. polyantha Stem bark Cameroon
(2005)
Triterpenoi
G. edulis Root bark Tanzania Magadula (2010)
ds
Momo et al.
G. lucida Stem bark Cameroon
(2011)
Lannang et al.
Oleanolic acid (81) G. polyantha Stem bark Cameroon
(2005)
G. lucida Stem bark Cameroon Momo et al.
Chapter 4 Phytochemistry of African Garcinia Plants 81
Where
Class Name Plant species Part Reference
collected
(2011)
Lannang et al.
Lupeol (82) G. polyantha Stem bark Cameroon
(2005)
G. edulis Root bark Tanzania Magadula (2010)
Magadula et al.
Achilleol A (83) G. semseii Stem bark Tanzania
(2008)
Lupeol acetate (84) G. edulis Root bark Tanzania Magadula (2010)
Lannang et al.
Garcinane (85) G. polyantha Root bark Cameroon
(2008)
Lannang et al.
Magnificol (86) G. polyantha Root bark Cameroon
(2008)
Betulinic acid (87) G. lucida Stem bark Cameroon Fotie et al. (2007)
Momo et al.
G. lucida Stem bark Cameroon
(2011)
Momo et al.
Putranjivic acid (88) G. lucida Stem bark Cameroon
(2011)
Methyl putranjivate Momo et al.
G. lucida Stem bark Cameroon
(89) (2011)
G. Komguem et al.
Smeathxanthone A (10) Stembark Cameroon
smeathmannii (2005)
Lannang et al.
G. polyantha Root bark Cameroon
(2008)
G. Komguem et al.
Smeathxanthone B (11) Stembark Cameroon
smeathmannii (2005)
Lannang et al.
G. polyantha Root bark Cameroon
(2008)
1,3,5-Trihydroxyxantho G. Komguem et al.
Stembark Cameroon
ne (41) smeathmannii (2005)
G. polyantha Wood trunk Cameroon Louh et al. (2008)
1,3-dihydroxyxanthone G. Komguem et al.
Stembark Cameroon
(90) smeathmannii (2005)
Xanthones
G. polyantha Wood trunk Cameroon Louh et al. (2008)
Waterman and
Rheediaxanthone (91) G. staudtii Stembark Nigeria
Hussain (1982)
Rheediaxanthone A Waterman and
G. staudtii Stembark Nigeria
(92) Hussain (1982)
Bangangxanthone A Lannang et al.
G. polyantha Stem bark Cameroon
(28) (2005)
Bangangxanthone B Lannang et al.
G. polyantha Stem bark Cameroon
(29) (2005)
1,5-Dihydroxyxanthone Lannang et al.
G. polyantha Stem bark Cameroon
(30) (2005)
Waffo et al.
G. afzelii Stem bark Cameroon
(2006)
2-Hydroxy-1,7-dimetho G. polyantha Stem bark Cameroon Lannang et al.
82 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
Where
Class Name Plant species Part Reference
collected
xyxanthone (31) (2005)
1,4,5-Trihydroxy-3-(3-
G. Mbwambo et al.
methylbut-2-enyl)-9H- Root bark Tanzania
livingstoneii (2006)
xanthen-9-one (7)
G. South Sordat-Diserens
Root bark
livingstoneii Africa et al. (1992)
6,11-Dihydroxy-3-meth
yl-3-(4-methylpent-3-e G. Mbwambo et al.
Root bark Tanzania
nyl)pyrano[2,3-c]xanth livingstoneii (2006)
one (8)
G. South Sordat-Diserens
Root bark
livingstoneii Africa et al. (1992)
4[(E)-3,7-Dimethylocta
-2,6-dienyl]-1,3,5-trihy G. Mbwambo et al.
Root bark Tanzania
droxy-9H-xanthen-9-on livingstoneii (2006)
e (9)
G. Mbwambo et al.
Garcilivin A (15) Root bark Tanzania
livingstoneii (2006)
G. South Sordat-Diserens
Root bark
livingstoneii Africa et al. (1992)
G. Mbwambo et al.
Garcilivin B (93) Root bark Tanzania
livingstoneii (2006)
G. South Sordat-Diserens
Root bark
livingstoneii Africa et al. (1992)
G. Mbwambo et al.
Garcilivin C (16) Root bark Tanzania
livingstoneii (2006)
G. South Sordat-Diserens
Root bark
livingstoneii Africa et al. (1992)
Waffo et al.
Afzeliixanthone A (21) G. afzelii Stem bark Cameroon
(2006)
Afzeliixanthone A B Waffo et al.
G. afzelii Stem bark Cameroon
(22) (2006)
1,7-Dihydroxyxanthone Waffo et al.
G. afzelii Stem bark Cameroon
(94) (2006)
1,3,7-Trihydroxy-2-(3-
Waffo et al.
methylbut-2-enyl)xanth G. afzelii Stem bark Cameroon
(2006)
one (95)
Rheediaxanthone-B Ampofo et al.
G. polyantha Stem bark Cameroon
(96) (1986)
Isorheediaxanthone-B Ampofo et al.
G. polyantha Stem bark Cameroon
(97) (1986)
12b-Hydroxy-des-D-ga G. South Sordat-Diserens
Root bark
rcigerrin A (6) livingstoneii Africa et al. (1992)
6,11-Dihydroxy-2,2-di
G. South Sordat-Diserens
methyl-pyrano[3,2-c]xa Root bark
livingstoneii Africa et al. (1992)
nthone (17)
4-(3,7-Dimethylocta- G. Root bark South Sordat-Diserens
Chapter 4 Phytochemistry of African Garcinia Plants 83
Where
Class Name Plant species Part Reference
collected
2, 6-dienyl) livingstoneii Africa et al. (1992)
-1,3,5-trihydroxy -9H-
xanthone (18)
South Sordat-Diserens
Garcigerrin A (4) G. gerrardii Root bark
Africa et al. (1989)
South Sordat-Diserens
Garcigerrin B (5) G. gerrardii Root bark
Africa et al. (1989)
2-(1',l'-Dimethylprop-2'
South Sordat-Diserens
-enyl)-1,4,5-trihydroxy G. gerrardii Root bark
Africa et al. (1989)
xanthone (98)
Waterman et al.
Macluxanthone (99) G. ovalifolia Stem bark Cameroon
(1980)
1,3,5-Trihydroxy-4,8-(3
Waterman and
,3-dimethylallyl)xanth G. quadrifaria Stem bark Cameroon
Hussain (1982)
one (100)
Garceduxanthone (37) G. edulis Root bark
Tanzania Magadula (2010)
Forbexanthone (101) G. edulis Root bark
Tanzania Magadula (2010)
Waterman and
Pyranojacareubin (102) G. densivenia Stem bark Cameroon
Crichton (1980)
Ampofo and
Nervosaxanthone (103) G. nervosa Nigeria
Waterman (1986)
Garciniaxanthone I Lannang et al.
Root bark Cameroon
(104) (2008)
Lannang et al.
Chefouxanthone (105) Root bark Cameroon
(2008)
Polyanxanthone A (38) Wood trunk Cameroon Louh et al. (2008)
Polyanxanthone B (39) Wood trunk Cameroon Louh et al. (2008)
Polyanxanthone C (40) Wood trunk Cameroon Louh et al. (2008)
1,3,6,7-Tetrahydroxyxa
Wood trunk Cameroon Louh et al. (2008)
nthone (106)
1,6-Dihydroxy-5-metho
Wood trunk Cameroon Louh et al. (2008)
xyxanthone (42)
1,3,5,6-Tetrahydroxyxa
Wood trunk Cameroon Louh et al. (2008)
nthone (107)
1,2-Dihydroxyxanthone Momo et al.
G. lucida Stem bark Cameroon
(108) (2011)
1-Hydroxy-3-methoxyx Momo et al.
G. lucida Stem bark Cameroon
anthone (109) (2011)
Where
Class Name Plant species Part Reference
collected
ta
G.
Ngoupayo et al.
Brevipsidone C (46) brevipedicella Stem bark Cameroon
(2008)
ta
G.
Ngoupayo et al.
Brevipsidone D (47) brevipedicella Stem bark Cameroon
(2008)
ta
Waffo et al.
-Sitosterol (110) G. afzelii Stem bark Cameroon
(2006)
Lannang et al.
G. polyantha Root bark Cameroon
(2008)
Momo et al.
G. lucida Stem bark Cameroon
(2011)
-Sitosterol-glucopyran
G. lucida Stem bark Cameroon Fotie et al. (2007)
oside (111)
Parveen et al.
Stigmasterol (112) G. nervosa Dried leaf Nigeria
(2004)
Momo et al.
G. lucida Stem bark Cameroon
(2011)
Stem bark, Hussain and
Conrauanalactone (113) G. conrauana Cameroon
leaf, seed Waterman (1982)
3-(3,3-Dimethylallyl
Stem bark, Hussain and
)-conrauanalactone G. conrauana Cameroon
leaf, seed Waterman (1982)
(114)
5,7-Dihydroxychromon Stem bark, Hussain and
G. conrauana Cameroon
e (115) leaf, seed Waterman (1982)
3-Hydroxy-5-(heptade
Hussain and
c-8-enyl)-tetrahydrofur G. mannii Stem bark Cameroon
Waterman (1982)
an-2-one (116)
Niwa et al.
Garcifuran A (117) G. kola Dried root Nigeria
(1994a)
Terashima et al.
G. kola Dried stem Nigeria
(1999b)
Niwa et al.
Garcifuran B (118) G. kola Dried root Nigeria
(1994a)
Terashima et al.
Garcinal (25) G. kola Dried seed Nigeria
(1997)
Terashima et al.
Garcinoic acid (26) G. kola Dried seed Nigeria
(1997)
Niwa et al.
Garcipyran (119) G. kola Dried root Nigeria
(1994b)
2,4-Dimethoxy-6-hydro Niwa et al.
G. kola Dried root Nigeria
xyacetophenone (120) (1994b)
Dihydrochelerythrine
G. lucida Stem bark Cameroon Fotie et al. (2007)
(48)
6-Acetonyldihydrochel
G. lucida Stem bark Cameroon Fotie et al. (2007)
erythrine (49)
Chapter 4 Phytochemistry of African Garcinia Plants 85
Where
Class Name Plant species Part Reference
collected
Lucidamine A (50) G. lucida Stem bark Cameroon Fotie et al. (2007)
DR Dibwe et al.
Damnacanthal (20) G. huillensis Root bark
Congo (2007)
DR Dibwe et al.
Nordamacanthal (121) G. huillensis Root bark
Congo (2007)
2-Formyl-1-hydroxyant DR Dibwe et al.
G. huillensis Root bark
hraquinone (122) Congo (2007)
DR Dibwe et al.
Lucidin (123) G. huillensis Root bark
Congo (2007)
Lucidin 1,3-dimethyl DR Dibwe et al.
G. huillensis Root bark
ether (124) Congo (2007)
Damnacanthol DR Dibwe et al.
G. huillensis Root bark
1-methyl ether (125) Congo (2007)
Rubiadin 1-methyl DR Dibwe et al.
G. huillensis Root bark
ether (126) Congo (2007)
DR Dibwe et al.
Rubiadin (127) G. huillensis Root bark
Congo (2007)
Rubiadin 3-methyl DR Dibwe et al.
G. huillensis Root bark
ether (128) Congo (2007)
DR Dibwe et al.
Tectoquinone (129) G. huillensis Root bark
Congo (2007)
Rubiadin dimethyl DR Dibwe et al.
G. huillensis Root bark
ether (130) Congo (2007)
DR Dibwe et al.
Pachybasin (131) G. huillensis Root bark
Congo (2007)
Terashima et al.
-Tocotrienol (132) G. kola Seed Nigeria
(1997)
30-Hydroxycycloarteno Nyemba et al.
G. lucida Stem bark Cameroon
l (133) (1990)
31-Norcycloartenol Nyemba et al.
G. lucida Stem bark Cameroon
(134) (1990)
24,25-Epoxy-31-norcyc Nyemba et al.
G. lucida Stem bark Cameroon
loartenol (135) (1990)
Sesamin (136) G. lucida Stem bark Cameroon Fotie et al. (2007)
Trans-fagaramide (137) G. lucida Stem bark Cameroon Fotie et al. (2007)
4.2 Benzophenones
4.2 Flavonoids
4.3 Triterpenoids
From African Garcinia plants, only nine (9) triterpenoids have been reported
(Table 5). These include friedelin (80), isolated from the stem bark of G.
ovalifolia (Waterman et al., 1980), G. polyantha (Lannang et al., 2005) and G.
edulis (Magadula, 2010). Other pentacyclic triterpenoids, oleanoic acid (81) and
lupeol (82) were isolated from the stem barks of G. polyantha (Lannang et al.,
2005), while, from the root bark of G. edulis, lupeol was isolated together with
its acetate (84) (Magadula, 2010). In another study from G. semseii, a plant
which is endemic to Tanzania, a monocyclic triterpene, achilleol A (83) was
reported from its stem bark (Magadula et al., 2008). Other triterpenoids isolated
from African Garcinia plants are indicated in Table 5.
4.4 Xanthones
from the genus Garcinia gave a variety of prenylated xanthones, some of them
exhibited a wide range of biological and pharmacological activities, including
cytotoxic, antimicrobial, antifungal, antioxidant, antimalarial, anti-HIV-1,
anti-obesity and anti-parasitic activities (Minami et al., 1994). Many of these
xanthones are found in the pericarp of the true mangosteen fruit, G. mangostana,
which is a highly investigated plant in the genus Garcinia (Obolskiy et al.,
2009).
Apart from the the 4 classes of compounds mentioned above, a range of other
compounds have also isolated from Garcinia plants. These include
brevipsidones (44-47) previously isolated from the stem bark of a Cameroonian
plant, G. brevipedicellata (Ngoupayo et al., 2008), and conrauanalactones
(113-114) isolated from the stem bark, leaves and seeds of G. conrauana
(Hussain and Waterman, 1982). Furthermore, garcifurans (116-119) were
90 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
isolated from G. kola (Niwa et al., 1994; Terashima et al., 1999) while the
commonly known phytosterols, stigmasterol (110) and -sitosterol (112) were
also reported from many other Garcinia species growing in Africa (Table 5).
OH OH
HO O O HO O O
O OH O OH
51 52
OH OH
HO HO O R HO O
O O O O
R
54 H
53
55 OH
O OH
OH
OH
HO HO O
HO O O
O OH
O O
O OH
57 58
56
OH OH
OH
HO O OH
OH
HO O
HO O+
OH O OH
R R' OH
HO O OH O
H OH
R 59 H
63
R' 62
60 H OH
OH O
61 OH H
OH
OH
HO O
HO O
OCH3
R HO O
OH O OH
OH O OH
HO O
HO O R OH O
64 H 69 OH
65 OCH3
OH O
OH O 66 glc
70
67 H
68 OH
OH R7 O
R2
HO O R3
R1
OH OH O
R6 R4
HO O OH O OH R5
HO O
R1 R2 R3 R4 R5 R6 R7
OH O H
73 H OCH3 OH OCH3 OCH3 OH
71 OH O
OH 74 OCH3 H OH OCH3 OCH3 H OH
OH 72
75 OCH3 H H OH H H OCH3
HO O O
HO OH
OH OH
OH
OH O OH O OH OH
OH
HO O HO O HO O
HO O
OH
OH OH OH
OH O OH O OH O
OH O
76 78 79
77
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
92 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
H H H H H
COOH
H H
O HO HO
H H
80 81 82
HO H
H
H3COO
H
83
84
H
H OH
HO H COOH H COOH
H
H H
H3COO
H HO HO
H H
85 86 87
O
OR
R
88 H
89 CH3
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
Chapter 4 Phytochemistry of African Garcinia Plants 93
O OH OH O
OH O
O
O OH O OH
O O O
OH
OH
90 91 92
OH OH
O
OH
O O OH
O OH
OH O HO
HO
O OH O
O OH
93 94 95
OH
O OH O OH
O OH
O O OH
OH O O
OH O OH OH
96 98
97
OH O OH O OH
O OH
O O OH O O OCH3
OH OH
O OH
OH 101
99
100
OH O OH
O OH O OH
O OCH3
OH
O O O HO O OH
O
OH OH
103
102 104
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
94 Garcinia Plant Species of African Origin: Ethnobotanical, Pharmacological and Phytochemical Studies
O OH O OH
OH O OH HO
HO O OH HO O OH
O OCH3
OH
OH
106 107
105
H
O OH
O OH OCH3 H
OH
H H
O HO
O
109 110
108
OH
R
H O O C14H29
H
H H
R
H H H H 113 H
HO
Glc
114
111 112
HO O HO HO
OH
(CH2)6CH=CH(CH2)7CH3 H3CO
O O
OH O O
116
115 117
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
Chapter 4 Phytochemistry of African Garcinia Plants 95
O
OCH3 O OH
HO HO OCH3
H3CO
HO HO
OCH3
O OH
119 120
118
O R1 O R1
CHO CH2OH
R2 R2
O O
R1 R2 R1 R2
20 OCH3 OH 123 OH OH
121 OH OH 124 OCH3 OCH3
O R1
CH3 122 H H 125 OCH3 OH
R2
O O OCH3 O
R1 R2 CH3
126 OCH3 OH
OCH3
127 OH OH
O O OH
128 H H
130 131
129 OH OCH3
HO
O
CH3
132
HO
H
HO
H
OH
133 134
O
O O
O
N O
HO H
H O
O O O
Fig. 21. Structures of compounds isolated from African Garcinia plants (Cont).
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