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CHEMICAL CONSTITUENTS OF THE TWIGS OF MANGIFERA INDICA (MANGGA TELOR)
HASBARINDA BINTI HASAN
BACHELOR OF SCIENCE (Hons.) CHEMISTRY FACULTY OF APPLIED SCIENCE UNIVERSITY TECHNOLOGY MARA
NOVEMBER 2008
CHEMICAL CONSTITUENTS OF THE TWIGS OF MANGIFERA INDICA (MANGGA TELOR)
HASBARINDA BINTI HASAN
Final Year Project Report Submitted in Partial Fulfillment of the Requirements for the
Degree of Bachelor of Science (Hons.) Chemistry in the Faculty of Applied Sciences
Universiti Teknologi MARA
NOVEMBER 2008
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ACKNOWLEDGEMENT
Alhamdulillah, grateful to Allah S.W.T of His bless and consent. Finally we are able to finish
my final project.
My special thanks to Dr. Norizan Ahmat as asupervisor for supporting me in preparing the
final year project. Beside that, she also provides a lot of information on prepation of the
report.
Beside that, special acknowledgement is due to my beloved parents for their ongoing support
and understanding in preparing the final report. May Allah blesses them.
More than that thanks to all our friends because share the opinion with us and realize us from
wrong in this project progress. We also not forget to thank to the entire person who are
involve in this project study. Your support and cooperation are so meaningful to us.
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TABLE OF CONTENTS
Page ACKNOWLEDGEMENT iii TABLE OF CONTENTS iv LIST OF TABLE vi LIST OF FIGURE vii LIST OF ABBREVIATIONS viii ABSTRACT ix ABSTRAK x
CHAPTER 1 INTRODUCTION 1.1 Natural product 1 1.2 Application of natural product 3 1.3 Significance of study 3 1.4 Objective of study 3
CHAPTER 2 LITERATURE REVIEW 2.1 Family of Anacardiaceae 4
2.1.1 Commercial uses of Anacardiaceae 4 2.1.2 Medical uses of Anacardiaceae 5
2.2 Genus Mangifera 7 2.3 Species Mangifera indica 9
2.3.1 Uses ofMangifera indica 11 2.3.1.1 Common uses ofMangifera indica 11 2.3.1.2 Medical and Traditional uses ofMangifera indica 11
2.3.2 Phytochemical study ofMangifera indica 13
CHAPTER 3 MATERIAL AND METHODOLOGY 3.1 Material 17
3.1.1 Plant material 17 3.1.2 Chemicals 17 3.1.3 Instruments 18
3.2 Methodology 18 3.2.1 Solvent extraction 18 3.2.2 Isolation process 18 3.2.3 Elucidation process 20
3.3 Chromatographic methods 23
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3.3.1 Vacuum liquid chromatography 23 3.3.2 Radial chromatography 24 3.3.3 Preparative chromatography 25
CHAPTER 4 RESULTS AND DISCUSSION 4.1 Isolation of compound 1 26 4.2 Elucidation process 26
4.2.1 1 H NMR spectroscopy 26 4.2.2 13 C NMR spectroscopy 29 4.2.3 DEPT spectrum 31
CHAPTER 5 CONCLUSION AND RECOMMENDATIONS 32
CITED REFERENCES 33
CURRUCULUM VITAE 35
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LIST OF TABLES
Table Caption Page
2.1 Commercial uses of ANACARDIACEAE 5
2.2 Medical uses of ANACARDIACEAE 5
2.3 Scientific classification 6
2.4 Species of Mangifera with distribution and uses 8
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LIST OF FIGURES
Figure Caption Page
2.1 Mangifera indica tree and twigs 10
3.1 TLC for compound AS14 solvent system 8.5:1.5 20 CHCl3:MeOH
3.2 Extraction, isolation and elucidation of twigs 22 Mangifera indica
4.1 TLC profile for compound 1 26
4.2 1 H NMR spectrum and structure for compound 1 28
4.2 13 C NMR spectrum and structure for compound 1 30
4.2 DEPT spectrum for compound 1 31
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LIST OF ABBREVIATIONS
CC : Column Chromatography
VLC : Vacuum Liquid Chromatography
RC : Radial Chromatography
TLC : Thin Layer Chromatography
FTIR : Fourier Transform Infrared
GCMS : Gas Chromatography Mass Spectrometry
1 HNMR : Proton Nuclear Magnetic Resonance
13 CNMR : Carbon13 Nuclear Magnetic Resonance
UVVis : UltravioletVisible
MeOH : Methanol
C6H12 : Haxane
EtOAc : Ethyl Acetate
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ABSTRACT
CHEMICALS CONSTITUENTS OF THE TWIGS OF MANGIFERA INDICA (MANGGA TELOR)
a study of the chemical constituents of Mangifera indica twigs was conducted. The dried powder of twigs was extracted with methanol. The isolation of the compounds was achieved by chromatographic techniques. Structure determinations were done using 1 H NMR, 13 C NMR, and DEPT. From the twigs of Mangifera indica , 4, 8Bishydroxymethyl7(1 hydroxy1methylethyl)1(3,4,6trihydroxy5hydroxymethyltetrahydropyran2yl)478 trihydronaphthalen2one were isolated.
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ABSTRAK
KANDUNGAN KIMIA DI DALAMRANTING MANGIFERA INDICA
Kajian terhadap kandungan kimia di dalam ranting Mangifera indica telah di jalankan. Ranting Mangifera indica yang telah kering diekstrak dengan menggunakan teknik kromatografi. Penentuan struktur kimia telah dikenalpasti menggunakan 1 H NMR, 13 C NMR, dan DEPT. 4, 8Bishydroxymethyl7(1hydroxy1methylethyl)1(3,4,6trihydroxy5 hydroxymethyltetrahydropyran2yl)478trihydronaphthalen2one telah dikenalpasti dari ranting tumbuhan itu
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CHAPTER 1
INTRODUCTION
1.1 Natural product
Natural product preparations have historically been the major source of
pharmaceutical agents. Analysis of FDA newdrug approvals from 1981 to 2002
reveals that natural products continued to play a pivotal role during that time, even
if the industry had turned to other discovery strategies (Newman et al., 2003).
Indeed, more than 90% of current therapeutic classes derive from a natural
product prototype and interestingly, even today, roughly twothirds to three
quarters of the world’s population relies upon medicinal plants for its primary
pharmaceutical care (World Health Organization, 2002). Those ‘‘medicinal
plants’’ are either preparations of or natural product substances from plants that
has potential utility as pharmaceutical agents (Balunas & Kinghorn, 2005).
The term natural products refer to herbs, herbal concoctions, dietary supplements,
traditional Chinese medicine, or alternative medicine (Holt & Chandra, 2002).
Natural product have been investigated and utilized to alleviate disease since early
human history. In the past, traditional peoples or ancient civilizations depended
greatly on local flora and fauna for their survival. They would experiment with
various berries, leaves, roots, animal parts or minerals to find out what effects they
had. As a result, many crude drugs were observed by the local healer or shaman to
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have some medical use. Although some preparations may have been dangerous, or
worked by a ceremonial or placebo effect, traditional healing systems usually had
a substantial active pharmacopoeia, and in fact most western medicines up until
the 1920s were developed this way. The extensive records of Chinese medicine
about response to Artemisia preparations for malaria also provided the clue to the
novel antimalarial drug artemisinin (Holt & Chandra, 2002).
In 1990s, 80% of all medicines were obtained from the roots, barks, and the
leaves of the plant. Today, more than two thirds of the world’s plant species and at
least 35,000 are estimated to have medical value. One of the countries that rich of
flora and fauna is Malaysia. In Malaysia, at least 500 genera and more than 1200
species flora were used in the traditional medicine. The diversity of Malaysia flora
provided many investing new chemical compounds that have provided effect to
human body. The first report of phytochemical survey of plant in Malaysia was
carried out by Arthur in 1954, and this was followed by a several similar report
right up to the 90s. This stills proven strategic approach whereby plant with
alkaloids is chosen for further detail investigation.
Mangifera indica more commonly known as the Mango tree is an important
medicinal plant and can form as natural product. A standard aqueous stem bark
extract from selected species of Mangifera indica, named Vimang, has been used
as phytomedicine in Cuba (Nũňez, 2002). Mangifera indica (Anacardiaceae)
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grows in the tropical and subtropical regions and its parts are used commonly in
folk medicine for a wide variety of conditions (Coe & Anderson, 1996).
1.2 Application of natural product
Natural products have been used in many purposes. For example, it has been used
in the traditional medicine, biopharmaceuticals, flavors and fragrance, hair color,
food, detergent, biopesticides, and also in the beauty product.
1.3 Significance of study
Mangifera indica has been widely used in traditional medicine for treatment of
diseases. The chemical content in Mangifera indica includes mangiferin and
lactase, as well as enzymes which aid in digestion and intestinal health. Since their
chemical constituents have not been fully discovered, this research may lead to the
discovery of new chemical constituents.
1.4 Objective of the study
The objectives of this study are as follows:
1. To prepared crude extracts from the twigs ofMangifera indica using methanol
as a solvent.
2. To isolate the chemical compounds of Mangifera indica using
chromatographic techniques.
3. To elucidate the structure of the isolated compounds using spectroscopic
method such as NMR ( 1 H and 13 C NMR), FTIR, UV and GCMS.
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CHAPTER 2
LITERATURE REVIEW
2.1 FAMILY of ANACARDIACEAE
The family Anacardiaceae is represented with about 70 genera and 600 species of
mostly trees or climbers or shrubs the bark usually resinous are also found in
warm temperate regions of Europe, eastern Asia, and the Americas. The leave is
simple to pinnate, alternate, rarely opposite, and showing a straight parallel
secondary nerves. The flowers of the family anacardiaceae usually universal either
polygamous, monoecious, or dioecious, usually readily symmetrical with
hypogynous disc, in elaborate panicles, with 3 or 5 sepals, the flowers have 3 or 5
petals or sometimes none petals. The flowers have 5 or 10 stamens and usually the
gynoecium’s made of 1 to 5 carpel’s forming a 1 to 3 loculate ovary, each cell
containing a single ovule (Benson, 1996 ; Christophe, 2002).
2.1.1 Commercial uses of ANACARDIACEAE
Each species in Anacardiaceae have their own uses, the table 2.1 show the
commercial uses for each species in Anacardiaceae (Kubo et al. 1994) .
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Table 2.1 Commercial uses of ANACARDIACEAE
Species Part Uses
Nut shell Used in manufacture of brake of lining
and electrical insulations.
Used as electrical parts of the aircraft.
Anacardium
occidentale
Fruit insect control agent
Semecarpus
anacardium
Shell used as an indelible ink to mark
laundry
Rhus typhina Fruits Used by American Indians to make a
drink. Source: (Kubo et al. 1994)
2.1.2 Medical uses of ANACARDIACEAE
Each species in Anacardiaceae have their own uses, the table 2.2 show the
madical uses for each species in Anacardiaceae (Smit et al. 1995; Morton 1978;
Boericke 1984; Goudgaon et al. 1985).
Table 2.2 Medical uses of ANACARDIACEAE
Species Part Uses
Pistacia ientiscus Nut shell Produce mastic
Rhus coriaria Shell Used as a bioactive agent that is anti inflammatory and analgesic tannins and also as antiHIV flavonoids.
Anacardium Bark Used to medicate the diarrhea disease. used as massage oil for rheumatism
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Occidentale Nut shell Used in indigenous medicine as a rubefacient and vesicant
Fruit Useful as an anaesthetic in leprosy and psoriasis, and as a blister in the treatment of warts, ulcers.
Rhus glabra Used as an astringent, antiseptic, in gargles, and as refrigerant and diuretic. Useful in halting diarrhea used as antibiotic
Semecarpus
anacardium
Nuts Used as anticancer
Source: Smit et al. 1995; Morton 1978; Boericke 1984; Goudgaon et al. 1985
Table 2.3 show the scientific classification of family Anacardiaceae
Table 2.3 Scientific classification
Kingdom Plantae
Phylum Magnoliphyta
Class Magnoliopsida
Order Sapindales
Family Anacardiaceae
Genus Mangifera
Species Mangifera Indica
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2.2 Genus Mangifera
The genus ofMangifera belongs to the order Sapindales in the family. The greater
numbers of Mangifera species are found in the Malay Peninsula, Indonesia at the
Borneo and Sumatra, Thailand and Philippines. At least nine species are grown in
the village orchards in the Malay Peninsula and five of these are common. From
the five spicies the Indian Mango (M.indica), the Kwini (M.odorata), the Binjai
(M.aesia) have been found in the forest so that they maybe regarded as truth
native (Mat Salleh & Latif, 2002).
The characteristic for the genus Mangifera are that they have large, unbuttressed
trees with white latex in the unripe fruits. The bark is light to darkgreen brown
shallowly fissured with broad flat ridges. The leaves are spirally arrangement;
simple generally with upcurled sides and the younger leaves is violet color.
Mangifera have very small flowers in the large terminal panicles with 45 sepals
and petals and 15 stamens. The fruits are large, fleshy, and oblong (Christophe
2002).
There are about 40 species in Asia, and about 20 species will be found in Malaysia
where mostly at the lower land and few in the mountains. The species of the
Mangifera are show in the table 2.4 (Mat Salleh & Latif, 2002)
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Table 2.4 Species of genus Mangifera with distributions and uses.
Species Common name Distribute in Malaysia
Uses
M.indica Mango (Mangga or Mempelam)
Camaron Highland Kelantan
Antioxidant. Antiinflammatory activity.
M. caesia Binjai Malacca Fruit can be eaten
M.foetida House mango (Bacang or Machang)
Perak, Johor, The fruits are used in curries or for pickles.
M.microphylla Rawa Kedah and Terengganu
M.odorata Kwini or Kwining Common in Malaysia
M.pentandra Pauh or Mempelam bemban
Kelantan Fruit can be eaten
M.lagenifera Lanjut Malacca
M.longipetiolata Topah or Sepam Malaysia forest
Source: Mat Salleh & Latif, 2002
Mangifera has the medicinal properties that are used in the world. For example, in
Nigerian the extraction from the leaves of Mangifera indica are used as an
antidiabetic agent. Mangifera genus also has an excellent nutritional source,
containing many vitamins, minerals, and antioxidants, as well as enzymes such as
mangiferin and lactase which aid in digestion and intestinal health. It is also used
in some parts of Southeast Asian world as a supplement for sexual potency (Coe
& Anderson, 1996).
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2.3 SpeciesMangifera indica
The Mangifera indica (mango) is one of the choicest fruit crops of tropical and
subtropical regions of the world, especially in Asia. Its popularity and importance
can easily be realized by the fact that it is often referred as ‘King of fruits’ in the
tropical world (Singh, 1996). The common name of Mangifera indica is Mango.
The origin of Mangifera indica is in northeast India, north western Myanmar and
Bangladesh than later spread to the rest of Asia by themselves and with the help of
humans. Mangifera indica nowadays can be found in India, Sri Lanka,
Bangladesh, Myanmar, Thailand, Kampuchea, Vietnam, Laos, southern China,
Malaysia, Singapore, Indonesia, Brunei, the Philippines, Papua New Guinea, and
the Solomon and Caroline Islands. Maximum species diversity exists in western
Malaysia and about 28 species are found in this region (Smith et al, 2004).
The characteristic of Mangifera indica (mango) is the trees are deeprooted,
symmetrical evergreens that the height is about 90 feet and widths of 80 feet. The
trees have simple alternate leaves that are 12 to 20 inches in length and yellow
green, purple, or copper in color when young. When mature the leaves change to
leathery, glossy, and deep green in color. The flower is 3 inches with a greenish
yellow, white, pale cream, or even pinkish. The flower has fragrant, with 620”
long panicle, 2” long flower buds and 36 petals. The mature terminal branches
bear pyramidal flower panicles that have several hundred white flowers that are
about a 1/4 inch wide when open. The fruit weighs about 1/4 pound to 3 pounds.
Fruit may be round, ovate, or obovate depending on the variety. Mature fruit has a
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characteristic fragrance and a smooth, thin, tough skin. The flesh of ripe mangos is
pale yellow to orange. The fruit has one seed that is flattened and sticks to the
flesh. The seed contains one or more embryos depending on the variety or type.
(Mat Salleh & Latif, 2002; Sarwal, 2000).
Figure 2.1 showed the part in Mangifera indica tree
Figure 2.1 Mangifera indica tree and twigs
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2.3.1 Uses ofMangifera indica
2.3.1.1 Common uses ofMangifera indica
Mangos have long been recognized as more than just edible ripe fruit. The edible
uses of the fruit include nonripe fruit, seed, and processed products such as
achars, chutneys, preserves, etc. The fruit is eaten for its nutritional value, its
medicinal value, and for its pleasant flavor. The fruit and its byproducts are used
for animal fodder, and the timber is used for canoe building and making charcoal.
Today mango and its flavor are added to many products, such as fruit juices, ice
creams, wines, teas, breakfast cereals, muesli bars, and biscuits (Ian & Bally,
2006).
Mangos are a highly nutritious fruit containing carbohydrates, proteins, fats,
minerals, and vitamins, in particular vitamin A (beta carotene), B1, B2, and
vitamin C (ascorbic acid). As the fruit ripens, concentrations of vitamin C
decrease and glucose, fructose, and sucrose concentrations increase. In Sarawak
the young leaves of the related species Mangifera pajang are eaten as vegetables.
Mangifera also used as a drink or tea where alcoholic beverages made from
mangos include wines and liquors made in Australia and India. Specialty teas are
occasionally flavored with fragrant mango flowers (Ian & Bally, 2006).
2.3.1.1 Medical and traditional uses ofMangifera indica
All parts of the Mangifera indica (mango) plant from the seeds and flowers to the
leaves and gum are used in traditional South Asian medicine, but the fruits are
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most important. In India, the Mangifera indica is used traditionally for its
vermifuge activity. And other uses in India, fruit sap have been used to treat the
pain of bee and scorpion stings (Ian & Bally, 2006).
In Samoa, a bark infusion has been a traditional remedy for mouth infections in
children (pala gutu), and in Tonga, infusions of leaves of Mangifera indica, the
orange (Citrus sinensis), and other species are used to make a potion to treat
relapse sickness (kita). In Togo the stem bark is used as an antidiarrhoeal and
antimicrobial, the leaves are reported to have anticancer activity. In South Asian
folk medicine, rheumatism and diphtheria is treated using the astringent bark of
the mango tree. Mango stem bark has been traditionally used in many countries
for the treatment of menorrhagia, diarrhoea, syphilis, diabetes, scabies, cutaneous
infections, anaemia using an aqueous extract obtained by decoction as reported in
the Napralert Database (Scartezzini & Speroni, 2000).
In the western medicine, the fruits, bark and seeds of mango plants have been
scientifically shown to possess a range of healthgiving properties. The fruits of
Mangifera indica can help to prevent colon cancer, especially in cases where there
is a lack of fibre in the diet. The fruits also contain a compound called mangiferin,
which has several medicinal attributes. It is particularly useful in promoting the
action of the heart and excretion of urine, calming inflammation, treating diabetes
and as an antioxidant. Fruits also contain the chemicals gallic acid and quercetine,
which give protection against viruses. Chemical compounds in extracts from the
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bark of mango trees have been shown to protect against diarrhoea. The powdered
seeds also have antimicrobial activity. (Shahidi & Naczk,2000)
Studies on the pharmacological properties of mangiferin reveal that this flavonoid
compound possesses antitumor, antiviral, antioxidant, antidiabetic,
immunomodulatory, and vascular modulatory activity (Beltran, 2004).
Highperformance liquid chromatography (HPLC) alone or HPLC combined with
mass spectrometry is widely employed for determination of mangiferin quality
and quantity in pharmaceutical, pharmacokinetic or pharmacological studies (Lai
et al, 2003).
2.3.2 Phytochemical study ofMangifera Indica
Nong et al, 2005 have isolated the compound from the bark of Mangifera indica.
The compound is Mangiferin [1]. The compound also found in the fruit of
Mangifera indica (Bathia et al, 1967) (2betadglucopyranosyl 1,3,6,7
tetrahydroxyxanthen9one)
O
OH
Glu
HO
O
OH
OH
[1]
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