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STUDIES ON THE CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITIES

OF ESSENTIAL OILS OF BOESENBERGIA SPP.

ZAINAH BINTI ADAM

This report is submitted in partial fulfillment of the requirements for the degree of Bachelor of
Sciences with Honors in Resource Chemistry

Faculty of Resource Science and Technology


UNIVERSITI MALAYSIA SARAWAK
2008
TABLE OF CONTENTS
Contents Page

Declaration ii
Acknowledgement iii
List of Figures iv
List of Tables vi
Abstract vii
Abstrak vii

CHAPTER 1 INTRODUCTION
1.1 Introduction 1
1.2 Objectives 4

CHAPTER 2 LITERATURE REVIEW


2.1 Zingiberaceae Family
2.1.1 General 5
2.1.2 Medicinal Uses of Zingiberaceae family 6
2.2 Boesenbergia spp.
2.2.1 General 7
2.2.2 Medicinal Uses of Boesenbergia spp. 8
2.2.3 Phytochemical Studies of Boesenbergia spp. 9

2.2.3.1 Phenylpropanoids 9
2.2.3.2 Monoterpenes/Monoterpenoids 10
2.2.3.3 Sesquiterpenes/Sesquiterpenoids 11
2.2.3.4 Chalcones and derivatives 12
2.2.3.5 Flavanoids and derivatives 13
2.2.4 Biological Activities of Boesenbergia spp. 14
2.3 Extraction Methods
2.3.1 Steam-distillation 16
2.3.2 Cold Press Extraction 17

2.3.3 Supercritical Fluid Extraction (SFE) 17


CHAPTER 3 MATERIALS AND METHODS
3.1 Sampling 18
3.2 Extraction of Essential Oil 19
3.3 Instrumental Analysis of Essential Oils
3.3.1 Gas Chromatography/Flame Ionization Detection (GC/FID) 19
3.4 Qualitative and Quantitative Analysis
3.4.1 Qualitative Analysis 20
3.4.2 Percentages of Essential Oils 20
3.4.3 Semi-quantitative Analysis 21
3.4.4 Cluster Analysis 21
3.5 Bioassay
3.5.1 Brine Shrimp, Artemia salina Toxicity Test 22
3.5.2 Termiticidal Activity Test 23
CHAPTER 4 RESULTS AND DISCUSSION
4.1 Abundance of Essential Oil in Boesenbergia spp. 24
4.2 Determination of Kovats Indices for Standard 24
4.3 Composition of Essential Oils 27
4.3.1 Chemical Composition of the Essential Oils of Boesenbergia 27
parva
4.3.2 Chemical Composition of the Essential Oils of Boesenbergia 35
pulchella
4.3.3 Chemical Composition of the Essential Oils of Boesenbergia 39
gracilipes
4.3.4 Chemical Composition of the Essential Oils of Boesenbergia 46
burttiana
4.3.5 Chemical Composition of the Essential Oils of Boesenbergia 51
grandis
4.3.6 Chemical Composition of the Essential Oils of Boesenbergia 58
sp.
4.4 Comparison of Chemical Composition of Essential Oil in Six 66
Species of Boesenbergia
4.5 Cluster Analysis 70
4.6 Bioassay
4.6.1 Toxicity Test on Artemia salina 73
4.6.2 Termiticidal Toxicity Test on Nasutitermes sp. 77

CHAPTER 5 CONCLUSIONS AND RECOMMENDATIONS 79

REFERENCES 81
LIST OF FIGURES
Figures Page
Figure 1.1 : Example of Boesenbergia species found a) Boesenbergia curtisii white leaf- 3
sheaths b) Boesenbergia plicata red flower
Figure 2.1 : Boesenbergia species that can be found in the central part of Sarawak 8
a) Boesenbergia pulchella b) Boesenbergia oligosperma
Figure 3.1 : Bioassay apparatus for termiticidal activity test in contact condition. 21
Figure 4.1 : GC/FID chromatogram for standard mixture of n-alkane 26
Figure 4.2 : GC/FID chromatogram for the leaves oil of Boesenbergia parva 33
Figure 4.3 : GC/FID chromatogram for the stem oil of Boesenbergia parva 34
Figure 4.4 : GC/FID chromatogram for the rhizome oil of Boesenbergia parva 34
Figure 4.5 : GC/FID chromatogram for the fruit oil of Boesenbergia parva 35
Figure 4.6 : GC/FID chromatogram for the leaves oil of Boesenbergia pulchella 38
Figure 4.7 : GC/FID chromatogram for the stem oil of Boesenbergia pulchella 38
Figure 4.8 : GC/FID chromatogram for the rhizome oil of Boesenbergia pulchella 39
Figure 4.9 : GC/FID chromatogram for the leaves oil of Boesenbergia gracilipes 44
Figure 4.10 : GC/FID chromatogram for the stem oil of Boesenbergia gracilipes 45
Figure 4.11 : GC/FID chromatogram for the rhizome oil of Boesenbergia gracilipes 45
Figure 4.12 : GC/FID chromatogram for the leaves oil of Boesenbergia burttiana 50
Figure 4.13 : GC/FID chromatogram for the stem oil of Boesenbergia burttiana 50
Figure 4.14 : GC/FID chromatogram for the rhizome oil of Boesenbergia burttiana 51
Figure 4.15 : GC/FID chromatogram for the leaves oil of Boesenbergia grandis 56
Figure 4.16 : GC/FID chromatogram for the stem oil of Boesenbergia grandis 57
Figure 4.17 : GC/FID chromatogram for the rhizome oil of Boesenbergia grandis 57
Figure 4.18 : GC/FID chromatogram for the fruit oil of Boesenbergia grandis 58
Figure 4.19 : GC/FID chromatogram for the leaves oil of Boesenbergia sp. 65
Figure 4.20 : GC/FID chromatogram for the stem oil of Boesenbergia sp. 65
Figure 4.21 : GC/FID chromatogram for the rhizome oil of Boesenbergia sp. 66
Figure 4.22 : Dendogram obtained from cluster analysis for leaves oils of six 71
Boesenbergia spp.
Figure 4.23 : Dendogram obtained from cluster analysis for stem oils of six Boesenbergia 71
spp.
Figure 4.24 : Dendogram obtained from cluster analysis for rhizome oils of six 72
Boesenbergia spp.
Figure 4.25 : Dendogram obtained from cluster analysis for six species of Boesenbergia 73
sp.for all different parts combined
Figure 4.26 : Toxicity of the leaves oils of Boesenbergia spp. on Artemia salina 76
Figure 4.27 : Toxicity of the stem oils of Boesenbergia spp. on Artemia salina 76
Figure 4.28 : Toxicity of the rhizome oils of Boesenbergia spp. on Artemia salina 77
Figure 4.29 : Toxicity of the fruit oils of Boesenbergia spp. on Artemia salina 77
Figure 4.30 : Toxicity of the rhizome oils of Boesenbergia spp. on Nasutitermes sp. 79
Figure 4.31 : Toxicity of the fruit oils of Boesenbergia spp. on Nasutitermes sp. 79

LIST OF TABLES
Tables Page
Table 1.1 : Class of essential oils 2
Table 3.1 : Boesenbergia spp. used for the extraction of essential oil 18
Table 4.1 : Percentage yield and colour of essential oils from six species of 25
Boesenbergia
Table 4.2 : Kovats Indices for alkane Standard 26
Table 4.3 : Chemical Composition of the Essential Oils isolated from 29
Boesenbergia parva
Table 4.4 : Chemical Composition of the Essential Oils isolated from 37
Boesenbergia pulchella
Table 4.5 : Chemical Composition of the Essential Oils isolated from 41
Boesenbergia gracilipes
Table 4.6 : Chemical Composition of the Essential Oils isolated from 47
Boesenbergia burttiana
Table 4.7 : Chemical Composition of the Essential Oils isolated from 53
Boesenbergia grandis
Table 4.8 : Chemical Composition of the Essential Oils isolated from 60
Boesenbergia sp.
Table 4.9 : Similar compounds of essential oil in six species of Boesenbergia 68
Table 4.10 : Comparison of major compounds essential oils in different part of six 69
Boesenbergia spp.
Table 4.11 : Toxicity of essential oil from six species of Boesenbergia on Artemia 75
salina
Table 4.12 : Toxicity of essential oil of Boesenbergia spp. on Nasutitermes sp. 78
DECLARATION

No portion of the work referred to in this dissertation has been submitted in support of an
application for another degree of qualification of this or any other university or institution of
higher learning.

Zainah binti Adam


Programme of Resource Chemistry
Faculty of Science and Technology
Universiti Malaysia Sarawak

ACKNOWLEGMENT

I would like to express my special thanks to my supervisor Assoc. Prof. Dr Fasihuddin b.


Ahmad and my co-supervisor, Assoc. Prof. Dr Zaini B. Assim for giving me supports and
guidance in this research.
For laboratory assistants especially thanks to Mdm. Ros, Mr. Rajuna and colleagues of Faculty
of Resource Science and Technology UNIMAS, I also want to thank them for their supports
and cooperation in this study. My appreciation to all my lecturers and my course mates for
helping and supporting me while doing this research.
Studies on the Chemical Composition and Biological Activities of Essential Oils of
Boesenbergia spp.
Zainah Binti Adam
Programme of Resource Chemistry
Faculty of Resource Science and Technology
Universiti Malaysia Sarawak
ABSTRACT

Essential oils from six of Boesenbergia spp. were studied for their chemical composition and their biological activity.
Essential oils were extracted by hydrodistillation and analyzed using gas chromatography/flame ionization detector (GC/FID).
The percentage of essential oil obtained from the six species of Boesenbergia ranged from 0.17%to 1.50% with the highest
percentage was obtained from the rhizome of Boesenbergia gracilipes, while the B.pulchella gaves the lowest yield. The major
chemical compound in B. parva was methylisohexenyl ketone (30.87%) from the leaves oil; -copaene (13.56%) from the stem
oil; methionol (34.21%) from the rhizome oil and epoxy-2-undecenal (15.43%) from the fruit oils. The most abundant
compound found in B. pulchella was isogeraniol (80.00%) from the leaves oil; -cadinol (16.00%) from the stem oil and
eudesmol (44.62%) from the rhizome oil. B. gracilipes was rich with camphor (24.77%) in the leaves oil; perilla aldehyde
(22.19%) in the stem oil and lauryl alcohol (14.82%) in the rhizome oils. While1,8-cineole is the most abundant compounds in
the leaves (50.56%) , stem (24.39%) and rhizome (33.19%) of B. burttiana. B. grandis was rich in propionylpyrrole (9.18%)
from the leaves oil; cedrenol (19.58%) in the stem oil; cinnamic acid (15.73%) in the rhizome and -elemene (43.43%) in the
fruit oil. The major compound in Boesenbergia sp. was methyl laurate (24.88%) from leaves oil; cedrenol (19.58%) in the stem
oil and 1,8-cineole (11.06%), in the rhizome oil. Toxicity test of the essential oil of Boesenbergia spp. against brine shrimp,
Artemia salina shows that the essential oils from B. parva, B. pulchella, B. gracilipes and B. grandis showed strong toxicity
with LC50 ranged from 6.30 g/mL to 79.43 g/mL. The most active essential oils in this study were found to be the ones from
the leaves of B. parva. The essential oils from B. burttiana and Boesenbergia species showed the less toxicity with the
concentration more than 100 g/mL. Termicidal activity against Nasutitermes sp. showed that all the essential oil studied gave
LC50 in ranged of 0.10%-8.00%, except for the fruit oil of B. grandis with LC50 more than 10%. The rhizome oils of
B.burttiana exhibited the strongest activity with the LC50 value of 0.10%
Key words: Boesenbergia spp., hydrodistillation, gas chromatography/flame ionization detector, essential oils, toxicity test.

ABSTRAK
Komposisi minyak pati dari enam Boesenbergia spp. telah dikaji komposisi kimia dan aktiviti biologinya. Minyak pati telah
diekstrak dengan menggunakan kaedah penyulingan hidro dan seterusnya dianalisis menggunakan kromatografi gas/pengesan
ion nyalaan. Peratusan minyak pati yang diperolehi daripada enam spesies Boesenbergia adalah dalam julat 0.17% hingga
1.50% dengan peratusan tertinggi diperolehi daripada rizom B. gracilipes manakala B. pulchella memberikan nilai terendah.
Komponen utama dalam minyak B. parva ialah metilisoheksenil keton (30.87% ) pada daun, -kopaena (13.56%) pada batang,
metionol (34.21%) pada rizom dan epoksi-2-undicenal (15.43%) pada buah. B. pulchella kaya dengan isogeraniol (80.0%)
pada daun, -cadinol (15.99%) pada batang dan eudesmol (44.62%) pada rizom. Kamfor (24.77%) dalam daun, perila aldehid
(22.19%) dalam batang and and lauril alkohol (14.82%) dalam rizom merupakan komponen utama dalam minyak B.
gracilipes. Manakala 1,8-sineole hadir dalam kelimpahan tertinggi dalam semua bahagian daun (50.56%), batang (24.39%)
dan rizom (33.19%) B. burttiana. B. grandis kaya dengan propionylpyrrole (9.18%) dijumpai pada daun, dan cedrenol
(19.58%) pada batang, cinnamic acid (15.73% ) terdapat pada rizom dan -elemena (43.43%) dijumpai pada buah. Metal
laurat (24.88%) merupakan komponen utama dalam Boesenbergia spesis terdapat dalam daun, cedrenol (19.58%) pada
batang dan 1, 8-sineole (11.06%) pada rizom. Ujian ketoksikan minyak pati Boesenbergia spp. dari B. parva, B. pulchella, B.
gracilipes dan B. grandis keatas artemia salina menunjukkan aktiviti terkuat dengan julat LC50 dari 6.30 g/mL-79.43
g/mL. Minyak pati paling aktif adalah daripada daun B. parva, Minyak pati dari B. burttiana dan Boesenbergia spesis
menunjukkan ketoksikan terendah dengan kepekatan lebih daripada 100 g/mL . Ujian aktiviti terhadap Nasutitermes sp.
menunjukkan purata LC50 iaitu 0.10%-8.00%, kecuali pada minyak buah B. grandis dengan LC50 melebihi 10%. Minyak
Rizom B.burttiana memberikan aktiviti terkuat dengan nilai LC50 adalah 0.10%.
Kata kunci: Boesenbergia spp, penyulingan hidro, kromatografi gas/pengesan ion nyalaan, minyak pati, ujian ketoksikan.
CHAPTER 1

INTRODUCTION

1.1 INTRODUCTION

Essential oil is hydrophobic liquid containing volatile aroma compound from plants. Essential

oils are generally extracted by distillation, expression or solvent extraction. Essential oils is

secondary metabolism of plant and generally consist of complex mixtures of monoterpenes

(C10) and sesquiterpenes (C15), hydrocarbon and oxygenated material biogenically derived from

them. The boiling point for this monoterpenes is 140oC to 180oC while for the boiling points

sesquiterpenes is more than 180oC. The terpenes can exist as an open chain, monocyclic or

bicyclic and it is usually composed of one or more double bond and hydroxyl group (Parker,

1993). Other common constituents include phenyl propanoids from the shikimic acid pathway

and their bio-transformation products and other compounds from the metabolism of fatty acids

and amino acids (Ian et al., 2000). Chemically, essential oils are extremely complex mixtures

containing compounds at every major functional group class. Essential oils are commonly

grouped into six classes according to their chemical nature as depicted in Table 1.1 (Watson et

al., 1992).
Table 1.1: Class of essential oils

Components Examples
Hydrocarbons Limonene in lemon oil
Alcohols Borneol in rosemary oil
Ester Metyl salicylate in oil of wintergreen
Aldehyde Benzaldehyde in almond nut oil
Ketones Menthone in oil of peppermint
Lactones Coumarin from tonka beans

Other properties of essential oils with commercial potential include antimicrobial effects. The

inhibitions of 25 different bacteria using essential oil of marjoram have been reported (Ian et

al., 2000). Similar effect are noted for other volatile and essences derived from plant materials.

It was reported that short chain volatiles such as 5 to 8 carbon atom aldehyde and ketones

resulting from the distillation of vegetables oils had antimicrobial properties against bacteria

such as Staphylococcus aureus and Escherichia coli (Ian et al., 2000).

Zingiberaceae is a plant family which is rich in essential oil and this family is one of the largest

families of the plant kingdom. The Zingiberaceae family consists of about 1500 species and

about 1000 species are distributed throughout tropical Africa and Asia (Larsen et al., 1999).

Zingiberaceae plants such as Boesenbergia spp. are widely used in Asia as spice, fresh

vegetables and also as a source for traditional medicine (Larsen et al., 1999). Zingiber

officinale ginger for example, has been used long ago as spices and traditional medicine to treat

a variety of diseases (Larsen et al., 1999).


Boesenbergia spp. is a perennial herb of the Zingiberaceae family (Larsen, 1996). Boesenbergia

is a small forest plants with short, fleshy or slender rhizomes, one to a few leaves similar

appearance in vegetative characters and occurring in similar habitats. There are many species

of Boesenbergia for instance, B. plicata have yellow or red flowers while B. curtisii with white

or black leaf-sheaths as shown in Figure 1.1 (Vanijajiva et al., 2003; Boyce, 2006). The fresh

rhizome of Boesenbergia spp. are used in cooking as flavour and in folk medicine as

aphrodisiac, diuretic, antidysenteric, antidermatophytic and other uses (Saralamp et al., 1996).

Several studies have indicated some of the secondary metabolites from Boesenbergia spp. are

pharmaceutically active such as chalcone and cardamonin isolated from B. rotunda and showed

anti-HIV-1 protease inhibition (Cheenpracha et al., 2006).

a) b)

Figure 1.1: Example of Boesenbergia species found a) B. curtisii white leaf-sheaths,

b) B. plicata red flower (Vanijajiva et al., 2003; Boyce, 2006).


1.1 Objectives

The main purpose of this study is to extract and characterize the essential oils from several

Boesenbergia spp. The extraction of the essential oil was performed by hydrodistillation

method and the essential oil obtained was analyzed using Gas Chromatography/Flame

Ionization Detector (GC/FID). The biological activity of these essential oil especially

toxicity on brine shrimp, Artemia salina and termicidal activity on Nasutitermes sp. were

also be evaluated.
CHAPTER 2

LITERATURE REVIEW

2.1 Zingiberaceae Family

2.1.1 General

The Zingiberaceae is the largest families in the order Zingiberales which represent relatively

advance monocotyledonous plants are rhizomatous herbs found throughout tropical and

subtropical region with its main distribution in Asia (Sirirugsa, 1999; Kress et al., 2002). The

Zingiberaceae family consist at least 51 genera and 1500 species which are divided into four

tribes (Globbeae, Hedychieae, Alpinieae and Zingibereae). Generally, the Zingiberaceae is a

moderately-sized family; the species of this family are aromatic herbs with very prominent

thickened rhizomes. This family is often rich in essential oil, stored in typical secretory cells.

The leaves are arranged spirally or are distichously with a sheath around the stem (Ibrahim,

1999).

At least 20 or more ginger species have been cultivated for their use as spices, condiments,

flavours and vegetables (Larsen, 1999). Members in the Zingberaceae family such as Alpinia

and Kaempfaria are used to provide flavouring for cakes and pastries. It is also processed into

beverages for example ginger drink prepared from Zingiber officinale rhizomes regarded as

health drinks. The extracts of several species of Zingiber and Curcuma have shown for
antimicrobial activities (Ibrahim, 1999) and extracts of Alpinia, Costus and Zingiber showed

antibacterial and antioxidant activity (Habsah et al., 2000). Member of the Zingiberaceae

family are rich in essential oil such as borneol, champhor, 1,8-cineole, pinene , zingiberene,

camphene, phenylpropanoids, limonene, eugenol, geraniol and others (Larsen et al., 1999;

Ibrahim, 1999).

2.1.2 Medicinal Uses of Zingiberaceae Family

Zingiberaceae is important natural resources for many years as traditional remedies to treat a

variety of diseases and ailments such as rheumatism, high blood pressure, sinus and indigestion

(Vanijajiva et al., 2003). Some members in the Zingiberaceae family are effective in the

treatment of thrombosis, sea sickness and migraine (Sirirugsa, 1999; Vanijajiva et al., 2003). In

Malaysia, about 30 to 40 species of Zingiberaceae have long been used as traditional medicine

(Sirirugsa, 1999). For example Curcuma mangga, Curcuma aeruginosa and Zingiber

montanum are used in food preparations for women in confinement after birth (Larsen, 1999).

The members of Zingiberaceae family are used in Thai traditional medicine to treat allergy and

allergic-related diseases such as Kaempferia parviflora and Zingiber cassumunar (Twetrakul et

al., 2007). The rhizome of Kaempferia galangal is used externally to treat abdominal pain,

swelling and muscular rheumatism (Sirirugsa, 1999). Beside that, Zingiber officinale is used for

a large variety of illnesses, including travel sickness, respiratory and gastrointestinal disorders

(Ibrahim, 1999). The rhizome of Curcuma longa commonly used for treatment of

inflammatory and liver diseases. It is used also as a remedy for diarrhea, rheumatism, relieve
cough and to treat tuberculosis (Sirirugsa, 1999). The rhizome of Zingiber zerumbet is used to

relieve stomachache and is regarded as tonic, stimulant and depurative (Sirirugsa, 1999).

2.2 Boesenbergia spp.

2.2.1 General

The genus of Boesenbergia belongs to the Zingiberaceae family (Ngamriabsakul et al., 2005).

There are about 80 species in this genera and are distributed from India to South East Asia.

Thailand, as one of the two distribution centers apart from Borneo which have at least 25

species (Larsen, 2003). Many of Boesenbergia spp. is found in highly restricted localities and

many appear to be specific to particular habitat. Boesenbergia spp. such as B. pulchella and B.

oligosperma as shown in figure 2.1 can be found in the central part of Sarawak (Boyce, 2006).

Many Boesenbergia spp. such as B. pandurata are used as food and spices in various Thai food

dishes (Saralamp et al., 1996) and also in traditional functional foods such as tonic drinks to

maintain wellness (Nakahara et al., 2002). This species is also potential for inhibiting pathogens

in food systems (Thongson et al., 2005). In the consumer household product, B. pandurata

which consist of 1,8-cineole as the active ingredients can be used to give encapsulated materials

suitable for the manufacture of odour-absorbing and anti-bacterial product (Nakatsu et al.,

2000).
a) b)

Figure 2.1: Boesenbergia species that can be found in the central part of Sarawak

a) B. pulchella, b) B. oligosperma (Boyce, 2006).

2.2.2 Medicinal Uses of Boesenbergia spp.

Boesenbergia spp. has good potential to be used as medicine to treat various deseases. This

species have long been used in traditional medicine for the treatment of asaphthous ulcer, dry

mouth and stomach discomfort (Saralamp et al., 1996). Due to these properties, Boesenbergia

spp. has gained attention as important sources of active constituents for medicinal treatment. B.

rotunda is cultivated commercially and its rhizomes have been used for treatment of the cholic

disorder and as an aphrodisiac in folk medicine (Trakoontivakorn et al., 2001; Tuchinda et al.,

2002; Vanijajiva et al., 2003) and cullinary purposes. The rhizomes of this species showed

active HIV-1 protease inhibitory activity (Tewtrakul et al., 2003) and also exhibiting anti-

tumor, anti-mutagenic and anti-inflammatory activities (Murakami et al., 1994;

Trakoontivakorn et al., 2001; Tuchinda et al., 2002). B. rotunda is also used to treat dyspepsia
and peptic ulcer. This unique plant consumed by the Thai as food may control the infection by

Helicobacter pylori (gastric cancer causative agent) and explain the low incidence of gastric

cancer in the Thai population (Bhamarapravati et al., 2006).

B. pandurata has been widely used as a health-promoting herb and for the treatment of anti-

gastrointestinal disorders (Mahady et al., 2006). B. pandurata has been used for the treatment

of several diseases such as aphthous ulcer, dry mouth, stomach discomfort, leucorrhea and

dysentery (Saralamp et al., 1996). B. pandurata are potential anticancer plants and the

rhizomes are used for the treatment of dyspepsia (Narisa et al., 2007). Moreover, it has also

been used as self-medication by AIDS patients in Thailand (Cheenpracha et al., 2006).

2.2.3 Phytochemical Studies of Boesenbergia spp.

Various phytochemical and biological studies on Boesenbergia spp. have been performed and

interesting chemical compounds have been isolated and characterized.

2.2.3.1 Phenylpropanoids

The phenylpropanoids isolated from B. pandurata is methyl cinnamate (1) (Jantan et al., 2001).

OCH3

1
2.2.3.2 Monoterpenes

Monoterpene such as trans-pinocarveol (2) and (+)--pinene (3) were identified in the rhizome

oil of B. rotunda, B. pulchella and B. parva. Major compounds isolated from Boesenbergia

pandurata are 1,8-cineole (4), geraniol (5), (E)--ocimene (6), camphene (7), camphor (8)

(Jantan et al., 2001). The white rhizome of B. pandurata variety was found to contain (+)-

zeylenol (9), boesenboxide (10) (Pancharoen et al., 1984).

O
OH

2
4

OH

5 7
6
OH
OBz
OH
O

OH

OBz
8
9
2.2.3.3 Sesquiterpenes

Sesquiterpene such as -selinene (11), -elemene (12), -elemene (13), -muurolene (14),

spathulenol (15), caryophyllene alcohol (16), and kaur-16-ene (17) was the main compounds

isolated from the rhizome and leaf oils of B. stenophylla (Ahmad et al., 2003).

11 12 13

H
H
H
OH

H H

H

16
15
OH

OH
17
2.2.3.4 Chalcones

Chalcones derivatives such as helichrysetin (18), uvangoletin (19), 2,4,6,-

trihydroxydihydrochalcone (20), panduratin A (21) and (-)- hydroxypanduratin A (22) have

been isolated from the rhizomes of B. pandurata (Trakoontivakorn et al., 2001; Tuchinda et al.,

2002). Chalcones such as cardamonin (23) were isolated from the yellow rhizomes of B.

pandurata (Trakoontivakorn et al., 2001).

OH

HO OMe
HO OMe

OH O
OH O

19
18

OH O
HO OH

OH
CH3O

OH
O

20
21

HO
OMe

O
OH

23
2.2.3.5 Flavanoids

Flavanoids such as 5-hydroxy-7-methoxyflavanone (24) and pinostrobin (25) was isolated from

the yellow rhizomes of B. pandurata (Trakoontivakorn et al., 2001). Pinocembrin (26) and 5,7-

dihydroxyflavone (27) have been isolated from the red rhizomes variety of B. pandurata

(Trakoontivakorn et al., 2001; Tuchinda et al., 2002).

OH O

CH3O
O

O
CH3O

OH O
24 25

OH
O

O
HO

27
2.2.4 Biological activities of Boesenbergia spp.

Rhizomes extract from several Boesenbergia spp. such as B. curtisii and B. plicata exhibited

antitumor and strong antimutagenic activity (Trakoontivakorn et al., 2001), while B. pandurata

was regarded as excellent candidates for the development of a remedy for fungal infections in

AIDS patients (Phongphaichit et al., 2005). Several studies have shown that some compounds,

such as flavanoids and chalcones are pharmaceutically active. Chalcone such as cardamonin

(23) isolated from B. rotunda was reported to exhibit appreciable anti-HIV-1 protease inhibition

(Kiat et al., 2006).

The cyclohexenyl chalcone derivatives of B. rotunda have shown various biological activities

such as anti-inflammatory (Tuchinda et al., 2002), strongly antimutagenic (Trakoontivakorn et

al., 2001) and Dengue 2 virus protease inhibiting (Tan et al., 2006). Geraniol (5) which is

acyclic monoterpenoids isolated from B. pandurata showed strong inhibitory effect on tyrosine

activity (Nakatsu et al., 2001) while 2,6-dihydroxy-4-methoxychalcone showed neuroprotective

effects (Shindo et al., 2006). Methanolic extract of B. rotunda partitioned in chloroform showed

anti-dermatophytic activity against Epidermophyton floccosum, Microsporum gypseum and

Trichophyton mentagophyte (Bhamarapravati et al., 2000). Sakaengarm et al (2003) also

reported the isolation of dihydroguaiaretic acid from the crude extract of B. rotunda which

antifungal activity against Collectotrichum gloeosporioides (Bamarapravati et al., 2006).


Compounds such as 5-hydroxy-7-methoxyflavanone (24), 5,7-dihydroxyflavanone, 2,6-

dihydroxy-4-methoxychalcone, 2,4-dihydroxy-6-methoxychalcone and 4-hydroxypanduratin

isolated from the rhizome of B. pandurata was found to possess potent antioxidant activity and

strong antimutagens (Cheenpracha et al., 2006). Panduratin A (21) compound exhibited strong

antibacterial activity against Porphyromonas gingivalis a type of bacteria causing periodontitis

(Park et al., 2005), active against HIV-1 PR (Cheenpracha et al., 2006) and posses significant

topical anti-inflammatory activity in the TPA-induced ear edema assay in rats (Tuchinda et al.,

2002). Compounds isolated from the fresh rhizomes of B. pandurata such as cardamonin (23),

pinocembrin (26), pinostrobin (25), 4-hydroxypanduratin A and panduratin A (21) are strong

antimutagens (Trakoontivakorn et al., 2001). Methanolic extract of the rhizomes of B.

pandurata showed a potent antimutagenic effect against heterocyclic amines Trp-P-1 in the

Ames test (Nakahara et al., 2002).