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UNIVERSITI MALAYSIA SABAH

Malaysia Sabah (UMS) Research funding in the form of IRPA 06-02-02-001BTK-ER-015(1) (UMS 95500-37 awarded to Prof Dr Mashitah M Yusoff) is also gratefully acknowledged Both of these funds have enabled me to complete this study without financial difficulty A very special thanks to the School of Food science & nutrition

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BIOASSAY-GUIDED ISOLATION OF FREE

RADICAL SCAVENGING AND

ANTIOXIDATIVE FLAVONOID FROM

ZINGIBER OTTENSII (ZINGIBERACEAE)

NARANSA LIMPOT

PERPUSTAK4AN

UNIVERSITI MALAYSIA SP.I?-!l4

THESIS SUBMITTED IN FULFILLMENT OF

THE REQUIREMENT FOR THE DEGREE

MASTER OF SCIENCE IN NATURAL

PRODUCT CHEMISTRY

INSTITUTE FOR TROPICAL BIOLOGY AND

CONSERVATION

UNIVERSITI MALAYSIA SABAH

2006
-:UMS

SA R , \\ UNIVERSITI MALAYSIA SABAH

Judul:

Ijazah:

UNIVERSITI MALAYSIA SABAH

BORANG PENGESAHAN STATUS TESISo

BIOASSAY-GUIDED ISOLATION OF FREE RADICAL

SCAVENGING AND ANTIOXIDATIVE FLAVONOID FROM

ZINGIBER OrrENSII(Z1NGIBERACEAE)

SARlANA SAINS (KIMIA HASILAN SEMULAlADI)

Sessi Pengajian: 2003-2006

Saya Naransa Umpot mengaku membenarkan tesis sarjana disimpan di perpustakaan Universiti Malaysia Sabah dengan syarat-syarat kegunaan seperti berikut:

1. Tesis adalah hak milik Universiti Malaysia Sabah

2. Perpustakaan Universiti Malaysia Sabah dibenarkan membuat salinan untuk

tujuan pengajian sahaja

3. Perpustakaan dibenarkan membuat salinan tesis ini sebagai bahan pertukaran

antara institusi pengajian tinggi. 4. ndak terhad.

Alamat tetap:

Peti surat 308,

89058,

Kudat,

Sabah, Malaysia.

Tarikh: 22 Jun 2006

Pthr "" ...

Disahkan oleh

UNIVERSITI M

(Penyelia:P Dr Mashitah MOYUsoff) CATATAN: Tesis@ dimaksudkan sebagai tesis Doktor Falsafah atau Sarjana secara penyelidikan atau disertasi bagi pengajian secara kerja khusus dan penyelidikan atau laporan Projek Sarjana Muda UMS

UNIVERSITI MALAYSIA SABAH

11

DECLARATION

The materials in this thesis are original except for quotation, excerpts, summaries and references, which have been duly acknowledged.

NARANSA UMPOT

PS03-00S-012

2nd JUNE 2006

UMS

UNIVERSITI MALAYSIA SABAH

III

ACKNOWLEDGEMENT

Firstly, I thank my supervisor Prof. Dr. Mashitah M. Yusoff for her dedication, fruitful suggestions, constructive comments and excellent supervision throughout this study.

Next, I would like to thank to the Ministry

of Science, Technology and Innovation Malaysia for the research grant awarded to me through Universiti Malaysia Sabah (UMS). Research funding in the form of IRPA 06-02-02-001BTK-ER-

015(1)

(UMS 95500-37 awarded to Prof. Dr. Mashitah M. Yusoff) is also gratefully acknowledged. Both of these funds have enabled me to complete this study without financial difficulty. A very special thanks to the School of Food science & nutrition (UMS) for allowing me use of instruments. I am grateful to my family and friends for their continued support through difficult times during this undertaking. UMS

UNIVERSITI MALAYSIA SABAH

ABSTRAK

PEMENCILAN MELALUI BIOCERAKINAN UNTUK PELEKATAN

RADIKAL BEBAS AND ANTIOKSIDAN FLAVONOID DARIPADA

ZINGIBER OTTENSII(ZINGIBERACEAE)

Biocerakinan terhadap fraksi mengunakan 2,2-diphenyl-l picrylhydrazyl telah dijalankan terhadap rizom dan daun Zingiber ottensii untuk pemencilan and pengenalpastian kompoun yang menunjukkan aktiviti bioaktif secara pelekatan radikal bebas dan antioksidan yang hadir dalam ekstrak meta no!. kompoun aktif yang dipencilkan dikenalpasti menggunakan kaedah spektroskopi sebagai kuersetin-3-D-ramnosilglucosida. Kandungan keseluruhan kompoun aktif setara dengan kuersetin juga telah dikira secara kuantitatif dan didapati bahawa kandungan kuersetin dalam rizom lebih banyak berbanding daun.

Rizom juga didapati mengadungi 60% gula

berdasarkan berat keringnya dan dikenalpasti dengan menggunakan Reagen Bial's sebagai heksos dan pentos. Penemuan Inl menyumbang kepada kajian pertama kalinya terhadap kelompok halia kerana ulasan perpustakaan terhadapnya belum wujud. Ujian autoksidasi f3-carotene juga telah dijalankan untuk mengkaji kebolehan kompoun yang dipencilkan untuk menghalang oksidasi lipid. Didapati bahawa kompoun ini adalah sama aktif berbanding antioksidan sintetik,

BHT, dan lebih aktif berbanding dengan aglaikon

kuersetin. Walaupun kuersetin telah diketahui sebagai pelekat radikal dan penghalang oksidasi lipid yang sangat baik, inilah kali pertama kompoun ini dikesan dalam Z ottensii. IV UMS

UNIVERSITI MALAYSIA SABAH

ABSTRACT

BIOASSAY-GUIDED ISOLA TTON OF FREE RADICAL

SCAVENGING AND ANTTOXIDA TIVE FLA VONOID FROM

ZINGIBER OTTENSII (ZINGIBERACEAE)

Bioassay-guided fractionation by 2, 2-diphenyl-l-picrylhydrazyl has been conducted for rhizomes and leaves of Zingiber ottensii to isolate and elucidate the bioactive compound that possess free radical scavenging and antioxidative activities present in the methanol extract. The isolated active compound was identified by means of spectroscopic methods as quercetin-3-0-rhamnosylglucoside. The total content of the active compound in equivalence to quercetin was also quantified and found that the quercetin content was more in rhizomes compared to the leaves. The rhizomes were also found to contain sugars which contributed

60% of the dry weight and was

identified by using Bial's Reagent as hexoses and pentoses. This finding can contribute towards the novel study in gingers since there is a void in the present literature on the subject.

The autoxidation of

fJ-carotene was also tested in effort to investigate the ability of the isolated compound toward inhibition of lipid peroxidation. It was found that this compound was as active as the synthetic antioxidant, BHT, and was more active than the corresponding quercetin aglycone. Eventhough, quercetin has been known as an excellent radical scavenger and inhibit lipid peroxidation, this is the first time this compound was detected in

Z. ottensii.

v UMS

UNIVERSITI MALAYSIA SABAH

VI

ABBREVIATIONS

Abs Absorption

ACCase

Acetyl Co-A carboxyligase

2, 2'-Azinobis-(3-ethylbenzthiazoline-6-sulfonic) acid

BHA

Butylated Hydroxyanisol

BHT

Butylated Hydroxytoluene

CHS

Chalcone synthase

DNA

Deoxyribonucleic acid

DPPH-

2, 2-diphenyl-l-picrylhydrazyl

EDso Dose of sample required to effect 50% of organism under study

HCI Hydrochloric acid

HPLC

High Performance Liquid Chromatography

IC 50
Concentration of sample required to inhibit 50% of oxidation

LC-MS Liquid Chromatography-Mass Spectrometry

MeOH Methanol

PG Propyl gallate

SD Standard deviation

TBQH

Tert-butyl hydroquinone

TLC Thin Layer Chromatography

UV Ultra Violet

UMS

UNIVERSITI MALAYSIA SABAH

Vll

CONTENTS

Page TITLE

DECLARATION

ii

ACKNOWLEDGMENT iii

ABSTRAK iv

ABSTRACT v

ABBREVIATIONS vi

CONTENTS vii

LIST OF TABLES xi

LIST OF FIGURES xii

LIST OF APPENDIXES xiii

CHAPTER 1 INTRODUCTION 1

1.1 Background 1

1.2 Research justification 3

1.3 Research objectives 3

CHAPTER 2 LITERATURE REVIEW 4

2.1 Background 4

2.2 Zingiberaceae as food and remedies 5

2.2.1 Previous research on Z ottensiiand Z zerumbet chemical constituents 8

2.3 The role of antioxidant in human health 11

2.3.1 Nature of free radical species 12

2.3.2 Chemical antioxidant 13

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UNIVERSITI MALAYSIA SABAH

VllI

2.4 The chemistry of f1avonoids 14

2.4.1 Flavonoids structure and major f1avonoids classes 14

2.4.2 Biosynthesis of flavonoids 16

2.4.3 Bioactivity of f1avonoids 17

2.4.4 Structure-activity relationship of free radical and

anti oxidative of flavonoids 18

CHAPTER 3 METHODOLOGY 20

3.1 Plant collection 20

3.2 Plant physical properties 20

3.2.1 Moisture content 20

3.2.2 Plant material and extraction 20

3.2.3 'Bial's Reagent'-Screening of sugar content 21

3.3 Determination of flavonoid 21

3.3.1 Fractionation for bioassay-guided isolation 21

3.3.2 Fractionation of active fractions 22

3.4 Identification and determination of flavonoid in bioactive

subfractions by High Performance Liquid

Chromatography (HPLC) 22

3.4.1 Identification and determination of active subtractions using

external standard 23

3.4.2 Identification and determination of active subfractions using

internal standard 23

3.5 Structure identification in active subtractions 23

3.5.1 Determination of structure by UV-Visible spectrophotometer 24

3.5.2 Structure corroboration by Liquid Chromatography-Mass Spectrometry 24

UMS

UNIVERSITI MALAYSIA SABAH

IX

3.6 Determination of total flavonoid content in active subfractions 24

3.7 Bioassay 25

3.7.1 DPPH. (2, 2-Diphenyl-1-picrylhydrazyl) assay on TLC plate 25

3.7.2 Free radical scavenging activity assay for bioassay-guided isolation 25

3.7.3 Preparation of sample and DPPH. for bioassay-guided isolation 26

3.7.4 DPPH. test of the subfractions from active fractions 26

3.8 Autoxidation of j3-carotene 27

CHAPTER 4 RESULTS 28

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