UNIVERSITI PUTRA MALAYSIA

PHYTOCHEMICAL STUDIES OF MESUA CORNERI (LINN.) AND GARCINIA MANGOSTANA (LINN.) AND THEIR BIOLOGICAL

ACTIVITIES

SHEIKH AHMAD IZADDIN SHEIKH MOHD GHAZALI.

FS 2006 6

PHYTOCHEMICAL STUDIES OF MESUA CORXERI (LINN.) AND GARCZNZA MANGOSTANA (LINN.) AND THEIR BIOLOGICAL ACTIVITIES

BY

SHEIKH AHMAD IZADDIN SHEIKH MOHD GHAZALI

Thesis Submitted to the School of Graduate Studies, Universiti Putra Malaysia, in FulfiIment of the Requirement for the Degree of Master of Science

January 2006

Abstract of thesis presented to the Senate of Universiti Putra Malaysia in fulfilment of the requirement for the degree of Master of Science

PHYTOCHEMICAL STUDIES OF MESUA CORNERI (LINN) AND GARCINIA MANGOSTANA (LINN) AND THEIR BIOLOGICAL

ACTIVITIES

By

SHEIKH AHMAD IZADDIN

January 2006

Chairman : Associate Professor Gwendoline Ee Cheng Lian, PhD

Faculty : Science

Roots of Garcinia mangostana L. and the stem bark of Mesua corneri L. were

chemically investigated. Detail phytochemical studies on the roots of Garcinia

mangostana L. and the stem bark of Mesua corneri L. have resulted in the isolation of

eleven compounds. The structures of these compounds were elucidated using

spectroscopic experiments namely NMR, IR, UV and MS.

The root bark of Garcinia mangostana L. furnished six xanthones, a-mangostin, P-

mangostin, y-mangostin, garcinone-D, mangostanol and gartanin. Up to now, research

has only been carried out on the fruit hull and the stem bark of this plant. There have

been no studies yet on the root bark of Garcinia wangostana L. Meanwhile,

investigations on stem bark of Mesua corneri L gave three triterpenoid, stigmasterol,

fridelin, friedelan-1,3-dione and two xanthones, rubraxanthone and Inophyilin B. So far,

there has been no reports at all on this plant.

The crude hexane and chloroform extracts of Mesua corneri L. stem bark were active

against HL-60 cell line with 1Cj0 values of less than 30 pg/ml. The crude hexane and

chloroform extracts of Garcinia mangostana L. root bark were found to be active against

CEM-SS cells line with ICsO values of less than 30 pglml. Meanwhile, the y-mangostin

gave a significant activity with an ICjO value of 4.7 pglml. This is a new activity for this

plant.

The antimicrobial assay was carried out towards four pathogenic bacteria, Methicillin

Resistant Staphylococcus awes, Pseudornonas aeruginosa, Salmonella typhiinurium and

Bacillus subtilis. Most of the crude extracts tested against these microbes gave only

moderate or weak activities.

The larvicidal tests performed against the larvae of Aedes aegypti. The crude hexane and

chloroform extracts of Garcinia mangostana L. showed a strong activity against the

larvae with LC50 values of less than 100 pglml. The pure compounds a-mangostin and y-

mangostin gave good activities with LCso value of 18.4 and 32.4 pglml respectively .The

crude hexane and choloroform extracts of Mesua corneri L. showed a good activities

against the larvae and gave LCSo values of less than 100 pgjrnl. Rubraxanthone showed a

strong activity against the larvae with a LCso value of 18.4 pglml. These activities have

not been reported before and this is a new finding.

The antifungal activity testing of the plant extracts were carried out against the fungi

Candida albican, Aspergillus ochraceaus, Sacchoromyces cerevisiae and Candida

lypolytica. No activity was observed for all the crude extracts.

Abstrak tesis yang dikemukakan kepada Senat Universiti Putra Malaysia sebagai memenuhi keperluan untuk ijazah Master Sains

KAJIAN FITOKIMIA DAN AKTIVITI BIOLOGI DARIPADA MESUA CONERI (LINN .) DAN CARCINIA MANCOSTANA (LINN.)

Oleh

SHEIKH AHMAD IZADDIN

Januari 2006

Pengerusi : Profesor Madya Gwendoline Ee Cheng Lian, PhD

Fakulti : Sains

Akar dari pokok Garcinia mangostana dan kulit batang dari pokok Mesua corneri L.

telah dikaji secara kimia. Kajian fitokimia terperinci ke atas bahagian akar Garcinia

mangostana dan bahagian kulit batang pada tumbuhan Mesua corneri L telah

menghasilkan sebelas sebatian. Struktur sebatian-sebatian ini ditentukan dengan

mengunakan eksperimen spekstroskopi seperti NMR, IR, UV dan MS.

Akar dari Garcinia mangostana L. telah menghasilkan enam xanthone iaitu, a-

mangostin, P-mangostin, y-mangostin, garcinone-D, mangostanol dan gartanin.

Sehingga sekarang, kebanyakkan penyelidik hanya tertumpu kepada bahagian kulit buah

dan kulit batang pada tumbuhan ini dan tiada kajian mengenai bahagian akar pada

tumbuhan ini. Manakala, kajian terperinci terhadap kulit batang pokok. Mesua corneri

Ltelah menghasilkan tiga triterpenoid, stigmasterol, fridelin, friedelan-1,3-dione dan dua

xanthone, rubraxanthone dan inophyllin B-Tiada lagi laporan mengenai pokok ini

diterbitkan.

Ekstrak mentah heksana dan kloroform Garcinia rnoangostana L. dianggap sebagai aktif

ke atas sel HL-60 dengan nilai ICjo kurang daripada 30 pglml. Ekstrak mentah heksana

dan kloroform Meusa corneri L. juga dianggap aktif ke atas sel CEM-SS dengan nilai

ICS0 kurang daripada 30 pglml. Sebatian tulen iaitu y-mangostin telah menunjukkan

keaktifan yang baik pada dengan ICso adalah 4.7 pg/ml. Ini adalah penemuan bagi

sebatian tulen ini.

Ujian anti-mikrobial dijalankan dengan menggunakan bakteria-bakteria jenis Methicillin

Resistant Staphylococczrs aures, Psetrdornonas aeruginosa, Salmonella typhimzrriurn dan

Bacillus subtilis. Kebanyakan ekstrak yang diuji menunjukkan keaktifan yang sederhana

atau rendah terhadap bakteria-bakteria.

Ujian larva telah dijalankan dengan menggunakan larva jenis Aedes aeaypti. Kesemua

ekstrak mentah Garcinia rnangostana mempunyai aktiviti yang kuat terhadap terhadap

larva dengan nilai kurang 100 pg/ml.Sebatian tulen iaitu a-mangostin dan y-

mangostin memberkan aktiviti yang kuat dengan LCso adalah 18.4pg/ml dan 32.4 pg/ml.

Ekstrak mentah Mesua coneri menunjukkan aktiviti yang baik terhadap larva dengan

memberikan nilai LC kurang daripada 100 pg/ml. Rubraxanthone menunjukkan

aktiviti yang kuat terhadap larva dengan nilai LCsO 18.4 pg/ml. Aktiviti ini belum pernah

lagi dilaporkan sebelumi ini dan ini adalah penemuan baru.

vii

Aktiviti anti-fungal ekstrak tumbuhan telah dijalankan ke atas Candida albican,

Aspergillus ochraceaus, Sacchoromyces cerevisiae dan Candida lypolytica. Tiada

aktiviti diperhatikan ke atas semua ektrak mentdh.

ACKNOWLEDGEMENTS

All praises to Allah, Lord of the universe. Only with His grace and mercy that this

thesis can be completed.

I wish to express my sincere thanks to my supervisor Assoc. Prof. Dr. Gwendoline

Ee Cheng Lian for her invaluable guidance, support and continuous encouragement

throughout the course of this project.

My gratitude also goes to my supervisory committee Prof. Dr. Mawardi Rahmani for

his support and comments. Financial support from Ma!aysian Gevernmer?t under

then IRPA programme and UPM fundamental research are gratefully acknowledged.

My special thanks to my colleagues Chan Kiang, Sooi Kim, Audrey, to my best

friends Mohd. Shamsul Ezzad, Shaari Daud and to my special friend Nur Syuriati for

sharing the stress, laughter and useful advice during this project. Special thanks are

extended to staff of the Chemistry Department of UPM especially Mr. Johadi, Mr.

Zainal Abidin Kassim, and Mrs Rusnani Aminuddin for helping me to obtain NMR,

CC-MS and IR data.

Last but not least, I wish to especially acknowledge my beloved mum (Siti Khadijah)

and dad (Sheikh Mohd. Ghazali), and to my sisters (Siti Nur Adawiyah and Siti Nur

Ahdiah) and brother (Sheikh Ahmad Firdaus) for their patience, love and

understanding.

I certify that an Examination Committee met on 23 Januari 2006 to conduct the final examination of Sheikh Ahmad Izaddin bin Sheikh Mohd. Ghazali on his Master of Science thesis entitled "Phytochemical Studies of Mesua corneri (Linn.) and Garcinia mangostana (Linn.) and Their Biological Activities" in accordance with Universiti Pertanian Malaysia (Higher Degree) Act 1980 and Universiti Pertanian Malaysia (Higher Degree) Regulations 1981. The Committee recommends that the candidate be awarded the relevant degree. Members of the Examination Committee are as follows:

ABDUL HALIM ABDULLAH, PhD Professor Faculty of Graduate Studies Universiti Putra Malaysia (Chairman)

TAUFIQ-YAP YUN HIN, PhD Professor Faculty of Graduate Studies Universiti Putra Malaysia (Internal Examiner)

MOHD ASPOLLAH SUKARI, PhD Professor Faculty of Graduate Studies Universiti Putra Malaysia (Internal Examiner)

IBRAHIM JANTAN, PhD Professor Faculty of Graduate Studies Universiti Putra Malaysia (External Examiner)

School of ~ r i d u a t e Studies Universiti Putra Malaysia

This thesis submitted to the Senate of Universiti Putra Malaysia has been accepted as fulfilment of the requirement for the degree of blaster of Science. The members of the Supervisory Committee are as follows:

GWENDOLINE EE CHENG LIAN, PhD Associate Professor Faculty of Science Universiti Putra Malaysia (Member)

MAWARDI BIN RAHMANI, PhD Professor Faculty of Science Universiti Putra Malaysia (Member)

AINI I D E ~ S , PhD Professor1 Dean School of Graduate Studies Universiti Putra Malaysia

Date: 13 APR 2006

DECLARATION

I hereby declare that the thesis is based on my original work except for quotations and citations which have been duly acknowledged. I also declare that it has not been previously or concurrently submitted for any other degree at UPM or other institutions.

SHEIKH AHMAD I Z A ~ D I N

xii

TABLE OF CONTENTS

ABSTRACT ABSTRAK ACKNOWLEDGEMENTS APPROVAL DECLARATION LIST OF TABLES LIST OF FIGURES LIST OF ABBREVIATIONS

CHAPTER

INTRODUCTION 1.1 General Introduction 1.2 Objectives of Study

LITERATURE REVIEW 2.1 Botany of Plants Studied

2.1.1 The family Guttiferae 2.1 -2 The genus Garcinia 2.1.3 The genus Mesua 2.1.4 The species Garcinia rnangostana L. 2.1.5 The species Mesua corneri L.

2.2 Chemistry of Garcinia species 2.3 Previous Work on xanthones in Garcinia species 2.4 Previous Work on flavonoids in Garcinia species 2.5 Previdus Work on benzophenone in Garcinia species 2.6 Previous Work on terpenes in Garcinia species 2.7 Previous Work on bioassay of Garcinia species 2.8 Chemistry of Mesua species 2.9 Previous Work on Mesua corneri 2.10 Previous Work on Bioassay of Mesua species 2.1 1 Biosynthesis of xanthones

EXPERIMENTAL 3.1 Plant Material 3.2 Instruments

3.2.1 Infrared Spectroscopy (IR) 3.2.2 Mass Spectra (MS) 3.2.3 Melting Point 3.2.4 Nuclear Magnetic Resonance (NMR) 3.2.5 Ultra Violet (UV)

Page . . 11

v . . . Vlll

ix xi xv

xvii xxi i

3.3 Chromatographic Methods 3.3.1 Column Chromatography 3.3.2 Thin Layer Chromatography (TLC) 3.3.3 Preparative Layer Chromatography

3.4 Dyeing Reagents for TLC 3.4.1 Vanillin-Sulfuric Acid solution 3.4.2 Iron (111) Chloride solution

3.5 Extraction and isolation of compounds from Garcinia mangostana L. and Mesua corneri L. 3.5.1 Garcinia mangostana L.

3.5.1.1 Isolation of a-mangostin (65) 3.5.1 -2 Isolation of P-mangostin (77) 3.5.1.3 Isolation of y-mangostin (89) 3.5.1.4 Isolation of garcinone-D (93) 3.5.1.5 Isolation of mangostanol (1 00) 3.5.1.6 Isolation of gartanin (101)

3.5.2 Mesua corneri L. 3.5.2.1 Isolation of Stigmasterol (1 23) 3.5.2.2 Isolation of Friedelin (124) 3.5.2.3 Isolation of Friedelan-1,3-dione (125 ) 3.5.2.4 Isolation of rubraxanthone (1 56) 3.5.2.5 Isolation of inophyllin B (163)

3.6 Cytotoxic Assay 3.7 Antimicrobial Activity 3.8 Larvicidal Assay 3.9 Antifungal Activity

RESULTS AND DISCUSSION 4.1 Isolation of Chemical Constituents from Garcinia

mangostana L. 4.1.1 Characterization of a-mangostin (65) 4.1.2 Characterization of P-mangostin (77) 4.1.3 Characterization of y-mangostin (89) 4.1.4 Characterization of Garcinone D (93) 4.1.5 Characterization of Gartanin (101) 4.1.6 Characterization of Mangostanol (1 00)

4.2 Isolation of Chemical Constituents from Mesua corneri L. 4.2.1 Characterization of Stigmasterol (1 23) 4.2.2 Characterization of Friedelin (1 24) 4.2.3 Characterization of Friedelan-l,3-dione (125) 4.2.4 Characterization of Rubraxanthone (1 56) 4.2.5 Characterization of Inophyllin B (163)

4.3 Bioassay Results 4.3.1 Cytotoxic Activity 4.3.2 Antimicrobial Activity 4.3.3 Larvicidal Activity 4.3.4 Antifungal Activity

xiv

CONCLUSIONS

BIBLIOGRAPHY APPENDICES BIODATA OP THE AUTHOR

LIST OF TABLES

Table Page

72 4.1 'H NMR (400 MHz, CDC13) and 13c NMR (100 MHz, CDC13). Assignments of a-mangostin (65)

'H NMR (400 MHz, CDC13) and I3c NMR (100 MHz, CDCI3), COSY and HMBC. Assignments of a-mangostin (65)

'H NMR (400 MHz, CDC13) and 13c NMR (100 MHz, CDCI3), COSY and HMBC. Assignments of a-mangostin (65)

'H NMR (400 MHz, CDC13) and 13c NMR (100 MHz, CDC13), COSY and HMBC. Assignments of P-mangostin (77)

'H NMR (400 MHz, Me2CO-d6) and 13c NMR (100 MHz, Me2CO-d6). Assignments of y-mangostin (89)

'H NMR (400 MHz, MezCO-d6), 13C NMR (100 MHz, MezCO-d6). 108 Assignments of garcinone D (93)

'H NMR (400 MHz, Me2CO-d6) and 13c NMR, COSY and HMBC (I00 109 MHz, Me2CO-d6). Assignments of garcinone D (93)

'H NMR (400 MHz, Me2CO-dc), I3c NMR (100 MHz, Me2CO-d6), 121 COSY, and HMBC. Assignments of gartanin (101)

1 H NMR (400 MHz, CD3OD), I3c NMR (100 MHz, CD30D). 132 Assignments of mangostanol (1 00)

'H NMR (400 MHz, CD30D) and I3c NMR (100 MH CD30D), COSY 133 and HMBC. Assignments of mangostanol (100)

'H NMR (400 MHz, CDCI3), 13C NMR (100 MHz, CDCI3), COSY, and 146 HMBC. Assignments of stigmasterol (123)

'H NMR (400 MHz, CDC13), I3c NMR (100 MHz, CD30D), COSY and 153 HMBC. Assignments of friedelin (124)

'H NMR (500 MHz, CDCI3), l 3 C NMR (125.65 MHz, CDCI3). 162 Assignments of Friedelan-1,3-dione (1 25)

'H NMR (400 MHz, Me2CO) and I3c NMR (100 MHz, Me2CO). 186 Assignments of rubraxanthone ( 156)

xvi

'H NMR (400 MHz, Me2CO) and 13c NMR (100 MHz, MeKO), COSY 187 and HMBC. Assignments of rubraxanthone (1 56)

'H NMR (400 MHz, CDC13) and 13c NMR (100 MHz, CDCI3). 199 Assignments of Inophyllin B (1 63)

'H NMR (400 MHz, CDC13) and 13c NMR (100 MHz, CDC13), COSY 200 and HMBC. Assignments of Inophyllin B (163)

Cytotoxic Activity of plant extracts and pure compound against HL-60 210 Cell Line (Promyelocytic Leukemia) and CEM- SS Cell Line (T- lymphoblastic Leukemia)

Antimicrobial activity of crude extracts of Mesua corneri and Garcinia 2 14 mangostana

Larvicidal activity of crude extracts and pure compounds against the 215 larvae of Aedes aegypti

xvii

LIST OF FIGURES

Figures

Skeleton of flavanoids

Biosynthesis of xanthones

Compounds obtained from roots of Garcinia rnangostana

EIMS spectrum of a-mangostin (65)

IR spectrum of a-mangostin (65)

'H NMR spectrum of a-mangostin (65) (400 MHz, CD3OD)

I3c NMR spectrum of a-mangostin (65) (100 MHz, CD3OD)

'H-'H COSY spectrum of a-mangostin (65) (400 MHz, CD30D)

'H-'H COSY spectrum of a-mangostin (65) (400 MHz, CD3OD) (expanded)

HSQC spectrum of a-mangostin (65)

HMBC spectrum of a-mangostin (65)

EIMS spectrum of P-mangostin (77)

IR spectrum of P-mangostin (77)

1 H NMR spectrum of P-mangostin (77) (400 MHz, CD30D)

1 H-'H COSY spectrum of P-mangostin (77) (400 MHz, CD30D)

I3c NMR spectrum of P-mangostin (77) (1 00 MHz, CD30D)

DEPT spectrum of P-mangostin (77) (1 00 MHz, CD3OD)

HSQC spectrum of P-mangostin (77)

HMBC spectrum of P-mangostin (77)

EIMS spectrum of y-mangostin (89)

IR spectrum of y-mangostin (89)

Page

2 1

39

69

74

75

76

xviii

1 H NMR spectrum of y-mangostin (89) (400 MHz, CD30D)

1 H-'H COSY spectrum of y-mangostin (89) (400 MHz, CD30D)

I3c NMR spectrum of y-mangostin (89) (100 MHz, CD30D)

HSQC spectrum of y-mangostin (89)

DEPT spectrum of y-mangostin (89) (100 MHz, CD30D)

HMBC spectrum of y-mangostin (89)

HMBC spectrum of y-mangostin (89) (expanded)

EIMS spectrum of garcinone D (93)

IR spectrum of garcinone D (93)

'H NMR spectrum of garcinone D (93) (400 MHz, Me2CO-ds)

'H NMR spectrum of garcinone D (93) (400 MHz, MezCO-d6) 113 (expanded)

1 H-'H COSY NMR spectrum of garcinone D (93) (400 MHz, Me2CO-d6)

I3c spectrum of garcinone D (93) ( 1 00 MHz, Me2CO-d6)

HSQC spectrum of garcinone D (93)

DEPT spectrum of garcinone D (93) (1 00 MHz, MezCO-d6)

HMBC spectrum of garcinone D (93)

EIMS spectrum of gartanin (1 01)

IR spectrum of gartanin (101)

'H NMR spectrum of gartanin (101) (400 MHz, Me2CO-d6)

13 C NMR spectrum of gartanin (1 0 1) (1 00 MHz, Me2CO-d6)

'H-'H COSY spectrum of gartanin (I 01) (400 MHz, Me2CO-d6)

HSQC spectrum of gartanin (1 01)

HMBC spectrum of gartanin (1 0 1)

xix

EIMS spectrum of mangostanol(100)

IR spectrum of mangostanol(100)

'H NMR spectrum of mangostanol(100) (400 MHz, CD30D)

'H-'H COSY spectrum of mangostanol(100) (400 MHz, CD30D)

I3c NMR spectrum of mangostanol(100) (I 00 MHz, CD30D)

HSQC spectrum of mangostanol(100)

DEPT spectrum of mangostanol (1 00) (100 MHz, CD30D)

HMBC spectrum of mangostanol(100)

Isolation of chemical constituent from Mesua corneri

EIMS spectrum of stigmasterol (123)

IR spectrum of stigmasterol (123)

'H NMR spectrum of stigmasterol (123) (400 MHz, CDCL3)

13c NMR spectrum of stigmasterol (123) (100 MHz, CDCL3)

EIMS spectrum of friedelin (124)

IR spectrum of friedelin (124)

'H NMR spectrum of friedelin (124) (400 MHz, CDCL3)

13c NMR spectrum of friedelin (124) (I00 MHz, CDCL3)

13c NMR spectrum of friedelin (1 24) (1 00 MHz, CDCL3) (expanded) 158

EIMS spectrum of friedelan-] ,3-dione (125)

IR spectrum of friedelan- 1,3-dione (1 25)

'H NMR spectrum of friedelan-1,3-dione (125) (500 MHz, CDCL3)

'H NMR spectrum of friedelan-l,3-dione (125) (500 MHz, CDCL3) 167 (expanded)

I3c NMR spectrum of friedelan-1,3-dione (125) (125.65 MHz, 168 CDCL3)

I3c NMR spectrum of friedelan-1,3-dione (125) (125.65 MHz, 169 CDCL3) (expanded)

DEPT spectrum of friedelan- 1,3-dione (1 25) (125.65 MHz, CDCL3)

'H-'H COSY spectrum of friedelan-1,3-dione (125) (500 MHz, 171 CDCL3)

'H-'H COSY spectrum of friedelan-1,3-dione (125) (500 MHz, 172 CDCL3)(expanded)

HMQC spectrum of friedelan- 1,3-dione (1 25)

HMQC spectrum of friedelan-1,3-dione (125) (expanded)

HMQC spectrum of friedelan-1,3-dione (125) (expanded)

HMQC spectrum of friedelan-1,3-dione (1 25) (expanded)

HMQC spectrum of friedelan-1,3-dione (125) (expanded)

HMBC spectrum of friedelan-1,3-dione (125)

HMBC spectrum of friedelan-1,3-dione (1 25) (expanded)

HMBC spectrum of friedelan-] ,3-dione (125) (expanded)

HMBC spectrum of friedelan- 1,3-dione (1 25) (expanded)

HMBC spectrum of friedelan- I ,?-dione (125) (expanded)

EIMS spectrum of rubraxanthone (1 56)

1R spectrum of rubraxanthone (1 56)

'H NMR spectrum of rubraxanthone (1 56) (400 MHz, Me2CO)

'H NMR spectrum of rubraxanthone (156) (400 MHz, Me2CO) 191 (expanded)

'H-'H COSY spectrum of rubraxanthone (156) (400 MHz, Me2CO)

I3c NMR spectrum of rubraxanthone (1 56) (1 00 MHz, Me2CO)

HSQC spectrum of rubraxanthone (1 56)

DEPT spectrum of rubraxanthone (1 56) (100 MHz, Me2CO)

xxi

HMBC spectrum of nlbraxanthone (1 56)

EIMS spectrum of Inophyllin B (1 63)

IR spectrum of Inophyllin B (1 63)

1 H NMR spectrum of Inophyllin B (163) (400 MHz, CDCI3)

'H NMR spectrum of Inophyllin B (163) (expanded) (400 MHz, 204 CDCI3)

I NMR spectrum of Inophyllin B (163) (expanded) (400 MHz, 205 CDCI3)

COSY spectrum of Inophyllin B (163) (400 MHz, CDC13)

13 C spectrum of Inophyllin B (163) (100 MHz, CDCI3)

HSQC spectrum of Inophyllin 0 (163)

HMBC spectrum of Inophyllin B (162)

xxi i

CDCI3

COSY

d

dd

DEPT

DMSO

EA

EIMS

GC-MS

LIST OF A B E R ~ v I A T I ~ N S

alpha

beta

chemical shift in ppm

gamma

micro gram

broad singlet

broad triplet

carbon- 13

chloroform

deuterated chloroform

Correlated Spectroscopy

doublet

doublet of doublet

Distortionless Enhancement by Polarization Transfer

dimethylsulfoxide

doublet of triplet

ethyl acetate

Electron ionisation mass spectrometry

gram

Gas Chromatography

Gas Chromatography- Mass Spectrometry

xxiii

' H

HETCOR

HMBC

HPLC

ml

Me2C0

MeOH

m.p.

MS

NMR

PPm

S

t

TLC

UV

proton

Heteronuclear Chemical Shifbcorrelatibn

Heteronuclear Multiple Bond Connectivity by 2D Multiple Quantum

High Performance Liquid Chromatography

Hertz

Inhibition Concentration

Infra Red

coupling constant irl Hz

litre

Lethal Concentration

Lethal Dose

multiplet

mililitre

acetone

methanol

melting point

Mass Spectrum/Spectra/Spectrometry

Nuclear Magnetic Resonance

part per million

singlet

triplet

Thin Layer Chromatography

Ultra Violet

xxiv

WHO World Health Organization