OPTIMIZATION OF SWIETENIA MAHAGONI SEED IN SUPERCRITICAL

CARBON DIOXIDE EXTRACTION

NOR ASYIQIN BINTI BAKERI

UNIVERSITI TEKNOLOGI MALAYSIA

OPTIMIZATION OF SWIETENIA MAHAGONI SEED IN SUPERCRITICAL

CARBON DIOXIDE EXTRACTION

NOR ASYIQIN BINTI BAKERI

A thesis submitted in fulfilment of the

requirements for the award of the degree of

Master of Engineering (Bioprocess)

Faculty of Chemical and Energy Engineering

Universiti Teknologi Malaysia

MARCH 2017

iii

To my beloved family

iv

ACKNOWLEDGEMENT

Firstly, Praise is to God, Almighty ALLAH, the Cherisher and Sustainer of

the Worlds. We are grateful to Him who create and control the universe. Only

through His blessing that this humble work could reach the present form.

My profound gratitude and appreciation are assigning to my supervisor, Dr

Liza Bt Md Salleh for her efforts and on-going supports and constant

encouragements. To Dr Shafii bin Khamis, thank you for advice as well as guidance,

during my present at Agensi Nuklear Malaysia.

I also would like to extend my special thanks and appreciation to my beloved

parent and all my fellow friends that gave me a lot of helps and gave valuable

advices and tips when I encountered problems during the preparation of this research.

Last but not least, again, I would like to take this opportunity to express my

heartfelt gratitude to all the persons and organizations that have directly or indirectly

given generous contributions towards the success of this research.

v

ABSTRACT

Supercritical carbon dioxide extraction has been used for extraction of

essential oil from Swietenia mahagoni seed. The effect of different particle sizes on

diffusivity coefficients, D (m2/s) were studied by applying second Fick’s law of

diffusion proposed by Crank. Particle size of 710 μm showed the highest D of 3.1 x

10-12

m2/s. Gas compression at pressure of 30 MPa and temperature of 60

oC on

seeds caused swelling thus allowed faster diffusion of carbon dioxide through porous

structure of Swietenia mahagoni seed. For optimization of Swietenia mahagoni seed

oil extraction, a three-level factorial design in response surface methodology was

used to analysis the effect of pressure (20 – 30 MPa) and temperature (40 - 60 oC) on

extraction oil yield. The highest extraction oil yield of 29.70% was obtained at

pressure of 30 MPa and temperature of 40 oC. This explained that increased pressure

and low temperature increased the carbon dioxide density. Thus, higher solute

bonding in solvent phase and consequently higher the extraction yield was obtained.

Qualitative phytochemical analysis showed the presense of alkaloid, saponin,

triterpenoid, phenolic hydroquinone and tannin but absense of flavonoid. Toxicity

test of Swietenia mahagoni seed extract using 3-(4,5-dimethylthiazol-2-yl)-2,5-

diphenyltetrazolium bromide assay on human skin fibroblast cell (HSF 1184)

showed cell viability above 80%. The result showed that Swietenia mahagoni seed

extracts at studied concentrations (10, 1, 0.1, 0.01, 0.001, 0.0001 mg/ml) are non

toxic.

vi

ABSTRAK

Aplikasi pengekstrakan menggunakan bendalir lampau genting karbon

dioksida telah digunakan untuk mengekstrak minyak dari biji Swietenia mahagoni.

Kesan perbezaan saiz zarah kepada pekali keresapan, D (m2/s) telah dikaji

menggunakan hukum kedua resapan Fick’s yang disarankan oleh Crank. Saiz zarah

710 μm menunjukkan D yang tertinggi sebanyak 3.1 x 10-12

m2/s. Pemampatan gas

pada tekanan 30 MPa dan suhu 60 oC ke atas biji Swietenia mahagoni

menyebabkannya bengkak dan seterusnya membenarkan resapan karbon dioksida

menembusi struktur ruangnya dengan lebih cepat. Untuk tujuan pengoptimuman

pengekstrakan minyak biji Swietenia mahagoni, reka bentuk faktorial tahap-tiga

dalam kaedah gerak balas permukaan telah digunakan untuk menganalisa kesan

tekanan (20 – 30 MPa) dan suhu (40 – 60 oC) ke atas hasil pengekstrakan minyak.

Hasil tertinggi pengekstrakan minyak sebanyak 29.70% telah diperoleh pada

tekanan 30 MPa dan suhu 40 oC. Ini menjelaskan bahawa pada peningkatan tekanan

dan suhu rendah, ketumpatan karbon dioksida meningkat. Oleh itu, ikatan bahan

larut yang lebih tinggi dalam fasa pelarut dan seterusnya lebih banyak hasil

pengekstrakan telah diperoleh. Analisis fitokimia kualitatif menunjukkan kewujudan

alkaloid, saponin, triterpenoid, fenolik hidrokuinon dan tanin tetapi tiada flavonoid.

Ujian ketoksikan biji Swietenia mahagoni yang diekstrak menggunakan assai 3-(4,5-

dimetiltiazol-2-yl)-2,5-difeniltetrazolium bromida ke atas sel fibroblas kulit manusia

(HSF 1184) menunjukkan kebolehhidupan sel melebihi 80%. Ini menunjukkan

ekstrak biji Swietenia mahagoni pada kepekatan yang berbeza (10, 1, 0.1, 0.01,

0.001, 0.0001 mg / ml) adalah tidak toksik.

vii

TABLE OF CONTENTS

CHAPTER TITLE PAGE

DECLARATION ii

DEDICATION iii

ACKNOWLEDGEMENTS iv

ABSTRACT v

ABSTRAK vi

TABLE OF CONTENTS vii

LIST OF TABLES xii

LIST OF FIGURES xiv

LIST OF ABBREVIATIONS xvi

LIST OF SYMBOLS xvii

LIST OF APPENDIX xviii

1 INTRODUCTION 1

1.1 Background of the study 1

1.2 Problem statement 2

1.3 Objectives of research 3

1.4 Scopes of research 4

1.5 Thesis summary 4

2 LITERATURE REVIEW 6

2.1 Medicinal plants 6

2.2 Introduction of Swietenia mahagoni 7

2.3 Chemical constituents of Swietenia mahagoni 10

2.4 Limonoids 11

2.5 Previous Study of Limonoids in Swietenia mahagoni 15

2.6 Traditional uses and validation 18

ix

2.7 Extraction process of medicine and aromatic plant 18

2.8 Soxhlet extraction process 19

2.9 Supercritical fluid extraction (SFE) process 20

2.9.1 Selection of extraction time 21

2.9.2 Selection of carbon dioxide flow rate 21

2.9.3 Carbon dioxide as extraction solvent 22

2.9.4 Selection of pressure and temperature 25

2.9.5 Selection of particle size 27

2.10 Diffusivity of carbon dioxide in supercritical fluid

extraction 27

2.10.1 Introduction of diffusion 27

2.10.2 Mechanism of mass transfer in SFE 28

2.10.3 Diffusion by Crank model 30

2.10.4 Diffusivity model from previous research 32

2.11 Phytochemical analysis of plant extract 34

2.12 Toxicity activity of plant extract 34

3 METHODOLOGY 36

3.1 Introduction 36

3.2 Chemicals 38

3.3 Apparatus and instruments 38

3.4 Sample preparation 38

3.5 Soxhlet extraction method 39

3.6 Supercritical carbon dioxide extraction method 39

3.7 Preliminary study on supercritical carbon dioxide

extraction process 39

3.8 Diffusivity of carbon dioxide at different particle size 40

3.9 Optimization of supercritical carbon

dioxide extraction process 41

3.10 Experimental result analysis 42

3.10.1 Extracted oil yield 42

3.10.2 Overall extracted oil yield percentage 42

3.10.3 Diffusivity of carbon dioxide in supercritical

carbon dioxide extraction process 43

3.11 Experimental design for response surface

methodology (RSM) 43

x

3.12 Qualitative phytochemical analysis 45

3.12.1 Alkaloid test 45

3.12.2 Saponin test 45

3.12.3 Flavonoid test 45

3.12.4 Phenolic hydroquinone test 46

3.12.5 Triterpenoid test 46

3.12.6 Tannin test 46

3.13 In vitro toxicology test on human skin fibrolast

1184 (HSF 1184) 46

3.13.1 Cell recovery 47

3.13.2 Cell subculture 47

3.13.3 Cell cryopreservation 47

3.13.4 Cell viability 48

3.13.5 MTT assay 49

4 RESULT AND DISCUSSION 50

4.1 Introduction 50

4.2 Selection of extraction process 50

4.3 Diffusivity coefficients, D of carbon dioxide on

different particle size 53

4.4 Optimization of supercritical carbon dioxide

extraction process 57

4.4.1 Experimental matrix 57

4.5 Statistical analysis on overall Swietenia mahagoni

seed oil 58

4.5.1 Response surface methodology (RSM)

analysis 59

4.5.2 Response surface and contour plot on oil

yield 62

4.5.3 Experimental and expected extraction of

Swietenia mahagoni seed oil yield 65

4.6 Response optimization of supercritical carbon

Dioxide extraction 66

4.7 Analysis on qualitative phytochemical of Swietenia

mahagoni seed oil 67

4.8 In vitro toxicity analysis of Swietenia mahagoni

seed oil 68

xi

5 CONCLUSION AND RECOMMENDATION 70

5.1 Conclusion 70

5.2 Recommendation 71

REFERENCES 72 – 78

APPENDIX A 79

xii

LIST OF TABLES

TABLE NO. TITLE PAGE

2.1 Scientific classification of Swietenia mahagoni 8

2.2 Fatty acid compounds found in Swietenia mahagoni

seed oil 10

2.3 Physico-chemical characters of Swietenia mahagoni

seed oil 11

2.4 Plants from family that has limonoids 12

2.5 Comparison of gas, liquid and supercritical state of

typical values with respect to density, viscosity and

diffusivity 22

2.6 Critical conditions of several solvents (Marrtje, 2005) 24

2.7 Bioactive substances present in Swietenia mahagoni 34

3.1 Preliminary study on parameters for overall

supercritical carbon dioxide extraction process. 40

3.2 Constant parameter in supercritical carbon dioxide

extraction process 40

3.3 Independence parameter range in supercritical

carbon dioxide extraction process 41

3.4 Constant parameter in supercritical carbon dioxide

extraction process 41

3.5 Parameter ranging in supercritical carbon dioxide

extraction process 41

3.6 3-level factorial design of RSM 44

4.1 Experimental conditions for supercritical carbon

dioxide extraction and soxhlet extraction 52

4.2 Comparison of particle size on total extract Swietenia

mahagoni seed oil 53

4.3 Comparison of particle size on diffusivity 54

xiii

4.4 The oil weight and oil yield at various pressures

and temperatures 58

4.5 Table of coded and uncoded levels of independebt

variables in RSM 58

4.6 Experimental scheme and results obtained from RSM 59

4.7 ANOVA for response surface quadratic model 60

4.8 Regression coefficient for Swietenia mahagoni seed

oil yield 61

4.9 Experimental and predicted value of Swietenia

mahagoni seed oil yield 65

4.10 The optimum condition proposed by model for

maximum extraction oil yield. 67

4.11 The comparison value of extraction oil yield in

optimum condition 67

4.12 Qualitative phytochemical analysis of Swietenia mahagoni

seed oil. 67

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LIST OF FIGURES

FIGURE NO. TITLE PAGE

2.1 Swietenia mahagoni tree 9

2.2 Swietenia mahagoni seed 9

2.3 Structure of limonin of citrus 12

2.4 Skeletal arrangement of 14 groups of limonoids 14

2.5 Limonoids structure from Swietenia mahagoni seed

found by (a) Shahidur Rahman et al (2009).

(b) Govindachari et al.,(1990) and (c) Shigetoshi

Kadota et al.,(1990) 16

2.6 Limonoids structure from Swietenia mahagoni leaf

found by (a) Yu-yu Chen et al.,(2007) and (b) Samir A.M

Abdelgaleil et al.,(2006) 17

2.7 Soxhlet extraction apparatus 20

2.8 Schematic design of Supercritica; fluid extraction unit. 21

2.9 Schematic phase diagram for pure CO2 (a) at critical

temperature, Tcr and critical pressure, Pcr (b) at density

of the CO2 as the function of pressure at different temperature 23

2.10 Respond surface plot on effect of temperature, Z1 and

pressure, Z2 on oil yield for 3 hours extraction time 26

2.11 Respond surface plot on effect of pressure and time on

oil yield at 55 C temperature 26

2.12 Schematic description of the mechanism of supercritical

fluid extraction 30

2.13 Mean quadratic error between experimental and

modelled result 33

2.14 Diffusivity coefficient of different extraction process

with respect to fast extraction process and slow

extraction process 33

3.1 Experimental design of research 37

4.1 Comparison between SC-CO2 and soxhlet extraction 51

xv

4.2 Percentage oil yield with respect to time fraction for

particle size 355μm of Swietenia mahagoni seed 55

4.3 Percentage oil yield with respect to time fraction for

particle size 500μm of Swietenia mahagoni seed 56

4.4 Percentage oil yield with respect to time fraction for

particle size 710μm of Swietenia mahagoni seed 56

4.5 Contour plot for the effect of temperature and pressure

on extraction oil yield. 62

4.6 3D response surface of extraction oil yield of

Swietenia mahagoni seed as a function of temperature

and pressure. 63

4.7 Predicted versus actual values of Swietenia mahagoni

seed oil yield. 66

4.8 Cell viability on different Swietenia mahagoni concentration 69

xvi

LIST OF ABBREVIATIONS

ANOVA - Analysis of Variance

C - Concentration

CO2 - Carbon Dioxide

HSF - Human Skin Fibroblast

LM - Logistic Model

MAE - Microwave-Assisted Extraction

MEM - Modified Eagle Medium

MOX - Malaysian Oxygen

OEC - Overall Extraction Curve

PAF - Plattelet-Activating Factor

PBS - Phosphate Buffer Saline

RSM - Response Surface Methodology

SC-CO2 - Supercritical Carbon Dioxide

SFE - Supercritical Fluid Extraction

SSP - Simple Single Plate

TPC - Total Phenolic Content

UAE - Ultrasonic-Assisted Extraction

USA - United State America

xvii

LIST OF SYMBOLS

a, b, c - Constants in the Density Based Model

°C - Degree celcius

D - Diffusivity coefficient

k - Associated Number

K - Kelvin

MA - Molecular weight of the solute

MB - Molecular weight of the gas solvent

MPa - Mega Pascal

ρ - Density

P - Pressure

R - Gas constant

T - Temperature

Y - Oil yield

xviii

LIST OF APPENDIX

APPENDIX TITLE PAGE

A F test table 79

CHAPTER 1

INTRODUCTION

1.1 Background of the Study

Traditional plants have contributed to development of novel pharmaceutical,

neutraceutical and cosmetic applications. Plant poses a vast array of natural products,

bioactive primary and secondary metabolites. Seed is part of plant that important as

primary stage of plant life cycle. Therefore, it has strong defense mechanisms. It is

dues to attributions of biologically active phytoconstituents in them.

Swietenia mahagoni comes from Meliaceae family is a large, deciduous, and

economically important timber tree native to the West Indies which is commonly

known as mahogani. Swietenia mahagoni is a medium-sized semi-

evergreen tree growing to 30–35 meters tall. The leaves are pinnate, 12 to 25

centimeters long, with four to eight leaflets. The flowers are small, produced

in panicles. The fruit is a woody capsule 5 to 10 centimeters long and 3 to 6

centimeters broad, containing numerous winged seeds (Khare et al., 2012).

Swietenia mahagoni seed has potentials as antimicrobial activity, antioxidant

activity (Mayur et al., 2011), cytotoxic activity, antiulcer activity, antifungal activity,

anti-HIV activity, anti-inflamatory and antipyretic activity (Majid et al., 2004), and

hypoglycemic activity (Sahgal et al., 2009; Debasis et al., 2011). Swietenia

mahagoni seed was traditionally used as antidiabetic in several countries including

2

Malaysia, Indonesia, China and India. Furthermore, studies on antidiabetic potential

of Swietenia mahagoni seed extracts on diabetic induced rats have been done and it

shows a positive result (Debasis et al., 2011). From the previous study, Swietenia

mahagoni afforded with two limonoids which are swietenolide and 2-hydroxy-3-O-

tigloylswietenolide (Tan, 2009).

Due to fast development, people have better understanding on natural

products. Thus, many researched have been conducted in studying the active natural

products as medicines, food additives, cosmetic application and natural pesticides.

Extraction is a separation process of oil from plant. There are two categories of

extraction, conventional and non-conventional methods. Compared with

conventional method of extraction, supercritical fluid extraction has gained wide

acceptance in many analytical and industrial processes. Moreover, supercritical fluid

extraction has been used for decades on extraction of essential oil from plants.

Previous literature reported that the applications of supercritical fluid extraction have

focused more on edible oil extraction as examples, palm kernel oil (Hassan et al.,

2000), black pepper (Dang et al., 2014), sunflower seed (Salgin et al., 2006), olive

oil (Fornari et al., 2008) and Leptocarpha rivularis (Edgar et al., 2015).

Wai (2003) reported that supercritical carbon dioxide extraction has many

beneficial as it has low toxicity, in expensive and not harm to nature. This is because,

physical properties of carbon dioxide at supercritical state has low critical

temperature and critical pressure made supercritical carbon dioxide environmentally

friendly and green solvent.

1.2 Problem Statement

Swietenia mahagoni has been used traditionally as treatments such as

diabetes, asthma, eczema, premenstrual syndrome and migraine. Especially seed, it

has potential of antioxidant activity, antimicrobial activity, antifungal activity and

3

hyperglycemic activity. Selection of extraction method is crucial to ensure the extract

in high purity, rich with components and non toxic.

Supercritical fluid extraction method has been used for separation and

extraction of essential oil from plants commercially. But, the high capital, high

operating investment and higher pressure needed in the process contributes to

problem for commercial. Temperature and pressure are two important parameters

that will control whole extraction process. Size of particles also plays important roles

for extraction yield. Carbon dioxide is selected as solvent for extraction process.

Therefore, optimization of extraction process is crucial. Moreover, different plants

have different optimization process especially on pressure, temperature, sample

particle size and polarity of compounds.

Carbon dioxide as supercritical fluid as extraction solvent has low viscosity

and higher diffusivity compared to other liquids. Moreover, supercritical fluid has

beneficial as it has great transport properties which can diffuse through solids more

easily compared to liquid. For optimizing the operating conditions and extraction

process design a vase area of knowledge on the mechanism and kinetics of extraction

processes is required. Mathematical modelling of extraction processes from different

herbaceous materials has been of great importance for design purposes because it

allows generalization of the experimental results and successful prediction of the

extraction kinetics. A mathematical model based on the second Fick’s Law, which

was introduced by Crank, has been widely used to describe the process of unsteady

diffusion in the solid phase for different extraction processes and particle geometries.

From constant temperature and pressure parameter, the best diffusivity coefficients

of sample with different particle size will be chosen for optimization process.

1.3 Objectives of Research

The researched is conducted based on following objectives;

4

1. To investigate the effect of diffusivity coefficients on particle size of

Swietenia mahagoni seed using diffusivity model.

2. To study the effect of pressure and temperature on extraction yield and

biological analysis of Swietenia mahagoni seed.

1.4 Scopes of Research

The extraction of Swietenia mahagoni seeds was done at selected range of

conditions using supercritical carbon dioxide extraction. In order to achieve the

objectives stated in section 1.3, the scopes of study are as follows:

1. Extraction of Switenia mahagoni seeds using supercritical carbon dioxide

extraction process

2. Determination of diffusivity coefficients of carbon dioxide at different

particle size of Swietenia mahagoni seeds by application of mathematical

model second Fick’s law proposed by Crank.

3. Optimization of pressure and temperature on extraction process using

Response surface methodology (RSM)

4. Statistical analysis using ANOVA

5. Biological analysis on quality of phytochemicals and toxicity of Swietenia

mahagoni seed oil.

1.5 Thesis Summary

This thesis is divided into five main chapters. Chapter 1 is the introduction of

the research that included background of the research, problem statement, objectives

5

and scopes of the research. Chapter 2 included the overview of Swietenia mahagoni,

extraction process involved, mathematical modeling namely Crank model and

process optimization. Chapter 3 discussed the overall methods used in the research

including the procedures of chemicals and raw material preparation, extraction

process involved (soxhlet and supercritical carbon dioxide extraction), diffusivity

measurement and modeling, and process optimization also biological study methods

on qualitative phytochemical and toxicity of Swietenia mahagoni seed oil. Chapter 4

discussed the results and discussion for overall experiments while the conclusion and

some recommendations were discussed in Chapter 5.

72

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