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Humanity is faced with numerous health challenges ranging from severe to chronic disease conditions, such health challenges common to mankind among others include pains, arthritis, inflammations and rheumatism. Newbouldia laevis P. Beauv (farm Bignoniaceae) is used in traditional herbal medicine for the treatment of the health challenges mentioned above. We are motivated by the use of N. laevis leaves in traditional medicine to extract, isolate and characterize the bioactive components which may be responsible for its analgesic properties. Pulverized leaves sample of N. laevis was extracted by cold maceration using methanol. The extract was concentrated in vacuo to yield a reddish brown solid 120.191 g. The crude methanol extract was partitioned into n-hexane 0.1 g, dichloromethane 2.5 g, ethlylacetate 4.6 g, and methanol 10.0 g, fractions via coarse chromatography. The phytochemical screening reveals the presence of secondary metabolites as 21.73±0.36 % alkaloids, 40.78±0.27 % flavonoids, 15.99±0.044 % saponins, 6.088±0.06 % Tannins, 3.086±0.03 % Trepenoids and 12.13±0.01 % Cardiac Glycosides, with alkaloids, flavonoids and saponins having the highest percentage. The methanol fraction gave the highest yield; and it was subjected to further purification using repeated column chromatography to yield pure components namely NLM 24 (Rf 0.48), EAc:n-hex:MeOH (4:5:1) and NLM 19 (Rf  0.47), EAc:n-hex:MeOH respectively. These pure fractions were subjected to 1H NMR, 13C, COSY, HSQC and HMBC spectroscopy. Pheophytin A and β-amyrin were proposed as the structures of the isolated compounds. Acute toxicity test and analgesic test were done using the crude methanol extract and fractions. The acute toxicity test shows no death of the white whisker rats administered with low dose (1000 mg/kg) and high dose (6000 mg/kg), meaning that the leaves are edible. The analgesic activities of the crude methanol extract and fractions on white whisker rats showed that at low dose of 4000 mg/kg of the extract and the fractions have percentage inhibition of pains as; methanol crude (63.48±4.62), methanol fraction (79.14±7.39), dichloromethane fraction (60.79±6.69), ethylacetate fraction (23.26±9.75), and n-hexane fraction (64.82±9.75). At high dose of 8000 mg/kg, the percentage inhibition of pain are 5200±2.00, 71.87±7.04, 80.31±6.20, 45.61±12.60, 43.87±8.13 percent respectively; a statistical analysis at (P>0.05), confidence level the methanol fraction had the highest analgesic activities while the ethylacetate fraction had the least analgesic activity. The non-toxic effect of the extract on the rats showed why the leaves of N. laevis are cooked and consumed for pain relief in folk medicine. Even though the pure fractions were not used for analgesic activity, literature work reveals that pheophytin A & β-amyrin are potent analgesics. This may be the first time pheophytin A and β-amyrin are isolated from N. laevis leaves P. Beauv.



Title page                                                                                                                                i

Declaration                                                                                                                              ii

Certification                                                                                                                            iii

Dedication                                                                                                                              iv        

Acknowledgments                                                                                                                  v

Table of Contents                                                                                                                   vi

List of Tables                                                                                                                          ix

List of Figures                                                                                                                         x

List of Plates                                                                                                                           xi

List of Appendices                                                                                                                 xii

Abstract                                                                                                                                  xiii


CHAPTER 1: INTRODUCTION                                                                                      1

1.1       Background of the Study                                                                                          1

1.2       Statement of the Problem                                                                                          4

1.3       Aim and Objectives of the Study                                                                               5

1.4       Justification of the Study                                                                                           5

1.5       Significance of the Study                                                                                           5

1.6       Scope and Limitations of the Study                                                                           6


CHAPTER 2: LITERATURE REVIEW                                                                          7

2.1       General Botanical Characteristics of Newbouldia laevis                                            8

2.2       Chemical Constituents of Newbouldia laevis P. Beauv                                              11

2.2.1    Phytochemicals                                                                                                           11

2.2.2    Alkaloids                                                                                                                     12

2.2.3    Flavonoids                                                                                                                  14

2.2.4    Saponins                                                                                                                      16

2.2.5    Steroids                                                                                                                       18

2.2.6    Tannins                                                                                                                        21

2.2.7    Cardiac glycosides                                                                                                      23

2.2.8    Terpenoids                                                                                                                  25

2.3       Analgesics                                                                                                                   27

2.3.1    Synthetic natural analgesic                                                                                         27

2.3.2    Natural analgesics                                                                                                       30       

2.3.3    Analgesic effects of Newbouldia laevis P. Beauv                                                      32

2.4       Acetic Acid Induced Writhing                                                                                   32

2.5       Activities Attributed to Newbouldia laevis leaves                                                     33

2.6       Chromatography                                                                                                         35

2.6.1    Thin layer chromatography     (TLC)                                                                         36

2.6.2    Column chromatography                                                                                            36

2.7       Current Trend in Structure Elucidation of Organic    Compounds                            37

2.8       Spectroscopy                                                                                                               37


CHAPTER 3:            MATERIALS/EQUIPMENT                                                                     43

3.1       Materials for Extraction                                                                                              43

3.2.0    Methods                                                                                                                      45

3.2.1    Summary of experimental procedure                                                                          45

3.2.2    Collection and preparation of plant material                                                              47

3.2.3    Extraction and fractionation                                                                                       47

3.2.4    Column chromatography                                                                                            48       

3.2.5    Thin layer chromatography (TLC)                                                                              49

3.2.6    Phytochemical screening                                                                                             50

3.4.1    Toxicity test                                                                                                                53

3.4.2    Analgesic test                                                                                                              54

3.4.3    Spectroscopic analysis                                                                                    55


CHAPTER 4: RESULTS AND DISCUSSIONS                                                              56

4.1       Result of Quantitative Phytochemical Screening                                                       57

4.2       Result of Column Chromatography                                                                            60

4.3       Thin layer Chromatography    (TLC) Result                                                              65

4.4       Spectral Analysis Result                                                                                             67

4.5       Spectroscopic Analysis of Isolated Compounds                                                        69

4.5.1    Characterization of NLM 24 as pheophytin A                                                           69

4.5.2    Characterization of NLM19 as -Amyrin                                                                   75


CHAPTER 5: CONCLUSIONS AND RECOMMENDATIONS                                               83

5.1       Conclusions                                                                                                                 83

5.2       Recommendations                                                                                                      84

5.3       Contribution to Knowledge                                                                                        84

REFERENCES                                                                                                                    86

APPENDICES                                                                                                                      97









2.1:  Active compounds Isolated from Natural Sources                                                         30

2.2:  Activities Attributed to Newbouldia Laevis leaves                                                        33

3.1:  Chemicals and Reagents                                                                                                 44

3.2:  Equipment, Samples Obtained and the Laboratory where the Experiments was Done 55

4.1:  The Extracts NLM, NLE and NLDCM with their yields and appearance                    56

4.2:  Result of Qualitative and Quantitative Phytochemical Screening of Methanol Crude

        Extract of  N.laevis leaves                                                                                              57

4.3:  Result of Column Chromatography result of Newbouldia laevis Leaves Extract          60

4.4:  1H(400MHZ) and 13CNMR (100MHZ) data of NLM 24 and Literature data in CDCL3 67

4.5:  1H(500MHZ) and 13C(125MHZ) NMR Data of NLM19 and Literature Data in CDCL3 74

4.6:  Acute Toxicity Study of Methanol leave Extract of Newbouldia leavis LD50 result of the Extract                                                                                                                     79

4.7:   Analgesic Effects of the Crude Methanol Extract and its Fractions of the Leaf Extracts

         of  Newbouldia leavis on Whisker Albino Rat.                                                             81











1.         Withasomine                                                                                                   13

2.         4-Hydroxynewbouldine                                                                                  13

3.         3- Hydroxynewbouldine -      Lapachone                                                       15

4.         5- Hydroxynewbouldine -      Lapachone                                                       15

5.         Lapachol                                                                                                         15

5.         Oleanolic Acid                                                                                                17

6.         Glycyrrhizin                                                                                                    17

7.         Ginsenosides                                                                                                   17

8.         Beta-sitosterol                                                                                                 20

9.         Stigmasterol                                                                                                    20

10.       2,3,4,6-tetra-o-galloyl-D- glucopyronose                                                        22

11.       Ellagitannins                                                                                                   22

12.       Digoxin                                                                                                           24

13.       Ouabain                                                                                                           24

14.       Oleandrin                                                                                                        24

15.       Ursolic acid                                                                                                     26

16.       Canthic acid                                                                                                    26

17.       Summary of Experimental procedure                                                             45

18.       Flow Chart of Purification using Flash Chromatography                               46

19.       Structure of pheophytin A                                                                              73

21.       Structure of  (-amyrin)                                                                                  78


22.       The percentage analgesic activities of different doses of the extracts           81










1.      Newbouldia laevis leaves                                                                                      10

2.      TLC  chromatogram for NLM 24 and 19                                                             66










1H-NMR spectrum for NLM 24 (Pheophytin A)                                                      97

13C spectrum for NLM 24 (pheophytin A)                                                                98

COSY NMR Spectrum for NLM 24 (Pheophytin A)                                                            99

HSQC NMR Spectrum for NLM 24 (Pheophytin A)                                                            100

HMBC NMR Spectrum for NLM 24 (Pheophytin A)                                               101

1H NMR Spectrum for NLM 19 (-amyrin)                                                              102

13C  NMR Spectrum for NLM 19 (-amyrin)                                                           103

COSY NMR Spectrum for NLM 19 (-amyrin)                                                        104

HSQC NMR Spectrum for NLM 19 (-amyrin)                                                        105

HMBC NMR Spectrum for NLM 19 (-amyrin)                                                       106










 Nature has provided vegetation to mankind, such vegetation comprises of abundant medicinal plants of different diversities such as herbs, shrubs, sub-shrubs, grasses and plants located in different habitats like tropical Rain Forest, Savanna Grass Land, Sahel Savanna and desert regions of the world. The various medicinal plants parts like the root, bark, stem, flower, leaves, fruits and seeds could be used in both folklore and allopathic medicine to fight against numerous health challenges so as to enhance healthy living of the populace.


Presently, humanity is faced with different challenges due to proliferation of diseases caused by organisms found everywhere in the environment.

Ainooson, (2009) opined that the use of plants in the management and treatment of diseases is an age long practice. According to him, it is no doubt that in the recent times with good number of research, it has been found that many plants possesses medicinal value and different parts of these plants have been useful for the synthesis of medicines used in hospitals, clinics, and other health care centers. Tietz (2000) stated that traditional medicine is leading the front line research for finding solution to many health challenges which are so common in the society. In Nigeria, many diseases were treated and are still being treated with the use of folk medicine and most of them have so far shown positive results. These diseases among others include pains, muscle inflammation, ulcers, convulsions, diarrhea, bacterial and fungal infections, asthma, malaria, diabetes, and typhoid fever. Some of the numerous medicinal plants already in use in Nigeria are: Garcina kola, which is used for the treatment of asthma, Carica papaya used for hypertension, Ocinum basilicum for typhoid fever, Senna occidentalis for skin diseases and Newbouldia laevis for pains, (Burtis, et al, 2003). WHO (2005), recognized the place of herbal or folks medicine in primary healthcare with greater interest in different developing countries of the world. (WHO) further encouraged member nations to develop national policies for identification, sustainable exploitation, scientific development and appropriate use of herbal medicines so as to salvage their situations.


The efficacy of these medicinal plants are based primarily on their diverse phytochemical constituents. In the light of this, plants contain an array of phytochemicals that are certified to be pharmacologically active and have been mostly utilized in the treatment of many diseases wrecking both man and animals Schneidar, (2004).


Oliver Bever, (1986), stated that a very greater area of Nigeria ecological zones is made up of numerous plant species which have found their usefulness to the healthcare of the populace. According to Bruneton (1994), the medicinal uses of most of these plants are numerous and cannot be exhausted in respect of oral traditions and folklores from the time immemorial that have continued to increase the medicinal potencies of these plants and their crude extracts. He further stated that there are different bioactive principles embedded in the medicinal plants such as flavonoids, alkaloids, tannins, saponins, glycosides, etc. These bioactive principles obtainable from a wide range of pharmaceutically derived medications consist of components which are obtained from phytochemicals in plants. The bioactive principles in medicinal plants possess the healing property attributed to such plant (Alves et al., 2007).

The medicinal plant secondary metabolites are believed to be intermediates in metabolic processes found in nature and are usually small molecules. Primary metabolites are involved directly in normal growth, development and reproduction for example, (ethanol, acetic acid, citric acid, and lactic acid) and cell components (lipids, vitamins and polysaccharides). Secondary metabolites on their own are not directly involved in those processes and usually has a duty not important for the organisms (e.g. antibiotics, proteins and carotenoids).


One of such medicinal plants abundant in nature is Newbouldia laevis P.Beauv (Bignoniaceae). The plant is known to possess great potency in the cure and treatment of elephantiasis, syphilis, rheumatic swellings, and as a vermifuge to roundworms. The plant has also been identified to be useful in the treatment of sore feet, ear ache, chest pain, children’s’ convulsion and epilepsy (Akunyili, 2000). The leaf, stem, and fruits have been reportedly used for febrifuge, stomach ache and wound dressing Iwu, (2000). A lot of ethno medicinal activities have been reported to be associated to Newbouldia laevis leaves extract such as uterine stimulant, treatment of arthritis and rheumatism, gastro-intestinal treatment and all kinds of body pain (Bafor and Sanni, 2009).


Investigations from Sofowara, (1993) revealed a number of phytochemicals are embedded in Newbouldia laevis. The leaves of N.laevis P.Beauv (Bignoniaceae) is used in folks medicine for the treatment of various ailments like body pain, rheumatism, arthritis, inflammations and others, the crude extract has been found potent on some diseases, this is why the decoction of the leaves are consumed locally as a remedy to many health challenges, there are important drugs isolated from N. laevis leaves such as digoxin,and digitoxin which are useful in the treatment of congestive heart failure (Thompsons, 2008). Taxol is another drug extracted from the plant. Taxol is used as a cancer chemotherapeutic drug, (Stierle,et al.1993). Newbouldine is another drug for pain relief and antimalarial ( Also lysergic is a drug produced from ursolic acid obtained from newbouldia laevis (Halpern et al.,2014).

According to Liu (2004), phytochemicals are chemical substances that are found naturally in plants, some of the phytochemicals are responsible for colour and organoleptic properties such as the deep purple of blueberries and the smell of garlic, while a good number of others are the principles responsible for much of the protection conferred on fruits, plants, vegetables, cereals, beans, and plant based beverages like tea and wine. Phytochemical screening of the methanolic- extract showed the presence of flavonoids, tannins, glycosides, alkaloids, terpenes and steroids (Sofowara, 1993; Trease and Evans, 2002).

Research done recently by (Seed et al 2008), revealed that the leaf crude methanol extract using white whisker albino rats showed no toxic effect at LD50>6000 mg/kg.  Similar research was conducted by the researcher on the same laboratory animals and the plant was found to be a very active analgesic at all concentrations and doses. Despite a whole lot of research in human medicine, challenges are still encountered, one of those leading challenges is body pain which arises from other ailments and as symptoms of a particular sickness; the effect of such medicinal disease condition is prevalent in Nigeria; this is due to relative unavailability of medicines with a promising efficacy and proliferation of adulterated analgesic drugs (Sagganuwan and Gulumbe, 2006). This research mainly focuses attention on extraction of the bioactive principles of the plant, elucidation of their structures and evaluation of their analgesic efficacy on some laboratory animals.



The inefficiency of analgesic drugs like Ibumol, Paracetamol, Ibuprofen and Diclofenac on pain relief has made it necessary for the discovery of new organic compounds that will be more efficacious for analgesic purposes, the extraction of bioactive- principles from Newbouldia laevis and essential elucidation of their structures may lead to the discovery of new organic molecules that may be more effective for pain relief without much side effect.


The research is aimed at the isolation and characterization of secondary metabolites from the leaves of N. laevis. This aim is hoped to be achieved through the following specific objectives;

i.                    to isolate bioactive compounds in the leaf of Newbouldia laevis.

ii.                  to elucidate the structures of the bioactive compounds.

iii.                to access the analgesic activities attributed to the leaf of Newbouldia laevis.

iv.                to access the toxicity profile of Newbouldia laevis.

v.                  to isolate the phytochemicals embedded in the leaf of Newbouldia laevis.



Newbouldia laevis leaf is utilized in orthodox medicine in different Africa countries for the treatment of various diseases such as pains, cancer, eye and ear diseases, bacteria infection, cough, heartburn, snake bite, constipation, vermifuge, ophthalmia, septic wounds, diarrhea, oedema, rheumatism and arthritis, malaria, conjunctivitis, headache among others. Though the leaf of this plant is utilized in the treatment of pain locally, there is no scientific proof of its pain-killer properties. Results from this research would add to the database of information on the leaf of Newbouldia laevis.


1.5       SIGNIFICANCE OF THE STUDY          

This research on the leaves of N. laevis P. Beauv (Bignoniaceae), is important from both literature work and experimental analysis. For the literature aspect, the research is built on previous work done so far on the leaves of the plant which gives the insight on the ethnomedicinal uses of the plant. On the part of experimentation, the findings may be of relevant to researchers, pharmaceutical industries for production of more potent analgesic drugs and also to traditional herbalists for effective cure of rheumatic pain, arthritic pain, inflammations, menstrual pains e.t.c. the findings will equally help researchers by providing the basic empirical information to do further work on the plant.


The study covers a wider area of scientific research such as plant collection and identification, extraction, phytochemical screening, partitioning followed by chromatography, spectra analysis Bioassay (acute toxicity test and analgesic activity). The study is limited to chemical characterization and analgesic activity of extracts from N. laevis leaves.


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