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Part I: Phytochemical Study of
Boswellia carterii
Birdwood.
1. GC/MS Analysis of Essential Oil.
2. Investigation of the Resin Content.
3. Investigation of the Gum Content.
Phytochemical and Biological Studies of Boswellia carterii Birdwood
Family Burseraceae, which was introduced into Egypt for folk medicine.
Prof. Dr. Abdel Nasser Badawi Singab, Prof. of Pharmacognosy Department, Dean of Faculty of Pharmacy, Ain Shams University
.
Dr. Khaled Meselhy, Lecturer of Pharmacognosy Department, Faculty of Pharmacy, Cairo University
.
T/A. Asmaa Ibrahim Ali, Lecturer Assistant of Pharmacognosy Department, Faculty of Pharmacy, Misr International University
.
Part II: Biological Activities on
Boswellia carterii
Birdwood.
1.
In vivo
studies:
1.1. Toxicity study.
1.2. Analgesic activity.
1.3. Acute anti-inflammatory activity.
1.4. Antipyretic activity.
1.5. Antioxidant activity.
1.6. Chronic anti-hyperglycaemic activity.
1.7. Antiwormal activity on earthworm (
Allolobophora caliginosa)
1.8. Hepatoprotective activity.
2.
In vitro
studies
2.1. Immunstimulant activity on neutrophiles of human being
3. Antibacterial and antifungal activities
1. INTRODUCTION
•Frankincense is one of the members of family
Burseraceae which produce fragrant resins used
as incense or perfume and that’s why it is also
known as incense tree family
•Oleogumresin of Olibanum is obtained from
incisions into the bark of
Boswellia carterii
Birdwood.
•Frankincense is also commonly known as
"Olibanum", or "Oil of Lebanon". It appears a
more accurate origin of the word Olibanum
may be from the Arabic word for the resin,
"Laben" or "Luban" which is a word that also
means "white" or "cream.“
•Olibanum is popularly used in Egypt to
eliminate bad cough under name of “leban
Dakar”referring to capital of Sengal.
2. Plant Material
The oleogumresin of olibanum was obtained
from the Egyptian market with certified
botanical origin,
Boswellia carteri
Birdwood
(Somalia), the identity of the sample was kindly
confirmed by Ragab El-Attar Herbal Drugs
Store &label of export source;in addition to
match physical character of sample under
investigation with published data of Somalian
type (
Boswellia carterii
Birdwood). It was also
authenticated by comparsion with a genuine
sample kept in the Drug Museum of
Pharmacognosy Department, Faculty of
Pharmacy, Cairo University
(http://www.somaluna.com/category_frankince
nse.asp).
3. Preparations of the extract and fractions for both Phytochemical and Biological activities:
The Olibanum exudate (1Kg) was extracted with absolute alcohol then filtered. The filtrate contained oil and resin, while gum was being left as a white residue. Oil was separated from
resin by subjecting it to distillation in Clavenger apparatus. Four fractions were obtained;
viz:
total alcoholic extract, oil fraction, resin fraction and gum fraction, in addition to aqueous
extract which was prepared by maceration of total oleogumresin in hot water for 24 hours. All samples were kept in tigh tlysealed containers.
Figure (1): Scheme extraction, fractionation & isolation the components of the oleogumresin of Boswellia carterii Birdwood:
1 Kg of Olibanum + Absolute Alcohol
F (Oleoresin) R (Gum) = 48% w/w
Wt= 483gm
Filter
Oil = 0.3%v/w
Hydro-distillation
HPLC analysis
Resin = 44.3% w/w
Wt = 443 gm
GC/MS analysis
Compound A Compound B Compound C Compound D
NMR & MS Spectrum
Total Aqueous Extract Total Alcoholic Extract
Essential Oil GumResin
Part I: Phytochemical Study of
Boswellia carterii
Birdwood.
1. GC/MS Analysis of Essential Oil.
Figure (2 & 3): Identified Components of the
essential oil of
Boswellia carterii
Birdwood
oleogumresin:
Figure (4): Effect of preparation method of essential
oil on percentages of the common compounds
obtained from
Boswellia carterii
Birdwood:
0
5
10
15
20
25
30
35
40
45
50
a-pinene n-octyl acetate Incensole acetate
% Extraction only
% Hydro-distillation only
% Extraction followed by hydro-distillation
Part I: Phytochemical Study of
Boswellia carterii
Birdwood.
3. Investigation of the Gum
Content.
F
igure (5): Chemical composition of
gum hydrolysate of
Boswellia
carterii
Birdwood:
Figure (6): HPLC Chart of gum
hydrolysate of
Boswellia carterii
Birdwood:
Part I: Phytochemical Study of
Boswellia carterii
Birdwood.
2. Investigation of the Resin Content.
4 compounds are isolated from the r esin: 3 triterpenoidal compounds
and 1 diterpeniodal compound from hydrolyzed resin . The
structures of these isolated compounds were established on the basis
of physicochemical data, UV spectral data with different shift
reagents, 1H-NMR and FAB+MS.
3-
O
-stilbene boswellic acid is isolated for the first time from
Boswellia carterii
Birdwood may be considered a new
chemotaxonomic biomarkerf or this specie.
OO
HO
H
H
H
Compound A: 3-O-Stilbene Boswellic acid
OO
HO
H
Compound B: Acetyl Boswellic Acid
O
HO O
HO
H
Compound C: Boswellic Acid
HO
O
H
H
Compund D: Incensole
Conclusion & Recommendation
GC/MS analysis of the essential oils of
Boswellia carterii
Birdwood showed higheroxygenated components than hydrocarbons ones which is responsible for the oil activity.
The essential oil was obtained by new method (ED).
3-
O
-stilbene boswellic acid was isolated for the first time from
Boswellia carterii
Birdwood may be considereda new chemotaxonomic biomarker for this specie
The hydrolysis of resin in
Boswellia carterii
Birdwood resulted in isolationof Incensole
The HPLC analysis of the gum hydrolysates, revealed the high estpercenta ge of glucuronic acid so, that’s why it showed valuable appli cations in both immune-stimulantth erapies.
the whole plant reserve more activities than other fractions alone due to synergistic effect of the 3 components together.
The gum recorded high hepatoprotective activity, a potent immunstimulant drug and exhibited obvious effect against
Mycobacterium phlei
which gives good indication for patients
who are suffering from tubercluosis.
The oil recorded remarkable antimicriobialactivity against both G+ve & G-ve bacteria as well as antifungal effect.
The Essential oil also posses antioxidant activity.
References
1. Adams, R.P.; (1995)“Identification of Essential Oils by Ion Trap Mass Spectroscopy”; Academic Press, Inc; New York,
London, Toronto.
2. Karber, G; (1931): Arch Exp. Pathol. Parmacol.; 162, 480.
3. Winter, G.A.;(1962): “Carrageenan - induced oedema in hind paw of the rat as an assay for anti -inflammatory drugs” Proc.
Soc. Exp. Biol. Med. III; 1544-1547.
4. Beutler, E., Duron,O. and Kelly, BA.; (1963)“Improved method for the determination of blood glutathione ” J. Lab. Clin. Med.
61, 882-888.
5. Trinder, P.; (1969): "Estimation of serum gluc ose and triglyc erides by enz ymatic method" Am. Clin. Biochem; 6, 24.
6. Thewfweld, W.; (1974): “Enzymatic met hod for determin ation of seru m AST, ALT and ALP ” Dtsch Med; 99, 343.
7. Shaala, A.Y.; Dhaliwal, H.S.; Bishop, S.; Ling, N.R.; (1979):“Ingestion of dyed-opsonised yeasts as a simple way of detecting
phagocytes in lymphocyte preparations. Cytophilic binding of immunoglobulins b y ingesting ce lls” J Immunol Methods.;
27(2):175-87.
8. Collins, C.H.; (1964): “Microbiol ogical Methods ”, P. 92, Butterworths, Lon don.
Figure (7): The Median
Lethal Dose showed
that all tested samples
are safe in the range of
used doses.
Figure (8,9,10,11 & 12): The Biological activities results for the
different fractions
0
5
10
15
20
25
area %
hexanal
a-thujene
a-pinene
a-phellandrene
limonene
trans-p-mentha-2,8-dienol
2-methyl-isoborneol
citronellal
n-octyl acetate
3,5-dimethoxy-toluol
borneol acetate
lavendulyl acetate
benzyl butyrate
a-copaene
dodecnoic acid, ethyl ester
2-hexyl-cinnamaldehyde
cembrene A
isokaurene
thunbergol
Scalrene
incensole acetate
Compound
chemical composition of the oil of olibanum
Compound
3.32
7.82
3.82
30.36
13.12
31.61
0
5
10
15
20
25
30
35
Area %
Monoterpenoids Sesquiterpenoids Diterpenes Non-Terpenoidal
oxygenated components non-oxygenated components
0%
5%
10%
15%
20%
25%
30%
35%
40%
Fucose
(0.96) Rhamnose
(1.41) Maltose
(1.76) Lactose
(1.8) Glucuronic
Acid (2.4) Xylose
(2.89) Arabinose
(3.39)
Sugars
Percentage of sugars of the gum
Percentage
LD50 gm/Kg
b.wt.